gamma-Sitosterol

Title: g-Sitosterol
CAS Registry Number: 83-47-6
CAS Name: (3b,24S)-Stigmast-5-en-3-ol
Additional Names: clionasterol
Molecular Formula: C29H50O
Molecular Weight: 414.71
Percent Composition: C 83.99%, H 12.15%, O 3.86%
Literature 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 b-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).
Derivative Type: Monohydrate
Properties: Plates from alcohol. When dry, mp 147-148°. [a]D20 -43° (c = 1.9 in chloroform). Table of mp's and [a]D's: Dirscherl, Z. Physiol. Chem. 257, 242 (1939).
Melting point: mp 147-148°
Optical Rotation: [a]D20 -43° (c = 1.9 in chloroform)
Derivative Type: Acetate
Molecular Formula: C31H52O2
Molecular Weight: 456.74
Percent Composition: C 81.52%, H 11.48%, O 7.01%
Properties: mp 143-144°. [a]D20 -45.3° (c = 1.9 in chloroform).
Melting point: mp 143-144°
Optical Rotation: [a]D20 -45.3° (c = 1.9 in chloroform)
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