Title: Cinnabarine
CAS Registry Number: 146-90-7
CAS Name: 2-Amino-9-hydroxymethyl-3-oxo-3H-phenoxazine-1-carboxylic acid
Additional Names: 1-carboxy-2-amino-9-hydroxymethylphenoxazin-3-one; polystictine
Molecular Formula: C14H10N2O5
Molecular Weight: 286.24
Percent Composition: C 58.74%, H 3.52%, N 9.79%, O 27.95%
Literature 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); Schäfer, Schlude, Tetrahedron Lett. 1968, 2161.
Properties: Red needles, dec 320°. Absorption max: 234, 430, 455 nm (log e 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.
Absorption maximum: Absorption max: 234, 430, 455 nm (log e 4.2, 4.0, 4.0)
Derivative Type: O-Methyl ether
Molecular Formula: C15H12N2O5
Molecular Weight: 300.27
Percent Composition: C 60.00%, H 4.03%, N 9.33%, O 26.64%
Properties: Orange red prisms from ethyl acetate + petr ether, mp 200-202°.
Melting point: mp 200-202°
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