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Fatty acid


DATA No : DFA8131 INFORMANT : Tetsuyuki Kobayashi

NAME : 8S-hydroxy-5Z,9E,11Z,14Z-eicosatetraenoic acid

COMMON NAME:
SYMBOL: 8(S)-HETE
FORMULA: C20H32O3 MOL.WT (average) : 320.466


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BIOLOGICAL ACTIVITY
Both 8(S)- and 8(R)-HETEs activate mouse skin protein kinase C at a dose of 100mM(Ref. 8158). It activates mouse keratinocyte protein kinase C with an IC50 of 100mM (Ref. 8159). 8(S)-HETE also activates PPARa selectively at concentrations as low as 0.3mM (Ref. 8160).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax: 237nm e: 27,000

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
8(S)-HETE is a major lipoxygenase product in PMA-treated mouse epidermis (Ref. 8158).
CHEMICAL SYNTHESIS

METABOLISM
8(S)-HETE is synthesized from arachidonic acid by a 8(S)-lipoxygenase present in phorbol ester-treated mouse skin (Ref. 8158).
GENETIC INFORMATION

NOTE

REFERENCES
[8158]
AUTHOR:Hughes, M. A., and Brash, A. R.
TITLE:Investigation of the mechanism of biosynthesis of 8-hydroxyeicosatetraenoic acid in mouse skin PubMed ID:1900207
JOURNAL:Biochim Biophys Acta.
VOL:1081 PAGE : 347-354 (1991)
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[8159]
AUTHOR:Lo, H. H., Bartek, G. A., and Fischer, S. M.
TITLE:In vitro activation of mouse skin protein kinase C by fatty acids and their hydroxylated metabolites PubMed ID:7990661
JOURNAL:Lipids.
VOL:29 PAGE : 547-553 (1994)
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[8160]
AUTHOR:Yu, K., Bayona, W., Kallen, C. B., Harding, H. P., Ravera, C. P., McMahon, G., Brown, M., and Lazar, M. A.
TITLE:Differential activation of peroxisome proliferator-activated receptors by eicosanoids PubMed ID:7592593
JOURNAL:J Biol Chem.
VOL:270 PAGE : 23975-23983 (1995)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.