10064. Xanthopterin

Nomenclature

CAS number: 119-44-8
2-Amino-1,5-dihydro-4,6-pteridinedione; 2-amino-4,6-pteridinediol; 2-amino-4,6-dihydroxypteridine; 2-amino-4,6-dihydroxypyrimido[4,5-b]pyrazine.
C6H5N5O2; mol wt 179.14.
C 40.23%, H 2.81%, N 39.09%, O 17.86%.

Description and references

Pigment first found in wings of butterflies. Widely distributed in insects and in animals. Has been separated from urine and from the crab. Isoln and structure: Schpf, Becker, Ann. 507, 266 (1933); 524, 55, 126 (1936); Schpf, Kottler, Ann. 539, 128 (1939); Wieland, Purrmann, Ann. 544, 163 (1940). See also Fukushima, Shiota, J. Biol. Chem. 247, 4549 (1972). Synthesis: Purrmann, Ann. 546, 98 (1940); 548, 284 (1941); Koschara, Z. Physiol. Chem. 277, 159 (1943); Totter, J. Biol. Chem. 154, 105 (1944); Elion et al., J. Am. Chem. Soc. 71, 741 (1949); Koschara, DE 859471 (1952 to Bayer), C.A. 52, 10222f (1958); Stuart, Wood, J. Chem. Soc. 1963, 4186. Facile synthesis: Taylor, Jacobi, J. Am. Chem. Soc. 95, 4455 (1973); Taylor et al., J. Org. Chem. 40, 2341 (1975). Exhibits tumor inhibitory properties.

Chemical structure

Derivative

Monohydrate.

Properties

Orange-yellow crystals, sinters around 360°, decomp above 410°. Practically insol in water. Freely sol in dil NH4OH and NaOH giving yellow solns and in 2N HCl giving colorless solns. uv max at pH 11: 255, 390 nm (E1%1cm 0.92, 0.355). Can be converted by yeast into folic acid.