4433. Gitoxigenin

Nomenclature

CAS number: 545-26-6
(3β,5β,16β)-3,14,16-Trihydroxycard-20(22)-enolide; Δ20,22-3,14,16,21-tetrahydroxynorcholenic acid lactone.
C23H34O5; mol wt 390.51.
C 70.74%, H 8.78%, O 20.49%.

Description and references

The aglycon of gitoxin. By refluxing gitoxin in a mixture of water + alcohol + HCl: Smith, J. Chem. Soc. 1931, 23. Structure: Jacobs, Elderfield, J. Biol. Chem. 100, 671 (1933); Elderfield, Chem. Rev. 17, 217 (1935); Henderson, Chen, J. Med. Pharm. Chem. 5, 988 (1962). Configuration: Moore, Helv. Chim. Acta 37, 659 (1954); Repke, Klesczewski, Arch. Exp. Pathol. Pharmakol. 239, 131 (1960). Cf. ref under Digoxigenin.

Chemical structure

Derivative

Sesquihydrate.

Properties

Plates from dil alc. After drying at 100° in vacuo mp 234°. [α]54520 +38.5° (c = 0.68 in methanol). Absorption max (96% H2SO4): 310, 485, 520 nm. Slightly sol in alcohol, acetone, ethyl acetate. Treatment with alcoholic HCl yields digitaligenin with loss of 2H2O.

Derivative

3,16-Diacetylgitoxigenin.

Properties

mp 249-250°.

Derivative

3,16-Dibenzoylgitoxigenin.

Properties

mp 262°.