(62) Teodorovich, I. L., Rumyantseva, S.7 ZavGd.Lab*,32 (11), 1334 (1966) (Russ). (63) Thorpe, V. A., J. Ass. Ofic. Anal. Chem., 50 ( 2 ) ,394-7 (1967). (64) Tsitovich, I. K., Gaidukova, N. G., Zh. PTikE. Khim., 40 (8), 1708-12 (1967) (Russ). ( 6 5 ) Weiser, H., Riedel, V. , Chem. Tech. (Berlin), 18 (9), 561-4 (1966) (Ger).
(66) Woodis, T. C., Jr., J . Ass. Oflc. Anal, Chem,, 52 (I), 30 (1969). (67) Yarovenko, A. N., Komarova, K. A.,
Kreshkova, E. K., Zh. Anal. Khim., 21 (4), 3 9 7 4 0 4 (1966) (Russ). (68) Yonden, w.J., J . Ass. ofic.Anal. Chem., 46 (l),55 (1963).
(69) Zhivopistev, V. P., Selezneva, E. A.,
Zugagina, L. N., Sibiryakov, N. F., Uch. Zap., Permsk. Gos. Univ., 159, 238-42 (1966) (Russ).
CONTRIBUTION of.the Missouri Agricultural Experiment station. Journal Series No. 5664, approved by the director.
Food Katherine G. Sloman, Arthur K . Foltz, and James A. Yeransian, General Foods Technical Center, White Plains, N. Y.
I
N THIS REVIEW the authors have at-
tempted to provide a representative survey of advances, innovations and constructive modifications in food analysis. The publications covered generally appeared in the time span of October 1966, when the preparation of the previous review (1P) was begun, to October 1968. Where dates cited are earlier than this the work had not yet come ta the writers’ attention for past inclusion. As before, for the sake of space, identical work in American and foreign journals led t o the choice of the more familiar domestic publications especially when availability allowed checking the content of papers for applicability. Several texts have appeared which augment the field of food analysis. The subject of quality control in the food industry with a new chapter on flavor measurement is covered by Kramer and Twigg’s work (17P). The American Public Health ilssociation (2OP) has published a book on standard methods for dairy products. The proceedings of the 1966 Technicon automation symposium (2IP) have appeared and contain papers of interest to food analysts. ADDITIVES
The detection and identification of additives in foods becomes more important each year and the number and type of additives used increases steadily, Methods for antioxidants are many and varied. Dilauryl thiodipropionate and other antioxidants have been separated from lard, using a vacuum technique, by Fazio, et al. (18A). Butylated hydroxyanisole (BH.4) has been determined spectrophotometrically by formation of a nitroso derivative by Davidek, et al. (IOA). Photometric measurement of nordihydroguiaretic acid (NDGA) after reaction with molybdophosphoric acid and triethanolamine has been used by Galea, et al. (2SA). Vacuum sublimation and gas-liquid chromatography (GLC) have been proposed by McCaulley, et al. (45A) for determination of several antioxidants in lard. BHA,
butylated hydroxy toluene (BHT), and NDGA have been separated by thinlayer chromatography (IIA). BHT has been extracted from emulsifiers by iMiethke (46A) and detected by TLC or GLC. Takahashi (6SA) has reported the results of B collaborative study of the determination of BHA and BHT in cereals using gas chromatography. The presence of 24 phenolic antioxidants in oats has been shown by Daniels, et al. (9A) using thin-layer and column chromatography. Methods of analysis for preservatives have been reviewed by Schuller and Veen (61A), and a book on “Detection and Determination of Preservatives in Foods” published by Diemair and Postel (17A). Gas chromatography has been used for the determination of alkyl ether derivatives of 4hydroxybenzoates by Wilcox (67A), for the determination of sorbic and benzoic acids in wine by Wurdig (7OA) and investigated for a number of preservatives by Amano, et al. ( 2 A ) . The technique of steam distillation, thin-layer chromatography and UV spectromety has been applied to the analysis of solid foods for benzoates by Lewis (43A). -4 thin-layer chromatographic procedure has been used by Dickes (16A) for the separation and identification of 4-hydroxybenzoic acid and its esters in foods. Monselise (47A) has described an extraction procedure and subsequent spectrophotometric measurement for sodium benzoate and potassium sorbate in preserved fruits and vegetables. Ionexchange chromatography has been used by Ford (21A) to determine benzoic acid in soft drinks. Thin-layer chromatography has been described by Ludwig, et al. (44A) and Roidich, et al. (69A) for the separation and identification of some preservatives. A colorimetric procedure for 4-hydroxybenzoic acid with diazotised nitroaniline has been described by Aoki, et al. (SA). Benzoic acid has been determined polarographically after nitration by Davidek, et al. (13A). Procedures for dehydroacetic acid using separation and coloration on cation exchange resin (69A) and anion
exchange resin (608) have been described by Sakai, et al. Hydrogen peroxide and sorbic acid were detected in fish paste products by Kanno, et al. (36-4) using colorimetry for the peroxide and sorbic acid after steam distillation. A spot test using phloroglucinol in trichloracetic acid-acetic acid has been used for sorbic acid in wine by Alessandro ( 1 A ) . Screening and quantitative methods for sorbic acid in orange juice have been described by Floyd (19A). iln improved procedure for recovering sorbic acid from foods using vacuum steam distillation has been suggested by Kirnura, et al. (S7A), and other preservatives have been recovered by this technique (b2A). Dialysis has been used as a means of separating preservatives for spectrophotometric measurement by Hamaguchi, et al. (28A). Thin-layer chromatography has been proposed by Takeshita, et al. (64A) as a means of determining 2(2-furyl)-3-(5-nitro-2 furyl) acrylamide in foods. Double development on thinlayer plates has been used by Gosseli, et al. (25A) to separate nine common preservatives. Diethylcarbonate has been determined in wine by Brandenburg, et al. (6A) and by Reinhard (54A) using gas chromatography. Diethylpyrocarbonate has been determined by Kanno, et al. (35A) using gas chromatography, and by Pauli, et al. (52.4) by colorimetry. Gas chromatography of their trimethylsilyl derivatives has been used by Sahasrabudhe (57A) as a means of analysis of polyglycerols and their fatty acid esters. Glycol and sorbitan esters have also been analyzed using the silylation technique by Suffis, et al. (62A). Propylene glycol esters of fatty acids have been separated using silicic acid chromatography followed by gas chromatography (58A). A simple method for the detection of sorbitan mono- and triesters has been proposed by Kroeller (4OA) using thin-layer chromatography. A procedure for the presence of fatty acid mono- and diethanolamides uses chromatography on silica gel G (41A). VOL. 41, NO. 5, APRIL 1969
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Paper and column chromatography has been used for the analysis of the fatty acid esters of sucrose by Bares ( 5 A ) . Glucono-&lactone has been detected in sausages by thin-layer chromatography and colorimetry by Braun, et al. (“A) in meat by infrared spectrometry as used by Gunther (27.4) in meat products by polarimetry in the presence of molybdate as proposed by Hamm, et al. (29A) and by thin-layer chromatography and identification by fluorescene as described by Niemoller (50A). A gas chromatographic method for triethyl citrate and triacetin in eggwhite has been proposed by Kogan, et al. (38.4). A column of acetylated dextrin has been used by Balakhontseva, et al. ( 4 A ) for the determination of glycerine in the presence of other poly01s. Sugar alcohols in dietary biscuits have been determined by the gas chromatographic analysis of both their trimethylsilyl ethers and their acetate esters by Jones, et al. (%’A). A procedure for sorbitol has been suggested by Hundley, et al. (S1A) using periodate titration after the degradation of reducing sugars by alkaline hydrolysis. Gelling and thickening agents have been detected by Padmoyo, et al. (51A) using electrophoresis on cellulose acetate film. Added vegetable polysaccharides in meat products have been detected by Gspahn, et al. ( H A ) using thin-layer chromatography. Kross (42A) has patented a method for determining ethylenediamine-tetraacetic acid in meat products after formation of the nickel chelate. Wiskerchen (68A) reported on results of a collaborative study of a method for sodium lauryl sulfate in egg whites using Azure A. Nitrite in meat products has been determined by Davidek, et al. (11A) using colorimetry with ethacridine lactate, by Truhaut, et al. ( M A ) using Saltsmann reagent for colorimetry, by Nagata, et al. (48A) using colorimetry after potassium ferricyanide clarification, and in molasses by Goslich (24A) using the reaction with l-naphthylamine. A new colorimetric method for sulfur dioxide based on its oxidation with quinhydrone has been proposed by Kroller (S9A). An apparatus for the electrometric detection of the endpoint of the titration of cyclamate with nitrite has been described by Richardson, et al. (56A). Excess of barium after precipitation of the sulfate in the determination of cyclamate is determined by EDTA titration as described by Davies (14A). Gas chromatographic procedures for cyclamate utilizing the reaction of cyclamate with nitrous acid to form cyclohexene have been described by Rees (5SA), Richardson, et al. (55A). A colorimetric procedure for cyclamate has been described by Johnson, et al. (SSA) which entails hydrohysis of cy64 R
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ANALYTICAL CHEMISTRY
clamate to cyclohexylamine and colorimetric determination of the amine. Derse, et al. (15A) determined the cyclohexylamine by gas chromatography. Kamp (S4A) has used TLC on silica gel G to separate and identify dulcin, sodium cyclamate and sodium saccharin. Cereal flours in prepared starches have been detected by Thalacker (66A) by the use of density-gradient centrifugation. Paper electrophoresis has been used by Ney (49A) for the detection of egg white in liquid yolk. Immunodiffusion has been found useful in the identification of barley flour in wheat flour (8.4). The use of galactose oxidase has been suggested by Hankin (SOA) for the determination of nonfat dry milk solids in meat products. The determination of glycopeptides has been used by deKoning (20A) as a method for the detection of whey powder in milk powder. ADULTERATION, CONTAMINATION, AND DECOMPOSITION
Methods for adulteration detection continue to be compiled, particularly those involving chromatographic patterns for comparison with pure standards. Fats and oils have received considerable attention in this respect. A review by Mani, et al. (102B) lists 153 references on this subject and a survey by Roos (1S8B) deals with milk fat adulteration. Gas chromatography is still probably the most useful technique for establishing fat adulteration. Elaidic acid measurement was used for olive oil quality evaluation in papers by hverill ( 7 B ) , Ferraris (48B), Kleinert and Habegger (87B in English, 86B in German), and Oleic-Linoleic Martinenghi (106B). acid ratios were used by Galanos, et al. (61B). GLC analysis of methyl esters was also used to detect lard adulteration by Fedeli et al. (47B), fats added to cocoa butter by Bonar ( I S B ) and butter fat in margarine by Withington (178B). Chromatographic analysis of unsaponifiable matter also proved useful in detecting one fat added to another. Animal fat adulteration down to 2.5% of vegetable oils was revealed by a GLC technique by Ettinger, et al. (46B). Vegetable oil adulteration in milk fat was determined by sterol analysis by Katz and Keeny (82B) and Parodi (114B). Thin-layer chromatography provided means to separate and detect ghee adulterated with vegetable oils in results reported by Ramamurthy, et al. (1SSB) and Chakrabarty, et al. (28B). This technique (TLC) also permitted analysis for small amounts of mineral oil in fats by Siets (147B) and for adulteration in olive oil by sterol analysis in a paper by Doro (SQB). Adulteration of coconut oil with other vegetable
oils was detected by Mani et al. (1033) using TLC. A turbidity test by k a n a Campos (SB) is claimed to detect 1% of foreign fat in olive oil. Marine oils as adulterants are specifically detectable by chemical and spectrophotometric means according to Franzke (55B). The adulteration of fruit juices has been investigated using many components as markers. Alberola, et al. (1B) used GLC of the sugars of citrus juices toward this end. Carotenoids were separated by TLC to detect adulteration in citrus juices by Primo Yufero, et al. (1S1B)and Benk, et al. (9B). Alvarez (2B) detected adulteration of noncitrus and citrus juices, primarily using TLC. Primo Yufero and his associates also employed GLC of nonvolatile acids as methyl esters (129B) as well as mineral analysis (ISOB)to detect citrus adulteration. dl-Malic acid added to apple juice was identified by paper chromatography by Pilnik (12SB). Concord grape juice adulteration was investigated by Mattick, et al. (I07B) and Fitelson (61B)using paper chromatography. This latter author (62B) also applied this technique to other dark colored fruit juices to reveal adulteration. Bidmead etal. (I1B)trapped and identified unfamiliar GLC peaks to confirm flavor and juice adulteration. A method for the detection of animal proteins foreign to meat has been described by Wyler and Siegrist (180B) and blood added to hamburger was determined by an iron method by Hankin (69B). Fredholm (57’B) reported on pentoses and pentosans added to meat. Satoskar, et al. (IdOB)used saponins to detect mahua cake added to ground nut cake. Red beets were identified in capsicum spices by Schwien and Miller (144B). Gums in wort and beer were determined by Schuster, et al. (14SB). A higher sensitivity to smaller quantities of water added to milk is claimed for the Beckel method by Braunsdorf (15B). Interest remains high in detecting and measuring mycotoxins and other harmful contaminants in foods. A book published by the National Academy of Sciences (1IIB) deals with toxicants occurring naturally in foods. Marth (IO@) describes qualitative methods for aflatoxins. Wiley (177B) showed a n improved TLC developing solvent. Scott (145B) published a note on green coffee aflatoxin analysis and Levi and Borker (98B) presented a survey of green coffee for potential aflatoxin contamination. Stoloff, et al. (158B) recommended benzene as a superior spotting solvent for TLC analysis. Fluorodensitometric measurements of aflatoxin spots on TLC plates were discussed by Peterson, et al. (120B),Beckwith and Stoloff (8B), and Pons et al. (127B). Determinations of aflatoxins in cottonseed products were published
by Stoloff, et al. (157B) and Pons, et al. (126B). I n the analysis of aflatoxins in ground nut products, Jayaraman, et al. (81B) recommended dialysis extraction to avoid destruction by methanol while Eppley (43B) and Stacchini (153B) reported procedures using chloroform as extractant. The distribution of aflatoxins in individual kernels was shown by Cucullu, et al. (37B). Campbell and Funkhouser (24B) and Eppley, et al. (45B) reported results for collaborative studies on ground nut butter and products. Wine was examined for aflatoxin B1 and histamine by Schuller, et al. (142B) and Davis, et al. (38B) separated aflatoxins BI, GI plus BZ and Gz from fermentation medium using paper chromatography. Aflatoxin M in milk was estimated by Purchase and Steyn (132B). Eppley (44B) has reported a screening method for Zeoralenone, aflatoxin, and ochratoxin. Ochratoxin A in cereal products was measured by Scott and Hand (146B). Substances potentially misinterpreted as aflatoxins are shown by Shotwell, et al. (148B) in oats and in many other foods by Frank and Eyrich (54B). Polynuclear aromatic hydrocarbons in foods, especially those of proven carcinogenic natures, have been investigated extensively. Such is the subject of a review by Tilgner (165B). White (175B) described the thin layer chromatography of these compounds. The occurrence of polycyclics has been described in coconut oil by Biernoth and Rost (12B), in various crude vegetable oils by Grimmer and Hildebrandt (67B) and also by Howard, et al. (78B). Ciusa, et al. (32B) analyzed olive oil. Howard, et al. (76B) surveyed solvents used in extracting edible oils for polynuclear hydrocarbons. Various roasted food materials were investigated. Pertoldi-Xarletta (119B) assayed coffee unsaponifiable extracts for carcinogenics. Fritz (59B) looked a t roasted malt and coffee and barley and malt. Grimmer and Hildebrandt (66B) analyzed aqueous extracts of coffee and tea. The same authors (65B) spectrophotometrically determined polycyclic aromatic hydrocarbons in a variety of vegetables. Spanyar, et al. (151B, 152B) used gas and thin layer chromatography to detect condensate components from smoking foods. hlalanoski, et al. (101B) surveyed smoked foods for polycyclics. Mannelli (105B) detected benzopyrene in smoked foods while Howard, et al. (75B) reported a collaborative method study for benzo(a)pyrene. Narziss, et al. (11OB)determined this compound in beer. Howard and coworkers (77B) developed a general method for total diet composites with respect to polycyclic aromatic hydrocarbons. These compounds were separated by TLC as their
picric acid complexes by Kessler and Mueller (84B). Trace levels of other contaminants have been investigated widely also. Cooper, et al. (34B) and Huis in’t Veld, et al. (80B)have determined hexoesterol residues in meat and Stone (159B), in feeds and premixes. Frank (53B) published a routine test for antibiotics in milk and milk powder. Kiss, et al. (88B) described a thin-layer method for alkaloid contaminants in foods. Morpholine containing carbon 14 was used for coating fruit and recovered and measured by 6 counting by Carmon, et al. (25B). Paper chromatography permitted isolation of ricinine from castor beans in a paper by Ferri, et al. (49B) and of solanine from potatoes by Schilling and Zobel(14IB). Hammonds (68B) detected cashew-nut shell liquid through TLC of the anacardic acid. Sarma, et al. (139B) used paper chromatography of the alkaloids of argemone oil to detect it in edible oils. Tutin and hyenachin were estimated in honey using TLC and intracerebral injection in mice comparatively by Turner (168B). Trace solvents in foods have been repeatedly analyzed, particularly through the medium of gas chromatography. Ethylene was identified in gibberellic acid treated potatoes by Poapst, et al. (124B). Plasticisers were analyzed after diffusion into foods by Tengler (265%) and Pfab (121B). Milk has been investigated for the presence of styrene monomer from containers by Finley and White (50B) and for dioctyl phthalate by Cerbulis and Ard (27B). Mesityl oxide traces from paint reacting in meat to produce cattyodors was elucidated by Patterson (116B). Dichloromethane in beer made with hop extracts was measured by Vogl and Schumann (172B) and Brandenberger (14B) used carbon 14 trichloroethylene to establish its incorporation in coffee beans. Hydrocarbon solvent residues in edible oils were gas chromatographed by Watts and Holswade (173B) and mineral oil in bread was determined via alumina column chromatography by Silverberg (150B). Residues from fumigation are also of concern as illustrated by papers on ethylene oxide by Ben-Yehoshua, et al. (IOB),Kroeller (92B), and Pfeilsticker, et al. (122B). Bromide residues from methyl bromide treatment were analyzed by bromophenol blue color formation by Kretzschmann and Engst (89B) and by X-ray fluorescence by Getzendaner, et al. (64B). A colorimetric procedure for phosphine fumigation residues was recommended by Kroeller (93B). HCN in prunus seeds and other foods was determined by Hanssen and Sturm (71B, 160B), ethylenediamine was measured in microgram quantities in milk in a fluorimetric method by Pasarela
and Waldron (115B) and Chojnicka (SIB) used a modification of a colorimetric method to determine O . O O l ~ o of triethylenetetramine in milk. Hordynska, et al. (74B) used existing methods for sodium dodecylbenzenesulphonate and laurylpyridinium bromide in milk bottle rinsings and Charro Arias, et al. (SOB) investigated soluble coffees for unauthorized surfactant content. Rentschler (135B) utilized diethyl oxydiformate to detect chemical preservatives in wine. Organotin stabilizers were separated using TLC by Helberg (72B). Westoo (174B) determined methylmercury residues in fish with electron capture gas chromatography. Mercury traces in honey were reported by Pourtallier (128B). Heavy metals and arsenic contamination of food additives were tabulated by Briski, et al. (18B). Contamination of foods with extraneous matter has considerable significance both from a sanitary and consumer acceptance point of view. A review of “filth” control in Western Europe by Maes (100B) listing progress since 1945 has appeared. New extraction methods for light filth have been published by Vazquez, et al. (171B) for pecans, Gecan, et al. (63B) for peanut butter, and Thrasher, et al. (164B) for paprika. Variations of existing methods have been recommended by Thrasher (163B) for egg products and by Reed (134B) for flour. The AACC and A 0 4 C methods for flour were compared by Kurtz and McCormack (95B). Miller (109B) showed a rapid method for extraneous matter in maize meal, mustard and soya-bean flour and Kurte (94B) made suggestions for flour and cinnamon analysis. Roaf, et al. (137B) also gave a procedure for ground cinnamon. Insect fragment methods were published for cocoa by Stein, et al. (155B), Brickey ( I 7 B ) , and Gecan, et al. (62B). Freeman (58B) gave criteria for determining internal insect infestation by radiographic analysis. Brickey, et al. (16B) suggested sampling operations and Wright (179B) used staining to facilitate visualization in examining hops for aphids. Stein, et al. (154B) also used staining to count eelworms in vinegar. Riley, et al. (136B) and Coulter (35B) described methods for fly eggs in tomato products. Brown and -4ho (21B) and Brown (d0B) determined maggots and extraneous matter, respectively, in canned mushrooms. Leaf miners in canned spinach and turnip greens were detected by Brown (19B) also. Stephens (156B) separated extraneous matter from dairy products. A recovery technique for mould in beverages was illustrated by Miller (108B). Dvorak, et al. (41B) recommended a procedure for sand in food products after comparative study. VOL. 41, NO. 5, APRIL 1969
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Many indices for the detection of decomposition have been explored, especially in countries dependent on seafood for a large part of their food supply. Avakyan (6B) used 2 , 3 , 5 triphenyltetrazolium chloride as a colorimetric hygienic indicator in meat and fish products. Dugal (4OB) followed hypoxanthine formation in iced fresh water fish as did Hughes and Jones (79B) in herring. An Auto-Analyzer method for this compound was described by Burt, et al. (23B). Wierzchowski, et al. (176B) used free amino acids to detect fish decomposition and an increase in these was noted by Lapshin and Rodina (96B) in stored canned smoked fish in oil along with a decrease in soluble proteins and phenols. Phosphates were shown to inhibit fish protein changes in saline storage by Nikkila, et al. (112B). Uchiyama, et al. (17OB) concluded that ice storage freshness reduction is more biochemical than bacterial in cause. Changes in nucleotides a t cold temperatures were investigated by Fraser et al. (56B) in mackerel, Fujii, et al. (6OB) in plaice, and Tomiyama, et al. (166B) in carp. Tsukuda and Amano (167B) studied discoloration in three species of red fish. Larry and Salwin (97B) attributed shrimp spoilage color changes to cryptoxanthin. Total volatile bases in fried fish were used to assess spoilage by Pearson (117B) while Castell, et al. (26B) followed trimethylamine formation in frozen cod and Burnett (22B) used ammonia for crab-meat. The development of dimethylamine and formaldehyde in frozen Alaskan pollack was measured by Tokunaga (169B) and Hansel, et al. (7OB) determined formaldehyde in several seafoods. Hydrogen sulfide and volatile basic nitrogen were studied in fish at various storage temperatures by Osada, et al. (113B). A simple color test is claimed to indicate deterioration in cod by Connell (SSB). A review by Pearson (118B) lists quality control chemical techniques to assess meat freshness. Hills and Smith (73B) used gas chromatographic methods to detect irradiated horse meat and Champagne (29B) enumerated changes in irradiated animal fats. Volatile decomposition products from heated corn oil were investigated by Krishnamurthy (9OB), Kawada, et al. (83B), and Krishnamurthy and Chang (92B ) . The proteins of heat damaged anchovy meals were examined by Silva and Contreras (149B). A greenish discoloration in cold stored butterfat was traced to a carotenoid change by Lueck (99B). Kirk, et al. (85B) studied flavor deterioration in rapidly sterilized milk using GLC techniques and Arnold (4B) studied sterilized concentrated milk flavor changes. Tatum, et al. (I61B) reported nonenzymic browning products 66 R
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ANALYTICAL CHEMISTRY
in orange powder. Dworschak and Endelyi (42B) correlated heat treatment of fruit juices to hydroxymethyl furfural content. Albumin protein changes were examined electrophoretically by Croizier, et al. (36B) in stored eggs. Damaged starch in wheat flour was determined by enzyme hydrolysis and a sugar method by Audidier, et al. (5B) while Porneranz, et al. (125B), using fractionation studies, showed lipid breakdown to cause inferior breadmaking performance in storage damaged flour. CARBOHYDRATES
Procedures for the accurate determination of sugars, polysaccharides, and related compounds continue to be investigated including many chromatographic and spectrophotometric procedures. Glucose has been determined colorimetrically by Braun, et al. (9C) using the reaction of iodate, unconsumed after reaction with glucose, with fluorescein. An enzyme-photometric procedure for glucose and fructose using hexokinase and glucose-6-phosphate dehydrogenase has been described by Tschersich, et al. (73C). A similar procedure has been applied to wine and grape must by Drawert, et al. (21C). An improved resorcinol reagent has been described by Yaphe, et al. (85C) useful for the determination of fructose and 3, 6 anhydrogalactose in polysaccharide. Cold anthrone has been used by Van Handel (76C) to determine fructose and fructose yielding carbohydrates. Further development of the method has extended its application to the direct determination of sucrose in the presence of reducing sugars (75C). Modifications of the Nelson-Somogyi method for reducing sugars have been suggested by Marais, et al. (44C). A sensitive direct photometric procedure for fructose and sucrose has been proposed by Garrett and Blanch (29C) using acid degradation, and UV measurement of the chromophore produced. The UV absorption after reaction of sugars with hydrochloric acid has also been used by Doyle, et al. (2OC) to determine individual sugars when the identities are known. Spectrofluorimetric measurement after reaction of monosaccharides and sucrose with aniline phthalate or 2-naphthylamine phthalate has been described by Coassini-Lokar (1 4C). An A4uto-Analyzer procedure for sugars has been described by Buchta (11C) using a reagent consisting of cysteine hydrochloride in sulfuric acid. Titrimetric procedures include the determination of glucose by glucose oxidase ( 5 4 3 , a modification in the Tryller electrometric apparatus (47C), and a description of the construction and use of a commercial electrometric
end-point detector (17C). Complexometric determination has been used for the determination of carboxyl groups in oxidation products of sugars by Kopriva, et al. (S9C) using the isolation of the zinc salts of the acids and subsequent EDTA titration of the zinc. Unreduced copper after reaction of glucose with an alkaline copper reagent is titrated with EDTA using a nietallofluorescent indicator without separating the reduced copper (6C). A cupriargentimetric determinat,ioii of reducing sugars has been described by Celsi, et al. (1%’). The measurement of glucose and maltose in potato starch syrup has been described by Rychlik, et al. (6OC) using optical rotation and iodine titration. -4polarimetric determination of glucose has been developed by Martin (45C) using readings before and after enzyme oxidation of the glucose with glucose oxidase. Studies of the direct polarimetric determination of sucrose by the addition of borax indicate that in the presence of glucose and fructose this is not an exact analytical method (23C). Unreduced copper from the reaction of reducing sugars has been determined by atomic absorption by Potter, et al. (55C). Hydrogen produced in the reaction of sodium borohydride with a n aldehyde or ketone group of the carbohydrate is measured in a nitrometer in a method for the determination of reducing sugars (roc), 4 special selfheating tablet has been used by Wisler, et al. (81“) to determine reducing sugars in potatoes. d-Fructose and derivatives are reviewed
(84C) Gas chromatography of the trimethylsilyl derivatives of simple sugars has been simplified by Bethge, et al. (7C) by the introduction of an equilibration step that permits the total amount of a particular sugar to be calculated from a single peak. An inert internal standard has been used by Halpern, et al. (32C) to aid the quaiititation of silyl derivatives of glucose. Molasses carbohydrates have been examined by Walker (77C) using ion-exchange clarification, and gas chromatography of the silyl ethers. Thin-layer chromatography of sugars has been described by Berger and Borodkin (4C) using cellulose, silica gel, and special spotting reagents, and by De Stefanis, et al. (18C) using silica gel. Buffered silica gel has been used by Lombard (42C) to separate sugars after acid hydrolysis. I n the presence of glycerol Shellard, et al. (65C) have recommended the use of silica gel G buffered with boric acid for thin-layer chromatography of sugars. “Chromagrams’J have been found by Anderson, et al. ( I C ) to provide a simple and accurate technique for the separation of reducing sugars. Garofalo (28C) has described thin layer chronintography on sheets of inert glass micro-
fibres impregnated with potassium silicate. TKO dimensional thin layer chromatography has been applied to complex sugar mixtures by Figge (24c), to mono-, di- and trisaccharides by Pastuszyn, et al. (53C), and has been used by Lato, et nl. (4OC) to improve t’he number of sugars capable of being separated by thin-layer chromatography. Paper chromatography has been used by Jantzef and Potter (35C) to determine raffinose in sugar-beet molasses. A sensitive spotting reagent for sugars using a fluorescent detection of formaldehyde after periodate reaction has been proposed by Weiss, et al. (79C). Improved methods for preparation of sugar spray reagents, aniline phosphate and p-anisidine phosphate have been developed by Marais (4%’). Sixteen monosaccharides have been separated by Jonsson and Samuelson (SSC) on a strongly basic anion exchange resin; Ohms, et al. (49C) have separated twelve neutral sugars on a new anion resin in the borate form. Glucose has been separated from galacturonic acid and sulphuric acid by means of an anion exchange resin (41C). hlono-, di- and trisaccharides have been separated by Walborg and Lantz (78C) by ion-exchange chromatography using boric acid-glycerol buffers. Continuous column monitoring has been employed by Kesler (37C) in a procedure for the rapid separation of mixtures of saccharides, glucose polymer-homologs, and soluble hemicellulose by anion exchange. Thin-layer chromatographic procedures for sucrose in musts and wines have been described by Stella, et al. (SSC) which incorporate the color reagent in the developing solvent. An improved sucrose-refractive index correlation has been calculated by Thoburn (72C). A glucose oxidase procedure has been applied to the determination of sucrose in beet molasses after enzymatic inversion (SQC). Active charcoal has been used by Sawyer (SSC) as a clarifying agent for raw sugar solutions to be used for polarimetric sugar determinations. Polyphenolic interferences with carbohydrate determinations have been removed by the use of a n insoluble polyphenol adsorbent (SSC). The saccharide distribution of corn syrup has been determined by Huber, et al. (S4C) using a thin-layer chromatography and direct densitometry procedure which is applicable to saccharides up to monosaccharides. Thin-layer chromatography has also been used to separate hexoses and oligosaccharides (64C), with elution followed by colorimetric measurement. Rlono- up to octa-saccharides from beer and wort have been separated on silica gel G thin layers (25C). A charcoal and Celite column has been used by Davy (16C) to separate oligosacchardies, and by French, et al. (ZSC) to separate starch
oligosaccharides. Gas chromatography of the silyl ethers has been used by Brobst and Lott (IOC)t o determine the carbohydrates of corn syrup and wort. A scheme for the separation of the polysaccharides of green coffee beans has been described by Thaler, et al. (?IC) using solvent extraction techniques. Wolfrom, et al. (82C) have separated two polysaccharide residues from instant coffee powder and determined constituent sugars and physical properties. Major low molecular weight carbohydrates of potato have been isolated and characterized by Urbas (74C). Precipitation with glycosylphenylazo dye has been used by Yariv, et al. (8SC) to separate and isolate polysaccharides from maize and soya beans. Extraction procedures using various salt solutions have been used by Aspinall, et al. (2C) to fractionate the polysaccharides of soybeans. The use of thin-layer chromatography and infrared spectromety for the identification of polysaccharides has been described by Gunther, et al. ( S I C ) . Colorimetric determination by the phenol-sulfuric acid method has been used by Kim (38C) to determine unfermented material in high-fermentable syrup. Ferricyanide numbers have been determined by Commerford, et al. (15C) for glucose and glucose polymers up to G 10. Methods for starch in meat products have been described by Ojtozy (51C) using polarimetry or gravimetry. An enzymic determination of starch in dietetic foods has been developed by Ruttloff, et al. (59C) using glucoamylase and glucose oxidase measurement of the glucose produced. A quantitative extraction of glycogen has been described by Kowlan, et al. (4SC) which uses perchloric acid extraction followed by digestion of the residue in potassium hydroxide. Richter (57C) has determined amylose in the presence of amylopectin using a spectrophotometric titration with iodine. Photometric titration of starch with iodine-iodate has been performed automatically in a special apparatus (68C). Starch damage has been determined by Medcalf and Gilles (4SC) using iodine absorption measured by amperonietric titration. Standardization of the acid hydrolysis step has been found by Winkler and Luckow (8OC) to improve the precision of the Ewers polarimetric method for starch. Polarimetric determination of starch in the presence of glycogen has been achieved by separating the glycogen by its solubility in alcoholic potassium hydroxide (5OC). The types of commercial starches have been identified by Binns, et al. (SC) by colors formed after treatment with potassium hydroxide and subsequent acidification. An improved spectrophotometric method for the determination of starch in sugar crystals uses iodine determination of the starch after acid-alcohol
precipitation ( I S C ) . Fractional precipitation with butyl alcohol and methyl alcohol has been used by Rakhimbaev (66C) to separate amylose and amylopectin. Susceptible starch in wheat flour has been determined by Audidier, et al. (SC) using a-amylase in a timed reaction. Changes in starch gelatinization have been studied by Sullivan (SSC) including microscopic, enzymatic, and spectrometric examination. Mass spectrometry of carbohydrate derivatives has been reviewed (SSC). Infrared spectra of carbohydrates have been determined by Parker and Ans (5%’). Polyhydric alcohols and sugars have been separated and quantitatively determined by Dutton, et al. (22C) using gas chromatography of the silyl derivatives. A thin-layer procedure for sorbitol in fruits has been described by Stoll (67C). Partition chromatography on an anion exchange resin has been used by Samuelson, et al. ( S I C ) for the estimation of alditols in food. The reaction of tetrazolium salts with sulphated polysaccharides has been studied by Graham (3OC). Friedemann, et al. (27C) has reviewed and evaluated chemical methods for the determination of “available” carbohydrates in foods. Pectic substances in fresh and preserved fruits have been discussed by Doesburg (19C). A comparison of the A.O.A.C. fiber method and the dimethyl sulphoxide method by Zentner (87C) has shown that the results are identical if the fiber content is less than 4.5%. An indirect calorimetric estimation of lignin in foods has been presented by Bergner, et al. (5C). The extinction at 420 mp can be transformed by formula to the color index for refined sugar, and a n electronic absorptiometer has been developed (3%’) to measure this color index directly. COLOR
Anthocyanins and flavonoid compounds have been separated by gas chromatography of their silyl derivatives by Keith, et al. (22D). A new extraction procedure for anthocyanins after removal of sugar by fermentation has been proposed by Pourrat, et al. ( S S D ) and applied to bilberry juice. Koch, et al. ( I S D ) have partially separated the anthocyanins of black currant juice using Sephadex columns, and Morton (27D) has applied thin-layer chromatography to the same problem. Studies of anthocyanin in cranberries have been carried out by Fuleki and Francis (150, 16D) using column chromatography and by Puski and Francis (S7D) using paper chromatography. Strawberry flavonoids have been fractionated by Co, et al. (YD), and characterized using paper chromatography, spectrophotometry, and color reactions. VOL. 41, NO. 5, APRIL 1969
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A method for the extraction of hesperidin and citroflavonoids has been proposed by Thomas, et al. ( 4 5 0 ) . Somers ( 4 2 0 ) has described the resolution and analysis of the total phenolic constituents of grape pigment. Studies of B-carotene in fruits ( 2 D ) ,in the yolk of hen’s eggs ( S D ) , and in duck egg yolk ( 4 0 )have been described by Benk and collaborators. Values for the carotene content of these products are given. Hamed (180) has proposed a spectrophotometric method for B-carotene and lycopene in tomatoes and tomato products. A scheme for the qualitative fractionation of the carotenoids of potatoes has been described by Kasim (210). The carotenoid pigments of arachis oil have been extracted and characterized by Pattee and Purcell (310 ) . Studies of the pigments of wine include the determination of anthocyanins (390), a new method for anthocyanin glycosides by Dorier, et al. (130) and paper chromatographic techniques for detecting catechins, leucoanthocyanins, and tannins described by RibereauGayon, et al. ( 4 0 0 ) . Studies of malvin in wine include fluorimetric determination described by Bieber (60), by Hadorn, et al. ( 1 7 0 ) ,and by Eisenbrand et al. ( 1 4 0 ) . Tannins in wine have been determined by an improved oxidation procedure using a polyamine adsorbent by Pokorny, et al. (36D),and thin-layer separation has been suggested by Diemair and Polster (11 0 ) . Evidence concerning the structure of three flavanotropolones in tea has been obtained by Takino, et al. (440). A procedure for the detection of the dye alkannin in liquors has been described by Benk ( I D ) . The use of thinlayer chromatography for the assay of annatto preparations has been proposed by Dendy (100). Water soluble food dyes have been separated using polyamide powder and identified by thinlayer chromatography on polyamide by Davidek, et al. (go),and on cellulose layers by Lehmann, et al. ( 2 4 0 ) . Sephadex has been used by Parrish (SOD) for the chromatography of food dyes. Pearson (340) has listed the R P values of permitted water soluble colors on paper, and Dobrecky, et al. (120) have proposed the use of twodimensional paper chromatography to separate dyes permitted by the European Economic Community. Other techniques for detection and identification of food dyes include high-voltage paper electrophoresis of water soluble coal tar dyes described by Niitsu (290), use of a high-molecular weight amine for extraction and subsequent infrared identification by Oi, et al. ( 2 8 0 ) , and polarographic studies of water soluble dyes made by Mizunoya, et al. (260). 68 R
ANALYTICAL CHEMISTRY
Oil-soluble colors in oils have been separated by Jones (2OD) using column chromatography, while Reiners (380) has proposed separation using ferric hydroxide and thin-layer chromatography. Oil soluble dyes in paprika have been studied using thin-layer chromatography (60) and CopiusPeereboom, et al. (80) suggest the use of polyamide and silver nitrate impregnated silica gel for thin-layer chromatography of some fat soluble dyes. Pearson (33D) has published ultraviolet curves for Black 7984, a newly permitted food color, and Rp values for Ponceau 6R ( 3 2 0 ) . A method for uncombined intermediates in F.D. & C. Blue No. 1 has been proposed by Johnson (190). Gel filtration has been used by Rother (410) to detect caramel color in fruit concentrates, and by Stinson and Willits ( 4 3 0 ) to separate the coloring matter of maple and cane sugar syrups. The brown components of roasted coffee have been separated and characterized by Maier, et al. ( 2 5 0 ) using nylon column chromatography. Weichel ( 4 6 0 ) has described a simple method for betanin as a means of evaluating spray-dried beetroot powder.
ENZYMES
A procedure for a-amylase described by Perten (18E) uses starch colorimetry and is applicable to high and low aamylase activity cereals. A starchiodine colorimetric procedure suitable for very low a-amylase activities has been described by Winkler and Luckow ( H E ) . A procedure for a-amylase activity in cereals, proposed by Rohrlich, et al. (20E) uses the distance travelled in 4 minutes on a strip of filter paper as a measure of enzyme activity. Catalase activity in milk has been measured by Willits, et al. (25E)by the use of a disc-flotation test. An assay procedure for 8-glucuronidase in cow’s milk has been described by Kiermeier and Gull (10E) using extraction of the phenolphthalein formed into butyl acetate and then into alkaline glycine for color measurement. hlilk lipase has been determined by Parry, et al. (IYE) by titration, using a substrate of butter oil emulsified in gum acacia and automatic addition of alkali during the course of the reaction. A micro-manometric method has been used by Primo Yufera, et al. (19E) to measure the carbon dioxide produced from sodium bicarbonate by the action of acid groups liberated from a pectin substrate as a measure of pectinesterase activity in citrus juices. Pectin methylesterase in strawberries has been determined by Leuprecht, et al. (14E) by titration;
methods for handling the samples are discussed in detail. Guenther and Ihrckhart (5E) have studied the procedure for total acid phosphatase using p-nitrophenylphosphate, as applied to apples, and have concluded that the optimum reaction pH is 5.65-5.85. Total acid phosphatase in honey has been determined by Gunther, et al. (6E) using a similar substrate a t pH 5.3. O’Brian (16E)has described a method in which the phenol released by the action of milk phosphatase on disodium phenyl phosphate is coupled with alkaline 4-aminophenazone and potassium ferricyanide and measured colorimetrically. Babson and Greeley (1E) have suggested the use of phenolphthalein monophosphate as a substrate for alkaline phosphatase in milk, and a collaborative study of the procedure has been completed by Kleyn, et al. (12E). Procedures for the isolation and fractionation of phosphatases from orange peel have been described by Schormuller, et al. (21E) using fractional precipitation with acetone and chromatography on Sephadex C50. Polyphenoloxidase determinations have been made by Lukach, et al. (16E) on wheat flour using ascorbic acid substrate in the presence of pyrocatechol, by De Amorini, et al. ( 4 E ) using L-3-4 dihydroxy-phenylalanine substrate, and by Voigt and Noske (22E) using catechol and Besthorn hydrazones as substrate. A substrate combining the collagen of ground heat-denatured kangarootail tendons with a brick-red azo dye is used by Brenner, et al. (2E) to provide evidence of proteolytic chill-proofing enzymes in beer. A direct assay of proteolytic enzymes in beer based on hydrolysis of NZ-benzoyl-DL-arginine 4-nitroanilide to produce 4-nitroaniline has been described by Weissler, et al. (23E). Papain in beer has been determined by Collier (SE)by measuring the formation of turbidity by the action of papain on casein. Proteolysis in milk has been measured by Hammond, et al. (8E) by dye-binding with Orange G. Saccharase activity in honey has been determined by Hadorn and Zurcher (YE) using optical rotation measurements to follow the reaction. The activity of xanthine oxidase in milk has been measured by Kiermeier, et al. (11E)by its rate of oxidation of xanthine and measurement of the potential-time curve. Honold (9E) has published a study of the oxidation-reduction enzymes in wheat including separation and quantitative measurement of the enzymes. A. technique for the determination of initial rates of enzyme reactions has been described by Lee (13E). Improved techniques for enzyme resolution by starch gel electrophoresis have been described by White and Kushnir (2Cm
FATS, OILS, AND FATTY ACIDS
Articles dealing with analysis of fats and oils in foods have continued to increase dramatically. Williams (2 58F) has provided a new edition of a text reviewing methods of analysis for fats and oils with emphasis on gas chromatography (GC), thin-layer chromatography (TLC), and lipase hydrolysis. Methods and approaches to analytical problems are also given in Vol. 4 of “Advances in Lipid Research” (1 f 9 F ) and Cocks and Van Rede have edited the useful “Laboratory Handbook for Oil and Fat Analysts” ( I S F ) . Jensen, et al. (70F) review GC as applied to analysis of the fatty acids of milk and describe varied methods of extraction and esterification as well as necessary instrumental conditions. Pallotta (1 18F) presents a comprehensive review of TLC applications to the separation of components of food lipids and also reviews methods ( I f 7 F ) of analyzing for auto-oxidation products. Limitations and suggestions for improvement are given for methods used in evaluating quality of vegetable oils (12OF) and Woidich (I59F) reviews practical methods for determining the fatty acid composition of lipids by formation and GC of the corresponding methyl esters. A review ( f 1 8 F )is given of methods and observations pertaining to development of fat rancidity in bakery products. Reviews are also given of analytical data obtained for grain lipids ( S Z F ) and for the composition and structure of triglycerides present in milk fat (69F). Privett and Nickel1 provide a survey ( I S f F ) of recent advances made in the application of ozonolysis to locating double-bonds in unsaturated fatty acids. Comparisons (SOF, 57F) are made of methods of methyl ester formation from fats and oils for subsequent GC analysis and Hadorn, et al. compare manual methods of quantitating fatty acid ester GC data with a method employing an integrator (56F) (the latter method was found to have the lowest standard deviation). Results of collaborative studies (104F) of methods for determining fat in milk showed significant differences for data obtained by the Uabcock, Roese-Gottlieb, and modified detergent methods and Lee, et al. have also compared (94F) six methods for determining lipids in fish meal. Investigations of the effectiveness of various solvent systems for extracting lipids from raw beef (58F) showed the chloroform-methanol extractioii to be useful, particularly with respect to efficient removal of phospholipids. Zmachinski, et al. ( f 6 1 F ) compare methods for determining essential fatty acids in hardened fats and describe an enzymatic procedure for determination of only the essential cis-9, cis-12-octadecadienoic acid and not the
unessential isomers. Infrared and NMR methods are given ( I 4 F ) for detecting and quantitating the occurrence of aromatic fatty acids formed during hydrogenation of polyunsaturated fatty acids in oils and Johnson, et al. (71F) compare the utility of mass spectral data of the diacetyl and the trimethylsilyl ether derivatives of 1- and 2-monoglycerides for purposes of qualitative identification. A comparison of GC methods for determining the composition of the medium and short chain fatty acids of butterfat (128F) showed the use of butyl esters to give superior results to those obtained using methyl esters. Rapid methods for determining the amount of fat in meat products for industrial control are described ( f O I F ) with methods based on changes in the refractive index or density of selected solvents due to fat being rated as appropriate for this purpose. Changes in the refractive index of selected solvents have also been employed in the determination of fat in cookies and baked products (28F), soups (S5F), chocolate ( I f F ) , canned foods, (7F) and fish products ( f S 9 F ) . An I R method is reported (1 4 F ) for determination of fat and moisture in meat products and Streuli, et al. (150F) report that more accurate results are obtained in determining the fat in green and roasted coffees if the ground sample is treated with 4N hydrochloric acid prior to extraction. A modified Babcock method is described (155F) for determining the fat in meat wherein dimethyl sulfoxide is used for dissolving interfering substances but not the triglycerides. Wide-line NMR has been applied to the rapid determination of the oil content of soybeans (16F) and Pohle and Gregory (127F) recommend increased cooling of samples over previous recommendations made for the measurement of solids in fats and shortenings by NMR. Olley (1 f S F ) discusses the relative merits of methods for removal of fat from fish meals and Pomeranz, et al. (ISOF) compare the lipid composition of a single wheat kernel and its structural parts by use of TLC. The surface lipids of fresh and processed raisins were compared using solvent separation, column chromatographic separation into functional categories and GC of selected fractions ( f S 8 F ) . The results thus obtained showed that the presence of foreign oils added to such products could be detected and determined. Pokorny, et al. (119F) described a column chromatographic method for evaluating advanced stages of rancidity of fats and oils which is reported to be more reliable than determinations of peroxide, benzidine and thiobarbituric acid values and Rothe, et al. (136F) describe a method for monitoring the degree of rancidity in
cereal products b y TLC of the 2 , b D N P derivatives of the higher a l d e hydes which are found. A comparison was made of several methods used to follow changes during the auto-oxidation of meat lipids ( f 2 4 F ) and a modification is discussed for the thiobarbituric acid method in determining the fat rancidity of freeze-dried meat (84F). Garg, et al. (48F) have reported on studies regarding breakdown of milk fat during cheese ripening, Amano ( 4 F ) has compared the properties of the condensation products formed with 2thiobarbituric acid for selected aldehydes and oxidized soybean oil, and Becker, et al. (fIF, f S F ) have described methods for determining oxygen and nitrogen and also for detection of primary oxidation products in oils, fats and emulsions. Schoenmakers (1 4OF) has examined the reliability of the 2thiobarbituric acid test in the presence of inorganic ion and concludes that up to 0.5% of ferric ion does not interfere with the method. An I R method is given for determining small amounts of epoxides (f.49F) by measurement of spectral changes associated with the opening of the epoxide ring with the limit of detection stated to be approximately 0.1 micromoles per ml. The use of picric acid has been described as a reagent for the colorimetric determination of epoxides in heated vegetable oils (49F),seed oils (SOP) and also as a spray reagent for detection of epoxides on TLC plates (44F). Gaddis, et al. have tested methods for the isolation of carbonyls from fat by comparing quantitative data obtained for individual aldehydes (46F) and monocarbonyl compounds (47F). GUSS,et al. determined (56F) that the lipoxidase content of wheat decreases with increasing refinement and was lowest in the flour fraction. Krewson (86F) reports on identifications of fatty acids containing oxirane functional groups which have been found in wide distribution in seed oils. Seher describes a stepwise TLC procedure (14SF) for determining the oxidized fatty acids present in frying fats and Oette reports on identifications made of lipid peroxides (If IF) by TLC on Silica gel G. Mizuno, et ai. (106F) showed that the high values obtained in determination of carbonyls because of peroxide interference could be avoided by reduction of the peroxides to noncarbonyl compounds prior to analysis. Levkovich, et al. (96F) describe a volumetric method of determining epoxides by formation of the corresponding chlorohydrins followed by determination of the hydroxyl groups. Fioriti, et al. (45F) have identified both gamma and delta saturated lactones as being present in highly peroxidized vegetable oils and Chakrabarty, et al. describe paper and thin-layer methods (19F) suitable for detecting rearrangeVOL. 41, NO. 5, APRIL 1969
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ment reactions occurring in natural glycerides. Clarke, et al. (22F) report the GC conditions used for obtaining resolution of mixtures of mono- and dicarboxylic free fatty acids and Appleby, et al. (5F) describe the GC conditions used to separate and determine monobasic lower fatty acids (up to capric) directly from aqueous solutions. GC has been applied to separation and determination of short chain-length fatty acids after formation of the ethyl esters in a sealed tube (75F) by heating salts of the acid with Dowex resin (H+ form) and ethanol, and Lough, et al. describe an improved procedure for the complete extraction of fatty acids from foods (98F). Jackson (66F) recommends either passing carrier gas through water or incorporating H3P01 in the column liquid phase in order to maintain columri efficiency when using silicone oil-fatty acid columns for the GC determination of fatty acids. Kaderavek, et al. (74F) and Hote-Baudart (63F) have applied GC to the determination of free fatty acids in cheese and Kintner and Day (80F) have similarly determined the major free fatty acids of milk. A method is reported ( O W ) for identifying higher fatty acids-e.g., myristic and palmitic acidson a paper chromatogram and a colorimetric method is given for determining free fatty acids in vegetable oils (11F) based on extraction of the copper soaps. An ultramicro method is given by Novak (121F) for determining the free fatty acids in serum (50 wl of serum is required) by extraction of cobalt soaps with heptane and formation of the cobalt complex with 1-nitroso-Znapthol and MacKenzie, et al. (1OOF) report a rapid micro method for free fatty acids based on the colored complexes formed with uranyl ion and Rhodamine B. Velasco (154F) describes the analysis of free fatty acids in cottonseed oil (free of gossypol) by measurement of conductivity after addition of aqueous ammonia and Wood (161F) makes use of trifluoroacetate and trimethylsilyl ether derivatives to determine longchain fatty alcohols (Cld to C,) by GC. A procedure for fractionating triglycerides differing by only one methylene group or by one double bond (and also for those containing both cis- and transfatty acids) was presented (110F) wherein reversed phase partition column chromatography was followed by GC of the separated triglycerides. Litchfield gives conditions for the GC resolution (96F) and quantitation of triglycerides differing by only one carbon number and Kuksis (88F) describes the fractionation of triglyceride mixtures by preparative GC. Evans, et al. (S7F) have fractionated the polar triglycerides of seed oils according to degree of polarity by use of silicic acid column chromatography and Sato, et al. 70 R
ANALYTICAL CHEMISTRY
(138F) have examined various column packings for their applicability to separating triglycerides by GC. A generalized method is given (61F) by Hayakawa for calculating the weight ratios or mole fractions of each type of triglyceride in natural fats and Piorr, et al. (126F) describe application of a fluorimetric method to follow structural transformations undergone by unsaturated acid groups in lard due to bleaching. A spray reagent for detecting lipids on TLC plates is described by Jones, et al. (7SF) and fluorescence is used to follow the penetration of oils into fried foods (107F) by examination of cross sections under a microscope using reflected ultraviolet radiation. A description is given of a method ( 6 F ) for determining saturated and unsaturated monobasic acids (C, to C,) and dibasic acids (C, to C12) by GC of the n-propyl esters and the problems involved in the analysis of the minor nontriglyceride components of edible oils are discussed (4OF) and methods of choice are given. Kuemmel, et al. (87F) describe the analysis of methyl octadecenoate and octadecadienoate isomers by combined liquid-solid and gas chromatography and an I R method is described (99F) for the determination of mono- and diglycerides in butter fat with the capability of determining as little as 0.2% of added monoglyceride. Mallard and Craig (IO2F) report a GC method for the quantitative analysis of oleic and petroselinic acids in glyceride oils after quantitative oxidation to the respective nonanoic and lauric acids. TLC methods are given for determining steroids in milk (108F) and soy bean oil (1.451’7) and a system is given ( 1 2 I F ) for the quantitative TLC of standard and tissue neutral lipids which incorporates semi-specific colorimetric and titrimetric methods on eluted material. Paulose describes (123F) a TLC method for separating fatty acid methyl esters according to both chain-length and unsaturation and Peters, et al. (125F) recommend the use of a methyl ester of synthetic homophytanic acid as an internal standard for quantitation of GC analysis of methyl esters prepared from fats. Raju and Reiser (13%’) describe the determination of cyclopropene fatty acids by GC analysis of the corresponding methanethiol addition products and Sigler, et al. (146F) give a method for determining unsaturated compounds by titrating with lead tetraacetate in the presence of bromine. Scholfield, et al. (142F) have fractionated the geometric isomers of methyl linolenate by argentation countercurrent distribution and identification has been made of 24methylenecycloartanol in olive and linseed oils (42F). GOUW,et al. (5.427) give the kinematic viscosities of fatty acid
methyl esters and it is reported ( I F ) that good agreement was achieved between GC and calculated values of equivalent chain length for multiply branched fatty acids. Kaufmann, et al. (79F) have reported results of their analyses of yeast lipids and Dyatlovitskaya, et al. ( S S F ) employ TLC to determine structure of lecithins after enzymatic hydrolysis. A procedure is given (78F) for determining phospholipids and their fatty acid compositions and Kuznetsov, et al. (91F) describe new color reactions for detecting lecithin, cephalin, and sphingomyelin in foods. Teague and Joe (161F) describe analyses of unsaponifiable residues in milk, Knapp, et al. ( 8 S F ) have identified unsaponifiable components of lettuce and chromatographic procedures are given (76F) for isolating components of oil unsaponifiables for identification. Jacini, et al. (65F) give a summary of the composition of unsaponifiable matter of some vegetable oils including preliminary data obtained by a nondestructive procedure applied to olive oil. Minor components of the unsaponifiables from different anatomical parts of the soya bean are reported by Fedeli, et al. (41F) and Copius-Peereboom (27F) gives methods and data obtained in identifying phytosterols from rapeseed and coconut oils. An alternate method for determining unsaponifiables by use of a mixed bed ion-exchange resin is described by Geoghegan, et al. (49F) and Karleskind, et al. (77F) report on methods and data obtained for determining sterols in fats and oils and also make use of the data thus obtained to determine the composition of mixtures of fats and oils. Preparative TLC on Florisil is used by Miettinen, et al. (103F) for isolation of dietary and faecal neutral steroids prior to GC analysis and Florisil columns are used (82F) by Kiribuchi, et al. to isolate the sterols of soybean oil for subsequent identification. A GC procedure for determining glycerides and polyglycols as their benzeneboronic acid esters is given by Kresee, et al. (85F) and a low temperature method for rapidly preparing quantitative yields of methyl esters by reaction with diazomethane and UV radiation (116F) is also reported. Hornstein, et al. (62F) describe a procedure for separation of muscle lipids into respective classes of compounds and Ackman presents GC methods used for analysis of monoenoic fatty acids of rapeseed oil (2F) and for determining the esters of herring-oil (SF). Black and Beal describe the determination of unsaturation in oils in the presence of aldehydes (17F); Brown, et al. (18F) give a procedure for rapid determination of unsaturation by use of a “hydrogenation valve” (which prevents admission of Nal3Ha solution when hydrogenation is
complete); and Tinoco, et al. (153F) describe a rapid procedure for locating double-bonds in unsaturated fatty acids. The structure of unsaturated glycerides of vegetable oils was determined (38F) by use of a counter-current distribution apparatus (200 tubes) and lipase hydrolysis. The cyclopropenoid fatty acid content and fatty acid composition of crude oils from twenty-five varieties of cottonseed have been determined (9F) and analytical methods for cyclopropenoids are given (59F, 8 F ) . Christie (20F) has investigated the feasibility of determining unsaturated esters after first converting them to the corresponding cyclopropanes. Baltes (IOF) described a method of determining sulfur in fats by a hydrogenation procedure. Isolation of unsaturated isomers of oils is accomplished with silver nitrate impregnated silica gel columns (16F) followed by G C analysis in the separation of unsaturated components of fish oil ( 3 1 F ) and butter (39F, 90F) and Morris (109F) reviews the history of silver-ion olefin separation methods (168 references). The reactions of silver nitrate have been employed by others (71F, 81F) for detection and estimation of cyclopropene acids in fats and Emken, et al. (36F) used silver-resin columns followed by GC for separating and determining conjugated geometric isomers. Jamieson and Reid report on the isomerization products formed during saponification of oils containing linoleic acid (6°F) as well as the alkaline isomerisation products formed from linoleyl acetate and octadeca-9,la-diene (68F). A method is given for the microdetermination of trans-isomers of monoethylenic (long chain) fatty acids in the presence of their cis-isomers by TLC with subsequent GC analysis (93F) and Wood and Snyder (160F) report a G C method for determining long-chain isomeric glyceryl monoethers as the trifluoroacetyl and trimethylsilyl derivatives. Miwa, et al. (106F) report on use of an automatic titrating hydrogenator for determination of unsaturation in oils and Davison, et al. (29F) describe a micro-reactor for methanolysis of triglycerides prior to GC. Sgoutas (144F) doubly labeled the methyl esters of linoleic, stearic, and oleic acids with aH and I4C prior to passing them through GC columns. Fractions of each effluent peak were collected a t 20 second intervals and then examined in a scintillation counter. A progressive decrease in the ratio of aH to I 4 C with increasing relative retention times for the three peaks indicated that fractionation had occurred on the columns. Gerson, et al. (60F) report that losses of methyl esters of polyunsaturated acids during G C analysis increases on Celite columns with degree of unsaturation. Tichy, et al. (152F)
compare results obtained by paper chromatography with those obtained by T L C for serum cholesterol esters and conditions are described which permit the complete removal of one unsaturation class from another by TLC of the mercury adducts (166F) and also the bromomercuri-adducts (1578’). A two-column G C sequence is described for separation of fatty acid methyl esters (148F) according to chain length and pyrogallol red and thymolphthalein were used by Sliwiok, et al. (147F) for detection of higher fatty acids on TLC plates. GC analysis of sheep milk fat (9°F) showed qualitative similarities to butter fat but significant differences were found for certain fatty acids. Sandev, et al. (137F) have identified free fatty acids of cheese by liquid-liquid chromatography and Kuzdal-Savoie, et al. (89F) have performed a chromatographic comparison of the glycerides of a normal cheese with a cheese noted to have a bitter quality. The fatty acid composition of olive oil was determined by fractionation and G C analysis of the methyl esters (64F, 25F), and GC was also used to determine the fatty acid composition of fish (53F), milk (62F), commercial butters (5187, and Scholfield, et al. (141F) report on a liquid chromatographic procedure for determining the geometrical and positional isomers of fatty acids in partially hydrogenated fats. A method is given (16F) wherein the oil contents of dry-milled corn fractions are determined by GC after a simultaneous extraction-transesterification step (methyl esters) and a multistage TLC procedure is given (34F) for the complete structural analysis of fatty acid mixtures. Ruseva-Atanasova, et al. (136F) describe a n identification system for fatty acid esters which involves two-dimensional, combined gasthin-layer chromatography wherein the G C effluents are deposited onto a logarithmically travelling TLC plate start-line. TLC methods for identifying fatty acid methyl esters are also given by Ord, et al. ( 1 1 4 F , 115F) and Rao (IS@‘).
FLAVORS AND VOLATILE COMPOUNDS
Gas chromatography (GC) continues to play an ever increasing and dominant role in flavor work from the standpoint of both separation and quantitation, with use being made of the improved volatility of derivatives to isolate and then identify the larger molecular species present in natural flavors and aromas. Indeed, the widespread application of derivative formation prior t o analysis has provided much of the thrust to the progress currently being made in the flavor field. Analysts still rely heavily on spectrometric methods
of identification with high resolution mass spectrometry and proton resonance spectrometry playing more important roles as molecular size and complexity of isolates increase. Review articles cover the subject of flavor from the standpoint of both the chemist and the physiologist (69G, 96G) and a published symposium (134G) includes a comprehensive picture of the current “state of the art” for many major food commodities. Nursten and Williams (I07G) provide a survey of components identified in fruit aromas and Baraud (13G) reviews gas chromatographic characterization work done for various wine aromas. Efforts have been made to realize the potential of gas chromatography for providing an objective measure of flavor quality and to thus supplement organoleptic methods. This principle has been employed for rating the products of distilleries (36G), for beer production (17G, 9SG) and for determining the quality of brandy (S6G, 117G). Discriminant analysis of GC data has been applied by Miller (95G) to the end of describing staleness of potato chips and by Powers and his coworkers (116G) as an aid to generally classifying the flavor quality of foodstuffs. Forss and coworkers (45G) describe methods of concentrating volatiles from dilute aqueous solutions without use of organic solvents, and Shipton and Whitfield (132G) describe a procedure for recovering sufficient higher boiling volatiles from aqueous alcohol for subsequent direct analysis by combined G C and mass spectrometry. A collection device and technique are reported (97G) for achieving on-column trapping of flavor volatiles from a gas chromatograph and an approach is given (108G) for removing troublesome water from solvents containing food volatiles. Teranishi (158G) compares the relative merits of open-tubular columns versus packed columns for aroma research via GC, and Phifer and Plummer (112G) describe a method of separating polar compounds from a mixture using water vapor in the carrier gas and water as the liquid phase. Pyruvoyl chloride 2,& dinitrophenylhydrazone is suggested (136G) as a reagent for isolating alcohols from lipids, and a system is also reported for quantitative micro-analysis of carbonyl compounds by formation and elution of their 2,4-dinitrophenylhydrazones using a treated celite column (110G). Colorimetric methods are given for the determination of acetaldehyde (9G, 87G), and an improved microcoulometric gas chromatographic detector is described for specific response to volatile sulfur compounds (BG). Gottauf (56G) tells of a n improved “headspace” technique for measuring traces of volatiles in aqueous solution, and Wientjes, et al. (17lG) report a proceVOL. 41, NO. 5, APRIL 1969
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dure for measuring the isostatic permeation of volatile food aromas through packaging films. Sato, et al. form the acetates from alcohols (129G) to minimize tailing and to effect sharp separation by GC. Use was made of thin-layer chromatography (TLC) to identify carbonyl compounds in a fermented glucose solution (122G)and a review is given (152G) of methods which have been used for determining the aroma composition of alcoholic beverages. An I R method for determining the ethanol content of potables is reported by Tanaka and Ono (154G). Collaborative results are reported (25G) comparing methods for benzaldehyde in flavors and cordials and a colorimetric method is given for determining higher alcohols in beer (S8G). Spectrophotometric methods are described for determining the bitterness of beers flavored with isohumulone concentrates (176G) and also for determining H2S and volatile thiols in beer (127G). Verzele and Verstappe have applied preparative scale GC to separate volatile aroma components of hops (164G); Drews, Specht, and Schwartz have used TLC as a means of identifying the volatile alcohols of beer (S9G). An apparatus is described for stripping beer of its volatiles for GC analysis (4OG) and GC is also used in the characterization of wort, beer and brewing-syrup carbohydrates (90G), for volatiles from beer (115G), for determination of diacetyl and pentane-2,3-dione in beer headspace (58G), and for the determination of tyrosol and tryptophol in both beer and wine (109G). Van Wyk compares the aroma constituents of White Riesling grapes and wines (16SG). Pollard, et al. (11SG) describe a head-space technique for determining the higher aliphatic alcohols in the fusel oil containing fractions of ciders and perries by GC, and methods of determining benzaldehyde in flavors and cordials (26G) and fusel oil in distilled spirits (27G) are discussed by Brunelle. The composition of fusel oil in Scotch whiskey has also been investigated (68G). Polarography is used to determine carbonyls in wine (SCG), and TLC is used to determine the dicarbonyl compounds of whiskey and cognac (12SG). TLC is also used in conjunction with GC to determine the carbonyls of crude spirits (IZ4G). Spectrophotometry was used with paper chromatography ( I I G ) to determine aromatic compounds developed by distilled spirits stored in various types of oak barrels, and spectrophotometric methods are also described for measuring the total phenolics of wines (140G),for determining 2-furaldehyde in spirits (157G), and for determining small amounts of benzene in spirits (168G). Results of collaborative studies are 72 R
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reported for determining the lead number of vanilla extract by chelometric titration (66G) and for detecting flavor additives in vanilla extracts by TLC (70G). Jackson describes his efforts in characterizing vanillas as to source by G C (65G) using coumarin as an internal standard, Smith compares methods (141G) for determining vanillin in vanilla extracts, and Blanc, et al. (18G) describe a TLC procedure for separating vanillin and ethyl vanillin from commercial flavorings. Methods are given for the determination of Shydroxymethyl-2-furaldehyde by GC in natural products after derivatization (64G) and also by a colorimetric procedure used in honey (119G). The identification and determination of quebrachitol (146G) in maple sap and syrups is achieved by GC of the corresponding trimethylsilyl derivative. I R is used to identify sesquiterpenes of black pepper after G C separation ( I W G ) ,and Brand makes use of TLC to determine p-hydroxybenzaldehyde, vanillin, and syringaldehyde in grass lignins (2SG). Salem, et al. used chromatographic methods to follow the carbonyl compounds produced by sugar and amino acid reactions in bread systems (128G); Hunter and Walden apply GC to analysis of carbonyls regenerated from the semicarbazones prepared of baked bread aromas (62G); and Walter, et al. report on the volatiles formed by thermal decomposition of glucose (165G). Neutral (8G) and basic (177G) components of rice vinegar have been determined and the main acrid components of Japanese horseradish powder are also reported (75G). Rosebrook and Barney propose an improved method for determining volatile isothiocyanates in mustard seed and flour (125G). Volatiles stripped from butter oil have been further identified by use of G C and mass spectrometry (46G) and comparisons have been made of methods of isolation and identification of lipid volatiles of butter fat systems (SG,47G). Results obtained for the volatile fatty acids in butter have been compared for data obtained by GC of the methyl esters and by direct GC (81G). Urbach (161G) and Kinsella, et al. (74G) report on the TLC separation of lactones from butter fat and Abousteit (1G) gives results obtained by TLC of the 2,4dinitrophenylhydrazones of butter carbonyls. The monocarbonyls in Russian and Dutch cheeses were studied (41G) and G C was used to identify amines and bases in cheese flavor (54G, 56G). The volatile flavor compounds of cheddar cheese were followed by Bradley and Stine (22G) and neutral flavor volatiles stripped from Swiss cheese were measured and compared (8SG,84G). Sensitive radioactive tracer techniques were applied to determine volatile sulfur
components of Cheddar cheese made from milk obtained from a cow fed with 85S (76G) and the volatile acids of caciocavallo and white cheese aromas were determined by steam distillation and G C (160G). Acetoin was measured in cottage cheese by the diaminobenzidine method (6SG), and the diacetyl content of buttermilk was polarographically determined (46G). Scanlan, et al. made a study of heat induced volatiles in milk (1SOG); Sundararajan and coworkers report on application of a quantitative procedure for measuring head-space aroma by G C over sterile concentrated milk (151G); and Muck, et al. assayed the carbonyls of milk using a photometric method (98G). Components of coffee aroma have been identified on volatile concentrates obtained from molecular distillation of coffee oil (149G, 48G) with identification of various nitrogen bases isolated from these concentrates also being reported (5SG). Compositional data for coffee aroma is reported by several other workers in the field (20G, 150G, 147G) and a review article summarizes much of the qualitative information (29G). Spanyar (144G) makes use of GC to measure the volatiles lost from coffee extracts during freeze drying, and Radtke, et al. follow the changes in coffee aroma which occur with storage (118G). Volatile carbonyls from coffee oil were isolated as their 2,4-dinitrophenylhydrazone derivatives (166G) by column chromatography, and Kung, et al. (80G) make use of K M R and G C to determine the volatile acidity of coffee beverages. Components of cocoa aroma are reported (4SG, 91G, 162G) with identifications made chiefly by GC retention times, mass spectrometry, and I R spectrometry. 4-Methyl-bvinyl thiazole is reported by Stoll, et al. ( I 48G) as being present in trace amounts in cocoa and contributing a nut-like odor. The aromatics of tea are also identified (178G, 99G, 126G, 24G, 21G), and Nakagawa (10ZG) described effects of roasting on the nature and origin of the polyphenols of green tea. Pomazanov, et al. report a comparison of the volatile substances from different tea varieties and their relationship to flavor quality (114G). Characterizations were made of lactones isolated from beef fat (169G), a technique minimizing production of artifacts is described for extraction of chicken meat volatiles (86G) and a colorimetric method is reported for determination of diacetyl in bologna (159G). Zaika, et al. have investigated (181G) procedures for separating water soluble beef aroma precursors, and Solms gives a general review of the flavor and aroma substances reported in meats (14SG). The volatile carbonyls froin roast chicken were determined colorimetrically (85G) and marked variations
were found for small differences in treatment. Volatile flavor compounds were identified from codfish (175G) and crab meat (15SG),and paper chromatography was applied to determination of phenols in cured fish (179G, 180G). Pearson (111G) describes a correlation between the total volatile nitrogen of fish and freshness. Characterization of the flavor of canned snap beans is described (145G), and volatiles isolated from peanuts are also reported (92G). Newell, et al. (105G) compare gross analysis of peanuts before and after roasting to locate constituents involved in flavor development. Aroma components found in soy sauce (10G) and soybeans (7G) are described, and a paper chromatographic procedure for detection of phenols in soy bean meal is also given (137G). Smouse, et al. have identified components of reverted soybean oil (142G) as fractionated by repetitive GC, and Wilkens, et al. (172G) use GC as a means of characterizing effects of processing on flavor development of soybean milks. Means of effecting the GC separation of hydrocarbons from the more polar components of soybean oil is described (88G) by use of activated alumina packed columns. Two dimensional paper chromatography was used to determine polyphenolic compounds in canned tomato pastes (120G) and comparisons were made by GC for the amounts of isoamylol, pentanol, and 3-hexen-1-01 in tomato juices with varietal and harvest differences (67G). GC comparisons were also made of both the head-space aromas (50G) and vacuum distillates (72G) from different varieties of tomatoes. Dalal and coworkers (SSG) describe the volatiles of developing tomato fruit grown under both field and greenhouse conditions, and Katayama, et al. (7SG)have monitored changes of tomato juice volatiles during storage using various types of plastic packaging. Nelson (10SG) made use of an oil extraction technique and combined GC and A I S analysis to follow the flavor volatiles of processed tomatoes stored in cans, and GC mas also used (52G) to monitor volatile tomato flavor components through the ripening of fruit and manufacture of tomato concentrates. Identifications were made from cooked cabbage aroma (89G), and Hrdlicka, et al. monitored volatile carbonyl compounds during the storage of cabbage (60G) and processing of carrots (61G). GC has been used to follow changes in onion aroma through freeze drying (14G) and to compare onion volatiles for different varieties of onions (82G). The volatile aliphatic disulfides from fresh and dehydrated onions are compared (15G) and aromas have also been analyzed for potatoes and potato products ( I S S G , 28G). A method is given for determining the volatile reducing substances
in peas (139G) and techniques are presented for obtaining concentrations of flavor volatiles from frozen peas (170G, 1S8G). Murray, et al. describe a method of fractionating the flavor volatiles of foods by use of silica gel columns (101G) and apply the technique to peas and bananas for examination by combined GC-MS. Studies are also reported for the flavor of roasted barley by Wang, et al. (167G) and Shimizu, et al. (1S1G). Schultz, et al. (IS6G) report identifications made of orange volatiles as determined by both GC and MS, and Norman, et al. (106G) used GC to compare the volatiles from injured and uninjured oranges stored a t various temperatures. Spectrophotometric assays of limonin are given (SOG, 17SG) for oranges, and Attaway and coworkers (11G)give rapid colorimetric methods for determining oxygenated terpenes, aldehydes and ester concentrations in aqueous citrus essences. A review is given (174G) listing and comparing components identified in orange juice and oil, and a comparison is made of the amount of naringin found in various citrus fruits (49G) and grapefruit juice (57G)by TLC and fluorimetry. Correlations were made (79G) between the organoleptic rating of apple juices and their analysis by GC. GC has also been used in conjunction with >LIS and organoleptic evaluations (44G) to determine the contributions made by individual volatiles in Delicious apple essence. Apple juice volatiles have been examined by other workers using GC (19G, 16G, 78G), and Drawert, et al. (S7G) used GC to characterize apple flavor concentrates obtained a t various stages of fruit maturity. Angelini and Pflug (4G)used GC and MS to monitor the volatiles in controlled atmosphere storage for apples, and Kulesza, et al. (77G) used TLC to identify aromatics in apple juices exposed to varied processing. Identifications of apricot volatiles (256G, 155G), papaya volatiles (71G ) , cranberry volatiles (5G, 6G, S2G), pear volatiles (51G), and pineapple volatiles (SIG, 121G) are also reported. Neurath, et al. (104G) describe the GC and LIS characteristics of naturally occurring ethyl citrates and report their occurrences in several fruits. Jurics (69G) describes a paper chromatographic method for determining catechol and epicatechol in fruits, and Mehlitz and rvlinas have described the I R technique they used for determining carbonyls separated by TLC from pomegranate-rind oil (94G). IDENTITY
Many studies continue on the constituents of foods and on descriptive analysis for the purpose of identifying a food or a food in a food. I n the field of alcoholic beverages, Schneyder, et al. (61H)
have tabulated data on the inorganic constituents of Austrian wines, and Maurel, et al. ( S 8 H ) have reported gas chromatographic data on several types of rum. Gas chromatographic studies have also been reported by Drawert, et al. ( 1 8 H ) on spirits including wine, cognac, and whiskies. Fatty acid composition of both Turkish and German butter samples has been described by Metin (40H). The least variable chemical characteristic of ghee is reported by Rale, et al. (45H) to be the butyric acid number. For cereal foods, Silano, et al. ( 6 S H ) report that polyacrylamide gel electrophoresis of the proteins may be used to detect barley flour in wheat flours and macaronis. Matveef (S7H) has published new methods for bran and germ in wheat using enzyme hydrolysis and sulfuric acid treatment. Infrared spectrophotometry is used by Brogioni, et al. (10H) as a means of characterizing durum wheat flours. Correlation of calcium and phosphorus contents of Edam and Tilsit cheeses with fat content are tabulated by Mair-Waldburg, et al. (S4H). Cheeses, such as Cheddar, Blue, Camembert, etc., may be distinguished from each other by the electrophoretic patterns of their peptides on polyacrylamide gel according to Ney, et al. (4SH). Lactose content is reported by Motz ( 4 2 H ) to be a more reliable index of the milk in milk chocolate than the determination of milk protein. Hansen (25H) suggests a spectrophotometric method for the determination of chocolate in chocolate milk or ice cream. Iodine precipitation of the alkaloids is described by Laskowski (SOH) as a method for the determination of cocoa and coffee in ice cream. Barbiroli ( 6 H ) has determined the fatty acid content of the glycerides of coffees during roasting. The mineral constituents of apples have been determined by Wilkinson and Perring (58H). Thin-layer chromatographs described by Duggan ( 1 9 H ) of the hydroxy-flavone glycosides of apples and pears has provided different chromatographic patterns for these fruits. Boland, et al. ( 8 H ) have reported analytical data for red sour and sweet cherries. Quality standards for citrus fruit juices have been discussed by Magaudda, et al. ( S S H ) . Mineral constituents of orange and lemon juices have been tabulated by Benk ( 7 H ) ,and the results of a survey of potassium and phosphorus contents of Israeli orange and grapefruit juices have been issued ( 2 H ) . The free amino acids in Israel orange juice have been determined by Coussin, et al. (15H). A procedure for serine has been described by Morgan (41H) and suggested as an index of orange content of soft drinks. Disc electrophoresis patterns of fruit proteins have been determined by Clements VOL. 41, NO. 5, APRIL 1969
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( I S H ) and found to be characteristic for the fruit used. Zook, et al. (6011) have presented data on the mineral composition of fresh fruits. Fini (22H) has reviewed the physicochemical properties of honey including sugars, amino acids, and ash constituents. The fatty acids of cocoa products and commercial cocoa butters have been determined by van Wijngaarden (57H). Column chromatography has been used by Steiner and Bonar (64H) as a means of separating mono- and di-oleoglycerides and differentiating cocoa butter, illipe butter, and Coberine. Fresh information on the minor constituents of corn oil has been reported by Nilsson, et al. ( 4 4 H ) . Lolito and Cucurachi ( S 1 H ) have obtained data on the fatty acid composition of lard. Differential thermal analysis has been used by Mares ( S 6 H ) to detect beef tallow in lard. The fat and cholesterol contents of various fish have been determined by Wurziger and Hensel (59H). A study of the fatty acid composition of edible marine fish oils has been reported by Khalid, et al. (1811). Color reactions of red palm oil (47H), and sesame oil ( 4 6 H ) , have been described by Rao, et al. Edible vegetable oils have been analyzed for fatty acid composition by Grieco, et al. (24H). Triterpene alcohol composition has been proposed by Fedeli, et al. (21H) as a method for differentiatingvegetable oils. The fatty acid composition of whale fats from different parts of the body has been investigated (50H). A study of the fatty acid patterns of margarine and its source materials has been used by Imamura, et al. (27H) as a rough means of detecting animal fats in margarine. Many studies of fish proteins have been described as a means of identifying fish species. Lane, et al. (2QH) have described a procedure for cellulose polyacetate strip electrophoresis. Disk electrophoresis of Pacific fish has been used by Chu ( 1 2 H ) to distinguish rock or sole, and the results of a collaborative study have been reported by Thompson (56H). Cooked fish may also be identified by disk electrophoresis according to Mackie ( S 2 H ) . Thin-slab polyacrylamide techniques have been described by Cowie ( 1 6 H ) , and agar-gel electrophoresis by Hill, et al. (26H). An enzymic method which uses starch-gel electrophoresis to locate esterase bands has been proposed by Thompson (65H) as a further means of animal and fish species identification. Methods for the determination of meat in meat products proposed by Castledine, et al. (11 H ) include precipitin tests and gas chromatography of the fatty acids. Baltes ( 4 H ) has determined the composition of meat extracts from beef, sheep, whale, and sperm whale, and applied the determination of carnosine (@-alanylhistidine dipeptides) and anserine plus balenine contents to the 74 R
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determination of these extracts in bouillion cubes (6H). A spectrophotometric method for the identification of cow and buffalo milk has been described by Roy (49H). Gel electrophoresis of the milk proteins has been used to detect cow milk in human milk ( 2 S H ) , and paper electrophoresis to detect differences between buffalo and cow milk (2OH). Analytical data on the chemical composition of buffalo milk has been compiled by Abd-El-Salam ( 1 H ) . The proteins of cow, ewe, and goat milk have been separated by electrophoresis and the patterns have been used for identification of these milks in cheeses ( S H ) . Analytical data for commercial peanut butters have been reported by Roberson, et al. (48H). Organic acid composition of potatoes has been related to variety (51H), and electrophoresis of potato proteins has also been used to identify potato varieties (17H). Carbohydrates in spices were examined by paper chromatography ( 1 4 H ) . Analytical values for hot-water extractives in China tea have been determined by Manley (S6H). Data on the alkali-soluble fraction of tomato peel has been obtained by Brieskorn, et al. (9H). Characteristic values for vinegar have been established by Mecca (S9H). INORGANIC CONSTITUENTS
Advances in instrumental sophistication have enabled simultaneous or rapid successive multiple determinations to become commonplace, particularly with metals. Neutron activation analysis methods have been reported more frequently although the hardware is rare in the average laboratory. Atomic absorption techniques are now so commonplace that minor innovations hardly merit publication. The speed of species measurement has increased so vastly that sample preparation is now the time factor. Hamilton, et al. (445) used radioactive tracers to establish ashing losses for As, Na, Sr, and Zn a t various conditions of temperature and matrix. Zonneveld and Gersons (725) used aqueous aluminum chloride to accelerate an ashing procedure. Atomic absorption spectrophotometry was used by Frey, et al. (SQJ) for Ca, Mg, Cu, Fe, Ni, Co, Zn, Cr, and Mn in beer. Instrumental sensitivities for reactorneutron-activation analysis for more than 65 elements in milk, among other matrices, were given by Yule ( 7 f J ) . Tuchscheerer (685)described X-ray fluorescence techniques for 13 elements in food. Aluminum has been determined in beer by Etian and Rovella (36J) using aluminon reagent and in ascorbic acid along with Na, Cu, Cr, and Sb using neutron activation analysis by Nagy, et al. (625). This latter method was used by Kirchmann and Roderbourg (475) to measure As in vegetables.
Atomic absorption after ion exchange gave Ba and Sr levels in maize meal and flour for Strasheim, et al. (665). Colorimetric methods for boron determination are reviewed by Truhaut et al. (67J). The use of a Ca ion sensitive electrode for ion estimation in milk was reported by Demott (285). Smith, et al. (635) published an automated procedure for Ca using Eriochrome blue SE, and an automated atomic absorption method for Cu, Zn, and Mg in animal feeds appeared by Roach, et al. (685). Micro amounts of cupric ion in ashes of vegetable material were separated and determined spectrophotometrically after picrate precipitation by Ganchev and Dimitrova (405). Copper has been analyzed in tomato extracts polarographically by Allan, et al. (25),in oils colorimetrically directly by Labuza and Karel (485) and, using neutron activation analysis, in hydrogenated fat by Hogdahl and Melsom (465), in potato tissue by Brown, et al. (14J), and in milk by Samuelsson (595). Chioffi and Osti (185)utilized colorimetry with 2,2’biquinolyl for Cu in brandy. Copper has been selectively extracted from ash solutions with lead dibenzyldithiocarbamate in a paper by Dittel (305). Lead added to canned fish in 0.1 ppm increments was recovered by Bionda, et al. (75) using atomic absorption after a dithizone extraction. Lead 212 was used as a tracer to follow the recovery of lead from food in a dithizone method by Bogen and Kleinman (1OJ). Differential oscillopolarography provided sensitive detection of P b in vegetable matter for Kangniot (535). Lithium in wine, and magnesium in plant Kjeldah1 digests were measured by Amati, et al. (SJ) and Collier (215), respectively, using atoniic absorption. Activation analysis on dairy products provided sensitivity for manganese to the partsper billion level for Das, et al. ($45). Spectrophotometric Mn methods for food reported were that of Firbas, et al. (385) as permanganate, of Chopra, et al. (19J) as ,V,N,N’,N’-tetrakis- ( 2 - h y droxypropy1)-ethylenediamine complex, and of Dittel (295) as diethyldithiocarbamate complex. Mercury was determined in fish and eggs by cold vapor absorption of a mercury spectrum by Pappas and Rosenberg (665). Underdal used activation analysis for Hg in egg (69J) and pork and pig liver (705). This measurement was also performed by Das, et al. (235)after potato flour irradiation and HgS precipitation. Eschnauer (345) analyzed for nickel in wine by polarography. Smith, et al. ( 6 2 4 reported an automated flame photometric potassium analysis for tea. Sodium sensitive electrodes were used by Halliday and Wood (435) to measure salt in bacon and Ka ion in hen egg yolk by Richardson (675). Strontium methods for milk by flame
photometry were described by Brandt, et al. ( I S J ) , and Goodall (415) and Hingorani, et al. ( 4 5 4 cited neutronactivation analysis. Among anion and nonmetal methods, Souliotis ( 6 4 4 employed radioactivation to determine chlorine in beer while Barberio (6J)measured iodine in vegetables. A new method for nitrite in cheese was reported by Lembek, et al. ( 5 0 J ) . Results for flame spectrophotometric measurement of phosphorus were given in a paper by Skogerboe, et al. (61.7). Color formation provided sensitive method for quantifying P in lipids for Black and Hammond ( 8 J ) , and in photodensitometrically measured polyphosphate TLC and paper chromatography spots for Covello and Schettino (ZM). Phytin extracts from rice flour were titrated amperometrically into a lead nitrate solution by Babakhodzhaeva, et al. (55). A satisfactory shorter combustion time is reported in a method for total sulfur by Chaudhry and Cornfield ( 1 7 4 . Radioactive element methods while less frequently reported for food since the cessation of most atmospheric nuclear testing, are still appearing. Boni (11J) described a rapid ion exchange potassium cobalt ferrocyanide column procedure for caesium-137. Petrow and Levine ( 5 6 4 claimed that substitution of ammonium cobalt ferrocyanide provided a cleaner spectrum. Hahn, et al. (4gJ) used ammonium molybdophosphate in a rapid column method. Radioactive iodine in milk is precipitated and counted after organic decomposition in Tanaka’s method (66J) while it is adsorbed initially on a AgCl column in a method by Fairman and Sedlet (87.4. Eakins and Brown ( S 1 J ) simultaneous counted iron-55 and iron-59 by liquid scintillation. Spontaneous deposition of lead-210 and polonium-210 on nickel disks before counting provided the basis for an analysis in foods for Blanchard ( 9 J ) . Liquid scintillation counting after solvent extraction permitted phosphorus-32 measurement in foods for Ellis, et 61. ( S Z J ) . Davis ( M J ) discussed strontium-90 determinations in food. Lopez and Krebs (515) described procedures for sampling canned food headspace. Electrodes were used to measure oxygen dissolved in oils during nitrogen purging by Aho (1J)and oxygen in cider and fruit juices by Burroughs (15J). Carbon dioxide has been titrated in nonaqueous media after absorption by Braid, et al. (12J),and determined along with ethanol in beer using GLC on Porapak Q in a paper by Silbereisen, et al. (6U.J). Free and combined sulfur dioxide in wine and grape juice were nitrogen swept a t different temperatures and titrated in trapping solutions by Deibner, et al. (27J). Sulfur dioxide trapped in a mercuric
complex was polarographically measured by Ciaccio and Cotsis (2OJ). Carruthers, et al. (16J) used rosaniline to analyze for sulfur dioxide in sugar solutions. Free and combined HCN in wine and grape juice were swept out a t different conditions and reacted as cyanide ion with pyridine-barbituric acid by Deibner and Bardou (264. Hydrogen sulfide in wine was swept over in hydrogen and titrated with cadmium in a method of Eschnauer and Tolg (36J). Amin and Olson (4.J) and Lechner and Kiermeier ( 4 9 4 reported on hydrogen peroxide in milk. A test paper for estimating this compound in noodles was prepared by Ogawa, et al. ( 5 4 4 . Erdey, et al. (3SJ) employed luminol as a fluorescent acid-base indicator. MOISTURE
Determining the amount of moisture in foodstuffs is undoubtedly one of the most important and often performed analyses performed by the food analytical chemist. Moisture in food is important from the standpoint of quality, shelf life, and consumer value. It is also one of the more frustrating analytical challenges because the nature of water in foodstuffs is generally not well defined or clearly understood. Hence, we find in the literature increasing concern with “free” and “bound” water and also with the effect that environmental moisture has on foodstuffs. Beary (ZK) gives a bibliography containing 380 references on moisture equilibrium in relation to the chemical stability of dehydrated foods, and Labuza ( 6 K ) describes sorption phenomena in foods and compares the use of three sorption isotherms for determining moisture equilibrium data. Loncin, et al. ( 7 K ) reports on the influence of water activity to the spoilage of foodstuffs and describes a method of evaluating water activity as a function of water content. Changes occurring in the bound water of fish meat during processing were followed by Oshima (11K) using ethylene glycol as a solvent for determining “free” water. Toledo, et al. (16K) report on a quantitative NMR method for determining bound water in wheat flour and dough, and Qaraf, et al. (14K) report on the effect of electrolytes on determining moisture by NMR. Young and Nelson (17K) describe a hysteresis found between the sorption and desorption isotherms determined for wheat and present equations and an explanation for this occurrence, and Miller (10K) reports on a microcentrifuge procedure for determining the water-retention properties of wheat flour. A collaborative study was made ( 9 K ) of oven methods for determining moisture on roasted ground coffee and comparisons were also made of basic moisture methods on eleven food products
(1K). Strange (15K) reports the results of a comparative study of methods for the determination of moisture in cheese, and Ince and Turner describe a microwave-attenuation technique for determining the amount of moisture in plain cake (4K). Palotas, et al. ( I Z K ) compare oven drying with the acetyl chloride method for determining moisture in ground paprika. A procedure is given for computing and determining the solids in syrups and beverages formulated with medium invert sugar from apparent Brix values (8K), and a rapid method for estimating moisture by refractive index ( S K ) is described for dried fruits (16 to 30y0 moisture). Rader (1SK) reports on results of a collaborative study which compares Karl Fischer and near infrared moisture results with vacuum-oven data for dried vegetables and spices, and Kliman, et al. ( 5 K ) make use of near infrared to determine the amount of water in butter oil. ORGANIC ACIDS
Most separation and measurement methods for food organic acids are classically wet in nature-&?., column, paper, and thin-layer chromatographyprimarily because of the nonvolatility and polarity of polyfuiictional acids. However, in cases where appropriate derivative formation is sufficiently easy and quantitative, the superior resolving ability of GLC has been utilized. Carles (101,) described an automated determination of organic acids after column chromatography using phenol red decolorization from pH changes. Fruits and vegetables have been frequently investigated with respect to their acids. Abdurazakova, et al. (1L) used ion exchange followed by paper chromatography to identify acids in seven pomegranate variety juices. Amon and Markakis (ZL) used ion exchange, paper, and thin-layer chromatography, as well as other tests to identify thirteen acids in Concord grape juice. Lindner and Jurics (S6L) sprayed spots on paper chromatograms with Schweppe reagent and measured the fruit juice acids densitometrically. Bellucci, et al. (4L) reported changes in citric and malic acids during tomato ripening. de Moura (16L)employed ion exchange and paper chromatography to investigate the nonvolatile acids of prunes. Fernandez-Flores, et al. (2UL) reported collaborative results for a polarimetric method for I,-malic acid in fruit. Fumaric acid was determined in a revised polarographic procedure for foods by Taylor, et al. (48L). Mazliak (38L) separated apple pulp acids by GLC of their methyl esters. Hautala (2SL) also employed methyl esters of fruit acids to enable gas chromatographic partition to occur. He later ) this separation for reported ( 2 4 ~ on VOL. 41, NO. 5, APRIL 1969
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additional fruit acids. Li and Woodroof (35L) analyzed peaches for nonvolatile acids, also using GLC of methyl esters, but after an initial isolation as lead salts. Silica gel chromatography was employed by Mori, et al. (4OL) to investigate organic acids in nine fruits. Kolesnik, et al. (S1L) determined changes in apple organic acids during storage and Johnston, et al. (98L) reported on nonvolatile acids in fifteen species of fruits and vegetables. Cynarin, chlorogenic, and caffeic acids were visualized with a silver nitrate reagent to permit detection after TLC of vegetable and fruit juices by Colombo (fSL). Davidek, et al. (14L) described a method for separating chlorogenic acid from plant extracts before nitrous acid reaction and subsequent polarography. Chlorogenic acid, along with ascorbic acid and (+)-catechols was determined in apples by differential spectrophotometry in a paper by Delaport and Macheix ( f 5 L ) . Dranik (17L) reported six phenolcarboxylic acids in artichoke. Eistert described several quantitative methods for chlorogenic acid (18L) and also reported on its levels in green and roasted coffee (19L). Lehmann, et al. (SSL) published a quantitative TLC method for chlorogenic acid in coffee. Isomeric chlorogenic acids have been separated using TLC (21L). Nakanishi (41L ) identified the structure of isochlorogenic acid from Brazilian coffee beans by NMR spectrometry. Apples were studied by paper chromatographic techniques by Macheix (S7L) and showed a particular abundance of chlorogenic acid. Jurics, (29L) also using paper, showed good detectability for caffeic, chlorogenic and ferulic acids in foods. Milic, et al (S9L) effected isolation by column and identification by paper chromatography for chlorogenic and quinic acids in sunflower meal. Bruemmer (5L) described TLC techniques for monobasic acids of up to eight carbons. He later detailed systems for multibasic acids (6L, 7 L ) particularly those found in the baking industry. A comparison of methods for lactic acid in bread was reported by Bruemmer and Klempin (8L). Johnson ( W L ) showed that tartrate in baking powder could be determined by differential spectrophotometry. Schormueller and Schubert (46L) used TLC to examine bread and cake samples for fumaric to maleic acid isomerization. The fixed acids in wine were gas chromatographed as their trimethylsilyl derivatives by Brunelle, et al. (9L). Lehmann and Martinod (S4L) used cellulose TLC for white wine nonvolatile acids. Clauss, et al. (I2.L) and Schormueller, et al. (45L) investigated mucic acid in wine. A precipitate in loganberry wine was shown to be largely ellagic acid by spectrometric methods by Singleton, et al. (47.L). Arkima (SL)
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ANALYTICAL CHEMISTRY
analyzed beer for relative amounts of volatile acids and found over sixteen of them. Hautke (d6L) determined a and @ acids in hops by GLC. (Y and is0 (Y acids in hops and beer were separated on paper strips before extinction measurement by Verzele, et al. (5OL). -4liquid-liquid chromatographic procedure was proposed by Chobanov, et al. (1IL) for citric acid and its thermal decomposition products in vegetable oils. Ohlson, et al. (4SL) determined citric acid in fats by a nonaqueous titration. Propionic acid was measured in foods as its ester by Grosjean, et al. (2%). Hempenius and Liska (96L) used steam distillation and GLC to analyze for volatile short chain acids in dairy products. Free and esterified fatty acids in cheeses were converted to methyl esters and studied by GLC by Kuzdzal, et al. (S2L). Klocking, et al. (SOL) classified the brown pigment in roasted coffee extracts as humic acid. Free and combined acids in chicken bones were determined by silica column chromatography after ion exchange by Nobuhara (42L). Osada and Goto (44L) tabulated changes in organic acids in baby clams during storage. Dehydroacetic acid was effectively determined in the presence of other food additives in a new colorimetric method by Yamamoto, et al. (5f.L). Thompson and Hedin (49L) used TLC of the 2,4-dinitrophenylhydrazide derivatives of organic acids to achieve separation. Zagrodzki, et al. (5%) separated sugar industry acids on ion exchange paper they had prepared. PROTEINS, A M I N O ACIDS, A N D NITROGEN
Interest in the analysis of protein in foods continues to lie in studies of methods for total protein and of methods for the fractionation of the native protein of foods. Barley proteins have been separated by Brown, et al. (1OM) using disc electrophoresis with polyacrylamide gels. Obara, et al. (44M) have fractionated water extractable soy bean proteins on a Sephadex G-200 column. Dye-binding has been applied to the determination of total protein in milk by Jain, et al. (29M) using Amido black 1OB and by Ashworth ( S M ) to dairy products using Orange 12 and Orange 10. Twenty-three dyes were studied by Tsugo, et al. (67M) for the estimation of protein in milk and Orange 7, Orange 65, and Green 25 were judged to be most suitable. Decio (16M) has described a refractometric method for protein in milk using the difference between the n of whole and deproteinized milk as a measure of the total protein. Milk protein has been fractionated after dye binding with Orange G and the different fractions determined colorimetrically by analysis
of the filtrate (74M). A chapter on milk proteins is included in “Advances in Protein Chemistry,” Vol. 22 ( d M ) . A colorimetric method for proteosepeptone in milk has been proposed by Ganguli, et al. (f9M) using the FolinCiocalteu reagent. Sephadex filtration a t low temperatures has been applied to acid casein and skim milk by Yaguchi, et al. (72M). Wheat flour proteins have been separated by disc electrophoresis on polyacrylamide gels of rectangular cross section ( 4 S M ) , by ion-exchange chromatography after extraction with buffers (14J4), and by gel chromatography on Sephadex G-100 with ion-exchange chromatographic examination for the amino acid content of the hydrolyzed fractions (7OM). Various types of extractions of wheat proteins have been studied by Jankiewicz, et al. (30.11, S f A f ) , using gel filtration, gel electrophoresis and sucrose gradient ultracentrifugation. Ion exchange separation on sulphoethylcellulose has been applied by Huebner and Wall (28121) to gliadin proteins. Sulfuric acid-hydrogen peroxide digestion has been used by Roberts, et al. (49.11) for the micro-Kjeldahl determination of the nitrogen content of edible fats. O’Hara (45M) has investigated the effect of reducing sugar on the biuret reaction. Casein and sodium caseinate have been separated from meat products using the selective solubility of casein in sodium oxalate ( 4 J f ) . Heterometric titrations have been using studied by Bobtelsky, et al. (QM) heteropoly acids as titrants for gelatin and egg albumin. Gas chromatography has been applied to the analysis of p-alanylhistidine dipeptides by Carisano (125f) after hydrolysis and formation of the N-trifluoroacetyl derivative of p-alanine. Gas chromatography of low temperature pyrolyzates of proteins has been described by Stack (6SlU). Mass spectrometry has been used as a means of determining amino acids sequences in peptides by Senn, et al. (57df), by Shemyakin, et al. (58iIf), and by Biemann, et al. (&If). A microenzymic method for the analysis of acetyl groups in proteins and peptides has been described by Stegink (6451). Amperometric titration for sulfhydryl groups has been described by Hanim, et al. ( I S M ) ,and potentiometric titration using silver nitrate by Kiermeier, et al. (8SiIf). Sulfhydryl and disulfide groups have also been determined by spectrofluorimetry using fluorescein mercuric acetate ( 6 8 M ) ,by colorinietry with 2,3dichloro-1 ,Cnaphthaquinone (27-11), by disulphide exchange after borohydride reduction with 3,3’-dithiobis-(6-1ntrobenzoic acid) ( I S X ) , and by reaction with N-ethylmaleimide (22111). A modified Van Slyke Method using
decarboxylation with ninhydrin has been described by Schenk, et al. (5SM) for the determination of a-amino nitrogen. The Folin phenol reagent in the presence of divalent cobalt has been proposed by Matsushita, e t al. ( S 8 M ) as a colorimetric method for the estimation of amino acids and peptides. Volatile amino acid derivatives prepared as the N-trifluoroacetyl derivatives have been studied for amino acid determination by Blau, et al. ( 7 M ) using gas chromatography with gas density detector and by Gehrke and Stalling (2011) on a dual column with a differential flame ionization detector. Clarification by means of dialysis and ion exchange chromatography has been used by Satterlee, et al. (52M) before gas chromatography of the butyl N trifluoroacetyl derivatives. Procedures for preparing the trimethylsilyl derivatives of amino acids for gas chromatography have been described by Smith, et al. (60M), and by Ruhlmann, et al. (50.11). Seventeen amino acids and ten peptides have been analyzed by Merritt, et al. (S9JI) using a technique combiningpyrolysis gas chromatography and mass spectrometry. A polyacrylamide gel has been found useful for desalting proteins, peptides, and amino acids (55M). Recent advances in ion exchange chromatography are reviewed ( 2 l M ) . Studies of ion-exchange chromatographic separation of amino acids as a function of pH and acetate buffer concentration have been carried out by Kurahasi, et al. (S5M). Two dimensional thin-layer chromatographic separation of amino acids has been describd by Bujard, et al. ( 1 l M ) . Paper chromatographic separation of amino acids has been improved by use of buffered paper a t pH 12 (f7-41).A simple quantitative method for amino acids described by Heathcote, et al. (26M) uses spotting of the paper chromatogram with cadmium acetate and ninhydrin, eluticn of the spots, and colorimetry. New reactions for amino acids on paper chromatographs using isatin and metal salts have been discussed by Morozova (41M). Ninhydrin with collidine, followed by ethaiiolic potassium hydroxide has been used by Stubchen-Kirchner (65-11) as a means of differentiating amino acids. Many methods have been described for specific amino acids. Pelletier (47211) has determined cystine as cysteic acid after paper electrophoresis. Lysine has been determined by the reaction with fluorodinitrobenzene and chromatographic separation and polarographic determination (8M),by reaction of its copper salt with fluorodinitrobenzene (56M), and by its reaction with chlorodinitrobenzene (51M). A rapid hydrolysis procedure for the preparation of samples for lysine determination has been described by Kohler, et al. (34M). Buffer a t p H 4.32 is used by Skodak,
et al. (59M) to separate S-methyl-
methionine from lysine. A procedure for the separation of prolines and hydroxyprolines by gas chromatography has been described by Mussini, et al. ( 4 2 ~ ) .Selenocystathione has been extracted, separated by ion-exchange chromatography and determined by activation analysis for selenium (46M). Tryptophan has been determined colorimetrically by reaction with xanthydrol (69M), in cereals by reaction with pdimethylamino-benzaldehyde (40M), and by its reaction with 5,5’-methyleneA special di-(Z-furaldehyde) ( I M ) . purification for tryptophan is described by Barman, e t al. ( 5 M ) , and pronase hydrolysis is used to solubilize corn proteins for tryptophan determination (62.V). Tyrosine has been determined colorimetrically by Sweeney, et al. (66M) using ion exchange to remove interferences. -4method for neuraminic acid in milk using thiobarbituric acid was proposed by Kiermeier, et al. ( S Z M ) . Gasometric analysis, similar to the Van Slyke method, has been described for hexosamines and free amino acids by Deibner, e t al. (16M). Electrophoresis on silica gel has been used to separate histamine and histidine (37M). A fluorimetric method for histamine and serotonin in milk described by Zarkower, el al. (7SM) uses anion exchange to purify the extract and the reaction of histamine with ophthalaldehyde for measurement. Methods for nucleosides and heterocyclic bases in peas have been described by Schormuller, et al. (54‘11). Amino compounds, including amino acids, may be spotted on paper chromatograms using diazotized 4-nitroaniline and sodium carbonate solution (48M). Gas chromatography on polymer beads has been used to separate simple aliphatic and Feibush, et al. (18M) amines (61114)~ have used optically active stationary phases to separate primary amines by gas chromatography. Wheaton, et al. (71iM) have described analysis of phenolic amines using ion-exchange chromatography. Colorimetric procedures for volatile amines using ninhydrin have been described by Harada, et al. (25M). The same reagent has been used for primary amines by Hantzsch, e t al. (Z4M). Direct amperometric titration of amines with sodium tetraphenylborate solution has been studied by Lu, et al. (S6M). VITAMINS
The innovations evident since the last review, although far from radical in vitamin methodology, are consistent with the general trend in analytical chemistry. T h a t is, more and more chromatographic separations are being utilized to approach the unequivocal measurement of a species. Vecchi and
Kaiser (62.V) subjected ascorbic acid to gas chromatography for measurement after formation of its trimethylsilyl derivative. Microgram amounts of ascorbic acid were determined on a starchiodine impregnated paper chromatographic technique by Uchman (59N). Schmandke and Gohlke (60N) used a thin-layer separation to measure L- and dehydroascorbic acid in foodstuffs. Ascorbic acid derivatives and nitrites in pickling mixtures were determined simultaneously by chemical methods by Spanyar, et al. (56Ar). Schorderet, et al. (62N) colorimetrically assayed for ascorbyl palmitate and stearate in fats. The determination and changes of free and bound vitamin C in potatoes were discussed by Fuertig and PohloudekFabini (15N, 42N, 16N). Fischer, et al. (12N) reviewed factors effecting the 2,6-dichlorophenolindophenol routine titration. Deutsch and Weeks ( 6 N ) reported a microfluorimetric ascorbic acid procedure. Schillinger (49N) commented on relative vitamin C stability in wild and cultivated bilberries. The tocopherols as a group have received widespread attention from chromatographers. Blattna, et al. (IN) used TLC on alumina to separate them from interferences followed by a colorimetric determination. Jaky ( W N ) used TLC on Kieselgel G with his solvent system chosen for either total or individual tocopherols. Tocored and its relationship to water content and soybean oil color reversion was explored with a TLC technique by Komoda, et al. (26N). Column chromatography followed by Silica Gel G TLC yielded three cereal tocopherol fractions for Lindberg ( S I N ) . Ergocalciferol and cholecalciferol esters were purified by chromatography in the dark on several thin-layer materials by Pasalis and Bell (S9N). Alumina-gypsum plates separated vitamin D from A before antimony trichloride colorimetry for Petrova, et al. ( 4 I N ) . Maximum separation of a and p tocopherols was reported for several TLC systems by Roughan ( 4 8 N ) . Sturm, et al. (57N) used the Tsen spectrophotometric method after chromatography. Tsugo, et al. (58.h‘) separated a, p, y and 6 tocopherols in milk. Two dimensional TLC enabled Whittle and Pennock (64N) to also separate these four. Eisner, et al. (ION) tentatively identified three series of alcohols, employing a GLC separation after Florisil fractionation of vegetable oil and butter unsaponifiables. Ishikawa and Katsui ( 2 2 N ) acetylated tocopherols before gas chromatography with good recoveries. Slover, et al. (55N)formed the trimethylsilyl derivatives to detect several tocopherols in vegetable and oil samples. Vitamins DPand D3 were differentiated by GLC after antimony trichloride VOL. 41, NO. 5, APRIL 1969
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conversion to isovitamins by Murray, et al. ( 3 4 N ) .
Dicks-Bushnell (7.47) reported several chromatographic columns useful for food tocopherol analysis. The influence of tocopherols in heated fats and oils was investigated by Schmidt (51N ) and Vioque, et al. (63N) reported an anomaly in analyzing for them in autoxidized fats. Searles and Armstrong ( 5 4 N ) modified the Emmerie-Engel procedure for vitamin E in butter and Ikeda, et al. ( f 9 N ) reported an improved assay for it in fish. Paper chromatography and photodensitometry allowed detection of vitamin E in sunflower oil by Rlalysheva (32N), A polarographic procedure was said to be applicable to foods by Wisser, et al. (65N). Tocopherols have been measured in flour by Frazer and Lines (13N), vegetable oils by Gracian, et al. ( f 7 N ) ,and fish by Pawar, et al. (4ON). As with many other food constituents present in trace quantities, the B-group vitamins show an increase in the number of instrumentally facilitated determinations. Prosser and Sheppard (46N) demonstrated the feasibility of niacin analysis by preparing and gas chromatographing ethyl nicotinate, nicotinamide, and N-ethyl-nicotinamide. Nadkarni (35N) described a cyanogen bromide method modification for nicotinic acid in vegetables. Christianson ( 3 N ) determined nutritionally unavailable niacin in corn through cation exchange nonadsorption. Barbiroli ( I N ) investigated the conversion of trigonelline to nicotinic acid in toasted foods. B-group vitamins separated on TLC plates were measured by UV reflectance spectrometry by Frodyma and Lieu ( I 4 N ) . Kaderavek, et al. (Z4N)assayed cheese for vitamins B1 and B2 using a spectrophotofluorimetric method. Knobloch (25“ used a fluorescence change after photoreduction to analyze for riboflavine. Riboflavine and its photolytic decomposition products were retained on cation exchanges for Koziolowa (2QN) and formed the basis for a method in food (SON). Koziol, et al. (28N) compared various extraction and measurement methods for riboflavine in wheat. hfaslowski used paper strip chromatography to separate flavine nucleotides (33N). Ostrowski, et al. ( 3 7 N ) isolated an egg riboflavine flavoprotein. A modified standard fluorimetry procedure with supplementary hydrolysis was employed by Fel’dman, et al. (IfiV). Pyridoxine mas determined in natural products by the fluorescense of its lactone by Schulz, et al. ( 5 3 N ) . Other Be vitamins have been analyzed by gas chromatography as trifluoroacetyl esters by Imanari and Tamura (2ON) and as isopropylidene and acetyl derivatives by Korytnyk, et al. ( 2 7 N ) . Richter, et al. (47N) investigated the GLC and mass spectrometry of Be trimethylsilyl derivatives. Thin-layer separations of 78 R
ANALYTICAL CHEMISTRY
vitamin Blz and its analogs have been reported by Popova, et al. (43NJ44N). Covello, et al. ( 5 N ) used photodensitometry of TLC plates after B12 separations. Harding (18N) described a solvent front detector for more reproducible B12 paper chromatography in the dark. Parrish (38N) discussed the AOAC chemical method for vitamin A. Usher, et al. (60N) reported details and collaborative results on a method that used a magnesia chromatography step to separate a and 0 carotene in margarine. Vecchi, et al. ( 6 f N ) published GLC and mass spectrometric data on the trimethylsilyl ethers of vitamin A and some isomers. Retinol (and calciferols) were separated by TLC by Richter and Ropte (46N). Vitamin PP in wheat grain and flour was determined by Ionescu-Stoian ( 2 f N ) using photometric and microbiological techniques. The vitamin-P factors rutin, hesperidine, and naringin in orange juice were separated by TLC and subsequently extracted into methanol to measure their extinctions by Drawert, et al. (8.V). Capillary columns of methylated Sephadex were recommended for the liquid chromatographic separation of vitamins K2(40) to K ~ ( I oby ) Nystrom and Sjovall (36N). TLC systems for separating lipoquinones were described by Egger and Kleinig (9.V). Vitamins K5 and K3 were simultaneously determined by GLC after unoxidized K5 was converted to its trimethylsilyl ether, but Cornelius and Yang ( 4 N ) only recovered 44% by extraction from carrots. MISCELLANEOUS
The changes in the official methods of analysis of the AOAC ( f 3 P )have been published and include many foodpertinent procedures. Cameron (W) has listed applications of the ATR infrared method to food analysis. Eisenbrand ( 8 P )reviewed fluorimetry in food chemistry. Kohn (15 P ) discussed the use of infrared analysis for food and he and coworkers (16P) also discussed the near-IR in the same context. A German publication (24P) dealt with many papers presented a t a meeting that have analytical significance for the food industry. Similarly, a more specialized meeting about coffee (82P)had many analytically oriented presentations. The determination of caffeine and other natural alkaloids in foods has appeared in diverse methods. Chiantella (3P) together with Licastro (4P) have used “dead stop” titrations for caffeine analysis in coffee and tea. Danek, et al. (7P),and Zawadzka, et al. (2W) used an iodine precipitation method followed by a titration. Ferren (QP) described a differential spectrophotometric method for caffeine. John-
son (12P) reported the results of a modified Levine method collaborative study. Theobromine and allied alkaloids were determined by Hadorn, et al. (ffP),and Kleinert, et al. ( f d P ) , and Senanayake, et al. ( f 9 P )used this index to estimate nonfat cocoa solids in products. Piperine in pepper was measured colorimetrically by reaction of the methylenedioxyphenyl group by Graham (fop). Automatic analysis of beer was used to estimate beer bitterness as isohumulones by Pinnegar ( f 8 P ) , while Dalgliesh (6P) analyzed humulones and lupulones as their trimethylsilyl derivatives using GLC. Covello, et al. (5P) used paper and TLC to identify and determine quaternary animonium antifermentives in foodstuffs.
LITERATURE CITED Additives
(1A) Alessandro, A,, Zndustrie Agrarie 5, 111 (1967); Anal. Abstr. 15, 3606 f~l R-A~ R \- - , .
(2A) Amano, T., Kanomata, K., Takeuchi, T., Yoshii, H., h’ippon Shokuhin Kogyo Gakkaishi 14, 499 (1967); Chem. Abstr. 6 9 . 7 5 6 3 6 ~11968). (3A). Aoki,’ hl., Yata, N:, Hiromichi, S., hIimura, I., Archs. Pract. Pharm. 36, 9 (1966); ilnal. Abstr. 14, 3553 (1967). (4A) Balakhontseva, V. N., Poltinina, R. 11..Zh. Analit. Khim. 20, 739 (1965): Anal. Abstr. 14, 742 (1967). (5A) Bares, RZ., Prumysl Potravin 17, 375 (1966); Anal. Abstr. 14,5720 (1967). (6A) Brandenbnrg, G., Rohleder, K., Deut. Lebensm. Rundschau 64, 71 (1968). (7A) Braun, G., Hieke, E., 2. Lebensm.L’ntersuch.-Forsch. 130,273 (1966). (8A) Cantagalli, P., Piazzi, S. E., Riparbelli, G., Boll. Lab. Chim. Prov. (Bologna) 19, 41 (1968); Chem. Abstr. 6 9 , 4 2 8 0 5 ~ (1968). (9A) Daniels, D. G. H., Martin, H. F., J . Sci. Food Agr. 18,589 (1967). (IOA) Davidek, J., Beriiac, F., 2. Lebensm. Untersuch. - Forsch. 131, 32 (1966). (11A) Davidek, J., Beniac, T., Prumysl Potrauin 16. 425 (1965): Anal. Abstr. 13.7111 (1966). (12A’) Gavidek, ’J., Janicek, G., Davidkova, E., Z. Lebensm.-Lintersuch.-Forsch. 131,345 (1967). (13A) Davidek, J., Kedzierska, A., Janicek, G., ibid., 129,370 (1966). (14A) Ihvies, A. M. C., J . Ass. Public Analysts 4 , 11 (1966). (l5A) Derse, P. H., Dam, R. J. J . Ass. Ofic. Anal. Chem. 49, 1090 (1966). f16A) ilirkes. G. J.. J . Ass. Public ‘ Analysts 3 , ? 3 (1965): (17A) Diemair, W. Postel, W., “Detection and Determination of Preservatives in Foods,” Stuttgart, Germany, Wissenschaft. T’erlagsges, 1967, Chem. Abstr. 68,86276h (1968). (MA) Fazio, T., Howard, J. W., Sandoval, A., J . Ass. Ofic. Anal. Chem. 51, 17 (1968). (19A) Floyd, K. RI., ibid., 50, 1123 (1967). (20A) de Koning, P. J., Elsses, J., de Vries, H., Sed. Melk- en Zuiueltzjdschr. 20, 204 (1966), Anal. Abstr. 14, 7856 (1967). (21A) Ford, 31.A., Analyst 91, 15 (1966). (22A) Fujiwara, &I., Fiijiwara, K., Shokuhin Eiseigaku Zasshi 9, 147 (1968); Chem. Abstr. 69, 42827e (196s).
-
(23A) Galea, J.., Costache, C., Zgiena, W i t c . . 14. 29!) (1965): Anal. Abstr. ,, 14, 1710 (1!)67). (24A) Goslich, I-., Branntweinwirtschaft 107, 261 (1967); Anal. Abstr. 15, 5613 (196s). (25A) Gossele, J. A. W., Srebrnik-Friszman, P., J . Chromalogr. 23, 305 (1966). (26A) Gspahn, H., Giienther, H., Fleischw i h c h a f t 48, 798 (1968); Chem. Abstr. 69,75621m (1968). (27A) Gunther, H., Deut. Lebensm. Rundschau 63,8 (1967). (28A) Hamaguchi, A., Natsrtki, Y., Tanaka, K., Shokuhin Eiseigaku Zasshi 8, 318 (1967); Chem. Abstr. 68, 67808s (1968). (29A) Hamm, R., Schneider, F., Deut. Lebensm. Rzindschau 64,207 (1968). (30A) Hankin, L., J . Ass. Ofic. Anal. Chem. 50,1342 (1967). (31A) Hundlev, H. K., Hughes, D. D., i b i d . , 49, 1180 (1966). (32A) Jones, H. G., Smith, D. &I., Sahasrabudhe, AI., ibid., 49, 1183 (1966). (33A) Johnson, D. E., Nunn, H. B., Briickenstein, S., ASAL. CHEM.40, 368 (1968). (34A) Kamp, W., Pharm. Weekbl. Ned. 101, 57 (1966); Anal. Abstr. 14, 3555 (1967). (35A) Kanno, S., Fukui, S., Nait’o, S., Tani, T., hIurai, A,, Shokuhin Eiseigaku Zasshi 8, 442 (1967); Chcm. Abstr. 68,76977~(1968). (36A) Kanno, S., Wada, Y., Kakaoka, T.. ibid.. 9. 50 (1968): ,, Chem. Abstr. 69; 9798jr (1968). (37A) Kimura, T., Yoneda, ll., ibid., 9, 63 (1968); Chem. Abstr. 69, 97992 (1968). (38A) Kogan, L., Strezleck, S., Cereal Chem. 43,470 (1966). (39A) Kroller, E., Deut. Lebensm. Rundschau 62. 133 119661. (40A) Krokller, E., Fette, Seifen, Anstrichmittel70, 119 (1968). (41A) Kroeller, E., ibid., 70,431 (1968). (42A) Kross, R. D., U.S. 3,396,806 (Cl. 23-230), 04 Jnne 1968. (43A) Lewis. AI, H.. J . Ass. Ofic. Anal. Chem. 51, 876 (1968). (44A) Ludwig, E., Freimuth, U., Sahrung 9,731 (1965). (45A) AIcCaiilley, D. F., Fazio, T., Howard, J. W , , DiC‘inrcio, F. N . , Ives, J., J . Ass. O$c. Anal. Chem. 50, 243 ( 1967). (46A) JIiethke, H., Deut. Lebensm. Rundschau 62, 267 (1966). f47A1 AIunselise. J. J.. Israel J . Technol. 5,223 (1967). (48A) Naeata. Y.. Ando, N., Shokuhin Eiseigalu Zasshi 8, 532 (19b7); Chem. Absfr.68, 86164v (1968). (49A) Xey, K. H., Fette, Seifen, Anstrichmittel69, 794 (1967). (50-4) Siemoller, H. J., Deut. Lebensm. Rundschau 62,76 (1966). (51A) Padmoyo, AI., hliserez, A,, Mitt. Gebiete Lebensm. Hyg. 58,31 (1967). (52A) Pauli, O., Genth, H., Z. Lebensm.Untersuch.-Forsch. 132,216 (1966). (53A) Ilees, l). I., Analyst 90, 568 (1965). (54A) Reinhard, C., Deut. Lebensm. Rundschau 63,151 (1967). (55A) lI., Jr., J . Ass. Ofic. Agr. Chem. 48,543 (1965). (18B) Briski, B., Klepic, Z . , Farm. Glas. 24, 49 (1968); Chem. Abstr. 69, 51020~ (1968). (19B) Brown, R. F., J . Ass. Ofic.Anal. Chem. 50,515 (1967). (20B) Brown, R. F., ibid., 50, 514 (1967). (21B) Brown. R. F.. Aho. A. C.. abid.. 49,576 (1966). (22B) Burnett, J. L., J . Ass. Ofic.Agr. Chem. 48,624 (1965). (23B) Burt, J. R., Murray, J., Stroud, G. D., J . Food Technol. 3, 165 (1968). (24B) Campbell, A. D., Funkhouser, J. T., J . Ass. Ofic.Anal. Chem. 49, 730 (1966). (25B) Carmon, B., Braudo, C., Kanter, M., Int. J . Appl. Radiat. Isotopes 17, 1 (1966); Anal. Abstr. 14,5744 (1967). ~
(26B) Castell, C. H., Bishop, D. M., Neal, W. E., J . Fish. Res. Board Can. 25, 921 (1968); Chem. Abstr. 69, 34755q f 1!)681. (27B) Cerbulis, J., Ard, J . S., J . Ass. Ofic. Anal. Chem. 50,646 (1967). (28B) Chakrabartv, _ . JI. hl., Bandvopadhyay, C., Bhattacharyya, fi., Gayeii, A. K., J . Chromatogr. 36, 84 (1968). (29B) Champagne, J. R., Dissertation Abstr. 28,4611B (1968). (30B) Charro Arias, A., Simal Lozano, J., Villar Nogueira, M. I)., An. Bromatol. ( M a d r i d ) 20, 27 (1968); Chem. Abstr. 69, 66165p (1968). (31B) Chojnicka, B., Roczn. Panst. Zakl. Hig. 16, 545 (1965); Anal. Abstr. 14, 2827 (1967). (32B) Ciiisa, W., D’Arrigo, V., Maini, F., Penna, N., Riv. Ital. Sostanze Grasse 45, 175 (1968); Chem. Abstr. 69, 75739f (1968). (33B) Connell, J. J., J . Sci. Food Agr. 17.329 (1966). (34Bj Cooper, P. J., de Faubert Maiinder, M.J., hIcCutcheon, G. J., Analyst 92, 382 ilQ671 ~ - ~,. - . (35B) Coulter, E. W., J . Ass. Ofic. Agr. Chem. 48,547 (1965). (36B) Croieier, G., Sauveur, B., Ann. Biol. Anim., Riochem., Biophys. 7, 317 (1967); Chem. Abstr. 68, 86230p (1968). (37B) Cuciillu, A. F., Lee, L. S., hIayne, R . Y., Goldblatt, L. A., J . Amer. Oil Chem. SOC. 43,89 (1966). (38B) Davis, N. D., Hayes, A. W., Eldridge, D. W., Diener, ti. L., J . Ass. Ofic. Anal. C k m . 49, 1224 (1966). (39B) Doro, B., Remoli, S., Boll. Lab. Chim. Provinczali (Bologna) 18, 484 (1967); Chem. Abstr. 68, 38306w (1968). (40B) Uugal, L. C., J . Fish Res. Board Can. 24, 2229 (1967); Chem. Abstr. 68,2065~(1968). (41B) Dvorak, J., Hronikova, hl., Prokopova, V., Prumysl Potravin 17, 162 (1966); Anal. Abstr. 14,4266 (1967). (42B) I)worschak, E., Endelyi, E., Ernahrungsforschung 12,417 (1967). (43B) Eppley, R. hl., J . Ass. Ofic.Anal. Chem. 49,1218 (1966). (44B) Eppley, R. M.,ibid., 51, 74 (1968). (45B) Eppley, R. M., Stoloff, L., Campbell, A. D., ibid, 51,67 (1968). (46B) Ettinger, C. L., Malanoski, A. J., Kirschenbaum. H.. J . Ass. OBc. Aar. Chem. 48,1186(1965). (47B) Fedeli, E., Lanzani, A., Riv. Ztal. Sostanze Grasse 44, 127’(1967); Anal. Abstr. 15,3583 (1968). (48B) Ferraris, A,, Oli, Grassi, Deriv. 2, 34 (1966); Chem. Abstr. 68, 86245x ( 1968). (49B) Ferri, S., Pallini, V., PalleranoDomini, I., Farmaco, Ed. Scient. 21, 511 (1966); Anal. Abstr. 14, 7099 (1967). (50B) Finley, J. W., White, J. C., Bull. Environ. Contam. Toxicol. 2, 41 (1967). (51B) Fitelson, J., J . Ass. OBc. Anal. Chem. 50,293 (1967). (52B) Fitelson, J., ibid., 51,937 (1968). (53B) Frank, H., Milchwissenschaft 20, 361 (1965); Anal. Abstr. 13, 6523 (1966). (54B) Frank, H. K., Eyrich, W., Z. Lebensm. - Untersuch. - Forsch. 138, l(1968). (55B) Franzke, C., Heims, K.-O., Sitzki, W., Spernau, S., Nahrung 9, 691 (1965); Anal. Abstr. 13,7142 (1966). (56B) Fraser, D. I., Pitts, D. P., Dyer, W. J., J . Fish. Res. Board Can. 25, 239 (1968); Chem. Abstr. 68, 484192 (1968). 1
VOL. 41, NO. 5, APRIL 1969
79R
(57B) Fredholm, H., Food Technol. 21, 197 (1967). (58B) Freeman, C. C., J . Ass. Ofic. Agr. Chem. 48, 1183 (1965). (59B) Fritz, W., Naturwissenschaften 53, 132 (1966): Anal. Abstr. 14. 4298 (i967j. (60B) Fujii, Y., Uchiyama, II., Ehira, S., Noguchi, E., Nippon Suzsan Gakkaishz 32, 410 (1966); Chem. Abstr. 68,67849f (1968). (61B) Galanos, D. S., Kapoulas, V. M., J . Amer. Oil Chem. SOC.42, 815 (1965). (62B) Gecan, J. S., Brickey, P. &I.,Jr., J . Assoc. Ofic. Anal. Chem. 50, 496 I ,
,.
(,_l_. 1 967 ).
(63B) Gecan, J. S., Brickey, P. AI., Jr., ibid., 51,531 (1968). (64B) Getzendaner, AI. E., Doty, A. E., RIcLaughlin, E. I., Lindgren, D. L., J . Agr. Food Chem. 16,265 (1968). (65B) Grimmer, G., Hildebrandt, Deut. Lebensm.Rundschuu 61,237 (IS (66B) Grimmer, G., Hildebrandt, ibid., 62,19 (1966). (67B) Grimmer, G., Hildebrandt, A., Chem. &Znd., 2000 (1967). (68B) Hammonds. T. W.. Analust 91. ‘ 401 (1966). (69B) Hankin, L., J. Ass. Ofic. Agr. Chem. 48,1122 (1065). (70B) Hansel, G., Wurziger, J., Arch. Lebensmittelhyg. 19, 126 (1968); Chem. Abstr. 69, 75617q (1968). (71B) Hanssen,E.,Sturm, W.,Z.Lebensm.lintersuch.-Forsch. 134,69 (1967). (72B) Helberg, D., Deut. Lebensm. Rundschau 62, 178 (1966). (73B) Hills, P. R., Smith, A. H., Rep. U.K. Atom. Energy Auth., AERE-R 5461, (1967); Anal. Abstr. 15, 4257 (1968) (74B) Hordynska, S., Legatowa, B., Roczn. Panst. Zakl. Hig. 17, 535 (1966); Anal. Abstr. 15,1626 (1968). (75B) Howard, J. W., Fazio, T., White, R. H., J . Ass. Oflc. Anal. Chem. 51, 544 (1968). (76B) Howard, J. W., Fazio, T., White, R. H., J . Agr. Food Chem. 16,72 (1968). (77B) Howard, J. E., Fazio, T., White, R. H., Klimeck, B. A,, J . Ass. Ofic. Anal. Chem. 51, 122 (1968). (78B) Howard, J. W., Turicchi, E. W., White, R. H., Faaio, T., ibid., 49, 1236 (1966). (79B) Hughes, R. B., Jones, N. R., J. Sci. Food Agr. 17,434 (1966). (80B) Huis in’t Veld, L. G., JonkmanVan den Broek, E. B., DeGroot, W. C., Tijdschr. Diergeneesk. 93, 805 (1968); Chem. Abstr. 69, 66218h (1968). (81B) Jayaraman, A., Sreenivasamurthy, lr.,Parpis, H. A. B., J . Ass. Ofic. Agr. Chem. 48, 1256 (1965). (82B) Katz, I., Keeny, M., J . Dairy Sci. 50,1764 (1967). (83B) Kawada, T., Krishnamurthy, R. G., Pllookherjee, B. I)., Chang, S. S., J . Amer. Oil Chem. SOC.44, 131 (1967). (84B) Kessler, H., Rlueller, E., J . Chromatogr. 24,469 (1966). (85B) Kirk, J. R., Hedrick, T. I., Stine, C. M., J . Dairy Sei. 51,492 (1968). (86B) Kleinert, J., Habegger, &I.,Intern. Chocolate Rev. 22,38 (1967). (87B) Kleinert, J., Habegger, &I., ibid., 22,342 (1967). (88B) Kiss, B., Kovacs, J., Gyarmati, Elelmiszervizsgaluti Kozlem. 13, (1966); Chem. Abstr. 69, 26084e (1968). (89B) Kretszchmann, F., Engst, R., Xahrung 12, 135 (1968); Chem. Abstr. 68,103917n (1968). (SOB) Krishnamurthy, R. G., Dissertation Abslr. 27, 79B (1966). (SIB) Krishnamurthy, R. G., Chang, S. S., J . Amer. Oil Chem. Soc. 44, 136 (1967). 80 R
0
ANALYTICAL CHEMISTRY
(92B) Kroeller, E., Deut. Lebensm. Rundschau 62,227 (1966). (93B) Kroeller, E., ibid., 64,6 (1968). (94B) Kurtz, 0’1). L., J. Ass. Ofic.Anal. Chem. 50,521 (1967). (95B) Kurta, 0’1). L., McCormack, T. H., J . Ass. Ofic. Agr. Chem. 48, 554 (1965). (96B) Lapshin, I. I., Rodina, T. G., Izv. Vyssh. Ucheb. Zaved., Pishch. Teknol. (6) 30 (1967); Chem. Abstr. 68, 67844a (1068). (97B) Larry, D., Salwin, H., J . Ass. Ofic.Anal. Chem. 49,681 (1966). (98B) Levi, C. P., Borker, E., ibid., 51, 600 (1968). (9913) Lueck, H., J . Dairy Res. 33, 25 (1966). (100B) Maes, E. E. A., J . Ass. Ofic. Anal. Chem. 49,1176 (1966). (101B) Malanoski, A. J., Greenfield, E. L., Barnes, C. J., Worthington, J. &I.,Joe, F. L., Jr., ibid., 51, 114 (1968). (102B) RIani, V. V. S., Lakshminarayana, G., Chromatog. Rev. 10, 159 (1968). (103B) Mani, V. V. S., Lakshminarayana, G., Indian J . Technol. 3, 339 (1965); Anal. Abst. 14,1079 (1967). (104B) hlarth, E. H., J . MzZk & Food Technol.30,317 (1967). (105B) Xfannelli, G., Ann. Fac. Econ. Commer., Univ. Studi Messina 4, 467 (1966); Chem. Abstr. 68, 48315n (1968). (106B) Martinenghi, G. B., Oli, Grassi, Deriv. 2, 26 (1966); Chem. Abstr. 68, 113447~(1968). (107Bl XIattick. L. R.. Weirs. L. D.. Robinson, W.’ B., J . ‘Ass. Ohc. Anal: ~
Ohem. 50.299 - - - (1967). I
\ - -
(108B) ifjller, B. J., ibid., 48, 1181 (1965). (109B) Miller, A l . T., ibid., 50, 505 (1967). (llOB) Narziss, L., Kieninger, H., Reichender, E., &auwissenszhaft 19, 284 (1966); Anal. Abstr. 14,7147 (1967). (111B) National Academv of Sciences Publication 1354, “Toxicknts Occurring Naturally in Foods,” Washington, D.C., ~
1966.
(li2Bj. Nikkila, 0. E., Kurisi, T., Kytokangas, R., J . Food Sci. 32, 686 (1967). (113B) Osada. H.. Goto, I., Eivo To ‘ Shohuryo 20, 387 (1968); Chem.-Abstr. 6 9 , 1 8 7 1 ~(1968). (114B) Parodi, P. W., Aust. J . Dairy Technol. 22, 209 (1967); Chem. Abstr. 68,94719~(1968). (115B) Pasarela, N. R., Waldron, A. C., J . Agr. Food Chem. 15,221 (1967). (116B) Patterson, R. L. S., Chem. & Ind. 1968,548. (117B) Pearson, D., J . Ass. Public Anal. 5,44 (1967). (118B) Pearson, D.. J . Sci. Good Aor. ‘ 19,357 (1968j . ’ (119B) Pertoldi-Marletta, G., Atti Conv. Reg. Aliment., 1st Conv. Naz. Qual., 4th. Trieste 678 (1965); Chem. Abstr. 38356n (1968). (120B) Peterson, R. E., Ciegler, A., Hall, H. H., J . Chromutogr. 27, 304 (1967). (121B) Pfab, W., Deut. Lebensm. Rundschau 63,72 (1967). (122B) Pfeilsticker, K., Rasmussen, H., 2. Lebensm.-Unterush.-Forsch. 136, 1 (1967). (123B) Pilnik, W., Faddegon, M., Mitt. Geb. Lebensmittelunters. Hyg. 58, 151 (1967); Chem. Abstr. 68, 48439f (1968). (124B) Poapst, P. A., Durkee, A. B., XlcGugan, W. A., Johnston, F. B., J . SciFood Agr. 19,325 (1968). (125B) Pomeranz, Y., Daftary, R. D., Shogren, M. D., Hoseney, R. C., Finney, K. F., J . Agr. Food Chem. 16,92 (1968). (126B) Pons, W. A., Jr., Goldblatt, L. A., J . Amer. Oil Chem. SOC.42, 471 (1965).
(127B) Pony, W. A., Jr., Rohertiori, J. A., Goldblatt, L. A., ibid., 43, 665 (1966). (12813) Poiirtullier, J., Bull. Apic. Znform. Doc. Sci. Tech. 6, 16‘3 (1963); Chem. Abstr. 68,94677e (1968). (129B) Primo Yufera, E., Sanchez Parareda, J., Alberola, J., Hevta Agropuim. Technol. Aliment. 5, 211 (1‘365); Anal. Abslr. 13, 5846 (1966). (13OB) Primo Yufera, E., Royo Iranzo, J., ibid. 5, 216 (1965); Anal. Abslr. 13,5846 (1966). (131B) Primo Yufero, E., Mallent, D., Revta Agroquim. Tecnol. Alzment. 6, 215 (1966); Anal Abstr. 14, 5748 (1967). (132B) Purchase, I. F. H., Steyn, M., J . Ass. Ojic. Anal. Chem. 50, 363 (1967). (133B) Ramamiirthy, M.K., Narayanan, K. M.,Bhalerao, V. R., Dastur, N. N., Indian J . Dairy Sci. 20, 11 (1967); Anal. Absir. 15, 3589 (1968). (134B) Reed, G. L J . Ass. Ofic. Agr. Chem. 48,553 (19t5). (135B) Rentschler, H., Mitt. Geb. Lebensmzttelunters. U . Hyg. 56, 265 (1965); Anal. Abstr. 14, 3 (1967). (136B) Riley, R. C., Prostak, D. J., J . Ass. Oflc. Anal. Chem. 49,903 (1966). (137B) Roaf, A., Brickley, P. &I., Jr., ibid., 51, 518 (1968). (138B) Roos, J. B., Chem. Weekbl. 62, 1 (1966); Anal. Abstr. 14, 2825 (1967). (139B) Sarma, P. S. N., Nithyanandan, V. V., Res. Ind. (A‘ew Delhi) 12, 167 (1967); Chem. Abstr. 69, 58407d (1968). (140B) Satoskar, K. G., Lakshminarayana, G., Kane, J. G., Indian J . Technol. 3, 302 (1965); Anal. Abstr. 14, 431 (1967). (141B) Schilling, J., Zobel, M., Pharmazie 21, 103 (1966); Anal. Abslr. 14, 3577 (1967). (142B) Schuller, P. L., Ockhuizan, T., Werringloer, J., Marquardt, P., Arzneimitiel-Forsch. 17, 888 (1967); Anal. Abstr. 15, 6307 (1968). (143B) Schuster, K., Narziss, L Kumada, J., Brauwissenschaft 20, l2k (1967); Anal. .ibstr. 15,4284 (1968). (144B) Schwien, W. G., Miller, B. J., J . Ass. Ofic. Anal. Chem. 50, 523 (1967). (145B) Scott, P. AI., ibid., 51, 609 (1968). (146B) Scott, P. &I.,Hand, T. B., ibid., 50,366 (1967). (147B) Sieta, F. G., Fette, Saifen, Anstrichmittel 68,314 (1966). (148B) Shotwell, 0. L., Shannon, G. N, Goillden, AI. L., Milburn, hl. S., Hall, H. H., Cereal Chem. 45, 236 (1968). (149B) Silva, C., Contreras, E., Fishing Il‘ews Znt. 6, 44 (196’7); Chem. Abstr. 68,21020a (1968). (150B) Silverberg, H. D., Marchin, J., Morgenstern, W. W., J . Ass. Ofic. Anal. Chem. 49, 820 (1966). (151B) Spanyar, P. Kevei, E., Blazovich, 11..Z. Lebensm.-Untersuch.-Forsch.129, 84 il966). (152B) Spanyar, P., Kevei, E., Blazovich, AI., ibid., 133, 1 (1966). (153B) Stacchini, A., Manzone, A. M., Boll. Lab. Chim. Provinciali (Bologna) 16, 619 (1965); Anal. Abstr. 14, 1696 (1967). (154B) Stein, R., Eisenberg, W. V., Brickey, P. hl., Jr., J . Ass. Ofic. Anal. Chem. 50,519 (1967). (155B) Stein, R., Ferrera, R. S., Brown, It.F., ibid., 49,287 (1966). (156B) Stephens, R. L., ibid., 50, 501 (1967). (157Bi Stoloff. L.. Graff., A.., Rich., H.., ibid:, 49,740 (1966). (l58B) Stoloff, L., Beckwith, A. C., Cushmac. 51,E.. ibid.. 51.65 11968). (l59B) Stone, L. R., ibid, 49, 895 (1966). I-
(16023) Sturm, W., Hanssen, E., 2. Lebensm. - Untersuch. - Forsch. 135, 241) (1967). (161B) Tatmum,J. H., Shaw, P. E., Berry, 11. E., J . ilgr. Food Chem. 15, 773
r., Chen, h L W . H., Zntern. Sua& J . 69.7-4 (1967). ( 1 067 ). (14C) Cokini-Ldkatr., L.. Univ. Studi Trieste, Fac. Econ. Com., 1st Merceol. (162B-j Tengler, H., Farbe Lack 73, 153 No. 27, 1 (1966); Anal. Abstr. 15, 236 (1967); Anal. Abstr. 15,2931 (1968). (163B) Thrasher, J. J., J . Ass. Ofic. (1968). (15C) Commerford, J. D., Scallet, B. L., Agr. Chem 48,545 (1965). Cereal Chem. 42,485 (1965). (164B) Thrasher, J. J., Brickey, .P. M., Jr., J . Ass. Ofic. Anal. Chemasts 51, (16C) Davy, J., Annls Pharm. Fr., 24, 703 (1966); Anal. Abstr. 15, 896 (1968). 525 (1968). (17C) Defrates, J. H., Castle J. L., In(165B) Tilgner, D. J., Food Manuf. 43, tern. Sugar J . 68,173 (1966). 37 (1968). (18C) De Stefanis, V. A., Ponte, J. G., (166B) Tomiyama, T., Kobayashi, K., J . Chromatogr. 34, 116 (1968). Kitahara, K., Shiraishi, E., Ohba, N., (1%) Doesburg, J. J., “Pectic Substances ‘Vippon Suisan Gakkaishi 32,262 (1966); in Fresh and Preserved Fruits and Chem. Abstr. 68,67846~(1968). Vegetables,” Institute for Research on (167B) Tsukuda, N., Amano, K., Xippon Storage and Processing of Horticiiltural Susian Gakkaishi 32, 522 (1966); Produce, Wageningen, The NetherChem. Abstr. 68,67851a (1968). lands, 1965. (168B) Turner, J. C., Clinch, P. G., (20C) Doyle, R. J., Burgan, H. M, Anal. S . Z . J . Sci. 11, 342 (1968); Chem. Biochem. 17, 171 (1966). Abstr. 69,4282413 (1968). (21C) Drawert, F., Kupfer, G., 2. Anal. (169B) Tokunaga, T., Suisancho HokChem. 211.89 (1965). kaido-ku Suisan Kenkyusho Kenkyu (22C) Duttdn, G. G.’S., Gibney, K. B., Hokoku 108 (1964); Chem. Abstr. Jensen, G. D., Reid, P. E., J . Chro68,103968e (1968). matogr. 36,152 (1968). (170B) Uchiyama, H,.Suzuki, T., Ehira, (23C) Fernandez Bertran, J., Xarinello S., Nogiichi, E., Azppon Suisan Gakhlarinello, J., Lloreda Casado, A,, kaishi 32, 280 (1966); Chem. Abstr. Intern. Sugar J . 69,107 (1967). 68,67847d (1968). (24C) Figge, K., Ezperientia 22, 767 (171B) l’azquez, A. W.,Gecan, J. S., (1966); Anal. Abstr. 15,806 (1968). J . Ass. Ofic. Anal. Chem. 51,527 (1968). (25C) Franken-Luykx, J. 34. >I.,Klopper, (172B) l.ogl, K., Schumann, G., Mschr. W. J., Brauwissenschaft 20, 173 (1967); Brazc. 20, 124 (1967); Anal. Abstr. Anal. Abstr. 15,4285 (1968). 15,3604 (1968). (26C) French, D., Robyt, J. F., Wein(1732) Watts, J. O., Holswade, W., J . traub, M., Knock, P., J . Chromatogr. Ass. Ofic. Anal. Chem. 50,717 (1967). 24,68 (1966). (174B) Westoo, G., Acta Chem. Scund. (27C) Friedemann, T. E., Witt, N. F., 20,2131 (1966). Neighbors, B. W., Weber, C. W., J . (175B) White, It. H., Howard, J. UT., ,Vutrition 91, (Suppl. 2) 1 (1967). J . Chromalogr. 29, 108 (1967). (176B) Wierzchowski, J., Fuks, T., Mitt. (28C) Garofalo, E., Minerva Pediat. 18, 1424 (1966); Anal. Abstr. 14, 7634 Lebensmittelunlers. Hyg. 58, 266 (1967); (1967). Chem. Abstr. 69, 1889h (1968). (29C) Garrett. E.. Blanch. J.. ANAL. (177B) Wiley, hI., J . Ass. Ofic. Anal. ‘ CHEM. 39, 1109 (1967). Chem. 49,1223 (1966). (30C) Graham, H. D., J . Food Sci. 32, (l78B) Withirigton, 1). F., Analyst 92, 489 (1967). .. ,. 705 (1967). (31Cj Gunther, H., Schweiger, A., J . (179B) Wright, R. G., J . Ass. Ofic. Anal. Chromatogr. 34,498 (1968). Chem. 50,499 (1967). (32C) Halpern, Y., Houminer, Y., Patai, (180B) Wyler, O., Siegrist, J. J., Mitt. S.,Analyst 92,714 (1967). Geb. Lebensmzttelunters. U . H y g . 56, (33C) Hill, S., Rundell, J. T., ibid., 90, 4 (1965); Anal. Abstr. 14 3 (1967). 681 (1965). (34C) Huber. C. X.. Scobell. H.., Tai., H.., Ceieal Chem. 43,342 (1966j. (35C) Jantzef, F., Potter, A. L., J . Carbohydrates Amer. SOC.Sug. Beet Technol. 13, 218 (1965); Anal. Abstr. 14,2229 (1967). (IC) Anderbon, D. R1. W., Stoddart, (36C) Jonsson, P. Samuelson, O., J . J. F., Carbohydrate Res. 1,417 (1966). Chromatogr. 26, 194 (1967). (2C) Aspinall, G. O., Hunt, K., hlorrison, (37C) Kesler, R., ANAL.CHEM.39, 1416 I. M.,J . Chem. SOC.Sect. C, Organic, (1967): 21, 1945 (1966). (38C) Kim, Y. S., Cereal Chem. 43, 313 (3C) kididler, Y., de la Gueriviere, J. (1966). F., Seince, Y., Benoualid, K., Staerke (39C) Kopriva, B., Krejcova, B., Prumysl Potravin 18, 58 (1967); Anal. Abstr. 20,78 (1968). (4C) Berger, P. D.,Borodkin, S. E., 15,2267 (1968). (40C) Lato, M., Brunelli, B., Ciuffini, Intern. Sugar J . 69,3 (1967). (5C) Berener. H.. Schramm. S.. Arch. G.. Mezzetti., T.., J . Chromalour. 34. T;’ererniehr: 18, 41 (1968); ‘ Chem. 26’(1968). Abslr. 68, 113372~ (1968). (41C) Lewis, L. N., Coggins, C. W., Jr., (6C) Bermejo AIartinez, F., hlargalet Knapp, J. C. F., ibid., 20, 421 (1965). Barral, A., Infcion Quim. Analit. Pura (42C) Lombard, A., ibid., 26,283 (1967). Apl. Ind. 19, 114 (1965); Anal. Abstr. (43C) AIarais. J. P.. S. Afr. J . Auric. Sci. 13,6889 (1966). 9, 267 (1966); Anal. “Abstr. i4, 4267 (7C) Bethge, P. O., Holmstrom, C., (1967). Jnhlin, S., Svensk. PappTidn. 69, 60 (44C) llarais, J. P., de Wit, J. L., (1!)66); Anal. Abstr. 14, 4109 (1967). Quicke, G. V., Anal. Biochem. 15, 373 (8C) Binnb, W. W,, Blunden, G., Phurm. (1966). J . 194,577 (1965). (45C) Martin. L. F.. U. S. 3.384.564 , , (9C) Braun, I). E., U‘adman, W. H., (May 21, 1968). ANAL.CHEM.39, 840 (1967). (46C) RIedcalf, D. G., Gilles, K. A., (lOC) Brobst, K. XI., Lott, C. E., Jr., Cereal Chem. 42.546 (1965). Proc. Am. SOC.Brew. Chem. 1966 71. (47C) Monselise, ’J. J.,~ Israel J . Technol. (1lC) Buchta, K., 2. Anal. Chem. 228, 17 (1967). 3, (1966); Anal. Abstr. 14, 4268 (1967). I
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(48C) Nowlan, S. S., Dyer, W. J., Fraser, 1). I., J . Fish Res. Board Can. 25, 1525 (1968); Chem. Abstr. 69, 66174r (1968). (49C) Ohms, J. I., Zec, J., Benson, J. V., Jr., Patterson, J. A., Anal. Biochem. 20,51 (1967). (50C) Ojtozy, K., Elelmiszervizsgalati Kozlemzen 12, 323 (1966); Anal. Abstr. 14, 6409 (1967). (5lC) Ojtozy, K., ibid., 13, 76 (1966); Chem. Abstr. 69,26085t (1968). (52C) Parker, F. S., Ans, R., Appl. Spectrosc. 20,384 (1966). (53C) Pastiiszyn, A., Michl, H., Mitt. VersAnst. GarGew.. Wien 20, 1 (1966); Anal. Abstr. 14,5752 (1967). (54C) Pokrovskaya, N. V., Vorob’eva, M. T., Chistyakova, M. T., Rogal’, V. D.,Tr. Vses, Nauchn-Issled Znst. Pivobenzalk. Vinodel Prom., (12) 66 (1965); Anal. Abstr. 14, 1704 (1967). (55C) Potter, A. L., Ducay, E. D., McCready, R. M., J . Ass. Ofic. Anal. Chemists 5 1,748 (1968). (56C) Rakhimbaev, I. R., Prikl. Biokhim. Mikrobiol. 4, 125 (1968); Chem. Abstr. 68,86198j (1968). (57C) Richter, M.,2. Anal. Chem. 222, 381 (1966). (58C) Richter, &I.,Szejtli, J., Staerke 18, 95 (1966). (59C) Rattloff, H., Rothe, M.,Friese, R., Schierbaum, F., 2. Lebensm.Un1ersuch.-Forsch. 130, 201 (1966). (60’2) Rychlik, &I.,Fedorowska, Z., Rocz. Panstw. Zakl. Hig. 18, 735 (1967); Chem. Abstr. 6 8 , 9 4 7 2 7 ~(1968). (61C) Samuelson, O., Stromberg, H., J . Food Sci. 33,308 (1968). (62C) Sanderson, G. W., Perera, B. P. hl., Analyst 91, 335 (1966). (63C) Sawyer, R., ibid., 90,476 (1965). (64C) Scherz, H., Riicker, W., Bancher, E., Mikrochim. Ichoanalyt. Acta 876 (1965); Anal. Abstr. 14, 2109 (1967). (65C) Shellard, E. J., Jolliffe, G. H., J . Chromatogr. 24, 76 (1966). (66C) Stella, C., Niccolai, L., Riv. Vitic. Enol. 19, 104 (1966); Anal. Abstr. 14, 5760 (1967). (67C) Stoll, E., Mitt. Gebiete Lebensmitt. Hyg. 58,56 (1967). (68C) Sullivan, J. W., Dissertation Abstr. 27B, 1402 (1966). (69C) Taiifel, K., Behnke, U., Wersuhn, H., 2. Zuck Znd. 15, 462 (1965); Anal. Abstr. 14. 3.58.5 - - - - (19871. (70C) Terent’ev, A. P:, Novikova, I. S., Zh. Analit. Khim. 20, 1226 (1965); Anal. Abstr. 14, 4034 (1967). (71C) Thaler, H., Arneth, W., 2. Lebensm. Un1ersuch.-Forsch, 138, 26 (1968). (72C) Thoburn, J. M., Intern. Sugar J . 68,205 (1966). (73C) Tschersich, J., Mauch, W., 2. Zuckerind. 18, 107 (1967); Chem. Abstr. 69, 1833k (1968). (74C) Urbas, B., Can. J . Chem. 46, 49 ( 1968). (75C) Van Handel, E., Anal. Biochem. 22,280 (1968). (76’2) Van Handel., E.., ibid.. 19. 193 (1967). (77C) Walker, H. G., Jr., Intern. Sugar J . 7,237 (1965). (78C) Walborg, E. F., Jr., Lantz, R. S., Anal. Biochem. 22, 123 (1968). (79C) Weiss, J. B., Smith, J. B., Xature 215.638 (1967). (8OC)‘Winkler. S . . Luckow. G.. Staerke ’ 19,’110(1967). ’ (81’2) Wisler. J. R.. Free. A. H.. Food Technol. 22: 98 I1968 ). ’ (82C) Wolfrb;n,- ‘L., -‘Anderson, L. E., J.Agr. Food Chem. 15,685 (1967). (83C) Wolfrom, 11. L., Tipson, R. S., “Advances in Carbohydrate Chemistry,” 5’01. 21, Academic Press, New York, 1966. I
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(84C) Wolfrom? M. L., Ti son, R. S.,
“Advances in Carbohygate Chemistry,” T’ol. 22, Academic Press, New York, 1967. (85C) Yaphe, W., Arsenault, G. P., Anal. Baochem. 13,143 (1965). (86C) Yariv, J., Lis, H., Katchalski, E., Biochem. J. 105, IC (1967). (87C) Zentner, H., Analyst 90, 698 (1965). Color
(1D) Benk, E., Alkohol-Znd. 79, 619 (1966); Anal. Abstr. 15, 1663 (1968). (2D) Benk, E., Riechstoffe Aromen 17, 96 (1967); .Anal. Ahtr. 15, 4270 (1966). (3D) Benk, E., Brixius, L., Wolff, I., Deut. Lebensm. Rundschau 62, 139 (1968). (4D) Benk, E., Dietl, R., Brixius, L., ibid., 63,110 (1967). (5D) Bieber, H., ibid., 63,44 (1967). (6D) Blaya, S. N., Martinez, A. O., Costa, F., Anales Bromatol. (Madrid) 17, 269 (1965); Anal. Abstr. 13, 7126 (1966). \ - - - - / .
(7D) Co, H., Markakis, P., J . Food Sci. 33,281 (1968). (8D) Copius-Peereboom, J. W., Beekes, H. W., J . Chromutogr.20, 43 (1965). 19D) Davidek. J.. Davidkova., E.., ibid.. ‘ 26,529(1967). ‘ (1OD) Dendy, D. A. V., J. Sci. Food Agr. 17,75 (1966). (1lD) Diemair, W., Polster, A., 2. Lebensm.-Untersuch.-Forsch. 134, 80 (1967). (121)) Dobrecky, J., De Carnevale, B., Rosa, C. D., Rev. Asoc. Bioquim. Argent. 32, 139 (1967); Chem. Abstr. 69,58408e (1968). (13D) Dorier, P., Verelle, L.-P., Ann Fals. Ezpert. Chim. 59, 1 (1966); Anal. Ab&. 14,5048 (1967). (14D) Eisenbrand, J., Hett, O., Becker, G.. Deut. Lebensm. Rundschau 61. 177 (1965). (15D) Fuleki, T., Francis, F. J., J . Food Sci. 33,72 (1968). (1611) Fuleki, T., Francis, F. J., ibid., 33,266 (1968). (17D) Hadorn, H., Zurcher, K., Ragnarson. V.. Mitt. Gebiete Lebens. Hula. -_ 58,’l (1967). (18D) Hamed, M. G. E., 2. Lebensm. Untersuch.Forsch. 130, 164 (1966). (19D) Johnson, R. K., J . Ass. Ogic. Anal. Chem. 50,526 (1967). (2011) Jones, F. B., ibid., 49, 674 (1966). (21D) Kasim, M., Nahrung 11,405 (1967). 122D) Keith. E. S.. Powers. J. J.. J. Food Sci. 31,971 (1966). ’ (23D) Koch, J., Haase-Sajak, E., 2. Lebensm.-Untersuch.-Forsch. 131, 347 (1967). (241)) Lehmann, G., Hahn, H.-G., Deut. Lebensm. Rundschau 63,6 (1967). (25D) Maier, H. G., Diemair, W., Ganssmann, J., 2. Lebensm. Untersuch. Forsch. 137,282 (1968). (26D) Mizunoya, Y., Kita, T., Japan Analyst 14,437 (1965). (27D) Morton, A. D., J . Chromatogr. 28,480 (1967). (281)) Oi, N., Inaba, E., J. Pharm. SOC. Japan 87, 741 (1967); Anal. Abstr. 15,6295 (1968). (29D) Niitsu, Y., Japan Analyst 13, 1239 (1964). (30D) Parrish, J. R., J. Chromabar. 33, 542 (1968). ‘ (31D) Pattee, H. E., Purcell, A. E., J . Amer. Oil Chem. SOC.44, 328 (1967). 132Di Pearson. D.. J . Ass. Publzc Analwsts 4,61 (1966). ’ (33D) Pearson, D., ibid., 5,37 (1967). (34D) Pearson, D., Walker, R., ibid., 3, 45 (1965). ~
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ANALYTICAL CHEMISTRY
(35D) Pokorny, J., Karvanek, M., Davidek, J., Sb. Vysoke Skoly Chem. Technol. v. Praze, E 10, 13 (1966); Anal. Abstr. 14,5761 (1967). (36D) Pourrat, H., Tronche, P., Pourrat, A,, Bull. Soc. Chim. France 1918 (1966); Anal. Abstr. 14,7861 (1967). (37D) Puski, G., Francis, F. J., J . Food Sci. 32,527 (1967). (38D) Reiners, W., 2. Anal. Chem. 229, 406 (1967): Anal. Abstr. 15. 6294 (1968). (39D) Ribereau-Gayon, P., Stonestreet E., Bull. SOC. Chim. France, 2649 (1965); Anal. Abstr. 14, 403 (1967). (40D) Ribereau-Gayon, P., Stonestreet, E., Deut. Lebensm. Rundschau 62, 1 (1966). (41D) Rother, H., ibid., 62, 108 (1966). (42D) Somers, T. C., J . Sci. Food Agr. 18, 193 (1967). (43D) Stinson, E. E., Willits, C. O., J . Ass. Oflc. Agr. C h . 48, 493 ( 1965). (4411) Takino, Y., Ferretti, A., Flanagan, V., Gianturco, M. A., Vogel, M., Can. J . Chem. 45,1949 (1967). (45D) Tomas, F., Carpena, O., Abrisqueta, G., Anales Bromatol. (Madrid) 18, 393 (1966); Anal. Abstr. 15, 1638 (1968). (46D) Weichel, H. H., Deut. Lebensm. Rundschau 62,53 (1966).
Enzymes
(1E) Babson, A. L., Greeley, S. J., J . Assoc. Ogic. Anal. Chem. 50, 555 (1967). (2E) Brenner, M. W., Messing, R., Streifer, S., Golyzniak, R., Proc. Amer. SOC.Brew. Chem. 236 (1966). (3E) Collier, B., J. Znst. Brewing 72, 204 (1966). (4E) De Amorim, H. V., Silva, D. M., Nature 219,381 (1968). (5E) Gunther, F., Burckhart, O., 2. Lebensm. Untersuch. Forsch. 135, 327 (1968). (6E) Gunther, F., Burckhart, O., Deut. Lebensm. Rundschau 63, 41 (1967). (7E) Hadorn, H., Zurcher, K., ibid., 62, 195 (1966). (8E) Hammond, E. G., Seals, R. G., Reinbold, G. W., J. Dairy Sci. 49, 504 11966). (9E) Honold, G. R., Dissertation Abstr. 28B, 474 (1967). (10E) Kiermeier, F., Gull, J., Naturwissenschaften 53, 613 (1966); Anal. Abstr. 15, 1578 (1968). (11E) Kiermeier, F., Solms-Baruth, H., 2. Lebensm. Untersuch. Forsch. 133. 365 (1967). (12E) Kleyn, D. H., Lin, S. H. C., J . Ass. Ogic. Anal. Chem. 51, 802 (1968). (13E) Lee, F. A., Chem. & Znd. 1967, 2!M
(1iEj‘Leuprecht, H., Schaller, A., Fruchtsaft-Znd. 12, 2 (1968); Chem. Abstr. 69,75622n (1968). (15E) Lukach, E. N., Shkvarkina, T. I., Khlebopek. Konditer. Prom. 12, 12 (1968); Chem. Abstr. 69, 34780u (1968). \ - -
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(16E) O’Brien, J. E., J . Dairy Sci. 49, 1482 (1966). (17E) Payry, R. M.! Jr., Chandan, R. C., Shahani, K. M., zbad., 49, 356 (1966). ( B E ) Perten,. H.,. Cereal Chem. 43, 336 (1966). (19E) Primo Yufera, E., Serra, J., Montesinos, M., Rev Agroquim. Tecnol. Alimentos 7, 105 (1967); Anal. Abstr. 15,3601 (1968). (20E) Rohrlich, M., Winkler, S., Hitse, W., Staerke 19, 166 (1967).
(21E) Schormuller, J., Pfrogner, N., Belitx, H.-D., Z. Lebensm. Untersuch. Forsch. 127, 57 (1965). (22E) Voigt, J., Noske, R., ibid., 129, 359 (1966). (23E) Weissler, H. E., Eigel, J. A., Garza, A. C., Proc. Amer. SOC.Brew. Chem.215 (1966). (24E) White, J. W., Jr., Kushnir, I., Anal. Biochem. 16,302 (1966). (25E) Willits, R. E., Babel,‘ F. J.. J . . D&ry Sci. 48,1287 (1965). (26E) Winkler, S., Luckow, G., Staerke 19, 159 (1967). Fats, Oils, and Fatty Acids
(1F) Ackman, R. G., J . Chromatogr. 28, 225 11967). (2F) Ackman, R. G., J . Amer. Oil Chem. SOC.43,483 (1966). (3F) Ackman, R. G., J . Gas Chromatogr. 4,256 (1966). (4F) Amano, R., Shokuhin Eiseigaku Zasshi 7. 334 11966): Chem. Abstr. 69,26099p (1968j. (5F) Appleby, A. J., Mayne, J. E. O., J . Gas Chromatogr. 5,211 (1967). (6F) Appleby, A. J., Mayne, J. E. O., ibid., 5,266 (1967). (7F) Babicheva, 0. I., Gorelik, L. D., Konserv. i Ovoshchesushil. Prom. 23, 35 (1968); Chem. Abstr. 68, 1133762 (1968). (8F) Bailey, A. V., Boudreaux, G. J., Skau, E. L., J . Amer. Oil Chem. SOC. 42,637 (1965). (9F) Bailey, A. V., Harris, J. A., Skau, E. L., Kerr, T., ibid., 43, 107 (1966). 110F) Baltes. J.. Fette. Seifen. Anstrich‘ miltel 69, 512 ‘(19671; Akal.‘ Abstr. 15, 6317 (1968). (11F) Basilico, F., Corriere Farm. 21, 534 (1966); Anal. Abstr. 15, 462 (1968). (12F) Becker, E., Niederstebruch, A., Fette, Seifen, Anstrichmittel 68, 135 (1966); Anal. Abstr. ,14, 3609 (1967). (13F) Becker, E., Niederstebruch, A,, ibid., 68, 182 (1966); Anal. Abstr. 14, 4315 (1967). (14F) Ben-Gera, I., Norris, K. H., J . Food Sci. 33,64 (1968). (15F) Bhatty, M. K., Craig, B. M.,Can. J.Biochem. 44,311 (1966). (16F) Black, L. T., Spyres, G. G., Brekke. 0. L.. Cereal Chem. 44. 152 (1967). ’ (17F) Black, L. T., Beal, R. E., Lipids 2,280 (1967). (18F) Brown, C. A., Sethi, S. C., Brown, H. C., ANAL.CHEM.39,823 (1967). (19F) Chakrabarty, M. M., Bhattacharyya, D., Gupta, A., J . Chromatogr. 22, 84 (1966). 120F) Christie. W. W., Holman. R. T.. ‘ Lipids.1, 176 (1966). ‘ (21Fi Ciurlo. R.. Biino. L.. Quaderni Merceol. 6, 59‘ (1967); C t m : Abstr. 69,26095j (1968). (22F) Clarke, J. R. P., Fredricks, K. M., J . Gas Chromutogr. 5, 99 (1967). (23F) Cocks, L. V., Van Rede, C., “Laboratory Handbook For Oil and Fat Analysts,” Academic Press, New York, 1966. (24F) Coenen, J. W. E., Wieske, T., Cross, R. S., Rinke, H., J . Amer. Oil Chem. SOC. 44,344 (1967). (25F) Colakoglu, M., Riv. Ztal. Sostanze Grasse 44, 529 (1967); Chem. Abstr. 68,862472 (1968). (26F) Collins, F. I:, Alexander, D. E., Rodgers, R. C:,.Silvela, L. S., J . Amer. Oil Chem. Soc. 44, IU8 ( l Y 0 , ) . (27F) Copius-Pt?ereboom, J. W., J. Gas Chromatogr. 3,325 (1965). (28F) Courlios-Salvi, L., Weeden, D. G., Chem. Znd. (Londonj 1967,544. I ,
\--
---
i29F’i Davison. V. L.. Dutton.’ H. J.. ‘ J . L i p i d Res.’8, 147 11967). (30F) dellan, J. AI., Lab. Pract. 16, 150 ( 1967). (31F) Dolev. A.. Olcott. H. S.. J . Amer. Oil Chem. SOC. 42,624 (1965).‘ (32F) Drapron, R., Fisher, N., Getreide Mehl 18, 7 (1968); Chem. Abstr. 68, 86146r (1968). (33F) Dyatlovitskaya, E. V., Volkova, V. I., Bergel’son, L. D., Zzv. Akad. X a u k SSSK, Ser. Khim. 946 (1966); Anal. Abstr. 14,5729 (1967). (34F) Dyatlovitskaya, E. V., Voronkova, T7. T-., Bergel’son, L. D., ibid., 1960 (1965); Anal. Abstr. 14, 1571 (1967). (35F) Eberhardt, K.-H., Bognar, A., Deut. Lebensm. Rundschau 62, 145 (1966); Anal. Abstr. 14, 5728 (1967). (36F) Emken, E. A., Scholfield, C. R., Davison, V. L., Frankel, E. N., J . Amer. Oil Chem. Soc 44, 373 (1967). (37F) Evans, C. D., LIcConnell? ,D. G., Hoffmann R. L., Peters, H., zbzd., 44, 281 (1967). (38F) Evans, C. D., RIcConnell, D. G., Scholfield, C. R., Dutton, J. H., ibid., 43,345 (1966). (39F) Fedeli, E., Riu. Ital. Sostanze Grasse 44, 220 (1967); Chem. Abstr. 68,2050~1(1968). (40F) Fedeli, E., Rev. Franc. Corps Gras 15,281 (1968); Chem. Abstr. 69, 66183t ( 1968). (41F) Fedeli, E., Lanzani, A., Jacini, G., Ria. Zlal. Sostante Grasse 43, 509 (1966). (42F) Fiecchi, A., Capella, P., Fedeli, E., Lanzani, A., Jacini, G., Ric. Sci. Riv. 36, 1316 (1966); Anal. Abstr. 15, 1665 (1968): (43F) Fioriti, J. A,, Bentz, A. P., Sims, R. J., J . Amer. Oil Chem. SOC.43, 487 (1966). (44F) Fioriti, J. A., Sims, R. J., J. Chromatogr. 32, 761 (1968). (45F) Fioriti, J., Krampl, V., Sims, R. J., J. Amer. 0 2 1 Chem. SOC.44, 534 (1967). (46F) Gaddis, A. AI., Ellis, R., Currie, G. T., Thornton, F. E., ibid., 43, 242 (1966). (47F) Gaddis, A. bI., Ellis, R., Shamey, J., Currie, G. T., ibid., 42, 620 (1965). (48F) Garg, B. M. L., Verma, I. S., Intern. Dairy Congr., Proc. 17th, Xunich 4,343 (1966). (49F) Geoghegan, J. T., Rodson, M., J . Amer. Oil Chem. SOC.45, 533 (1968). (50F) Gerson. T.. Shorland. F. B.. Mc‘ Intosh, J. E. A., J . Chiornutog;. 23, 61 (1966). (51F) Ghosh, A,, Ghosh, A., Dutta, J., Indian J . Technol. 6, 19 (1968); Chem. Abstr. 69, 1878d 11968). (52F) Glass, R . L., Jenness, R., Troolin, H. A., J . Dairy Sci. 48, 1106 (1965). (53F) Goaakumar. K.. Xair. M. R.. Indian j.Biochem. 4,229 (1967). (54F) GOLIW,T. H., Vlugter, J. C., Roelands, C. J. A., J. Amer. Oil Chem. SOC.43,433 (1966). (55F) GUS, P. L., Richardson, T., Stahmann, &I. A., ihid., 45, 272 (1968). (56F) Hadorn, H., Zuercher, K., Mitt. Lebensm. u. Hyg. 58, 209 (1967); Chem. Abstr. 69,9772k (1968). 157F) Hadorn. H.. Zuercher. K.. ibid.. 58, 236 (1467);‘ Chem. A’bstr.’ 69, p 1829 (1968). (58Fj Hagan, S. K., Murphy, E. W., Shelley, L. M.,J . Ass. Oj’ic. Anal. Chem. 50,250 (1967). (59F) Hammonds, T. W., Shone, G. G.. Analyst 91,455 il966). ’ (60F) Hassan, JI. ht., Lea, C. H., Chem. Znd. (London) 1965, 1760; Anal. Abstr. 14,1076 (1967). ~
(61F) Hayakawa, K., J . Amer. Oil Chem. SOC.44,354 (1967). (62F) Hornstein, I., Crowe, P. F., Ruck, J. B., ANAL.CHEM.39,352 (1967). (63F) Hote-Baudart. E..Bull. Rech. Aoron. Gembloux 2, 667 (1967); Chem. Abstr. 69,34745m (1968). (64F) Iverson, J. L., Eisner, J., Firestone, D., J. Ass. Oj’ic. Anal. Chem. 48,1191 (1965). (65F) Jacini, G., Fedeli, E., Lanzani, A., ibid., 50,84 (1967). 166F) Jackson. R. B.. J . Chromatoor. 22. 251 (1966). ’ (67F) Jamieson, G. R., Reid, E. H., ibid., 20,232 (1965). (68F) Jamieson, G. R., Reid, E. H., ibid., 29,44 (1967). (69F) Jensen, R. G., Sampugna, J., J . Dairy Sci. 49,460 (1966). (70F) Jensen, R. G., Quinn, J. G., Carpenter, D. L., Sampugna, J., ibid., 50,119 (1967). (71F) Johnson, A. R., Murray, K. E., Fogerty, A. C., Kennett, B. H., Pearson, J. A,, Shenstone, F. S.,. LiDids 2. 316 . (1967). (72F) Johnson, C. B., Holman, R. T., ihid., 1,371 (1966). (73F) Jones, D., Bowyer, D. E., Gresham, G. A,, Howard, A. N., J . Chromatogr. 23,172 (1966). (74F) Kaderavek, G., Volonterio, G., Riv. Ztal. Sostanze Grasse 43,9 (1966). (75F) Kaderavek, G., Volonterio, G., ibid., 44,75 (1967). (76F) Karleskind, A,, Chim. Anal. 49, 86 (1967); Anal. Abstr. 15, 4302 (1968). (77F) Karleskind, A., Audiau, F., Wolff, J. P., Rev. Franc. Corps Gras 13, 165 (1966); Anal. Abstr. 14,4311 (1967). (78F) Kaufmann, H. P., Radwan, S. S., Ahmad, A. K. S., Fette, Seifen, Anstrichmittel 68, 261 (1966); Anal. Abstr. 14,4896 (1967). (79F) Kaufmann, H. P., Viswanathan, C. V., ibid., 67, 662 (1965); Anal. Abstr. 14,299 (1967). (80F) Kintner, J. A., Day, E. A., J . Dairy Sci. 48,1575 (1965). (81F) Kircher, H. W., J . Amer. Oil Chem. SOC. 42,899 (196.5). (82F) Kiribuchi, T., Mizunaga, T., Funahashi, S., Agr. Biol. Chem. (Tokyo)30, 770 (1966); Anal. Abstr. 14, 7896 (1967). (83F) Knapp, F., Aexel, R., Nicholas, H. J., J . Food Sci. 33,159 (1968). (84F) Kopecky, A,, Nahrung 12, 87 (1968); Chem. Abstr. 68, 103957a (1968). (85F) Kresze, G., Schauffelhut, F., 2. Anal. Chem. 229, 401 (1967); Anal. Abstr. 15, 6314 (1968). (86F) Krewson. C. F.. J. Amer. Oil Chem. ‘ Soc. 45,250 (1968). ’ (87F) Kuemmel, D. G., ChaDman.’ L. R., ANAL.CHEM. 38, isii (1966). (88F) Kuksis, A,, Ludwig, J., Lipids 1, 202 (1966). (89F) Kuzdal-Savoie, S., Petit, J., Intern Dairy Congr., Proc. 17th Munich 4, 329 (1966); Chem. Abstr. 68, 58592q (1968). (90F) Kuzdzal-Savoie, S.. Trehin. J.. Lakt 48, 121 (1968j; Chem. Abst;. 69; 75632r (1968). 191F) Kuznetsov. V. I.. Parinov. V. Y.. . Vopr. Pitaniya 27, 64 (1968); Chem: Abslr. 69,75640s (1968). (92F) Kwapniewski, Z., Sliwiok, J., J. Chromatogr. 19,204 (1965). (93F) Leclercq, B., Agot, A., Lemarchal, P., Bull. SOC.Chim. Biol. 48,345 (1966); Anal. Abstr. 14, 5730 (1967). (94F) Lee, C. F., Ambrose, &I.E., Smith, P., Jr., J . Ass. Oj’ic. Anal. Chem. 49,946 (1966). ~
~
(95F) Levkovich, G. A., Kuvichinskaya, T. V., Lakokrasochnye Materialy i i k h Primenenie 54 (1966); Anal. Abstr. 15,858 (1968). (96F) Litchfield, C., Harlow, R. D., Reiser, R., Lipids 2,363 (1967). (97F) Lotito, A., Cucurachi, A,, Riv. Ztal. Sostanze Grasse 44, 341 (1967); Chem. Abstr. 6 8 , 2 0 5 1 ~(1968). (98F) Lough, A. K., Navia, J. M., 43,627 Harris, (1966). R. S., J . Amer. Oil Chem. SOC. (99F) Luck, H., Kohn, R., Milchwissenschaft 20, 455 (1965); Anal. Abstr. 14, 1687 (1967). (100F) MacKenzie, R., Blohm, T. R., Auxier, E. M., Luther, A. C., J . Lipid Res. 8,589 (1967). (101F) Mahmood-ul-Hassan., Pearson, D., J . Sci. Food Agr. 17,421 (1966). (102F) Mallard, T. M.,Craig, B. iM., J . Amer. Oil Chem. SOC.4 3 , l (1966). (103F) Miettinen, T. A., Ahrens, E. H., Jr., Grundy, S. M., J . Lipid Res. 6, 411 (196j). (104F) Mitchell, D. J., Weik, R. W., J . Ass. Oj’ic. Anal. Chem. 50, 537 11967). (105F) Miwa, T. K., Kwolek, W. F., Wolff, I. A., Lipids 1,152 (1966). (106F) hlizuno, G. R., ChiDault. J. R.. J . Amer. Oil Chem. SOC.42, 839 (1965): (107F) Monteoliva, M., Perez Soler, J. D.. Ibanez. C.. Trarela. G.. Gmmoa 11 - _.__ Aceitks (Sevilk, $pain) 18,269 (1967f; 18, 209 (1967); Anal. Abstr. 15, 6309 (lQfi8) \-___,.
(108F) Mooney, R. P., Pasarela, N. R., J . Agr. Food Chem. 14,12 (1966). (109F) Morris, L. J., J . Lipid Res. 7, 717 (1966). (llOF) Nickell, E. C., Privett, 0. S., Separ. Sci. 2,307 (1967). (111F) Novak, M., J . Lipid Res. 6 , 431 (1965). (112F) Oette, K., ibid., 6,449 (1965). (113F) Olley, J., Fishing News Int. 5, 36 (1966). (114F) Ord, W. O., Bamford, P. C., Chem. Znd. (London)1966,1681. (115F) Ord, W. O., Bamford, P. C., ibid., 277 (1967). (116F) Ord, W. O., Bamford, P. C., ibid., 2115 (1967). (117F) Pallotta, U., Riv., Ital. Sostanze Grasse 42, 587 (1965); Anal. Abstr. 14, 2267 (1967). (118F) Pallotta, U., Znd. Agr. (Florence) 4, 297 (1966); Anal. Abstr. 14, 5765 (1967). (119F) Paoletti, R Kritchevsky, D., “Advances in Lipih Research,” Vol. 4, Academic Press, New York, 1966. (120F) Pardun, H., Deut. Lebensm. Rundschau 62, 6 (1966); Anal. Abstr. 14, 3613 (1967). (121F) Parker, F., Rauda, V., Morrison, W. H., J . Chromatogr. 34,35 (1968). (122F) Parodi, P. W., Aust. J . Dairy Technol. 22. 144 (1967). (123F) Pauldse, Ih,M:, J . Chromatogr. 21,141 (1966). (124F) Pazlar, Jf., Kocova, P., Pokorny, J., 2. Lebensm. Untersuch. Forsch. 131, 269 (1966). (125F) Peters. H.. Wieske. T.. Fette. Seifen, Anst;ichmhteZ68,947 (1966). ‘ (126F) Piorr, W., Toth, L., 2. Lebensm. Untersuch. Forsch. 132,69 (1966). (127F) Pohle, W. D., Gregory, R. L., J . Amer. Oil Chem. SOC.44, 397 (1967). (128F) Pokorny, J., Karvankova, J., Hrdlicka, J., 2. Lebensm. Untersuch. Forsch. 130, l(1966). (129F) Pokorny, J., Zwain, H., Fette, Seifen, Anstrichmittel 69, 330 (1967); Anal. Abstr. 15,5042 (1968). (130F) Pomeranz, Y., Chung, O., J . Chromatogr. 19,540 (1965). VOL. 41, NO. 5, APRIL 1969
83R
(131F) Privett, 0. S., Nickell, E. C., J . Amer. Oil Chem. SOC. 43,393 (1966). (132F) Radler, F., J . Sci. Food Agr. 16, 638 (1965). (133F) Raju, P. K., Reiser, R., Lipids 1, 10 (1966). (134F) Rao, P. B., Sreenivasan, B., Chem. Znd. (London) 1966,1376. (135F) Rothe, M., Wolm, G., Voigt,, I., Xahrung 11, 149 (1967); Anal. Abstr. 15,2935 (1968). (136F) Ruseva-Atanasova. N.. Janak. J.. ' J . Chromatogr. 21,207 (1966j. (137F) Sandev, S., Baltadzhieva, M., Lait 48, 141 (1968); Chem. Abstr. 69, 51035x (1968). (138F) Sato, K., Matsui, M.,Ikekawa, N., Bunseki Kagaku 16, 1160 (1967); Chem. Abstr. 69,26083d (1968). (139F) Schober, B., Faschereiforschung 5, 121 (1967); Chem. Abstr. 69, 1825j ,
I
-
(,1- R - 6- X I,.
(140F) Schoenmakers, A. W., Tarladgis, B. G., Nature 210,1153 (1966). (141F) Scholfield, C. R., Davison, 1'. L., Dutton, H. J.,'J. Amer. Oil Chem. Soc; 44,648 (1967). (142F) Scholfield, C. R., Butterfield, R. O., Dutton, H. J., ANAL.CHEM.38, 1694 (1966). (143F) Seher, A., Nahrung 11, 825 (1967); Chem. Abstr. 68,86244~(1968). (144F) Sgoutas, D. S., Nature 211, 296 (1966). (145F) Shepherd, I. S., Ross, L. F., Morton, I. D., Chem. Znd. (London) 1966,1706. (146F) Sigler, K., Berka, A., Zyka, J., Microchem. J . 11,398 (1966). (147F) Sliwiok, J., Kwapniewski, Z., ibid., 9, 237 (1965). (148F) Smith, T. M.,White, H. B., Jr., J . Lipid Res. 7,327 (1966). (149F) Soucek, J., Vasatkova, J., COG Zection Czech. Chem. Commun. 31, 2860 (1966); Anal. Abstr. 14,6964 (1967). (150F) Streuli, H., Schwab-von Buren, H., Hess, P., Mitt. Gebiete Lebensm. Hyg. 57, 142 (1966); Anal. Abstr. 14,4297 (1967). (15lF) Teague, R. T., Jr., Joe, F. L., Jr., J . Ass. Ofic. Anal. Chem. 49, 959 (1966). (152F) Tichy, J., Dencker, S. J., J . Chromatogr.33,262 (1968). (153F) Tinoco, J., Miljanich, P. G., Anal. Biochem. 11,548 (1965). (154F) Telasco. J.. J. Amer. Oil Chem. ' Soc.'44,-48 (1967j. (15,jF) Whalen, F., J. Ass. Ofic. Anal. Chem. 49, 1225 (1966). (l56F) White, H. B., Jr., Powell, S. S., J . Chromatogr.32,451 (1968). (l57F) White, H. B., Jr., ibid., 21, 213 (1966). (158F) William:, K. A., "Oils, Fats and Fattv Foods. ~ - - American Elsevier Pubrishing Co., Ihc.,New York, 1966. (l59F) Woidich, H., Z. Lebensm. Untersuch. Forsch. 129, 197 (1966). (160F) Wood, R., Snyder, F., Lipids I , ' 62 ( ~ 6 6 ) . (161F) Wood., R.., J . Gas Chromatoor. 6. ' 94 (1968). (162F) Zmachinski, H., Waltking, A., Miller, J. D., J . Amer. Oil Chem. SOC. 43,425 (1966). i
I
.
Flavor and Volatile Compounds
(1G) Abousteit, O., Fette, Seifen, Anstrichmittel 69, 1 (1967). (2G) Adams, D. F., Jensen, G. A., Steadman, J. P., Koppe, R. K., Robertson, T. J., ANAL.CHEM.38, 1094 (1966). (3G) Angelini, P., Form, D. A., Bazinet, hl. L., Merritt, C., Jr., J . Amer. Oil Chem. SOC.44,26 (1967). 84 R
ANALYTICAL CHEMISTRY
(4G) Angelini, P., Pflug, I. J., Food Technol. 21, 1643 (1967). (5G) Anjou, K., von Sydow, E., Acta Chem. Scand. 21,2076 (1967). (6G) Anjou, K., von Sydow, E., ibid., 21, 945 (1967). (7G) Arai, S., Sueuki, H., Fujimaki, hI., Sakurai, Y., Agr. Biol. Chem. (Tokyo) 39,863 (1966). (8G) Arima, K., Yamaguchi, G., Tamura, G., Nippon Nogei Kagaku Kaishi 41, 660 (1967); Chem. Abstr. 68, 67896u (1968). (9G) Arsenault, G. P., Yaphe, W., ANAL. CHEM.38,503 (1966). (10G) Asao, Y., Yokotsuka, T., ,?'ippon Jot0 Kyokai Zasshi 62, 1106 (1967); Chem. Abstr. 68,6776613 (1968). (11G) Attaway, J. A., Wolford, R. W., Dougherty, M. H., Edwards, G. J., J.Agr. Food Chem. 15,688 (1967). (12G) Baldwin, S., Black, R. A., Adreasen A. A,, Adams, S. L., ibid., 15, 381 (1967) \ - _ _,..
(13G) Baraud, J., Boll. Lab. Chim. Provinciali (Bologna) 18, 381 (1967); Chem. Abstr. 69,2848911 (1968). (14G) Behun, M., IIrivnak, J., Prumysl Potravin 16, 658 (1965); Anal. Abstr. 14,2832 (1967). (15G) Bernhard, R. A., J . Food Sei. 33, 298 (1968). (16G) Bertrand, A., Boidron, J. N., Ribereau-Gayon, P., Bull. SOC.Chim. France 3149 (1967). (17G) Bitter, H., Brauwissenschaft 19, 278 (1966); Anal. Abstr. 14, 7145 (1967). (18G) Blanc, P., Bertrand, P., de SaquiSannes, G., Lescure, R., Chim. Anal. 47,354 (1965). (19G) Bobrakov, B. P., Soboleva, I. bl., Konserv. i Ovoshchesuchil Prom. 23, 13 (1968); Chem. Abstr. 69, 1908p (1968). (20G) Bondarovich, H. A., Friedel, P., Krampl, Ir.,Renner, J. A., Shephard, F. W., Gianturco, M. A,, J. Agr. Food Chem. 15, 1093,(1967). (21G) Bondarovich, H. A,, Giammarino, A. S., Renner, J. A., Shephard, F. W., Shingler, A. J., Gianturco, M. A., ibid., 15,36 (1967). (22G) Bradley, R. L., Jr., Stine, C. hI., J . Gas Chromatogr.6,344 (1968). (23G) Brand, J. RI., J . Chromatogr. 21, 424 (1966). (24G) Bricout, J., Yiani, R., MugglerChauan, F., Marion, J. P., Reymond, D., Egli, R. H., Helv. Chim. Acta 50, 1.517 (1967). (25G).Brunelle, R. L., J . Ass. Ofic. Anal. Chem. 50,319 (1967). (26G) Brunelle, R. L., ibid.,. 49,. 504 (1966). (27GI Brunelle. R. L.. ibid.. 50. 322 ' (1967). (28G) Burr, H. K., Proc. Plant Sci. Symp. 1966,83. (29G) Cerma, E., Marletta, G. P., Bnn. Fac. Econ. Commer., Univ. Studi Messina 4, 248 (1966); Chem. Abstr. 68, 38177e (1968). (30G) Chandler. B. V., Kefford. J. F., ' J.bci. Food Agr. 17, 193 (1966). ' (31G) Creveling, R. K., Silverstein, R. M., Jennings, W. G., J . Food Sci. 33,284 (1968). (32G) Croteau, R. J., Fagerson, I. S., ibid.. 33. 386 (1968). (33G) 'Daial, K. B.; Salunkhe, D. K., Olson, L. E., Do, J. Y., Yu, M. H., Plant Cell Phvsiol. fTokvo) 9. 389 (1968); Chem. i b s t r . 69, 1 6 4 0 e (1968). (34G) Davidek, J., Petrova, O., 56. Vysoke Skoly Chem.-Techno1 Praze, Oddil Fak. Potravinareske Technol. 12, 67 (1966); Anal. Abstr. 15, 1661 (1968). j ~ . . _ , .
I
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(35G) deBecze, G. I., Smith, H. F., Vaughn, T. E., J . Ass. Ojic. .4nal. Chem. 50,311 (1967). (36G) Drawert, F., Rapp, A., Z. Lebensm. llntersuch. Forsch. 126,406 (1965). (37G) Drawert, F., Heimann, W., Emberger, R., Tressl, R., Phytochemistry 7, 881 (1968); Chem. Abstr. 69, 9826f (1968).
G., Riemann, J.
(1968); Chem. Abstr. 69, 9811x (1968). (42G) Ferren, W. P., Shane, N., Schweigarath, R., Food Technol. 21, 1265 (1967). (43G) Flament, I., Wilhalm, B., Stoll, ll., Helv. Chim. Acta 50, 2233 (1967). (44G) Flath, R. A,, Black, D. R., Guadagni, D. G., McFadden, W. H , Schultz, T. H., J . A g r . Food Chem. 15, 29 (1967). (45G) Forss, D. A., Jacobsen, V. X, Ramshaw, E. H., ibid., 15, 1104 (1967). (46G) Forss, D. A,, Stark, W.,Urbach, G., J . Dairy Res. 34, 131 (1967). (47G) Forss, A,, Holloway, G. L., J. Amer. Oil Chem. Soc. 44,572 (1967). (48G) Gaiitschi, F., Winter, lf,,Flament, Y., Rillhalm, B., Stoll, l f . , J . Agr. Food Chem. 15, 15 (1967). (49G) Gerngross, O., Renda, N., Justus Liebigs dnnln Chem. 691, 186 (1966); Anal. I., Olson, N. F., J . Dairy Sci. 50,461 (1967). (5J) Babakhodzhaeva, S. A,, Rizaev, N. U., Gorokhovskaya, A. S., Khim.Farm. Zh. 2, 42 (1968); Chem. Abstr. 69,34714a (1968). (6J) Barberio, J. C., Rev. Fac. Farm. Bioquim. Cniv. Suo Paulo 5, 439 (1967); Chem. Abstr. 69,26148d (1968). (75) Bionda, G., Ciurlo, R., Biino, L., Ricerca Scient. 37, 665 (1967); Anal. Abstr. 15,6283 (1968). (SJ) Black, B. C., Hammond, E. G., J . Amer. Oil Chem. SOC. 42, 1002 (1965). (9J) Blanchard, R. L., Ari.4~. CHEM.38, 189 (1966). (1OJ) Bogen, D. C., Kleinman, AI. T., Analyst 92,611 (1967). (llJ) Boni, A. L., Alv.4~. CHEM.38, 89 (1966). \ - - - - I
(125) Braid, P., Hunter, J. A., hfassie, W. H. S., Nicholson, J. D., Pearce, B. E., Ana1u.d 0 1 . 4--2 4 (1966) \----,. (135) Brandtip. J., van't Riet, B., ANAL. CHEM.38, 1790 (1966). (145) Brown, R. C., Weaver, bf. L., S t e m . H.. Anal. Biochem. 16. 119 11966). r&ughs, L. F., Anaiyst 93, 618 - - I
\----,.
(16J) Carruthers, A,, Heaney, R. K., Oldfield, J. F. T., Intern. Sugar J . 67, 364 (1965); Anal. Abstr. 14, 2231 ( 1967) . (175) Chaudhry, I. A., Cornfield, A. H., Analyst 91,528 (1966). (185) Chioffi, V., Osti, G., Boll. Lab. Chim. Provinciali (Bologna) 16, 633 (1965); Anal. Abstr. 14,1708 (1967). (19J) Chopra, S. L., Bajaj, K. L., Tharoor, N., J . Indian Chem. SOC. 45, 432 (1968); Chem. Abstr. 69, 428239. (1968). (205) Ciaccio, L. L., Cotsis, T., ANAL. CHEM.39,260 (1967).
(215) Collier, R. E., Hilger J . 10, 52 (1967); Anal. Abstr. 15, 5451 (1968). (225) Covello, AI., Schettino, O., Farmaco, Ed. Prat. 20, 396 (1965): Anal. Abstr. 13.7101 (1966). (23Jj llas, H. A., van Raaphorst, J. G., Hoede, D., Zonderhuis, J., Int. J . Appl. Radiat. Isotopes 17, 252 (1966); Anal. Abstr. 14,5022 (1967). (245) Ilas, H. A., van Raaphorst, J. G., hlenger, J. W., Galesloot, T. E., Nucl. Activ. Tech. Life Sci., Proc. Symp. Amsterdam, 379 (May 1967); Chem. Abstr. 68,113419r (1968). (25J) llavib, S., “Residue Reviews,” 1.01. 12, Springer-T’erlag, Berlin, 1966. (26J) Deibner, L., Bardou, P., Chim. Anal. 48. 278 (1966): Anal. Abstr. 14,5759 (1967). (275) Ueibner, L., Heredia, N., ibid., 48, 66 (1966); Anal. Abstr. 14, 3606 (1967). (2SJ) Demott, B. J., J . Dairy Sci. 51, 1008 (1968). (295) Uittel, F., 2. Anal. Chem. 228, 412 (1967); Anal. Abstr. 15, 5464 (196X). (305) Ilittel, F., ibid., 229, 188 (1967); Anal. Abstr. 15, 5448 (1968). (315) Eakins, J. U., Brown, D. A., Int. J . i l p p l . Radiat. Isotopes 17, 391 (1966); Anal. Abstr. 14, 6990 (1967). (32J) Ellis, AI. K., Wampler, S. N., Yager, 11. H.. Anal. Chim. Acta 34. 169 11966). (335) Erdey, L , Buzas, I.; T’igh, K., Talanta 13, 463 (1966); Anal. Abstr. 14,3790 (1967). (345) Ebchnauer, H., 2. Lebensm. Untersuch. Forsch. 127, 268 (1965). (33J) Eschnauer, H., Tolg, G., ibid., 129, 273 (1966). (36J) Etian, H. O., Rovella, M.A., Proc. Am. SOC.Brew. Chem. 1966, 177; Anal. Abstr. 14,3595 (1967). (375) Fairman, K. I > , Sedlet, J., ANAL. CHEM.38, 1171 (1966). (385) Firbas, B. J., 1-accari, H. G., Silvar, R . L., Roln. SOC.Quim. Peru 31, 57 11963): Anal. Ahstr. 13. 6511 (1966). (39J) Frey, S. W., UeWitt, ‘1%‘. ’G., Bellomy, B. R., Proc. Am. SOC.Brew. Chem. 1966, 172; Anal. Abstr. 14, 3594 (1967). (405) Ganchev, N., IXmitrova, A., Mikrochim. A d a ,507 (1967). (415) Goodall, G. H., C.K. At. Energy Auth., Prod. Group, P. G. Rep. 1968, (815(CA)); Chem. Abstr. 69, 26102j (1968). (425) Hahn, R. B., Johnson, J. L., nIcKay, J. B., Talanta 13, 1613 (1966); Anal. Abstr. 15, 1633 (1968). (435) Halliday, J. H., Wood, F. W., Analyst 91,802 (1966). (445) Hamilton, E. I., hfinski, M. J., Cleary, J . J., ibid., 92, 257 (1967). (45J) Hingorani, S. B., “Proceedings of the Nuclear and Radiation Chemistry Symposium, Bombay, India, March 1964,” Trombay, Bombay, Atomic Energy Estab., 1963; Anal. Abstr. 14, 1247 (1967). (465) Hogdahl, 0. T., Melsom, S., ANAL. CHEM. 38, 1414 (1966). (475) Kirchmann, R., Roderbourg, J., Int. J. Appl. Radiat. Isotopes 16, 457 (1965); Anal. Abstr. 13, 7102 (1966). (4XJ) Labiiza, T. P., Karel, hf., J . Food Sci. 32,572 (1967). (49J) Lechner, E., Kiermeier, F., Z . Lebensm. Untersuch. Forsch. 133, 372 (1967). (5OJ) Lembek, A., Moebus, O., Wasserfall, F., ilfilchwissenschaft 23, 211 (1968); Chem. Abstr. 69, 182811(1968). (5lJ) Lopez, A., Krebs, B. S., Food Technol. 21 (3A): 47A (1967). (525) Nagy, L. G., Nester, Z., Takacs, G., Magy. Kem. Foly. 73, 137 (1967); Anal. Abstr. 15,3612 (196X). ~
, /
(535) Nangniot, P., Chim. Anal. 47, 592 (1965); Anal. Abstr. 14, 1735 (1967). (545) Ogawa, G., Murohashi, M., Ogawa, R., Shokuhin Ezseigaku Zasshi 9, 210 (1968); Chem. Abstr. 69, 66184u (1968). (55J)-Pappas, E. G., Rosenberg, L. A., J . Ass. Ojic. Anal. Chem. 49, 792 (1966). (565) Petrow, H. G., Levine, H., ANAL. CHEM.39,360 (1967). 157J) Richardson, M. L., Talanta 15. Chem. Ab&. 69, 9774n ‘ 483 (1968); (1968). (5iJ)-R;ach, A. G., Sanderson, P., Williams, D. R., AnaZyst 93, 42 (1968). (595) Samuelsson, E.-G., Milchwissenschaft 21, 31 (1966); Anal. Abstr. 14, 3568 (1967). (60J) Silbereisen, K., Kruger, E., Schubert, B., Anthon, F., Mschr. Brau. 20, 121 (1967); Anal. Abstr. 15, 3603 (1968). (615) Skogerboe, R., Gravatt, A. S., Morrison, G. H.. ANAL. CHEM. 39. 1602 (1967). (625) Smith, R. V., Ciaccio, L. L., Lipchiis, R. L., J . Agr. Food Chem. 15, 408 (1967). (635) Smith, P., Jr., Kurtzman, C. H., Ambrose, hl. E., Clin. Chem. 12, 418 (1966); Anal. Abstr. 14,6285 (1967). (645) Souliotis, A. G., Grimanis, A. P., Tsanos, N. A,, Analyst 90,499 (1965). (655) Strasheim, A,, Strelow, F. W. E., Norval, E., J1 S. Afr. Chem. Inst. 20, 25 (1967). Anal. Abstr. 15,6282 (1968). (66J) Tanaka, G., Japan Analyst 15, 1068 (1966); Anal. Abstr. 15, 3001 (1968). (675) Truhaut. R.. Boudene. C.. Phu Lich. N.. hull. ’SOC.Chim: Fr.‘ 1966. 255f; AnacAbstr. 15, 325 (1968). (685) Tuchscheerer, T., 2. Anal. Chem. 215, 416 (1966); Anal. Abstr. 14, 2228 (1967). (69J) Underdal, B., h’ord. Veterinaermed. 20, 9 (1968); Chem. Abstr. 68, 86231q (1968). (705) Underdal, B., ibid., 20, 14 (1968); Chem. Abstr. 68,86232r (1968). (715) Yule, H. P., ANAL.CHEM.38, 818 (1966). (725) Zonneveld, H., Gersons, L., 2. Lebensm. Untersuch. Forsch. 131, 205 (1966). ~
Moisture
(1K) Ballschmieter, H. M. B., Deut. Lebensm. Rundschau 63, 203 (1967); Anal. Abstr. 15,6279 (1968). (2K) Beary, E. G., U.S. Gov. Res. Develop. Rept. 67(20), 34 (1967). (3K) Bolin, H. R., Nury, F. S., J. Agr. Food Chem. 13,590 (1965). (4K) Ince, A. D., Turner, A., Analyst 90, 692 (1965). (5K) Kliman, P. G., Pallansch, hl. J., J. Dairy Sci. 48,859 (1965). (6K) Labuza, T. P., Food Technol. 22, 263 (1968). (7K) Loncih, If.,Bimbenet, J. J., Lenges, J., J. Food Technol. 3, 131 (1968). (8K) hlarov, G. J., Intern. Sugar J . 69, 134 (1967). (9K) RlcCarron, E. A., J . Ass. Ofic. Anal. Chem. 51,577 (1968). (IOK) hliller. H.. Cereal Chem. 45. 109 ’ (1968). (11K) Oshima, H., Kokusuishi Geppo 24, 10 11967): Chem. Abstr. 69. 28559s (196k). ’ ’ (12K) Palotas, J., Lorant, B., llihalik, D., Bahrung 10, 37 (1966); Anal. Abstr. 14,2833 (1967). (13K) Rader, B. R., J . Ass. Ogic. Anal. Chem. 49,726 (1966). (14K) Saraf, D. N., Fatt, I., Nature 214, 1219 (1967). I
.
(15K) Strange, T. E., J . Ass. Ojic. Anal. Chem. 50,547 (1967). (16K) Toledo, R., Steinberg, M. P., Nelson, A. I., J . Food Sci. 33, 315 (1968). (17K) Young, J. H., Nelson, G. L., Trans. A S A E (Amer. SOC.A ar. Enors. ” ,) 10,756 (1967). Organic Acids
(1L) Abdurazakova, S. K., Gabbasova, L. B.. Izv. Vussh. Ucueb. Zaved.. Pishch. Tekhnol. 51 “(1968);“ Chem. Abstr. 68, 94721q (1968). (2L) Amon,, A., Markakis, P., Mich. State Unav., Agr. Exp. Sta., Quart. Bull. 50. 48.5 (1968): Chem. Abstr. 69. 75724~(1968). (3L) Arkima, Y., Mschr. Brau. 18, 121 (196.5); Anal. Abstr. 13, 6541 (1966). (4L) Bellucci, G., Aldini, R., Ind. Conserve (Parma) 42, 99 (1967); Chem. Abstr. 68,67867k (1968). (5L) Bruemmer, J.-lT., Rrot. Geback 19, 238 (1965); Anal. Abstr. 14, 2233 (1967). (6L) Bruemmer, J. M., ibid., 22, 71 (1968); Chem. Abstr. 69, 42806x (1968). (7L) Bruemmer, J.-M., ibid., 21, 112 (1967); Anal. Abstr. 15, 3619 (1968). (8L) Bruemmer, J. AI., Klempin, U., Deut, Lebensm. Rundschau 64, 15 (1968). (9L) Brunelle. R. L.. Schoeneman. R. ‘ L:, Martin,’G. E., J. Ass. Ojic. Anal. Chem. 50,329 (1967). (1OL) Carles, J., J . Chromatogr. 35, 158 (1968). (11L) Chobanov, D., Popov, A., Chuparova, E., Torimakov, N., Sahrung 11, 87 (1967): Anal. Abstr. 15. 2975 (1968). (12L) Clauss, W., Wuerdig, G., Schormueller, J., 2. Lebensm. Vntersuch. Forsch. 131,278 (1966). (13L) Colombo, E., Farmaco, Ed. Prat. 23. (1968): Chem. Abslr. 68, 76967v (1Y68). (14L) Ilavidek, J., Sil’yanova, Y. I., Sb. Vys. Sk. Chem.-Technol. Praze, E. 33 (1966); Anal. Abstr. 14, 5736 (1967). (15L) Delaport, N., hlacheix, J. J., Chim. Anal. (Paris) 50, 187 (1968); Chem. Abstr. 69, 1823g (1968). (16L) de hfoura, J., Dostal, H. C., J . Agr. Food Chem. 13,433 (1965). (17L) I)ranik, L. I., Khim. Prir. Soedin. 2, 303 (1966); Chem. Abstr. 66, 79641d (1967). (18L) Eistert, B., Deut. Lebensm. Rundschau 63, 144 (1967). (19L) Eistert, B., ibid., 63, 273 (1967). (20L) Fernandez-Flores, E., Johnson, A. R., Blomquist, Y. H., J . Ass. 0.flic. Anal. Chfm.51,934 (1968). (21L) Grodzinska-Zachwieja, Z., Kahl, W., Warchol, A., J . Chromatogr. 29, 362 (1967). (22L) Grosjean, hf. H., Fouassin, A., Rev. Ferment. Ind. Aliment. 22, 211 (1967); Chem. Abstr. 69, 26096k (1968). (23L) Hautala, E., J . Ass. 0.flic. Anal. Chem. 49,619 (1966). (24L) Hautala, E., ibid., 50, 287 (1967). (25L) Hautke, P., J . Inst. Brewing 72, 526 (1966); Anal. Abstr. 15, 1082 (1968). (26L) Hempenius, W. L., Liska, B. J., J . DairySci. 51,221 (1968). (27L) Johnson. A. R., Jr., Anal. Chim. Acta 33, 397 (1963). (28L) Johnston, F. B., Hammill, 11. &I., Can. Inst. Food Technol. J . 1, 3 (1968). (29L) Juries, E. W., 2. Lebensm. Untersuch. Forsch. 132,193 (1966). (30L) Klocking, R., Hofmann, R., nluecke, I)., zbid., 135, l(1967). ”
VOL. 41, NO. 5, APRIL 1969
87R
(31L) Kolesnik, ,A. A,, Avdeeva, L. I., Prikl. Baokham. Mikrohiol. 3, 693 (1967); Chem. Ahstr. 68, 86260y (1968). (32L) Kuzdzal, W., Kuzdzal-Savoie, S., Int. Dairy Congr., Proc. 17th Munich 4, 335 (1966); Chem. Abstr. 68, 58593r (1968). (33L) Lehmann, G., Hahn, H.-G., Martinod, P., Luzuriaga, O., Deut. Lehensm. Rundschau 63, 144 (1967). (34L) Lehmann, G., Rlartinod, P., Z . Lehensm. Untersuch. Forsch. 130. 269 (1966). (35L) Li, K. D., Woodroof, J. G., J. Agr. Food Chem. 16,522 (1968). (36L) Lindner, K., Jurics, E. W., 2. Lehensm. Untersuch. Forsch. 128, 65 (1965). (37L) Macheix, J. J., Fruits (Paris) 23, 13 (1968): , , Chem. Ahstr. 68. 113460~ (1968). (38L) Mazliak, P., Salsac, L., Phytochemistry 4, 693 (1965); Anal. Ahstr. 14,287 (1967). (39L) Milic, B., Stojanovic, S., Vucurevic, N.. Turcic. M.. J . Sci. Food Aar. 19. 108 (1968).’ ’ LflL) LInri. Rliiraoka. N.. Shitomi. (4.-, ~. , T.. H., Nippon khokuhin Kbgyo ’Gakkaishk 14, 187 (1967); Chem. Ahstr. 68, 2090g (1968). (41L) Nakanishi, K., Bull. Nat. Inst. Sci. India 31, 158 (1965); Chem. Ahstr. 66,28464 (1967). (42L) Kobuhara, A., ‘Vippon iVogeikagaku Kaishi 41, 354 (1967); Chem. Ahstr. 68, 21017e (1968). (43L) Ohlson, R., Persmark, U., Podlaha, O., J . Amer. Oil Chem. SOC.45, 475 (1968). (44L) Osada, H., Goto, I., Eiyo To Shokurvo 20. 391 (1968): Chem. Ahstr. . 69,980ax (1968). (45L) Schormueller, J., Claws, W., Z. Lehensm. Cntersuch. Forsch. 133, 65 (1967). (46L) Schormueller, J., Schubert, W., ihid., 136, 146 (1968). (47L) Singleton, V. L., Marsh, G. L., Coven. RI.. J . Aor. Food Chem: 14. 5 (1966). ’ (48L) Taylor, J. R., Blomquist, V. H., J . Ass. Ofic. Anal. Chem. 51, 533 (1968). (49L) Thompson, A. C., Hedin, P. A., J . Chromatogr.21,13 (1966). (5OL) Vercele, M., Claus, H., van Dyck, J., J . Inst. Brewing 73,298 (1967); Anal. Ahstr. 15, 5033 (1968). (5lL) Yamamoto, Y., Kumamaru, T., Hayashi, Y., Nobori, Y., Yakugaku Zasshi 87, 1346 (1967); Chem. Ahstr. 6 9 , 9 8 0 2 ~(1968). (52L) Zagrodzki, S., Kurkowska, A., Chcmia Analit. 12, 159 (1967); Anal. Ahstr. 15, 2266 (1968). . I
(8RI) Blom, L., Hendricks, P., Caris, J., Anal. Biochem. 21,382 (1967). (9M) Bobtelsky, M., Barzily, I., Anal. Chim. Acta 35,520 (1966). (1OM) Brown, D., Boyd, W. J. R., J . Inst. Brewing72,Ml (1966). (11RI) Bujard, E., Mauron, J., J . Chromatogr. 21,19 (1966). (12M) Carisano, A,, ihid., 27, 259 (1967). (13M) Cavallini, D., Graziani, 31. T., Dupre, S., Nature 212,294 (1966). (14M) Clayton, J. W., Cereal Chem. 43, 495 (1966). (15M) Decio, G., Latte 42, 105 (1968); Chem. Ahstr. 69,34718e (1968). (16hl) Deibner, L., Bayonove, C., Heredia, N., Chim. Anal. 47,512 (1965). (17M) Eisa, E. A., Zaki, hl., Ain Shams Sci. Bull. No. 10, 31 (1966); Chem. Ahstr. 69,7570213 (1968). (18M) Feibush, B., Gil-Av, E., J . Gas Chromatogr.5,257 (1967). (19M) Ganguli, N. C., Agarwala, 0. N., Bhalerao, Y. R., J . Dairy Sci. 48, 674 (1963). (20hI) Gehrke, C. W., Stalling, D. L., Sepn. Sci. 2,101 (1967). (21hI) Giddings, J. C., Keller, R. A., “Advances in Chromatography,” Vol. 2, &I.Dekker, New York, 1966. (22M) Hamm, R., Hofmann, K., Z. Lebensm. Untersuch. Forsch. 130, 85 (1966). (23M) Hamm. R.. Hofmann., K.,. ihid., 130, 133 (1966). ’ (24hI) Hantzsch, S., Prescher, K. E., Z . Anal. Chem. 213,408 (1965). (25M) Harada, K., Anan, T., Kii, IC., Yamada, K., Suisan Daiqaku Kenkyu Hokoku 16, 11 (1967); Chem. Ahstr. 69, 26100g (1968). (26hl) Heathcote, J. G., Washington, R. J., Analyst 92,627 (1967). (27M) Hofmann, K., Saturwissenschajfen 52, 428 (1963); Anal. Ahstr. 13, 62.52 (1966). (28M) Huebner, F. R., Wall, J. S., Cereal Chem. 43,32.5 (1966). (29M) Jain, &I. K., Tandon, R. N., Bhalerao, 5’. R., Indian J . Dairy Sci. 18, 134 (1965); Anal. Ahstr. 14, 2826 (1967). (30M) Jankiewicx, RI., Pomeranz, Y., J . Sci. Food Agr. 16,644 (1965). (31M) Jankiewicz, N., Pomeranz, Y., ihid., 16, 652 (196j). (32M) Kiermeier, F., Freisfeld, I., 2. Lehensm. Untersuch. Forsch. 128, 207 ( 196.5). (33M) Kiermeier, F., Petz, E., ihid., 131, 74 (1966). (34M) Kohler, G. O., Palter, R., U.S. Dep. Agr., ARS A‘o. 74-43,95 (1967). (35M) Kurahasi, K., Abood, L. G., Gombos, G., J . Chromatogr. 24, 264
(4611) Olivares, G. J., Aronow, L., Kerdel-Vegas, F., Acta Cient. Venez. 13, 9 (1967); Anal. Ahstr. 15, 2277 (1968). ~ ._, - .
(471.1) Pelletier, O., J . Agr. Food Chem. 14,496 (1966). (48.M) Quesnel, V. C., J . Chromatogr. 24, 268 (1966). (4931) Roberts, A. C., lIcWeeny, D. J., J . Food Technol. 2,233 (1967). (5OM) Ruhlmann, K., Michael, G., Bull. SOC.Chim. Biol. 47, 1467 (1965); Anal. Ahstr. 14,2727 (1967). (51M) Rutkowski, A., Chodkowska-Lossow, B., Chemia Analit. 10, 1023 (1965); Anal. Ahstr. 14, 1037 (1967). (52M) Satterlee, L. D., Lillard, D. A,, J . Food Sci. 32,682 (1967). (53M) Schenk, P., Scherz, R., Mitt. Geh. Lehensmittelunfcrs. u. Hyg. 56, 484 (1965). (5431) Schormuller, J., Grosch, W., Z. Lehensm. lintersuch. Forsch. 134, 162 (1967). (5511) Schwartz, A. N., Zabin, B. A., Anal. Bzochem. 14,321 (1966). (56M) Selim, A. S. XI.,J . Agr. Food Chem. 13,43.5 (1965). (5711) Senn, AI., Yenkataraghavan, R., McLaffertv. F. W.. J . Amer. Chem. Soc. 8 8 , 5593 (1966).’ (58M) Shemyakin, 11. 11. et al., ,Tuture 211.361 (1966). I - - \ -
- - I
(59i\?)Skodak, F. I., Wong, F. F., White, L. AI., Anal. Biochem. 13, 568 (196.5). (6011) Smith, E. D., Sheppard, H., Jr., __ iYature 208, 878 (1965). (6111) Smith, J. R. L., Waddington, D. J.. ANAL.CHI;%%.40. 522 (1968). (6211) ’Spies, J. R., J . ’Agr. Food Chem. 16, 514 (1968). (63M) Stack, 11. V., J. Gas Chromatogr. 5,22 (1967). (6411) Steaink, L. l),, Anal. Biochem. 20, 302 (1967). (65M) Stubchen-Kirchner, H., HoppeSeyGr’s Z. Physiol. Chem. 349, 1049 (1Y68). (6631) Sweeney, J. P., Simandle, P. A., Chemist Analyst 55, 31 (1066). (67311) Tsiigo, T., Iwaida, 11.,Kawaguchi, Y., J . Dazry Sci. 49,453 (1966). (6811) Vakaleris. 11. G., Pofahl, T. R., ihid., 51, 1.592 (1968). (6911) I‘alles, F. L., Rivas Ramos, F. J., Rodriguez, P. C., Rev. Fac. Quim., Univ. Sac. Mayor Sun ilfarcos Lima 18, 23 (1966); Chem. iihstr. 69, 66182s (1968). (7031) Waggle, D., Deyoe, C. W., Pomeranz, Y., J . Sei. Food Agr. 17, 269 (1966). (7131) Wheaton, T. A., Stewart, I., Anal. Biochem. 12,585 (1963). (7211) Yaguchi, >I., Tarassuk, X . P., J . Dairy Sci. 50, 1985 (1067). (7331) Zarkower, A., Dunlop, R. J., Norcross, N. L., Amer. J. Vet. Res. 26. 133Y (1963): Anal. Ahstr. 13, 5837 (1966). (74hI) Zhebrovskii, L. S., Pavlyuchenko, T. A., Zhivotnovodstvo 30, 69 (1968); Chem. Ahstr. 69,9776q (1968). I
Proteins, Amino Acids, and Nitrogen
( I l l ) Ammo, T., Mizukami, S., J . Pharm. SOC. Japan 85, 981 (1965); Anal. Ahstr. 14, 1582 (1967). (2hI) Anfinsen, C. B., Jr., Anson, LI.L., Edsal, J. T., Richards, F. M.,“Advances in Protein Chemistry, “Vol. 22, Academic Press, New York,, 1967. (3hI) Ashworth, U. S., J . Daary Sci. 49, 133 (1966). (4M) van Baal, J. P. W., Leget, J. N., Z . Lehensm. Untersuch. Forsch. 127, 263 (1965). (5hl) Barman, T. E., Koshland, D. E., Jr., J . Biol. Chem. 242,5771 (1967). (6x1) Biemann, K., Cone, C., Webster, B. R., Arsenault, G. P., J . Amer. Chem. SOC.88,5598 (1966). (7Rl) Blau, K., Darbre, A,, J . Chromatogr. 26,35 (1967). 88 R
ANALYTICAL CHEMISTRY
Anal. Chem. 223,263 (1966). (38Rl) Matsushita, S., Iwami, N., Anal. Biochem. 16,36.5 (1966). (39M) Merritt, C., Jr., Robertson, D. H., J . Gas Chromatogr.5,96 (1967). (40111) Miller, E. L., J. Sci. Food Agr. 18,381 (1967). (41M) Morozova, R. P., Ukr. Biokhem. Zh. 37, 290 (1965); Anal. Ahstr. 14, 308 (1967). (42M) Mussini, E., hlarcucci, F., J . Chromatogr. 20,266 (1965). (43hI) Narayan, K. A., Vogel, hl., Lawrence, J. hl., Anal. Biochem. 12, 526 (1965). (4411) Obah, T., Kimura, I f . , J . Food Sci. 32,531 (1967). (45M) O’Hara, C. E., J . Sci. Food Agr. 19,117 (1968).
,
Vitamins
(1N) Barbiroli, G., Ann. Fac. Econ. Commer., Univ. Studi Xessina 4, 167 (1966): Chcm. Ahstr. 68, 38187h (i(368j.’ (2N) Blattna, J., hlanoiiskova, J., Prumysl Potravin 18, 207 (1967); Anal. Abstr. 15,4308 (1968). (3X) Christianson, 1). I)., Wall, J. S., Ilimler, R. J., Booth, A. N., J. Agr. Food Chenk: 16, 100 (1968). (4N) Cornelius, J., Yang, H. T.,J . Gas Chromatogr.5, 327 (19G7).
( 5 5 ) Covello, M.,Schettino, O., Farmaco, Ed. Prat. 20, 581 (1965); Anal. Abstr. 14,2797 (1967). (6N) Deutsch, RI. J., Weeks, C. E., J . Ass. O f i c . Agr. Chcm. 48,1248 (1965). ( 7 s ) Dicks-Bushnell, 31. W., J . Chromatogr. 27,96 (1967). (8K) Drawert, F., Heimann, W., Ziegler, A,, 2. Anal. Chem. 217, 22 (1966); Anal. Abstr. 14,3576 (1967). ( 9 s ) Egger, K., Kleinig, H., ibid., 211, 187 (1965); Anal. Abstr. 13, 5883 (1966). (ION) Eisner, J., Iverson, J. L., Firestone, D., J . Ass. Offic. - Anal. Chem. 49. 580 (1966). (11s) Fel’dman, A. L., Kobeleva, S. &I., Konserv. Ovoshchesush. Prom. 23, 38 (1968); Chem. Abstr. 68, 1 1 3 4 5 2 ~ (1968). (12N) Fischer, R., Freise, G., Dt. ApothZtg. 106, 348 (1966); Anal. Abstr. 14,4301 (1967). (13N) Frazer, A. C., Lines, J. G., J . Sci. Food Agr. 18,203 (1967). (14N) Frodyma, RI. RI., Lieu, V. T., ANAL.CHIX. 39,814 (1967). (l5N) Fuertig, W., Pohloudek-Fabini, R., Pharmazie 20, 714 (1965); Anal. Abslr. 14, 1695 (1967). ( 1 6 s ) Fuertig, W., Pohloudek-Fabini, It., ibid., 21, 432 (1966); Anal. Abstr. 14,6435 (1967). (17pu‘) Gracian, J., Arevalo, G., Grasas Acezt. 16, 278 (1963); Anal. Abstr. 14,2264 (1967). (185) Harding, K,,J . Chromatogr. 24, 482 (1966). (19N) Ikeda, S., Taguchi, T., Kippon Suzsan Gakkaishi 32, 346 (1966); Chem. Abstr. 68,67848e (1968). (20N) Imanari, T., Tamura, Z., Chem. Pharm. Bull., Tokyo 15, 896 (1967); Anal. Abstr. 15,5579 (1968). (21N) Ionescu-Stoian, P., Cruceanu, I., RLISSLI, C., Ciupercescu, V.,Revta Chim. 17, 175 (1966); Anal. dbstr. 14, 4319 (1967). (22N) Ishikawa, S., Katsui, G., Vitamins, Kyoto 31, 445 (1965); Anal. Abstr. 13, 5882 (1966). (23N) Jaky, hl., Fette, Seifen, Anstrichmzttcl69,507 (1967). (245) Kaderavek, G., Prati, F., Riv. Ital. Sostanze Grassc 45, 138 (1968); Chem. Abstr. 69,1830g (1968). ( 2 5 s ) Knobloch, E., Cslka Farm. 16, 64 (1067); Anal. Abstr. 15, 2910 (1968). ( 2 6 s ) Komoda, U., Onuki, K., Harada, I., Agr. Bzol. Chem. 31, 461 (1967); Chem. Abstr. 67, 52846h (1967). (27N) Korytnyk,’ W., Fricke, G., Paul, B., Anal. Biochem. 17,66 (1966). (28N) Koziol, J., Cerna, J., Nartinovska, AI., Prumysl Potravin 16, 422 (1965); Anal. Abstr. 13,7144 (1966). (29N) Koziolowa, A., Chemia Analit. 11, 547 (1966); Anal. Abstr. 14, 5771 (1967). (30N) Koziolowa, A., ibid., 11, 691 (1966); Anal. Abstr. 14,7156 (1967). (31K) Lindberg, P., Acta Agric. Scand. 16, 217 (1966); Anal. Abstr. 15, 493 (1968). (32N) Nalysheva, A. G., Izv. Vyssh. Cchev. Zaved., Pishch. Tekhnol. 160 (1967); Chcm. dbstr. 68, 2071b (1968). (33K) hlaslowski, K., J . Chromatogr. 18,609 (1965).
(34s) hlurray, T. K., Day, K. C., Kodicek, E., Biochem. J . 98,293 (1966). (35N) Nadkarni. B. Y.. Mikrochim. Ichno. anulyt. Acta (5-6), 880 (1965); Anal. Abstr. 14,2271 (1967). (36N) Systrom, E., Sjovall, J., J . Chromatogr. 24,212 (1966). ( 3 7 s ) Ostrowski, W., Zak, Z., Krawczyk, A., Acta Biochim. Pol. 15, 241 (1968); Chem. Abstr. 69, 58441% (1968). (38N) Parrish, D. B., J. Ass. Ofic. Anal. Chem. 49,1066 (1966). (39s) Pasalis, J., Bell, X. H., J . Chromatogr. 20,407 (1965). ( 4 0 s ) Pawar, S. S., Mager, N. G., Fish. Technol. (Ernakulam, India) 11, 180 (1965); Chem. Abstr. 68, 2063a (1968). ( 4 1 s ) Petrova, E. A., Ulanova, N. A., Voop. Pitan. 24, 57 (1965); Anal. Abstr. 14,3619 (1967). ( 4 2 s ) Pohloudek-Fabini, R., Fuertig, W., Pharmazie 21, 358 (1966); Anal. Abstr. 14,6435 (1967). (432;) Popova, Y., Popov, K., Ilieva, &I., J . Chromatogr. 21, 164 (1966); Anal. Abstr. 14, 2859 (1967). (44N) Popova, Y. G., Popov, K., Ilieva, >ibid., I.,24,263 (1966). ( 4 5 s ) Prosser, A. R., Sheppard, A. J., J. Pharm. Sci. 57,1004 (1968). (46X) Richter, J., Ropte, D., Pharmazie 21, 495 (1966); Anal. Abstr. 14, 7793 (1967).
(47N).Richter, W., Vecchi, &I Vetter, ., W., Walter, W., Helv. Chim. Acta 50, 364 (1967). (48s) Roughan, P. G., J . Chromatogr. 29, 293 (1967). (49N) Schillinger, A., 2. Lebensm. Untersuch. Forsch. 129,65 (1966). ( 5 0 s ) Schmandke, H., Gohlke, H., ibid., 132,4 (1966). (31s) Schmidt, H. E., Fette, Seifen, Anstrichmittel 69,913 (1967). (525) Schorderet, M., Kapetanidis, I., Mirimanoff, A,, Pharm. Acta Helv. 41, 293 (1966); Anal. Abstr. 14, 5718 (1967).
(53Nj &hulz, E. P., Guadalupe Sanchez, M. R., Revta SOC.Quim. Mez. 11, 117 (1967); Anal. Abstr. 15, 6262, (1968). (54s)Searles, S. K., Armstrong, J. G., Can. Inst. Food Technol. J . 1, 1 (1968). (55N) Slover, H. T., Shelley, L. M., Burks, T. L., J . Amer. Oil Chem. SOC. 44,161 (1967). ( 5 6 s ) Spanyar, P., Petro, Ma, 2. Lebensm. Untersuch.Forsch. 137,163 (1968). ( 5 7 s ) Sturm, P. A., Parkhurst, R. M., Skinner, W. A., ANAL.CHEM.38, 1244 (1966). (58N) Tsugo, T., Yamauchi, K., Kanno, C., 1Vippon Nogei Kagaku Kaishi 42, 367 (1968); Chem. Abstr. 69, 58406c (1968). ( 5 9 s ) Uchman, W., Chemia Analit. 11, 91 (1966): Anal. Abstr. 14, 2860 (1967). (60N) Usher, C. D., Favell, D. J., Lavery, H., Analyst 93, 107 (1968). (61s) Vecchi, M., Vetter, W., Walther, W., Jermstad, S. F., Schutt, G. W., Helv. Chim. Acta 50, 1243 (1967). (62N) Vecchi, &Kaiser, I., K., J . Chromatogr. 26,22 (1967). (63s) Vioque, A., Albi, T., Albi, M. A., Grasas Aceit. 17, 172 (1966); Anal. Abstr. 14, 7895 (1967). (64N) Whittle, K. J., Pennock, J. F., Analyst 92,423 (1967).
(65N) Wisser, K., Heimann, W., Fritsche, C., 2. Anal. Chem. 230, 189 (1967); Anal. Abstr. 15,6261 (1968). Miscellaneous
(1P) Borker, E., Sloman, K. G., Foltz, A. K., ANAL.CHEM.39,75R (1967). (2P) Cameron, A. G., J. Food Technol. 2,223 (1967). (3P) Chiantella, V., Ann. Fac. Econ. Commer., Univ. Studi Messina 4, 49 (1966); Chem. Abstr. 68, 103997~ (1968). (4P) Chiantella, V., Licastro, F., ibid., 4, 295 (1966); Chem. Abstr. 68, 38355m (1968). (5P) Covello, M., Schettino, O., Farmaco, Ed. Prat. 21, 145 (1966); Anal. Abstr. 14,4284 (1967). (6P) Dalgliesh, C. E., Chem. & Ind. 1966, 2187. (7P) Danek, J., Hospadar, M., Prumysl Potravin 17, 578 (1966); Chem. Abstr. 66.18146 (1967). (8P)‘Eisenbrand, J., Deut. Lebensm. Rundschau 62,327 (1966). (9P) Ferren, W. P., Shane, S. A., J. Ass. Ofic. Anal. Chem. 51, 573 (1968). (lop) Graham, H. D.. Nature 207. 526 (196d). (11P) Hadorn, H., Zurcher, K., Mitt. Gebiete Lebensmitt. Hyg. 56, 491 (1965); Anal. Abstr. 14,2232 (1967). (12P) Johnson, A. R., J . Ass. Ofic. Anal. Chem. 50,857 (1967). (13P) J. Assoc. Offic. Anal. Chemists., “Changes in Official Methods of Analysis Made at the Eightieth Annual Meeting of the Association of Official Analytical Chemists, October 1966,” J . Ass. 0 8 c . Anal. Chem. 50, 190 (1967). (14P) Kleinert, J., Habegger, M., Rev. Intern. Chocolat. 23,256 (1968). (15P) Kohn, R., 2. Lebensm. Untersuch. Forsch. 129.28 (1966). (16P) Kohn, ’R., ‘Laufer-Heydenreich, S., ibid., 129, 92 (1966). (17P) Kramer, A., Twigg, B. A., “Fundamentals of Quality Control For The Food Industry,” Avi Publishing Co., Inc., Westport, Conn. 1966. (18P) Pinnegar, M. A., J . Inst. Brewing 72, 366 (1966); Anal. Abstr. 14, 7146 (1967). (19P) Senanayake, U. M., Wijesekera, R. 0. B., Rev. Intern. Chocolat. 23, 214 (1968). (20P) “Standard Methods for the Examination of Dairy Products,” American Public Health Association, New York, N.Y., J967. (21P) “Technicon Symposia on Automation in Analytical Chemistry. Sew York City, U.S.A. October 1966; Paris, France, November 1966,” Mediad Inc., White Plains N.Y., 1967; Anal. Abstr. 15,2452 (1968). (22P) “Third International Colloquium on the Chemistry of Coffee. Trieste, Italy, June 1967,” Anal. Abstr. 15, 5826 (1968). (23P) Zawadzka, J., Kozlowska, A., Roszkowski, W., Przemysl Spozywczy 20, H.2, 38 (1966); Chem. Abstr. 65, 17608 (1966). (24P) Z. Anal. Chem., “Modern Analytical Methods in Food and Biological Chemistry,” 2.Anal. Chem. 212, (1965); Anal. Abstr. 13,6061 (1966).
VOL. 41, NO. 5, APRIL 1969
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