12-04407. Gentrogenin [Archived]

Nomenclature

CAS number: 427-28-1
(3β,25R)-3-Hydroxyspirost-5-en-12-one; 20α,22a,25d-spirost-5-en-3β-ol-12-one; botogenin.
C27H40O4; mol wt 428.60.
C 75.66%, H 9.41%, O 14.93%.

Description and references

Isoln from acid hydrolysis mixture of sapogenins of Dioscorea mexicana: Marker, Lopez, J. Am. Chem. Soc. 69, 2397 (1947); from crude sapogenin mixture extracted from tubers of D. spiculiflora, Dioscoreaceae: Walens et al., J. Org. Chem. 22, 182 (1957); Townley, US 2954374 (1960 to Schering); from Heloniopsis orientalis (Thunb.) C. Tanaka, Liliaceae: Okanishi et al., Chem. Pharm. Bull. 10, 1195 (1962). Structure: Walens et al., US 2830986 (1958 to USDA).

Chemical structure

Properties

Rectangular plates from methanol, mp 215-216°. [α]D28 56° (c = 1.02 in CHCl3).

Derivative

Acetate.
C29H42O5; mol wt 470.64.
C 74.01%, H 8.99%, O 17.00%.

Properties

Crystals from ethyl acetate, mp 227°. [α]D25 58.1° (c = 1.02 in CHCl3).

Use

Precursor for synthesis of pharmacologically active steroids.

Status

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