Corytuberine

Title: Corytuberine
CAS Registry Number: 517-56-6
CAS Name: (6aS)-5,6,6a,7-Tetrahydro-2,10-dimethoxy-6-methyl-4H-dibenzo[de,g]quinoline-1,11-diol
Additional Names: 2,10-dimethoxy-6aa-aporphine-1,11-diol; 1,11-dihydroxy-2,10-dimethoxyaporphine
Molecular Formula: C19H21NO4
Molecular Weight: 327.37
Percent Composition: C 69.71%, H 6.47%, N 4.28%, O 19.55%
Literature References: In Corydalis cava (L.) Schweigg & Körte (C. tuberosa DC), in Dicentra formosa (Andr.) Walp., Fumariaceae. Isoln: Späth, Berger, Ber. 64, 2038 (1931); Manske, Can. J. Res. 10, 521 (1934). Synthesis of (±)-form: Tomita, Kikkawa, JP 58 6466 (1958 to Shionogi), C.A. 54, 1584i (1960); T. Kametani, M. Ihara, J. Chem. Soc. Perkin Trans. 1 1980, 629. Biosynthesis studies: Blaschke, Biochem. Physiol. Alkaloide, Int. Symp., 4th, K. Mothes, Ed. (Akad.-Verlag, Berlin, 1972) pp 283-286. Biomimetric total synthesis: T. Kametani et al., Heterocycles 5, 175 (1976).
Derivative Type: Pentahydrate
Properties: Leaflets, plates, turning gray on exposure to light. mp 240° dec (dry). uv max (methanol): 227, 272, 311.5 nm. Sol in alc, hot water; slightly sol in ether, chloroform, ethyl acetate. [a]D20 +283° (alc). The dried crystals are hygroscopic and quickly attract 1 mol H2O from the air.
Melting point: mp 240° dec (dry)
Optical Rotation: [a]D20 +283° (alc)
Absorption maximum: uv max (methanol): 227, 272, 311.5 nm
Derivative Type: Hydrochloride
Molecular Formula: C19H21NO4.HCl
Molecular Weight: 363.84
Percent Composition: C 62.72%, H 6.09%, N 3.85%, O 17.59%, Cl 9.74%
Properties: Crystals from alcohol-ether, dec above 250°; [a]D20 +168°; sparingly sol in water.
Optical Rotation: [a]D20 +168°
Derivative Type: Methyl ether see Corydine
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