Chromatography’ €rich Heffmann, Western Regional Research laboratory, Albany, Calif.
T
HIS ARTICLE is based on chromatographic literature that has come to the author’s attention since his last review in 1962 (665),from December 1961 through December 1963, but excludes routine applications of known methods as well as topics covered in this issue by other reviewers. Chromatography in general has been the subject of several recent review articles (60, 712, 745, 932, 1314, 1333, 1362, 1690), but no new books on this broad topic have appeared, except for wine laboratory manuals (453, 1048, 2080, 1522). The Chemical Abstracts Service (268) has produced a bibliography on chromatography for the year 1962 on a n experimental basis, and a complete literature citation servICY has now been instituted by the
Journal of Chromatography. HISTORY
The history of thin-layer chromatography (TLC) has been sketched by Stahl (1485). This is the place to record that the recipients of the third and fourth Labline Awardr in Chromatography and Electrophoresis were W. E. Cohn (24) and the team of W. H. Stein and S. Moore ( 2 5 ) . I n both cases the contributions so honored were pioneering applications of ion exchange chromatography to biologically important compounds. THEORY
Columns. T h e theorctical basis of chromatography has been reviewed by AIunter (1091). Static and dynamic adsorl)tion experiments on silica gels (226, 408, 20467, aluminas (214,508), and charcoals (734) have demonstrated thr applicability of adsorption isotherms to the prediction of chromatographic, molility in columns (495, 502, 503, 2109). The effect of mixed adsorbents (496, 504) and mixed solvents (505, 3167) can also be accounted for. The sl’ecific surface structure of silica gels is rcsponsi1,le for their specific adsorption cffccts (254, 825, 826, 970, 1231, 1672Work conducted under a cooperative ngrecrnent with California Institute of Tccahnology, at fhe I )ivision of Biology,
P:tsnden:i, Calif. 2 A 1:ihor:itory of the Western I*tilieation Ikwxrcnh K: l>eveliiprnent Ilivision, Agricultural I 1473) and complexing (667, 602, 859, 9.93, 1223) chromatography. The separation of Ca, Sr, and T1 in a KC1-%n(l12 eutectic on silica or alumina columns is due to chemisorption (1302’). For partition columns, reversed-phase systems are now generally preferred; stationary phases such as 2-octanone (duo), tri-n-octyll)hosl)hine oxide (248, 250, %‘8), bis(2-ethylhexy1)orthophosphoric acid (1224,1720), and tributyl phosphate (323, 437, 468, 652, 1050, 1434) give excellent resolution. When tributyl pho.Qphateis used as the mobile phase, the rare earth elements are eluted in the order of decreasing atomic number (2’&4). In ‘I’M’ (13.9A), the migration of cations o n silica gel is deterinined by the ion csrhaiige iiroperties of the adsorbent and the coordination tendencies
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ANALYTICAL CHEMISTRY
of the solvent, e.g. butyl phosphate (1403) or acetonylacetone (1402). Molten salts have also been used as solvents (397). For the detection of alkali metal ions, tetracyanoquinodimethanide may be applied (396); use of violuric acid requires especially Ilurified silica gel (1401). TLC is now beginning to be used for the diagnosis of heavy metal poisoning (889) and in the separation of organometallic compounds (217 , 1366) and ~)hosphoricacid esters (828). Its application to inorganic anions has also been started (1398,f40O). Extensive schemes for the paper chromatography of inorganic cations (82, 425, 601, 1118, 1370, 1424, 1506) and anions (485, 575, 1566) have been published. .l novel way to apply cations to the origin of the chromatogram is to print an electrogram on the paper (1430). X ring oven can be w e d for (369, chromatographic separations 1 707). The solvent systems employed for cations have generally been of the familiar alcohol-acid type (244, 290, 339, 466, 803, 831, 938, Ygt9, ,976. 1071 1076, ll5,ql 1181, 1270: 1211, 1433, 1507, 1653, 1579, 1612, 1661), but it is evident that monophasic aqueons tems, such as inorganic acids (103, 537, Y l 4 ) and salts (651, 724, 805) alone can effect considerable fractionation of cations. The RF value is affected by such factors as acidity (275), temperature (939, 1299), and humidity (1299). Organic solvents such as chloroform (I33‘) and ether (58) have occasionally been used as developers, but mostly in systems containing acids (424, 438, 536, 59y1 1066). Aqueous methanol was used (341) with salts (899,12’68) or ammonia (529). The addition of EDTAlto solvent systems may reduce tailing (423,529). ]$is(2-e t hylhexyl) phosphat e (1f 81) , trihutyl phosl)hate (277, 711, 1103),and trioctylphosphine oxide (249,340) are also used in ])artition chromatography on paper. Cations are chromatographed in the form of coml)lexes (g3, 467, 914, 1281, 1440, 1 6 4 4 , with the aid of complex-forming solvents ( 1 7 . 59, 71, 103, 801, 923, 944:14051, or on impregnated paper to effert romplexing and precipitation. The following impregnating reagents have been reported: 8-quinolinol (461, 1108, 1113), diniethylglyoxime (723)! 1-nitroso-2naphthol (723), dithizone (1056), ruheanic acid ( I 11e ) , hydroxylamine (649) caprolactam (1436), rutin ( I Z l ) , manganeRe ferroryanide (.933), sodium thiosulfate antl 1)otahsiuin iodide (901), aluminum hydroxide (247), and ferric hydroxide (1494). Yew pal)er-rhromatographic se1)aration method> have aI*o been devised for variou-. anions of ~)hosl)horus(,96>342, 3HO. .$E.4 . 9 1 ~61.9, 11.53, 162’1) and iodinc (62:;). A new iini\~cr.*ald c ~ t e ( ~ i omethod ii for cations on ])ni)er chrnniat(~gr~nis con~
~
sists in spraying with 0.2y0 tetrahydroxyquinone in ethanol, followed by exposure to ammonia fumes (162). Carminic acid (657) and a benzidine spray, followed by exposure to furfural vapors (526), also stain many cations. Alkali metals are detected by silver nitrate, saturated with fluorescein (1325), and the alkaline earth metals by sodium rhodizonate (260). Eriochrome Cyanine R has been suggested for Be ( l o l l ) , I h m u t h i o l for 13i (13), potassium ferrocyanide for Cr (1020), titanium chloride for W (276), potassium iodide for TI (644), pyridinetricarboxylic, acid for ferrous ion (1077); hydantoins ( I 151), sulfanilamides ( 5 ) , and 1-nitroso-2-naphthol (880) for Co; p - dimethylaminobenzylidinerhodanine for .lu and I’d ( 1 6 ) ; and trisodium p h o q ~ h a t e followed , by zinc acetate, for I: (574). Organotin compounds have been detected by diphenylcarbazole (1294) and dithizone (534); the latter was also used for organic mercury compounds (92). aigeneral spraying reagent for anions is prepared from sodium fluorescinate and silver nitrate (1242). Yitrites may be detected by antistine (1580), sulfates and Ilyrosulfates by the Haines-Isherwood reagent (1324), pyrophosphates and polyphosphoric esters by the Kolloff reagent ( 7 2 9 , and phosphoric acid ester> that are not easily hydrolyzed may be first oxidized by spraying with hydrogen peroxide and ferrous sulfate (1643’). Traces of inorganic ions, including phosphorous compounds (1307), may be detected by activation anal (435,1119).
For the quantitative determination of inorganic ions in paper chromatograms, the lisper is either ignited in a Schoeniger flask (417, 426, 1468) or a-et-ashed (10S,9. 1309). Other possibilities are the ap1)lication of retention analysis (100. 172, 1738, 1739), spot area measurement* (15, 20, 99, 762. 5’18, 883), densitometry (672). and elution, followed by colorimetry (307, 1096, 1436, 1723), iodimetry ( 1 4 ) , flame qpectrophotometry (12 @ ) , inipedance measurement (206), or ring-oven determination (242). Hydrocarbons. Although gas chromatography is no\v the rncthod of choir(. for scliaration of hydrocarbons, intc,rcst in thcx irnl)rovcmmt antl allplication of liquid chromatogral~hy continucs. I n addition t o thc conventional frartional elution from silica gel columns (3.94, 850, 1578), very long (294, 464) arid reuseable alumina columns, operating analogous to gas chroniatogral)hic cdumn,G are now in use (778). Coupled colurnnr (I?%), disl)lacrment ( I l 6 4 ) , linear elution ad,wrl)tion (1460).and frartional iirrril~itation (1380) chromatogral)hy have also been al)l)lied. S e w d u n i n liackinp were tried, such as a butadiene-
acrylonitrile copolymer (1500) and picric acid, adsorbed on aluminum silicate (76). Factors affecting the chromatographic analysis of asphaltic petroleum on alumina were studied (628). Nitrogen dioxide and eosin may be used as color indicators for hydrocarbons on adsorption columns (1568) and color photography under ultraviolet light for documentation (295). Even chromatography on acetylated (1128), silica gel- (659) or paraffin oil(910) impregnated, and plain (984, 1278) filter paper is being used occasionally for the fractionation of hydrocarbons (1061), their sulfonic acid (366, 1 6 6 4 , or mercuric acetate (713) derivatives. Evaporation of the solvent during ascent seems to intprove the separation (1280). For T L C , silica gel (719, 885, f Z f 4 ) , alumina (829, 885), and acetylated cellulose (62, 1719) are quite suitable. Olefins may be chromatographed as mercuric: acetate addition compounds (1262). Two universal detecting reagents, applicable to T L C of hydrocarbons, are sulfuric acid solutions of dichromate and permanganate (436). Alcohols. Only polyhydric alcohols were chromatographed in uncombined form on paper (72, 660, 710, 11 76, 1632, 1685). Monohydric alcohols were first converted to monoalkyl sulfates (178), mercuric acetate addition compounds (1013, 1759), or urethan derivatives (52). Cellulose powder columns have been used for both mono- (1537) and polyhydroxy (405) compounds. Acetoxyanthracenes are oxidized on alumina columns in presence of alkali (509). Various peroxides are separated on silica gel columns (8116, 887). Polyols have also been fractionated by T L C on alumina (19) or silica gel (1536, 1694, 1734). The latter was also employed in separating 3,5-dinitrobenzoates (375) and peroxides (839) Reagents suitable for the detection of diols are either Tollens’ reagent on thin-layer plates (118, 884),or borax and a n acid-base indicator on paper chromatograms (1653). Inositol was detected by a bioautographic method (926). Carbonyl Compourtds. Paper chromatography of uncombined monocarbonyl compounds is also relatively rarely used (787, 1157, 1335, 1684). Their 2,4-dinitrophenylhydrazones separate easily in partition (48, 476, 590, 2012) or adsorption (1165) systems on paper and on partition (317) and adsorption (1385) columns. Girard hydrazones may be prepared a t the starting line just prior to paper chromatography (821, 892). The syn and anti isomers of 5-nitrofuraldoxime were separated on a column of nickel p- and 7-picoline thiocyanate (804). T L C is adaptable to the separation of uncombined aliphatic (998) and aromatic (887, 121 5 ) carbonyl compounds as well as their 2,4-dinitrophenylhydrazones (31, 177, 1117 ) and
even acetals (860). The chromatography of plant anthraquinone derivatives has been reviewed (659) and methods for their separation on paper (131, 776), thin-layer plates ( 1435), and polyamide columns (689) have been described. Khellin and visnagin separate readily on polyamide-impregnated paper (488). Carbohydrates. Saccharide mixtures are effectively fractionated on active charcoal (1331, 1332, 1556). While partition columns have long been used for sugars (617), the partition on ion exchange resins is a recent developSpecial column ment (346, 1347). procedures are available for neuraminic acid (958), sucrose palmitates (1055), sugar acetates and ethers (1726), 2,4dinitrophenylosazones ( 13 8 4 , and carbohydrate degradation products (215). Dextrans may be separated by gel diffusion on agar columns (715) and acidic polysaccharides by complexprecipitation chromatography (33, 34). Quite a number of new solvent systems have been devised for the paper chromatography of monosaccharides (737, 1073, 1354, 1501), their acetates (1045),phosphates (11, 1229, 1611), hydrazones (1532), 0-isopropylidene (82), methyl (1166, 1209), and triphenylmethyl (39) derivatives. Some work has also been reported on the effect of inorganic ions (519), impurities in the filter paper (1383), and presence of benzeneboronic acid (185) on the chromatographic properties (458) of carbohydrates. Special methods have been developed for the paper chromatography of amino sugars (1 154, 1225, 1276, 1390, 1745) and N-glucosides ( 14 1 ) , for disaccharides ( 1f r o ) , oligosaccharides (69), various carbohydrate thickening agents ( 1525), amylopectin and amylose (1563, 1615, 161 6 ) , heparin ( 9 7 ) , and other mucopolysaccharides (187, 1007, 1221). Progress in T L C of sugars has been reviewed (847, 1492). The layers were made of cellulose (119, 1388), calcium sulfate ( I758), or silica gel impregnated mith polyvinyl alcohol (1263) or buffer (1261). T h e method is applicable to methylated (538, 1261) and acylated (360, 400, 539, 1571) sugars, to neuraminic acid derivatives (573) and Ammoniaoligosaccharides ( 1703). containing solvents may aminate sugars (1699). No detecting reagent is needed when benzidine or p-anisidine is added to the solvent system (427). Special reagents have been reported for the simultaneous detection of sugars and organic acids (562), for differentiation between hexoses and pentoses (68, 176), between ketoses (1206),and between phosphorylated sugars (1462, 151 2, 1513 ) . New spray reagents are ammonium ceric nitrate (143), 3,6-dinitrophthalic acid (1070), and titanium chloride (1289). The benzidine (258), periodate
(1155), and silver nitrate (202) tests have been improved. Complex sugars may be treated with phosphoric acid on the paper and heated prior to spraying with a composite reagent (925). Charring is possible not only on glass paper (117), but also on ordinary filter paper (878). Quantitative methods are based on spot area determination (1l 7 3 ) , densitometry (769, 775, 1369, 1371 , 1588), elution (486, 1557), and a radiometric estimation in which the silver deposit from Tollens’ reagent is transformed to AgII3l (105). Phenols. Chromatographic methods for one group of phenols, the flavonoids, have been reviewed (1182, 1396). Silica gel columns are suitable for simple phenols (110, 978, f 7 4 6 ) , as well as flavonoids (402, 633) ; cellulose columns have been used for anthocyanins (259, 528), and nylon powder columns for various polyhydroxyphenols (429). While coupling of phenols prior to application (241, 330) or a t the starting line (891, 1645) is still practiced, frequently no difficulty is encountered in chromatographing various uncombined phenols on untreated filter paper (256, 380, 582, 585, 751, 851, 1038, 1732, 1740). I n other cases paper was impregnated with borate (305, 620, 621), carbonate (1230), various buffers (531, 1542), formamide ( 180, 576, 1064, 1205, 1609), dimethylformamide (738, 1543, 1609), ethylene glycol (180, 1598), vegetable oils (797, 1622), silicone (1378), molybdate (592, 620, 621), ferric hydroxide (817),or-in what was called “paper solubilization chromatography”-on resin-loaded paper (945). Special procedures were developed for vanilla flavoring compounds (J6, 278, 1541,1544). Thin-layer plates suitable for phenols of various kinds (812, 836, 1213) may be made from silica gel (70, 669, 935, 1282, 1379, 1392, 1569) or polyamides ( 144,934,1619,1630). Examples of detecting reagents are: the Fohn reagent (152, 1753), Fast 131ue 13 (685) and aluminum chloride (451) for flavonoids, Gibbs’ reagent for m-cresol (1663), Ehrlich’s reagent for resorcinol derivatives ( 6 ) , and diphenylpicrylhydrazyl for catechol derivatives (668). The complexes with p-nitrobenzenediazonium fluoborate are suitable for quantitative analysis (1393). Fatty Acids. Churacek (282) has reviewed the chromatography of lower fatty acids, and others have written reviews on the column (1365) and paper (1415, 1656) chromatography of fatty acids. For column chromatography silica gel is generally preferred (363, 864, 956, 1269, 1599, 1607) and unsaturated fatty acid eiters may be separated on silica columns impregnated with silver nitrate (1664) or in the form of mercury adducts (742, 888, 1 7 1 4 ) . VOL. 36, NO. 5 , APRIL 1964
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An acid-treated Florisil column was used for Clelabeled fatty acids (237). Except for some work o n T L C of fatty acid esters (40, 785, 1327), in situ reactions of unsaturated fatty acids (79S), and the separation of their esters on thin layer plates impregnated with silver nitrate (120, 1082), there has been a surprising lack of research activity in this area. Much use is still being made of paper chromatography with conventional (38, 492, 591, 820, 1320,1666) or reversed-phase (181, 246, 332, 414, 627, 641 , 678, 720, 1655, 1731) solvent systems. Errors due to volatility (1069) and esterification of fatty acids with alcoholic solvents (234) have been pointed out. Frequently, they are chromatographed in the form of various salts (135, 224, 225, 560, 1034, 1326), esters (283, 677, 765, 786). hydrazides ( y o ) ,and hydroxamates (894). For detection (159) and quantitative estimation (898) various indicators may be used. Alternatively, the fatty acids are converted to iron-cobalt rhodanates (474) or heavy metal soaps (22, 308, 632), which may be further transformed to the metal sulfides (22, 308). Salts with radioactive silver (739) and unsaturated fatty acids, iodinated with 1131, are determined radiometrically ( 2 ) . C14-labeled fatty acids are best quantitated by scanning both sides of the papergram (631). Other Carboxylic Acids. Tables of RF values for 120 organic acids may be found in reference 637. Chromatographic methods have been described for the fractionation of halogenated carboxylic acids (1031, 1410, 1573, 1755) and various keto (222, 189, 790, 1311, 1592) and hydroxy (273, 482, 789, 790, 821, 892, 905, 1.410) acids, as well as their lactones (865, 963) and peroxides (1241). Dicarboxylic acids separate well on silica gel (272, 854, 1220, 1236) or reversed-phase (844) columns, Reversed-phase systems were similarly used in T L C on silica gel (193, 1190, 1216) and in paper chromatography (845); a stationary phase of polyethylene glycol serves equally well for T L C of aliphatic (838) and aromatic (1210) dicarboxylic acids. Several paper-chromatographic methods have been specifically devised for metabolically important organic acids (245, 457, 522, 1008. 1239, 1368, 1730); there is also a T L C procedure for aconi tic acid (299) and a paper-chromatographic technique for naturally occurring, tetronic acids ( 1474). Auxins (1491, 1658) and gibberellins (896, 967, 1406, 1518) have been separated by paper as well as T L C . Other plant acids for which new chromatographic procedures have been described include ellagic acid (228), the bitter substances in hops (640, 1475), resin acids (79, 21 I , 349), and humic acids ( 1258). h general detection method for aro-
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ANALYTICAL CHEMISTRY
matic acids on paper chromatograms is based on photochemical oxidation by hydrogen peroxide in ultraviolet light (572). Identification methods have recently been described for benzoic acid derivatives (207, 858), such as aromatic hydroxy (352, 353, 454, 1348), keto (1133), nitro (316), and amino (367) acids, substituted cinnamic ( 1 4 7 l ) , phthalic (773), pyridine carboxylic (1078, 1079, 1363), pyridylacrylic (1226), and methoxypiperonylic (126) acids. Amino Acids and Peptides. I n addition to a general review of this field (223),there are now available summaries of quantitative (134), paper (1027), and thin-layer (197) chromatographic techniques. The most widely used technique is still conventional paper chromatography (840), and improved one- (1377) and two- (1353) dimensional procedures as well as discussions of the identification of amino acids by these methods (309, 462, 599, 1549) continue to appear in the literature. Research is also continuing on improved solvent systems for all kinds (262, 263, 564, 654, 1306, 1318, 1502, 1735) or for special groups of amino acids, e.g. basic (450, 1520), iodinated (150) and sulfur-containing (475, 1211) amino acids, and phenylalanine analogs (1094). Decomposition of amino acids during chromatography can be minimized by pretreating the paper with oxalic acid (?'l4,1086). Acetyl derivatives may be prepared directly on the paper prior to development (821,392)and cystine may be determined following oxidation on paper with hydrogen peroxide (1136). Special procedures permit the separation of various esters (153,398), particularly the analysis of C14-labeled methyl esters (1449), and of carbobenzoxy derivatives (420). The N-2,4-dinitrophenyl amino acids may be separated by chromatography on paper (766, 883, 1093, 1095, 1733) or columns of silica (809, 1016, 1519) or polyamide (674, 690, 1389) Various improvements in the detection of amino acids by ninhydrin have been described (171, 287, 811, 1550) and substitutes have been suggested, such as dimethylalloxan (18), 1,2,3phenalenetrione ( 1340) , chloranilic acid (85), chlorine and o-tolidine (91), and sodium pentacyanoaminoferrate (879). Aromatic amino acids give a characteristic fluorescence at liquid nitrogen temperatures (565), and guanidine compounds fluoresce green when the ninhydrin spray is followed by ethanolic sodium hydroxide (756). New detection methods were described for iodinated amino acids (556, 1303, 1765, 1766), methionine ( 1138),D-amino acids (1670), complexones (673), e-aminocaprolactam (344) its cyclic oligomers (34.3), and for peptides (1026, 1442). I
An extremely sensitive isotope derivative method of amino acid determination was published (101, 1716) and also some new methods for the quantitative analysis of thyroid hormones (1091, 1259), including the use of neutron activation (386, l 4 S l ) , and for the determination of proline (741). -4mino acids and peptides may be fractionated on thin layers of dextran gel (368). I n most cases silica gel was used for T L C of amino acids (297, 376, &6), but cellulose layers have also been employed (1105, 1728). Some losses have been found to occur as a result of adsorption (109). T L C has also been applied to the dinitrophenyl derivatives of amino acids (393, 1287, 1289, 1689). Proteins. Synge has discussed t h e use of adsorption in the purification of proteins (1.548). Suitable adsorbents for column chromatography are : hydroxyapatite (747), alumina gel (1160), and diatomaceous earth (1296). Viruses have been purified on calcium phosphate columns (816, 1452). The greatest successes have been scored with columns of dextran gel (140, 147, 565, 819, 917, 937, 985, 1005, 1057, 1143, 1200, 1254), although agar gel (681, 1245, 150/t, 1505) or synthetic polymers (682, 913) are also effective in protein fractionation. Specifically, molecular sieves have been used for sorting macromolecules and cell particles ( M l , 1504) according to size, for particle size (1505) and molecular weight (30,1712) determinations, and for measuring protein-binding phenomena (80, 716). Gel filtration is applicable to such practical problems as the desalting of proteins (931), removal of strontium from milk (544), purification of fluorescein-protein conjugates (336, 477), separation of bound and free vitamin Blz (?'YO), and the determination of protein-bound iodine in serum (937). I t has also been employed in the purification of polypeptide and protein hormones (432, 992, 1255, 1256) and in the fractionation of snake venoms (248, 149), histones (329), hemoglobins (56), and serum (471) and bile (1142) proteins. Novel approaches to protein fractionation include the antigen-antibody reactions on hydroxylapatite columns treated with immune 7-globulin (1337) and the use of diatomaceous earth columns treated with dextran or polyethylene glycol (1081). Dextran (368, 753) or hydroxylapatite (692) can also be used in T L C of proteins. Some work is still being done with filter paper (121, 372, 586, 696, l a w , 1391, 1574, 1 6 3 1 ) ~ frequently in combination with electrochromatography. When a mixture of histone and its antiserum was chromatographed on circular paper, specific immune precipitates could be detected (151).
Nucleic Acid Components. Various purines have been separated by T L C (252), but paper chr3matography (8, 50, 1246) is still mort: popular. New detection reagents for purines are chloranilic acid (85) and bromine, followed by ammonis, vapors (293). Ultraviolet absorptior spectra of purines and pyrimidines can be determined directly on the filter pa ier (442). Mangold has reviewed T L C of nucleotides and nucleic acids (988). Xucleosides (760, 975) and nucleotides (186, 760, 1349, 1357) are readily fractionated by T L C for this application cellulose pomder layers are apparently superior to filter paper (1284). Improved paper-chromatographic methods for nucleosides (904) and nucleotides (43, 121, 869, 1026, 1085, 1152, 1523) and a new partition column for nucleosides (618) have also t e e n described. Polynucleotides and nucleic acids may be fractionated on columns of dextran gel (176, 201, 381, 541, 1419, 1567, 1750), calcium phosphate (123, Zag), or silica gel (410). Kieselguhr columns impregnrited with methylated albumin (846, 882, 1538) and polynucleotide-cellulose columns (10, 656) deserve further exploration. Some work has also been reported on the application of paper chromatography to oligonucleotides (322, 1704) and nucleic acids ( 1 11, 1427). Alkaloids. Salts of various alkaloids have been separated on adsorption columns of basic a n d neutral alumina (166-169) or silicic acid ( 2 9 ) , but most investigatorr; prefer partition columns, usually with a buffer as the stationary phase (279, 358, 861-863, 927, 1350, 1594, 1662). Similarly, while adsorption chr2matography on paper (320) or thin la3 ers of adsorbents (296, 306, 387, 449, 722, 867, 965, 1068, 1130, 1283) is used to some extent, paper partition chromatography is apparently superior (943) and the bulk of the research work on alkaloid separations continues to be done in this area (1135). Extensive d a t a have been presented for Strychnos (227, 1002, 1675), Rauwo&a (866, % 1 ) , Amaryllidaceae (570), Erythroxylaceae (600),opium (73, 146, 212, 774), and ergot (21, 962) alkaloids. Alkaloids may be acetylated on the paper prior to development (890). Buffered paper gives the best results (361), and some work has been reported on paper containing different buffers in diffeernt segments (1754). Paper impregnated with tributyrin was used at high temperatures (1530). Formamide, used for impregnation, should contain some ammonium formate (1268). Paper chromatography may be used to determine the optimum p H for countercurrent distribution (1676) and for quantitative analysis (740). Two new color reactions are: the general test with sodium tetraphenylborate
and a 3-hydroxyphenyl-7-benzopyrone ( 1129) , and the specific test for nicotine and powith l-chloro-2,4-dinitrobenzene tassium hydroxide (735).
Other Nitrogen Compounds. Except for t h e separation of methylamines on a n adsorption column (391),the separation of aliphatic amines was carried out by either paper (154) or T L C (1686). Some strongly adsorbed amines a e r e fractionated on nonbound alumina layers (1059). I n the analysis of organic bases by paper chromatography, errors may be due to low recovery ( f 3 5 8 ) or to double zoning as a result of complex formation with trichloroacetic acid (1305). Procedures have been devised for a number of tissue amines (413,487, 1067, 14G7), particularly the catechol amines (12, 622, 872, 1367, 1671, 1683, 1705) and various aminoalcohols (209, 533, 196, 1156, 1174, 1345, 1554, 1760). New paper-chromatographic methods have also been described for indoles (653, 1477), nitroanthrimidines (270), quinoline-.V-oxides ( I 1 58), pyridylcarbinolS-oxide and related compounds (1661), substituted trinitrobenzenes (303, 304) , cyanamide derivatives (1564), substituted cinnolines ( 5 7 l ) , aliphatic diamines ( 1 150), and alkylamnionium salts (536, 758). Aromatic amines have been separated on adsorption columns (78, 235), by T L C (634), and by paper chromatography (1172, 14.56, 1517). The latter has also served to identify various synthetic sweetening agents (480,721). Paper-chromatographic methods have been described for the bile pigments (972, 973, 103.5) and their diazo derivatives (554, 779, 1121). Uroporphyrin and coproporphyrin isomers Rere resolved by paper (319) and T L C (760). Chlorophylls and other chloroplastid pigments have also been separated by both paper (695, 748, 1497, 1657) and T L C (37, 419, 1310). Terpenoids. T h e chromatography of essential oils h a s been reviewed by Polonsky (1244)and T L C of terpenoids by Stahl and Jork (1490). While there is no doubt about the superiority of gas chromatography for quantitative analysis, liquid-solid adsorption (824, 902, 1051, 1375) and liquid-liquid partition (1718) columns are quite valuable, especially for preparative uses. Alumina is a p t to induce alterations in some adsorptives, e.g. ubiquinones (658). T L C is particularly useful for the fractionation of saponins (403, 1186, 1188, 16.90, 1701), other glycosides (815), and other triterpenoids (717, 1690). I t has been applied to carotenoids (61.3, 1298), ubiquinones (1669), farnesol derivatives (1610), and camphorsulfonate (902). Analogous results have been obtained with conimercial adsorbent-coated filter papers (749,
1457). Paper was also impregnated with petroleum jelly ( 5 2 ) , polymethylsiloxane (1496), paraformaldehyde (684), nitrocellulose, l-bromonaphthalene, etc. (1184), b u t untreated filter paper could be used for saponins (856, 1626), terpene alcohols, aldehydes (603), and acids (1180). Steroids. Keher has recently surveyed this very active field (1124). Other reviewers have dealt with more restricted topics, such as T L C (107, 1680), chromatography of Digitalis glycosides (130) and of bile acids and alcohols (798), and paper chromatography of estrogens (841,1148). Classical adsorption chromatography on alumina (822,1295,1376,14Q7,1606, 1647, 1698), silica (326, 483, 607, 664, 826, 1141, 1194, 1469, 1761), calcium sulfate (1016), Fuller's earth (77), and Florisil (191) is still one of the most valuable techniques here, supplemented by gradient elution (1295, 1647) and modifications of the adsorbents, e.g. specific ( 1194) and silver nitrate-impregnated (607) silica gel. Adsorption chromatography on a n ion exchange resin was used for the separation of C18 (1404) and C21(1014) steroids. Partition (610, 386, 1147, 1149) and reversed-phase partition (269, 647, 648, 769, 1014) columns, especially in conjunction with gradient elution (481, 647, 648, 1290), are very useful for quantitative work. Qualitatively, they give the same d a t a as paper chromatograms (767). T L C (1455) and spread-layer chromatography (1386) have by now been successfully applied to all classes of steroids. Thin-layer partition chromatography uses a mixture of some inert carrier and gypsum to support a stationary phase of formamide (1624), undecane (1202), or paraffin oil (1044). All three techniques are applicable to sterols (54, 115, 233, 794, 815, 1083, 1131, 1623, l763), vitamins D (354, 1141) , steroidal sapogenins ( I 14, 969, 1373) and alkaloids ( 7 , 1?3, 1373), bile acids (431, 691, 693, 875, 1387), cardenolides (688, 954, 1441, 1511) and bufadienolides (730, 1509, 1756), and steroids related to the estrogenic (377, 472, 667, 763, 936, 953, 1025, 1533), androgenic (253, 399, 407, 557, 867, 1024, 1292), progestational (53, 142, l 4 9 9 ) , and adrenocortical ( 9 , 113, 511, 752, 1017, 1039, 1356, 1387) hormones. A sensitive color reagent for many steroids is vanillin in ethanolic sulfuric acid (1012). The incorporation of various fluorescent materials in the adsorbent permits nondestructive detection of steroids in ultraviolet light (189, 606, 1083). Planimetry (1764) or elution (246) may be employed in quantitative estimation. When scintillation counting was used, the steroids may be recovered from the phosphors by T L C ( 1301). VOL. 36, NO. 5 , APRIL 1964
19 R
Occasionally, impregnated glass-fiber
(414, 433, 1503) or filter paper (513, 870, 1042, l o @ , 1460, 1457) have also served in adsorption chromatography. Derivatives, such as the azo dyes of estrogens (999, 1438) are now likewise only occasionally used in partition chromatography on filter paper, but Edwards (415) has described a two-dimensional system for corticosteroids which involves formulation on the paper prior to the second development. Modified solvent systems have been described for sterols (443,906),vitamins D (439, 919), steroidal saponins (1187) and alkaloids (1414, 1516), bile acids ( 1 180), cardiac glycosides (593, 1606, 1717), and steroids related to the estrogenic (81.4, 569, 768, 955, 1360, 1596), androgenic (44, 239, 452, 782, 955, lSO4, 1376), progestational (955, 117 7 ), and adrenocortical (220, 955, 1454, 1596) hormones, particularly aldosterone (733, 1189). Pan has proposed group reagents for steroid ketones and alcohols ( I 178) and for steroid ketols and glycols (1179). Vanillin-perchloric acid has been recommended for the detection of steroids related to pregnanetriol (460) and 1-(2pyridylazo)-2-naphthol and cobalt nitrate for pregnanolone glucuronide and related compounds (327, 903). Improved techniques for the application of known detection methods have also been described (88,434, 568, 661 , 1636). I n quantitative analysis on the filter paper, the antimony pentachloride reaction was recommended for cholesterol (163), a semiautomatic fluorimetric method for cardiac glycosides (842),and a triangulation method for rapid estimation of estrogen metabolites from a densitometer scan (895). Elution of steroids from paper chromatograms was investigated (526), effected by special apparatus (1581), and applied, usually after staining (74, 7 5 ) . Radioactive estrogens were counted following direct immersion of the paper in a liquid scintillator (1521). Other Lipids. I n addition t o review articles on t h e chromatography of industrially important lipids (990, 1395) and the phospholipids (1001), there are also several new reviews dealing exclusively with column (324, 3251, paper (1319), glass paper (626), and TLC (32,987,989,1201). Reversed-phase solvent systems are best for partition chromatography of simple lipids on paper (728, 796, 1139, 1617), thin-layer plates (784, 788, 791 , l o & ) , and columns (679). For adsorption chromatography of simple lipids, silicic acid-impregnated paper (139), unbound layers of alumina (2623), or conventional thin layers of silica gel (42, 7 9 4 , silver nitrate-impregnated silica gel (87), and hydroxyapatite (694) may be used. For column chromatography of com-
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0
ANALYTICAL CHEMISTRY
plex lipids, silicic acid is the adsorbent of choice (348, 404, 909, 946, 947, 1286, 1341 , 1608), although alumina was recommended for cerebrosides and phospholipids (635, 948). The decomposition of lecithin on alumina may be decreased by working a t low temperatures (1293). Other suitable adsorbents are: Florisil (1029), ammonium silicate (1476), and cellulose powder (1428). Gradient elution increases resolution (909, 948, 1342, 1428). Silica gel is likewise the preferred adsorbent for phospholipids (388, 610, 703, 1364, 1443, 1444, 1667, 1763) and glycolipids (848, 1131, 1546, 1709) in TLC, spreadlayer (1445), paper (830, 1275, 1417, 1582, 1660) and glass-paper (318) chromatography. I n addition, paper has also been impregnated with zinc oxide (302) and silicon tetrachloride (759). -1variety of lipid stains are suitable for paper chromatography (700, 757, 807, 1547). The simplest detection method for TLC is charring (1264, 1697), but iodine (1439) or dimethyldichlorosilane (792) vapors are preferred if the material must be recovered. For quantitative analysis, the adsorbate is scraped off the plate either before (1654) or after (743) a suitable color reaction. The results compare favorably with those obtained by gas chromatography (188). Iaotope-derivative (991) and neutron-activation (158, 1116) procedures were described. Vitamins. Chromatography on columns of alumina or weaker adsorbents (138, 1101) has been used for vitamins d (1006) and E (1751). T L C of vitamins was reviewed by Bolliger (174). Although it gives excellent resolution of fat-soluble vitamins (153, 238, 1668), some investigators still employ the less convenient reversed-phase partition on paper (744, 764). (For vitamins D , cf. section on Steroids.) I n the field of water-soluble vitamins, cellulose columns were used for ascorbic acid (328, 1570), active clays for cobalamin (1249), and columns of polyethylene powder for thiamine (1227). T L C was applied only to vitamins Bi (351) and Blz (286). Most work in this field is done by paper chromatography, the quantitative determination of ascorbic acid leading the list (663, 1049, 1053, 1670, 1762). I n addition to general methods for the vitamin B complex (164, 1437) specific paper-chromatographic procedures have been devised for the derivatives of thiamine (1693), riboflavine (704, 707, 868, 1600), nicotinic acid (165), pyridoxine (371, 1098), and cobalamine (98, 232, 321, 1010, 1198). Antibiotics. Column chromatography was used only for preparative work (1572, 1641, 1736). Much is now known about the behavior of various antibiotics in paper chromatograms (447, 940, 1185) and this forms
the basis of their identification by chromatographic spectra (1127). When bufferimpregnated filter paper is used (849, 1555, 1620))the RFwill depend on the p H (128, 129) and salts may affect the zone shape (1470). With formamide-impregnated paper double zoning may occur (156); the addition of sodium formate is recommended (157, 1737). I n reversed-phase paper chromatography, aqueous mobile phases are chosen, preferably buffers (3, 1408, 1409 1695). TLC has only recently been introduced into this field (1132, 1185). Layers of silica ( l l 4 6 ) , alumina (928), and carbon (203) are suitable. The detection methods in both paper and TLC are similar, bioautographs being the most popular (1052, 1063). Chemical detection methods vary with the characteristics of the antibiotic group: Penicillins and cephalosporins may be located by treatment with dilute alkali, followed by starch-iodide ; penicillinasesensithe compounds are distinguished by substituting penicillinase for the alkali (1585). Alternatively, the penaldic acids, ohtained by alkali and magnesium chloride treatment , are detected by Schiff's reagent ( 2 1 2 ) . dntimony trichloride has been proposed for tetracyclines (1171) ; sodium hypochlorite, followed by starch-iodide, for fradiomycins ( 1539) ; and hydroxylamine, followed by ferric chloride for cycloheximide derivatives (907). Other Pharmaceuticals. Applications of T L C in the pharmaceutical field (517, 649, 951, 1000, 1328, 1493, 1681) and the chromatography of phenothiazine derivatives (57, 155) have recently been reviewed. T L C (66, 136, 1659) and the analogous spread-layer technique (1351) permit the rapid identification of drug mixtures. Barbiturates (296, 411, 479, 921, 1545), various tranquilizers (65, 296, 421 , 456, 1195, 1614), analgesics (136, 514, 1351), sulfonamides (814, 827), and anthraquinone drugs (687) have been chromatographed this way. Partition chromatography on columns mas only used in two instances: the determination of barbiturates (1708) and of amphetamine (1074). New paper-chromatographic techniques have been described for various narcotics (542, 893, 1196, 1534, l649), barbiturates (161, 315, 362, 406, 650, 833-836, 900, 11 25, 1287, 151 5, 1631, 1742) and other sedatives (216, 392,409,421,1088, 1122, 1352, 1529, 1639, 1652), analgesics (288, 485, 604, 727, 1140, 1636, 1642, 1648, 1650) antihistamines (1635, 1638, 1639), sulfonamides (190, 650, 1227, 1411, l472), antiseptics (102, 194), isonicotinic acid hydrazide (84, 86), phenazine dyes (145, 1277), sulfonyl ureas (255), diuretics ( 7 7 l ) , zoalene (1463),ephedrine (675) and nikethamide derivatives (289).
Pesticides. Partition (1, 806, 1169) and adsorption (261, 333, 726, 755, 979, 1065, 1193, 13b9, 1431, 1626) columns are valuable i,i the preliminary purification and prepai*ativeisolation of pesticides. T L C is primarily employed as a qualitative methcd (64, 125, 1212, 1217, 1344, 1613, 1657, 1741, 17-43). Three new reviews on paper chromatography are available :547, 966, 1446). It was used for qualitative analysis of herbicides (484) and chlorinated (338, 441, 881, 1060, 1062, 1558, 1625) and phosphorus-containing (444, 546, 800, 852, 1137) pesticides. Quantitative estimation of the latter is best accomplished by ashing and colorimetric phosphate determination (445, 1134). Dyes. Recent developments in t h e chromatography of food colors have been reviewed by Sadini (1336). Except for a procedure in which v a t dyes were separated in a chromatographic tube filled with cotton yarn ( 7 4 l ) , all the newly published methods were based on either paper 141,94,754, 1047, 1084, 1207, 1234, 11‘88, 1336, 1479, 1640) or TLC (89, ’;93, 1072, 1272, 1343, 1727). I n paper chromatography, adsorption phenomena are troublesome and may be circumvented by impregnating the filter paper with 1bromonaphthalene (264, 635) or cetyl alcohol (285), or by addition of a n alkylphenol to the dye solution (855). The spots elongate, depending on the amount (1266, l744), and reflectance measurements may be used for quantitative determination (1515’0). Sulfur Compounds. S i c k e l sulfide, deposited o n silica gel, was found to be t h e best adsorbent for sulfurcontaining aromatic petroleum concentrates (520). A general method of detecting sulfur compounds on papergrams is to spray with potassium iodide in hydrochloric acid (365). Quite a few chromatographic meth3ds are now available for the sulfonic acids (179, 702, 731,867,1106,l42~,1499).I n addition, procedures have bel:n devised for sulfinic acids and sulfonyl chlorides (583), sulfoxides (1587), mercaptans and mercaptides (877, 1713) sulfidimines (473) thiophosphoric acid (1217 , 1624) and thiophene (337) derivatives, mercaptobenzothiazoles (1614 ) , and for thiram (1248). Miscellaneous. On exposure t o bromine, m a n y aromatic compounds o n papergrams liberate hydrogen bromide, which m a y be detected b v spraying with dimethyl yellow (813). Chromatography h a s p layed a part in the analysis of plasticizers :19B),surfactants (218, 1 2 14, 1312, 1559),accelerators and antioxidants (1099, ’ l o o ) , mordants (1 123) photographic developers (1033), and unknown toxins (312 ) . Chromatographic methods for high polymers have been rcviewed by Samsonov (1346). They hitve been used for
various synthetic resins (1700), e.g. polyethylene glycols (643) and polyglycerols (231), for urea-formaldehyde resin intermediates (732) and urea and melamine adhesives (1235). LITERATURE CITED
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(8) Adamanis, F., Malejka, D., Pawelczyk, E., Poltkowiakowa, Z., Poznan. Towarz. Przyjaciol .Vauk, Wydzial Lekar., Prace Komisji Farm. 2, No. 2, 15 (1962). ( 9 ) Adamec, O., Matis, J., Galvanek, M., Lancet 1962-1, 81; Steroids 1, 495 (1963). (10) Adler, A. J., Rich, A., J . Am. Chem. SOC.84,3977 (1962). ( 1 1 ) Agarwal, D. P., Sanwal, G. G., Krishnan, P. S., Analyst 87, 758 (1962). (12) Agrawal, D. K., Rao, V. K. M., Indian J . Chem. 1, 232 (1963). (13) Agrinier, H., Compt. Rend. 253, 280 (1961). 114) Ibid.. a. 1980. ( i 5 j Ibid.; i 5 4 , 1850 (1962). (16) Ibid., 255, 2801 (1962). (17) Ibid., 257, 145 (1963). (18) Akabori, S., Narita, K., Fujii, Y., Ishii, J., J . Biochem. ( T o k y o ) 50, 424 (1961). (19) Akhrem, A. A., Kuznetsova, A. I.,
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(37) Anwar, M. H., J . Chem. Educ. 40, 29 (1963). (38) Aparicio, M., Grasas y A c e i h (Seville, Spain) 12, 109 (1961). (39) Applegarth, D. A., Buchanan, J. G., J . Chem. Soc. 1960, 4706. (40) Applewhite, T. H., Diamond, M. J.,
Goldblatt, L. A., J . A m . Oil Chemists’ SOC.38. 609 (19611. (41) Aragones-Apodaca, R., Inform. Quim. Anal. ( M a d m d ) 17, 53 (1963). (42) Araka, E., ‘VisshinIgaku 50,85 (1963). (43) Aras, A. J., Becker, M., Brown, A. L., Hass, G. M., Lab. Invest. 11, 65 (1962). (44) Ari, N., Turk Ijiyen Tecrubi Biyol. Dergisi 21, 149 (1961). (45) Arimura, A., Saishin Igaku 17, 1345 \ - - - - I
(1962). (46) Arnold, W., Buehrer, R., Euw, J. v.,
Luescher, E., Schindler, O., Stich, K., Zoller, P., Reichstein, T., Helo. Chim. Acta 46, 178 (1963). (47) Arx, E. v., Neher, R., J . Chromatog. 8 , 145 (1962). (48) Asatoor, A. M., Ibid., 7, 415 (1962). (49) Ashiaawa, T., Bunseki Kagaku 10, 443, 449, 555, 558, 683, 688 (1961). (50) Astvatsatur’yan, A. T., Aptechnoe Delo 10, No. 1, 21 (1961). (51) Astvatsatur’yan, A. T., Sbornik
Sauch. Trudov Rostov. Med. Inst. No. 10, 189 (1959). (52) .Attaway, J. A., Wolford, R. W., Alberding, G. E., Edwards, ti. J., ANAL. CHEM.34, 671 (1962); Ibid.,
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35, 234 (1963). (53) Auvinen, E. M., Favorskaya, I. A,, Vestn. Leningr. Univ. 18 ( l o ) , Ser. Fiz. i Khzm. No. 2, 122 (1963). (54) Avigan, J., Goodman, D. S., Steinberg, D., J . Lipid Res. 4 , 100 (1963). (55) Avizonis, P. V., Wriston, J. C., Jr., ANAL.CHEM.34, 54 (1962). (56) Awad, E., Cameron, B., Kotite, L., hature 198(4886), 1201 (1963). (57) Awe, W., Schulze, W., Pharm. Ztg., Ver. Apotheker-Ztg. 107, 1333 (1962). (58) Babko, A. K., Vdovenko, M. E., Zh. Analit. K h i m . 17, 820 (1962). (59) Babko, A. K., Vdovenko, M. E., Kopa, M. V., Zavodsk. Lab. 29(6), 645 (1963). (60) Baddour, R. F., Valbert, J. R., Mod. Chem. Eng. 1, 487 (1963). (61) Bader, H., Morgan, H. E., Biochim. Biophys. Acta 57, 562 (1962). (62) Badger, G. M., Ilonnelly, J. K., Spotswood, T. M., J . Chromatog. 10, 397 (1963). (63) B~aehler, B., Helo. Chim. Acta 45, 309 (1962). (64) Baeumler, J., Rippstein, S., Ibid., 44, 1162 (1961). (65) Ibid., p. 2208. (66) Baeumler, J., Rippstein, S., Pharm. Acta Helv. 36, 382 (1961). (67) Bailey, R. A., JVAS-A’S 3106,
Office of Technical Services, Washington, D. C., 1962. (68) Bailey, R. W., J . Chromatog. 8 , 57 (19621. (69) Bailey, R. W., Pridham, J. B., Chromatog. Rev. 4 , 114 (1962). (70) Bakshi, S. H., Krishnaswamy, S . , J . Chromatog. 9, 395 (1962). (71) Balakrishnamurtv. V. V.. J . Sci. Ind. Research (India) 20B, 453 (1961). (72) Balatre, P., Traisnel, M., Bull. SOC. Pharm. Lille 3 , 83 (1960). (73) Balatre, P., Traisnel, M., Delcambre, J. P., Ibid., p. 143. (74) Balcar, E., Biul. Inst. Roslzn Leczniczych. 7, 167 (1961). (75) Balestreri, R., Correale, L., Lotti,
G., Arch. “ E . Maraoliuno” Patol. Clin.
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VOL. 36, NO. 5, APRIL 1964
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( 7 7 ) Ballestic, F., Fr. Patent 1,328,349 (May 13, 1963). (78) Bansho, Y., Saito, I., Suzuki, S., Kogyo Kagaku Zasshi 64,1061 (1961). (79) Bardyshev, I. I., Cherches, Kh. A , , Meerson, L. A., Zh. Anal. Khim. 18(7), 895 (1963). (80) Barlow, C. F., Firemark, H., Roth, L. J., J . Pharm. Pharmacol. 14, 550 (1962). (81) Barnabas, J., J . Cniv. Poona Sci. Technol. 1961, KO. 20, 49. (82) Barnett, J . E. G., Kent, P. W., Nature 192, 556 (1961). (83) Barnum, H. M., Belg. Patent 620,176 (Jan. 14, 1963). (84) - 7,. -, Barreto. R. C. R., J . Chromatoa. 82 (1962).‘ (85) Barreto, R. C. R., Barreto, H. S. R., Pinto, I. P., Ibid., 6 416 (1961). (86) Barreto, R. C. k., Sabino, S. O., Ibid., 9, 180 (1962). (87) Barrett, C. B., Dallas, M. S. J., Padlev. F. B.. Chem. Ind. (London) \ -
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24 R
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(477) Fothergill, J. E., Nairn, R. C., Sature 192, 1073 (1961). (478) Fouarge, J., J. Chromatog. 9, 96 (1962). (479) Frahm, M., Gottesleben, A., Soehring, K., Arzneimittel-Forsch. 11, 1008 (1961). (480) Franc, J., Collection Czech. Chem. Commun. 24, 3881 (1959). (481) Francois, D., Johnson, D. F., Heftmann, E., AXAL.CHEM.35,2019 (1963). (482) Frankel, E . S . , McConnell, D. G., Evans, C. D., J . Am. Oil Chemists’ Soc. 39, 297 (1962). (483) Frantz, I. D., Jr., J . Lipid Res. 4, 176 (1963). (484) Fredrick, J. F., Phyton (Buenos A i r e s ) 17, 147 (1961). (485) Freundt, K. J., Arzneimittel-Forsch. 12, 614 (1962). (486) Fric, F., Kubaniova, O., J. Chromatog. 11, 127 (1963). (487) Friedhoff. A. J.. Van Winkle. E.. ~I
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