Cupreine

Title: Cupreine
CAS Registry Number: 524-63-0
CAS Name: (8a,9R)-Cinchonan-6¢,9-diol
Additional Names: hydroxycinchonidine; ultraquinine
Molecular Formula: C19H22N2O2
Molecular Weight: 310.39
Percent Composition: C 73.52%, H 7.14%, N 9.03%, O 10.31%
Literature References: In bark and seeds of Remijia pedunculata Flueck., Rubiaceae. Isoln: Howard, Hodgkin, J. Chem. Soc. 41, 16 (1882). Separated from homoquinine by treatment with NaOH: Hesse, Ann. 230, 55 (1885). Reduction to hydrocupreine: Giemsa, Halberkann, Ber. 51, 1325 (1918). Conversion into cinchonidine: King, J. Chem. Soc. 1946, 523.
Properties: Monoclinic plates from alcohol, mp 202°. [a]D17 -176°, (methanol). pK1 6.57. Sol in alcohol, NaOH soln, but not in NH4OH. Sparingly sol in water, ether, chloroform, benzene, petr ether. The neutral salts give yellow aq solns; the acid salts remain colorless in aq soln.
Melting point: mp 202°
pKa: pK1 6.57
Optical Rotation: [a]D17 -176°
Derivative Type: Monomethyl ether see Quinine
Cupric Acetate Cupric Acetoarsenite Cupric Arsenite Cupric Bisglycinate Cupric Borate