4645. Hemipyocyanine

Nomenclature

CAS number: 528-71-2
1-Phenazinol; α-hydroxyphenazine; 1-hydroxy-5,10-diazoanthracene; pyoxanthose.
C12H8N2O; mol wt 196.20.
C 73.46%, H 4.11%, N 14.28%, O 8.15%.

Description and references

Found in old cultures of Pseudomonas pyocyanea. Isoln: Fordos, Compt. Rend. 56, 1128 (1863). Prepd from pyocyanine by the action of 2% NaOH: Wrede, Strack, Z. Physiol. Chem. 140, 12 (1924); by the reaction of pyrogallol monomethyl ether and o-phenylenediamine followed by demethylation of the formed α-methoxyphenazine: Surrey, Org. Synth. coll. vol. III, 753 (1955). Alternate syntheses: Hegedüs, Helv. Chim. Acta 33, 766 (1950); Vivian, Nature 178, 753 (1956).

Chemical structure

Properties

Yellow needles from benzene, mp 159-160°. Sublimes easily in vacuo. Slightly sol in hot water; freely sol in the usual organic solvents except petr ether. Sol in aq alkaline solns with purplish-red color which turns yellow on neutralization. Forms red salts with mineral acids.