Alloxan

Alloxan

Names
Preferred IUPAC name 5,5-Dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione
Other names 5,5-Dihydroxybarbituric acid
Identifiers
CAS Number	2244-11-3 N 50-71-5 (Anhydrous) N
ChEBI	CHEBI:76451 N
ChEMBL	ChEMBL1096009 Y ChEMBL1697709 Y
ChemSpider	5577 Y
ECHA InfoCard	100.000.057
MeSH	Alloxan
PubChem	5781
UNII	6SW5YHA5NG Y
InChI InChI=1S/C4H2N2O4/c7-1-2(8)5-4(10)6-3(1)9/h(H2,5,6,8,9,10) Y Key: HIMXGTXNXJYFGB-UHFFFAOYSA-N Y InChI=1/C4H2N2O4/c7-1-2(8)5-4(10)6-3(1)9/h(H2,5,6,8,9,10) Key: HIMXGTXNXJYFGB-UHFFFAOYAQ
Properties
Chemical formula	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)
Solubility in water	0.29 g/100 mL
Hazards
Safety data sheet	MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
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.