6900. Ouabagenin
Nomenclature
CAS number: 508-52-1
(1β,3β,5β,11α)-1,3,5,11,14,19-Hexahydroxycard-20(22)-enolide; G-strophanthidin. C23H34O8; mol wt 438.51.
C 63.00%, H 7.82%, O 29.19%.
Description and references
Prepn from ouabain with HCl in cold acetone: Mannich, Siewert, Ber. 75, 737 (1942). Review of structure: Reichstein, Reich, Annu. Rev. Biochem. 15, 155 (1946). Proof of this structure: Tamm et al., Helv. Chim. Acta 40, 1469 (1957), cf. Experientia 13, 185 (1957); Turner, Meschino, J. Am. Chem. Soc. 80, 4862 (1958); Volpp, Tamm, Helv. Chim. Acta 42, 1408, 1418 (1959).
Derivative
Monohydrate.Properties
Clusters of needles from water, mp 235-238°. One gram dissolves in about 10 ml boiling water. At room temp the soly in water is <1%. Also sol in dil alcohol. Practically insol in abs alcohol, ether, and chloroform. Becomes anhydr at 100° in vacuo over P2O5. The anhydr compd is hygroscopic, mp 255-256°. [α]D17 +11.3° (c = 1.27).Derivative
Tetraacetylouabagenin trihydrate.C31H42O12.3H2O; mol wt 660.70.
C 56.35%, H 7.32%, O 36.32%.
Properties
Needles from 10% alcohol, mp 282-285°.Derivative
Dihydroouabagenin.C23H36O8.CH3OH; mol wt 472.57.
C 61.00%, H 8.53%, O 30.47%.