Alloxantin
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Preferred IUPAC name
5,5-Dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione
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| Other names
5,5-Dihydroxybarbituric acid
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| Identifiers | |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.000.057 |
| MeSH | Alloxan |
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PubChem CID
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| Properties | |
| C4H4N2O5 | |
| Molar mass | 160.07 g/mol |
| Appearance | pale yellow solid |
| Density | 1.639 g/cm3 (anhydrous) |
| Melting point | 254 °C (489 °F; 527 K) (decomposition) |
| 0.29 g/100 mL | |
| Hazards | |
| Safety data sheet | MSDS |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
Alloxan, sometimes referred to as alloxan hydrate, refers to the organic compound with the formula OC(N(H)CO)2C(OH)2. It is classified as a derivative of pyrimidine. The anhydrous derivative (OC(N(H)CO)2CO is also known as well as a dimeric derivative. These are some of the earliest known organic compounds. They also exhibit a variety of biological activities.
The compound was discovered by Justus von Liebig and Friedrich Wöhler. It is one of the oldest named organic compounds. It was originally prepared in 1818 by Brugnatelli (1761-1818) and was named in 1838 by Wöhler and Liebig. The name "Alloxan" emerged from an amalgamation of the words "allantoin" and "Oxalsäure" (oxalic acid). The alloxan model of diabetes was first described in rabbits by Dunn, Sheehan and McLetchie in 1943. The name is derived from allantoin, a product of uric acid excreted by the fetus into the allantois, and oxaluric acid derived from oxalic acid and urea, found in urine.
Alloxan was used in the production of the purple dye murexide, discovered by Carl Wilhelm Scheele in 1776. Murexide is the product of the complex in-situ multistep reaction of alloxantin and gaseous ammonia. Murexide results from the condensation of the unisolated intermediate uramil with alloxan, liberated during the course of the reaction.
Scheele sourced uric acid from human calculi (such as kidney stones) and called the compound lithic acid. William Prout investigated the compound in 1818 and he used boa constrictor excrement with up to 90% ammonium acid urate.
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