Cholanic Acid

Title: Cholanic Acid
CAS Registry Number: 25312-65-6
CAS Name: Cholan-24-oic acid
Additional Names: ursocholanic acid; 17b-(1-methyl-3-carboxypropyl)etiocholane
Molecular Formula: C24H40O2
Molecular Weight: 360.57
Percent Composition: C 79.94%, H 11.18%, O 8.87%
Literature References: Steroidal acid probably formed by the dehydration and hydrogenation of certain bile acids commonly found in animals. Considered to be a chemical trademark certifying the prehistoric presence of some type of animal, see Seifert, Pure Appl. Chem. 34, 633 (1973). This status as a natural product of exclusive animal origins now questioned by its isolation from the embryo of the jequirity bean, Abrus precatorius, Leguminosae: Mandava et al., Steroids 23, 357 (1974). Prepn from coprostane, cholic acid, lithocholic acid, desoxy- and chenodesoxycholic acid: Wieland, Weil, Z. Physiol. Chem. 80, 287 (1912); Wieland, Boersch, ibid. 106, 193 (1919); Windaus, Neukirchen, Ber. 52, 1915 (1919); Wieland, Vocke, Z. Physiol. Chem. 191, 69 (1930). From 3-ketocholanic acid diethyl thioacetal by hydrogenolysis: Bernstein, Dorfman, US 2440660 (1948 to Am. Cyanamid). 5b-Cholanic acid differs from the thermodynamically more stable 5a-isomer, by being cis at the A/B steroid ring function rather than trans.
Properties: Needles from alc, mp 163-164°. [a]D20 +21.7° (chloroform). Sol in chloroform, alcohol, acetic acid. Forms a molecular compd with allocholanic acid, mp 163.5°.
Melting point: mp 163-164°; mp 163.5°
Optical Rotation: [a]D20 +21.7° (chloroform)
Derivative Type: Methyl ester
Molecular Formula: C25H42O2
Molecular Weight: 374.60
Percent Composition: C 80.16%, H 11.30%, O 8.54%
Properties: mp 86-87°.
Melting point: mp 86-87°
Derivative Type: Ethyl ester
Molecular Formula: C26H44O2
Molecular Weight: 388.63
Percent Composition: C 80.35%, H 11.41%, O 8.23%
Properties: Needles from 80% alc, mp 93-94°; bp12 273°. [a]D19 +21° (chloroform).
Melting point: mp 93-94°
Boiling point: bp12 273°
Optical Rotation: [a]D19 +21° (chloroform)
NOTE: The name cholanic acid was formerly applied to desoxybilianic acid, C24H36O7.
Use: In chemotaxonomical classification.
Cholanthrene Cholecystokinin Cholestanol Cholesterol Cholestyramine Resin