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Eicosanoid


DATA No : XPR2121 INFORMANT : Shouzo Yamamoto

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

COMMON NAME: 11-DEHYDROTHROMBOXANE B2
SYMBOL: 11-DEHYDRO-TXB2
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:METHANOL, ETHYL ACETATE (Ref. 1058)
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:METHYL ESTER ; CHLOROFORM solution, n 1730 cm-1 (Ref. 1057)

NMR SPECTRA:METHYL ESTER ; 1H-NMR(CDCl3) : d 5.86-5.78(m, 2H), 5.56-5.32(m, 2H), 5.13-4.72(m, 1H), 5.23-4.05(m, 2H), 3.67(S, 3H, OCH3)(Ref. 1057)

MASS SPECTRA:METHYL ESTER BIS-TMS ETHER ; m/e 526(M+), 511, 455, 370, 295 (Ref. 1057)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
When thromboxane B2 is infused, 11-dehydro-thromboxane B2 is found as a major metabolite in the blood of rabbit (Ref. 0049) and man (Ref. 0032). The compound appears in urine as one of the mejor metabolites (Ref. 0032/0049).
CHEMICAL SYNTHESIS

METABOLISM
11-Hydroxythromboxane B2 dehydrogenase is considered to be the enzyme responsible for 11-dehydro-thromboxane B2 production (Ref. 0034).
GENETIC INFORMATION

NOTE

REFERENCES
[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)
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[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)
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[0049]
AUTHOR:Westlund, P., Kumlin, M., Nordenstrom, A., and Granstrom, E.
TITLE:Circulating and urinary thromboxane B2 metabolites in the rabbit: 11-dehydro-thromboxane B2 as parameter of thromboxane production PubMed ID:3520685
JOURNAL:Prostaglandins.
VOL:31 PAGE : 413-443 (1986)
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[1057]
AUTHOR:Nelson, N. A., Jackson, R. W., and Sebek, O. K.
TITLE:Synthesis of thromboxane B2 metabolites PubMed ID:704927
JOURNAL:Prostaglandins.
VOL:16 PAGE : 85-92 (1978)
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[1058]
AUTHOR:Roberts, L. J., 2nd, Sweetman, B. J., and Oates, J. A.
TITLE:Metabolism of thromboxane B2 in the monkey PubMed ID:97291
JOURNAL:J Biol Chem.
VOL:253 PAGE : 5305-5318 (1978)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.