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Taurocholic acid information


Taurocholic acid
Taurocholic acid
Names
IUPAC name
2-(3α,7α,12α-Trihydroxy-5β-cholan-24-amido)ethane-1-sulfonic acid
Systematic IUPAC name
2-{(4R)-4-[(1R,3aS,3bR,4R,5aS,7R,9aS,9bS,11S,11aR)-4,7,11-Trihydroxy-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanamido}ethane-1-sulfonic acid
Identifiers
CAS Number
  • 81-24-3 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:28865 checkY
ChEMBL
  • ChEMBL224867 checkY
ChemSpider
  • 6423 checkY
ECHA InfoCard 100.001.216 Edit this at Wikidata
IUPHAR/BPS
  • 4547
PubChem CID
  • 6675
UNII
  • 5E090O0G3Z checkY
CompTox Dashboard (EPA)
  • DTXSID00883259 Edit this at Wikidata
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 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
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.[citation needed]

  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. S2CID 2601263.
  2. ^ Taurocholic acid, sodium salt Archived 2009-04-21 at the Wayback Machine at GlycoFineChem.com

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Taurocholic acid

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Taurocholic acid, known also as cholaic acid, cholyltaurine, or acidum cholatauricum, is a deliquescent yellowish crystalline bile acid involved in the...

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Bile acid

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Primary bile acids are those synthesized by the liver. Secondary bile acids result from bacterial actions in the colon. In humans, taurocholic acid and glycocholic...

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Ox gall

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greenish-brown liquid mixture containing cholesterol, lecithin, taurocholic acid, and glycocholic acid. http://www.neogen.com/acumedia/pdf/ProdInfo/7216_PI.pdf...

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Cholic acid

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glycocholic and taurocholic acid, respectively. Cholic acid downregulates cholesterol-7-α-hydroxylase (rate-limiting step in bile acid synthesis), and...

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Glycocholic acid

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the bile of mammals. It is a conjugate of cholic acid with glycine. Its anion is called glycocholate. Taurocholic acid "Glycocholic Acid". MeSH. v t e...

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Bile

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Cholic acid Chenodeoxycholic acid Glycocholic acid Taurocholic acid Deoxycholic acid Lithocholic acid Medicine portal Animals portal Bile acid sequestrant...

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Taurine

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the anthelmintic drug netobimin (Totabin). Taurolidine Taurocholic acid and tauroselcholic acid Tauromustine 5-Taurinomethyluridine and 5-taurinomethyl-2-thiouridine...

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Aeromicrobium halocynthiae

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produces taurocholic acid. Kim, S. H.; Yang, H. O.; Sohn, Y. C.; Kwon, H. C. (15 January 2010). "Aeromicrobium halocynthiae sp. nov., a taurocholic acid-producing...

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Dietary fiber

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1016/0005-2760(68)90018-0. PMID 5645448. Gelissen IC, Eastwood MA (August 1995). "Taurocholic acid adsorption during non-starch polysaccharide fermentation: an in vitro...

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Steroid

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DHEATooltip dehydroepiandrosterone and allopregnanolone Bile acids such as taurocholic acid Aminosteroid neuromuscular blocking agents (mainly synthetic)...

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SeHCAT

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This test has replaced 14C-labeled glycocholic acid (or taurocholic acid) breath tests and fecal bile acid measurements, which now have no place in the...

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Micellar liquid chromatography

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reference, and could be used for any secondary chemical equilibria such as acid-base equilibria, and ion-pairing, Foley further refined the model for MLC...

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