2819. Daphnoline

Nomenclature

CAS number: 479-36-7
6,6′-Dimethoxy-2-methyloxyacanthan-7,12′-diol; trilobamine.
C35H36N2O6; mol wt 580.67.
C 72.39%, H 6.25%, N 4.82%, O 16.53%.

Description and 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.

Chemical structure

Properties

Crystals from chloroform, mp 194-196°. [α]D +459° (c = 0.3 in chloroform). uv max (methanol): 285 nm (log ε 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.

Derivative

Daphnandrine.

Nomenclature

CAS number: 1183-76-2
6,6′,12′-Trimethoxy-2-methyloxyacanthan-7-ol.
C36H38N2O6; mol wt 594.70.
C 72.71%, H 6.44%, N 4.71%, O 16.14%.

Properties

Needles from methanol, dec 270°. [α]D16 +480° (c = 1.2 in chloroform). uv max (methanol): 284 nm (log ε 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.