2007. Cervicarcin

Nomenclature

CAS number: 18700-78-2
1,2,3,4-Tetrahydro-1,3,4,5,10-pentahydroxy-2-methyl-3-[(3-methyloxiranyl)carbonyl]-4a,9a-epoxyanthracen-9(10H)-one; 4a,9a-epoxy-3-(2,3-epoxybutyryl)-1,2,3,4,4a,9a-hexahydro-1,3,4,5,10-pentahydroxy-2-methylanthrone.
C19H20O9; mol wt 392.36.
C 58.16%, H 5.14%, O 36.70%.

Description and 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).

Chemical structure

Properties

Needles, mp 203-205° (dec). [α]D20 -144° (in ethanol). uv max: 227, 264, 323 nm (ε 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).