8378. Sarpagine
Nomenclature
CAS number: 482-68-8
Sarpagan-10,17-diol; raupine. C19H22N2O2; mol wt 310.39.
C 73.52%, H 7.14%, N 9.03%, O 10.31%.
Description and references
Isoln from Rauwolfia serpentina (L.) Benth., Apocynaceae: Stoll, Hofmann, Helv. Chim. Acta 36, 1143 (1953). Structure: Stauffacher et al., ibid. 40, 508 (1957); Poisson et al., Bull. Soc. Chim. Fr. 1957, 610; Biemann, J. Am. Chem. Soc. 83, 4801 (1961). Stereochemistry: Bartlett et al., ibid. 84, 622 (1962); Ohashi et al., Tetrahedron 19, 2241 (1963).
Properties
Needles from methanol or ethanol, long plates from acetone, dec >320°. [α]D20 +54° (c = 0.5 in pyridine). uv max (ethanol): 230, 278 nm (log ε 4.30, 3.92). One gram dissolves in 60 ml boiling ethanol, 250 ml boiling methanol, 400 ml boiling acetone. Practically insol in chloroform.Derivative
Hydrochloride.C19H22N2O2.HCl; mol wt 346.85.
C 65.79%, H 6.68%, N 8.08%, O 9.23%, Cl 10.22%.