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Fatty acid


DATA No : DFA8077 INFORMANT : Tetsuyuki Kobayashi

NAME : Methyl-9,12,13,15-Bisepidioxy-16-Hydroperoxy-10-Octadecenoate

COMMON NAME:
SYMBOL:
FORMULA: C19H32O8 MOL.WT (average) : 388.453


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:1H-NMR(Ref. 8085): C9, 12, 13, 15: 4.45ppm; C10, 11: 5.68ppm; C14: 2.1-2.7ppm; C16: 4.08 ppm; C17: 1.6ppm; OOH: 8.45ppm

MASS SPECTRA:GC-EI-MS(after reduction(PH3P) and TMS-derivatization)(Ref. 8085): m/e=313[M-131]; 131[SMTO=CHCH2CH3]; GC-EI-MS(after reduction, hydrogenation, and TMS-derivatization)(Ref. 8085): m/e=389[SMTO=CH(CH2)2CH(OTMS)(CH2)7COOCH3]; 299[389-HOTMS]; 259[SMTO=CH(CH2)7COOCH3]

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
It is produced from 13,15-epidioxy-16-hydroperoxides by 1,4-adduct of singlet-oxygen mediated oxidation of 13-peroxyradical linoleate via 1,3-cyclization(Ref. 8026/8085).
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[8026]
AUTHOR:Frankel, E. N.
TITLE:Chemistry of free radical and singlet oxidation of lipids PubMed ID:6100997
JOURNAL:Prog Lipid Res.
VOL:23 PAGE : 197-221 (1984)
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[8085]
AUTHOR:Neff, W. E., and Frankel, E. N.
TITLE:Photosensitized Oxidation of Methyl Linolenate Monohydroperoxides: Hydro-Peroxy Cyclic Peroxides, Dihydroperoxides and Hydroperoxy Bis- Cyclic Peroxides
JOURNAL:Lipids
VOL:19 PAGE : 952 -957 (1984)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.