Title: Toxoflavin
CAS Registry Number: 84-82-2
CAS Name: 1,6-Dimethylpyrimido[5,4-e]-1,2,4-triazine-5,7(1H,6H)-dione
Additional Names: 1,6-dimethyl-5,7-dioxo-1,5,6,7-tetrahydropyrimido[5,4-e]-as-triazine; xanthothricin
Molecular Formula: C7H7N5O2
Molecular Weight: 193.16
Percent Composition: C 43.53%, H 3.65%, N 36.26%, O 16.57%
Literature References: Highly toxic antibiotic from cultures of Pseudomonas cocovenenans which also produces bongkrekic acid, q.v. Isoln: van Veen, Mertens, Rec. Trav. Chim. 53, 257, 398 (1934); R. A. Machlowitz et al., Antibiot. Chemother. 4, 259 (1954). Structure: Van Damm et al., Rec. Trav. Chim. 79, 255 (1960). Synthesis: Daves et al., J. Am. Chem. Soc. 83, 3904 (1961); 84, 1724 (1962); Yoneda et al., Tetrahedron Lett. 1971, 851. Mode of action: Latuasan, Berends, Biochim. Biophys. Acta 52, 502 (1961). Biosynthesis: Levenberg, Linton, J. Biol. Chem. 241, 846 (1966). Production by Burkholderia glumae and pathogenicity to rice seedlings: K. Yoneyama et al., Ann. Phytopathol. Soc. Jpn. 64, 91 (1998).
Properties: Bright yellow platelets from propanol, dec 172-173°. uv max: 257.5, 394 nm (e 16400, 2500). Acts as a pH indicator with a sharp loss of color at pH 10.5, but is destroyed by alkali. Sol in water, chloroform, ethyl acetate, ethanol. LD50 in mice (mg/kg): 1.7 i.v.; 8.4 orally (Machlowitz).
Absorption maximum: uv max: 257.5, 394 nm (e 16400, 2500)
Toxicity data: LD50 in mice (mg/kg): 1.7 i.v.; 8.4 orally (Machlowitz) |