Title: Veatchine
CAS Registry Number: 76-53-9
Molecular Formula: C22H33NO2
Molecular Weight: 343.50
Percent Composition: C 76.92%, H 9.68%, N 4.08%, O 9.32%
Literature References: From bark of Garrya veatchii Kellogg, Garryaceae, where it occurs together with garryine and other alkaloids: Oneto, J. Am. Pharm. Assoc. 35, 204 (1946); Wiesner et al., Can. J. Chem. 30, 608 (1952). Structure: Wiesner et al., J. Am. Chem. Soc. 76, 6068 (1954); Pelletier, ibid. 82, 2398 (1960). Stereochemistry: Vorbrüggen, Djerassi, Tetrahedron Lett. 1961, 119; J. Am. Chem. Soc. 84, 2990 (1962). Coexistence of epimers found in crystal and molecular structure: S. W. Pelletier et al., ibid. 100, 7976 (1978). 13C-NMR study of epimers: N. V. Mody, S. W. Pelletier, Tetrahedron 34, 2421 (1978). Racemic syntheses and resolution: Nagata et al., ibid. 86, 929 (1964), 89, 1499 (1967); Guthrie et al., Collect. Czech. Chem. Commun. 31, 602 (1966). Total synthesis of optically active form: Wiesner et al., Experientia 26, 471 (1970).
Properties: Crystals from dil acetone, mp 119-120°. Bitter taste. pH 11.5. [a]D27.5 -69.01° (c = 1.06 in ethanol). Readily sol in water, ethanol.
Melting point: mp 119-120°
Optical Rotation: [a]D27.5 -69.01° (c = 1.06 in ethanol)
Derivative Type: Hydrochloride
Molecular Formula: C22H33NO2.HCl
Molecular Weight: 379.96
Percent Composition: C 69.54%, H 9.02%, N 3.69%, O 8.42%, Cl 9.33%
Properties: Crystals from abs ethanol + ether, dec 267-271°. Sol in water.
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