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Lipid peroxide


DATA No : OPO8001 INFORMANT : Tetsuyuki Kobayashi

NAME : 9-Hydroperoxy-10,12-Octadecadienoic Acid/9-Hydroperoxy-10,12-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. 8043/8044/8045/8046/8047/8048/8049)
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 =25900, trans, trans isomer: l max=233nm, e=28600 (Ref. 8001/8002/8003/8004/8005/8011)

IR SPECTRA: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

NMR SPECTRA: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)

MASS SPECTRA: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]

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
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.
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.