Jump to content

Taurocholic acid

From Wikipedia, the free encyclopedia

This is an old revision of this page, as edited by Fswitzer4 (talk | contribs) at 13:22, 3 June 2020 (Added FDA UNII). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Taurocholic acid
Taurocholic acid
Names
IUPAC name
2-{[(3α,5β,7α,12α)-3,7,12-trihydroxy-24-oxocholan-24-yl]amino}ethanesulfonic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.216 Edit this at Wikidata
UNII
  • InChI=1S/C26H45NO7S/c1-15(4-7-23(31)27-10-11-35(32,33)34)18-5-6-19-24-20(14-22(30)26(18,19)3)25(2)9-8-17(28)12-16(25)13-21(24)29/h15-22,24,28-30H,4-14H2,1-3H3,(H,27,31)(H,32,33,34)/t15-,16+,17-,18-,19+,20+,21-,22+,24+,25+,26-/m1/s1 checkY
    Key: WBWWGRHZICKQGZ-HZAMXZRMSA-N checkY
  • InChI=1/C26H45NO7S/c1-15(4-7-23(31)27-10-11-35(32,33)34)18-5-6-19-24-20(14-22(30)26(18,19)3)25(2)9-8-17(28)12-16(25)13-21(24)29/h15-22,24,28-30H,4-14H2,1-3H3,(H,27,31)(H,32,33,34)/t15-,16+,17-,18-,19+,20+,21-,22+,24+,25+,26-/m1/s1
    Key: WBWWGRHZICKQGZ-HZAMXZRMBW
  • C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)O)C
Properties
C26H45NO7S
Molar mass 515.7058 g/mol
Melting point 125.0 °C (257.0 °F; 398.1 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Taurocholic acid, known also as cholaic acid, cholyltaurine, or acidum cholatauricum, is a deliquescent yellowish crystalline bile acid involved in the emulsification of fats. It occurs as a sodium salt in the bile of mammals. It is a conjugate of cholic acid with taurine. In medical use, it is administered as a cholagogue and choleretic.[1]

Hydrolysis of taurocholic acid yields taurine.

For commercial use, taurocholic acid is manufactured from cattle bile, a byproduct of the meat-processing industry.[2]

This acid is also one of the many molecules in the body that has cholesterol as its precursor.

Toxicity

The median lethal dose of taurocholic acid in newborn rats is 380 mg/kg.

See also

References

  1. ^ Anwer, M. Sawkat (2004). "Cellular regulation of hepatic bile acid transport in health and cholestasis". Hepatology. 39 (3): 581–590. doi:10.1002/hep.20090. PMID 14999673.
  2. ^ Taurocholic acid, sodium salt Archived 2009-04-21 at the Wayback Machine at GlycoFineChem.com