Title: Frequentin
CAS Registry Number: 29119-03-7
CAS Name: 6-(1,3-Heptadienyl)-3,4-dihydroxy-2-oxocyclohexanecarboxaldehyde
Molecular Formula: C14H20O4
Molecular Weight: 252.31
Percent Composition: C 66.64%, H 7.99%, O 25.36%
Literature References: Mold metabolite with antineoplastic and antibiotic activity; isolated from Penicillium frequentans Westling and P. palitans Westling: Curtis et al., Nature 167, 557 (1951); Birkinshaw, Biochem. J. 51, 271 (1952). Structure: Sigg, Helv. Chim. Acta 46, 1061 (1963). Effect on Ehrlich ascites carcinoma cells: J. Fuska et al., Int. Congr. Chemother., Proc., 7th, Prague, 1971 vol. 2 (Univ. Park Press, Baltimore, 1972) pp 97-98. Synthetic study: C. G. Unson, Diss. Abstr. B 39, 1296 (1978).
Properties: Needles from boiling water, mp 134.5°. When dissolved, exists as the 1-hydroxymethylene tautomer. [a]D22 +65° (c = 0.95 in CHCl3); [a]D22 +61° (c = 0.96 in methanol). uv max (dioxane): 290, 232 nm (log e 3.74, 4.52). Sol in acetone, dioxane; less sol in chloroform, ethanol, benzene; slightly sol in carbon tetrachloride, water.
Melting point: mp 134.5°
Optical Rotation: [a]D22 +65° (c = 0.95 in CHCl3); [a]D22 +61° (c = 0.96 in methanol)
Absorption maximum: uv max (dioxane): 290, 232 nm (log e 3.74, 4.52) |