8287. Rubijervine
Nomenclature
CAS number: 79-58-3
(3β,12α)-Solanid-5-ene-3,12-diol; Δ5-3β,12α-dihydroxysolanidene; rubigervine. C27H43NO2; mol wt 413.64.
C 78.40%, H 10.48%, N 3.39%, O 7.74%.
Description and references
From various species of Veratrum, Liliaceae. Isoln: Wright, Luff, J. Chem. Soc. 35, 405 (1879); Salzberger, Arch. Pharm. 228, 462 (1890); Jacobs, Craig, J. Biol. Chem. 148, 41 (1943); Sato, Jacobs, ibid. 179, 623 (1949); Pelletier, Locke, J. Am. Chem. Soc. 79, 4531 (1957). Stereochemistry: H"ohne et al., Tetrahedron 22, 673 (1966). Comparative toxicity: O. Krayer et al., J. Pharmacol. Exp. Ther. 82, 167 (1944).
Properties
Solvated needles from alc, mp 240-246°. [α]D25 +19.0° (ethanol). Very sparingly sol in water. Sol in ethanol, methanol, benzene, chloroform. Slightly sol in ether, petr ether. Red color in concd H2SO4. Precipitated by digitonin. LD50 i.v. in mice: 70 mg/kg (Krayer).Derivative
Hydrobromide.C27H43NO2.HBr; mol wt 494.55.
C 65.57%, H 8.97%, N 2.83%, O 6.47%, Br 16.16%.
Properties
Needles from methanol + acetone, dec 265-270°.Therapeutic Category
Antifungal.