9697. Trilobine

Nomenclature

CAS number: 6138-73-4
(1′α)-6′,7-Epoxy-6,12′-dimethoxy-2′-methyloxyacanthan.
C35H34N2O5; mol wt 562.65.
C 74.71%, H 6.09%, N 4.98%, O 14.22%.

Description and references

From root of Cocculus trilobus DC. and C. sarmentosus Diels, Menispermaceae: Tomita et al., J. Pharm. Soc. Jpn. 48, 83 (1928); 50, 127 (1930); 62, 468, 481 (1942). Structure: Kondo, Tomita, Ann. 497, 104 (1932); Inubushi, Nomura, Tetrahedron Lett. 1962, 1133. Total synthesis of trilobine and isotrilobine: Y. Inubushi et al., Chem. Pharm. Bull. 25, 1636 (1977).

Chemical structure

Properties

Crystals from benzene, mp 237°. [α]D +307° (chloroform). Practically insol in water. Sparingly sol in alcohol, acetone, ether. Sol in chloroform.

Derivative

Isotrilobine.

Nomenclature

CAS number: 26195-62-0
Homotrilobine; N-methyltrilobine.
C36H36N2O5; mol wt 576.68.
C 74.98%, H 6.29%, N 4.86%, O 13.87%.

Properties

Crystals from acetone, mp 215°. [α]D +317° (chloroform).