Title: Catharanthine
CAS Registry Number: 2468-21-5
CAS Name: 3,4-Didehydroibogamine-18-carboxylic acid methyl ester
Additional Names: 7-ethyl-9,10,12,13-tetrahydro-6,9-methano-5H-pyrido[1¢,2¢:1,2]azepino[4,5-b]indole-6(6aH)-carboxylic acid methyl ester
Molecular Formula: C21H24N2O2
Molecular Weight: 336.43
Percent Composition: C 74.97%, H 7.19%, N 8.33%, O 9.51%
Literature References: Precursor of vinblastine-type alkaloids. Isoln from Vinca rosea Linn. (Catharanthus roseus G. Don.) Apocynaceae: M. Gorman et al., J. Am. Pharm. Assoc. Sci. Ed. 48, 256 (1959); G. H. Svoboda et al., ibid. 659. Structure: N. Neuss, M. Gorman, Tetrahedron Lett. 1961, 206. Abs config: K. Bláha et al., ibid. 1972, 2763. Synthesis of (±)-form: A. A. Qureshi, A. I. Scott, Chem. Commun. 1968, 947, 948; A. R. Battersby et al., ibid. 951; G. Büchi et al., J. Am. Chem. Soc. 92, 999 (1970); J. P. Kutney, F. Bylsma, Helv. Chim. Acta 58, 1672 (1975); B. M. Trost et al., J. Org. Chem. 44, 2052 (1979); T. Imanishi et al., Tetrahedron Lett. 21, 3285 (1980).
Properties: Crystals from methanol, mp 126-128°. uv max (ethanol): 226, 284, 292 nm (log e 4.56, 3.92, 3.88). [a]D27 +29.8° (CHCl3). pKa¢ 6.8.
Melting point: mp 126-128°
pKa: pKa¢ 6.8
Optical Rotation: [a]D27 +29.8° (CHCl3)
Absorption maximum: uv max (ethanol): 226, 284, 292 nm (log e 4.56, 3.92, 3.88) |