12-02834. Cynanchogenin [Archived]

Nomenclature

CAS number: 6870-10-6
(3β,12β,14β,17α)-12-[(3,4-Dimethyl-1-oxo-2-pentenyl)oxy]-3,8,14-trihydroxypregn-5-en-20-one.
C28H42O6; mol wt 474.63.
C 70.86%, H 8.92%, O 20.23%.

Description and references

From root of Cynanchum caudatum Max., Asclepiadaceae: Mitsuhashi, Shimizu, Chem. Pharm. Bull. 8, 313, 318 (1960). Proposed structure: eidem, Steroids 2, 373 (1963). Revised structure: eidem, Tetrahedron 24, 4143 (1968). 13C-NMR studies: T. Yamagishi et al., Tetrahedron Lett. 1973, 3527, 3531.

Chemical structure

Properties

Fine needles from ether + petr ether, mp 165-167°. [α]D22 39.5° (c = 1.24 in 90% ethanol). uv max (ethanol): 218 nm (log ε 4).

Derivative

Monoacetate.
C30H44O7; mol wt 516.67.
C 69.74%, H 8.58%, O 21.68%.

Properties

Crystals from petr ether + benzene, mp 150°.

Status

This monograph has been retired and is no longer subject to revision or update.