Title: Colchiceine
CAS Registry Number: 477-27-0
CAS Name: N-[(7S)-5,6,7,9-Tetrahydro-10-hydroxy-1,2,3-trimethoxy-9-oxobenzo[a]heptalen-7-yl]acetamide
Additional Names: 7-acetamido-10-hydroxy-1,2,3-trimethoxy-6,7-dihydrobenzo[a]heptalen-9(5H)-one
Molecular Formula: C21H23NO6
Molecular Weight: 385.41
Percent Composition: C 65.44%, H 6.02%, N 3.63%, O 24.91%
Literature References: Deriv of colchicine, q.v., isolated from Colchicum autumnale L., Liliaceae: Santavy, Macák, Collect. Czech. Chem. Commun. 19, 805 (1954). Toxicity data: B. Goldberg et al., Cancer 3, 124 (1950). Structure and synthesis: Nakamura, Chem. Pharm. Bull. 10, 299 (1962). Circular dichroism: J. Hrbek et al., Collect. Czech. Chem. Commun. 47, 2258 (1982). Effect on antibody response induced in vitro: J. Sterzl et al., Folia Microbiol. 27, 256 (1982).
Properties: Yellow crystals from dioxane + ether, mp 178-179°. [a]D25 -255.1° (c = 1 in chloroform). uv max (95% ethanol): 351, 244 nm (log e 4.28, 4.51). Slightly sol in water; freely sol in alcohol, chloroform. Almost insol in benzene, ether.
Melting point: mp 178-179°
Optical Rotation: [a]D25 -255.1° (c = 1 in chloroform)
Absorption maximum: uv max (95% ethanol): 351, 244 nm (log e 4.28, 4.51)
Derivative Type: Ethyl ether
Molecular Formula: C23H27NO6
Molecular Weight: 413.46
Percent Composition: C 66.81%, H 6.58%, N 3.39%, O 23.22%
Properties: Needles from ethyl acetate + ether, mp 135-139°. [a]D25 -129.4° (c = 1 in chloroform). uv max (95% ethanol): 351, 243.5 nm (log e 4.21, 4.45). LD50 i.p. in mice: 84 mg/kg (Goldberg).
Melting point: mp 135-139°
Optical Rotation: [a]D25 -129.4° (c = 1 in chloroform)
Absorption maximum: uv max (95% ethanol): 351, 243.5 nm (log e 4.21, 4.45)
Toxicity data: LD50 i.p. in mice: 84 mg/kg (Goldberg)
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