2565. Coumingine

Nomenclature

CAS number: 26241-81-6
[2S-(2α,4aα,4bβ,7E,8β,8aα,10aβ)]-3-Hydroxy-3-methylbutanoic acid 7-[2-[2-(dimethylamino)ethoxy]-2-oxoethylidene]tetradecahydro-1,1,4a,8-tetramethyl-9-oxo-2-phenanthrenyl ester.
C29H47NO6; mol wt 505.69.
C 68.88%, H 9.37%, N 2.77%, O 18.98%.

Description and references

Cardiotonic principle from the bark of Erythrophleum couminga Baillon, Leguminosae. Isoln: Ruzicka et al., Helv. Chim. Acta 24, 63 (1941). Structure: Ruzicka et al., ibid. 1449.

Chemical structure

Properties

Thin shiny needles from ether, mp 142°. [α]D20 -70°. Sol in methanol, ethanol, acetone, acetic acid, benzene, chloroform. Practically insol in water, hexane, ether.

Derivative

Hydrochloride.
C29H47NO6.HCl; mol wt 542.15.
C 64.25%, H 8.92%, N 2.58%, O 17.71%, Cl 6.54%.

Properties

Crystals from ethanol + ether, mp 195°. Sol in ethanol, water.