Title: Domesticine
CAS Registry Number: 476-71-1
CAS Name: (6aS)-5,6,6a,7-Tetrahydro-2-methoxy-6-methyl-4H-benzo[de][1,3]benzodioxolo[5,6-g]quinolin-1-ol
Additional Names: 2-methoxy-9,10-(methylenedioxy)-6aa-aporphin-1-ol; 1-hydroxy-2-methoxy-9,10-methylenedioxyaporphine
Molecular Formula: C19H19NO4
Molecular Weight: 325.36
Percent Composition: C 70.14%, H 5.89%, N 4.30%, O 19.67%
Literature 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).
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 e 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.
Melting point: mp 115-116°; mp 84-85°; mp 152-153°
Absorption maximum: uv max (ethanol): 221, 283, 310 nm (log e 4.56, 4.01, 4.17)
Derivative Type: Methyl ether
Additional Names: Nantenine; domestine; epidicentrine
Properties: mp 139°. [a]D18 +102° (c = 0.528 in chloroform).
Melting point: mp 139°
Optical Rotation: [a]D18 +102° (c = 0.528 in chloroform)
Derivative Type: dl-Form
Properties: Needles from methanol, mp 185-186° (dec).
Melting point: mp 185-186°
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