3612. Epicholestanol

Nomenclature

CAS number: 516-95-0
(3α,5α)-Cholestan-3-ol; 3α-hydroxycholestane; ε-cholestanol.
C27H48O; mol wt 388.67.
C 83.44%, H 12.45%, O 4.12%.

Description and references

The 3α-hydroxy epimer of cholestanol. Prepn from cholestanone: Ruzicka, Helv. Chim. Acta 17, 1407 (1934); cf. Marker, et al., J. Am. Chem. Soc. 57, 2359 (1935); Barnett et al., J. Chem. Soc. 1940, 1390.

Chemical structure

Properties

Needles from alcohol, mp 185-186°. [α]D20 +34° (c = 1.7 in chloroform). Less sol than cholestanol. Not precipitated by digitonin.

Derivative

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

Properties

mp 95.5-96°. Crystals from methanol.

Derivative

Benzoate.
C34H52O2; mol wt 492.78.
C 82.87%, H 10.64%, O 6.49%.

Properties

mp 102-103°. [α]546 +27.2° in chloroform.