Taurochenodeoxycholic acid

Taurochenodeoxycholic acid is a bile acid formed in the liver of most species, including humans, by conjugation of chenodeoxycholic acid with taurine.^[1] It is secreted into bile and then into the intestine.^[2] It is usually ionized at physiologic pH. However, although it can be crystallized as the sodium salt.

Taurochenodeoxycholic acid

Names
IUPAC name 2-(3α,7α-Dihydroxy-5β-cholan-24-amido)ethane-1-sulfonic acid
Systematic IUPAC name 2-{(4R)-4-[(1R,3aS,3bR,4R,5aS,7R,9aS,9bS,11aR)-4,7-Dihydroxy-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanamido}ethane-1-sulfonic acid
Other names 12-Deoxycholyltaurine; 12-Desoxycholyltaurine; Chenodeoxycholyltaurine; Chenyltaurine
Identifiers
CAS Number	516-35-8 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16525 Y
ChEMBL	ChEMBL185878 Y
ChemSpider	343282 Y
IUPHAR/BPS	4747
PubChem CID	387316
UNII	651KU15938 Y
CompTox Dashboard (EPA)	DTXSID101020121
InChI InChI=1S/C26H45NO6S/c1-16(4-7-23(30)27-12-13-34(31,32)33)19-5-6-20-24-21(9-11-26(19,20)3)25(2)10-8-18(28)14-17(25)15-22(24)29/h16-22,24,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33)/t16-,17+,18-,19-,20+,21+,22-,24+,25+,26-/m1/s1 Y Key: BHTRKEVKTKCXOH-BJLOMENOSA-N Y InChI=1/C26H45NO6S/c1-16(4-7-23(30)27-12-13-34(31,32)33)19-5-6-20-24-21(9-11-26(19,20)3)25(2)10-8-18(28)14-17(25)15-22(24)29/h16-22,24,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33)/t16-,17+,18-,19-,20+,21+,22-,24+,25+,26-/m1/s1 Key: BHTRKEVKTKCXOH-BJLOMENOBE
SMILES O=S(=O)(O)CCNC(=O)CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]4[C@H]2[C@H](O)C[C@@H]3C[C@H](O)CC[C@@]34C)C
Properties
Chemical formula	C26H45NO6S
Molar mass	499.71 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

It acts as a detergent to solubilize fats in the small intestine and is itself absorbed by active transport in the terminal ileum.^[3]

It is used as a cholagogue and choleretic.

See also

• Tauroursodeoxycholic acid, an epimer
• See article about Taurodeoxycholic acid as an interferent in Perfluorooctanesulfonic acid (PFOS) mass spectrometry analysis.

References

1. Hofmann AF (1999). "The continuing importance of bile acids in liver and intestinal disease". Arch. Intern. Med. 159 (22): 2647–58. doi:10.1001/archinte.159.22.2647. PMID 10597755. S2CID 21211064.
2. Perez de la Cruz Moreno M, Oth M, Deferme S, Lammert F, Tack J, Dressman J, Augustijns P (August 2006). "Characterization of fasted-state human intestinal fluids collected from duodenum and jejunum". The Journal of Pharmacy and Pharmacology. 58 (8): 1079–89. doi:10.1211/jpp.58.8.0009. PMID 16872555.
3. Carey MC, Small DM (October 1972). "Micelle formation by bile salts. Physical-chemical and thermodynamic considerations". Archives of Internal Medicine. 130 (4): 506–27. doi:10.1001/archinte.1972.03650040040005. PMID 4562149.