| Id | Image | COMMON NAME | NAME | DATA No |
Lipid class | INFORMANT | SYMBOL | FORMULA | MOL.WT(average) | Download cdx file / Mol format file |
BIOOGICAL ACTIVITY |
PHYSICAL AND CHEMICAL PROPERTIES |
SPECTRAL DATA |
CHROMATOGRAM DATA |
SOURCE |
CHEMICAL SYNTHESIS |
METABOLISM |
GENETIC INFORMATION |
NOTE |
REFERENCES |
|---|
| MELTING POINT | BOILING POINT | DENSITY | REFRACTIVE INDEX | OPTICAL ROTATION | SOLUBILITY |
UV SPECTRA | IR SPECTRA | NMR SPECTRA | MASS SPECTRA | OTHER SPECTRA |
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| 1 | | | 9-Hydroperoxy-10,12-Octadecadienoic Acid/9-Hydroperoxy-10,12-Octadecadienoate | OPO8001 | Lipid peroxide | Tetsuyuki Kobayashi | | C18H32O4 | 312.444 | | Pysiological damages are induced by these hydroperoxides which are incorporated into bodies or synthesized endogenously.<< Ref. 8043/8044/8045/8046/8047/8048/8049>> | | | | | | | Trans, cis isomer: l max=236nm, e =25900, trans, trans isomer: l max=233nm, e=28600 << Ref. 8001/8002/8003/8004/8005/8011>> | Methyl ester: << Ref. 8001/8005/8006/8007/8008/8009/8010/8011>>: trans, cis isomer: 986 and 949cm-1, trans, trans isomer: 989cm-1, OOH group: 3550cm-1 | 1H-NMR<< Ref. 8001/8012>>, 1H-NMR( after methanolyzation and reduction)<< Ref. 8005/8017>>: trans,cis isomer: C10-13 (5.42-6.48ppm), C14 (2.10-2.18ppm), C9(4.15ppm), J10-11= 15.4Hz(trans), J12-13= 10.8Hz (cis), trans, trans isomer: olefinic protons (5.41ppm), C14 (2.07ppm), C9 (4.20ppm) | GC/EI-MS(after methanolysis, reduction and trimethylsilylation) << Ref. 8012/8018/8013/8019/8014>>: m/e= 382[M], 292[M-HOTMS], 311[M-(CH2)4CH3], 225[M-(CH2)7COOCH3] standard peak/ GC-EI-MS(after methylation, reduction and hydrogenation) << Ref. 8020/8015/8016>>: m/e= 187[CH(OH)(CH2)7COOCH3], 158[(CH2)7COOCH3+H], 155[C(OH)-(CH)7CO] | | | Auto oxidation of methyllinoleate<< Ref. 8021/8022/8023/8024/8025/8026/8027/8039/8028/8029/8030>>. Oxidation of methyl linoleate by singlet oxygen<< Ref. 8022/8023/8025/8026/8027/8039/8030/8024>>. Oxidation of linoleic acid by lipoxygenase<< Ref. 8023/8031/8032/8033/8034/8035/8037/8038/8036>>. Production mechanism (auto oxidation): bis-allylic hydrogen at C11. | | | | | |
| 2 | | | 13- Hydroperoxy-9,11-Octadecadienoic Acid/13- Hydroperoxy-9,11-Octadecadienoate | OPO8002 | Lipid peroxide | Tetsuyuki Kobayashi | | C18H32O4 | 312.444 | | Pysiological damages are induced by these hydroperoxides which are incorporated into bodies or synthesized endogenously.<< Ref. 8043/8044/8045/8046/8047/8048>> | | | | | | | Trans , cis isomer: l max= 236nm, e= 26000, trans, trans isomer: l max= 233nm, e=28600 (025/027/028/029/036) | Methyl ester<< Ref. 8001/8006/8007/8008/8009/8010/8011>>: cis, trans isomer: 986 and 949cm-1, trans, trans isomer: 989cm-1, OOH group: 3550cm-1 | 1H-NMR << Ref. 8001/8012>>: C9-13 (5.45-6.53ppm), C13 (4.37ppm), J9-10= 11Hz (cis),J11-12=15Hz (trans) /1H-NMR (after methanolyzation and reduction )<< Ref. 8005/8017>>: cis, trans isomer : olefinic protons(5.91ppm), C8 (2.10ppm), C13(4.15ppm), trans, trans isomer: olefinic protons (5.41ppm), C8 (2.07ppm) | GC-EI-MS(after methanolysis, reduction and trimethylsilylation) << Ref. 8012/8018/8019/8013/8014>>: m/e= 382[M], 292[M-HOTMS], 311[M-(CH2)4CH3] standard peak,225[M-(CH2)7COOCH3] / GC-EI-MS(after methylation, reduction and hydrogenation) << Ref. 8020/8015/8016>>: m/e= 243[CH(OH)(CH2)11COOCH3], 214[(CH2)11COOCH3+H], 211[C(OH(CH2)11CO) | | | Auto oxidation of methyl linoleate<< Ref. 8029/8021/8022/8023/8024/8025/8026/8039/8028/8030>>. Oxidation of methyl linoleate by singlet oxygen<< Ref. 8022/8023/8025/8026/8027/8030/8024>>. Oxidation of linoleic acid by lipoxygenase<< Ref. 8023/8031/8032/8033/8034/8035/8037/8038/8036>>. Production mechanism (auto oxidation): bis-allylic hydrogen at C11. | | | | | |
| 3 | | | 10-Hydroperoxy-8,12-Octadecadienoic Acid/10-Hydroperoxy-8,12-Octadecadienoate | OPO8003 | Lipid peroxide | Tetsuyuki Kobayashi | | C18H32O4 | 312.444 | | Pysiological damages are induced by these hydroperoxides which are incorporated into bodies or synthesized endogenously.<< Ref. 8043/8044/8045/8046/8047/8048/8049>> | | | | | | | | After methanolyzation and reduction<< Ref. 8091/8090>>: isolated double bond (3013-3010, 972-971cm-1) | 1H-NMR(after methanolyzation and reduction)<< Ref. 8091>>: olefinic protons(5.55-5.59ppm), C10 (4.08-4.11ppm) | GC-EI-MS(after methanolysis, reduction and trimethylsilylation)<< Ref. 8090/8019>>: m/e= 271[SMTO=CH-CH=CH-(CH2)6COOCH3], GC-EI-MS (after methylation, reduction and hydrogenation)<< Ref. 8020>>:m/e= 201[CH(OH)(CH2)8COOCH3], 172[(CH2)8COOCH3+H], 169[C(OH)(CH2)8CO] GC-EI-MS(after methylation, reduction, hydrogenation and trimethylsilylation)<< Ref. 8090>> | | | Oxidation of methyl linoleate by singlet oxygen<< Ref. 8043/8044/8045/8046/8047/8048/8049>>. | | | | | |
| 4 | | | 12-Hydroperoxy-9,13-Octadecadienoic Acid/12-Hydroperoxy-9,13-Octadecadienoate | OPO8004 | Lipid peroxide | Tetsuyuki Kobayashi | | C18H32O4 | 312.444 | | Pysiological damages are induced by these hydroperoxides which are incorporated into bodies or synthesized endogenously.<< Ref. 8043/8044/8045/8046/8047/8048/8049>> | | | | | | | | After methanolyzation and reduction<< Ref. 8091/8090>>: isolated double bond (3013-3010, 972-971cm-1) | 1H-NMR(after methanolyzation and reduction)<< Ref. 8091>>: olefinic protons(5.55-5.59ppm), C10 (4.08-4.11ppm) | GC-EI-MS(after methanolysis, reduction and trimethylsilylation)<< Ref. 8090/8019>>: m/e= 185[SMTO=CH-CH=CH-(CH2)3CH3], GC-EI-MS (after methylation, reduction and hydrogenation)<< Ref. 8020>>: m/e= 229[CH(OH)(CH2)10COOCH3], 200[(CH2)10COOCH3+H], 197[C(OH)(CH2)10CO] GC-EI-MS(after methylation, reduction, hydrogenation and trimethylsilylation)<< Ref. 8090>> | | | Oxidation of methyl linoleate by singlet oxygen<< Ref. 8024/8022/8023/8025/8026/8027/8039/8030>>. | | | | | |
| 5 | | | 8-Hydroperoxy-9,12-Octadecadienoic Acid | OPO8005 | Lipid peroxide | Tetsuyuki Kobayashi | | C18H32O4 | 312.444 | | | | | | | | | | | 1H-NMR (after methanolyzation, reduction and 400MHz )<< Ref. 8050>>: olefinic protons(5.91-5.51ppm), C8 (4.45ppm), C11(2.84ppm), C14(2.05ppm),J9-10= J12-13= 10.7Å }0.2Hz (cis) | GC-EI-MS(after methanolysis, reduction and trimethylsilylation) <<8050>: m/e= 292[M-HOTMS], 271[CH=CH-CH(OTMS)-(CH2)6COOCH3], 239[M-(CH2)6C00CH3], 173[SMTO=CH-(CH2)6COOCH3-TMS+H], 149[239-HOTMS] standard peak | | | A minor component of monohydroperoxide generated from linoleic acid or methyllinoleate by autooxidation<< Ref. 8050/8051>>. A minor component of hydroperoxide generated from linoleic acid through oxidation by soy bean lipoxygenase (type-2)<< Ref. 8050>>. | | | | 8-OOH and 14-OOH are known as small amount components of monohydroperoxidate from auto oxidation of linoleic acid and oxidation of soybean lipoxygenase(type-2). Their amount oes not change by temperature or addition of a-tocopherol<< Ref. 8050>>. | |
Last updated June 14, 2022. Copyright © 1989-2022 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.
