Atlas of Mass Spectra

________________________________________
Atlas of Mass Spectra
In this Atlas are presented the mass spectra of compounds that have been discussed in
the previous chapters. Identification of these compounds was done through synthesis
of model compounds, comparison of the fragmentation patterns observed in the mass
spectra of several derivatives, and comparison of the mass spectra with reference
spectra from literature and from the Wiley library of MassLib version 7.3 (see
previous chapters and literature cited therein).
The mass spectra were obtained with the JEOL-DX303 GCMS instrument at FOM
Institute AMOLF (see Materials and methods sections in the previous Chapters)
under electron ionisation conditions (70 eV). Spectra were transferred from the JEOL
data system, and processed in TopDraw 3.0. Structures were drawn with ACD
Chemsketch 2.0.
Index of spectra by Molecular Weight
MW Atlas MW Atlas MW Atlas

204 51 316 31 348 26
204 52 316 36 354 17
204 53 316 48 356 8
204 54 316 49 358 13
204 55 316 50 360 38
204 56 316 64 362 45
204 57 316 66 364 44
204 58 318 37 372 4
204 59 318 42 372 12
204 60 320 39 374 2
204 61 320 41 374 24
204 62 322 40 376 47
204 63 326 15 386 6
236 69 328 5 386 14
248 70 330 18 388 34
250 71 330 32 402 19
272 35 330 43 416 10
272 68 334 29 420 28
302 65 334 46 450 27
302 67 340 16 460 20
306 25 342 7 474 11
314 3 344 9 490 22
316 1 344 21 548 23
316 30 346 33
A2 Atlas of Mass Spectra
Alphabetical index of spectra
(-)-16-kaurene (k1) 35
3-acetoxy-copaiferic acid, methyl ester (L11) 47
3-hydroxy-copaiferic acid, methyl ester (L10) 46
7,15-dihydroxy-DHA, dimethyl ether, methyl ester 24
7,15-dihydroxy-DHA, di-TMS ether, methyl ester 22
7,15-dihydroxy-DHA, di-TMS ether, TMS ester 23
7-oxo-DHA, dimethylated derivative 7
7-oxo-DHA, methyl ester 5
7-oxo-DHA, TMS ester 6
7-oxo-DHA, trimethylated derivative 8
15-hydroxy-7-oxo-DHA, dimethylated derivative 13
15-hydroxy-7-oxo-DHA, dimethylated derivative (dehydrogenated) 16
15-hydroxy-7-oxo-DHA, methyl ester 9
15-hydroxy-7-oxo-DHA, methyl ester (dehydrogenated) 15
15-hydroxy-7-oxo-DHA, tetramethylated derivative 14
15-hydroxy-7-oxo-DHA, TMS ether, methyl ester 10
15-hydroxy-7-oxo-DHA, TMS ether, TMS ester 11
15-hydroxy-7-oxo-DHA, trimethylated derivative 12
15-hydroxy-7-oxo-DHA, trimethylated derivative (dehydrogenated) 17
15-hydroxy-DHA, methyl ester 18
15-hydroxy-DHA, methyl ether, methyl ester 21
15-hydroxy-DHA, TMS ether, methyl ester 19
15-hydroxy-DHA, TMS ether, TMS ester 20
16ß-kauran-19-oic acid, methyl ester (k3) 37
α-bergamotene (S7) 57
α-copaene (S3) 53
α-cubebene (S2) 52
α-humulene (S8) 58
α-selinene (S10) 60
ß-bisabolene (S11) 61
ß-elemene (S4) 54
γ-cadinene (S9) 59
γ-elemene (S13) 63
δ-cadinene (S12) 62
δ-elemene (S1) 51
Abietic acid, methyl ester 1
Abietic acid, TMS ester 2
Acetoxy-Hardwickiic acid, methyl ester (c3) 34
Agathic acid, dimethyl ester (L9) 45
Atlas of Mass Spectra A3
Cativic acid, methyl ester (L3) 41

Communic acid, methyl ester 64
Communol, methyl ether 65
Copalic acid, methyl ester (L5) 42
Cyperene (S5) 55
Dehydroabietic acid (DHA), methyl ester 3
Dehydroabietic acid (DHA), TMS ester 4
enantio-biformene 68
Eperuic acid, methyl ester (L1) 39
Hardwickiic acid, methyl ester (c1) 32
Hydroxy-Hardwickiic acid, methyl ester (c2) 33
Isopimaric acid, methyl ester (P3) 50
Kaur-16-en-19-oic acid, methyl ester (k2) 36
Labdanic acid, methyl ester (L2) 40
Larixol 25
Larixol, dimethyl ether 29
Larixol, di-TMS ether 27
Larixyl acetate 26
Larixyl acetate, TMS ether 28
Neoabietic acid, methyl ester (a4) 31
Ozic acid, methyl ester 66
Ozol, methyl ether 67
Palustric acid, methyl ester (a1) 30
Pimaric acid, methyl ester (P1) 48
Pinifolic acid, dimethyl ester (L8) 44
Polyalthic acid, methyl ester (L6) 43
Pyrolysis product of polycommunic acid, methyl ester 69
Sandaracopimaric acid, methyl ester (P2) 49
Trans-caryphyllene (S6) 56
Unidentified kaurane (k4) 38
100
316
256
50
241
COOMe
213
121
136
105 185 273
91
79 157 301
199
0
100 200 300 400 m/z
1 MW=316 Abietic acid, methyl ester
100
256
50
241 COOTMS
374
73 185 213 359
131
91 105 172
0
100 200 300 400 m/z
2 MW=374 Abietic acid, TMS ester
100
239
50
299 COOMe
314
197
141 173 255
211
0
100 200 300 400 m/z
3 MW=314 Dehydroabietic acid (DHA), methyl ester
100
239
50
COOTMS
357 372
73 131
143 255
171 197 225
0
100 200 300 400 m/z
4 MW=372 Dehydroabietic acid (DHA), TMS ester
100
253
328
50
O
COOMe
187 269
171 213 296
129 313
0
100 200 300 400 m/z
5 MW=328 7-oxo-DHA, methyl ester
100
253 268
386
50
O 327
COOTMS
73 187 371
178 213 342
0
100 200 300 400 m/z
6 MW=386 7-oxo-DHA, TMS ester
100
342
50 267
OMe
227
COOMe 283
126 187 216 327

251
0
100 200 300 400 m/z
7 MW=342 7-oxo-DHA, dimethylated derivative
100
356
281
50
OMe
COOMe
230 265 341
297
241
201
141
0
100 200 300 400 m/z
8 MW=356 7-oxo-DHA, trimethylated derivative
100
329
OH
50
O
COOMe
269
187 203 344
227 253 285 313
0
100 200 300 400 m/z
9 MW=344 15-hydroxy-7-oxo-DHA, methyl ester
100
OTMS 401
50
O
COOMe
267
73 286 326 385
131 251 341 357
0
100 200 300 400 m/z
10 MW=416 15-hydroxy-7-oxo-DHA, TMS ether, methyl ester
100
459
OTMS
50
COOTMS
73 327 357 369

285 341 443
131 231 251 474
0
100 200 300 400 m/z
11 MW=474 15-hydroxy-7-oxo-DHA, TMS ether, TMS ester
100 OMe
372
340
297
OMe
50 313
357
73 COOMe 341
141
246
257
213 325
121 281
171 265
165
0
100 200 300 400 m/z
12 MW=372 15-hydroxy-7-oxo-DHA, trimethylated derivative
100 358
OH
283 340
299
50
OMe
243
COOMe 265
134
225
43 213
59 185
0
100 200 300 400 m/z
13 MW=358 15-hydroxy-7-oxo-DHA, dimethylated derivative
100 386
OMe
73
50 311
OMe
371
COOMe
260 327 339
231 354
148 211
128 271 295
227
121 178
0
100 200 300 400 m/z
14 MW=386 15-hydroxy-7-oxo-DHA, tetramethylated derivative
100 251
326
50
O
COOMe
185 211 267 294

115 225
0
100 200 300 400 m/z
15 MW=326 15-hydroxy-7-oxo-DHA, methyl ester (dehydrogenated)
100 340
265
50 225
OMe
COOMe
281
214
249
185
165 293 325
0
100 200 300 400 m/z
16 MW=340 15-hydroxy-7-oxo-DHA, dimethylated derivative
(dehydrogenated)
100 354
279
50
OMe
COOMe 225
339
199 295
265
155 307
0
100 200 300 400 m/z
17 MW=354 15-hydroxy-7-oxo-DHA, trimethylated derivative
(dehydrogenated)
100 315
OH
255
50
COOMe
237
330
253 312
271
59 297
0
100 200 300 400 m/z
18 MW=330 15-hydroxy-DHA, methyl ester
100 OTMS
237
387
50
75 COOMe
312
131 297 343 371

253 327 402
0
100 200 300 400 m/z
19 MW=402 15-hydroxy-DHA, TMS ether, methyl ester
100 OTMS 445
50
COOTMS
370
253 355
131 237 327 460
0
100 200 300 400 m/z
20 MW=460 15-hydroxy-DHA, TMS ether, TMS ester
100
OMe 329
50
COOMe
269 297 313

344
73 237
253 285
0
100 200 300 400 m/z
21 MW=344 15-hydroxy-DHA, methyl ether, methyl ester
100
OTMS 475
50
OTMS
COOMe
400 431
131 251 325 341 385 415 490
0
100 200 300 400 m/z
22 MW=490 7,15-dihydroxy-DHA, di-TMS ether, methyl ester
100
OTMS 533
50
OTMS
COOTMS
73
445
325 381 458
131 548
0
100 200 300 400 500 m/z
23 MW=548 7,15-dihydroxy-DHA, di-TMS ether, TMS ester
100
359
OMe
50
OMe
COOMe
342
267 327 343
73 335
253 283 328 374
0
100 200 300 400 m/z
24 MW=374 7,15-dihydroxy-DHA, dimethyl ether, methyl ester
100 OH
71
270
109
153 255
50
189
288
291 OH
306
0
100 200 300 400 m/z
25 MW=306 Larixol
100 153 255

OH
270
50
195
71
288
273
OAc
333
0
100 200 300 400 m/z
26 MW=348 Larixyl acetate
100
143 225 OTMS
50 73
270
255
345 OTMS
360
435
0
100 200 300 400 m/z
27 MW=450 Larixol, di-TMS ether
100 143 OTMS
50
270
195 255 OAc

153
119
345 360 405
0
100 200 300 400 m/z
28 MW=420 Larixyl acetate, TMS ether
100 85 167
OMe
50 270
255
302
287
OMe
319 334
0
100 200 300 400 m/z
29 MW=334 Larixol, dimethyl ether
100 316
241
301
257
50
105 119
91 187
148 COOMe
149
287
0
100 200 300 400 m/z
30 MW=316 Palustric acid, methyl ester (a1)
100
135
316
50
COOMe
148
121
181 203
235 257
0
100 200 300 400 m/z
31 MW=316 Neoabietic acid, methyl ester (a4)
100
139
203 235 O
96
50
81
COOMe
151 330
175 283
165 299
219
271 315
0
100 200 300 400 m/z
32 MW=330 Hardwickiic acid, methyl ester (c1)
100
249
50 107 219
81 233 OH
139
96 COOMe 346
173 201
163 299
328
0
100 200 300 400 m/z
33 MW=346 Hydroxy-Hardwickiic acid, methyl ester (c2)
100 328
233
219
81 O
95 201
139 O
COOMe
43 O
50
173
107
149
249
281 313 357
341
388
0
100 200 300 400 m/z
34 MW=388 Acetoxy-Hardwickiic acid, methyl ester (c3)
100 257 272
229
50 125
69 147
91 105
41 81
213
55 187
161
175
201
244
0
100 200 300 400 m/z
35 MW=272 (-)-16-kaurene (k1)
100 257
316
273
241
50 121
91 301
105
COOMe
81 131
213
148 187
0
100 200 300 400 m/z
36 MW=316 Kaur-16-en-19-oic acid, methyl ester (k2)
100
259
COOMe
123
50 318
109
81
149
243 286
189 303
168
215
0
100 200 300 400 m/z
37 MW=318 16ß-kauran-19-oic acid, methyl ester (k3)
100 303 360

354
279 345
50
123
91 109 328
225
168
180
0
100 200 300 400 m/z
38 MW=360 Unidentified kaurane (k4) NB: not pure; e.g. m/z 354 and 279
probably derive from a co-eluting oxidised dehydroacbietic acid with M = 354
100 191
95
COOMe
137
50
305
107
123 177 320
81 277
149163 238 289

223 264
0
100 200 300 400 m/z
39 MW=320 Eperuic acid, methyl ester (L1)
100 123
COOMe
50
307 322
69
95 109
81
138
266
166 209
237 291
0
100 200 300 400 m/z
40 MW=322 Labdanic acid, methyl ester (L2)
100 122
191
109
196
COOMe
50
305
95
320
69
136 164 289
149
264
235
0
100 200 300 400 m/z
41 MW=320 Cativic acid, methyl ester (L3)
100 114
137
COOMe
303
81
95
50 69 123
199 177 205

244 318
189
258 271 287
0
100 200 300 400 m/z
42 MW=318 Copalic acid, methyl ester (L5)
100
121
330
50
81 COOMe
189
149
271
181 199
255 315
298
0
100 200 300 400 m/z
43 MW=330 Polyalthic acid, methyl ester (L6)
100
121
COOMe
50
304
COOMe 305
81 109 161 181

235 364
289
175
257 273 333 349
0
100 200 300 400 m/z
44 MW=364 Pinifolic acid, dimethyl ester (L8)
100
121
COOMe
50 COOMe
189
81
114
249 288 302 347
161 181 243
271 330 362
315
0
100 200 300 400 m/z
45 MW=362 Agathic acid, dimethyl ester (L9)
100 135
114
COOMe
50 HO
107
81
121
203
319
260 301
147 175 316
189 285 334
241
0
100 200 300 400 m/z
46 MW=334 3-hydroxy-copaiferic acid, methyl ester (L10)
100 135
O COOMe
50 O
107 203 301

114
302
316
175
147
159 241 273
361 376
345
0
100 200 300 400 m/z
47 MW=376 3-acetoxy-copaiferic acid, methyl ester (L11)
100 121
50
COOMe
316
180
257
181
301
148
241
0
100 200 300 400 m/z
48 MW=316 Pimaric acid, methyl ester (P1)
100 121
316
50
COOMe
301
257
180
181
148 241
0
100 200 300 400 m/z
49 MW=316 Sandaracopimaric acid, methyl ester (P2)
100 301
316
241
50
COOMe
105 149
185 257
213
0
100 200 300 400 m/z
50 MW=316 Isopimaric acid, methyl ester (P3)
100
121
136
93
50
161
79 204
107
0
50 100 150 200 250 m/z
51 MW=204 δ-elemene (S1)
100 161
119
105
50
204
79 94
133
175 189
0
50 100 150 200 250 m/z
52 MW=204 α-cubebene (S2)
100 161
119
105
50
94
204
81
133
147 189
175
0
50 100 150 200 250 m/z
53 MW=204 α-copaene (S3)
100 81 93
68
107
121
50 147
55 161
189
133
175 204
0
50 100 150 200 250 m/z
54 MW=204 ß-elemene (S4)
100 204
50 189
161
105 119
91 133 175
147
79
0
50 100 150 200 250 m/z
55 MW=204 Cyperene (S5)
100 133
H
93
69
161 H
120
50 79 107 148
204
189
55
175
0
50 100 150 200 250 m/z
56 MW=204 Trans-caryphyllene (S6)
100 93
119
50
69
107
55 79
135 161 204

147 189
175
0
50 100 150 200 250 m/z
57 MW=204 α-bergamotene (S7)
100 93
50
80 121
147
204
107
136 161 189

0
50 100 150 200 250 m/z
58 MW=204 α-humulene (S8)
100 161
50
204
105 119
93
81 133
148 189
175
0
50 100 150 200 250 m/z
59 MW=204 γ-cadinene (S9)
100 189
204
81
93 107 133
50
161 H
147
55 175
121
67
0
50 100 150 200 250 m/z
60 MW=204 α-selinene (S10)
100 69
93
50
204
109
81 161
119
55 135
147 189
175
0
50 100 150 200 250 m/z
61 MW=204 ß-bisabolene (S11)
100 161
204
H
50
134
105 119
81 91 189
147 175
0
50 100 150 200 250 m/z
62 MW=204 δ-cadinene (S12)
100 121
93
50
107
204
81 161
67 133
55 189
147
175
0
50 100 150 200 250 m/z
63 MW=204 γ-elemene (S13)
100 316
175
121
81
50 257
134
93
147
105 COOMe 241
161 301
201
187
220 288
0
50 100 150 200 250 300 m/z
64 MW=316 Communic acid, methyl ester
100 81 257
135
93
107 302
119
50 147 163
CH2OMe
175
189
255 270
201 286
215
0
50 100 150 200 250 300 m/z
65 MW=302 Communol, methyl ether
100 121
50 135 257
93 107 163
81
241
COOMe
173 301
147 187 316
201
215
0
50 100 150 200 250 300 m/z
66 MW=316 Ozic acid, methyl ester
100 257
81 95 191
50
109
135
121 CH2OMe
79 161 177
55 67 147
255 287
201 270
241 302
0
50 100 150 200 250 300 m/z
67 MW=302 Ozol, methyl ether
100 257
81 93
137
50 69
109
272
149
175
189
229
0
50 100 150 200 250 300 m/z
68 MW=272 enantio-biformene
100 161
177
105
50
236 COOMe
91
81 121
204
133 221
189
0
50 100 150 200 250 300 m/z
69 MW=236 Pyrolysis product of polycommunic acid, methyl ester
100 173
188
133
50
COOMe
91 119 248
105 145 159
216
233
0
50 100 150 200 250 300 m/z
100 175
COOMe
50
191 235
119 250
107 135
203
95
218
0
50 100 150 200 250 300 m/z

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Atlas of Mass Spectra

Index of spectra by Molecular Weight

MW Atlas MW Atlas MW Atlas

Alphabetical index of spectra

Cativic acid, methyl ester (L3) 41

178 213 342

126 187 216 327

73 327 357 369

185 211 267 294

131 297 343 371

100 OTMS 445

269 297 313

100 153 255

100 143 OTMS

195 255 OAc

100 257 272

100 303 360

149163 238 289

199 177 205

81 109 161 181

107 203 301

135 161 204

136 161 189

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