Stigmasterol
Title: Stigmasterol
CAS Registry Number: 83-48-7
CAS Name: (3b,22E)-Stigmasta-5,22-dien-3-ol
Additional Names: 3b-hydroxy-24-ethyl-D5,22-cholestadiene
Molecular Formula: C29H48O
Molecular Weight: 412.69
Percent Composition: C 84.40%, H 11.72%, O 3.88%
Literature 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 Type: Monohydrate
Properties: Crystals from alcohol. When dry, mp 170°. [a]D22 -51° (c = 2 in chloroform). Insol in water. Sol in the usual organic solvents.
Melting point: mp 170°
Optical Rotation: [a]D22 -51° (c = 2 in chloroform)
 
Derivative Type: Acetate
Molecular Formula: C31H50O2
Molecular Weight: 454.73
Percent Composition: C 81.88%, H 11.08%, O 7.04%
Properties: mp 144°. [a]D20 -55.6° (c = 2 in chloroform).
Melting point: mp 144°
Optical Rotation: [a]D20 -55.6° (c = 2 in chloroform)
 
Derivative Type: p-Nitrobenzoate
Molecular Formula: C36H51NO4
Molecular Weight: 561.79
Percent Composition: C 76.97%, H 9.15%, N 2.49%, O 11.39%
Properties: mp 203°. [a]D17 -13° (c = 2 in alcohol).
Melting point: mp 203°
Optical Rotation: [a]D17 -13° (c = 2 in alcohol)

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