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Eicosanoid


DATA No : XPR2102 INFORMANT : Shouzo Yamamoto

NAME : 7-[Tetrahydro-4(S),6-dihydroxy-2(R)-(3(S)-hydroxy-1(E),5(Z)-octadienyl)-2H-pyran-3(S)-yl]-5(Z)-heptenoic acid

COMMON NAME: THROMBOXANE B3
SYMBOL: TXB3
FORMULA: C20H32O6 MOL.WT (average) : 368.464


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:DIETHYL ETHER (Ref. 1118), ETHYL ACETATE, CHLOROFORM (Ref. 1119)
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:FILM : n 3392, 3010, 2932, 1713, 1407, 1363, 1231, 1154, 1104, 1024, 973, 895 cm-1 (Ref. 1119)

NMR SPECTRA:1H-NMR(CDCl3, TMS) : d 5.85(dd, J=17.5, 6.3Hz,1H, 14-CH), 5.71(dd, J=17.5, 7.5Hz, 1H, 13-CH), 5.55(td, J=20.0, 12.5Hz, 1H, 18-CH), 5.48-5.31(m, 4H, 5,6,11,17-CH), 4.41(dd, J=12.5, 7.5Hz, 1H, 12-CH), 4.23(dt, J=12.5, 6.3Hz, 1H, 15-CH), 4.08(m, 1H, 9-CH), 2.40-2.24(m, 4H, 4,16-CH), 2.18-1.96(m, 7H, 2,7,10,19-CH), 1.81(m, 2H, 3-CH), 1.74-1.63(m, 2H, 3-CH), 1.45(tdd, J=8.8, 5.0, 5.0Hz, 1H, 8-CH), 0.96(t, J=7.5Hz, 3H, 20-CH) (Ref. 1119) 13C-NMR(CDCl3) : 177.25, 136.52, 135.22, 130.75, 129.22, 127.49, 123.66, 123.59, 92.56, 71.58, 69.20, 64.95, 44.99, 36.01, 34.72, 32.89, 26.31, 24.80, 24.58, 24.58, 20.76, 14.21(Ref. 1119)

MASS SPECTRA:FAB : m/e 351(M+1-H2O), 333, 315, 307 (Ref. 1119)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS
(Ref. 1119)
[Table 0001]
METABOLISM
Prostaglandin H3 is produced from 5,8,11,14,17-eicosapentaenoic acid by the catalysis of fatty acid cyclooxygenase, and then transformed to unstable thromboxane A3 (Ref. 0090), which is converted non-enzymatically to stable thromboxane B3.
GENETIC INFORMATION

NOTE

REFERENCES
[0090]
AUTHOR:Needleman, P., Raz, A., Minkes, M. S., Ferrendelli, J. A., and Sprecher, H.
TITLE:Triene prostaglandins: prostacyclin and thromboxane biosynthesis and unique biological properties PubMed ID:218223
JOURNAL:Proc Natl Acad Sci U S A.
VOL:76 PAGE : 944-948 (1979)
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[1118]
AUTHOR:Hamberg, M.
TITLE:Transformations of 5,8,11,14,17-eicosapentaenoic acid in human platelets PubMed ID:6249377
JOURNAL:Biochim Biophys Acta.
VOL:618 PAGE : 389-398 (1980)
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[1119]
AUTHOR:Nakamura,N., Nagai,H., Yoneda,M., Suga,H., Kawamura,M. and Iguchi,S.
TITLE:Synthesis of Thromboxane B3 and Its Direct Separation from Thromboxane B2 by Reversed-Phase High Performance Liquid Chromatography.
JOURNAL:Chem. Pham. Bull.
VOL:41 PAGE : 1769 -1773 (1993)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.