Corynanthine
Title: Corynanthine
CAS Registry Number: 483-10-3
CAS Name: (16b,17a)-17-Hydroxyyohimban-16-carboxylic acid methyl ester
Additional Names: rauhimbine
Molecular Formula: C21H26N2O3
Molecular Weight: 354.44
Percent Composition: C 71.16%, H 7.39%, N 7.90%, O 13.54%
Literature References: From bark of Pseudocinchona africana Chev., Corynanthe johimbe K. Schum., Rubiaceae and Rauwolfia serpentina (L.) Benth., Apocynaceae: Raymond-Hamet, Compt. Rend. 212, 305 (1941); Jorio, Ann. Chim. Farm. 1939, 50, C.A. 33, 93069 (1939); Le Hir et al., Ann. Pharm. Fr. 11, 546 (1953); Hofmann, Helv. Chim. Acta 37, 314 (1954). Identity with rauhimbine: idem, ibid. 849. Structure and stereochemistry: Janot et al., Bull. Soc. Chim. Fr. 1952, 1085; 1961, 637.
Properties: Stout prisms from acetone, dec 225-226°. [a]D19 -85° (c = 0.5 in pyridine). uv max (methanol): 226, 283, 290 nm (log e 4.56, 3.87, 3.79). Practically insol in water or petr ether. Sol in 40 parts of boiling chloroform, in 60 parts of boiling benzene, in 20 parts of boiling ethyl acetate, in 5 parts of boiling alcohol.
Optical Rotation: [a]D19 -85° (c = 0.5 in pyridine)
Absorption maximum: uv max (methanol): 226, 283, 290 nm (log e 4.56, 3.87, 3.79)
 
Derivative Type: O,N-Dibutyrylcorynanthine hydrochloride
Literature References: Prepn: Reiser et al., US 2975183 (1961 to Chemische Werke Albert).
Properties: Crystals from benzene, mp 208-210°.
Melting point: mp 208-210°
 
Derivative Type: O,N-Dipropionylcorynanthine hydrochloride
Literature References: Prepn: Reiser et al., loc. cit.
Properties: Crystals from isopropanol, mp 236-237°.
Melting point: mp 236-237°

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