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Fatty acid


DATA No : DFA8156 INFORMANT : Tetsuyuki Kobayashi

NAME : 5-oxo-6E,8Z,11Z,14Z-eicosatetraenoic acid

COMMON NAME:
SYMBOL: 5-OxoETE/5-KETE
FORMULA: C20H30O3 MOL.WT (average) : 318.450


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BIOLOGICAL ACTIVITY
It stimulates cytosolic calcium levels in neutrophils with an EC of 2 nM (Ref. 8194). 5-OxoETE selectively stimulates the migration and degranulation of eosinophils and activates the MAPK pathway in stimulated neutrophils (Ref. 8195/8196).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

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OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax: 279nm e: 22,100

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
5-OxoETE is a polyunsaturated keto acid formed by the oxidation of 5-HETE in human neutrophils (Ref. 8193).
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[8193]
AUTHOR:Powell, W.S., Gravelle, F., and Gravel, S.
TITLE:Metabolism of 5(S)-hydroxy-6,8,11,14-eicosatetraenoic acid and other 5(S)-hydroxyeicosanoids by a specific dehydrogenase in human polymorphonuclear leukocytes. PubMed ID:1326548
JOURNAL:J. Biol. Chem.
VOL:267 PAGE : 19233 -19241 (1992)
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[8194]
AUTHOR:Powell, W. S., Zhang, Y., and Gravel, S.
TITLE:Effects of phorbol myristate acetate on the synthesis of 5-oxo-6,8,11,14-eicosatetraenoic acid by human polymorphonuclear leukocytes PubMed ID:8142396
JOURNAL:Biochemistry.
VOL:33 PAGE : 3927-3933 (1994)
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[8195]
AUTHOR:O'Flaherty, J. T., Kuroki, M., Nixon, A. B., Wijkander, J., Yee, E., Lee, S. L., Smitherman, P. K., Wykle, R. L., and Daniel, L. W.
TITLE:5-Oxo-eicosatetraenoate is a broadly active, eosinophil-selective stimulus for human granulocytes PubMed ID:8683135
JOURNAL:J Immunol.
VOL:157 PAGE : 336-342 (1996)
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[8196]
AUTHOR:O'Flaherty, J. T., Kuroki, M., Nixon, A. B., Wijkander, J., Yee, E., Lee, S. L., Smitherman, P. K., Wykle, R. L., and Daniel, L. W.
TITLE:5-Oxo-eicosanoids and hematopoietic cytokines cooperate in stimulating neutrophil function and the mitogen-activated protein kinase pathway PubMed ID:8663432
JOURNAL:J Biol Chem.
VOL:271 PAGE : 17821-17828 (1996)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.