Table 1.

GC-MS data for products formed from methylnaphthalenes byS. paucimobilis 2322 grown on 2,6-DMNa

Product (compound)Relative amt (%)bGCRt (min)m/z of major ion peaks (%)Suggested structure
From 2,6-DMN
 127.511.34166 (M+) (34), 135 (21), 134 (100), 106 (23), 105 (11), 78 (17), 77 (18)5-Methylsalicylic acid methyl esterc , d
 23.216.24172 (M+) (100), 157 (23), 143 (11), 141 (8), 129 (32), 128 (29), 115 (10)2-Hydroxymethyl-6-methylnaphthalenee
 350.017.37200 (M+) (71), 185 (2), 169 (100), 155 (2), 141 (53), 139 (16), 115 (27)6-Methyl-2-naphthoic acid methyl esterd
 48.518.01216 (M+) (100), 201 (15), 187 (10), 186 (20), 173 (29), 158 (7), 145 (13), 129 (17), 119 (17), 115 (39)6-Hydroxymethyl-2-naphthoic acid methyl estere
 50.518.58234 (M+) (12), 216 (29), 200 (68), 184 (27), 175 (29), 169 (100), 157 (87), 141 (60), 129 (47), 115 (52)1,2-Dihydroxy-1-hydro-6-methyl-2-naphthoic acid methyl estere
 60.520.71244 (M+) (70), 213 (100), 185 (47), 170 (13), 169 (17), 154 (23), 126 (39), 115 (24)Naphthalene-2,6-dicarboxylic acid dimethyl esterd
From 2,7-DMN
 736.111.34166 (M+) (34.5), 134 (100), 106 (26), 105 (20), 78 (19), 77 (18)4-Methylsalicylic acid methyl esterc , d
 81.016.18172 (M+) (100), 157 (33), 143 (22), 141 (38), 129 (64), 128 (50), 115 (25)2-Hydroxymethyl-7-methylnaphthalenee
 957.717.28200 (M+) (75), 185 (1), 169 (100), 155 (2), 141 (60), 115 (27)7-Methyl-2-naphthoic acid methyl estere
 102.218.54234 (M+) (12), 216 (26), 200 (71), 184 (26), 175 (32), 169 (100), 157 (82), 141 (67), 129 (46), 115 (52)1,2-Dihydroxy-1-hydro-7-methyl-2-naphthoic acid methyl estere
From 2,3-DMN
 1190.913.38180 (M+) (34), 165 (1), 149 (21), 148 (100), 141 (2), 120 (22), 105 (3), 91 (28)4,5-Dimethylsalicylic acid methyl esterc , d
 124.217.30200 (M+) (72), 185 (1), 169 (100), 155 (3), 141 (56), 138 (18), 115 (27)3-Methyl-2-naphthoic acid methyl esterc , d
From 1,5-DMN
 1326.011.47166 (M+) (35), 135 (24), 134 (100), 106 (31), 105 (22), 78 (18), 77 (17)6-Methylsalicylic acid methyl esterc , d
 1444.017.32200 (M+) (74), 185 (3), 169 (100), 155 (2), 141 (58), 115 (32.7)5-Methyl-1-naphthoic acid methyl esterc
From 1,6-DMN
 1540.011.30166 (M+) (35), 134 (100), 106 (27), 105 (21), 94 (7), 78 (27), 77 (20)5-Methylsalicylic acid methyl esterc , d
 1640.011.45166 (M+) (46), 134 (100), 106 (40), 105 (34), 94 (26), 78 (35), 77 (44)6-Methylsalicylic acid methyl esterc , d
 1710.817.29200 (M+) (74), 185 (2), 169 (100), 155 (9), 141 (73), 128 (5), 115 (37)5(6)-Methyl-2(1)-naphthoic acid methyl estere
From 1,8-DMN
 182.011.05166 (M+) (41), 141 (15), 134 (100), 115 (14), 106 (65), 94 (35), 78 (40), 77 (31)3-Methylsalicylic acid methyl esterc , d
 1967.015.67170 (M+) (75), 155 (3), 142 (52), 141 (100), 139 (21), 115 (35), 84 (10)8-Methyl-1-naphthaldehydec
 203.016.79172 (M+) (41), 154 (73), 153 (100), 143 (13), 141 (21), 128 (30), 115 (22)1-Hydroxymethyl-8-methylnaphthalenee
 211.919.18184 (M+) (80), 155 (100), 139 (11), 127 (88), 101 (6), 77 (12)1,8-Naphthalided
From 1,2-DMN
 2270.813.12180 (M+) (38), 149 (22), 148 (100), 120 (76), 105 (8), 91 (29)3,4-Dimethylsalicylic acid methyl esterc , d
 231.416.32172 (M+) (95.7), 157 (45), 154 (74), 143 (74), 141 (78), 129 (100), 128 (85), 115 (57)2(1)-Hydroxymethyl-1(2)-methylnaphthalenee
From 1,4-DMN
 244.212.74180 (M+) (42), 165 (2), 155 (12), 149 (24), 148 (85), 120 (100), 105 (8), 91 (38)3,6-Dimethylsalicylic acid methyl esterc , d
 2594.017.37200 (M+) (61), 185 (2), 169 (100), 141 (48), 115 (28)4-Methyl-1-naphthoic acid methyl esterc
From 2,3,6-trimethylnaphthalene
 2632.413.36180 (M+) (33), 165 (1), 149 (21), 148 (100), 120 (23), 105 (3), 91 (29)4,5-Dimethylsalicylic acid methyl esterc , d
 2713.018.22214 (M+) (95), 199 (8), 183 (68), 182 (70), 155 (66), 154 (100), 139 (15), 128 (26), 115 (12)3,6-Dimethyl-2-naphthoic acid methyl estere
 2830.019.07214 (M+) (85), 199 (3), 183 (100), 169 (2.1), 155 (46), 139 (9), 128 (9), 115 (8)6,7-Dimethyl-2-naphthoic acid methyl estere
From 2-methylnaphthalene
 291.69.47152 (M+) (46), 121 (37), 120 (100), 93 (14), 92 (49), 65 (24)Salicylic acid methyl esterc , d
 302.511.23166 (M+) (35), 134 (100), 106 (28), 105 (24), 78 (20), 77 (19)4-Methylsalicylic acid methyl esterc , d
 310.313.23194 (M+) (8), 163 (100), 149 (6), 135 (8), 115 (18), 109 (20), 77 (31)Phthalic acid dimethyl esterc , d
 325.815.77186 (M+) (57), 155 (100), 137 (11), 127 (85), 126 (14), 115 (8)2-Naphthoic acid methyl esterc , d
 337.516.98202 (M+) (28), 171 (18), 170 (100), 142 (7), 115 (19), 114 (55)1-Hydroxy-2-naphthoic acid methyl esterc , d
 3458.017.31220 (M+) (9), 202 (27), 186 (2), 170 (7), 161 (37), 155 (3), 143 (100), 131 (27), 115 (95)1,2-Dihydroxy-1-hydro-2-naphthoic acid methyl estere
  • a Analyses were performed after methylation with diazomethane.

  • b Based on the total ion current response of the mass-selective detector.

  • c Identification was based on an instrument library match.

  • d Identification was based on a match of mass spectra (fragmentation and peak intensity) and capillary GC retention times with data for authentic samples.

  • e Tentative assignment of structure.