2200. Cholestanol

Nomenclature

CAS number: 80-97-7
(3β,5α)-Cholestan-3-ol; Dihydrocholesterol; 3β-hydroxycholestane; β-cholestanol.
C27H48O; mol wt 388.67.
C 83.44%, H 12.45%, O 4.12%.

Description and references

Occurs in human feces, in gallstones, in eggs. Prepn by reduction of cholesterol: Willst"atter, Mayer, Ber. 41, 2199 (1908); Ellis, Gardner, Biochem. J. 12, 72 (1918). From coprostenone: Diels, Abderhalden, Ber. 39, 884 (1906). See also Bruce, Ralls, Org. Synth. coll. vol. II, 191 (1943).

Chemical structure

Properties

Monohydrate, scales from alc, mp 141.5-142°. [α]D22 +24.2° (c = 1.3 in chloroform). One gram dissolves in about 100 ml alcohol, in 200 ml dry methanol. Freely sol in hot alc, ether, chloroform. Pptd by digitonin.

Derivative

Methyl ether.
C28H50O; mol wt 402.70.
C 83.51%, H 12.51%, O 3.97%.

Properties

Needles from acetone, mp 82.5-83°. [α]D20 +20.0°.

Derivative

Acetate.
C29H50O2; mol wt 430.71.
C 80.87%, H 11.70%, O 7.43%.

Properties

Prisms from ethyl acetate + methanol, mp 111°. [α]D20 +13.3° (c = 2 in chloroform).