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Fatty acid


DATA No : DFA8066 INFORMANT : Tetsuyuki Kobayashi

NAME : Methyl-9,15-Dihydroperoxy-10,12,16-Octadecatrienoate

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


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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:Conjugated diene: lmax=237nm(Ref. 8084)

IR SPECTRA:OOH group: 3700-3140cm-1[bonded], 3520-3510cm-1[free]; conjugated trans, cis diene: 985-979cm-1, 953-935cm-1; isolated trans unsaturation: 968-960cm-1(Ref. 8084)

NMR SPECTRA:1H-NMR(Ref. 8084): C2: 2.31ppm; C8, 14: 1.75-1.85ppm; C9, 15: 4.40ppm; C10, 11, 12, 13, 16, 17: 5.25-6.90ppm; C18: 1.8ppm; OOH: 7.83-7.88ppm(Ref. 8084)

MASS SPECTRA:GC-EI-MS(after reduction and TMS-derivatization)(Ref. 8084): m/e=157[(CH2)7COOCH3] 143[SMTO=CHCH=CHCH3]

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
It is produced from 9- or 15-hydroperoxy isomer during oxidation of linoleate by singlet-oxygen(Ref. 8026/8084/8085).
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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[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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[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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[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.