3413. Domesticine

Nomenclature

CAS number: 476-71-1
(6aS)-5,6,6a,7-Tetrahydro-2-methoxy-6-methyl-4H-benzo[de][1,3]benzodioxolo[5,6-g]quinolin-1-ol; 2-methoxy-9,10-(methylenedioxy)-6aα-aporphin-1-ol; 1-hydroxy-2-methoxy-9,10-methylenedioxyaporphine.
C19H19NO4; mol wt 325.36.
C 70.14%, H 5.89%, N 4.30%, O 19.67%.

Description and references

In Nandina domestica Thunb., Berberidaceae. Isoln: Kitasato, Shishido, Ann. 527, 176 (1937). Syntheses: Govindachari et al., Indian J. Chem. 7, 841 (1969); Kessar et al., ibid. 8, 468 (1970); Kametani et al., J. Chem. Soc. C 1971, 2446, 2712; eidem, Chem. Pharm. Bull. 21, 766 (1973); Horii et al., ibid. 22, 583 (1974); Hoshino et al., ibid. 23, 2048 (1975).

Chemical structure

Properties

From methanol + water, mp 115-116°; from abs methanol or benzene, mp 84-85°; dried at 60° over P2O5, mp 152-153°. Easily oxidized in air. uv max (ethanol): 221, 283, 310 nm (log ε 4.56, 4.01, 4.17). Very sol in chloroform, sol in hot alc, ethyl acetate, acetic acid, alkalies; slightly sol in ether. Practically insol in water.

Derivative

Methyl ether.

Nomenclature

Nantenine; domestine; epidicentrine.

Properties

mp 139°. [α]D18 +102° (c = 0.528 in chloroform).

Derivative

dl-Form.

Properties

Needles from methanol, mp 185-186° (dec).