Title: Glycocholic Acid
CAS Registry Number: 475-31-0
CAS Name: N-[(3a,5b,7a,12a)-3,7,12-trihydroxy-24-oxocholan-24-yl]glycine
Additional Names: N-cholylglycine
Molecular Formula: C26H43NO6
Molecular Weight: 465.62
Percent Composition: C 67.07%, H 9.31%, N 3.01%, O 20.62%
Literature References: The product of conjugation of cholic acid with glycine; chief ingredient of the bile of herbivorous animals. In the weakly alkaline bile fluid glycocholic acid exists as the sodium salt. Prepn from bile: Hammarsten in Abderhalden's Handbuch der Biol. Arbeitsmethoden, Abt. I, Teil 6, p 211 (1925). Prepn from cholic acid: Cortese, J. Am. Chem. Soc. 59, 2532 (1937). Synthesis: Cortese, Bauman, ibid. 57, 1393 (1935); Bergstrom, Norman, Acta Chem. Scand. 7, 1126 (1953). Separation: Antonides, GB 928635 (1963 to Armour). Metabolism: Norman, Scand. J. Gastroenterol. 5, 231 (1970).
Derivative Type: Sesquihydrate
Properties: Crystals from 5% alc, mp about 130°. [a]D23 +30.8° (c = 7.5 in 95% ethanol). Anhydr form, mp 165-168°. pK 4.4. Soly in water at 15°: 0.33 g/l; in boiling water: 8.3 g/l. Is hydrolyzed to cholic acid and glycine by acids and alkalies. Forms addition compds with nitrobenzene, aniline, benzyl alcohol, benzaldehyde, triolein.
Melting point: mp about 130°; mp 165-168°
pKa: pK 4.4
Optical Rotation: [a]D23 +30.8° (c = 7.5 in 95% ethanol)
Derivative Type: Sodium salt
Molecular Formula: C26H42NNaO6
Molecular Weight: 487.60
Percent Composition: C 64.04%, H 8.68%, N 2.87%, Na 4.71%, O 19.69%
Properties: Crystals from 95% alcohol + ether, mp 230-240°. [a]D24 +32° (water). Soly at 15° in water >274 g/l; in alcohol >340 g/l.
Melting point: mp 230-240°
Optical Rotation: [a]D24 +32° (water)
|