12-01939. Cassamine [Archived]

Nomenclature

CAS number: 471-71-6
[1S-(1α,4aα,4bβ,7E,8β,8aα,10aβ)]-7-[2-[2-(Dimethylamino)ethoxy]-2-oxoethylidene]tetradecahydro-1,4a,8-trimethyl-9-oxo-1-phenanthrenecarboxylic acid methyl ester; (E)-13-(carboxymethylene)-14α-methyl-7-oxopodocarpan-16-oic acid 13-[2-(dimethylamino)ethyl]methyl ester.
C25H39NO5; mol wt 433.58.
C 69.25%, H 9.07%, N 3.23%, O 18.45%.

Description and references

Extracted from the bark of Erythrophleum guineense G. Don., Leguminosae. Isoln: Engel, Tondeur, Helv. Chim. Acta 32, 2364 (1949). Structure: Arya, Engel, ibid. 44, 1650 (1961).

Chemical structure

Properties

Crystals from pentane, mp 86-87°. [α]D20 56° (ethanol). uv max: 225 nm (log ε 4.2). Soluble in petr ether.

Derivative

Hydrochloride.
C25H39NO5.HCl; mol wt 470.04.
C 63.88%, H 8.58%, N 2.98%, O 17.02%, Cl 7.54%.

Properties

Crystals from acetone, dec 214-217°. [α]D17 48° (c = 0.65 in water).

Derivative

Sulfate.
C25H39NO5.H2SO4; mol wt 531.66.
C 56.48%, H 7.77%, N 2.63%, O 27.08%, S 6.03%.

Properties

Crystals from alcohol + ether, mp 191-194°. [α]D17 49.5° (c = 0.47 in water).

Status

This monograph has been retired and is no longer subject to revision or update.