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Eicosanoid


DATA No : XPR6002 INFORMANT : Shouzo Yamamoto

NAME : 12(S)-Hydroperoxy-5,8,10,14-(Z,Z,E,Z)-eicosatetraenoic acid

COMMON NAME:
SYMBOL: 12(S)-HPETE
FORMULA: C20H32O4 MOL.WT (average) : 336.466


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BIOLOGICAL ACTIVITY
There are reports for various biological activities of 12(S)-hydroperoxy acid such as neurotransmission, melatonin secretion, inhibition of platelet function and constriction of basilar artery, but a general theory has not been established (Ref. 0059/0060).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:DIETHYL ETHER (Ref. 1077), ETHYL ACETATE (Ref. 1078)
SPECTRAL DATA
UV SPECTRA:METHYL ESTER;l EtOHmax = 237nm (e 31,000) (Ref. 1081)

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS

METABOLISM
When arachidonic acid is allowed to react with 12-lipoxygenase, the predominant product is 12(S)-hydroperoxy-5,8,10,14-(Z,Z,E,Z)-eicosatetraenoic acid (Ref. 0059). The produced 12(S)-hydroperoxy acid is a precursor of hepoxilin (Ref. 0055).
GENETIC INFORMATION
cDNA and genomic DNA for 12-lipoxygenases were cloned (Ref. 0060).
NOTE

REFERENCES
[0055]
AUTHOR:Pace-Asciak, C. R.
TITLE:Hepoxilins: a review on their cellular actions PubMed ID:7947989
JOURNAL:Biochim Biophys Acta.
VOL:1215 PAGE : 1-8 (1994)
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[0059]
AUTHOR:Yamamoto, S., Suzuki, H., and Ueda, N.
TITLE:Arachidonate 12-lipoxygenases PubMed ID:9373619
JOURNAL:Prog Lipid Res.
VOL:36 PAGE : 23-41 (1997)
[TOP]

[0060]
AUTHOR:Yoshimoto, T., and Yamamoto, S.
TITLE:Arachidonate 12-lipoxygenase PubMed ID:8777566
JOURNAL:J Lipid Mediat Cell Signal.
VOL:12 PAGE : 195-212 (1995)
[TOP]

[1077]
AUTHOR:Porter,N.A., Logan,J. and Kontoyiannidou,V.
TITLE:Preparation and Purification of Arachidonic Acid Hydroperoxides of Biological Importance.
JOURNAL:J. Org. Chem.
VOL:44 PAGE : 3177 -3181 (1979)
[TOP]

[1078]
AUTHOR:Boeynaems, J. M., Brash, A. R., Oates, J. A., and Hubbard, W. C.
TITLE:Preparation and assay of monohydroxy-eicosatetraenoic acids PubMed ID:7004263
JOURNAL:Anal Biochem.
VOL:104 PAGE : 259-267 (1980)
[TOP]

[1081]
AUTHOR:Hamberg,M. and Samuelsson,B.
TITLE:Prostaglandin Endoperoxides. Novel Transformation of Arachidonic Acid in Human Platelets. PubMed ID:4215079
JOURNAL:Proc. Nat. Acad. Sci. USA
VOL:71 PAGE : 3400 -3404 (1974)
[TOP]

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