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Fatty acid


DATA No : DFA8074 INFORMANT : Tetsuyuki Kobayashi

NAME : Methyl-10,13-Epdioxy-9-Hydroperoxy-11,15-Octadecadienoate

COMMON NAME:
SYMBOL:
FORMULA: C19H32O6 MOL.WT (average) : 356.454


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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:OOH group: 3635-3300cm-1[bonded]; olefinic protons: 3005cm-1; isolated trans unsaturation: 965cm-1 (Ref. 8085)

NMR SPECTRA:1H-NMR(Ref. 8085): C8: 1.6ppm; C9: 4.22ppm; C10: 4.65ppm; C11, 12: 5.98ppm; C13: 4.48ppm; C14: 2.0ppm; C15, 16: 5.45ppm; C17: 2.05ppm; OOH: 8.65ppm

MASS SPECTRA:GC-EI-MS(after reduction(PH3P) and TMS-derivatization)(Ref. 8085): m/e=412[M]; 322[M-HOTMS]; 259[SMTO=CH(CH2)7COOCH3]; 153[M-259]; 69[CH2CH=CHCH2CH3]; 55[CH=CHCH2CH3]; GC-EI-MS(after reduction, hydrogenation, and TMS-derivatization)(106): m/e=457[M-CH3-HOTMS]

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
It is produced from a 9-hydroperoxide isomer of linoleate by 1,4-adduct of singlet-oxygen(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.