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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • 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 checkY
    Key: BHTRKEVKTKCXOH-BJLOMENOSA-N checkY
  • 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
  • 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
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).
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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

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.
  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. PMID 4562149.


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