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. 2016 Sep 9;21(9):1204. doi: 10.3390/molecules21091204

Table 1.

Volatile compounds identified in R. roxburghii and R. sterilis fruits by GC-MS (n = 3).

No. Rt (min) Compounds Molecular Formula Molecular Weight Main Mass Fragments Area% in RR Fruit Area% in RS Fruit
1 3.12 3-Furaldehyde C5H4O2 96 67, 39 - 0.01 ± 0.001
2 3.17 Furfural C5H4O2 96 67, 39 0.67 ± 0.03 0.57 ± 0.02
3 3.34 3-Hexen-1-ol C6H12O 100 83, 67, 41 - 0.53 ± 0.01
4 3.40 4-Methyl-octane C9H20 128 112, 85, 71, 69, 43 0.83 ± 0.04 0.17 ± 0.01
5 3.41 Ethyl benzene C8H10 106 91, 74, 51, 27 - 0.20 ± 0.02
6 3.48 o-Xylene C8H10 106 91, 74, 51 0.3 ± 0.003 -
7 3.48 p-Xylene C8H10 106 91, 74, 51 - 0.28 ± 0.02
8 3.67 Styrene C8H8 104 78, 51, 27 1.53 ± 0.05 0.04 ± 0.003
9 4.27 5-Methyl-nonane C10H22 142 112, 85, 65, 43 0.16 ± 0.003 -
10 4.94 2-Ethyl-1-hexanol C8H18O 130 112, 83, 57, 29 0.23 ± 0.01 -
11 4.99 d-Limonene C10H16 158 137, 121, 93, 68, 41 0.22 ± 0.01 0.17 ± 0.01
12 5.02 Benzyl alcohol C7H8O 108 79, 51 - 0.02 ± 0.002
13 5.07 1,6-Dimethylhepta-1,3,5-triene C9H14 122 107, 91, 65, 41 - 0.03 ± 0.002
14 5.16 3,7-Dimethyl-1,3,6-octatriene C10H16 136 121, 93, 77, 57 - 0.05 ± 0.01
15 5.69 4,5-Diethyloctane C12H26 170 141, 111, 84, 67, 43 0.63 ± 0.02 0.46 ± 0.02
16 5.94 1,2,4,5-Tetramethylbenzene C10H14 134 119, 91, 65 - 0.01 ± 0.001
17 6.01 5,6-Dimethyldecane C12H26 170 141, 113, 84, 67, 43 0.73 ± 0.02 0.18 ± 0.02
18 6.17 4-Ethyldecane C12H26 170 140, 113, 85, 43 0.18 ± 0.01 -
19 6.24 2,6-Dimethyldecane C12H26 170 140, 113, 71, 43 0.29 ± 0.01 -
20 6.68 Dodecane C12H26 170 141, 112, 85, 57, 41 0.14 ± 0.01 -
21 7.05 2-Carene C10H16 136 121, 93, 77 - 0.03 ± 0.003
22 7.22 2,6,10-Trimethyldodecane, C15H32 212 183, 155, 127, 85, 57 - 0.02 ± 0.002
23 7.29 1,2,3,4-Tetrahydro-1,1,6-trimethylnaphthalene C13H18 174 159, 131, 105, 71 - 0.07 ± 0.01
24 7.46 3-Methylnonadecane C20H42 283 253, 169, 141, 113, 85, 57 0.12 ± 0.01 -
25 7.65 2,3-Dihydro-1,1,5,6-tetramethyl-1H-indene C6H7BClNO3 187 159, 128, 91, 71 - 0.26 ± 0.02
26 7.66 Decane C10H22 142 99, 71, 43, 27 0.03 ± 0.004 -
27 8.23 1,1,5-Trimethyl-1, 2-dihydronaphthalene C13H16 172 157, 141, 115, 77 - 0.07 ± 0.01
28 8.28 Megastigma-4,6(Z),8(Z)-triene C13H20 176 161, 133, 105, 77 - 0.04 ± 0.004
29 8.47 Dichloroacetic acid, tetradecyl ester C16H30Cl2O2 325 196, 168, 139, 111, 83, 65, 43 0.07 ± 0.006 -
30 8.47 1-Tetradecene C14H28 196 168, 140, 111, 83 - 0.04 ± 0.003
31 8.53 Tetradecane C14H30 198 169, 141, 113, 85, 57 0.03 ± 0.003 -
32 8.74 Alloaromadendrene C15H24 204 189, 161, 119, 91, 69 - 0.06 ± 0.004
33 8.99 3,8-Dimethyldecane C12H26 170 141, 113, 85, 57 - 0.08 ± 0.01
34 9.04 9-Methylnonadecane C20H42 282 267, 238, 168, 140, 113, 85 - 0.03 ± 0.004
35 9.20 2,6-Bis(1,1-dimethylethyl)-2,5-cyclohexadiene-1,4-dione C14H20O2 220 177, 135, 91, 67 - 0.07 ± 0.01
36 9.51 2,4-Bis(1,1-dimethylethyl)phenol C14H22O 206 191, 163, 115, 91, 57 0.13 ± 0.01 0.13 ± 0.02
37 9.60 1-Butyl-2-propylcyclopentane C12H24 168 140, 111, 91, 69, 41 0.03 ± 0.004 -
38 9.65 4-Ethoxybenzoic acid ethyl ester C11H14O3 194 149, 121, 93, 65 - 0.09 ± 0.01
39 9.87 Dodecanoic acid C12H24O2 200 157, 129, 101, 73, 43 0.54 ± 0.02 2.26 ± 0.09
40 10.15 1-Tricosanol C23H48O 340 322, 294, 154, 125, 97, 69, 43 0.08 ± 0.01 -
41 10.22 Hexadecane C16H34 226 169, 141, 113, 85, 57 0.12 ± 0.02 -
42 11.26 2,6,10,14-Tetramethylpentadecane C19H40 268 253, 183, 141, 113, 85, 57 - 0.20 ± 0.01
43 11.33 Heptadecane C17H36 240 169, 141, 113, 85, 57 0.21 ± 0.01 5.38 ± 0.13
44 11.49 3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol C15H26O 222 204, 161, 136, 93, 69 0.24 ± 0.02 -
45 11.72 Hexacosane C26H54 366 243, 197, 141, 113, 85, 57 - 0.09 ± 0.004
46 11.83 9-Octylheptadecane C25H52 352 239, 197, 169, 141, 113, 85, 57 0.09 ± 0.01 -
47 11.86 Tetradecanoic acid C14H28O2 228 185, 157, 129, 97, 73 0.44 ± 0.02 0.92 ± 0.02
48 12.08 Benzyl benzoate C14H12O2 212 167, 105, 77, 51 - 0.27 ± 0.01
49 12.23 6-Tetradecanesulfonic acid butyl ester C18H38O3S 334 196, 127, 91, 71, 52 - 0.08 ± 0.01
50 12.28 3,3,4-Trimethyl-4-p-tolylcyclopentanol C15H22O 218 200, 163, 147, 119, 91 0.20 ± 0.01 -
51 12.50 2,6,10,14-Tetramethylhexadecane C20H42 282 253, 183, 141, 113, 85 0.18 ± 0.01 -
52 13.06 2-Methylheptadecane C18H38 254 239, 211, 141, 113, 85, 57 - 0.11 ± 0.01
53 13.25 Cyclohexadecane C16H32 224 125, 55 - 0.16 ± 0.02
54 13.40 1,2-Benzenedicarboxylic acid bis(2-methylpropyl) ester C16H22O4 278 223, 167, 149, 104, 76, 57 0.44 ± 0.03 0.28 ± 0.01
55 13.49 Cyclopentadecane C15H30 210 182, 139, 111, 83, 55 0.07 ± 0.001 -
56 13.63 2-Methylhexacosane C27H56 380 365, 337, 169, 141, 113, 85 - 0.10 ± 0.01
57 13.68 Hentriacontane C31H64 436 169, 141, 113, 85, 57 - 0.14 ± 0.01
58 13.69 8-Heptadecene C17H34 238 210, 140, 111, 83, 55 0.08 ± 0.001 -
59 14.21 2,3-Dimethylnonadecane C21H44 297 253, 183, 155, 127, 99, 71 0.19 ± 0.01 -
60 14.53 Palmitoleic acid C16H30O2 254 236, 192, 137, 111, 83 0.77 ± 0.02 -
61 14.57 Oxacycloheptadecan-2-one C16H30O2 254 236, 194, 138, 111, 83 0.39 ± 0.01 -
62 14.87 n-Hexadecanoic acid a C16H32O2 256 213, 185, 157, 129, 83, 60 16.06 ± 0.25 20.86 ± 0.31
63 15.64 1-Heptacosanol C27H56O 396 378, 181, 153, 125, 97, 57 0.29 ± 0.02 -
64 16.06 3,7,11,15-Tetramethylhexadeca-1,3,6,10,14-pentaene C20H32 272 229, 191, 119, 93, 69 0.65 ± 0.01 -
65 16.07 3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol C15H26O 222 191, 161, 137, 93, 69 - 0.70 ± 0.01
66 16.12 Trispiro[4.2.4.2.4.2.]heneicosane C21H44 296 288, 231, 192, 163, 135, 97 0.29 ± 0.01 -
67 16.47 N-[4-bromo-n-butyl]-2-piperidinone C9H16BrNO 234 205, 154, 97, 43 - 0.10 ± 0.01
68 16.73 2,2-Dimethyl-5-(3-methyloxiranyl)-cyclohexanone C11H20O2 196 182, 153, 123, 95, 69, 41 0.11 ± 0.008 -
69 16.74 7-Bromomethylpentadec-7-ene C16H31Br 302 223, 153, 125, 97, 69 - 0.15 ± 0.01
70 17.03 1-Nonadecene C19H38 266 266, 210, 168, 126, 97 0.31 ± 0.01 0.10 ± 0.01
71 17.04 8-Hexadecene C16H32 224 196, 153, 125, 97, 69 - 0.60 ± 0.02
72 17.21 Estra-1,3,5(10)-trien-17β-ol C18H24O 256 185, 157, 129, 97, 73 - 0.11 ± 0.01
73 17.23 Nonadecyl pentafluoropropionate C22H39F5O2 430 313, 266, 153, 125, 97, 57 0.03 ± 0.001 -
74 17.36 Heneicosane C21H44 296 197, 169, 141, 113, 85 0.63 ± 0.02 0.51 ± 0.02
75 17.64 6-Octen-1-ol, 3,7-dimethyl acetate C12H22O2 198 156, 123, 103, 81 2.33 ± 0.15 -
76 17.94 Trifluoroacetic acid pentadecyl ester C18H31F3O2 336 306, 255, 182, 140, 111, 83 - 0.42 ± 0.02
77 18.09 9,12-Octadecadienoic acid a C18H32O2 280 236, 150, 123, 95, 67 2.92 ± 0.09 0.59 ± 0.01
78 18.21 9,12,15-Octadecatrien-1-ol C18H32O 264 236, 208, 108, 79 6.66 ± 0.14 -
79 18.40 9,12,15-Octadecatrienoic acid a C18H30O2 278 222, 163, 135, 108, 79 - 9.06 ± 0.17
80 18.66 4-(4-Ethylcyclohexyl)-1-pentylcyclohexene C19H34 262 220, 191, 164, 123, 81 0.42 ± 0.01 -
81 18.66 Methyl 6,9,12-hexadecatrienoate C17H28O2 264 194, 175, 135, 107, 79 - 0.69 ± 0.02
82 18.80 9-Octadecenoic acid a C18H34O2 282 264, 222, 165, 137, 111, 83 0.43 ± 0.01 0.14 ± 0.01
83 18.83 1-Eicosene C20H40 280 252, 182, 153, 125, 97 0.53 ± 0.02 0.10 ± 0.01
84 18.84 tert-Hexadecanethiol C16H34S 258 224, 165, 111, 57 - 0.74 ± 0.01
85 18.97 Bacchotricuneatin C C20H22O5 342 245, 191, 145, 112, 71 - 0.14 ± 0.01
86 19.01 E-8-Methyl-7-dodecen-1-ol acetate C15H28O2 240 197, 165, 126, 97, 69 0.08 ± 0.003 -
87 19.01 3-Methylheptadecane C18H38 254 225, 169, 141, 113, 85, 57 - 0.12 ± 0.01
88 19.03 1-Chloro-octadecane C18H37Cl 288 175, 147, 113, 85, 57 - 0.50 ± 0.01
89 19.15 2-Dodecen-1-yl(-)succinic anhydride C16H26O3 266 237, 299, 181, 149, 123, 97, 69, 41 0.07 ± 0.001 0.10 ± 0.01
90 19.21 1-(1,5-Dimethylhexyl)-4-(4-methylpentyl)cyclohexane C20H40 280 191, 166, 123, 97, 69 0.05 ± 0.001 0.27 ± 0.01
91 19.68 9-Tricosene C23H46 322 294, 167, 139, 111, 83 0.95 ± 0.03 0.89 ± 0.02
92 19.83 13-Tetradecen-1-ol acetate C16H30O2 254 194, 167, 139, 111, 83 0.13 ± 0.01 -
93 20.55 1-Tricosene C23H46 322 196, 169, 139, 111, 83, 57 0.05 ± 0.001 -
94 20.92 1,7,11-Trimethyl-4-(1-methylethyl)cyclotetradecane C20H40 280 236, 204, 165, 125, 97 0.10 ± 0.01 0.12 ± 0.01
95 21.03 1-Docosene C23H46 308 223, 181, 139, 97, 57 0.33 ± 0.01 0.18 ± 0.01
96 21.34 Eicosyl pentafluoropropionate C23H41F5O2 444 426, 280, 182, 153, 125, 97 0.09 ± 0.005 0.16 ± 0.01
97 21.66 Eicosane C20H42 282 197, 169, 141, 113, 85 1.10 ± 0.04 2.28 ± 0.10
98 21.91 Docosane C22H46 310 197, 169, 141, 113, 85 0.04 ± 0.003 0.37 ± 0.01
99 22.05 Nonadecane C19H40 268 197, 169, 141, 113, 85 0.68 ± 0.01 -
100 22.06 Octatriacontyl trifluoroacetate C40H77F3O2 646 181, 139, 97, 57 - 0.46 ± 0.01
101 22.61 Behenyl chloride C22H45Cl 344 189, 169, 141, 113, 85 0.44 ± 0.01 0.05 ± 0.004
102 22.72 11,13-Dimethyl-12-tetradecen-1-ol acetate C18H34O2 282 267, 208, 151, 123, 95, 69 0.10 ± 0.02 0.69 ± 0.02
103 22.72 15-Isobutyl-(13αH)-isocopalane C24H44 332 276, 219, 191, 151, 123, 95 - 0.41 ± 0.01
104 24.21 Cyclotetracosane C24H48 336 308, 167, 139, 111, 83 0.41 ± 0.01 0.49 ± 0.01
105 24.32 2,2'-Methylenebis[6-(1,1-dimethylethyl)-4-methyl]phenol C23H32O2 340 284, 177, 149, 121, 91 2.78 ± 0.09 2.51 ± 0.07
106 24.59 Hexadecyloxirane C18H36O 268 250, 211, 166, 138, 111, 82 0.71 ± 0.03 -
107 25.48 Dotriacontyl pentafluoropropionate C35H65F5O2 612 594, 448, 181, 139, 97, 57 0.08 ± 0.002 0.13 ± 0.01
108 26.38 Tetratriacontane C34H70 478 253, 225, 197, 169, 141, 113, 85 - 0.39 ± 0.02
109 26.66 12-Pentacosene C25H50 350 350, 181, 153, 125, 97, 69 0.20 ± 0.01 -
110 27.32 Bis(2-ethylhexyl)phthalate C24H38O4 390 279, 180, 149, 104, 57 1.60 ± 0.06 -
111 27.95 Eicosyl trifluoroacetate C22H41F3O2 394 376, 325, 280, 153, 125, 97 0.06 ± 0.002 -
112 28.50 Heptacosyl trifluoroacetate C29H55F3O2 492 474, 423, 378, 181, 139, 97 0.09 ± 0.01 -
113 28.58 Hexacosane C26H54 366 169, 141, 113, 85, 57 1.11 ± 0.05 1.20 ± 0.06
114 29.31 2-Dodecen-1-yl(-)succinic anhydride C16H26O3 266 209, 166, 137, 97, 69 1.65 ± 0.06 0.08 ± 0.002
115 29.53 Tricosane C23H48 324 197, 169, 141, 113, 85 0.13 ± 0.01 0.53 ± 0.02
116 29.88 Pentacosane C25H52 352 211, 169, 141, 113, 85, 57 - 1.56 ± 0.05
117 29.89 2,6,10,14,18-Pentamethyleicosane C25H52 352 253, 183, 141, 113, 85 1.15 ± 0.04 -
118 30.64 2,6,10,14-Tetramethyl-7-(3-methylpent-4-enylidene)pentadecane C25H48 348 264, 207, 167, 125, 97 0.56 ± 0.02 -
119 30.67 14-Nonacosane C29H60 408 378, 181, 153, 125, 97 0.25 ± 0.01 0.10 ± 0.03
120 30.87 Octadecane C18H38 254 169, 141, 113, 85, 57 8.16 ± 0.14 5.70 ± 0.09
121 31.05 1-Hexacosene C26H52 364 209 ,181, 153, 125, 97 0.46 ± 0.01 0.54 ± 0.02
122 31.59 1-Bromo-11-iodoundecane C11H22BrI 362 281, 233, 177, 135, 97 0.31 ± 0.01 0.27 ± 0.01
123 31.62 1-Methyl-4-(1-methylethyl)-3-[1-methyl-1-(4-methylpentyl)-5-methylheptyl]cyclohexene C25H48 348 248, 193, 123, 69 0.24 ± 0.01 -
124 32.46 13-Methyl-Z-14-nonacosene C30H60 420 405, 209, 181, 153, 125, 97 0.78 ± 0.02 -
125 32.98 (5α,14β)-Cholestane C27H48 372 259, 218, 176, 149, 109 2.11 ± 0.03 1.66 ± 0.09
126 33.10 Tetracosane C24H50 338 169, 141, 113, 85, 57 3.24 ± 0.05 1.00 ± 0.07
127 33.67 Cholestane C27H48 372 262, 217, 149, 109, 81 5.24 ± 0.09 3.93 ± 0.10
128 34.33 (5α,13α)-d-Homoandrostane C20H34 274 259, 217, 177, 149, 95, 55 1.25 ± 0.04 1.39 ± 0.06
129 35.31 Nonacosane C29H60 408 197, 169, 141, 113, 85 6.44 ± 0.21 5.07 ± 0.19
130 35.94 Stigmastane C29H52 400 290, 217, 189, 149, 109 4.44 ± 0.18 3.27 ± 0.14
131 37.45 1-Iodo-octadecane C18H37I 380 253, 183, 141, 99, 57 2.16 ± 0.08 0.67 ± 0.03
132 37.46 Triacontane C30H62 422 197, 169, 141, 113, 85, 57 - 2.88 ± 0.11
133 37.80 28-Nor-17α(H)-hopane C29H50 398 383, 355, 218, 191, 137, 109 2.44 ± 0.09 -
134 43.31 β-Sitosterol C29H50O 414 381, 329, 255, 213, 145, 81 4.60 ± 0.17 2.36 ± 0.09
135 43.70 (3β,24Z)-Stigmasta-5,24(28)-dien-3-ol C29H48O 412 379, 314, 281, 229, 202 - 2.04 ± 0.10

a Compounds were confirmed by the reference standards. RR: R. roxburghii; RS: R. sterilis.