Back to HOME

Fatty acid


DATA No : DFA8089 INFORMANT : Tetsuyuki Kobayashi

NAME : 8,15-Dihydroperoxy-5,9,11,13-Eicosatetraenoic Acid/8,15-Dihydroperoxy-5,9,11,13-Eicosatetraenoate

COMMON NAME:
SYMBOL:
FORMULA: C20H32O6 MOL.WT (average) : 368.464


Download ChemDraw structure data
Download Mol format file
BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:UV(Me-ester)(Ref. 8098) conjugated triene: 270nm and 281nm

IR SPECTRA:IR(Me-estre)(Ref. 8098)OOH group: 3400cm-1, IR(after reduction)(Ref. 8108) trans unsaturation: 968cm-1, OH group: 1040, 3540cm-1

NMR SPECTRA:1H-NMR(Me-ester)(Ref. 8098) OOH: 8.3ppm, 1H-NMR(after reduction)(Ref. 8108) C8, C15: 4.2ppm; OH: 6.3ppm

MASS SPECTRA:EI-MS(Me-ester; after reduction)(Ref. 8108): m/e=350[M]; 332[M-H2O]; 301[332-OCH3]; 261[332-(CH2)4CH3]; 209[M-CH=CH(CH2)4COOCH3]; 191[209-H2O]; GC-EI-MS(Me-ester; after reduction, hydrogenation and TMS)(Ref. 8097/8098): m/e=487[M-CH3]; 431[M-(CH2)4CH3]; 359[M-(CH2)6COOCH3]

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Autooxidation of arachidonic acid(Ref. 8097). In degradation products of 15-hydroperoxides of arachidonic acid in the presence of Fe(III)-ascorbic acid. Oxidation of arachidonic acid by singlet-oxygen(Ref. 8098). It is produced enzymatically from 15-HPETE in vivo(8,15-DHPETE)(Ref. 8103/8104). It is produced from 15-HPETE by soy bean lipoxygenase(Ref. 8108).
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[8097]
AUTHOR:Yamagata, S., Murakami, H., Terao, J., and Matsushita, S.
TITLE:Nonenzymatic Oxidation Products of Methyl Arachidonate
JOURNAL:Agric. Biol. Chem.
VOL:47 PAGE : 2791 -2799 (1983)
[TOP]

[8098]
AUTHOR:Terao, J.,And Matsushita, S.
TITLE:The Isomeric Compositions of Hydroperoxides Produced by Oxidation of Arachidonic Acid with Singlet Oxygen
JOURNAL:Agric. Biol. Chem.
VOL:45 PAGE : 587 -593 (1981)
[TOP]

[8103]
AUTHOR:Shimizu, T.
TITLE:A Recent Advance in Studies on Leukotriens (in Japanese)
JOURNAL:Taisha
VOL:24 PAGE : 203 -214 (1987)
[TOP]

[8104]
AUTHOR:Yamamoto, N.(1987) 1. A New Advance in Study on Prostaglandins, 2. Chemistry and Biochemistry, in An Advance in Recent Study on Prostaglandins, pp.1-86, Kodansha Scientific, Tokyo, Japan (in Japanese)
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[8108]
AUTHOR:Bild, G. S., Ramadoss, C. S., Lim, S., and Axelrod, B.
TITLE:Double dioxygenation of arachidonic acid by soybean lipoxygenase--1 PubMed ID:402916
JOURNAL:Biochem Biophys Res Commun.
VOL:74 PAGE : 949-954 (1977)
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.