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Lipid peroxide

(total 5)


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IdImageCOMMON NAMENAMEDATA No Lipid classINFORMANTSYMBOLFORMULAMOL.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 POINTBOILING POINTDENSITYREFRACTIVE INDEXOPTICAL ROTATIONSOLUBILITY UV SPECTRAIR SPECTRANMR SPECTRAMASS SPECTRAOTHER SPECTRA
1
9-Hydroperoxy-10,12-Octadecadienoic Acid/9-Hydroperoxy-10,12-Octadecadienoate OPO8001Lipid peroxideTetsuyuki Kobayashi C18H32O4 312.444Pysiological 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 OPO8002Lipid peroxideTetsuyuki Kobayashi C18H32O4 312.444Pysiological 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 OPO8003Lipid peroxideTetsuyuki Kobayashi C18H32O4 312.444Pysiological 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 OPO8004Lipid peroxideTetsuyuki Kobayashi C18H32O4 312.444Pysiological 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 OPO8005Lipid peroxideTetsuyuki 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.