89. Acetyldigitoxins

C43H66O14; mol wt 806.98.
C 64.00%, H 8.24%, O 27.76%.

Description and references

Obtained by enzymatic hydrolysis of lanatoside A, q.v. Composed of the aglycone digitoxigenin and 3 mols digitoxose, to one of which an acetyl group is attached. Acetyldigitoxin-α differs from acetyldigitoxin-β in the position of the acetyl group. The β-form is obtained either by splitting off the glucose residue from lanatoside A by means of enzymes, or by extraction from the leaves of Digitalis ferruginea L., Scrophulariaceae. The α-form can be obtained from acetyldigitoxin-β by heating in an anhydrous or aq organic solvent at pH 3.5 to 8: Stoll, Kreis, US 2776963 (1957 to Sandoz).

Derivative

α-Form.

Nomenclature

CAS number: 1111-39-3
Acylanid (Sandoz).

Properties

Platelets from methanol, mp 217-221°. [α]D20 +5.0° (c = 0.7 in pyridine). Slightly sol in chloroform.

Derivative

β-Form.

Properties

Stout, solvated prisms from methanol losing their solvent of crystn in desiccator. When dry, dec 225°. [α]D20 +16.7° (pyridine). One gram dissolves in 7 to 9 ml chloroform, in 150 ml methanol, in 220 ml amyl alc. Almost insol in ether, water (one gram dissolves in 200 liters H2O at 20°).

Therapeutic Category

Cardiotonic.

Keywords

Cardiotonic