Taurocholic acid

Taurocholic acid
Names
	IUPAC name 2-{[(3α,5β,7α,12α)-3,7,12-trihydroxy-24-oxocholan-24-yl]amino}ethanesulfonic acid
Identifiers
CAS Number	81-24-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28865 ;
ChEMBL	ChEMBL224867 ;
ChemSpider	6423 ;
ECHA InfoCard	100.001.216
IUPHAR/BPS	4547;
PubChem CID	6675;
UNII	5E090O0G3Z ;
CompTox Dashboard (EPA)	DTXSID00883259 ;
	InChI 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 Key: WBWWGRHZICKQGZ-HZAMXZRMSA-N ; 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;
	SMILES 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
Chemical formula	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).
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	Infobox references

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.

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.
Taurocholic acid, sodium salt Archived 2009-04-21 at the Wayback Machine at GlycoFineChem.com

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