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Eicosanoid


DATA No : XPR5101 INFORMANT : Shouzo Yamamoto

NAME : 10-Hydroxy-11(R),12(S)-epoxyeicosa-5,8,14(Z,Z,Z)-trienoic acid

COMMON NAME: HEPOXILIN B3
SYMBOL: HxB3
FORMULA: C20H32O4 MOL.WT (average) : 336.466


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BIOLOGICAL ACTIVITY
Little has been described about the biological actvity of hepoxilin B3 except for its poteniation of glucose-dependent insulin secretion (Ref. 0055) and of bradykinin-induced increase of vascular permeability (Ref. 0057).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:ACETATE, METHYL ESTER ; [a]d-23=-10.9deg(C=0.11, CHLOROFORM) (Ref. 1073)

DENSITY:

SOLUBILITY:DIETHYL ETHER (Ref. 1071)
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:ACETATE METHYL ESTER ; n(CHLOROFORM) 2956, 1743, 1550, 1372, 1234, 1033, 999cm-1 (Ref. 1073)

NMR SPECTRA:ACETATE METHYL ESTER ; 1H-NMR(C6D6) : d 5.67(dd, J=9.2, 6.4Hz, 1H, 10-CH), 5.52, 5.46, 5.42, 5.35, 5.32, 3.36(s, 3H, OCH3), 2.95(m, 2H, 7-CH), 2.92(m, 1H, 11-CH), 2.86(ddd, J=7.4, 7.4, 2.1Hz, 1H, 12-CH), 2.30(ddd, J=14.8, 7.4, 7.4Hz, 1H, 13-CH), 2.18(ddd, J=14.8, 7.4, 7.4Hz, 1H, 13-CH), 2.12(t, J=7.4Hz, 2H, 2-CH), 1.98(dt, J=7.4, 7.4Hz, 2H, 4-CH), 1.92(dt, J=8.8, 8.8Hz, 2H, 16-CH), 1.65(s, 3H, COCH3), 1.60(tt, J=7.4, 7.4Hz, 2H, 3-CH), 1.25(m, 6H), 0.88(t, J=7.0Hz, 3H, 20-CH). (Ref. 1073) 13NMR(C6D6) : 134.22, 133.35, 130.17, 127.74, 124.31, 123.37, 70.86, 58.30, 55.71, 50.94, 33.30, 31.71, 29.66, 29.52, 27.59, 26.73, 25.00, 22.88, 20.53, 14.23 (Ref. 1073)

MASS SPECTRA:METHYL ESTER TMS ETHER ; m/e 311, 282, 269(base peak) (Ref. 1073)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Hepoxilin B3 together with hepoxilin A3 is produced from arachidonic acid or more directly from 12(S)-hydroperoxy-5,8,10,14-eicosatetraenoic acid in various animal tissues including brain, pineal gland, pancreas and skin (Ref. 0055).
CHEMICAL SYNTHESIS
(Ref. 1075)
[Table 0001]
METABOLISM
The presence of hepoxilin synthase was suggested by a finding that intact cells (skin) and tissue slices (brain hippocampus and pineal gland) transformed 12(S)-hydroperoxy-5,8,10,14-eicosatetraenoic acid to hepoxilins A3 and B3, but tissue boiling inhibited the hepoxilin production (Ref. 0056).
GENETIC INFORMATION

NOTE

REFERENCES
[0055]
AUTHOR:Pace-Asciak, C. R.
TITLE:Hepoxilins: a review on their cellular actions PubMed ID:7947989
JOURNAL:Biochim Biophys Acta.
VOL:1215 PAGE : 1-8 (1994)
[TOP]

[0056]
AUTHOR:Pace-Asciak, C. R., Reynaud, D., and Demin, P. M.
TITLE:Hepoxilins: a review on their enzymatic formation, metabolism and chemical synthesis PubMed ID:7769965
JOURNAL:Lipids.
VOL:30 PAGE : 107-114 (1995)
[TOP]

[0057]
AUTHOR:Wang,M.-M., Demin,P.M., and Pace-Asciak,C.R. (1996) Epimer-specific actions of hepoxilins A3 and B3 on PAF- and bradykinin-evoked vascular permeability in the rat skin in vivo. in Platelet-activating factor and related lipid mediators (Nigam,S. et al., eds.), pp239-241, Plenum Press, New York
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[1071]
AUTHOR:Pace-Asciak, C. R., Mizuno, K., and Yamamoto, S.
TITLE:Resolution by DEAE-cellulose chromatography of the enzymatic steps in the transformation of arachidonic acid into 8, 11, 12- and 10, 11, 12-trihydroxy-eicosatrienoic acid by the rat lung PubMed ID:6405454
JOURNAL:Prostaglandins.
VOL:25 PAGE : 79-84 (1983)
[TOP]

[1073]
AUTHOR:Moghaddam, M. F., Gerwick, W. H., and Ballantine, D. L.
TITLE:Discovery of the mammalian insulin release modulator, hepoxilin B3, from the tropical red algae Platysiphonia miniata and Cottoniella filamentosa PubMed ID:2180942
JOURNAL:J Biol Chem.
VOL:265 PAGE : 6126-6130 (1990)
[TOP]

[1075]
AUTHOR:Corey,E.J., Kang,J., Laguzza,B.C. and Jones, R.L.
TITLE:Total Synthesis of 12-(S)-10-Hydroxy-trans-11,12-epoxyeicosa-5,9,14-(Z)-Trienoic Acids, Metabolites of Arachidonic Acid in Mammalian Blood Platelets.
JOURNAL:Tetrah. Lett.
VOL:24 PAGE : 4913 -4916 (1983)
[TOP]

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