4333. Galactoflavin

Nomenclature

CAS number: 5735-19-3
1-Deoxy-1-(3,4-dihydro-7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10(2H)-yl)-d-galactitol; 7,8-dimethyl-10-(d-galacto-2,3,4,5,6-pentahydroxyhexyl)benzo[g]pteridine-2,4(3H,10H)-dione; 7,8-dimethyl-10-(d-galacto-2,3,4,5,6-pentahydroxyhexyl)isoalloxazine; 7,8-dimethyl-10-(d-1′-dulcityl)isoalloxazine; 6,7-dimethyl-9-(d-1′-dulcityl)isoalloxazine; 6,7-dimethyl-9-(1-deoxy-d-galactitol-1-yl)isoalloxazine.
C18H22N4O7; mol wt 406.39.
C 53.20%, H 5.46%, N 13.79%, O 27.56%.

Description and references

Prepd from 1-deoxy-1-(3,4-dimethyl-6-phenylazo)anilino-d-galactitol and barbituric acid: Berezovskii, Eremenko, Zh. Obshch. Khim. 32, 4056 (1962), C.A. 59, 736b (1963). Structure: Emerson et al., J. Biol. Chem. 160, 165 (1945). Pharmacology: Lane, Brindley, Proc. Soc. Exp. Biol. Med. 116, 57 (1964). Produces congenital malformations in animals: Nelson et al., J. Nutr. 58, 125 (1956); Miller et al., J. Biol. Chem. 237, 968 (1962); Mackler, Pediatrics 43, 915 (1969).

Chemical structure

Properties

Yellow crystals, dec 260°. Absorption max: 223, 267, 370, 445 nm (ε 2730, 28100, 9100, 10800). Compd has yellow-green fluorescence in water.

Use

Riboflavine antagonist.