4280. Fucosterol

Nomenclature

CAS number: 17605-67-3
(3β,24E)-Stigmasta-5,24(28)-dien-3-ol; 24-ethylidenecholest-5-en-3β-ol.
C29H48O; mol wt 412.69.
C 84.40%, H 11.72%, O 3.88%.

Description and references

Isoln from Fucus vesiculosus L., Fucaceae: Heilbron et al., J. Chem. Soc. 1934, 1572; from marine brown algae (Phaeophyceae): Tsuda, Chem. Pharm. Bull. 6, 724 (1958). Structure: MacPhillamy, J. Am. Chem. Soc. 64, 1732 (1942). Stereochemistry: C. Brooks et al., Steroids 20, 487 (1972). Synthesis: Hayazu, Pharm. Bull. 5, 452 (1957).

Chemical structure

Properties

Crystals from methanol, mp 124°. [α]D20 38.4° (chloroform). Soluble in most organic solvents.

Derivative

Acetate.
C31H50O2; mol wt 454.73.
C 81.88%, H 11.08%, O 7.04%.

Properties

Crystals, mp 120-121°. [α]D20 45° (chloroform).