3166. Digoxigenin

Nomenclature

CAS number: 1672-46-4
(3β,5β,12β)-3,12,14-Trihydroxycard-20(22)-enolide; Δ20:22-3β,12β,14,21-tetrahydroxynorcholenic acid lactone; lanadigenin.
C23H34O5; 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).

Chemical structure

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).

Derivative

3,12-Diacetyldigoxigenin.

Properties

Prisms from dil methanol, mp 222-223°. [α]20546 +61.3° (c = 2 in methanol).