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)
Dihexyverine Dihydralazine Dihydrazine Sulfate Dihydroactinidiolide Dihydro-beta-erythroidine

Digoxigenin
Digoxigenin acsv.svg
Identifiers
CAS number 1672-46-4 YesY
PubChem 15478
ChemSpider 14728 YesY
ChEBI CHEBI:42098 YesY
ChEMBL CHEMBL1153 YesY
Jmol-3D images Image 1
Properties
Molecular formula C23H34O5
Molar mass 390.51 g/mol
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Digoxigenin (DIG) is a steroid found exclusively in the flowers and leaves of the plants Digitalis purpurea, Digitalis orientalis and Digitalis lanata (foxgloves), where it is attached to sugars, to form the glycosides (e.g. Lanatoside C).[1]