{{Short description|Yellowish crystalline bile acid}} {{chembox | verifiedrevid = 470481809 | Name = Taurocholic acid | ImageFile_Ref = {{chemboximage|correct|??}} | ImageFile = Taurocholic acid structure.png | ImageSize = 200px | ImageName = Taurocholic acid | IUPACName = 2-(3α,7α,12α-Trihydroxy-5β-cholan-24-amido)ethane-1-sulfonic acid | SystematicName = 2-<nowiki/>{(4''R'')-4-[(1''R'',3a''S'',3b''R'',4''R'',5a''S'',7''R'',9a''S'',9b''S'',11''S'',11a''R'')-4,7,11-Trihydroxy-9a,11a-dimethylhexadecahydro-1''H''-cyclopenta[''a'']phenanthren-1-yl]pentanamido}ethane-1-sulfonic acid | Section1 = {{Chembox Identifiers | IUPHAR_ligand = 4547 | 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 | InChIKey = WBWWGRHZICKQGZ-HZAMXZRMBW | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = WBWWGRHZICKQGZ-HZAMXZRMSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 81-24-3 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 5E090O0G3Z | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 224867 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 6423 | PubChem = 6675 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 28865 | 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 }} | Section2 = {{Chembox Properties |C=26|H=45|N=1|O=7|S=1 | MolarMass = 515.7058 g/mol | Density = | MeltingPtC = 125.0 | BoilingPt = }} }}
'''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.<ref>{{cite journal|doi=10.1002/hep.20090|pmid=14999673|title=Cellular regulation of hepatic bile acid transport in health and cholestasis|year=2004|last1=Anwer|first1=M. Sawkat|journal=Hepatology|volume=39|issue=3|pages=581–590|s2cid=2601263 }}</ref>
Hydrolysis of taurocholic acid yields taurine.
For commercial use, taurocholic acid is manufactured from cattle bile, a byproduct of the meat-processing industry.<ref>[http://www.glycofinechem.com/content/taurocholic-acid-sodium-salt Taurocholic acid, sodium salt] {{Webarchive|url=https://web.archive.org/web/20090421063404/http://www.glycofinechem.com/content/taurocholic-acid-sodium-salt |date=2009-04-21 }} at GlycoFineChem.com</ref>
This acid is also one of the many molecules in the body that has cholesterol as its precursor.{{cn|date=March 2022}}
In a large prospective study (involving 569 incident colon cancer cases and 569 matched controls) it was found that prediagnostic concentrations of circulating taurocholic acid, as well as six other bile acids, were statistically significantly associated with increased colon cancer risk.<ref>{{cite journal |vauthors=Kühn T, Stepien M, López-Nogueroles M, Damms-Machado A, Sookthai D, Johnson T, Roca M, Hüsing A, Maldonado SG, Cross AJ, Murphy N, Freisling H, Rinaldi S, Scalbert A, Fedirko V, Severi G, Boutron-Ruault MC, Mancini FR, Sowah SA, Boeing H, Jakszyn P, Sánchez MJ, Merino S, Colorado-Yohar S, Barricarte A, Khaw KT, Schmidt JA, Perez-Cornago A, Trichopoulou A, Karakatsani A, Thriskos P, Palli D, Agnoli C, Tumino R, Sacerdote C, Panico S, Bueno-de-Mesquita B, van Gils CH, Heath AK, Gunter MJ, Riboli E, Lahoz A, Jenab M, Kaaks R |title=Prediagnostic Plasma Bile Acid Levels and Colon Cancer Risk: A Prospective Study |journal=J Natl Cancer Inst |volume=112 |issue=5 |pages=516–524 |date=May 2020 |pmid=31435679 |pmc=7225675 |doi=10.1093/jnci/djz166 |url=}}</ref>
==Toxicity== The median lethal dose of taurocholic acid in newborn rats is 380 mg/kg.{{cn|date=March 2022}}
==See also== * Deoxycholic acid
==References== {{Reflist}}
Category:Bile acids Category:Cholanes Category:Deliquescent materials