Dioscorine

Title: Dioscorine
CAS Registry Number: 3329-91-7
CAS Name: [1R-(1a,4a,5a)]-2,4¢-Dimethylspiro[2-azabicyclo[2.2.2]octane-5,2¢-[2H]pyran]-6¢(3¢H)-one
Molecular Formula: C13H19NO2
Molecular Weight: 221.30
Percent Composition: C 70.56%, H 8.65%, N 6.33%, O 14.46%
Literature References: Found in the tubers of Dioscorea hirsuta Blume and D. hispida Dennst., Dioscoreaceae: H. W. Schutte, Chem. Zentralbl. 68, II, 130 (1897); M. K. Gorter, Rec. Trav. Chim. 30, 161 (1911); A. R. Pinder, Nature 168, 1090 (1951); idem, J. Chem. Soc. 1952, 2236. Structure: W. A. M. Davies et al., Chem. Ind. (London) 1961, 1410; eidem, Tetrahedron 18, 405 (1962); Morris, A. R. Pinder, J. Chem. Soc. 1963, 1841. Synthesis: Page, A. R. Pinder, ibid. 1964, 4811. Absolute configuration: A. F. Beecham et al., Tetrahedron Lett. 1969, 3745. Biosynthetic studies: E. Leete, A. R. Pinder, Chem. Commun. 1971, 1499; E. Leete, J. Am. Chem. Soc. 99, 648 (1977). Pharmacology: A. R. Pinder, J. Chem. Soc. 1953, 1826. Evaluation of toxic components: J. Webster et al., J. Agric. Food Chem. 32, 1087 (1984).
Properties: Greenish-yellow prisms from ether, mp 54-55°. [a]D18 -35.0° (c = 3.4 in chloroform). uv max (methanol): 215 nm (e 10160). Distills unchanged in vacuo. Sol in water, alcohol, acetone, chloroform; slightly sol in ether, benzene, petr ether.
Melting point: mp 54-55°
Optical Rotation: [a]D18 -35.0° (c = 3.4 in chloroform)
Absorption maximum: uv max (methanol): 215 nm (e 10160)
Derivative Type: Hydrochloride
Molecular Formula: C13H19NO2.HCl
Molecular Weight: 257.76
Percent Composition: C 60.58%, H 7.82%, N 5.43%, O 12.41%, Cl 13.75%
Properties: Needles from alcohol + ether, dec 210-211°.
Diosgenin Diosmin Diosphenol Dioxadrol Dioxane