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Lipid peroxide


DATA No : OPO8002 INFORMANT : Tetsuyuki Kobayashi

NAME : 13- Hydroperoxy-9,11-Octadecadienoic Acid/13- Hydroperoxy-9,11-Octadecadienoate

COMMON NAME:
SYMBOL:
FORMULA: C18H32O4 MOL.WT (average) : 312.444
BIOLOGICAL ACTIVITY
Pysiological damages are induced by these hydroperoxides which are incorporated into bodies or synthesized endogenously.(Ref. 8043/8044/8045/8046/8047/8048)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:Trans , cis isomer: l max= 236nm, e= 26000, trans, trans isomer: l max= 233nm, e=28600 (025/027/028/029/036)

IR SPECTRA: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

NMR SPECTRA: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)

MASS SPECTRA: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)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
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.
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.