Sarsasapogenin
Title: Sarsasapogenin
CAS Registry Number: 126-19-2
CAS Name: (3b,5b,25S)-Spirostan-3-ol
Additional Names: parigenin
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, fil., Liliaceae (Sarsaparilla): Power, Salway, J. Chem. Soc. 105, 201 (1914); Jacobs, Simpson, J. Biol. Chem. 105, 501 (1934); 109, 573 (1935). Partial structure: Hirschmann et al., J. Org. Chem. 20, 572 (1955). Stereochemistry: Taylor, Chem. Ind. (London) 1954, 1066; Wall, Serota, J. Am. Chem. Soc. 76, 2850 (1954); Callow, Massey-Beresford, J. Chem. Soc. 1957, 4482; Rosen et al., J. Am. Chem. Soc. 81, 1687 (1959). Reviews: Turner, The Steroidal Sapogenins Pub. no. 361, (Univ. Microfilms, Ann Arbor, Mich., 1941) 249 pp; Shabica, Sarsasapogenin and Related Compounds, Univ. Microfilms (Ann Arbor, Mich.), Pub. no. 549, 89 pp (1943); L. F. Fieser, M. Fieser, Steroids (Reinhold, New York, 1959) p 810. See also Smilagenin.
Properties: Large prismatic needles from acetone, mp 199-199.5°. [a]D25 -75°, [a]25546 -89° (c = 0.5 in CHCl3). uv spectrum: Smith, Eddy, Anal. Chem. 31, 1539 (1959). Sol in alcohol, acetone, benzene, chloroform. Is precipitated by digitonin.
Melting point: mp 199-199.5°
Optical Rotation: [a]D25 -75°; [a]25546 -89° (c = 0.5 in CHCl3)
 
Derivative Type: Acetate
Molecular Formula: C29H46O4
Molecular Weight: 458.67
Percent Composition: C 75.94%, H 10.11%, O 13.95%
Properties: Flat needles from methanol, mp 144-145°. [a]D25 -70.2°; [a]25546 -83.1° (c = 1.18 in CHCl3).
Melting point: mp 144-145°
Optical Rotation: [a]D25 -70.2°; [a]25546 -83.1° (c = 1.18 in CHCl3)
 
Use: In the manuf of compds of the pregnane series.

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