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Fatty acid


DATA No : DFA8068 INFORMANT : Tetsuyuki Kobayashi

NAME : Methyl-10,12,13,15-Bisepidioxy-16-Hydroperoxy-8-Octadecenoate

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


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BIOLOGICAL ACTIVITY
It reacts with DNA in the presence of Fe ions and ascorbic acid(Ref. 8096).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:OOH group: 3700-3150cm-1[bonded], 3530cm-1[free]; isolated trans unsaturation: 960cm-1(Ref. 8084)

NMR SPECTRA:1H-NMR(Ref. 8084): C2: 2.3ppm; C8: 5.35ppm; C9: 5.88ppm; C10, 12, 13, 15: 4.47ppm; C11, 14: 2.1-2.8ppm; C16: 3.88ppm[C15-16 erythro], 4.17ppm[C15-16 threo]; C18: 1.05ppm; OOH: 8.73ppm[C15-16 erythro], 9.20ppm[C15-16 threo] (Ref. 8084)

MASS SPECTRA:GC-EI-MS(after reduction(PH3P) and TMS-derivatization)(105): m/e=313[M-131]; 131[SMTO=CHCH2CH3]; GC-EI-MS(after reduction,hydrogenation, and TMS-derivatization)(Ref. 8084): m/e=349[SMTO=CHCH2CH(OTMS)CH(OTMS)CH2CH3]; 273[SMTO=CH(CH2)8COOCH3]

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
It is produced from a 10-peroxyradical by singlet-oxygen mediated oxidation of linoleate via succesive 1,3-cyclization(Ref. 8026/8039/8084).
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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[8039]
AUTHOR:Frankel, E. N.
TITLE:Secondary products of lipid oxidation PubMed ID:3311422
JOURNAL:Chem Phys Lipids.
VOL:44 PAGE : 73-85 (1987)
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[8084]
AUTHOR:Neff, W. E., Frankel, E. N., and Weisleder, D.
TITLE:Photosensitized Oxidation of Methyl Linolenate. Secondary Products
JOURNAL:Lipids
VOL:17 PAGE : 780 -790 (1982)
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[8096]
AUTHOR:Fujimoto, K., Neff, W. E., and Frankel, E. N.
TITLE:The reaction of DNA with lipid oxidation products, metals and reducing agents PubMed ID:6466690
JOURNAL:Biochim Biophys Acta.
VOL:795 PAGE : 100-107 (1984)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.