Nomenclature
CAS number: 1672-46-4
(3β,5β,12β)-3,12,14-Trihydroxycard-20(22)-enolide; Δ
20:22-3β,12β,14,21-tetrahydroxynorcholenic acid
lactone; lanadigenin.
C
23H
34O
5; mol wt 390.51.
C 70.74%, H 8.78%, O 20.49%.
Description and references
The aglycone of digoxin. By hydrolysis of
digoxin: Smith, J. Chem. Soc. 1930, 508. From Digitalis orientalis L. and D. lanata Ehrh., Scrophulariaceae: Mannick, Schneider, Arch. Pharm. 279, 223 (1941);
Pataki et al., Helv. Chim. Acta 36, 1295 (1953). Structure: Meyer, Reichstein, Experientia 9, 253 (1953); Cardwell,
Smith, ibid. 367; eidem, J. Chem. Soc. 1954, 2012. Synthesis: P.
Welzel, H. Stein, Tetrahedron Lett. 22, 3385 (1981).
Derivative
Dihydrate.
Properties
Prismatic rods from dil alc. Anhydr as stout
prisms from ethyl acetate, mp 222°. [α]20546 +27.0° (c = 1.77 in methanol). Although it is a 3β-alcohol, it is not precipitated by digitonin
(Pataki).