4431. Gitogenin

Nomenclature

CAS number: 511-96-6
(2α,3β,5α,25R)-Spirostan-2,3-diol; digin.
C27H44O4; mol wt 432.64.
C 74.96%, H 10.25%, O 14.79%.

Description and references

Obtained from gitonin by heating with dil HCl. Structure: Tschesche, Ber. 68, 1090 (1935); Jacobs, Simpson, J. Biol. Chem. 110, 429 (1935); Marker, Rohrmann, J. Am. Chem. Soc. 61, 2724 (1939); 62, 647 (1940); Noller, Lieberman, ibid. 63, 2131 (1941); Klass et al, ibid. 77, 3829 (1955). Pharmacological study: H. K. Iwamoto et al., J. Pharmacol. Exp. Ther. 91, 130 (1947).

Chemical structure

Properties

Leaflets from benzene, dec 271.5-275°. [α]D20 75° (c = 1.02 in CHCl3). Sol in chloroform, hot alc; sparingly sol in cold ethyl acetate, in ether; practically insol in water. Not precipitated by digitonin.

Derivative

Diacetate.
C31H48O6; mol wt 516.71.
C 72.06%, H 9.36%, O 18.58%.

Properties

Long needles from ether + methanol, mp 251-254°. [α]D20 96° (c = 1.92 in CHCl3).