5599. Lumiflavine

Nomenclature

CAS number: 1088-56-8
7,8,10-Trimethylbenzo[g]pteridine-2,4(3H,10H)-dione; 7,8,10-trimethylisoalloxazine.
C13H12N4O2; mol wt 256.26.
C 60.93%, H 4.72%, N 21.86%, O 12.49%.

Description and references

Irradiation product of riboflavine. Isoln: Warburg, Christian, Biochem. Z. 266, 377 (1933). Structure: Kuhn, Rudy, Ber. 67, 1298 (1934). Prepn: Tishler, Wellman, US 2417143 (1947 to Merck & Co.); Birch, Moye, J. Chem. Soc. 1958, 2622; Yoneda et al., Chem. Pharm. Bull. 20, 1832 (1972).

Chemical structure

Properties

Orange crystals from 12% acetic acid, mp 320°. Purified by sublimation in vacuum, mp 330°. Freely sol in chloroform; very sparingly sol in water and most organic solvents. Aq and chloroformic solns fluoresce green. uv max: 269, 355, 445 nm (ε 38,800, 11,700, 11,800) in 0.1N NaOH and 264, 373, 440 nm (ε 34,700, 11,400, 10,400) in 0.1N HCl.