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	:	95-96C (Ref. 1033)

BOILING POINT	:

REFRACTIVE INDEX	:

OPTICAL ROTATION	:	[a]=57.4(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)

[TOP]

[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)

[TOP]

[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)

[TOP]