7232. Phenicin

Nomenclature

CAS number: 128-68-7
2,2′-Dihydroxy-4,4′-dimethyl[bi-1,4-cyclohexadien-1-yl]-3,3′,6,6′-tetrone; 3,3′-dihydroxy-5,5′-dimethyl-2,2′-bi-p-benzoquinone; phoenicin.
C14H10O6; mol wt 274.23.
C 61.32%, H 3.68%, O 35.01%.

Description and references

Fungal pigment produced by Penicillium phoeniceum and P. rubrum: Friedheim, Helv. Chim. Acta 21, 1464 (1938); Charollais et al., Arch. Sci. 16, 474 (1963). Synthesis: Posternak et al., Helv. Chim. Acta 26, 2031 (1943); Musso, Beecken, Ber. 92, 1416 (1959); J. Kalamar et al., Helv. Chim. Acta 57, 2368 (1974). Biosynthesis: E. Steiner et al., ibid. 2377.

Chemical structure

Properties

Yellowish-brown crystals from alc, mp 230-231°. uv max (chloroform): 268, 406 nm (log ε 4.52, 3.36). Sparingly sol in water; freely sol in chloroform, acetic acid, hot alcohol. Very acidic solns are yellow, turning red at pH 1.6-3.6 and violet at pH 4.9-6.