3288. Dinosterol

Nomenclature

CAS number: 58670-63-6
(3β,4α,5α,22E)-4,23-Dimethylergost-22-en-3-ol; 4α-methyl-5α(H)-Δ22-23,24-dimethylcholesten-3β-ol; Black Sea sterol.
C30H52O; mol wt 428.73.
C 84.04%, H 12.23%, O 3.73%.

Description and references

Biogenetically important marine sterol isolated from the toxic dinoflagellate, Gonyaulax tamarensis. Isoln and structure determn: Y. Shimizu et al., J. Am. Chem. Soc. 98, 1059 (1976). Stereochemistry: J. Finer et al., J. Org. Chem. 43, 1990 (1978). Identity with the Black Sea sterol: J. J. Boon et al., Nature 277, 125 (1979). Stereospecific synthesis: A. Y. L. Shu, C. Djerassi, Tetrahedron Lett. 22, 4627 (1981).

Chemical structure

Properties

Needles from methanol-chloroform, mp 220-222° (Shimizu). Also reported as mp 211-214° (Shu, Djerassi). [α]20D -2.2° (in CHCl3).