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Fatty acid


DATA No : DFA8136 INFORMANT : Tetsuyuki Kobayashi

NAME : 12R-hydroxy-5Z,8Z,10E,14Z-eicosatetraenoic acid

COMMON NAME:
SYMBOL: 12(R)-HETE
FORMULA: C20H32O3 MOL.WT (average) : 320.466


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BIOLOGICAL ACTIVITY
12(R)-HETE is the primary lipoxygenase product in invertebrates such as the sea urchin where it plays a role in reproduction physiology (Ref. 8161).1 12(R)-HETE has been isolated from several tissues in mammals, but it is controversial whether it is derived from cytochrome P450 or 12(R)-lipoxygenase metabolism, in some cases. 12(R)-HETE is a potent chemotactic factor exhibiting dose-dependent neutrophil chemotaxis with significant responses observed at doses as low as 10 -11 M (Ref. 8164). It produces neovascularization in rabbit corneas at 0.5
PHYSICAL AND CHEMICAL PROPERTIES
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SPECTRAL DATA
UV SPECTRA:lmax: 237nm e: 27,000

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
12(R)-HETE is produced by the action of 12(R)-lipoxygenase on arachidonic acid (Ref. 8161).
CHEMICAL SYNTHESIS

METABOLISM
12(R)-HETE is the predominant stereoisomer produced by psoriatic skin scales and rat liver microsomal cytochrome P-450 (Ref. 8165/8166).
GENETIC INFORMATION

NOTE

REFERENCES
[8161]
AUTHOR:Hawkins, D.J. and Brash, A.R.
TITLE:Eggs of the sea urchin, Strongylocentrotus Purpuratus, contain a prominent (11R) and (12R) lipoxygenase activity. PubMed ID:3108255
JOURNAL:J. Biol. Chem.
VOL:262 PAGE : 7629 -7634 (1987)
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[8164]
AUTHOR:Masferrer, J. L., Rimarachin, J. A., Gerritsen, M. E., Falck, J. R., Yadagiri, P., Dunn, M. W., and Laniado-Schwartzman, M.
TITLE:12(R)-hydroxyeicosatrienoic acid, a potent chemotactic and angiogenic factor produced by the cornea PubMed ID:1709873
JOURNAL:Exp Eye Res.
VOL:52 PAGE : 417-424 (1991)
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[8165]
AUTHOR:Woollard, P.M.
TITLE:Stereochemical difference between 12-hydroxy-5,8,10,14-eicosatetraenoic acid in platelets and psoriatic lesions. PubMed ID:3707572
JOURNAL:Biochem. Biophys. Res. Commun.
VOL:136 PAGE : 169 -176 (1986)
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[8166]
AUTHOR:Capdevila, J., Yadagiri, P., Manna, S., et al.
TITLE:Absolute configuration of the hydroxyeicosatetraenoic acids (HETEs) formed during catalytic oxygenation of arachidonic acid by microsomal cytochrome P-450. PubMed ID:3101677
JOURNAL:Biochem. Biophys. Res. Commun.
VOL:141 PAGE : 1007 -1011 (1986)
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[8167]
AUTHOR:Lagarde, M., Boutillon, M. M., Guichardant, M., Lellouche, J. P., Beaucourt, J. P., Vanhove, A., and Gree, R.
TITLE:Further studies on the anti-thromboxane A2 activity of monohydroxylated fatty acids PubMed ID:2735941
JOURNAL:Biochem Pharmacol.
VOL:38 PAGE : 1863-1864 (1989)
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[8168]
AUTHOR:Piomelli, D., Wang, J. K., Sihra, T. S., Nairn, A. C., Czernik, A. J., and Greengard, P.
TITLE:Inhibition of Ca2+/calmodulin-dependent protein kinase II by arachidonic acid and its metabolites PubMed ID:2554319
JOURNAL:Proc Natl Acad Sci U S A.
VOL:86 PAGE : 8550-8554 (1989)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.