(265) Thomas, J. P., Fallavier, M., &chard, A., Badia, M., Final Rep. DGRST Contract No. 7371545, 1975, 19 pp (World Alum. Abstr., 76:72-0085). (266) Thompson, D. E., Danchik. R. S., Anal. Lett., 1975, 8 (IO), 699 (Chem. Abstr., 84: 78582~). (267) Thonstad, J., Light Metals, Proc., 103rd AlME Annu. Meet., 1974 (Pub. 1974), 137 (Chem. Abstr., 81:173477m). (268) Tikhonov, V. N., “Analytical Chemistry of Magnesium.” (Analytical Chemistry of the Elements), Nauka, Moscow, USSR, 1973 (Chem. Abstr., 81: 72270h). (269) Tikhonov, V. N., Budnichenko, V. A,, Zh. Anal. Khim., 1974, 29 (5), 868 (Chem. Abstr., 81: 855579). (270) Tikhonov, V. N., Terent’eva, L. F., Karnaukhov, 0 . G., lzv. Vyssh. Uchebn. Zaved., Khim Khim. Tekhnol., 1975, 18 (6), 1004 (Chem. Abstr., 83:187940k). (271) Tikhonov, V. N., Yarkova, L. V., Zavod. Lab., 1975, 41 (lo), 1180 (Chem. Abstr., 84: 115419~). (272) Tikhonov, V. N., Budnichenko, V. A., lzv. Vyssh. Uchebn. Zaved, Khim. Khim. Tekhnol., 1975, 18 (7), 1169 (Chem. Abstr., 84:11862t). (273) Tikhonova, 0. K., Otmakhova, Z. I., Egorova. L. L., Kataev, G. A,, Tr. Tomsk. Gos. Univ., 1973, 249, 69 (Chem. Abstr., 83:52770j). (274) Turulina, 0. P., Zakhariya, N. F., Zh. Anal.
Khim., 1973, 28 (9), 1754 (Anal. Abstr., 28: 1B 10 1). (275) Turulina, 0. P., Zakhariya, N. F., Zh. Pfkl. Spektrosk., 1974, 21 (2), 203 (Chern. Abstr., 82: 38170m). (276) Vandecasteele, C., Speecke, A,, Hoste, J., Eurisotop Off. Inf. Book/., 1972, 68, 55 pp (Chem. Abstr., 83:187835e). (277) Vandecasteeie, C., Goethals, P., Kieffer, R., Hoste, J., Bull. SOC.Chim. Belg., 1975, 84 (6), 673 (Chem. Abstr., 83:212167y). (278) Vasilevskii, V. L.. Tolstousov, V. N., Nikolaev, V. V., Metetooy Issled. Opred. Gazov Met., 1973, 48 (Chem. Abstr., 83:107697y). (279) Vasilikiotis, G. S.,Kouimtzis, T. A,, Vasiliades, V. C., Microchem. J., 1975,20(2), 173(Anal. Abstr., 30:2B59). (280) Verdizade, N. A. Shiralieva, S. M., Azerb. Khim. Zh., 1974, (4), 109 (Chem. Abstr., 83: 37114e). (281) Verdizade, N. A. Shiralieva, S. M., Azerb. Khim. Zh., 1975, ( I ) , 126 (Chem. Abstr., 83: 172 134b). (282) Vicentini, V., Alluminio, 1975, 44 ( I ) , 37 (Chem. Abstr., 83:201546v). (283) Walsh, J. M., Metall. Trans., 1974, 5 (9), 2104 (Chem. Abstr., 81:145322p). (284) Ward, A. G., Nauchn. Tr,, Tashk. Gos. Univ., 1970, 379, 172 (Chem. Abstr., 81:130523f). (285) Watanabe, K., Kawagaki, K., Bull. Chem.
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Essential Oils and Related Products Ernest Guenther, Gilbert Gilbertson,“ and Roman T. Koenig Fritzsche
Dodge &
Olcott Inc., New York, N. Y. 100 1 1
This sixteenth review of the analysis of essential oils and related products covers the literature from September 1974 to August 1976, inclusive. It follows the general pattern previously established by the authors (225). As before, we have attempted to include all papers dealing directly with the analysis of essential oils, and a representative number of those dealing with related products. Analytical investigators were constantly delving more deeply into the chemical composition of essential oils. The same techniques were employed as in previous years, though they were frequently modified for adaptation to specific problems. Gas chromatography, together with mass spectrometry and other instrumental methods, was most frequently employed. High pressure chromatography was used more often than in former years for the separation of less volatile components, and in other special situations. The methods used are often not mentioned in this review, since the reader can generally surmise which techniques were employed, or he may refer to the original article when required. Official Compendia. The “Second Supplement to the Food Chemicals Codex Second Edition” was issued by the National Academy of Sciences (406). I t contains detailed official analytical procedures as well as new monographs and modifications of previous specifications. Books a n d Articles. Opdyke (420-424) published numerous monographs on fragrance materials, summarizing present knowledge of their safety in use or their toxicity in respect to sensitization and irritation. In a newly published “Handbuch der Aromaforschung”, the composition of bread aroma was reported in detail by Rothe (485). General Procedures. Procedures for the evaluation of capsicum, ginger, black pepper, turmeric, and paprika oleoresins were described by Salzer (499). A potentiometric method was described by Rik et al. (476) for determining minute quantities of essential oil obtained from various plant parts. Bruns (75) used a calibration curve to estimate the amount of perfume oil in soaps. Gas-liquid chromatography theory, as applied to the study of essential oils, was discussed by Di Corcia et al. (148) and
illustrated by a method employing a new type of graphited C block. Karlsen and Siwon (299) showed that a change in temperature can produce a change in the sequence of the elution peaks of compounds belonging to different chemical groups. Kugler et al. (327) arrived at an optimal compromise between reproducibility and analytical time based on computer analysis of temperature programmed gas chromatography using glass capillary columns. Koksharov (315) used a flame ionization detector for the determination of the essential oil directly from fresh plant samples. A modified injection system, permitting more simple determination of perfume oils in soaps and similar materials, was described by Burrell (80). Huntoon (265) reviewed gas chromatographic methods for quality control of flavoring materials. Massaldi e t al. (371) presented a method for determining volatiles by vapor headspace analysis in a multiphase system. The method employs controlled dilution and correction for extraction by the added phases. Gostecnik and Zlatkis (219) evolved a computer evaluation of gas chromatographic profiles of cold pressed orange oils which rated the oils as to quality. The ratings thus obtained agreed with the rating assigned to the oils by a number of essential oil experts. Merritt et al. (379) utilized a computer for acquiring and processing data from several gas chromatography-mass spectrometry analytical systems. The system, as described, accorded special emphasis to data encoding techniques and component identification. Srinivas and Borecki (537) identified unknowns by computer matching of gas chromatographic-mass spectral data of known compounds. Salient features of an unknown spectrum enabled the authors to postulate a reasonable chemical structure. Bruhn (74) gave numerous examples of artifacts which may be formed during the gas chromatography of essential oils. Haarse (235) used hydrogenation and hydrogenolysis to identify sesquiterpenes by the C skeleton technique. Thin-layer R f values were given by Paseshnichenko et al. (433) for many essential oil components in several different solvents systems. Sen et al. (507) developed a thin-layer method for identifying oils of caraway, coriander, and cumin in mixtures. Mancini (365) used thin-layer chromatography for the quantitative assay of the main components in essential ANALYTICAL CHEMISTRY, VOL. 49, NO. 5, APRIL 1977
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oils. A method for the detection of polybutene contamination in volatile oils using low-temperature thin-layer chromatography was conceived by Briggs and McLauglin (70). Lee and Chang (346)developed a very involved and complex high-pressure liquid chromatographic method employing repeated chromatography using different conditions to separate less volatile components. High pressure liquid chromatography was adapted by Ross (480) to the separation of the components of cinnamon oils. The method is sufficiently simple to be considered for routine quality control. A comparative study of methods of computer matching mass spectra was conducted by Mathews and Morrison (373). The matching of 6 to 8 of the most intense peaks in each spectrum was necessary to give the best results. Erni et al. ( 177) devised a sophisticated computer assisted mass-spectra interpretation system which emphasizes the finding of structurally similar compounds even if identical spectra are not in the file. Kravchenko and Rik (322)found that photoionization mass spectra gave more intense peaks than ordinary mass spectra. A combination of pyrolysis, gas chromatography, and mass spectrometry was employed by Boss and Hazlett ( 6 1 )to identify isomeric alcohols and ketones. A computer system for identifying the structure of organic compounds from their IR, UV, PMR, 13C NMR, and mass spectral data was designed by Naegeli and Clerc (396). A Fourier transform spectrometer was used to record IR spectra of dilute vapors by Low et al. (355).The technique is an order of magnitude more sensitive than conventional methods, and, since it was done at room temperature, should be useful for heat sensitive materials. Conformational studies of monoter enes were conducted by Holden and Whittaker (255)using C NMR spectrometry. Bohlmann et al. (60) examined the 13C NMR spectra of 97 monoterpenes and showed their usefulness for characterization. Begley et al. ( 4 5 )employed x-ray analysis to establish the structure of a chrysanthemate. The ORD and CD spectra were compared with those of six naturally occurring pyrethrin esters. The percentage composition of dill oil was determined by Baslas and Baslas ( 3 7 ) ,using polarography. Employing the same method with a Hg dropping electrode for determining the electroreduction of the oils, Shavgulidze et al. (515)analyzed rose, geranium, and sweet basil oils. The volatility coefficients of essential oils and perfumes were calculated by Mueller (394) based on weight loss from a blotting paper. Sturm and Mansfeld (548) investigated the evaporation of perfume oils and ascertained the quantitative effect of fixatives on the rate of evaporation. Essential Oils-General. The main components of several unusual essential oils from plants growing in Brazil were identified by De Alencar et al. (127).Similar work, relating to three plants from the state of Rio de Janeiro, was published by Alpande de Morais et al. (16).Zola and LeVanda (628,629) examined oils of geranium, immortelle, fennel, eucalyptus, cudweed, and inastic from Corsica. They reported the oils to be of excellent quality. Several flavoring isolates were obtained from the oils from plants growing in Ecuador by Paredes (429). Virmani and Datta (600)examined various essential oils from the Lucknow district in India; Favre (180) analyzed several unusual oils from Latin America; and Peyron (441) determined the composition of several commercial oils from Mato Grosso. Individual Essential Oils. Among other components, azulene was reported in oil of Achillea asiatica by Kalinkina and Berezovskaya (278). The oxygenated monoterpenes in A. fillipendulina oil were more identified by Dembitskii et al. (136), and Calvin0 et al. ( 9 2 ) found 21 components of A. moschata oil. The composition of oil from Agastache rugosa herb was explored by Fujita and Fujita (197, 198),who found it to be very similar to that from Mosla methylchavicolifera and Dostulated a Darallel evolutionary development of essential bil in both plants. In the oil of A m t h i s australis, Brims et al. (72) identified several new components, one of them,-isopimara-8,15-diene, for the first time in nature. Borneol and camphor were the main components, among many identified by Sharipova et al. (514)in Ajania fastigiata oil.
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Twenty-seven species of Allium were classified by Freeman and Whenham (193) in accordance with their content of (S)-1-propenyl-,( S )-2-propenyl, and ( S )-methyl-L-cysteine sulfoxide as flavor precursors. Kameoka and Miyake (285) identified the sulfides and linalool in the leaf oil of Allium tu berosum. 2,5-Dimethyl-4-hydroxy-3(2H)-furanone seemed to make the greatest contribution to the aroma of roasted almond of the h a n y constituents identified by Takei et al. (553, 554). Oil of Aloysia gratissima was investigated by Bravo et al. (65,66). De Riscala et al. (140) identified the major components of oil of A . lycioides, and Huergo and Retamar (262, 263) did the same with oil of A. polystachia. Linalool was most plentiful of the inain components in oil of Alstonia scholaris reported by Gupta and Chandra (227). The major monoterpene hydrocarbons from A m o m u m xanthioides were identified by Le Tung Chau (349);the major components of oil of Amorpha fruticosa were reported by Popescu et al. (454);and those from oil of Anaphalis contorta by Sinha et al. (528). The composition of the volatile constituents of angelica root oil obtained by extraction with ether-pentane and with alcohol-water was investigated by Taskinen and Nykanen (561, 563), and a new component cis-a-copane-8-01was characterized. Lawrence and Morton (342) identified acorenone B and many other components in oil of Angelica lucida. The essential oils from various Aniba species were classified into three groups, linalool, benzoate, and allylbenzene by Alpande de Morais et al. ( 1 4 ) . Anise seed oil from plants grown in Albania was described by Gliozheni (215).Kubeczka et al. (325) isolated and characterized the hitherto unknown 4-methoxy-2-(trans-l-propenyl)pheny1-2-methyl butyrate from anise oil. Tabacchi et al. (550) identified three sesquiterpenes, including y-himachalene in Anisum vulgare seed oil. Bricout (68)reported nine new components in the high-boiling fraction of oil of anise star. Eighty-one constituents of apple volatile components, 25 of which had not previously been reported, were found by Bermejo and Saura Calixto ( 5 1 ) . Dirinck (160) identified many volatile constituents of “Granny Smith” apples. Many terpene components of the oil from Araucaria araucana were characterized by Briggs and White ( 7 3 ) ,and Bartley et al. (36) similarly investigated the oil of A. heterop h y 11a. The compositions of leaf oils of the Aroliaceae and Lauraceae families were elucidated by Hayashi et al. (241). Artemisia Annua oil contains artemisia ketone, menthol, and ilangen according to Toleva et al. (583).Azulenes, among other components, were found in A. argentea by El-Moghazy Shoaib et al. (174). Along with other components, azulene was also extracted from oil A. macrocephala by Dudko et al. (162).A. santonica was shown by Rubstov et al. (490)to be a valuable source of citral, and Usynina et al. (592)reported the presence of certain phenols in several Artemisia oils. The absolute configuration of the 2-butyl propenyl disulfides from asafetida was established by Kjaer et al. (312),and the composition of the volatile oil of asafetida from Afghanistan was elucidated by Mahran et al. (363). Endo et al. ( 1 75,176)characterized nine new sesquiterpenoids from the oil of Asarum caulescens, which is related to Canadian snakeroot. Among 30 components identified by Kameoka et al. (288) in the oil from Astragalus sinicus, the main one was o-benzyltoluene. Oil of sweet basil from plants grown in India was shown by Pushpangadan et al. (462)to consist of three chemotypes, and this was the reason for its relatively poor quality. Karawya et al. (296)distinguished oils of Ocimum basilicum (sweet basil) and 0. rubrum grown in Egypt by their quantitative compositions. Kekelidze and Beradze (305) found that the nonphenolic portion of basil oil was composed of about 23 substances which were identified. Manitto, Monti, and Gramatica (367)traced the biosynthesis of eugenol in basil. Teisseire and Galfre (567)found that certain basil oils were adulterated with ylang-ylang oil. California bay oil was investigated by Buttery et al. (82)who confirmed many previously reported components and characterized an additional 26. McHale et al. (359)found the main
Ernest Guenther, born in Munich, Germany, attended the Technische Hochschule there as well as the University of Munich. He took his Ph.D. at the University of Zurich in 1920. Associated with Fritzsche Dodge & Olcott, Inc., since 1924, he recently retired as Executive Vice President and Technical Advisor of the company. An expert in the field of essential oils, Dr. Guenther has published approximately 150 papers in various scientific journals and is author of six volumes of "The Essential Oils." His American Chemical Society activities include numerous lectures before local chapters throughout the United States and Canada.
Gilbert Gllbertson is Technical Advisor for International Operations at Fritzsche Dodge & Olcott, Inc., directing the flow of technical information to the foreign divisions. He is also concerned with patent applications, foreign food laws, and biological testing. He is a member of tlhe Fritzsche-D&O Quarter-Century Club and in the past has held various positions with the company in production, the Flavor Laboratories, the Analytical Laboratories, and research and development. Serving in the U.S. Navy, he studied electronics at the U.S. Naval Research Station in Washington, D.C. He studied chemistry at Pratt Institute, Brooklyn, N.Y., and received his B.S. from Seton Hall University, South Orange, N.J.
Roman T. Koenlg has been in charge of Technical Information and the Libraries at Fritzsche Dodge & Oicott, Inc., since 1959. He is also Editor of the Fritzscht?-D&O Library Bulletin, a monthly publication comprising current technical articles, which services the essential oils, perfume, and flavor industries all over the world. Previously. Dr. Koenig was a member of the staff of the Technical Information Division of Esso Research and Engineering Co., and prior to that he had been engaged in physicochemical research in industry and taught at universities both in the United States and England. Born in Poland, he obtained his Ph.D. in chemistry in 1946 at the Imperial College of Science and Technology of the University of London. He is a member of the American Chemical Society.
difference between anise-scented bay oil and lemon-scented bay oil is that the former contains methylchavicol and methyleugenol, while the latter contains neral and geranial. The volatile components from dry red beans were investigated by Buttery e t al. (83).Many oxygenated and sulfur- or nitrogen-containing compounds were identified. The chemical and physical properties of Italian bergamot and mandarin oils were reviewed by Di Giacomo (151).Liberti and Goretti (351,352) compared gas chromatographic analysis of whole bergamot oil with headspace analysis and found that only about half of the 300 components present could be detected in the vapors. They also correlated gas chromatograms of different bergamot oils with variations in odor quality. Di Corcia et al. (147) experimented with different gas chromatography columns and carriers applied to the analysis of bergamot oil, and Di Giacomo and Calvarano (153) resolved oil bergamot into seven fluorescent components by thin-layer chromatography. Calabrio and Curro (86) described rapid and simple spectrofluorometric procedures for separating and determining coumarins in the oil, and Carmona et al. (97) employed infrared spectroscopy to determine certain components of bergamot oil. Hogg et al. (254) described the IR and NMR spectra of cis- and trans-P-bergamotene. Di Giacomo et al. (152) made a detailed study of the peroxide index of bergamot oil and suggested normal limits. Some main constituents of oil of bergamot-mint were as-
sayed by Paris et al. (431) who also suggested uses for the oil. About 55% cinchol, a sesquiterpene alcohol, was found in oil of Blepharacalyx giganteus by Bravo and Retamar (67).
Among the volatiles from blueberries, Parliment and Kolar
(432) found a predominance of CScompounds including sat-
urated and unsaturated aldehydes and alcohols. The characteristic odor of arctic bramble was shown by Honkanen et al. (258) to be largely due to 2,5-dimethyl-4methoxy-2,3-dihydro-3-furanone. Kallio (279) confirmed this and also identified many other constituents. The compositions of two types of buchu oil were reviewed by Blommaert (53). Several d-alkylvalerolactones were found by Kameoka et al. (284) to be important elements of butter flavor. Calamus root oil was obtained in a yield of 8.5%by extraction with petroleum ether followed by distillation, compared with a yield of 3.2% by distillation alone, as reported by Singh et al. (526). The chemical constituents of Callistemon lanceolatus oil were investigated by Bhagat (52), and Wasicky and Saito (608)found cineole to be the major component of C. speciosus oil. The essential oils of Calyptranthes species investigated by Alpande de Morais et al. (15) contained neral and methylchavicol. Takaoka et al. (552) elucidated the composition of the sesquiterpene fraction of camphor oil, and Fujita et al. (200) analyzed the oil from the shoots of the camphor tree, Cinnamomum doederleinii. Duve et al. (166) showed that the composition of oil from Cananga odorata growing in Fiji was different from ylangylang oil from the cultivated tree. Exhaustive investigations of the composition of oils from the bark, wood, and fruit of Canarium album were conducted by Kamoeka et al. (280, 281,287). Newly discovered components of oil of Cannabis sativa were described both by Paris (430) and Hendriks et al. (244).
A quantitative column chromatography assay was run on oil of caraway by Razdan and Koul (466). Benecke (49) demonstrated that gas chromatography was a more accurate method for determining carvone than the oxime titration method. Rothbaecher and Suteu (483,484) showed that carvenone, perillyl alcohol, and carvacrol occur in caraway oil only as artifacts. Chou (111) reported the major components in the oil, and found C8 and Cg aldehydes for the first time. The composition of cardamom seed oil was investigated by Miyazawa and Kameoka (387),employing a combination of instrumental methods. Many components were identified. Lewis et al. (350)demonstrated that to get the complete flavor of cardamom it was necessary to add an extract from the steam distilled exhausted seeds to the distilled oil. The seed oils from seven varieties of carrots were compared by Strzelecka and Soroczynska (546, 547), who identified numerous components. Cheema et al. (108) demonstrated the presence of daucol, carotol, and a sesquiterpene oxide. Alabran et al. (12) identified many aroma components of carrot and devised a scheme to indicate their relation to the total aroma. Two new components of cascarilla oil were characterized by Claude-Lafontaine et al. (117). The composition of the flower oil of cassie from Egypt was investigated by El-Gamassy and Rofaeel (171,172).They also checked the oil yield from flowers gathered at different times of day. The structure of cis-nepetalactone, isolated from capnip oil, was established by Eisenbraun e t al. (169). The stereochemistry of several new components found in cedarwood oil was established by Adams et al. ( 7 ) .Similarly, Teisseire and Plattier (569) characterized a new bicyclic sesquiterpene ketone, and Plattier and Teisseire (450, 451) elucidated the stereochemistry of several other sesquiterpenes isolated from oil of Atlas cedar. Adams et al. ( 9 ) isolated a new ketone from the oils of Atlas and Himalayan cedarwood, and Singh et al. (527) reported greatly increased yields of oil from Himalayan cedarwood by extraction followed by distillation. The oil from celery leaves was investigated by Fehr (181), ANALYTICAL CHEMISTRY, VOL. 49, NO. 5, APRIL 1977
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Stankeviciene et al. (542),and Kichanova and Moskalenko h h o identified several new terpenes not previously found in (313) studied the effect of preplanting y-irradiation on the celery. quantity and composition of coriander oil. Verzar-Petri et al. (595,596)described methods for assaying Main components of corn bud essential oil were identified several components of chamomile oil, including thin-layer by Thompson et al. (579),and the volatile constituents of chromatography to determine chamazulene, direct photomsweet corn flavor were identified by Ishii et al. (268),who also etry, and gas chromatography. Nan0 et al. (405) analyzed indicated some chemical changes responsible for the off-flavor Roman chamomile oil and identified many constituents, indeveloped during storage. cluding angelic acid esters. The composition of chenopodium botrys essential oils from Benzyl cyanide was shown by Acosta de Iglesias et al. ( 4 ) to be the main component of the volatile oil Coronopus ditrees in different parts of Kazakhstan proved to be qualitatively identical, and Rustembekova et al. (496)identified 12 dymus. components in the oils. Retamar et al. (470, 471) found 80 Counter current extraction was employed by Mathur and peaks in the gas chromatography of oil of C. pumilio, and Bhattacharyya (374) in the investigation of costus root oils identified several components. of Kashmir and Punjab origin. Costunolide and several other The oils from Chrysanthemum boreale, C. makinoi, and components were reported. Klein (314)characterized two new C. japonense were investigated by Matsuo et al. (375, 376), constituents of costus oil, dihydroaplotaxene and 3,9,11who identified many components and established the strucguaiatriene-12-carboxylicacid. ture of nojigiku alcohol. Kameoka et al. (283) analyzed C. The relation between chemical composition and odor imcoronarium oil and characterized a new component, transpact of cumin was researched by Tassan and Russell (564)who 2-(hexa-2,4-diyn-l-ylidene)-1,6-dioxaspiro[4.4]non-3-ene.found that variations in four aldehydes particularly 3 - p Dimitrov and Nikolova (159)examined the steam distilled oil menthen-’l-al, had a pronounced effect on the odor. from C. indicum. Forsen and Von Schantz (185)distinguished Fractionation and gas chromatography were used by Briggs different chemotypes among oils of C. uulgare from various and Kingsford ( 7 1 )to identify terpene components of oil of locations in Finland. Cupressus macrocarpa. Oils from the cones and the leaves of Essential oils of cinnamon, both natural and so-called naC. torulosa, Himalayan cypress, were analyzed by Sinha and ture-identical, were compared by Zuercher et al. (631). No Prakash (529). significant correlation was found between gas chromatoRao and Nigam (465)reported the quantitative composition graphic analysis and odor and flavor. Wijesekera et al. of Curcuma aromatica oil, and Mitra (384) reported that of oil of C. longa. (612-614) described a rapid IR estimation of the main components in cinnamon leaf, stem bark, and root bark oils. They The chemistry of some essential oils from Cymbopogon used gas chromatography to identify many components of species was elucidated by Banthorpe et al. (34).Proenca da these oils and to note certain differences in composition, and Cunha et al. (455, 457,458) identified many components in also investigated a rare variety of cinnamon oil containing lioil of Cymbopogon densiflorus. nalool, eugenol, and cineole. Herisset et al. (245) continued Several new components of the oil of Algerian cypress were and extended their studies of cinnamon Ceylon and cassia oils, structurally characterized by Tabacchi et al. (551), using a different analytical technique and a new gas chroThe stereochemistry of nordavanone, isolated from oil of matography column which achieved better separation, espedavana, was clarified by Thomas et al. (577, 578). They also cially of hydrocarbons. Angmor et al. (22)found that oil from established the configuration of davanone. young bark had more cinnamyl acetate and less cinnamalOsisiogu (425) found 25% of 0-phenylnitroethane in the dehyde than oil from old bark. An oil distilled from cinnamon essential oil of dennettia. saigon root was analyzed by Kameoka et al. (289).Mane and Kozhin et al. (320)used liquid-liquid chromatography to Rao (366) characterized a phenolic sesquiterpene isolated separate components of Dictamnus gymnostylis oil. A new from oil of Cinnamomum xanthorrhiza, and Lawrence and ether, dictagymnin, was the main constituent. Hogg (340) analyzed the oils from two species of CinnamoThirty-six components of dill seed oil were identified by mum growing in the Philippines. Miyazawa and Kameoka (386).Zlatev and Balinova-TsvetCitronella oil which had been subjected to gamma radiakova (627)investigated the oil content of various parts of the tions was found by Pande and Gupta (428)to contain two new dill plant at different stages of development, and Chubey and carbonyl compounds, one at 30%, and to be changed chemiDorrell (112) reported on the yield and quality of dill oil produced in Manitoba. cally in many respects. Gas chromatographic analysis of the carbonyls, first sepaThe oils of two varieties of dragons head were analyzed by rated as 2,4-dinitrophenyl hydrazines, and alcohols, first Kubrak and Zhitarchuk (326).One contained mainly citral, separated as benzoyl derivatives, were conducted by Pias and the other limonene. A new phenolic sesquiterpene was isolated from Elvira biGasco (444, 445) on volatiles from the juices and rinds of several citrus species. Moshonas and Shaw (393) developed flora oil, and its structure was established by Dennison et al. (138). a rapid bromate titration method for evaluating citrus essence. The aldehyde components of several citrus oils were assayed Gusakova and Umarov (233) found a new C18 acid and phthalate in oil of Eremostachys molluceloides. by Carro de la Torre et al. (103).Kekelidze and Beradze (304) evaluated the composition of several citrus oils from the The composition of oil of Eryngium foetidum was eluciGeorgian SSR. Scora (505) discussed the variations in citrus dated by Yeh (620). oil composition and the many reasons for them. Fujita and Several components of oil of Eucalyptus camaldulensis Yamashita (194) found 24 new components in oil of Citrus were identified by Gunay (226). The essential oil of E. cidepressa, including 3-hexenol and thymol, and Ubertis and triodora from plants gowning in the Tucuman province was Carretto (588) contributed new conclusions, based on IR analyzed by Argiro and Retamar (24). Garcia-Vallejo and spectroscopy data, relating to the isomerism of citral in citrus Garcia-Martin (209,210)also reported their investigation of oils. E. citriodora oil, as well as a quantitative analysis of E. maThe essential oil of clementine from fruit grown on the carthuri oil. They (207,208)also examined the oils from two Rosarno plain was analyzed by Calvarano et al. (89). Its eucalyptus species acclimated in Spain, E . elaephora and E. quantitative composition was determined. sideroxylon. Nizharadze and Bagaturiya (412) reported that Extensive research in the composition of coffee aroma was the oil from Gruzian eucalyptus plants contains a maximum conducted by Vitzthum and Werkhoff (601, 603), who reof 55% eucalyptol. Proenca da Cunha and Cardoso do Vale ported for the first time 17 alkylated 5 - and 6-membered ali(459) separated cineole of 96% purity by freezing of oil of cyclic pyrazines, 20 oxazoles, 23 thiazoles, and many other Portuguese E. globulus, followed by washing of the cryscomponents. Kung (329)identified a pleasant buttery caramel tals. aroma from coffee as 3-hydroxy-3-penten-Z-one. Oil of Eugenia pungens was examined by Carro de la Torre A volatile oil of coriander, obtained by extraction with dilute and Retamar (100,102) who determined its main components alcohol followed by distillation, was investigated by Taskinen and the best time for harvesting the plant material. and Nykanen (562).Coriander oils resulting from extraction Oil of fennel can readily be distinguished from oil of anise with liquid COz were examined by Bykova et al. ( 8 4 ) ,particby the presence of fenchone using a method described by ularly with regard to linalool content. The composition of Thielemann (575).Brasil e Silva and Bauer (63)identified the coriander oil in relation to fruit ripeness was investigated by chief components of fennel oil. 88R
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The compositions of essential oils from flowers of Filipendula ulmaria, F. denudata, and F. stepposa were elucidated by Saifullina and Kozhina (497). Twenty-nine acids, most of which have not previously been reported to occur as free acids in oil of geranium, were identified by Ter Heide et al. (570). Nagahama e t al. (397) demonstrated the correct stereoisomeric configuration of a sesquiterpene from geranium oil, which has previously been believed to have another configuration. Ono and Tanaka (419) found an adulterant, 3,5,5-trimethylhexyl acetate, in a geranium oil imported from France. Kachakhidze (277) reported his findings from a gas chromatographic study of geranium oil. Mashanov and Mashanova (370) identified many components of a concrete obtained from Geranium macrorrhizum grown in the Crimea. Gurinovich and Kustova (232) examined oils from various regions of the USSR, and devised an analytical system for grading them. Carro de la Torre and Retamar (99) isolated the main components from the oil of a type of geranium, Pelargonium hortorum. Two new sesquiterpene alcohols from oil of ginger were isolated, and their structures were established by Bednarczyk et al. (41,42).They also evaluated the flavor impact of components of ginger oil and found that a-terpineol, citral a, psesquiphellandrene, ar-curcumene, nerolidol, and an unidentified sesquiterpene alcohol accounted for 85% of the flavor response. Mitra (385) identified the major components in oil of ginger from India, and Annathakrishna and Govindarajan (23) developed a colorimetric method for assaying the pungent principle in inger. The method eliminates nonpungent materials that eretofore had been included. Three new sesquiterpenes were isolated from ginseng oil and their stereochemistry was established by Yoshihara and Hirose (622). Fourteen sesquiterpene hydrocarbons were identified in the aroma of grapes by Schreier et al. (502). The chemical composition of oil of Helichrysum stoechas was elucidated by Proenca d a Cunha and Cardoso do Vale (460). Essential oils from the fruits, leaves, and other plant parts of Heracleum trachyloma were investigated by Koshin and Nguen (321). Many chemical substances were identified. From the oil of Heteropyxis natalensis, Gouveia et al. (221) identified many components, including butyl phthalate. Hiba wood oil yielded a new sesquiterpene hydrocarbon, as related by Ito et al. (269). Joulain and Ragault (276) discovered some new constituents in oil of hyssop. Khodzhimatov and Ramazanova (311) investigated the yield and composition of oils from different types of hyssop a t various stages of development. The composition of oil of Hyssopus zeravshanicus was extensively eluciated by Zotov et al. (630). The proportionate quantities of cis-3-hexenyl acetate, methylheptenone, and cis- and trans-linalool oxide in jasmine extracts of Algerian, French, Egyptian, and Italian orgin were determined by Lemberg (348). Various types of juniper oil were analyzed by Picci et al. (446). Three other varieties were analyzed by Von Rudloff (607),and the main components were identified. Hoerster et al. (252,253) identified many components of juniper leaf and berry oils from Romania. The essential oils from the leaves of different species of labdanum were compared as to chemical compostion by Guelz
i
(223,224).
Laggerol, as well as many other substances, was isolated from Laggera aurita oil by Zutshi et al. (632). The principal components of Lantana balansae oil were ascertained by De Viana (142),and Saleh (498) determined the composition of oils of several varieties of L. camara. The composition of larch essential oil was elucidated by Latysh et al. (337), and by Kolesnikova et al. (316, 317). Deryuzhkin et al. (141) determined many components in larch oil including 45% A3-carene, and Khan (310) separated 48 substances in the oil. Kepner et al. (308) found umbellulone, 1,8-cineole, and many other components in oil of mountain laurel. Kustrak and Besic (334) investigated methods of analyzing oils of lavender, lavandin, and spike lavender. They concluded that gas chromatography was best, and was the only method by which adulterated oils could be distinguished. Carro de la Torre (98) reported an investigation of lavender oil. Nicolov
et al. (409) analyzed oils of Bulgarian origin. Boyadzhieva and Staikov (62) concluded, on the basis of chemical composition, that oils of Bulgarian and Russian origin were superior to French oils. Belafi-Rethy et al. (46, 47) identified many components of Hungarian lavender oil. Timmer et al. (582) separated the lactones in lavender oil, and identified eight which had not previously been reported. Peyron (442) studied the variation in Lavendula leaf oils of cineole, camphor, and borneol content. Many components of the oils of Ledum palustre and L. groenlandicum were reported for the first time by Lawrence et al. (344). A monogram for lemon oil for the European Pharmacopeia was proposed by Imbesi (267). Ubertis and Carretto (589) applied UV and IR analysis to lemon oil, and Di Giacomo (149) discussed the composition and standards of Italian oil. Employing spectrofluometry and thin-layer chromatography, DiGiacomo et al. (154, 155),also investigated the composition of lemon oils from Sicily and Tucuman province in Argentina. Oils from Tucuman were also analyzed by Ayala (27), and Calvarano and Gallino (91) examined oil from the Brazilian “Gallego” lemon. The carbonyl compounds in lemon oil were colorimetrically determined by Sardi (501). Ciraolo and Calapaj (116) used ultraviolet to detect the presence of ethyl p-dimethylaminobenzoate in lemon oil. Carmona et al. (96) employed IR spectroscopy for the analysis of lemon oil. Fincke and Maurer (182) studied the chemical changes, including oxidation, of lemon oil in storage and in candies. Palma et al. (426, 427) explored the variables in the hydroxylamine determination of citral, and Retamar et al. (469) employed IR to determine citral and esters in lemon oil. Egyptian lemongrass oil was analyzed using thin-layer chromatography by Zaki et al. (624),by Foda et al. (183) using IR spectroscopy, and by Abd Allah ( 1 ) employing gas chro-, matography. Brazilian lemongrass oil was described by Gonzalo de Vendetti and Villarrubia d e Martinez (216,217). Oil from the roots of Malabar lemongrass was analyzed by Yeh (619).
The main component of Lentinus edodes oil, according to Kameoka and Higuchi (282),was 1-octen-3-01. The main components in oil of Lepechinia graveolens were identified by De Riscala and Retamar (139). Many constituents of the flower oils from lily of the valley and lilac were reported by Mack et al. (360). Ata (26) found that naturally occurring citric acid in lime mash caused detrimental changes in lime oil during distillation, and oil of better quality could be obtained if contact with the acid was avoided during distillation. Tapanes and Perez Zayas (559) identified the carbonyl compounds in lime oil from Cuba. Formaldehyde, acetaldehyde, methylheptenone, and others were reported for the first time. They (438) also compared the terpene and sesquiterpene portions of lime oils obtained by centrifugation and distillation. Oils of Limnophila rugosa, distilled a t various stages of plant maturity, were analyzed by Agarwal et al. (10). The composition remained similar a t all stages. Among many other components of Indian linaloe husk oil, Adams and Bhatnagar (6) identified two new esters, cis- and trans- 2,6,6-trimethyl-2-vinyl-5-acetoxy-tetrahydropyran, which had a pleasant citrus odor. Rodes et al. (479) studied the chemical changes during steam distillation of the oil. The yield and composition of oils of Lippia adoensis and L. schiniperi were investigated by Rovesti (486).Delfini and Retamar (134) identified many components of L. fissicalyx oil, and Retamar et al. (472 ) published further findings. Sixteen components were found in oil of lovage root by Ribori et al. (580),who found two additional constituents, caryophyllene and nerolidol, in lovage leaf oil. The volatile components of roasted macadamia nuts were shown by Crain and Tang (124) to be similar to those of other roasted nuts. One difference noted was the presence of dimethyl sulfide in the headspace. Among the volatile components of canned Alphonso mango, Hunter et al. (264) found 2,5-dimethyl-4-methoxy-2Hfuran-3-one, which had not previously been reported in nature. Fujita et al. (201-203) examined the composition of many Magnolia hobus oils obtained from plants of various origin. Fujita and Fujita (195) similarly studied the components of M. salicifolia oils. ANALYTICAL CHEMISTRY, VOL. 49, NO. 5, APRIL 1977
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Oil of sweet marjoram was shown by Taskinen (560) to contain 53 identifiable components, 35 of which were reported for the first time. Granger et al. (222) characterized marjoram oils by the preponderance of certain components, including cis- and trans-4-thujanol. Mody et al. (388, 389) studied the composition of oil of marsh grass. Among many components identified was p tolualdehyde. The main constituents of oil of mastic were identified by Calabro and Curro (85,87), and also by Scrubis et al. (506). The composition of oil of Mentha aquatica was elucidated by Malingre and Maarse (364).Piper and Price (449)showed that M. aruensis grown from seed and selected a t random could produce highly abnormal oils. Donalisio et al. (161) also reported an abnormal oil from a new cultivar of M . aruensis. Murray (395) described oils from new hybrids of M. citrata. Essential oil of M. gentilis, a wild mint from the Takai district, was extensively investigated by Nagasawa et al. (400-4021, who, for the first time, isolated and established the stereochemistry of several components. M. longifolia essential oils were investigated both by Bui Thi Bang and Nikolaev (77)and Calvarano and Codignola (90). Hefendehl and Nagell (242) noted the difference among oils from M. rotundifolia, M . longifolia, and a hybrid. Nagell et al. (403) isolated two stereoisomeric 1,2-epoxymenthyl acetates from the hybrid oil. Chobanu and Nikolaev (110) reported the composition of an oil from Caucasian mint, and Kovineva et al. (319) described the high oil and menthol content obtained from a new mint hybrid. Shimizu et al. (520)analyzed the oils of various mints growing wild in Japan. Cantoria (94) evaluated the oil from a mint grown in the Philippines whose main component was carvone. Bui Thi Bang and Nikolaev (78) analyzed several Mentha oils from plants grown in the Kishinev region and whose main component was linalool. The oils from shoots, branchlets, and the trunk of Metasequoia glyptostroboides were analyzed by Fujita et al. (199).
The composition of Minthostachys uerticillata oil was determined by Lizzi and Retamar (353).Carvone and pulegone were the main components. Gupta and Chandra (228) ascertained the major constituents of Murraya exotica oil. The significance of volatile constituents in cultivated mushrooms in respect to their flavor was studied by Dijkstra and Wiken (158). (-)-l-Octen-3-01 was the most important aroma component. Pyysalo (463) identified about 50 volatile compounds in each of seven edible mushrooms. Wasowicz and Kaminski (609) found that six alcohols were the main components among the aroma compounds of mushrooms. Fifty-one and 21 compounds were identified in the oils of Myrcia gale and M. comptonia peregrina, respectively, by Lawrence and Weaver (345).Tattje and Bos (565) found 31 components in M . gale oil, some for the first time. The oil of Myrothammus flabellifolius was analyzed by Proenca da Cunha and Roque (456,461),who identified many components including perillyl alcohol. The main components of Portugese myrtle oil were reported by Frazao et al. (191). In the absolute of Narcissus tazetta, Shikhiev and Serkerov (519) identified nonadecyl alcohol and p-sitosterol. Norseychelanone and patchouli alcohol, among other substances, were isolated from oil of Nardostachys jatamansi and identified by Ruecker et al. (492). A new sesquiterpene alcohol, nepetol, was isolated from oil of Nepeta leucophylla by Gupta (229),together with many other components. Gatanova and Maksanova (212) presented a preliminary physicochemical study of N . madrantha oil. Corbier and Teisseire (121) identified cis-8-heptadecence in neroli oil. and 2,5-dimethyl-2-vinyl-4-hexenal Thymohydroquinone was isolated by El-Alfy et al. (170) from Nigella sativa seed oil. The chemical composition of East Indian and West Indian nutmeg oils were compared by Baldry et al. (30),who reported finding six compounds not previously identified in nutmeg oils. Matthews et al. (377) described a similar study of Grenada nutmeg oil. A new nutmeg oil from New Guinea was investigated by Piper and Price (448). The oil contained less than 0.5% of phenols. From an essential oil of oak moss, Corbier and Teisseire (122) isolated l,cis-8-heptadecadiene, l,cis-8,cis-11-hepta88R
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decatriene, and 4,6-dimethyl-4-decene-3-one. Pekhov et al. (437) examined an essential oil of Ocimum gratissimum obtained with liquid COZ extraction and found it to be considerably different from steam distilled oil. Morhy (392) reported methylchavicol and anethole to be among the main components of 0. selloi oil. Rovesti (488,489)described oil of 0. suaue from East Africa. Many components, including three polyacetylenic hydrocarbons were detected by Vincieri et al. (599) in oil of Oenanthe aquatica. Two essential oils of olibanum were analyzed by Higazy et al. (247,248). To obtain one of the oils, extraction with benzene was employed, for the other ethyl alcohol was used. The quantitative composition of onion oil was correlated with its flavor by Galetto and Bednarczyk (204). Galetto and Hoffman (205) synthesized and evaluated the flavor contribution of 2,5- and 3,4-dimethylthiophene and found that, contrary to what has been reported before, these substances did not contribute significantly to onion flavor. A volatile fraction of Valencia orange oil, which was important to its flavor, was shown by Shaw and Coleman (516) to contain two new components, isoprene and 3-methyl-1butene. Shaw and Moshonas (517) developed a rapid method for monitoring orange essence, compiled a list of the components, and identified 30, two for the first time. Calderon Gomez (88) examined sweet and bitter orange oils steamdistilled from the peels of Columbian fruit. Di Giacomo (150) reviewed the properties of sweet orange oils and listed all known components. Jorro et al. (273) studied the seasonal changes in the essential oils from Comuna oranges grown in Valencia. Millet et al. (382)found that orange oil obtained by vacuum distillation and trapping at -80 “C had a far lesser number of constituents and a lower ester and aldehyde content than oils obtained by conventional means. Coleman and Shaw (118) suggested that distilled orange oil could serve as a source of liniiool. Lamonica et al. (336) identified manv fattv acids in bitter orange oil. Di Giacomo and Postorino (156)c6mpared the UV spectrophotometric analysis of bitter orange oils obtained by the usual line-treatment process and by the “shading” process. Shiga (518) characterized spatchuleol in bitter orange oil. An unusual compound, 4,5-epoxy-p-ment-l-ene, was isolated by Lawrence et al. (343) from Origanum heracleoticum oil. Maarse and Van Os (357, 358) found 49 components in origanum oil, and in oil from the leaves 39 components were noted. Oils from various plant parts of the orpine were obtained and examined by Mesicek and Perpar (380). Many organoleptically potent components of Paederia chinensis oil were identified by Kurihara et al. (332). Kubeczka and Stahl(324) identified the major constituents of Pastinaca sativa root oil. Nakahara et al. (404) characterized two new components of Indonesian patchouli oil. Dhekne and Paknikar (146) demonstrated that “hydrocarbon E”, previously believed to be a tricyclic sesquiterpene, is actually tetracyclic and identical to cycloseychellene. A number of lactones were identified by Molina et al. (390) among the volatile components of peach. Several pennyroyal oils from parts of Istanbul were analyzed by Alpmen (18). Frazao et al. (190) investigated the possibility of different chemical types of pennyroyal in Portugal. Sarawak and Lampong black pepper volatile oils could be distinguished by the method of Russell and Else (495). Debrauwere and Verzele (129-131) identified 26 hydrocarbons in black pepper oil, three of which had not previously been mentioned, as well as 51 oxygenated constituents, of which only six had previously been reported and many had not been previously found in nature. Peppermint oils from the United States, England, Eastern Europe, and Morocco were distinguished by Hefendehl and Ziegler (243) from Mentha aruensis oils on the basis of their chemical composition. Baslas et al. (38) investigated the composition of peppermint oil from India. Yankulov et al. (618) studied the yield and quality of peppermint oils from several experimental plantings and found one to be superior. Hoelzl et al. (251) examined the oils from other experimental plantings; Upadhyay et al. (590) reported on oils from trial plantings in India; and Kartnig and Still (301) identified the
components of peppermint oils from Burgstall-Wies agricultural test plantings. Stanev (540) described changes in peppermint oil caused by mutations, Cardoso do Vale and Proenca da Cunha (95) studied the oil obtained from a plantation attacked by a parasite, and Duhan et al. (165)reported the effect of plant age on peppermint oil. Ono and Tanaka (418) developed a thin-layer chromatography method for simultaneously determining menthofuran and cineol in peppermint oils. Senich et al. (509,510) found that oil obtained by COz extraction had a higher menthol and lower menthone content, and also determined the composition of a COz extract from peppermint leaf waste. Lawrence (338)found 18hitherto unreported trace constituents in peppermint oil. The composition of the essential oils of a number of Pelargonium species of perfume interest was elucidated by Lawrence et al. (341). The leaf oil of Persea americana was shown by Acosta de Iglesias (5) to be composed almost exclusively of estragole and anethole. The chemical composition of Paraguayan petitgrain oil was compared by Urbieta-Rehnfeld and Jennings (591) with that of French oil. Di Giacomo and Romeo (157) performed an analysis on oil of Italian petitgrains, using IR spectroscopy. Bruns and Koehler (76) identified 38 components of Peumus boldus leaf oil. The essential oil composition of various Bulgarian pines and other conifers was reported by Nikolov et al. (411).The volatile oil constituents from the bark of the lodgepole pine were compared by Shrimpton (522) with those of the leaf and wood oil. Snajberk and Zavarin (534) identified many components of the turpentine oil from Pinus edulis. Akimov and Kuznetsov (11)compared the oils of P. hamata, P. pallasiana, and P. siluestris. Tyukavkina et al. (587) identified many phenolic acids and related substances among the volatile compounds in P. syluestris, P. sibirica, and P. abies nephrolepis. Sylvestrene and other monoterpenes were identified in the turpentine oil from P. sylvestris by Bardyshev et al. (35). The terpenoids from P. taiwanensis were quantitatively determined by Lu et al. (356). The composition of essential oil of Pluchea sagittalis was investigated by Talenti et al. (555-557). Caryophyllene and humulene were found along with many other components. The volatile oils of flowers of Plumeria rubra and P. rubra alba were analyzed by Mahran et al. (362). Nursten and Sheen (413)identified 35 volatile components of potato, including 2-methoxy-3-ethylpyrazinewhich had a distinct raw potato odor. Some components of Primula elatior oil were identified by Goris and Frigot (218). The quantitative chemical composition of Provencal vervain oil was determined by Buil et al. (79). Forrey and Flath (184) identified 53 components of Prunus salicina, including ethyl anisate and y-lactones. The essential oil components of three Pseudocaryophyllus species were ascertained by Correa et al. (123),and De Fenik et al. (132) determined the composition of Pseudocaryophyllus quili. Some major components of the oil of pseudosorghum grass were identified by Joshi et al. (275). The main constituents in oils of Rhododendron kotschyi leaves and fruit were identified by Tamas and Ciupe (558). One hundred components were separated from the oil of Chinese rhubarb rhizomes, and 43 were identified by Frattini et al. (186,187). Oils from different types of rhubarb showed quantitative differences. Diisobutyl phthalate and chrysophanic acid were the most important components. The essential oil and concrete of Turkish rose were described by Garner0 et al. (211).Balinova-Tsvetkova et al. (32) developed a gas chromatography method for analyzing the rose oil composition in a single flower. Kapetanovic (290-292) examined the oil content and quality of Rosa damascena from Bosnia and Hercegovina and of R. alba, and designed a method for recirculating the distillation water and improving the yield of oil. The composition of Bulgarian rose absolute and the structure of many of its components were ascertained by Stoyanova-Ivanova et al. (543,544).Similarities as well as differences in the oil composition of various rose species were noted by Herout et al. (246).Streibl et al. (545) differentiated the compositions of essential oils from the glandular leaves of various rose species. Nicolov et al. (410) quantitatively
analyzed the absolute of Bulgarian rose. Ehret and Teisseire (167) isolated and identified nerol oxide from Bulgarian rose oil. Staikov et al. (538, 539) investigated the influence of storage conditions of rose petals on the quality of the oil, and also experimented to find the best time for harvesting rose flowers. Balinova-Tsvetkova and Dyakov (31) described an improved small-volume apparatus for assaying oil quality in flowers. Aliev et al. (13) obtained a normal rose oil by extraction with an NR-3 solvent, and Kuseva-Mladenova et al. (333) produced a rose oil from rose seeds. The oil was very similar to that obtained from petals. Portugese rosemary oil was compared with oils from other countries by Frazao and Da Cunha (188). Damjanic and Grzunov (126) analyzed three rosemary oils produced by different laboratory methods. The compositional variations in rue oils from various plant parts and distilled a t various seasons were explored by Andon and Belova (20). Kubeczka (323) characterized the main component of the essential oil from rue roots, pregeijeren. Srepel and Supancic (536) developed a thin-layer chromatographic separation of the methyl ketone in rue oil, and Tattje et al. (566) isolated and identified a number of constituents not previously reported in oil of rue. High levels of linalyl acetate and linalool were demonstrated in sage clary oils of Bulgarian origin by Ilieva et al. (266),who also identified eight other constituents. Leffingwell et al. (347) found a number of constituents, including P-caryophyllene epoxide for the first time in clary sage oil. Karetnikova et al. (298) reported some main components of a cohobated oil. Popa and Salei (452) described procedures for isolating manool from sage clary, and Corbier and Teisseire (120) characterized germacrene D and isolated numerous other components of sage clary oil. The composition of Saluia dorisiana oil was determined by Halim and Collins (237). Karryev (300) identified the major constituents of oils of Saluia seravschanica and Perouskia scrophulariaefolia. The properties and chemicai composition of sandalwood oil were discussed by Kar (293).Demole et al. (137) isolated, identified, and established the structure of 32 components of sandalwood oil which had not previously been reported. Four of these were novel natural substances. Adams et al. (8) identified many sesquiterpene components of Australian sandalwood oils. Among 30 components of Sancloricum koetjape, Oliveres-Belardo and Hickman (415) reported allo-aromadendrene. Miles et a1 (381) identified p-tolualdehyde among many other components of Sarracenia flaua oil. Menthol and isomers thereof were the major components of Saturega calamintha according to Frazao et al. (192).The composition of S. douglasii oil was ascertained by Lawrence et al. (339). Essential oil of Saururus cernuus, which was rich in sesquiterpenes, was analyzed by Tutupalli et al. (586). Oil of savory from Albania was investigated by Asllani (25), and the composition of a type of savory oil from Tucuman province was determined by Tomasini and Retamar (584). Kameoka et al. (286) identified 48 components of saxifraga stolonifera oil. Many constituents of green and ripe California Schinus molle oils were isolated by Jennings and Bernhard (272). Fujita and Fujita (196) distilled oil of Schizonepeta tenuifolia and determined its chemical composition. Some main components of oil of Schraderia dracocephaloides were listed by Kerimov et al. (309). Among the aroma chemicals of roasted sesame seeds, Soliman et al. (535) identified 2-pentylfuraq guaiacol, pyrazines, and others. Dembele and Dubois (135) investigated oil of shallots and pointed out its differences from onion oil. Employing thin-layer chromatography, Pathak and Pant (434) distinguished many components of Skimmia laureola oil. Solidage altisima oil from the stems and leaves of a type of goldenrod was investigated by Suemitsu et al. (549) and by Nii et al. (408). Its quantitative and qualitative composition was obtained. Olszewski and Pluta (416,417) reported 20% carvone, and other components in Polish spearmint oil, and studied its ANALYTICAL CHEMISTRY, VOL. 49, NO. 5, APRIL 1977
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variation with plant naturity. Canova (93) identified 94 components in a Scotch spearmint oil and proposed the compounding of a synthetic oil. Nagasawa et al. (399) identified the component responsible for the peculiar odor of a Japanese spearmint oil as cis- carveyl acetate. Hrutfiord et al. (259)found great variations in the composition of Sitka spruce oil from needles and cortex, depending on the season. For example, the myrcene content of needle oil varied from 95 to 40%. The major components of Stenocalyx micheli, a type of myrtle, oil were identified by Lalli de Viana and Retamar (335).
Yamashita et al. (617) observed the formation of volatile esters in the living strawberry from alcohols and acids. Seventy different esters were formed. In a study of the oil from the flowering tops of Tagetes erecta, Gupta and Bhandari (230,231) identified, among other substances, tagetone and nonanal. T. patual leaf oil contained ocimene, linalool, methyl heptenol, linalyl acetate, and tagetone. Carro de la Torre and Retamar (101) identified many components of oil of T . minuta from the Tucuman province. The most frequently encountered types of tansy oil obtained from genetic variations growing in Hungary were those containing artemisia ketone and umbellulone, according to a study by Tetenyi et al. (574).Bankowski and Chabudzinski (33) reported variations in tansy oil composition depending on soil conditions. Numerous components of black tea aroma were identified by Cazenave et al. (105,106). Some of the components were associated with its fruity or flowery character. Renold et al. (468) reported many newly discovered components including @-Fyclocitral,safranal, and a unique homosesquiterpene; and Vitzthum et al. (604) identified 56 constituents, mainly pyridines, pyrazines, quinolines, thiazoles, amines, and carbonyls for the first time in black tea aroma. The head space vapors of four kinds of green tea were analyzed by Kawabata and Ohtsuki (303). Yamanishi et al. (616) compared the aroma composition of two types of green tea. Hara and Kubota (238, 239) observed the changes in the volatile components of green tea during roasting, and identified many carbonyl compounds by thin-layer chromatography. Valeeva (594) found that the oil of Tetrataenium olgae fruits consisted primarily of complex esters of borneol. Some components of Teucrium polium oil were identified by Wassel and Ahmed (610). Thin-layer chromatography and IR spectroscopy were used by Popescu (453)to determine the main components of thyme oil produced in Romania. Thymol, carvacrol, and other components of Bulgarian thyme oil were identified by Stanev (541). Karawya and Hifnawy (297) found that Egyptian thyme oil was richer in linalool and terpenes and had less thymol and carvacrol than oils from other countries. Miquel et al. (383) showed that Moroccan thyme oil is very different and has a characteristic gas chromatographic pattern. Richard et al. (473) illustrated that Moroccan thyme oil could be distinguished from the one from Provence by its much higher borneol content. Many constituents of Thymus chamaedris oil were isolated by Seoane et al. (511).De Gavina et al. (133) showed the essential oil of T. gadorensis to be rich in carvacrol and thymol. The main components of coin thyme oil from Azerbaidjan CCR were identified by Kasumov and Ismailov (302),and Frazao and Domingues (189) identified those of 3". mastichina oil. The oil of wild thyme T. serphyllus from Kashmir, was investigated by Razdan and Koul (467), who identified its main components. Similarly, Sinha et al. (530) analyzed wild thyme oil from India, and Vidojkovic (597,598) studied wild thyme oil from eastern Serbia. In a study of the essence and essential oil components of flue-cured tobacco, Lloyd et al. (354) identified a total of 323 compounds, of which 275 had not previously been reported in flue-cured tobacco, and 132 had not previously been noted in any tobacco. Devreux et al. (143-145) separated the carbonyl, hydrocarbon, and phenol fractions of the essential oil of tobacco, and identified many components in each. Richter (474,475) analyzed the acid and phenolic fractions of Virginia tobacco oil and filler tobacco oil, identified many components, and noted certain compositional differences. Chuman and Noguchi (113) isolated a new terpenoid acid from Turkish tobacco, and Einolf (168) described the isolation, identifica90R
ANALYTICAL CHEMISTRY, VOL. 49, NO. 5, APRIL 1977
tion, and structure determination of the Oriental tobacco flavor component, dihydroactinidiolide. Schumacher and Vestal (503) identified many volatile constituents of Turkish tobacco, including 25 not previously reported in tobacco, and drew conclusions as to which components are primarily responsible for Turkish tobacco flavor. El-Gindy and Lofty (173) investigated the effect of production methods and antioxidants on the stability of tuberose essential oils. Nayak (407) determined some major components of Indian turpentine oil. The oil is low in pinene content. Twenty-two volatile compounds in Madagascar, Mexican, and Tahitian vanilla beans were identified by Shiota and Itoga (521).Fifteen of the compounds, including vanillyl ethyl ether and anisyl ethyl ether, were reported for the first time in vanilla. @-Iononeand patchouli alcohol were identified by Ruecker and Tautges (491) in oil of valerian roots. A number of esters and other components were identified in valerian root oil by Pethes et al. (440).The sesquiterpinoids in Japanese valerian oil were scrutinized by Hikino et al. (249),who found compounds having the valerane and kessane skeletons and pointed out that kessyl glycol was not present. Zalkow and Clower (625) isolated acoradiene from vetiver oil and established its absolute configuration. Peyron et al. (443) identified hexylene glycol as an adulterant in certain vetiver oils. Kurihara and Kikuchi (331) distilled an oil from the flowers of Viburnum dilatum and identified many of its components. Numerous volatile flavor components from watermelon were identified by Kemp et al. (306,307). Of especial note was the characterization of cis,cis-3,6-nonadien-l-ol. The essential oil of wistaria flowers was analyzed by Kurihara and Kikuchi (330),who identified many of its constituents. A type of wormseed oil from Brazil was investigated by Bauer and Brasil e Silva (401, and Gigienova et al. (214) demonstrated the presence of a-hydroxydienic acids in wormseed oil from Middle Asia. Descending paper chromatography and gas chromatography was used by Dudko et al. (163, 164) to determine the main constituents of wormwood oils from the Garnyi Altai region and Siberia. Their phenol content was studied by Usynina et al. (593).Wormwood oils from various parts of the plant were compared by Slepetys (532).
Azulene and @-pinenewere preponderant among the main components of oil of yarrow determined by Haggag et al. (236). Chelishvili and Tavberidze (109) found another yarrow oil to have a similar composition. Falk et al. (179) identified 24 compounds and isolated five from oil of yarrow flowers. The acid fraction of ylang-ylang oil was demonstrated by Timmer et al. (581j to contain eight previously unreported acids, one of which, (E)-geranic acid, has seldom been reported as a constituent of essential oils. The major components of oils from various plant parts of Zanthoxylum decaryi were ascertained by Perr et al. (439). Goutam and Purohit (220) identified the main components of 2 . oualifolium seed oil, and Mathai (372) examined 2. rhesta oil. The structure and configuration of several sesquiterpenoids from oil of zeodary were elucidated by Hikino et al. (250). Aromatic Chemicals-General. A comprehensive discussion of monoterpenoids was published by Thomas (576). Von Rudloff (606) described methods employed in the gas chromatography of terpenes. Bedoukian (43, 44) reviewed progress in perfumery materials and discussed the increasing importance of acetylenic compounds. A number of interesting new components of common essential oils were pointed out by Terhune et al. (572), and Yoshihara (623) classified aromatic chemicals with a green odor into 14 odor groups. Acids. Argemonic acid, a new unusual long chain fatty acid was isolated from argemone oil by Rukmini (494). a-Keto acids were determined in rye and wheat products with thin-layer chromatography, after conversion to quinoxalones, by Beletskaya et al. (48). Aldehydes and Ketones. Sliwiok and Ogierman (533) separated alkyl aromatic ketones by thin-layer chromatography and listed their R values. Ohkura and Zaitsu (414) developed a fluorometric determination of aromatic aldehydes
terpineols. Alpande de Morais et al. (17 ) assayed the thymol content of oils obtained from amazonian plants. Esters and Lactones. Pickett et al. (447) demonstrated that some esters are destroyed during the steam distillation of essential oils. New sesquiterpene lactones from Athanasia species were isolated and structurally elucidated by Bohlmann and Grenz
with 1,2-diaminonaphthalene. Iwamura et al. (270) noted the mass spectra of some aldehydes and ketones, and Wheeler and Shonowo (611) described the mass spectra of some bicyclic ketones having a cyclopropane ring, such as umbellulone. Menaria (378) proposed 2-diphenylacetyl-1,3-indanedione1-hydrazone as an agent for making derivatives. Rothbaecher and Suteu (482) related the conformation of monoterpene ketones to their behavior in chromatography. A new mechanism was proposed by Korvola and Malkonen (318) for the fragmentation of camphor, based on a study of its mass spectrum. Carvone was assayed with a UV absorption method by Roethbaecher et al. (481). A high-speed liquid chromatography procedure was applied to the analysis of citral by Rabinowitz et al. (464).Karawya et al. (294) employed a colorimetric assay for citral. Impurities in commercial cyclamen aldehyde were identified by Shutikova et al. (524). The structure of germacrone, isolated from oil of Pogostemon fomosanus, was established by Yeh (621). (-)-(lR)-S-hydroxy-4-p -menthen-3-one was identified in oil of Mentha gentilis by Nagasawa et al. (398). Manville (368) demonstrated that juvabione and its analogues, isolated from Abies balsamea have the R,R stereoconfiguration and not the R,S. A specific color reaction of a-keto aldehydes was used by Rioux-Lacoste and Vie1 (477) for their characterization and determination. The generation of aldehydes from sugars and amino acids in meats was studied by Hongo et al. (256,257). Harkes and Begemann (240) identified many aldehydes found in cooked chicken. A chemically pure menthone was prepared by Baslas (39) with chromatographic methods. Abe and Musha ( 2 ) reported a gas chromatographic resolution of (f)-menthone through its (+)-tartaric acid derivative. The percentage content of muscone was used by Hsu et al. (261) for evaluation of the quality of musk samples and musk preparations. Nona-2,4,6-trienal, an unusual compound to exist in nature, was found by Buttery (81) in the essential oil from dry red beans. Parameters for the quantitative determination of thujone by oxime formation were optimized by Shaftan and Naboka (512). Synthetic vanillin was detected by isotopic analysis in vanilla extracts by Bricout et al. (69).Traces of vanillin in butterfat were determined with various techniques by Guyot
Bohlmann et al. (59) also identified a thiophene ester from oil of Anthemis austriaca roots. An improved method for bergaptene determination by high performance liquid chromatography, which achieved a sensitivity of better than 0.5 ppm, was described by Shu et al. (523).Wisneski (615) used thin-layer chromatography and spectrophotofluorometry, and Gautschi (213) discussed spectrometric, thin-layer, gas, and liquid chromatography for the determination of bergaptene in perfumes. Coumarin was detected in vanilla flavored foods b thinlayer chromatography conducted by Sengupta et al. 6 0 8 ) . The structure of crotofolin A, a new diterpene with a new skeleton, was determined by x-ray crystallography by Chan et al. (107). The stereochemistry of deacetylinulicin, a new sesquiterpene lactone isolated from Inula japonica was established by Evstratova et al. (178). Strawberry “aldehyde C-16” and related glycidic acid esters were identified in flavored foods with methods refined by Braun and Hieke (64). On the basis of experimental trials of the AOAC method for determining methvl salicvlate, some changes in the urocedure were reco6mended by Markus (369). The structures of three new sesquiterpene lactones from Osmitopsis asteriscoides were deducted by Bohlmann and Zdero ( 5 6 ) . Rivett (478),and also Moran et al. (391) reported isolating and identifying S-prenyl thioisobutyrate in Agathosma oils. Ethers, Oxides, and Peroxides. Churacek (114) discussed the separation of ethers and peroxides by liquid column chromatography. Rovesti (487) reported that deep-freezing citrus oils a t -40 “C markedly inhibited the normal increase in peroxide index. A number of new furansesquiterpenes were isolated from various essential oils by Bohlmann and Zdero (55),who determined their structures. 1-(3,4-Dirnethoxyphenyl)butadiene was identified as a constituent of Zingiber cassumunar by Baker and Nabney
(234).
(28).
Alcohols and Phenols. The hydroxyl values of alcohols and phenols were determined by Kumar and Kartha (328)through back-titration of a xylene-acetic anhydride reaction. Churacek and Coupek (115) described the separation of phenols by gel, adsorption, and ion-exchange chromatography. The mass spectra of 65 monoterpene alcohols were studied by Iwamura et al. (271),and certain characteristic ions were listed. The sodium complex method was used by Siddiqui et al. (525) to isolate citronellol from oil of citronella Java. A standardized gas chromatography method for assayin eugenol in oil of bay was proposed in the Analyst (London? (19).
Gymnomitrol and related sesquiterpenoids were proven by Connolly et al. (119) to have a novel tricyclic absolute configuration. Karawya et al. (295) proposed a thin-layer chromatography colorimetric method for the assay of linalool in essential oils. De Araujo et al. (128) determined linalool in a number of Amazonian essential oils which were rich in this component. Maltol and ethylmaltol were detected in foods by Zappavigna et al. (626). Ethylmaltol was not found in any natural material. m-Menth-1-en-8-01was confirmed by Abraham and Verghese ( 3 )as a constituent of Wallach’s sylveterpineol on the basis of NMR spectra. The structure and absolute configuration of norpatchoulenol was established by Teisseire et al. (568). The products of the air oxidation of a-terpineol were identified by Tsai and Cheng (585),and Bakhtinov et al. (29) elucidated the isomers and impurities present in commercial
(54).
Terpenes and Hydrocarbons. New sesquiterpene analogues of common monoterpenes, including sesquithujene, sesquisabinene, and others, were isolated from essential oils by Terhune et al. (571), and their structures were determined. Two new sesquiterpene hydrocarbons, bicyclosesquiphellandrene and 1-epibicyclosesquiphellandrenewere isolated by Terhune et al. (573).Their structures were elucidated by spectroscopic studies, and their stereochemistry by acid rearrangement and hydrogenation experiments. Saraswathi et al. (500) showed that Baeyer’s carvestrene is a mixture of at least eight hydrocarbons. Joshi et al. (274) isolated and elucidated the stereochemistry of clausantalene, a new sesquiterpene from Clausena indica. Tricyclic sesquiterpenes were isolated from Eremophila georgei by Carrol et al. (104).Their absolute stereochemistry was antipodal to that of the zizaene sesquiterpenes of vetiver oil. New furanoeremophilanes, sesquiterpenes isolated from Mexican Senecio species, were structurally elucidated by Bohlmann and Zdero (57,58).Other naturally occurring terpene derivatives, constituents of the genus Brickellia, were also isolated and their structures were determined on the basis of NMR and mass spectra. Seychellene and seychellane were isolated from Narkostachys jatamansi and identified by Maheshwari and Saxena (361).
Miscellaneous. A caffeine determination in soft drinks was accomplished by Ruick and Schmidt (493) using UV photometry at 273 nm. ANALYTICAL CHEMISTRY, VOL. 49,
NO. 5, APRIL 1977
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Capsaicin was determined in paprika by extraction and thin-layer chromatography by Andre and Mile (21 ). Two indole compounds were isolated and identified by Bercht et al. (50) from cannabis grown in the Netherlands. Paul et al. (435,436)developed a titrimetric determination of mercaptans with potassium hexacyanoferrate, as well as another method using halogen cyanides at elevated temperatures. The odor intensities of six commercial musks were compared by D'Andrea (125) by the method of equal odor intensity.
Nitrogen determinations employing two new digestion procedures, much faster than the usual Kjeldahl method, were developed by Von Lengerken et al. (605). Several pyrazines, volatile components of bread flavor, were identified by Sizer et al. (531). Many volatile components of hickory smoke flavor were identified by Hruza et al. (260). Shankaranarayana et al. (523)) and also Schutte (504)) discussed the sulfur-containing flavor components of foods, and Garbusov et al. (206) identified many sulfur compounds in boiled beef.
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(236) Haggag, M. Y., Shalaby, A. S., Verzar-Petri, G., Planta Med., 27(4), 361 (1975); Chem. Abstr., 83, 1367091 11975). (237f Halim: A. F., Collins, R. P., J. Agric. Food Chem., 23(3), 506 (1975). (238) Hara, T., Kubota, E., Nippon Shokuhin Kogyo Gakkai-Shi, 20(6), 283 (1973); Chem. Abstr., 84, 57532p (1976). (239) lbid., (7), p 31 1; Chem. Abstr., 84, 5 7 5 4 7 ~ (1976). (240) Harkes, P. D., Begemann, W. J., J. Am. Oil Chem. SOC., 51(8), 356 (1974). (241) Hayashi. N., Yokochyo, K., Komae, H., Z. Naturforsch., C: Biosci., 30C(5-6), 421 (1975): Chem. Abstr., 83, 1 5 4 8 4 ~(1975). (242) Hefendehl, F. W., Nagell, A,, Parfuem. Kosmet., 56(7), 189 (1975); Chem. Abstr., 83, 20913n (1975). (243) Hefendehl, F. W., Ziegler, E., Dtsch. Le6ensm.-Rundsch., 71(8), 287 (1975); Chem. Abstr., 83, 191475e (1975). (244) Hendriks, H., Malingre, T. M., Batterman, S., Bos, R., Phytochemistry, 14(3), 814 (1975). (245) Herisset, A,, Jolivet, J., Lavault, M., Plant. Med. Phytother., 8(3), 161 (1974); Chem. Abstr., 82, 64313e (1975). (246) Herout, V., Ubik, K., Streibel, M., h t . Congr. ESSent. Oils, (Pap.), 6th 1974, 116, 6 pp; Chem. Abstr., 84, 49731n (1976). (247) Higazy, S. A., Abdel Akher, M. A. O., ElWakeii, F. A., Loufty, M. K., Egypt. J. FocdSci., 1(2), 203 (1973); Chem. Abstr., 83, 1521721 (1975). (248) lbid., 2(1), 29 (1974); Chem. Abstr., 83, 653103 (1975). (249) Hikino, H., Kato, T., Takemoto, T., Yakugaku Zasshi, 95(2), 243 (1975); Chem. Abstr., 83, 104561 (1975). (250) Hikino, H., Konno, C., Agatsuma, K., Takemoto, T., Horibe, I., Tori, K., Ueyama, M., Takeda, K., J. Chem. SOC.,Perkin Trans. 1, 1975(5), 478. (251) Hoelzl, J., Fritz, D., Franz, Ch., Garte, L.. Deut. Apoth.-Ztg., 114(14), 513 (1974): Chem. Abstr., 81, 166312a (1974). (252) Hoerster. H., Csedo, C., Racz, G., Rev. Med. (Tirgu-Mures, Rom.), 20(1), 79 (1974); Chem. Abstr., 82, 21701n (1975). (253) lbid., (2), p 215; Chem. Abstr., 82, 167565t (1975). (254) Hogg, J. W., Terhune, S. J., Lawrence, B. M., Cosmet. Perfum., 89(9), 64, 66, 69 (1974). (255) Holden, C. M., Whittaker, D., Org. Magn. Reson., 7(3), 125 (1975). (256) Hongo, F., Kako, Y., Ryukyu Daigaku Nogakubu Gakujutsu Hokoku, 1973(20), 245; Chem. Abstr., 81, 134754e (1974). (257) Hongo, F., Kojima, M., ibid., p 229; Chem. Abstr., 81, 134753d (1974). (258) Honkanen, E., Kallio, H., Pyysalo, T., Kern.-Kemi, 3(4), 180 (1976); Chem. Abstr., 85, 5 9 5 5 1 (1976). ~ (259) Hrutfiord, B. F., Hopley. S. M., Gara, R. I., Phytochemistry, 13(10), 2167 (1974). (260) Hruza, D. E., Van Praag, M., Heinsohn, H., Chem. Technol., 4(8), 512 (1974). (261) Hsu, H.-Y., Wu, T.-M., Chen, Y.-P., T'ai-wan Yao Hsueh Tsa Chih, 25(1-2), 26 (1973): Chem. Abstr., 84, 95516u (1976). (262) Huergo, H. H., Retamat, J. A,, Arch. Bioquim., Quim. Farm., 18, 15 (1973): Chem. Abstr., 83, 1 2 0 6 3 5 ~(1975). (263) Huergo, H., Retamar, J. A,, lnt. Congr. Essent. Oils, (Pap.), 6 t h 1974, 106, 6 pp: Chem. Abstr., 84, 49728s (1976). (264) Hunter, G. L. K., Bucek, W. A,, Radford, T., J. FoodSci., 39(5), 900 (1974). (265) Huntoon, R. B., lnstrum. Food Beverage lnd., 2, 51 (1973).
ANALYTICAL CHEMISTRY, VOL. 49, NO. 5, APRIL 1977
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(628) Zola, A., Le Vanda, J. P., Parfums, Cosmet., Aromes, 7,31,39 (1976); Chem. Abstr., 85,51618~ (1976). (629) Zola, A., Le Vanda, J. P., Riv. ltal. Essenze, Profumi, Piante Off., Aromi, Saponi, Cosmet., Aerosol, 57(8), 467 (1975); Chem. Abstr., 84,
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Geb. Lebensmittelunters. Hyg., 65(4), 440 (1974): Chem. Abstr., 84, 42157w (1976). (632) Zutshi, S. K., Bamboria, B. K., Bokadia, M. M., Curr. Sci., 44(16), 571 (1975); Chem. Abstr., 84, 35175x (1976).
Pesticide Residues Wayne Thornburg Del Monte Corporation Research Center, Walnut Creek, Calif. 94598
This selective review presents the developments in pesticide methodology covering the period from December 1974 through November 1976. Papers selected for this review were ublished in journals which are readily available in major liraries. This interval has seen the introduction and acceptance of new automated instrumentation, including automated gas chromatographs and computer controlled systems. This review follows the general format and pesticide nomenclature used in the 1975 biennial review of Thornburg (366). Frear’s “Pesticide Index” (124)lists the common, trade, and chemical names of many pesticides, and the author has tried to use names found therein. Common names that appear in the Environmental Protection Agency tolerance regulations have been used where possible. Another useful publication edited by Shepard (334)is the “1976 Pesticide Dictionary” which is a compilation of the pesticides available commercially in the United States and throughout the world. Trade names, common names, and chemical names are cross-referenced wherever possible. Names of basic producers are also listed for each pesticide. “Residue Reviews,” under the editorship of Gunther ( l 4 2 ) , continues to be an excellent source of information on pesticide methodology. A total of 62 volumes has now been published. Preston and Bowman (304)authored “Pesticide Residues by Chromatographic Methods, Reprints of Selected Articles” which is a collection of 65 articles reprinted from past issues of the Journal of Chromatographic Science. The ACS published a symposium on “Bound and Conjugated Pesticide Residues”, ACS Symposium Series 29 ( 1 ) . This review period has been characterized by improvements and automation of instrumentation with increased reliability. Karlhuber and Eberle (200) discussed advances toward automation of pesticide residue determinations. These authors noted that only slow progress is observed in automation of pesticide residue determinations. This publication discusses the automated or semi-automated systems that are in current use. Hess and co-workers (155)described an automated system for the analysis of nitro compounds in water using a Technicon Instruments AutoAnalyzer I. McLeod (248) described systems for automated multiple pesticide residue analysis. This author notes that it is not yet possible to completely integrate all steps in a multiresidue method into a fully automated configuration. Cleanup of sample extracts, concentration, and transfer of cleaned-up extracts are steps that are difficult to automate. Johnson and co-workers (193) described an automated gel permeation chromatographic cleanup of animal and plant extracts for pesticide residue determination. Elution characteristics using Bio-Beads SX-3 gel and a toluene-ethyl acetate (1 3) elution solvent were determined for 16 nonionic chlorinated pesticides, 3 PCR’s, 14 chlorophenoxy herbicide esters, and seven organophosphate insecticides. High performance liquid chromatography (HPLC) has become an important tool in analytical chemistry; however, the availability of suitable detectors for pesticide and other trace analysis, generally has lagged behind development in column packings and other equipment.
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NO. 5,
APRIL 1977
Moye (270) reviewed the use of HPLC for the analysis of pesticides. I t was the intent of this article to provide a comprehensive review of pesticide related applications, suggest better utilization of existing columns, and describe approaches which could lead to practical analytical methods. Self and co-workers (331) discussed HPLC and its application to pesticide analysis. Julin and co-workers (198) described a selective flame emission detection of phosphorus and sulfur by HPLC. The instrument described in this article was custom built, but the technique should be applicable to detection of pesticides in HPLC eluates. Sampling, sample preparation, extraction, and cleanup of the extracts are still a very important part of successful pesticide analysis. A number of solvents and reagents, especially purified for pesticide analysis, are available and their use is highly recommended. Ford and co-workers (120) reviewed the sampling and analysis of pesticides in the environment. Lea (232)described a separation of pesticide residues from lipids prior to GLC analysis. Lipids were separated from dieldrin, endrin, and p,p’-DDE residues by saponification with ethanolic sodium hydroxide, acidification with dilute sulfuric acid, and adsorption chromatography on deactivated alumina, using petroleum ether as the eluant. This system will be successful only with pesticides that are stable to saponification. Dale and Miles ( 7 9 )described a simple partition chromatographic separation of pesticide residues from fats. The procedure used acetonitrile on a Florisil column. The fat was washed from the column with hexane and discarded. The pesticides were then eluted from the column with acetone. The efficiency of the cleanup column was between 97 and 100%. Kovac and co-workers (217) described the cleanup of extracts for pesticide analysis using the sweep codistillation method. Luke and co-workers (244) described an extraction and cleanup of or anochlorine, organophosphate, organonitrogen, and hydrocarion pesticides in produce, for determination by GLC. Leoni and co-workers (234)described preliminary results on the use of Tenax for the extraction of pesticides and polynuclear aromatic hydrocarbons from surfaces and drinking water. Tenax is a porous polymer based on 2,6-diphenyl-pphenylene oxide and appeared to be very satisfactory for the extraction of pesticides. Gunther and co-workers (143) described sampling and processing techniques for determining dislodgable pesticide residues on leaf surfaces. Popendorf and co-workers (303) presented a technique for collecting foliar dust samples that can be correlated to the fraction of pesticide residue which becomes airborne because of the activities of workers. Kearney and Kontson (204) described a simple system to simultaneously measure volatilization from and metabolism of pesticides in soils. Cochrane (67)described the confirmation of insecticide and herbicide residues by chemical derivatization. Finsterwalder (116)described a collaborative study of an extension of the Mills et al. method for the determination of pesticide residues in foods.
