TABLE 1.
GC-MS data for the metabolitesa formed from n-alkylcyclohexanes and n-alkylbenzenes by Alcanivorax sp. strain MBIC 4326
| Compound sourceb and metabolite no. | Amt (μmol)c | Retention time (min) | m/z of major ion peaks (%)d | Suggested structuree |
|---|---|---|---|---|
| n-Octadecylcyclohexane | 51 | 8.9 | 142 (M+) (30), 127 (9), 113 (22), 111 (20), 110 (26), 101 (16), 100 (7), 88 (8), 87 (100), 84 (5), 83 (73), 82 (31), 81 (18), 79 (6), 75 (9), 74 (55), 69 (17), 68 (28) | Methyl cyclohexanecarboxylate |
| 83 | 11.2 | 156 (M+) (2), 125 (20), 113 (5), 97 (13), 83 (9), 82 (11), 81 (17), 79 (7), 76 (7), 75 (68), 74 (100), 68 (5) | Methyl cyclohexaneacetate | |
| 3.1 | 10.8 | 140 (M+) (31), 109 (22), 108 (24), 82 (8), 81 (100), 80 (73), 79 (64), 77 (16), 67 (5) | Methyl 1-cyclohexene-1-carboxylate | |
| 0.02 | 9.7 | 136 (M+) (58), 135 (6), 106 (14), 105 (100), 92 (6), 78 (9), 77 (81), 75 (4), 74 (6) | Methyl benzoate | |
| n-Nonadecylcyclohexane | 86 | 8.9 | Same as the results described above | Methyl cyclohexanecarboxylate |
| 42 | 11.2 | Same as the results described above | Methyl cyclohexaneacetate | |
| 4.7 | 10.8 | Same as the results described above | Methyl 1-cyclohexene-1-carboxylate | |
| 1.1 | 9.7 | Same as the results described above | Methyl benzoate | |
| n-Undecylbenzene | 190 | 9.7 | Same as the results described above | Methyl benzoate |
| 4.6 | 11.9 | 150 (M+) (71), 119 (6), 118 (5), 92 (22), 91 (100), 89 (14), 65 (41), 64 (5) | Phenylacetic acid, methyl ester | |
| 0.9 | 14.2 | 164 (M+) (24), 133 (8), 107 (4), 105 (33), 104 (100), 103 (13), 92 (5), 91 (69), 79 (12), 78 (13), 77 (18), 65 (12) | 3-Phenylpropanoic acid, methyl ester | |
| 5.0 | 16.7 | 162 (M+) (43), 161 (24), 132 (9), 131 (100), 104 (7), 103 (60), 102 (14), 78 (4), 77 (40), 76 (7), 75 (4), 74 (4), 65 (4) | trans-Cinnamic acid, methyl ester | |
| n-Hexadecylbenzene | ||||
| 4 | 14 | 9.7 | Same as the results described above | |
| 5 | 130 | 11.8 | Same as the results described above | |
| 6 | 0.7 | 14.2 | Same as the results described above | |
| 7 | 0.4 | 16.7 | Same as the results described above | |
| 8 | 3.2 | 16.8 | 178 (M+) (16), 162 (7), 161 (5), 147 (21), 146 (25), 131 (17), 117 (5), 115 (5), 105 (30), 104 (100), 103 (17), 92 (6), 91 (64), 89 (4), 78 (8), 77 (15), 75 (5), 74 (68), 65 (23) | 4-Phenylbutanoic acid, methyl ester |
| 9 | 0.8 | 17.2 | 176 (M+) (28), 145 (5), 134 (9), 118 (9), 117 (100), 116 (13), 115 (51), 91 (17), 65 (7) | 4-Phenyl-2-butenoic acid, methyl esterf |
| 10 | 9.4 | 18.6 | 176 (M+) (32), 161 (4), 144 (5), 134 (10), 118 (11), 117 (100), 116 (14), 115 (49), 91 (17), 89 (4), 65 (6) | 4-Phenyl-3-butenoic acid, methyl ester |
Analyses were performed after methylation with trifluoro boron-methanol.
Substrate concentration was as follows: 1 g/liter in 50 ml of medium contains 149, 143, 215, and 165 μmol of n-octadecylcyclohexane, n-nonadecylcyclohexane, n-undecylbenzene, and n-hexadecylbenzene, respectively.
Based on the total ion current response of the mass-selective detector relative to the authentic standards.
The ion abundance percentages are shown in parentheses.
Identification was based on the match of mass spectra (fragmentation and peak intensity) and capillary GC retention times with data for authentic samples, except for data described in footnote f, which indicated a fragmentation match higher than 85%.
High degree of match to the library (NIST and WILEY installed in Shimadzu GCMS-QP5050A9).