1890. Cassaidine
Nomenclature
CAS number: 26296-41-3
[1R-(1α,2E,4aα,4bβ,7β,8aα,10β,10aβ)]-(Dodecahydro-7,10-dihydroxy-1,4b,8,8-tetramethyl-2(1H)-phenanthrenylidene)acetic acid 2-(dimethylamino)ethyl ester; (E)-3β,7β-dihydroxy-14α-methyl-8β-podocarpane-Δ13,α-acetic acid 2-(dimethylamino)ethyl ester. C24H41NO4; mol wt 407.59.
C 70.72%, H 10.14%, N 3.44%, O 15.70%.
Description and references
Cardiotonic principle from the bark of Erythrophleum guineense G. Don., Leguminosae. Isoln and structure: Ruzicka, Dalma, Helv. Chim. Acta 23, 753 (1940); Engel, ibid. 42, 1127 (1959). Synthesis: Turner et al., J. Am. Chem. Soc. 88, 1766 (1966). Stereochemistry: Clarke et al., ibid. 88, 5865 (1966).
Properties
Prisms from acetone + ether, mp 139.5°. [α]D20 -98° (ethanol); [α]D20 -104° (0.1N HCl). Slightly sol in methanol, ethanol, acetone, acetic, chloroform. Practically insol in ether, benzene.Derivative
Oxalate.C24H41NO4.(COOH)2; mol wt 497.62.
C 62.75%, H 8.71%, N 2.81%, O 25.72%.