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Eicosanoid


DATA No : XPR6101 INFORMANT : Shouzo Yamamoto

NAME : 5(S)-Hydroxy-6,8,11,14-(E,Z,Z,Z)-eicosatetraenoic acid

COMMON NAME:
SYMBOL: 5(S)-HETE
FORMULA: C20H32O2 MOL.WT (average) : 304.467


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:METHYL ESTER ; [a]d-23=+14.0deg(C=2.0, BENZENE) (Ref. 1079)

DENSITY:

SOLUBILITY:DIETHYL ETHER (Ref. 1080)
SPECTRAL DATA
UV SPECTRA:METHYL ESTER ; l MeOHmax = 235nm (e 30,500) (Ref. 1080)

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:METHYL ESTER ETHER ; m/e 406(M+), 391, 375, 316, 305, 255, 216, 215, 203, 190, 155, 150, 143, 136, 105, 80, 79 (Ref. 1080)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS
(Ref. 1079)
[Table 0001]
METABOLISM
When arachidonic acid is oxygenated by 5-lipoxygenase, 5(S)-hydroperoxy-6,,8,11,14-(E,Z,Z,Z)-eicosatetraenoic acid is produced (Ref. 0025). The latter compound is reduced to a corresponding 5(S)-hydroxy acid with whole cells or crude enzyme preparations.
GENETIC INFORMATION

NOTE

REFERENCES
[0025]
AUTHOR:Ford-Hutchinson, A. W., Gresser, M., and Young, R. N.
TITLE:5-Lipoxygenase PubMed ID:7979243
JOURNAL:Annu Rev Biochem.
VOL:63 PAGE : 383-417 (1994)
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[1079]
AUTHOR:Corey,E.J. and Hashimoto,S.
TITLE:A Practical Process for Large-Scale Synthesis of (S)-5-Hydroxy-6-trans-8,11,14-cis-eicosatetraenoic Acid (5-HETE).
JOURNAL:Tetrah. Lett.
VOL:22 PAGE : 299 -302 (1981)
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[1080]
AUTHOR:Borgeat,P., Hamberg,M. and Samuelsson,B.
TITLE:Transformation of Arachidonic Acid and Homo-g-linolenic Acid by Rabbit Polymorphonuclear Leukocytes. Monohydroxy Acids from Novel Lipoxygenases. PubMed ID:826538
JOURNAL:J. Biol. Chem.
VOL:251 PAGE : 7816 -7820 (1976)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.