283. Alloxantin

Nomenclature

CAS number: 76-24-4
5,5′-Dihydroxy-[5,5′-bipyrimidine]-2,2′,4,4′,6,6′(1H,1′H,3H,3′H,5H,5′H)-hexone; 5,5′-dihydroxy-5,5′-bibarbituric acid; uroxin.
C8H6N4O8; mol wt 286.16.
C 33.58%, H 2.11%, N 19.58%, O 44.73%.

Description and references

Prepd from uric acid: Nightingale, Org. Synth. coll. vol. III, 42 (1955); from alloxan monohydrate: Tipson, ibid. coll. vol. IV, 25 (1963). Structure: Singh, Acta Crystallogr. 19, 767 (1965).

Chemical structure

Derivative

Dihydrate.

Properties

Cryst powder. On exposure to air becomes red. Becomes yellow at 225°; dec at 253-255°. Sparingly sol in cold water, alcohol or ether. Its aq soln is acid; reduces Ag salts and gives a blue ppt with Ba(OH)2 soln. Keep tightly closed. Emits toxic fumes upon decompn.

Caution

Ingestion causes disturbed carbohydrate metabolism leading to diabetes, cf. Dangerous Properties of Industrial Materials, N. I. Sax, Ed. (Van Nostrand Reinhold, New York, 4th ed., 1975) p 366.