2328. Citromycetin

Nomenclature

CAS number: 478-60-4
8,9-Dihydroxy-2-methyl-4-oxo-4H,5H-pyrano[3,2-c][1]benzopyran-10-carboxylic acid; frequentic acid.
C14H10O7; mol wt 290.23.
C 57.94%, H 3.47%, O 38.59%.

Description and references

Antibiotic substance produced by Penicillium frequentans Westling and P. vesiculosum Bainier and by Citromyces spp: Hetherington, Raistrick, Philos. Trans. R. Soc. London Ser. B 220, 209 (1931); Grove, Brian, Nature 167, 995 (1951). Structure: Robertson et al., J. Chem. Soc. 1951, 2013. Biosynthesis: Birch et al., ibid. 1958, 4576; Money, Nature 199, 592 (1963). Total synthesis: M. Yamauchi et al., J. Chem. Soc. Perkin Trans. 1 1987, 395.

Chemical structure

Derivative

Dihydrate.

Properties

Yellow crystals, effervescence at 155°, dec 290-300° (considerable antecedent blackening). Freely sol in ethanol; readily sol in aq sodium carbonate soln; sparingly sol in water, chloroform. Insol in benzene, hexane. Stable to acid and alkali at 100°.