2925. Desmosterol

Nomenclature

CAS number: 313-04-2
3β-Cholesta-5,24-dien-3-ol; 24-dehydrocholesterol; desmesterol.
C27H44O; mol wt 384.64.
C 84.31%, H 11.53%, O 4.16%.

Description and references

Has been isolated from chick embryos and the skin of rats: Stokes et al., J. Biol. Chem. 220, 415 (1956). From barnacles: Fagerlund, Idler, J. Am. Chem. Soc. 79, 6473 (1957); from red algae: Idler et al., Steroids 11, 465 (1968). Synthesis: Dasgupta et al., J. Org. Chem. 39, 1658 (1974); M. A. Apfel, ibid. 43, 2284 (1978). Stereospecific synthesis: M. Koreeda et al., ibid. 45, 1172 (1980); S. Takano et al., Chem. Commun. 1983, 760.

Chemical structure

Properties

Platelets from methanol, mp 121.5°, also reported as 119-119.5°. [α]D27 -41.0° (c = 1 in chloroform).