Gentrogenin

Title: Gentrogenin
CAS Registry Number: 427-28-1
CAS Name: (3b,25R)-3-Hydroxyspirost-5-en-12-one
Additional Names: 20a,22a,25D-spirost-5-en-3b-ol-12-one; botogenin
Molecular Formula: C27H40O4
Molecular Weight: 428.60
Percent Composition: C 75.66%, H 9.41%, O 14.93%
Literature 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).
Properties: Rectangular plates from methanol, mp 215-216°. [a]D28 -56° (c = 1.02 in CHCl3).
Melting point: mp 215-216°
Optical Rotation: [a]D28 -56° (c = 1.02 in CHCl3)
Derivative Type: Acetate
Molecular Formula: C29H42O5
Molecular Weight: 470.64
Percent Composition: C 74.01%, H 8.99%, O 17.00%
Properties: Crystals from ethyl acetate, mp 227°. [a]D25 -58.1° (c = 1.02 in CHCl3).
Melting point: mp 227°
Optical Rotation: [a]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.
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