Cervicarcin
Title: Cervicarcin
CAS Registry Number: 18700-78-2
CAS Name: 1,2,3,4-Tetrahydro-1,3,4,5,10-pentahydroxy-2-methyl-3-[(3-methyloxiranyl)carbonyl]-4a,9a-epoxyanthracen-9(10H)-one
Additional Names: 4a,9a-epoxy-3-(2,3-epoxybutyryl)-1,2,3,4,4a,9a-hexahydro-1,3,4,5,10-pentahydroxy-2-methylanthrone
Molecular Formula: C19H20O9
Molecular Weight: 392.36
Percent Composition: C 58.16%, H 5.14%, O 36.70%
Literature References: Antineoplastic antibiotic produced by Streptomyces ogaensis: Okuma et al., J. Antibiot. 15A, 152, 247 (1962). Prepn: Sumiki et al., JP 64 7400 (1964 to Inst. Phys. & Chem. Res.). Structure: Marumo et al., J. Am. Chem. Soc. 86, 4507 (1964); eidem, Agric. Biol. Chem. 32, 209 (1968). Stereochemistry: eidem, ibid. 35, 1931 (1971). Activity studies: C. Itakura et al., J. Antibiot. 16A, 231 (1963).
Properties: Needles, mp 203-205° (dec). [a]D20 -144° (in ethanol). uv max: 227, 264, 323 nm (e 14200, 7800, 2600). pKa 9.0. Sol in acetone, lower alcohols, acetic acid, pyridine. Moderately sol in ethyl acetate, ethyl ether, chloroform, carbon tetrachloride. Slightly sol in water, benzene. Insol in petr ether, ligroin. Stable in neutral or acidic soln; unstable in alkaline soln. LD50 i.p. in mice: 48.5 mg/kg (Itakura).
Melting point: mp 203-205° (dec)
pKa: pKa 9.0
Optical Rotation: [a]D20 -144° (in ethanol)
Absorption maximum: uv max: 227, 264, 323 nm (e 14200, 7800, 2600)
Toxicity data: LD50 i.p. in mice: 48.5 mg/kg (Itakura)

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