Title: Corynantheine
CAS Registry Number: 18904-54-6
CAS Name: (16E)-16,17,18,19-Tetradehydro-17-methoxycorynan-16-carboxylic acid methyl ester
Additional Names: (E)-16,17,18,19-tetradehydro-17-methoxy-17,18-secoyohimban-16-carboxylic acid methyl ester
Molecular Formula: C22H26N2O3
Molecular Weight: 366.45
Percent Composition: C 72.11%, H 7.15%, N 7.64%, O 13.10%
Literature References: Isolated from Corynanthe johimbe K. Schum., and Pseudocinchona africana A. Cheval., Rubiaceae: Karrer et al., Helv. Chim. Acta 9, 1059 (1926); 35, 851 (1952). Structure: Janot et al., ibid. 34, 1207 (1951). Stereochemistry: Van Tamelen et al., J. Am. Chem. Soc. 79, 6426 (1957). Total synthesis of dl- form: Van Tamelen, Wright, Tetrahedron Lett. 1964, 295; eidem, J. Am. Chem. Soc. 91, 7349 (1969). Total synthesis of d-form: Autrey, Scullard, ibid. 90, 4917 (1968).
Properties: Crystals: a-form mp 103-107°; b-form mp 165-166°. [a]D +28° (c = 1 in methanol). uv max (methanol): 227, 280, 291 nm (log e 4.64, 3.82, 3.80).
Melting point: mp 103-107°; mp 165-166°
Optical Rotation: [a]D +28° (c = 1 in methanol)
Absorption maximum: uv max (methanol): 227, 280, 291 nm (log e 4.64, 3.82, 3.80)
Derivative Type: Hydrochloride
Molecular Formula: C22H26N2O3.HCl
Molecular Weight: 402.91
Percent Composition: C 65.58%, H 6.75%, N 6.95%, O 11.91%, Cl 8.80%
Properties: Needles from alcohol + ether, mp 194-206°. Also reported as mp 176-179°. [a]D20 +12° (water). Sol in alcohol, sparingly sol in water.
Melting point: mp 194-206°; mp 176-179°
Optical Rotation: [a]D20 +12° (water)
Derivative Type: Dihydrocorynantheine
Molecular Formula: C22H28N2O3
Molecular Weight: 368.47
Percent Composition: C 71.71%, H 7.66%, N 7.60%, O 13.03%
Properties: Total synthesis of dl-form: Van Tamelen, Hester, J. Am. Chem. Soc. 81, 3805 (1959); eidem, ibid. 91, 7342 (1969). Plates from alcohol + water, mp 177-177.5°. [a]D +28°.
Melting point: mp 177-177.5°
Optical Rotation: [a]D +28°
Derivative Type: Hydrochloride
Molecular Formula: C22H28N2O3.HCl
Molecular Weight: 404.93
Percent Composition: C 65.25%, H 7.22%, N 6.92%, O 11.85%, Cl 8.76%
Properties: mp 212-213°. Also reported as crystals from 95% ethanol-ethyl acetate, mp 242.2-243.3° (dec) (sealed tube), Van Tamelen, Hester, loc. cit. (1969).
Melting point: mp 212-213°; mp 242.2-243.3° (dec) (sealed tube), Van Tamelen, Hester, loc. cit. (1969)
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