Digoxigenin
Title: Digoxigenin
CAS Registry Number: 1672-46-4
CAS Name: (3b,5b,12b)-3,12,14-Trihydroxycard-20(22)-enolide
Additional Names: D20:22-3b,12b,14,21-tetrahydroxynorcholenic acid lactone; lanadigenin
Molecular Formula: C23H34O5
Molecular Weight: 390.51
Percent Composition: C 70.74%, H 8.78%, O 20.49%
Literature 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 Type: Dihydrate
Properties: Prismatic rods from dil alc. Anhydr as stout prisms from ethyl acetate, mp 222°. [a]20546 +27.0° (c = 1.77 in methanol). Although it is a 3b-alcohol, it is not precipitated by digitonin (Pataki).
Melting point: mp 222°
Optical Rotation: [a]20546 +27.0° (c = 1.77 in methanol)
 
Derivative Type: 3,12-Diacetyldigoxigenin
Properties: Prisms from dil methanol, mp 222-223°. [a]20546 +61.3° (c = 2 in methanol).
Melting point: mp 222-223°
Optical Rotation: [a]20546 +61.3° (c = 2 in methanol)

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