9075. Taurocholic Acid

Nomenclature

CAS number: 81-24-3
2-[[(3α,5β,7α,12α)-3,7,12-Trihydroxy-24-oxocholan-24-yl]amino]ethanesulfonic acid; N-choloyltaurine; cholaic acid; cholyltaurine.
C26H45NO7S; mol wt 515.70.
C 60.55%, H 8.80%, N 2.72%, O 21.72%, S 6.22%.

Description and 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).

Chemical structure

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°. [α]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).

Derivative

Sodium salt.

Nomenclature

Sodium taurocholate.
C26H44NNaO7S; mol wt 537.68.
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°. [α]D20 +24° (c = 3). Very freely sol in water or alcohol. Solvent action on cholesterol: Rosin, Z. Physiol. Chem. 124, 282 (1923).

Derivative

Barium salt.

Nomenclature

Barium taurocholate.
C52H88BaN2O14S2; mol wt 1166.72.
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°. [α]D20 +25.6°. Converted to taurocholic acid by treatment with sulfuric acid.

Use

Sodium salt is a lipase accelerator. See also Ox Bile Extract.

Therapeutic Category

Choleretic.

Keywords

Choleretic