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Fatty acid


DATA No : DFA8062 INFORMANT : Tetsuyuki Kobayashi

NAME : Methyl-13,16-Dihydroperoxy-9,11,14-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=233-235nm(Ref. 8081/8084)

IR SPECTRA:OOH group: 3712-3140cm-1[bonded], 3530-3510cm-1[free]; olefinic protons: 3005cm-1; conjugated cis, trans diene: 988-979cm-1, 953-935cm-1; isolated trans unsaturation: 968-960cm-1(Ref. 8081/8084)

NMR SPECTRA:1H-NMR(Ref. 8081/8084): C2: 2.3ppm; C8, 17: 1.8-2.2ppm; C9, 10, 11, 12, 14, 15: 5.26-6.28ppm, C13, 16: 4.40-4.42ppm; C18: 1.02ppm; OOH: 8.07ppm

MASS SPECTRA:GC-EI-MS(after reduction and TMS-derivatization)(Ref. 8084): m/e=453[M-CH3]; 439[M -CH2CH3]; 437[M-OCH3]; 378[M-HOTMS]; 143[(CH2)6C00CH3], GC-EI-MS(after reduction, hydrogenation and TMS-derivatization)(102) m/e=443[M-OCH3]; 315[SMTO=CH(CH2)11COOCH3]

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
It is produced from a 16-hydroperoxy isomer during autooxidation of linoleate(Ref. 8025/8026/8081). It is produced from 13- or 16-hydroperoxy isomer during oxidation of linoleate by singlet-oxygen(Ref. 8026/8084/8085).
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[8025]
AUTHOR:Frankel, E. N.
TITLE:Volatile lipid oxidation products PubMed ID:6306693
JOURNAL:Prog Lipid Res.
VOL:22 PAGE : 1-33 (1983)
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[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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[8081]
AUTHOR:Neff, W. E., Frankel, E. N., and Weisleder, D.
TITLE:High Pressure Liquid Chromatography of Autoxidized Lipids: II. Hydroperoxycyclic Peroxides and Other Secondary Products from Methyl Linolenate
JOURNAL:Lipids
VOL:16 PAGE : 439 -448 (1981)
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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)
[TOP]

[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.