Iodinin
Title: Iodinin
CAS Registry Number: 68-81-5
CAS Name: 1,6-Phenazinediol 5,10-dioxide
Additional Names: 1,5-dihydroxyphenazine N,N¢-dioxide
Molecular Formula: C12H8N2O4
Molecular Weight: 244.20
Percent Composition: C 59.02%, H 3.30%, N 11.47%, O 26.21%
Literature References: Antibiotic pigment from Chromobacterium iodinum: Clemo, McIlwain, J. Chem. Soc. 1938, 479; Hegedüs in Emil Barell Jubilee Volume (1946), p 388; from Waksmania aerata and Pseudomonas iodinum: Gerber, Lechevalier, Biochemistry 3, 598 (1964). Structure: Clemo, Daglish, J. Chem. Soc. 1950, 1481. Synthesis: Matsumura, Takeda, Nippon Kagaku Zasshi 81, 515 (1960), C.A. 56, 470a (1962). Biosynthetic studies on incorporation of shikimic acid, q.v., into iodinin: U. Hollstein et al., Tetrahedron Lett. 1978, 2987; R. B. Herbert et al., J. Chem. Soc. Perkin Trans. 1 1979, 2411; T. Etherington et al., ibid. 2416.
Properties: Purple crystals with coppery sheen from chloroform, dec 236°. pK 12.5. Stable in acid, unstable in alkali. Sol in benzene, toluene, xylene, carbon disulfide, chloroform, ethyl acetate. Slightly sol in hot alc. Practically insol in cold alc, ether, acetic acid, petr ether, amyl alcohol. Insol in water. Sol in concd sulfuric acid and in glacial acetic acid with red color. Sol in NaOH solns giving brilliantly blue solns which deposit green crystals of the unstable sodium deriv.
pKa: pK 12.5

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