8815. Stigmasterol
Nomenclature
CAS number: 83-48-7
(3β,22E)-Stigmasta-5,22-dien-3-ol; 3β-hydroxy-24-ethyl-Δ5,22-cholestadiene. C29H48O; mol wt 412.69.
C 84.40%, H 11.72%, O 3.88%.
Description and references
Usually isolated from the phytosterol mixture from soy or calabar beans, cf. Thornton et al., J. Am. Chem. Soc. 62, 2006 (1940); Byerrum, Ball, Biochem. Prep. 7, 86 (1959). Structure: Fernholz, Ann. 507, 128 (1933); 508, 215 (1933); Fernholz, Chakravorty, Ber. 67, 2021 (1934). Identity with guinea-pig-anti-stiffness factor: H. Rosenkrantz et al., Proc. Soc. Exp. Biol. Med. 76, 408 (1951). Synthesis: W. Sucrow, M. Slopianka, Ber. 108, 3721 (1975). HPLC separation from plant oils: H. Colin et al., Anal. Chem. 51, 1661 (1979).
Derivative
Monohydrate.Properties
Crystals from alcohol. When dry, mp 170°. [α]D22 51° (c = 2 in chloroform). Insol in water. Sol in the usual organic solvents.Derivative
Acetate.C31H50O2; mol wt 454.73.
C 81.88%, H 11.08%, O 7.04%.
Properties
mp 144°. [α]D20 55.6° (c = 2 in chloroform).Derivative
p-Nitrobenzoate.C36H51NO4; mol wt 561.79.
C 76.97%, H 9.15%, N 2.49%, O 11.39%.