3160. Digitogenin

Nomenclature

CAS number: 511-34-2
(2α,3β,5α,15β,25R)-Spirostan-2,3,15-triol.
C27H44O5; mol wt 448.64.
C 72.28%, H 9.89%, O 17.83%.

Description and references

The aglycon of digitonin: Tschesche, Ber. 68, 1090 (1935); Tschesche, Hagedorn, Ber. 69, 797 (1936). Structure and stereochemistry: Marker et al., J. Am. Chem. Soc. 64, 1843 (1942); Meystre et al., Helv. Chim. Acta 38, 381 (1955). Klass et al., J. Am. Chem. Soc. 77, 3829 (1955); and IR spectra: Djerassi et al., ibid. 78, 3166 (1956).

Chemical structure

Properties

Needles from alc, dec 296°. [α]D19 -81° (c = 1.4 in chloroform). Practically insol in water. Sol in 30 parts chloroform, 35 parts boiling alc, 100 parts alc at 20°.

Derivative

2,3-Diacetate.

Properties

Crystals from methanol-chloroform, mp 241.5-242°. [α]D -104°.

Derivative

Triacetate.

Properties

Minute needles from ether, mp 190°.