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Eicosanoid


DATA No : XPR6102 INFORMANT : Shouzo Yamamoto

NAME : 12(S)-Hydoxy-5,8,10,14-(Z,E,Z,Z)-eicosatetraenoic acid

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


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BIOLOGICAL ACTIVITY
There are reports for various biological activities of 12(S)-hydroxy acid such as rat hypothalamic secretion of LH-RH, stimulated chemotactic activity of human eosinophils and neutrophils, stimulated migration of epidermal tumor cells and rat aortic smooth muscle cells, involvement in angiotension II-mediated aldosterone biosynthesis in human adrenal glomerulosa, and expression or activation of GpIIb/IIIa in tumor cells, but a general theory has not been established (Ref. 0059/0060).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:METHYL ESTER ; [a]d-25=+1.50deg(C=0.2, CHLOROFORM) (Ref. 1082), [a]d-22=+13deg(C=1.5, ACETONE) (Ref. 1083)

DENSITY:

SOLUBILITY:DIETHYL ETHER , ACETONE , BENZENE (Ref. 1083)
SPECTRAL DATA
UV SPECTRA:METHYL ESTER ; l MeOHmax = 234nm (Ref. 1084)METHYL ESTER ; l EtOHmax = 237nm(e 30500) (Ref. 1081)

IR SPECTRA:NEAT : n 3480b, 1710, 1460, 1400cm-1 (Ref. 1083)

NMR SPECTRA:1H-NMR(250MHz, ACETONE-D6) ; d 6.58(dd, J=15.3, 11.0Hz, 1H, 10-CH), 5.97(t, J=11.0Hz, 1H, 9-CH), 5.72(dd, J=15.3, 6.2 Hz, 1H, 11-CH), 5.29(m, 5H, 5,6,8,14,15-CH), 4.16(q, J=6.3Hz, 1H, 12-CH), 2.94(t, J=6.1Hz, 2H, 7-CH), 2.27(t,J= 7.4Hz, 2H,2-CH), 2.22(m, 2H, 13-CH), 1.66 and 2.14(m, 2H, 4-and 16-CH), 0.87(t, J=6.3Hz, 3H, 20-CH) (Ref. 1083). 13NMR(C6D6) : 174.3, 137.77, 132.02, 129.98, 129.62, 128.88, 128.69, 125.96, 124.44 (Ref. 1083)

MASS SPECTRA:METHYL ESTER ; m/e 316, 303, 223, 191, 141, 107(base peak) (Ref. 1084)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS
(Ref. 1082)
[Table 0001]
METABOLISM
When arachidonic acid is oxygenated by 12-lipoxygenase, 12(S)-hydroperoxy-5,8,10,14-(Z,Z,E,Z)-eicosatetraenoic acid is produced (Ref. 0059). The latter compound is reduced to a corresponding 12(S)-hydroxy acid with whole cells or crude enzyme preparations.
GENETIC INFORMATION

NOTE

REFERENCES
[0059]
AUTHOR:Yamamoto, S., Suzuki, H., and Ueda, N.
TITLE:Arachidonate 12-lipoxygenases PubMed ID:9373619
JOURNAL:Prog Lipid Res.
VOL:36 PAGE : 23-41 (1997)
[TOP]

[0060]
AUTHOR:Yoshimoto, T., and Yamamoto, S.
TITLE:Arachidonate 12-lipoxygenase PubMed ID:8777566
JOURNAL:J Lipid Mediat Cell Signal.
VOL:12 PAGE : 195-212 (1995)
[TOP]

[1081]
AUTHOR:Hamberg,M. and Samuelsson,B.
TITLE:Prostaglandin Endoperoxides. Novel Transformation of Arachidonic Acid in Human Platelets. PubMed ID:4215079
JOURNAL:Proc. Nat. Acad. Sci. USA
VOL:71 PAGE : 3400 -3404 (1974)
[TOP]

[1082]
AUTHOR:Corey,E.J., Niwa,H. and Knolle,J.
TITLE:Total Synthesis of (S)-12-Hydroxy-5,8,14-cis-10-trans-eicosatetraenoic Acid (Samuelsson's HETE).
JOURNAL:J. Am. Chem. Soc.
VOL:100 PAGE : 1942 -1943 (1978)
[TOP]

[1083]
AUTHOR:Leblanc,Y., Fitzsimmons,B.J., Adams,J., Perez,F. and Rokach,J.
TITLE:The Total Synthesis of 12-HETE and 12,20-DiHETE.
JOURNAL:J. Org. Chem.
VOL:51 PAGE : 789 -793 (1986)
[TOP]

[1084]
AUTHOR:Just,G. and Wang,Z.Y.
TITLE:Total Synthesis of 8(S)-, 9(S)-, 11(S)-, and 12(S)-HETE Methyl Esters.
JOURNAL:J. Org. Chem.
VOL:51 PAGE : 4796 -4802 (1986)
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.