Title: Epiquinidine
CAS Registry Number: 572-59-8
CAS Name: (9R)-6¢-Methoxycinchonan-9-ol
Molecular Formula: C20H24N2O2
Molecular Weight: 324.42
Percent Composition: C 74.04%, H 7.46%, N 8.63%, O 9.86%
Literature References: Occurs in cinchona bark. Isoln from quinoidine: Dirscherl, Thron, Ann. 521, 48 (1938). By epimerization of quinine or quinidine: Rabe, Höter, J. Prakt. Chem. 154, 66 (1940). Stereochemistry: Prelog, Zalán, Helv. Chim. Acta 27, 535, 545 (1944); Prelog, Häfliger, ibid. 33, 2021 (1950); Roth, Pharmazie 16, 257 (1961). Synthesis: Grethe et al., Helv. Chim. Acta 55, 1044 (1972); Gutzwiller, Uskokovic, ibid. 56, 1494 (1973).
Properties: Lustrous leaflets from ether, mp 111-113°. [a]D25 +107.8° (c = 1.02 in ethanol). Freely sol in alcohol; moderately sol in ether. Shows more blue fluorescence in H2SO4 than quinidine or quinine. Forms a double sulfate with epiquinine.
Melting point: mp 111-113°
Optical Rotation: [a]D25 +107.8° (c = 1.02 in ethanol)
Derivative Type: Dihydrochloride
Molecular Formula: C20H24N2O2.2HCl
Molecular Weight: 397.34
Percent Composition: C 60.46%, H 6.60%, N 7.05%, O 8.05%, Cl 17.85%
Properties: Crystals from alc, dec 195-196°. [a]D20 +46° (c = 0.8 in 99% alc).
Optical Rotation: [a]D20 +46° (c = 0.8 in 99% alc)
Derivative Type: Neutral dibenzoyl-d-tartrate
Molecular Formula: (C20H24N2O2)2.C18H14O8
Molecular Weight: 1007.13
Percent Composition: C 69.17%, H 6.20%, N 5.56%, O 19.06%
Properties: Crystals from alcohol or acetone, dec 166-167°. [a]D21 +3.7° (4:1 alcohol + chloroform).
Optical Rotation: [a]D21 +3.7° (4:1 alcohol + chloroform)
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