Allantoxanic acid

The structure (5) originally proposed by Ponomarev appeared to be confirmed by the conversion of dihydrooxonic acid to allantoin performed by Biltz and Giesler. Biltz and RobP showed later that oxonic acid is identical with allantoxanic acid obtained on oxidation of allantoin. Since that time both these trivial names are in usage. 

The conversion of uric acid (1) to cyanuric acid (4) can be achieved in about 50% yield by reaction with alkaline permanganate1 or with strongly alkaline hydrogen peroxide.2,3 The mechanism of this oxidation has been investigated using isotopic labeling experiments 4,5 30 allantoxanic acid (4,6-dioxo-l,4,5,6-tetrahydro-l,3,5-triazine-2-carboxylic acid, 2) and 1,3,5-triazine-2,4(l//,3//)-dione (5-azauracil, allantoxaidine, 3) are proposed as common intermediates. 

Oxidative degradation of uric acid affords allantoxanic acid which decarboxylates to give... 

Brandenberger, H. 1954. The oxidation of uric acid to oxonic acid (allantoxanic acid) and its application in tracer studies of uric acid biosynthesis. Biochim. Biophys. Acta. 15 108. 

The name 5-azaorotic acid should be given to allantoxanic (oxonic) acid but it is not yet commonly used. The elucidation of the correct structure of this compound was closely linked to the solution of the course of oxidation of uric acid mentioned earlier. 

The excretion of uric acid in the urine under various experimental conditions is displayed in Fig. 2. The open bars show the excretion of uric acid in the control group receiving allantoxan-amide alone. In the collection period of 1 - 6 hours, there was no major difference in uric acid excretion between control group and rats having simultaneously received allantoxanamide and allo-purinol in doses of 10, 25, 50 and 100 mg/kg. 

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