8555. α1-Sitosterol

Nomenclature

CAS number: 474-40-8
(3β,4α,5α,24Z)-4-Methylstigmasta-7,24(28)-dien-3-ol; citrostadienol.
C30H50O; mol wt 426.72.
C 84.44%, H 11.81%, O 3.75%.

Description and references

Occurs in plants. Isoln from wheat germ oil: Anderson et al., J. Am. Chem. Soc. 48, 2987 (1926); Wallis, Fernholz, ibid. 58, 2446 (1936). Structure: Bernstein, Wallis, ibid. 61, 2308 (1939); Mazur, Sondheimer, ibid. 80, 6293, 6296 (1958). Identity with citrostadienol: Schreiber, Osske, Experientia 19, 69 (1963); eidem, Tetrahedron 20, 2575 (1964). Stereochemistry: C. Brooks et al., Steroids 20, 487 (1972).

Chemical structure

Properties

Needles from alcohol, mp 164-166°. [α]D28 -1.7° (c = 2 in chloroform). Is pptd by digitonin.