2296. Cinnabarine
Nomenclature
CAS number: 146-90-7
2-Amino-9-hydroxymethyl-3-oxo-3H-phenoxazine-1-carboxylic
acid; 1-carboxy-2-amino-9-hydroxymethylphenoxazin-3-one; polystictine. C14H10N2O5; mol wt 286.24.
C 58.74%, H 3.52%, N 9.79%, O 27.95%.
Description and references
Antibiotic substance produced by the fungus Trametes cinnabarina Jacq.: Gripenberg, Acta Chem. Scand. 5, 590 (1951); from Coriolus sanguineus (Fr.) (Polystictus cinnabarinus Jacq.): Cavill et al., J. Chem. Soc. 1953, 525. Identity with polystictine: Gripenberg et al., Acta Chem. Scand. 11, 1485 (1957). Structure: Gripenberg, ibid. 12, 603 (1958); 13, 1305 (1959); Cavill et al., Tetrahedron 5, 275 (1959). Syntheses: Weinstein, Brattesani, J. Heterocycl. Chem. 4, 151 (1967); Sch"afer, Schlude, Tetrahedron Lett. 1968, 2161.
Properties
Red needles, dec 320°. Absorption max: 234, 430, 455 nm (log ε 4.2, 4.0, 4.0). Soly in acetone: 0.04% (20°); in dioxane: 0.1% (100°). Practically insol in ethanol, chloroform and dimethyl sulfoxide. Sol in cold concd HCl.Derivative
O-Methyl ether.C15H12N2O5; mol wt 300.27.
C 60.00%, H 4.03%, N 9.33%, O 26.64%.