ELECTRONIC SUPPLEMENTARY MATERIAL. Figure 1S.- Chemical structure of: a) alizarin; b) purpurin; c) pseudopurpurin; d) xanthopurpurin; e) quinizarin.
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- Δαρείος Βικελίδης
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1 ELECTRNIC SUPPLEMENTARY MATERIAL Figure 1S.- Chemical structure of: a) alizarin; b) purpurin; c) pseudopurpurin; d) xanthopurpurin; e) quinizarin. R 1 R 2 R 3 R 4 Name R 1 R 2 R 3 R 4 a Alizarin H H H H b Purpurin H H H H c Pseudopurpurin H CH H H d Xanthopurpurin H H H H e Quinizarin H H H H
2 Figure 2S.- Chemical structure of: a) curcumin, b) demethoxycurcumin, c) bisdemethoxycurcumin, d) cyclocurcumin, e) 5 -methoxycurcumin and f) dihydrocurcumin. a) H H H 3 C b) H H c) H H d) H H H 3 C
3 e) H H H 3 C f) H H H 3 C
4 Figure 3S- Chemical structure of: a) isophorone, b) safranal, c) picrocrocin, d) crocin and e) crocetin. a) H 3 C b) H 3 C C H 3 c) H 3 C CH d) HH 2 C H H H H 3 C CH
5 e) H H f) R R R= CH 2 H CH 2 H H H H H H H
6 Figure 4S.- Chemical structure of: a) indigotin and b) indirubin. a) H N N H b) N H NH
7 Figure 5S.- Ion chromatogram of madder obtained from: a) on line trimethylsilylation with pyrolysis of solid sample of dye at 600ºC; b) on line trimethylsilylation with pyrolysis of the extracted dye at 600ºC. a) Abundance Time--> b) Abundance Time-->
8 Figure 6S.- Ion chromatogram of curcuma obtained from: a)on line trimethylsilylation with pyrolysis of solid sample of dye at 600ºC; b) on line trimethylsilylation with pyrolysis of the extracted dye at 600ºC; c) on line methylation with pyrolysis of solid sample of dye at 600ºC. a) Abundance Time (min) b) Abundance Time- (min)
9 c) Abundance Time-->
10 Figure 7S.- Ion chromatogram of indigo obtained from: a) on line trimethylsilylation with pyrolysis of solid sample of dye at 600ºC; b) on line trimethylsilylation with pyrolysis of the extracted dye at 600ºC. a) Abundance Time--> b) Abundance Time-->
11 Figure 8S.- Proposed structures of principal mass spectra fragments of: a) 2-methyl-1- hydroindol-3-one; b) 3-[(trimethylsilyl)oxy]-1H-indole. a) b)
12 Table 1S.- Retention time, m/z and abundance values of characteristic ion (70 ev) of the principal derivatised compounds from madder obtained by pyrolysis-gc/ms using HMDS with and without extraction (6), 57(12), 76(4), 104(6), 149(100), 167(3), 223(6) (5), 76(4), 104(4), 149(100), 205(3), 223(4) (7), 73(37), 119(5), 147(100), 163(6), 193(3), 221(24), (12), 103(17), 140(8), 221(24), 251(11), 295(100), (89, 91(49), 104(14), 123(10), 149(100), 178(3), (6), 73(11), 105(5), 139(7), 238(2), 255(38), 269(10), (13), 59(6), 73(100), 89(2), 103(15), 117(10), 133(23), (29), 55(22), 73(94), 75(70), 117(100), 129(49), (10), 76(2), 104(3), 149(100), 251(16) t R Mass spectra data Peak #. Assignment (min) Characteristic ion (70 ev), m/z, (%) 1 Benzoic acid, TMS ester a (8), 51(9), 77(47), 105(68), 135(45), 179(100), 194(9) 2 2-propanone, bis-[(tms)oxy] a (12), 59(7), 66(6), 73(100), 87(4), 103(49), 117(4), 129(8), 147(14), 189(24), 219(9) 3 Dodecanoic acid, TMS ester a (19), 59(22), 73(100), 75(57), 103(13), 117(55), 129(30), 132(17), 145(12), 213 (2), 257(44), 272(2) 4 1,2-benzenedicarboxylic acid, di-2- methylpropyl ester a 5 1,2-benzenedicarboxylic acid, di-butyl ester a 6 Glycerol, TMS ether a (17), 59(12), 73(100), 89(7), 103(11), 117(37), 129(36), 133(10), 147(36), 189(6), 205(36), 217(2) 7 1,2-benzenedicarboxylic acid, di-tms ester a 295(18), 310(2) 8 1,4-benzenedicarboxylic acid, di-tms ester a 310(6) 9 1,2-benzenedicarboxylic acid, dibutylphenylmethyl ester a 206(16), 225(6) 10 1,2-dihydroxyanthraquinone (alizarin), mono-tms ether b 297(100), 312(32) 11 Propanoic acid, 2,3-bis[(TMS)oxy], TMS ester a 147(64), 175(3), 189(40), 205(11), 217(4), 292(29), 307(5) 12 Hexadecanoic acid (palmitic acid), TMS ester a 132(45), 145(29), 269(4), 313(99), 328(6) 13 1,2-benzenedicarboxylic acid, di-hexyl ester a 14 ctadecan-1-ol, TMS ether a (19), 57(18), 73(33), 75(52), 83(11), 103(25), 111(7), 125(3), 311(2), 327(100) 15 9,12-octadecadienoic acid (linoleic acid), TMS ester a (36), 73(100), 117(26), 149(37), 223(40), 262(9), 337(35) 16 9-ctadecenoic acid (oleic acid), TMS ester a (34), 55(47), 73(100), ), 129(62), 145(27), 185(8), 222(11), 339(60), 354(4)
13 t R Mass spectra data Peak #. Assignment (min) Characteristic ion (70 ev), m/z, (%) 17 ctadecanoic acid (stearic acid), TMS (30), 55(22), 73(89), 117(100), 129(50), 132(479, ester a 145(37), 201(7), 297(4), 341(99), 356(8) 18 1,2-dihydroxyanthraquinone (alizarin), di (20), 177(6), 296(5), 339(2), 369(100), 384(6) TMS ether b 19 1,4-dihydroxyanthraquinone (quinizarin), (20), 105(20), 147(16), 161(15), 177(10), 225(10), di-tms ether b ), 324(16), 354(100), 369(12) 20 1,3-dihydroxyanthraquinone (41), 149(10), 177(4), 238(3), 296(3), 369(100), 384(1) (xanthopurpurin), di-tms ether b 21 1,2-benzenedicarboxylic acid, bis( (10), 57(18), 83(4), 104(5), 149(100), 167(27), 279(8) ethylhexyl) ester a 22 1,4,5-trihydroxyanthraquinone, tri-tms (38), 149(8), 207(7), 339(5), 369(28), 399(3), 457(100), ether? b 472(4) 23 1,2,4-trihydroxyanthraquinone (purpurin), (39), 149(6), 207(6), 339(13), 369(6), 427(5), 442(100) tri-tms ether b 24 Isomer of 1,2,4- trihydroxyanthraquinone (5), 206(8), 311(3), 341(6), 370(4),412(7), 427(2), (purpurin), tri-tms ether b 442(100) 25 1,4,5-trihydroxy-3-methylanthraquinone, (22), 149(199, 207(17), 355(7), 384(4), 426(6), 456(100) tri-tms ether b a : Structure assigned on the basis of the comparison of MS data with those from the Wiley Library of Mass Spectra. b : Assignment is based on the interpretation of MS data.
14 Table 2S.- Retention time, m/z and abundance values of characteristic ion (70 ev) of the principal derivatised compounds from saffron obtained by pyrolysis-gc/ms using HMDS with and without extraction and TMAH. Peak #. Assignment t R (min) Mass spectra data Characteristic ion (70 ev), m/z, (%) 1 3,4-dimethylbenzaldehyde a (15), 44(27), 51(15), 63(12), 77(30), 91(29), 105(68), 133(92), 134(100) 2 3,5,5-trimethyl-2-cyclohexen-1-one (α-isophorone) a (22), 54(15), 67(8), 82(100), 95(10), 138(23) 3 5,5-dimethyl-2-methylene-3-cyclohexene-1-carboxaldehyde a (27), 44(24), 65(13), 19(36), 91(65), 105(32), 107(49), 121(100), 135(28), 150(7) 4 2,6,6-trimethyl-1,3-cyclohexadiene-1-carboxaldehyde (safranal) a (17), 51(9), 65(15), 75(25), 79(26), 91(85), 105(49), 107(100), 121(59), 135(9), 150(44) 5 2,6,6-trimethyl-2,4-cycloheptadien-1-one (eucarvone) a (36), 53(12), 66(38), 79(29), 91(49), 107(100), 122(13), 135(32), 150(73) 6 3,5,5-trimethyl-2-cyclohexen-1,4-dione (ketoisophorone) a (31), 68(100), 96(69), 109(13), 137(6), 152(35) 7 4-hydroxy-3,5,5-trimethyl-2-cyclohexen-1-one a (31), 55(18), 70(38), 82(9), 98(100), 112(45), 154(3) 8 2-hydroxy-3,5,5-trimethyl-2-cyclohexen-1-one a (18), 43(100), 55(55), 70(90), 83(31), 98(46), 111(26), 126(14), 139(35), 154(87) 9 2,2,6-trimethyl-1,4-cyclohexanedione a (97), 56(100), 69(51), 83(20), 95(22), 110(26), 139(70), 154(45) 10 2-(2-butenyl)-4-hydroxy-3-methyl-2-cyclopenten-1-one a (32), 55(24), 67(43), 81(33), 95(41), 109(39), 123(52), 137(47), 151(14), 166(100) 11 2-[(TMS)oxy]phenol a (19), 73(28), 75(85), 91(21), 107(7), 136(28), 151(100), 166(80), 182(48) 12 Benzoic acid, TMS ester a (11), 73(37), 77(40), 105(58), 135(46), 179(100), 194(5) 13 3,3,-dimethyl-1-[(TMS)oxy]cyclohexene a (23), 73(33), 85(6), 127(5), 147(2), 155(2), 183(100), 198(22) 14 Benzeneacetic acid, TMS ester a (11), 73(100), 75(31), 91(19), 16416), 194(14), 15 ctanoic acid, TMS ester a (18), 73(100), 117(55), 129(30), 147(13), 157(9), 173(4), 201(77) 16 1,2-benzenedicarboxylic acid, diethyl ester (Diethyl phthalate) a (8), 76(8), 105(8), 121(5), 149(100), 177(21), 193(3), 222(2) 17 2,2,9,9-tetramethyl-3,8-dioxa-2,9-disiladecane a (9), 73(32), 87(2), 101(5), 116(5), 133(6), 147(100), 177(14), 219(18) 18 2-[(TMS)oxy] propanoic acid, TMS ester a (13), 73(75), 117(64), 147(100), 190(16), 219(5) 19 2,2,8,8,-tetramethyl-3,7-dioxa-2,8-disilanonan-5-one a (12), 59(5), 73(100), 87(5), 103(53), 129(7), 147(15), 189(28), 219(10) 20 3-[(TMS)oxy]-3-butenoic acid, TMS ester a (14), 73(86), 129(12), 147(100), 156(16), 213(15), 246(2) 21 Butanedioic acid, di-tms ester (succinic acid) a (51), 129(8), 147(100), 247(12) 22 Dihydro-3,4-bis-[(TMS)oxy]-2(3H)-furanone a (14), 73(69), 101(18), 116(12), 131(10), 147(100), 217(7), 247(20), 262(6) 23 Dodecanoic acid, TMS ester a (100), 117(79), 129(37), 145(18), 257(87), 272(3) 24 2-methyl, 2-butenedioic acid, bis-tms ester (methylmaleic acid, (100), 97(12), 147(76), 184(60), 225(30), 259(62), bis-tms ester) a 25 1,2-benzenedicarboxylic acid, di-(2-methylpropyl) ester (13), 76(5), 104(13), 149(100), 167(3), 223(6) (Isobutyl phthalate) a 26 1,2-benzenedicarboxylic, dibutyl ester (Dibutyl phthalate) a (5), 76(4), 104(4), 149(100), 205(3), 223(4)
15 Peak #. Assignment t R (min) Mass spectra data Characteristic ion (70 ev), m/z, (%) 27 Glycerol, TMS ether a (10), 73(100), 103(25), 117(34), 133(21), 147(70), 175(2), 191(5), 205(58), 218(20), 299(3) 28 Trimethylsilylphosphate (3:1) a (5), 73(24), 133(8), 211(9), 283(5), 299(100), 314(15) 29 2,3-bis[(TMS)oxy]propanoic acid, TMS ester a (13), 73(100), 103(18), 117(12), 133(24), 147(74), 175(4), 189(46), 205(15), 292(40), 307(6) 30 Hexadecanoic acid (palmitic acid), TMS ester a (26), 57(11), 73(88), 75(66), 117(99), 129(48), 132(45), 145(32), 313(100), 328(6) 31 Nonanedioic acid (azelaic acid), di-tms ester a (12), 55(27), 73(100), 75(84), 97(10), 117(23), 129(34), 147(25), 152(20), 201(34), 204(17), 217(12)317(43) 32 1,2-benzenedicarboxylic acid, dihexyl ester a (11), 76(3), 104(3), 121(1), 149(100), 233(1), 251(6) 33 3,4-bis-[(TMS)oxy]butanoic acid, TMS ester a (100), 101(8), 117(9), 133(13), 147(38), 189(24), 233(26), 246(6), 321(7) 34 9,12-octadecadienoic acid (linoleic acid), TMS ester a (31), 55(42), 67(62), 73(100), 75(99), 95(40), 109(20), 117(35), 129(45), 150(20), 220(10), 262(18), 337(65), 352(3) 35 9-cis-octadecenoic acid (oleic acid), TMS ester a (92), 55(48), 73(100), 96(19), 117(63), 129(59), 145(25), 185(11), 339(57), 357(5) 36 9-trans-octadecenoic acid (oleic acid), TMS ester a (30), 55(40), 73(100), 95(37), 117(54), 129(55), 145(22), 339(38), 354(3) 37 ctadecanoic acid (stearic acid), TMS ester a (71), 55(24), 73(92), 75(69), 117(100), 129(50), 132(47), 145(37), 201(8), 341(94), 356(5) 38 1,2-benzenedicarboxylic acid, diheptyl ester a (8), 57(49, 76(2), 104(2), 149(100), 176(1) 39 2,3,5-tris--(TMS)-xylonic acid, gamma, lactone a (100), 102(7%), 117(27), 147(23), 189(13), 204(13), 217(20), 246(8), 349(1), 364(3) 40 1,6-anhydro-ß-D-glucopyranose, tri-tms ether (Levoglucosan, (10), 73(100), 129(13), 147(25), 191(11), 204(62), 217(55), 333(11) tris-tms ether) a 41 1,2-benzenedicarboxylic acid, diisootyl ester a (129, 57(21), 71(14), 83(5), 104(7), 132(3), 149(100), 167(29), 279(8) 42 1,2-benzenedicarboxylic acid, decyl octyl ester a (10), 55(6), 104(2), 149(100), 167(1), 251(4), 307(1) 43 2,3,5,6-tetrakis--gulonic acid, TMS ester a (100), 103(15), 129(43), 147(36), 191(29), 204(44), 217(57), 305(6), 466(1) 44 Crocetin b (58), 57(81), 73(100), 85(36), 115(8), 147(15), 170(15), 211(18), 249(8), 277(7), 457(4), 472(5) 45 Glucofuranose, penta-tms a (91), 103(12), ), 129(40), 147(29), 191(26), 204(24), 217(100), 273(2) 46 Glucopyranose, 1,2,3,4,6-pentakis--TMS (Glucopyranose, penta-tms) a a : Structure assigned on the basis of the comparison of MS data with those from the Wiley Library of Mass Spectra. b : Assignment is based on the interpretation of MS data.
16 Table 3S.- Retention time, m/z and abundance values of characteristic ion (70 ev) of the principal derivatised compounds from curcuma obtained by pyrolysis-gc/ms using HMDS with and without extraction and TMAH. t R (min) Mass spectra data Characteristic ion (70 ev), m/z, (%) Peak Assignment #. 1 3-methylphenol a (30), 43(36), 51(16), 55(22), 63(6), 67(8), 77(32), 79(32), 91(13), 107(100), 108(88) 2 2-hydroxy-3-methyl-2-cyclopenten-1-one a (44), 55(50), 69(49), 83(31), 85(25), 97(10), 112(100) 3 Tetrahydropyran-2-carbinol a ), 39(29), 43(32), 53(10), 57(33), 69(21), 79(12), 85(100), 108(20) 4 2,3-dihydrobenzofuran a (14), 51(7), 65(15), 77(3), 91(48), 110(5), 120(100) 5 3-ethylphenol a (30), 39(32), 43(62), 51(13), 65(8), 77(24), 91(14), 107(100), 122(32) 6 2-methoxyphenol a (13), 53(19), 63(7), 81(69), 95(8), 109(100), 124(84) 7 3-ethyl-2-hydroxy-2-cyclopenten-1-one a (12), 43(92), 55(84), 69(37), 83(49), 99(38), 111(15), 114(37), 126(100) 8 2-ethoxyphenol a (17), 53(15), 64(28), 81(18), 92(9), 110(100), 123(5), 138(7) 9 1,4:3,6-dianhydro-α-D-glucopyranose a (23), 41(34), 57(41), 69(100), 85(17), 98(20), 110(26), 125(4), 144(6) 10 Butanoic acid, TMS ester a (22), 57(13), 73(100), 75(55), 89(8), 117(38), 132(23), 145(37) 11 2-methoxy-4-vinylphenol a (9), 51(10), 63(7), 77(36), 89(6), 107(36), 121(2), 135(81), 150(100) 12 4-ethyl-2-methoxyphenol a (19), 55(20), 65(8), 77(12), 81(22), 91(12), 110(32), 122(10), 137(100), 152(50) 13 4-hydroxy-3-methoxybenzaldehyde a (23), 53(22), 65(14), 73(10), 81(33), 95(13), 109(25), 123(28), 136(18), 151(93), 152(100) 14 1,6-anhydro-β-D-glucopyranose (levoglucosan) a (24), 56(41), 60(100), 73(32), 85(3), 98(9), 119(10), 145(4), 162(1) 15 2-[(TMS)oxy]phenol a (25), 45(36), 65(23), 73(100), 75(95), 91(66), 136(21), 151(68), 169(51), 182(27) 16 β-[(tms)oxy]styrene; [(2-phenylethenyl)oxy] trimethylsilyl a (10), 162(10), 177(9), 192(100) 17 4-(4-hydroxy-3-methoxyphenyl)-3-buten-2-one a (34), 51(16), 63(11), 73(26), 77(27), 89(35), 105(18), 117(45), 134(19), 145(83), 150(21), 161(16), 177(100), 192(97) 18 4-(4-hydroxy-3-methoxyphenyl)-2-butanone a (52), 55(35), 77(38), 91(34), 107(5), 119(32), 137(100), 151(14), 161(9), 194(42) 19 ar-turmerone a (21), 83(100), 91(21), 119(71), 105(13),132(20), 201(17), 216(23) 20 β-turmerone a (12), 55(31), 77(30), 83(100), 91(39), 93(20), 105(87), 111(27), 119(39), 120(38), 135(5), 218(4) 21 α-turmerone a (8), 55(17), 77(14), 83(35), 91(20), 105(19), 120(100), 132(9), 217(5) 22 3-methoxy-4-[(TMS)oxy]benzaldehide a (9), 73(19), 104(5), 137(5), 163(7), 179(7), 193(52), 194(100), 209(43), 224(27)
17 t R (min) Mass spectra data Characteristic ion (70 ev), m/z, (%) Peak Assignment #. 23 [2-methoxy-4-(1-propenyl)phenoxy],TMS; Isoeugenol, TMS ether a (18), 103(9), 147(9), 206(100), 221(7), 236(45) 24 Hexadecanoic acid (palmitic acid), methyl ester a (90), 55(59), 69(35), 74(100), 81(15), 87(76), 98(12), 115(25), 143(30), 171(15), 213(6), 227(17), 239(12), 270(9) 25 ctadecanoic acid (stearic acid), methyl ester a (64), 55(40), 67(13), 74(100), 81(15), 87(65), 129(17), 143(27), 176(13), 199(23), 255(11), 298(7) 26 4-[(TMS)oxy]cinnamic acid, TMS ester a (18), 73(100), 91(6), 115(10), 147(11), 179(17), 219(99), 249(40), 293(83), 308(61) 27 4-[(TMS)oxy]hydrocinnamic acid, TMS ester a (12), 73(57), 147(12), 179(100), 192(61), 216(69, 271(16), 295(9), 310(17) 28 3-methoxy-4-[(TMS)oxy]benzoic acid, TMS ester a (18), 73(86), 89(12), 126(27), 141(8), 165(13), 193(29), 223(60), 253(48), 267(65), 282(30), 297(100), 312(63) 29 Hexadecanoic acid (palmitic acid), TMS ester a (27), 73(91), 75(74), 117(99), 129(47), 132(45), 145(29), 201(6), 269(3), 313(100), 328(6) 30 Nonanedioic acid (azelaic acid), di-tms ester a (28), 73(100), 75(92), 117(31), 129(39), 147(36), 152(24), 201(36), 295(7), 317(51) 31 3-methoxy-4-[(TMS)oxy]cinnamic acid, TMS ester a (18), 73(81), 89(8), 117(10), 191(13), 219(35), 233(9), 249(61), 279(10), 293(33), 308(53), 323(57), 338(100) 32 2-[(TMS)oxy]butanedioic acid (malic acid), TMS ester a (11),73(100), 75(32), 119(34), 133(14), 147(60), 175(5), 191(6), 233(19), 247(3), 336(4) 33 9,12-octadecadienoic acid (linoleic acid), TMS ester a (30), 55(35), 67(47), 73(100), 75(92), 81(41), 95(37), 109(15), 117(25), 129(29), 220(10), 262(9), 337(38), 352(3) 34 9-ctadecenoic acid (oleic acid), TMS ester a (39), 73(100), 75(81), 96(17), 117(68), 129(55), 145(23), 222(8), 339(47) 35 ctadecanoic acid (stearic acid), TMS ester a (35), 73(90), 97(5), 117(100), 129(48), 132(47), 145(35), 201(6), 298(9), 341(83), 356(9) 36 2,5-dihydroxybenzyl alcohol, tri-tms ether a (13), 73(97), 103(4), 147(16), 253(21), 267(8), 341(21), 356(100) 37 2-carboxy-2-hydroxypropanedioic acid (citric acid), tetra-tms ester a (100), 147(64), 183(8), 211(5), 273(70), 305(5), 347(14), 363(13), 375(13), 465(6) a : Structure assigned on the basis of the comparison of MS data with those from the Wiley Library of Mass Spectra.
18 Table 4S.- Retention time, m/z and abundance values of characteristic ion (70 ev) of the principal derivatised compounds from indigo obtained by pyrolysis-gc/ms using HMDS with and without extraction and TMAH. Peak #. Assignment t R (min) Mass spectra data Characteristic ion (70 ev), m/z, (%) 1 Benzeneamine (aniline) a (13), 66(34), 93(100) 2 Indole a (6), 50(3), 58(6), 63(12), 73(4), 89(28), 90(35), 117(100) 3 2-methylindole a (3), 51(5), 65(6), 77(10), 89(4), 103(9), 130(100), 131(66) 4 2,3-dihydroindol-2-one (indoline-2-one) a (17), 63(5), 78(36), 89(6), 104(81), 133(100) 5 Isomer of compound 4 a (18), 63(4), 78(55), 89(1), 104(100), 133(97) 6 2-methyl-1-hydroindol-3-one? b (20), 65(14), 78(31), 91(34), 104(87), 118(92), 130(54), 133(31), 147(100) 7 3-[(trimethylsilyl)oxy]-1H-indole? b (8), 73(36), 89(5), 104(3), 130(14), 146(3), 162(43), 190(14), 205(100) 8 2-aminobenzoate, TMS ester a (12), 65(30), 73(8), 75(18), 92(47), 104(9), 119(94), 120(96), 134(9), 150(40), 176(24), 194(100), 209(68) 9 unknown (8), 73(40),91(4), 117(5), 130(17), 146(13), 177(6), 188(2), 204(19), 219(100) 10 Product of silylating reactive a (10), 59(4), 73(54), 103(4), 117(6), 130(9), 144(9), 188(2), 202(5), 218(100), 233(82) 11 Dodecanoic acid, TMS ester a (20), 55(18), 73(93), 75(83), 95(4), 117(86), 129(44), 132(26), 145(19), 213(4), 257(100), 258(21), 272(2) 12 1,2-benzenedicarboxylic acid, bis(2-methylpropyl) ester a (7), 57(13), 76(5), 104(7), 132(2), 149(100), 150(10), 167(3), 205(1), 223(5) 13 1,2-benzenedicarboxylic acid, mono(2-ethylhexyl) ester a (12), 57(20), 70(12), 71(13), 83(5), 104(7), 113(6), 122(2), 149(100), 167(29), 279(8) 14 Tetradecanoic acid (myristic acid),tms ester a (26), 59(15), 73(100), 75(63), 117(71), 129(42), 132(27), 145(27), 159(4), 201(4), 285(62), 300(2) 15 9-hexadecenoic acid (palmitoleic acid), TMS ester a (35), 55(46), 73(99), 75(100), 96(19), 117(84), 129(72), 145(28), 194(13), 236(5), 311(80), 326(4) 16 Hexadecanoic acid (palmitic acid), TMS ester a (31), 55(23), 73(93), 75(72), 117(100), 130(51), 132(42), 145(31), 159(3), 201(6), 269(5), 313(92), 328(5) 17 1,2-benzenedicarboxylic acid, dihexyl ester a (11), 76(3), 104(3), 122(1), 149(100), 150(10), 167(1), 233(1), 251(6) 18 Heptadecanoic acid, TMS ester a (30), 55(22), 73(93), 75(63), 117(100), 129(48), 132(45), 145(26), 185(2),.201(6), 241(2), 283(3), 299(3), 327(78), 342(4)
19 Peak #. Assignment t R (min) Mass spectra data Characteristic ion (70 ev), m/z, (%) 19 9,12-octadecadienoic acid (linoleic acid), TMS ester a (42), 67(55), 73(100), 75(69), 81(30), 95(24), 101(8), 109(16), 117(26), 129(30), 135(17), 262(9), 337(27)u 20 9-octadecenoic acid (oleic acid), TMS ester a (36), 73(91), 75(100), 95(36), 108(21), 117(43), 129(45), 145(18), 222(5), 264(4), 339(28), 354(2) 21 ctadecanoic acid (stearic acid), TMS ester a (28), 55(28), 73(100), 75(71), 91(10), 117(88), 129(44), 132(42), 145(29), 185(6), 313(3), 341(64), 356(7) 22 1,2-benzenedicarboxylic acid, dioctyl ester a (7), 57(6), 71(4), 104(2), 121(1), 149(100), 167(1), 261(1), 279(6) 23 1,2-benzenedicarboxylic acid, decyl hexyl ester a (11), 57(4), 69(2), 104(2), 121(1), 149(100), 167(1), 233(1), 251(5), 307(2) 24 1,2-benzenedicarboxylic acid, decyl octyl ester a (8), 57(7), 85(1), 104(2), 121(1), 149(100), 167(2), 261(1), 279(3), 307(2) a : Structure assigned on the basis of the comparison of MS data with those from the Wiley Library of Mass Spectra. b : Assignment is based on the interpretation of MS data.
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