4732. Homochelidonine

Nomenclature

CAS number: 476-33-5
4b,5,6,11b,12,13-Hexahydro-1,2-dimethoxy-12-methyl[1,3]benzodioxolo[5,6-c]phenanthridin-5-ol; α-homochelidonine.
C21H23NO5; mol wt 369.41.
C 68.28%, H 6.28%, N 3.79%, O 21.66%.

Description and references

From root of Chelidonium majus L., Papaveraceae: Schmidt, Selle, Arch. Pharm. 228, 441 (1890). Structure: Spth, Kuffner, Ber. 64, 1123 (1931); H. W. Bersch, Arch. Pharm. 291, 491 (1958). Total synthesis: I. Ninomiya et al., Heterocycles 7, 137 (1977).

Chemical structure

Properties

Orthorhombic prisms from ethyl acetate, mp 182°. [α]D +118° (alc). Very sol in chloroform. Sol in alcohol, acetic acid, ethyl acetate, dil mineral acids; sparingly sol in ether.