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Eicosanoid


DATA No : XPR6114 INFORMANT : Shouzo Yamamoto

NAME : (R),(Z,E,Z,Z)-8-Hydroxy-5,9,11,14-eicosatetraenoic acid

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


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BIOLOGICAL ACTIVITY
The compound is involved in the maturation of starfish oocyte (Ref. 0074).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:8(S)-ISOMER METHYL ESTER ; [a]d-22=-4.75deg(C=0.4, CHLOROFORM) (Ref. 1091)

DENSITY:

SOLUBILITY:ETHYL ACETATE (Ref. 1092)
SPECTRAL DATA
UV SPECTRA:METHYL ESTER ; l max = 235.8nm (e 28,000)(Ref. 1092)

IR SPECTRA:

NMR SPECTRA:8(S)-ISOMER METHYL ESTER ; 1H-NMR(CDCl3) : d 6.56(dd, J=14.5, 11.1Hz, 1H, 10-CH), 6.00(brt, J=11.1, 9.7Hz, 1H, 11-CH), 5.72(dd, J=7.3, 14.5Hz, 1H, 9-CH), 5.59-5.16(m, 5H), 4.23(q, 1H,8-CH), 3.71(s, 3H,OCH3), 2.95(t, 2H,13-CH), 2.35(t, 4H, 4,7-CH), 2.11(sextet, 4H), 1.73(pentet, 2H, 3-CH), 1.56(brs, S, 1H, OH), 1.32(m, 6H), 0.91(t, 3H, 20-CH) (Ref. 1091)

MASS SPECTRA:METHYL ESTER, TMS ETHER ; m/e 265 (Ref. 1092). 8(S)-ISOMER METHYL ESTER TMS ETHER ; m/e 406, 391, 316, 265, 243 (Ref. 1091)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS
(Ref. 1091)
[Table 0001]
METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0074]
AUTHOR:Meijer,L., Brash,A.R., Bryant,R.W., Ng,K., Maclouf,J., and Sprecher,H.
TITLE:Stereospecific induction of starfish oocyte maturation by (8R)-hydroxyeicosatetraenoic acid. PubMed ID:3097019
JOURNAL:J. Biol. Chem.
VOL:261 PAGE : 17040 -17047 (1986)
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[1091]
AUTHOR:Yadagiri,P., Lumin,S., Mosset,P., Capdevila,J. and Falck,J.R.
TITLE:Enantiospecific Total Synthesis of 8- and 12-Hydroxyeicosatetraenoic Acid.
JOURNAL:Tetrah. Lett.
VOL:27 PAGE : 6039 -6040 (1986)
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[1092]
AUTHOR:Bundy, G. L., Nidy, E. G., Epps, D. E., Mizsak, S. A., and Wnuk, R. J.
TITLE:Discovery of an arachidonic acid C-8 lipoxygenase in the gorgonian coral Pseudoplexaura porosa PubMed ID:2867091
JOURNAL:J Biol Chem.
VOL:261 PAGE : 747-751 (1986)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.