Smilagenin
Title: Smilagenin
CAS Registry Number: 126-18-1
CAS Name: (25R)-Spirostan-3b-ol
Additional Names: isosarsasapogenin
Molecular Formula: C27H44O3
Molecular Weight: 416.64
Percent Composition: C 77.83%, H 10.64%, O 11.52%
Literature References: Steroid sapogenin from Smilax ornata Hooker, Liliaceae (Sarsaparilla): Ashew et al., J. Chem. Soc. 1936, 1399; from Agave lecheguilla Tou., Amaryllidaceae: Nord, US 2897192 (1959). C25 isomer of sarsasapogenin: Scheer et al., J. Am. Chem. Soc. 77, 641 (1955). Obtained by acid isomerization of sarsasapogenin: Marker, Rohrmann, ibid. 61, 846 (1939); Wall et al., ibid. 77, 3086 (1955). For structure and stereochemistry see Sarsasapogenin.
Properties: Silky needles from acetone, mp 185°. [a]D25 -69° (c = 0.5 in chloroform). Absorption spectrum: Smith, Eddy, Anal. Chem. 31, 1539 (1959).
Melting point: mp 185°
Optical Rotation: [a]D25 -69° (c = 0.5 in chloroform)
 
Derivative Type: Acetate
Molecular Formula: C29H46O4
Molecular Weight: 458.67
Percent Composition: C 75.94%, H 10.11%, O 13.95%
Properties: Needles from methanol, mp 152°.
Melting point: mp 152°
 
Use: In making compds of the pregnane series.

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