Deoxycholic Acid

Title: Deoxycholic Acid
CAS Registry Number: 83-44-3
CAS Name: (3a,5b,12a)-3,12-Dihydroxy-5-cholan-24-oic acid
Additional Names: 17b-(1-methyl-3-carboxypropyl)etiocholane-3a,12a-diol; desoxycholic acid
Molecular Formula: C24H40O4
Molecular Weight: 392.57
Percent Composition: C 73.43%, H 10.27%, O 16.30%
Literature References: Lacks the C-7 hydroxy group of cholic acid. Occurs in bile of man, ox, sheep, dog, goat, and rabbit. Isoln: Wieland, Siebert, Z. Physiol. Chem. 262, 1 (1939). From cholic acid: Sifferd, US 2765316 (1956 to Armour). Structure and synthesis: L. F. Fieser, M. Fieser, Steroids (Reinhold, New York, 1959). Laboratory prepn from ox bile: Gattermann-Wieland, Praxis des Organischen Chemikers (de Gruyter, Berlin, 40th ed., 1961) p 361. Forms molecular coordination compds (so-called choleic acids) with many substances. Complexes wth fatty acids have been studies extensively: Sobotka, Goldberg, Biochem. J. 26, 555 (1932); Sobotka, Chem. Rev. 15, 362 (1934). Surface activity: idem, Chemistry of the Steroids, New York (1938).
Properties: Crystals from alc, mp 176-178°. Not precipitated by digitonin. [a]D20 +55° (alc). pK 6.58. Soly at 15° in water 0.24 g/l; in alcohol 220.7 g/l; in ether 1.16 g/l; in chloroform 2.94 g/l; in benzene 0.12 g/l; in acetone 10.46 g/l; in glacial acetic acid 9.06 g/l. Sol in solns of alkali hydroxides or carbonates.
Melting point: mp 176-178°
pKa: pK 6.58
Optical Rotation: [a]D20 +55° (alc)
Derivative Type: Sodium salt
Additional Names: Sodium deoxycholate
Molecular Formula: C24H39NaO4
Molecular Weight: 414.55
Percent Composition: C 69.53%, H 9.48%, Na 5.55%, O 15.44%
Properties: Soly in water at 15°: >333 g/l.
Therap-Cat: Choleretic.
Keywords: Choleretic.
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