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Fatty acid


DATA No : DFA8061 INFORMANT : Tetsuyuki Kobayashi

NAME : Methyl-9,16-Dihydroperoxy-10,12,14-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 triene: lmax=258-260, 268-269, 278-280nm(Ref. 8078/8081/8084)

IR SPECTRA:OOH group: 3712-3140cm-1[bonded], 3530-3510cm-1[free]; olefinic protons: 3005cm-1; conjugated trans, cis, trans triene: 960cm-1; conjugated trans, trans, trans triene: 996-991cm-1(Ref. 8078/8081/8084)

NMR SPECTRA:1H-NMR(Ref. 8081/8084): C2: 2.30-2.37ppm; C8,17: 1.50-1.85ppm; C9, 16: 4.34-4.42ppm; C10, 11, 12, 13, 14, 15: 5.25-6.90ppm; C18: 0.94-0.95ppm; OOH:7.70-7.94ppm

MASS SPECTRA:GC-EI-MS(after reduction and TMS-derivatization)(Ref. 8084), GC-EI-MS(after reduction, hydrogenation and TMS-derivatization)(Ref. 8078/8084), GC-EIMS(after reduction,hydrogenation and TBDMS-derivatization)(Ref. 8078),CI-MS(Ref. 8089)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
It is produced from 9- or 16-hydroperoxy isomer during autooxidation of linoleate(Ref. 8025/8026/8078/8081). Oxidation of linoleate in presence of Fe(III)-ascorbic acid(Ref. 8078). It is produced from 9- 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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[8078]
AUTHOR:Toyoda, I., Terao, J.,And Matsushita, S.
TITLE:Hydroperoxides Formed by Ferrous Ion- Catalyzed Oxidation of Methyl Linolenate
JOURNAL:Lipids
VOL:17 PAGE : 84 -90 (1982)
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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)
[TOP]

[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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[8089]
AUTHOR:Frankel, E. N., Neff, W. E., and Plattner, R. D.
TITLE:Chemichal Ionization- Mass Spectrometry of Secondary Oxidation Products from Methyl Linoleate and Linolenate
JOURNAL:Lipids
VOL:21 PAGE : 333 -337 (1986)
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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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