12-08121. Puberulic Acid [Archived]

Nomenclature

CAS number: 99-23-0
3,4,6-Trihydroxy-5-oxo-1,3,6-cycloheptatriene-1-carboxylic acid.
C8H6O6; mol wt 198.13.
C 48.50%, H 3.05%, O 48.45%.

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; Corbett et al., ibid. 1949, 626; J. Chem. Soc. 1950, 6. Synthesis: Johns et al., ibid. 1954, 198. Biosynthesis: Ferretti, Richards, Proc. Natl. Acad. Sci. USA 46, 1438 (1960). Review: Nozoe, Fortschr. Chem. Org. Naturst. 13, 232-301 (1956).

Chemical structure

Properties

Cream-colored powder from water, mp 316-318°. Sublimes in high vacuum. Dibasic acid. uv max (water): 270, 350 nm (log ε 4.55, 3.86). Sol in hot water. Forms a sodium salt which is freely sol in water.

Status

This monograph has been retired and is no longer subject to revision or update.