Taurocholic Acid
Title: Taurocholic Acid
CAS Registry Number: 81-24-3
CAS Name: 2-[[(3a,5b,7a,12a)-3,7,12-Trihydroxy-24-oxocholan-24-yl]amino]ethanesulfonic acid
Additional Names: N-choloyltaurine; cholaic acid; cholyltaurine
Molecular Formula: C26H45NO7S
Molecular Weight: 515.70
Percent Composition: C 60.55%, H 8.80%, N 2.72%, O 21.72%, S 6.22%
Literature References: The product of conjugation of cholic acid with taurine. Its sodium salt is the chief ingredient of the bile of carnivorous animals. Prepn from dog bile: Hammarsten in Abderhalden, Handbuch der Biol. Arbeitsmethoden, Abt. I, Teil 6, p 219 (1925). Separation from bile acids: Ahrens, Craig, J. Biol. Chem. 195, 763 (1952). Enzymic synthesis: Siperstein, Murray, Science 123, 377 (1956). Prepn of the sodium salt: Cortese, J. Am. Chem. Soc. 59, 2532 (1937); Norman, Ark. Kemi 8, 331 (1955); of the barium salt: Kazuno, Yanazaki, Z. Physiol. Chem. 224 160 (1934). Binding of taurocholic acid to serum proteins: Burke et al., Clin. Chim. Acta 32, 207 (1971). Toxicity data: Klaassen, Toxicol. Appl. Pharmacol. 24, 37 (1973).
Properties: Clusters of slender, four-sided prisms from alcohol + ether, stable to air. (Commercial prepns are usually amorphous, very hygroscopic, and of yellow color.) Dec about 125°. [a]D18 +38.8° (c = 2 in alcohol). pK 1.4. Freely sol in water, sol in alcohol. Almost insol in ether, ethyl acetate. Is hydrolyzed to cholic acid and taurine by acids and alkalies. LD50 in newborn rats: 380 mg/kg (Klaassen).
pKa: pK 1.4
Optical Rotation: [a]D18 +38.8° (c = 2 in alcohol)
Toxicity data: LD50 in newborn rats: 380 mg/kg (Klaassen)
Derivative Type: Sodium salt
Additional Names: Sodium taurocholate
Molecular Formula: C26H44NNaO7S
Molecular Weight: 537.68
Percent Composition: C 58.08%, H 8.25%, N 2.61%, Na 4.28%, O 20.83%, S 5.96%
Properties: Crystals with 1.5 and 2 mols H2O. Sweet taste with bitter aftertaste. Dec about 230°. [a]D20 +24° (c = 3). Very freely sol in water or alcohol. Solvent action on cholesterol: Rosin, Z. Physiol. Chem. 124, 282 (1923).
Optical Rotation: [a]D20 +24° (c = 3)
Derivative Type: Barium salt
Additional Names: Barium taurocholate
Molecular Formula: C52H88BaN2O14S2
Molecular Weight: 1166.72
Percent Composition: C 53.53%, H 7.60%, Ba 11.77%, N 2.40%, O 19.20%, S 5.50%
Properties: Crystals with 5 mols H2O, dec 225-227°. [a]D20 +25.6°. Converted to taurocholic acid by treatment with sulfuric acid.
Optical Rotation: [a]D20 +25.6°
Use: Sodium salt is a lipase accelerator. See also Ox Bile Extract.
Therap-Cat: Choleretic.
Keywords: Choleretic.

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