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{{Lipid/Header}}
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|LipidBank=XPR2101
|LipidBank=XPR2101
|LipidMaps=LMFA03030002
|LipidMaps=LMFA03030002
|SysName=7- [ Tetrahydro-4 (S) ,6-dihydroxy-2 (R) - (3 (S) -hydroxy-1 (E) -octenyl) -2H-pyran-3 (S) -yl ] -5 (Z) -heptenoic acid
|SysName=7- [Tetrahydro- (4S,6) -dihydroxy-2 R- (3S-hydroxy-trans-1-octenyl) -2H-pyran-3S-yl] -cis-5-heptenoic acid
|Common Name=&&THROMBOXANE B2&&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&&7- [ Tetrahydro-4 (S) ,6-dihydroxy-2 (R) - (3 (S) -hydroxy-1 (E) -octenyl) -2H-pyran-3 (S) -yl ] -5 (Z) -heptenoic acid&&
|Melting Point=95-96°C [[Reference:Hanessian_S:Lavallee_P:,Can. J. Chem.,1977,55,562|{{RelationTable/GetFirstAuthor|Reference:Hanessian_S:Lavallee_P:,Can. J. Chem.,1977,55,562}}]]
|Melting Point=95-96°C [[Reference:Hanessian_S:Lavallee_P:,Can. J. Chem.,1977,55,562|{{RelationTable/GetFirstAuthor|Reference:Hanessian_S:Lavallee_P:,Can. J. Chem.,1977,55,562}}]]
|Reflactive=[<FONT FACE="Symbol">a</FONT>]X<sub>D</sub><sup>25</sup>=57.4°(C=0.26 ETHYL ACETATE) [[Reference:Hanessian_S:Lavallee_P:,Can. J. Chem.,1977,55,562|{{RelationTable/GetFirstAuthor|Reference:Hanessian_S:Lavallee_P:,Can. J. Chem.,1977,55,562}}]]
|Optical=[ alpha ]^{25}_D =57.4°(C=0.26 ETHYL ACETATE) [[Reference:Hanessian_S:Lavallee_P:,Can. J. Chem.,1977,55,562|{{RelationTable/GetFirstAuthor|Reference:Hanessian_S:Lavallee_P:,Can. J. Chem.,1977,55,562}}]]
|Solubility=ETHYL ACETATE  
|Solubility=ETHYL ACETATE [[Reference:Kelly RW:Schletter_I:Stein_SJ:,Tetrahedron_Lett.,1976,,3279|{{RelationTable/GetFirstAuthor|Reference:Kelly RW:Schletter_I:Stein_SJ:,Tetrahedron_Lett.,1976,,3279}}]]
|Mass Spectra=m/e 335, 317 [[Reference:Hanessian_S:Lavallee_P:,Can. J. Chem.,1977,55,562|{{RelationTable/GetFirstAuthor|Reference:Hanessian_S:Lavallee_P:,Can. J. Chem.,1977,55,562}}]]
|Mass Spectra=m/e 335, 317 [[Reference:Hanessian_S:Lavallee_P:,Can. J. Chem.,1977,55,562|{{RelationTable/GetFirstAuthor|Reference:Hanessian_S:Lavallee_P:,Can. J. Chem.,1977,55,562}}]]
|IR Spectra=FILM: <FONT FACE="Symbol">n</FONT> 3380, 1705cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP> [[Reference:Hanessian_S:Lavallee_P:,Can. J. Chem.,1977,55,562|{{RelationTable/GetFirstAuthor|Reference:Hanessian_S:Lavallee_P:,Can. J. Chem.,1977,55,562}}]]
|IR Spectra=FILM: nu  3380, 1705cm^{-1} [[Reference:Hanessian_S:Lavallee_P:,Can. J. Chem.,1977,55,562|{{RelationTable/GetFirstAuthor|Reference:Hanessian_S:Lavallee_P:,Can. J. Chem.,1977,55,562}}]]
|NMR Spectra=<SUP><FONT SIZE=-1>1</FONT></SUP>H-NMR(CDCl<SUB><FONT SIZE=-1>3</FONT></SUB>) : <FONT FACE="Symbol">d</FONT> 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-CH<SUB><FONT SIZE=-1>2</FONT></SUB>), 0.89(m, 3H, 20-CH<SUB><FONT SIZE=-1>3</FONT></SUB>) [[Reference:Kotovych_G:Aarts_GHM:,Can. J. Chem.,1980,58,1111|{{RelationTable/GetFirstAuthor|Reference:Kotovych_G:Aarts_GHM:,Can. J. Chem.,1980,58,1111}}]]
|NMR Spectra=^1 H-NMR(CDCl_3 ) : delta  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-CH_2 ), 0.89(m, 3H, 20-CH_3 ) [[Reference:Kotovych_G:Aarts_GHM:,Can. J. Chem.,1980,58,1111|{{RelationTable/GetFirstAuthor|Reference:Kotovych_G:Aarts_GHM:,Can. J. Chem.,1980,58,1111}}]]
|Source=Thromboxane B2 as a stable degradation product of bioactive but unstable thromboxane A2 is detected in the tissue where thromboxane A2 is produced [[Reference:Moncada_S:Vane_JR:,Pharmacol. Rev.,1978,30,293|{{RelationTable/GetFirstAuthor|Reference:Moncada_S:Vane_JR:,Pharmacol. Rev.,1978,30,293}}]].
|Chemical Synthesis=[[Reference:Hanessian_S:Lavallee_P:,Can. J. Chem.,1977,55,562|{{RelationTable/GetFirstAuthor|Reference:Hanessian_S:Lavallee_P:,Can. J. Chem.,1977,55,562}}]] {{Image200|LBF20207TX02FT0001.gif}}
|Metabolism=The major urinary metabolite of tromboxane B2 is 2,3-dinor-thromboxane B2 [[Reference:Kindahl_H:,Prostaglandins,1977,13,619|{{RelationTable/GetFirstAuthor|Reference:Kindahl_H:,Prostaglandins,1977,13,619}}]], and 11-dehydro-thromboxane B2 is known as a suitble parameter for monitoring thromboxane production in human [[Reference:Westlund_P:Granstrom_E:Kumlin_M:Nordenstrom_A:,Prostaglandins,1986,31,929|{{RelationTable/GetFirstAuthor|Reference:Westlund_P:Granstrom_E:Kumlin_M:Nordenstrom_A:,Prostaglandins,1986,31,929}}]]. 11-Hydroxythromboxane B2 dehydrogenase responsible for the 11-dehydro-thromboxane B2 production was identified as cytosolic aldehyde dehydrogenase [[Reference:Westlund_P:Fylling_AC:Cederlund_E:Jornvall_H:,FEBS Lett.,1994,345,99|{{RelationTable/GetFirstAuthor|Reference:Westlund_P:Fylling_AC:Cederlund_E:Jornvall_H:,FEBS Lett.,1994,345,99}}]].
|Symbol=TXB2
|Biological Activity=Thromboxane B2 as s stable degradation product of thromboxane A2 shows diminishd biological activity [[Reference:Whittle_BJ:Moncada_S:,Br. Med. Bull.,1983,39,232|{{RelationTable/GetFirstAuthor|Reference:Whittle_BJ:Moncada_S:,Br. Med. Bull.,1983,39,232}}]].
}}
 
{{MassbankSpectra|
UT000370
UT000371
UT000372
UT000373
UT000374
UT000375
UT000376
UT000377
UT000378
}}
}}
{{Lipid/Footer}}

Latest revision as of 00:00, 17 January 2014

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Upper classes: LB LBF



IDs and Links
LipidBank XPR2101
LipidMaps LMFA03030002
CAS
KEGG {{{KEGG}}}
KNApSAcK {{{KNApSAcK}}}
mol LBF20207TX02
Thromboxane B2
LBF20207TX02.png
Structural Information
7- [Tetrahydro- (4S,6) -dihydroxy-2 R- (3S-hydroxy-trans-1-octenyl) -2H-pyran-3S-yl] -cis-5-heptenoic acid
  • Thromboxane B2
  • 7- [ Tetrahydro-4 (S) ,6-dihydroxy-2 (R) - (3 (S) -hydroxy-1 (E) -octenyl) -2H-pyran-3 (S) -yl ] -5 (Z) -heptenoic acid
 TXB2
Formula C20H34O6
Exact Mass 370.23553882
Average Mass 370.48036
SMILES C(CC[C@H](O)C=C[C@@H](O1)[C@@H]([C@@H](CC1O)O)CC=CCCCC(O)=O)CC
Physicochemical Information
95-96°C Hanessian_S et al.
[ α ]25
D   =57.4°(C=0.26 ETHYL ACETATE) HanessianSet al.
ETHYL ACETATE Kelly RW et al.
Thromboxane B2 as a stable degradation product of bioactive but unstable thromboxane A2 is detected in the tissue where thromboxane A2 is produced Moncada_S et al..
Hanessian_S et al.
LBF20207TX02FT0001.gif
 The major urinary metabolite of tromboxane B2 is 2,3-dinor-thromboxane B2 Kindahl_H , and 11-dehydro-thromboxane B2 is known as a suitble parameter for monitoring thromboxane production in human Westlund_P et al.. 11-Hydroxythromboxane B2 dehydrogenase responsible for the 11-dehydro-thromboxane B2 production was identified as cytosolic aldehyde dehydrogenase Westlund_P et al..
Thromboxane B2 as s stable degradation product of thromboxane A2 shows diminishd biological activity Whittle_BJ et al..
Spectral Information
Mass Spectra m/e 335, 317 HanessianSet al.
UV Spectra
IR Spectra FILM: ν 3380, 1705cm-1 HanessianSet al.
NMR Spectra 1H-NMR(CDCl3) : δ 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) KotovychGet al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20207TX02 See above. Hanessian_S et al. 1977
n.a. LBF20207TX02 See above. Kelly_RW et al. 1976
n.a. LBF20207TX02 See above. Kindahl_H 1977
n.a. LBF20207TX02 See above. Kotovych_G et al. 1980
n.a. LBF20207TX02 See above. Moncada_S et al. 1978
n.a. LBF20207TX02 See above. Westlund_P et al. 1994
n.a. LBF20207TX02 See above. Westlund_P et al. 1986



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