Table 1 List of compounds identified in the shellac samples.

From: The characterisation of shellac resin by flow injection and liquid chromatography coupled with electrospray ionisation and mass spectrometry

Label

Name

RT (min)

Experimental mass [M-H] −

Calculated mass [M-H] −

Diff (ppm)

Chemical formula

MSMS ESI (-) fragment ions

Free acids

6-oxo-C14

6-oxotetradecanoic acid

8.43

241.1811

241.1809

−0.75

C14H26O3

223, 197, 157, 139

But

Butolic acid

8.13

243.1967

243.1966

−0.54

C14H28O3

197, 141, 85

9,10-diOH-C14

9,10-dihydroxytetradecanoic acid

7.13

259.1919

259.1915

−1.60

C14H28O4

241, 233, 203, 183, 171, 155, 143, 127, 115

Ox-Ljal

Oxidised laccijalaric acid

5.86

261.1134

261.1132

−0.64

C15H18O4

217, 189, 149, 121

Ox-Ljal

Oxidised laccijalaric acid

6.46

261.1134

261.1132

−0.64

C15H18O4

217, 189, 149, 121

Ljal

Laccijalaric acid

5.45

263.1284

263.1289

1.83

C15H20O4

219, 201, 189, 165, 137, 107

Llak

Laccilaksholic acid

5.00

265.1443

265.1445

0.87

C15H22O4

221, 193, 175, 139, 109

E-Llak

Epilaccilaksholic acid

5.42

265.1443

265.1445

0.87

C15H22O4

221, 193, 175, 139, 109

16OH-C16:1

16-hydroxyhexadec-9-enoic acid

8.08

269.2120

269.2122

0.81

C16H30O3

251, 223, 155, 141, 127, 113

16OH-C16

16-hydroxyhexadecanoic acid

8.89

271.2277

271.2279

0.62

C16H32O3

253, 225, 155, 141, 127, 113

Ox-Jal

Oxidised jalaric acid

5.38

277.1086

277.1081

−1.63

C15H18O5

233, 215, 189, 171, 135, 107

Jal

Jalaric acid

4.05

279.1242

279.1238

−1.44

C15H20O5

261, 235, 217, 189, 147, 121, 107

Lshel

Laccishellolic acid

4.52

279.1242

279.1238

−1.44

C15H20O5

235, 217, 187, 103

Jal

Jalaric acid isomer

4.99

279.1242

279.1238

−1.44

C15H20O5

261, 235, 217, 189, 147, 121, 107

Lak

Laksholic

5.35

281.1399

281.1394

−1.60

C15H22O5

263, 237, 219, 201, 147

9,10-diOH-C16:2

9,10-dihydroxyhexadecadienoic acid

6.48

283.1920

283.1915

−1.82

C16H28O4

239, 143, 141, 117

9,10-diOH-C16:1

9,10-dihydroxyhexadecenoic acid

6.26

285.2075

285.2071

−1.28

C16H30O4

239, 171, 143, 125

9,10-diOH-C16

9,10-dihydroxyhexadecanoic acid

6.51

287.2225

287.2228

0.98

C16H32O4

269, 251, 211, 171, 143, 127, 113

Ox-Shel

Oxidised shellolic acid

4.53

293.1037

293.1031

−2.17

C15H18O6

249, 221, 205, 189, 117

Ox-Eshel

Oxidised epishellolic acid

5.08

293.1037

293.1031

−2.17

C15H18O6

249, 221, 205, 189, 117

Shel

Shellolic acid

2.17

295.1191

295.1187

−1.31

C15H20O6

251, 249, 207, 177, 147, 121

E-shel

Epishellolic acid

2.52

295.1191

295.1187

−1.31

C15H20O6

251, 249, 207, 177, 147, 121

Ox-Al

Oxidised aleuritic acid

5.79

301.2013

301.2020

2.47

C16H30O5

283, 265, 171, 127

Al

Aleuritic acid

5.55

303.2176

303.2177

0.32

C16H32O5

285, 267, 227, 201, 171, 155, 127, 113

Esters

Ljal-But

Laccijalaric-butolic

9.79

489.3216

489.3222

1.15

C29H46O6

243, 225

Ljal-(9,10-diOH-C14:1)

Laccijalaric-(9,10-dihydroxytetradecenoic)

8.79

503.3028

503.3014

−2.72

C29H44O7

257, 217

Ljal-(9,10-diOH-C14)

Laccijalaric-(9,10-dihydroxytetradecanoic)

8.58

505.3175

505.3171

−0.83

C29H46O7

259

Ljal-(16OH-C16:1)

Laccijalaric-(16-hydroxyhexadec-9-enoic)

9.98

515.3372

515.3378

1.19

C31H48O6

269

Ljal-(16OH-C16)

Laccijalaric-(16-hydroxyhexadecanoic)

10.44

517.3526

517.3535

1.66

C31H50O6

271, 247

Jal-(9,10-diOH-C14)

Jalaric-(9,10-dihydroxytetradecanoic)

7.95

521.3130

521.3120

−1.93

C29H46O8

279, 261, 217

Ljal-(9,10-diOH-C16:2)

Laccijalaric-(9,10-dihydroxyhexadecadienoic)

8.37

529.3182

529.3171

−2.12

C31H46O7

283

Ljal-(9,10-diOH-C16:1)

Laccijalaric-(9,10-dihydroxyhexadecenoic)

8.22

531.3325

531.3327

0.43

C31H48O7

285

Jal-(16OH-C16:1)

Jalaric-(16-hydroxyhexadec-9-enoic)

8.97

531.3325

531.3327

0.43

C31H48O7

269, 261, 217, 161, 121

Ljal-(9,10-diOH-C16)

Laccijalaric-(9,10-dihydroxyhexadecanoic)

8.47

533.3471

533.3484

2.39

C31H50O7

287

Jal-(16OH-C16)

Jalaric-(16-hydroxyhexadecanoic)

9.40

533.3471

533.3484

2.39

C31H50O7

287, 271, 261, 217, 189, 149, 121

Al-?

Unidentified ester I

7.06

535.3267

535.3276

1.76

C30H48O8

303, 277, 247, 233, 185, 133

Al-?

Unidentified ester II

6.89

537.3430

537.3433

0.54

C30H50O8

303, 287, 249

Ljal-(Ox-Al)

Laccijalaric- oxidised aleuritic

7.82

547.3267

547.3276

1.72

C31H48O8

503, 301, 261, 217, 147

Ljal-Al

Laccijalaric-aleuritic

7.50

549.3435

549.3433

−0.38

C31H50O8

303, 287, 261, 217, 161, 121

Al-Llak

Aleuritic-Llak

6.40

551.3220

551.3226

1.01

C30H48O9

303, 265, 247, 185

Al-?

Unidentified ester III

6.07

553.3386

553.3382

−0.71

C30H50O9

303, 285, 249, 149

Jal-(Ox-Al)

jalaric- oxidised aleuritic

7.11

563.3236

563.3226

−1.85

C31H48O9

301, 277, 261, 233, 217, 147

Jal-Al

Jalaric-aleuritic

6.66

565.3384

565.3382

−0.34

C31H50O9

303, 261, 217, 121

Jal-Al

Jalaric-aleuritic

6.78

565.3384

565.3382

−0.34

C31H50O9

303, 285, 261, 217, 121

Lshel-Al

Laccishellolic-aleuritic

7.02

565.3384

565.3382

−0.34

C31H50O9

303, 279, 261, 233, 217, 147

Lak-Al

Laksholic-aleuritic

7.52

567.3529

567.3539

1.68

C31H52O9

303, 287, 279, 263, 217

Elak-Al

Epilaksholic-aleuritic

6.55

567.3529

567.3539

1.68

C31H52O9

303, 287, 279, 263, 217

Shel-(ox-Al)

Shellolic-aleuritic oxidised

6.93

579.3186

579.3175

−1.94

C31H48O10

301, 277, 261, 233, 217, 121

Shel-Al

Shellolic-aleuritic

6.26

581.3345

581.3331

−2.37

C31H50O10

303, 277, 233

Diesters**

Ljal-(9,10-diOH-C14)-But

Laccijalaric-(9,10-dihydroxytetradecanoic)-butolic

11.48

731.5102

731.5104

0.21

C43H72O9

485, 259, 243

Ljal-(16OH-C16:1)-But

Laccijalaric-(16-hydroxyhexadec-9-enoic)-butolic

12.91

741.5303

741.5311

1.07

C45H74O8

495, 269, 243

Ljal-(9,10-diOH-C16:2)-But

Laccijalaric-(9,10-dihydroxyhexadecadienoic)-butolic

11.66

755.5100

755.5104

0.47

C45H72O9

509, 283, 243

Jal-(16OH-C16:1)-But

Jalaric-(16-hydroxyhexadec-9-enoic)-butolic

12.31

757.5256

757.5260

0.54

C45H74O9

495, 269, 261, 243, 217

Ljal-(9,10-diOH-C16)-But-

Laccijalaric-(9,10-dihydroxyhexadecanoic)-butolic

11.75

759.5399

759.5417

2.31

C45H76O9

513, 287, 243

Jal-(16OH-C16)-But

Jalaric-(16-hydroxyhexadecanoic)-butolic

12.72

759.5399

759.5417

2.31

C45H76O9

513, 279, 261, 243, 227

Ljal-Al-But

Laccijalaric-aleuritic-butolic

10.44

775.5364

775.5366

0.22

C45H76O10

529, 303, 285, 243

Ljal-Al-But

Laccijalaric-aleuritic-butolic

10.95

775.5364

775.5366

0.22

C45H76O10

529, 303, 261, 243, 217

Jal-(9,10-diOH-C16)-But-

Jalaric-(9,10-dihydroxyhexadecanoic)-butolic

11.10

775.5364

775.5366

0.22

C45H76O10

513, 287, 261, 243, 217

Jal-Al-But

Jalaric-aleuritic-butolic

9.68

791.5316

791.5315

−0.14

C45H76O11

529, 303, 285, 261, 243, 217

Jal-Al-But

Jalaric-aleuritic-butolic

10.19

791.5316

791.5315

−0.14

C45H76O11

529, 303, 261, 243, 217

Shel-Al-But

Shellolic-aleuritic-butolic

9.11

807.5280

807.5264

−1.98

C45H76O12

529, 303, 285, 277, 243, 233, 217

Shel-Al-But

Shellolic-aleuritic-butolic

9.69

807.5280

807.5264

−1.98

C45H76O12

529, 277, 243

Ljal-Al-Jal

Laccijalaric-aleuritic-jalaric

8.29

811.4646

811.4638

−0.98

C46H68O12

565, 549, 531, 303, 279, 261, 217

Jal-Al-Jal-

Jalaric-aleuritic-jalaric

7.31

827.4603

827.4587

−1.91

C46H68O13

565, 279, 261, 217

Jal-Shel-Al

Jalaric-aleuritic-shellolic-

6.94

843.4525

843.4536

1.34

C46H68O14

581, 565, 303, 277, 233

Jal-Shel-Al

Jalaric-aleuritic-shellolic

7.32

843.4525

843.4536

1.34

C46H68O14

581, 565, 547, 303, 293, 277, 261, 233

Jal-Al-Al

Jalaric-aleuritic-aleuritic

7.53

851.5521

851.5526

0.61

C47H80O16

589, 563, 303, 261

Triesters**

Ljal-Al-(16OH-C16:1)-Ljal

Laccijalaric-aleuritic-(16-hydroxyhexadec-9-enoic)-laccijalaric

11.54

1047.676

1047.678

1.54

C62H96O13

801, 549, 531, 515, 303, 269, 263

Ljal-(9,10-diOH-C16)-Ljal-(16OH-C16:1)

Laccijalaric-(16-hydroxyhexadec-9-enoic)-laccijalaric-(9,10-dihydroxyhexadecanoic)

11.92

1047.676

1047.678

1.54

C62H96O13

801, 777, 555, 531, 517, 503, 487, 287, 269, 263

Ljal-Al-Jal-(16OH-C16:1)

Laccijalaric-aleuritic-jalaric-(16-hydroxyhexadec-9-enoic)

11.10

1063.671

1063.673

1.44

C62H96O14

817, 793, 573, 55, 531, 487, 303, 285, 269, 261, 217

Jal-Al-(16OH-C16:1)-Jal-

Jalaric-aleuritic-(16-hydroxyhexadec-9-enoic)-jalaric-

9.89

1079.667

1079.668

1.06

C62H96O15

817, 547, 531, 303, 269, 261, 217

Ljal-Al-Jal-(9,10-diOH-C16:1)

Laccijalaric-aleuritic-(9,10-dihydroxyhexadecenoic)-jalaric

10.11

1079.667

1079.668

1.06

C62H96O15

833, 817, 571, 547, 531, 503, 303, 285, 277, 261, 217

Ljal-Al-Al-Ljal

Laccijalaric-aleuritic-aleuritic-laccijalaric

9.49

1081.682

1081.683

1.29

C62H98O15

835, 589, 549, 303, 263

Jal-Al-(9,10-diOH-C16:1)-Jal-

Jalaric-aleuritic-(9,10-dihydroxyhexadecenoic)-jalaric-

9.56

1095.664

1095.663

−1.59

C62H96O16

833, 587, 571, 547, 303, 285, 277, 261, 217

Jal-Al-(16OH-C16:1)-Shel

Jalaric-aleuritic-(16-hydroxyhexadec-9-enoic)-shellolic

9.27

1095.664

1095.663

−1.59

C62H96O16

833, 571, 547, 529, 303, 277, 269, 261, 233, 217

Ljal-Al-Al-Jal

Laccijalaric-aleuritic-aleuritic-jalaric

8.78

1097.677

1097.678

1.01

C62H98O16

851, 835, 589, 565, 549, 303, 287, 261, 217

Ljal-Al-Al-Jal

Laccijalaric-aleuritic-aleuritic-jalaric

9.03

1097.677

1097.678

1.01

C62H98O16

851, 835, 589, 565, 547, 303, 261, 217

Jal-Al-Al-Jal

Jalaric-aleuritic-aleuritic-jalaric

8.17

1113.676

1113.673

−2.22

C62H98O17

851, 589, 565, 547, 303, 261

Jal-Al-Al-Shel

Jalaric-aleuritic-aleuritic-shellolic

7.68

1129.670

1129.668

−1.82

C62H98O18

867, 851, 589, 565, 303, 277, 261, 233

Shel-Al-Al-Shel

Shellolic-aleuritic-aleuritic-shellolic

7.26

1145.664

1145.663

−0.65

C62H98O19

867, 605, 581, 563, 303, 277, 233

Tetraesters**

Ljal-Al-But-Al-Ljal

Laccijalaric-aleuritic-butolic-aleuritic-laccijalaric

12.12

1307.880

1307.876

2.18

C76H124O17

1061, 815, 775, 571, 549, 529, 303, 263, 261, 243

Ljal-Al-But-Al-Jal

Laccijalaric-aleuritic-butolic-aleuritic-jalaric

11.77

1323.869

1323.872

1.65

C76H124O18

1077, 1061, 815, 775, 547, 529, 513, 303, 261, 243

Jal-Al-But-Al-Jal

Jalaric-aleuritic-butolic-aleuritic-jalaric

10.95

1339.864

1339.866

1.50

C76H124O19

1077, 815, 791, 773, 565, 547, 529, 303, 261, 243

Ljal-Al-But-Al-Shel

Laccijalaric-aleuritic-butolic-aleuritic-shel

11.31

1339.864

1339.866

1.50

C76H124O19

1077, 815, 773, 547, 529, 303, 277, 261, 243

Ljal-Al-But-Al-Jal

Jalaric-aleuritic-butolic-aleuritic-shel

10.25

1355.863

1355.861

−1.46

C76H124O20

1093, 1077, 815, 791, 589, 563, 547, 529, 303, 277, 261, 233

Ljal-Al-Jal-Al-Jal

Laccijalaric-aleuritic-jalaric-aleuritic-jalaric

9.20

1359.800

1359.799

−0.79

C77H116O20

1113, 1097, 851, 835, 565, 547, 303, 279, 261

Jal-Al-Jal-Al-Jal

Jalaric-aleuritic-jalaric-aleuritic-jalaric

8.56

1375.796

1375.794

−1.36

C77H116O21

1113, 851, 827, 565, 547, 303, 279, 261, 217

Jal-Al-Jal-Al-Shel

Jalaric-aleuritic-jalaric-aleuritic-shellolic

8.21

1391.790

1391.789

−1.11

C77H116O22

1129, 1113, 851, 809, 581, 565, 547, 303, 277, 261, 233

Jal-Al-Al-Al-Jal

Jalaric-aleuritic-aleuritic-aleuritic-jalaric

8.65

1399.885

1399.888

2.09

C78H128O21

1137, 875, 851, 589, 565, 547, 303, 261, 217

Pentaesters** a

Ljal-Ljal-Ljal-Al-Al-Al

Laccijalaric-laccijalaric-laccijalaric-aleuritic-aleuritic-aleuritic

11.22

1614.019

1614.023

2.41

C93H146O22

1368, 1353, 1121, 1105, 875, 835, 589, 547, 531, 303, 261

Ljal-Ljal-Jal-Al-Al-Al

Laccijalaric-laccijalaric-jalaric-aleuritic-aleuritic-aleuritic

10.30

1630.017

1630.018

0.50

C93H146O23

1383, 1369, 1137, 1121, 1098, 851, 835, 589, 565, 549, 531, 303, 261

Ljal-Ljal-Shel-Al-Al-(9,10-diOH-C16)

Laccijalaric-laccijalaric-shellolic-aleuritic-aleuritic-(9,10-dihydroxyhexadecanoic)

11.40

1630.017

1630.018

0.50

C93H146O23

1383, 1367, 1121, 1105, 1081, 835, 819, 589, 573, 565, 547, 531, 303, 287, 277, 261

Ljal-Jal-Jal-Al-Al-Al

Laccijalaric-jalaric-jalaric-aleuritic-aleuritic-aleuritic

9.62

1646.010

1646.013

2.02

C93H146O24

1400, 1384, 1138, 1122, 1096, 1081, 852, 833, 589, 565, 547, 303, 261

Ljal-Jal-Shel-Al-Al-(9,10-diOH-C16)

Laccijalaric-jalaric-shellolic-aleuritic-aleuritic-(9,10-dihydroxyhexadecanoic)

10.46

1646.010

1646.013

2.02

C93H146O24

1384, 1122, 1096, 1079, 876, 851, 835, 589, 573, 565, 547, 531, 303, 287, 277, 261

Jal-Jal-Jal-Al-Al-Al

Jalaric-jalaric-jalaric-aleuritic-aleuritic-aleuritic

9.08

1662.007

1662.008

0.87

C93H146O25

1400, 1138, 1114, 1096, 852, 810, 589, 565, 547, 303, 261

Ljal-Jal-Shel-Al-Al-Al

Laccijalaric-jalaric-shellolic-aleuritic-aleuritic-aleuritic

9.42

1662.007

1662.008

0.87

C93H146O25

1400, 1358, 1138, 1096, 851, 834, 809, 589, 565, 547, 303, 277, 261

Jal-Jal-Shel-Al-Al-Al

Jalaric-jalaric-shellolic-aleuritic-aleuritic-aleuritic

9.07

1678.001

1678.003

1.11

C93H146O26

1416, 1400, 1138, 1113, 1096, 852, 589, 565, 547, 303, 277, 261, 233

Hexaesters** a

Jal-Jal-Jal-Al-Al-Al-But

Jalaric-jalaric-jalaric-aleuritic-aleuritic-aleuritic-butolic

11.44

1888.199

1888.201

1.23

C107H172O27

1627, 1364, 1348, 1113, 1077, 851, 792, 589, 565, 547, 529, 303, 261, 243

Heptaesters** a

Ljal-Jal-Jal-Jal-Al-Al-Al-Al

Laccijalaric-jalaric-jalaric-jalaric-aleuritic-aleuritic-aleuritic-aleuritic

10.52

2195.346

2194.348

1.16

C124H194O32

1933, 1687, 1671, 1400, 1358, 1138, 1097, 1080, 851, 810, 781, 565, 547, 303, 261

Jal-Jal-Jal-Jal-Al-Al-Al-Al

Jalaric-jalaric-jalaric-jalaric-aleuritic-aleuritic-aleuritic-aleuritic

9.82

2210.339

2210.343

1.61

C124H194O33

1949, 1687, 1401, 1358, 1138, 1113, 1096, 852, 833, 589, 565, 547, 303, 261

Jal-Jal-Jal-Shel-Al-Al-Al-Al

Jalaric-jalaric-jalaric-shellolic-aleuritic-aleuritic-aleuritic-aleuritic

8.45

2226.341

2226.338

−1.18

C124H194O34

1965, 1948, 1687, 1374, 1113, 851, 565, 303, 261

  1. Retention times – RT –, difference between the experimental and calculated masses of the deprotonated molecules [M-H]− – diff(ppm) –, chemical formulas and nominal masses* of the fragment ions present in the MS/MS spectra are reported. *The measured accurate masses of the fragment ions are reported in the corresponding MS/MS spectra shown in the Appendix (Supplementary Information). The accuracy of measurements in MS/MS experiments is usually lower than MS experiments, but four decimal digits have been displayed for consistency.
  2. **Isomers are generally present with differences in the relative abundances of m/z peaks. The retention time of the most abundant isomer is reported.
  3. aThe exact order in which the acids are linked in the polyester was not ascertained.
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