Daphnoline

Title: Daphnoline
CAS Registry Number: 479-36-7
CAS Name: 6,6¢-Dimethoxy-2-methyloxyacanthan-7,12¢-diol
Additional Names: trilobamine
Molecular Formula: C35H36N2O6
Molecular Weight: 580.67
Percent Composition: C 72.39%, H 6.25%, N 4.82%, O 16.53%
Literature References: From bark of Daphnandra micrantha Benth., Monimiaceae. Isoln: Pyman, J. Chem. Soc. 105, 1679 (1914). Identity with trilobamine: Bick et al., ibid. 1949, 2767. Structure: Bick et al., ibid. 1960, 4928.
Properties: Crystals from chloroform, mp 194-196°. [a]D +459° (c = 0.3 in chloroform). uv max (methanol): 285 nm (log e 3.9). Practically insol in water, ethyl acetate, acetone, ether, petr ether. Sparingly sol in methanol, ethanol, xylene, hot chloroform sol in dil acids, cold aq 5% sodium hydroxide.
Melting point: mp 194-196°
Optical Rotation: [a]D +459° (c = 0.3 in chloroform)
Absorption maximum: uv max (methanol): 285 nm (log e 3.9)
Derivative Type: Daphnandrine
CAS Registry Number: 1183-76-2
CAS Name: 6,6¢,12¢-Trimethoxy-2-methyloxyacanthan-7-ol
Molecular Formula: C36H38N2O6
Molecular Weight: 594.70
Percent Composition: C 72.71%, H 6.44%, N 4.71%, O 16.14%
Properties: Needles from methanol, dec 270°. [a]D16 +480° (c = 1.2 in chloroform). uv max (methanol): 284 nm (log e 3.92). Practically insol in hot water, ethyl acetate, acetone, ether, petr ether. Sparingly sol in hot methanol, ethanol, xylene, cold chloroform; sol in hot chloroform.
Optical Rotation: [a]D16 +480° (c = 1.2 in chloroform)
Absorption maximum: uv max (methanol): 284 nm (log e 3.92)
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