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 ^E^t^O^H_m_a_x = 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)

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[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)

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[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)

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[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)

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[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)

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