12-08122. Puberulonic Acid [Archived]
Nomenclature
CAS number: 82-83-7
5,6,7-Trihydroxy-1H-cyclohepta[c]furan-1,3,4-trione; 4,5,6-trihydroxy-7-oxo-1,3,5-cycloheptatriene-1,2-dicarboxylic
anhydride. C9H4O7; mol wt 224.12.
C 48.23%, H 1.80%, O 49.97%.
Description and references
Antibiotic substance produced by Penicillium puberulum, P. aurantiovirens, P. johannioli, P. cyclopium viridicatum. Isoln: Birkinshaw, Raistrick, Biochem. J. 26, 441 (1932); Barger, Dorrer, ibid. 28, 11 (1934). Structure: McGowan, Chem. Ind. (London) 1947, 205; Aulin-Erdtman, Acta Chem. Scand. 4, 1325 (1950). Johnson et al., J. Chem. Soc. 1951, 1139. Synthesis: Nozoe et al., Bull. Chem. Soc. Jpn. 33, 1071 (1960). Biosynthesis: Ferritti, Richards, Proc. Natl. Acad. Sci. USA 46, 1438 (1960); A. I. Scott, E. Lee, Chem. Commun. 1972, 655. Review: Nozoe, Fortschr. Chem. Org. Naturst. 13, 232-301 (1956).
Properties
Yellow plates, dec 296°. Sol in water. The yellow color of an aq soln changes to pink on neutralization and disappears altogether when the soln is made alkaline.Derivative
Sodium salt.Properties
Crystals from ethanol, freely sol in water.Status
This monograph has been retired and is no longer subject to revision or update.