Title: Garryine
CAS Registry Number: 561-51-3
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 Kellog, Garryaceae, where it occurs together with veatchine 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); Djerassi et al., ibid. 77, 4801 (1955). Stereochemistry: Solo, Pelletier, Chem. Ind. (London) 1960, 1108. Racemic syntheses and resolution: Masamune, J. Am. Chem. Soc. 86, 290 (1964); Nagata et al., ibid. 929, 89, 1499 (1967); Guthrie et al., Collect. Czech. Chem. Commun. 31, 602 (1966).
Derivative Type: Monohydrate
Properties: Crystals from dil acetone. Bitter taste, mp 74-82°. pK 8.70. [a]D27.5 -84.23° (c = 1.44 in ethanol). Sol in water, alcohol.
Melting point: mp 74-82°
pKa: pK 8.70
Optical Rotation: [a]D27.5 -84.23° (c = 1.44 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 263-268°. Soluble in water.
Status: This monograph has been retired and is no longer subject to revision or update. |