BETA-ACETYLDIGOXIN Property

Melting point:

271-273°C

alpha 

D20 +30.4° (c = 1.2 in alc)

Boiling point:

681.03°C (rough estimate)

Density 

1.1139 (rough estimate)

refractive index 

1.5940 (estimate)

storage temp. 

-20°C Freezer

solubility 

Practically insoluble in water, sparingly soluble in methylene chloride, slightly soluble in ethanol (96 per cent).

pka

13.41±0.70(Predicted)

Safety

RIDADR 

3249

HazardClass 

6.1(a)

PackingGroup 

II

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

BETA-ACETYLDIGOXIN Chemical Properties,Usage,Production

Chemical Properties

White Solid

Originator

Novodigal ,Asta Medica Arzneimittel

Uses

Digoxin derivative, a cardiotonic glycosides

Definition

ChEBI: Acetyldigoxin is a cardenolide glycoside.

Manufacturing Process

Dried crude product of the partial acetylation of digoxin (42 g) prepared from digitalis - is dissolved under reflux in acetone (480 ml) and n-hexane (2400 ml) is added to the solution with stirring. Fine crystals, which begin to separate immediately, are left at room temperature for 5 hours, then they are filtered with suction, washed with n-hexane and dried in vacuum at 40°C, yielding 32 g of crude β-acetyldigoxin (product 1). Product 1 (31 g) is dissolved under reflux in chloroform (500 ml) and toluene (2500 ml) is added thereto with stirring. The crystals, which separate after standing for 6 hours at room temperature, are filtered, washed with toluene and ether and dried in vacuum yielding 29 g of β-acetyldigoxin (product 2). MP: 249°-251°C.
The filtrate, which results from the separation of product 1, is evaparated to dryness in vacuum. The residue, which mainly contains unreacted digoxin, is purified by recrystallization from pyridine/ether/water (3.5:5:40) and repeatedly acetylated. It can then be recycled to produce more β- acetyldigoxin. The filtrate resulting from the separation of product 2 is evaporated to dryness. The resulting residue contains the di- and polyacetyl derivatives of digoxin, which are deacetylated to digoxin in a known manner and later is returned to a further acetylation process and can then be recycled to produce more β-acetyldigoxin. Beta-Acetyldigoxin may be prepared from digoxin, acetic acid and dicyclohexylcarbodiimide using the last one as a condensing agent.

Therapeutic Function

Cardiotonic