8557. γ-Sitosterol

Nomenclature

CAS number: 83-47-6
(3β,24S)-Stigmast-5-en-3-ol; clionasterol.
C29H50O; mol wt 414.71.
C 83.99%, H 12.15%, O 3.86%.

Description and references

Principal sterol of soybean oil: Bonstedt, Z. Physiol. Chem. 176, 269 (1928). Isoln from corn oil: Anderson, Shriner, J. Am. Chem. Soc. 48, 2976 (1926); from venom of Chinese toad, Bufo gargarizans: Rukstuhl, Meyer, Helv. Chim. Acta 40, 1270 (1957). Differs from β-sitosterol in spatial configuration at C-24: Bergmann, Low, J. Org. Chem. 12, 67 (1947). Structure: Pavanaram, Helv. Chim. Acta 46, 1377 (1963). Stereospecific synthesis: W. Sucrow, M. Slopianka, Ber. 108, 3721 (1975).

Chemical structure

Derivative

Monohydrate.

Properties

Plates from alcohol. When dry, mp 147-148°. [α]D20 -43° (c = 1.9 in chloroform). Table of mp's and [α]D's: Dirscherl, Z. Physiol. Chem. 257, 242 (1939).

Derivative

Acetate.
C31H52O2; mol wt 456.74.
C 81.52%, H 11.48%, O 7.01%.

Properties

mp 143-144°. [α]D20 -45.3° (c = 1.9 in chloroform).