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Eicosanoid


DATA No : XPR2101 INFORMANT : Shouzo Yamamoto

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

COMMON NAME: THROMBOXANE B2
SYMBOL: TXB2
FORMULA: C20H34O6 MOL.WT (average) : 370.480


Download ChemDraw structure data
BIOLOGICAL ACTIVITY
Thromboxane B2 as s stable degradation product of thromboxane A2 shows diminishd biological activity (Ref. 0014).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:95-96degC (Ref. 1033)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-25=57.4deg(C=0.26 ETHYL ACETATE) (Ref. 1033)

DENSITY:

SOLUBILITY:ETHYL ACETATE (Ref. 1035)
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:FILM: n 3380, 1705cm-1 (Ref. 1033)

NMR SPECTRA:1H-NMR(CDCl3) : d 5.86(m, 1H, 14-CH), 5.72(m, 1H, 13-CH), 5.46(m, 2H, 5,6-CH), 5.35 and 5.23(m, 1H, 11-CH), 4.41(m, 1H, 12-CH), 4.22(m, 1H, 15-CH), 4.11(m, 1H, 9-CH), 2.35(t, 2H, 2-CH2), 0.89(m, 3H, 20-CH3) (Ref. 1034)

MASS SPECTRA:m/e 335, 317 (Ref. 1033)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Thromboxane B2 as a stable degradation product of bioactive but unstable thromboxane A2 is detected in the tissue where thromboxane A2 is produced (Ref. 0013).
CHEMICAL SYNTHESIS
(Ref. 1033)
[Table 0001]
METABOLISM
The major urinary metabolite of tromboxane B2 is 2,3-dinor-thromboxane B2 (Ref. 0031), and 11-dehydro-thromboxane B2 is known as a suitble parameter for monitoring thromboxane production in human (Ref. 0032). 11-Hydroxythromboxane B2 dehydrogenase responsible for the 11-dehydro-thromboxane B2 production was identified as cytosolic aldehyde dehydrogenase (Ref. 0034).
GENETIC INFORMATION

NOTE

REFERENCES
[0013]
AUTHOR:Moncada, S., and Vane, J. R.
TITLE:Pharmacology and endogenous roles of prostaglandin endoperoxides, thromboxane A2, and prostacyclin PubMed ID:116251
JOURNAL:Pharmacol Rev.
VOL:30 PAGE : 293-331 (1978)
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[0014]
AUTHOR:Whittle, B. J., and Moncada, S.
TITLE:Pharmacological interactions between prostacyclin and thromboxanes PubMed ID:6313114
JOURNAL:Br Med Bull.
VOL:39 PAGE : 232-238 (1983)
[TOP]

[0031]
AUTHOR:Kindahl,H.
TITLE:Metabolism of thromboxane B2 in the cynomolgus monkey. PubMed ID:404670
JOURNAL:Prostaglandins
VOL:13 PAGE : 619 -629 (1997)
[TOP]

[0032]
AUTHOR:Westlund, P., Granstrom, E., Kumlin, M., and Nordenstrom, A.
TITLE:Identification of 11-dehydro-TXB2 as a suitable parameter for monitoring thromboxane production in the human PubMed ID:3755250
JOURNAL:Prostaglandins.
VOL:31 PAGE : 929-960 (1986)
[TOP]

[0034]
AUTHOR:Westlund, P., Fylling, A. C., Cederlund, E., and Jornvall, H.
TITLE:11-Hydroxythromboxane B2 dehydrogenase is identical to cytosolic aldehyde dehydrogenase PubMed ID:8200461
JOURNAL:FEBS Lett.
VOL:345 PAGE : 99-103 (1994)
[TOP]

[1033]
AUTHOR:Hanessian,S., and Lavallee,P.
TITLE:A Stereospecific, Total Synthesis of Thromboxane B2.
JOURNAL:Can. J. Chem.
VOL:55 PAGE : 562 -565 (1977)
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[1034]
AUTHOR:Kotovych,G., and Aarts,G.H.M.
TITLE:A High Field Proton Magnetic Resonance Study of the Solution Conformation of Thromboxane B2.
JOURNAL:Can. J. Chem.
VOL:58 PAGE : 1111 -1117 (1980)
[TOP]

[1035]
AUTHOR:Kelly,R.C., Schletter,I., and Stein,S.J.
TITLE:Synthesis of Thromboxane B2.
JOURNAL:Tetrah. Lett.
VOL: PAGE : 3279 -3282 (1976)
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