1.02011-09-21 00:24:12 UTC2015-10-09 22:32:13 UTCFDB023068AlloxanAlloxan or mesoxalylurea is an organic compound based on a pyrimidine heterocyclic skeleton. This compound has a high affinity for water and therefore exists as the monohydrate. The compound was discovered by Justus von Liebig and Friedrich Wohler following the discovery of urea in 1828 and is one of the oldest named organic compounds that exist. 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. The original recipe for Alloxan was by oxidation of uric acid by nitric acid. Alloxan is a strong oxidizing agent and it forms a hemiacetal with its reduced reaction product dialuric acid (in which a carbonyl group is reduced to a hydroxyl group) which is called alloxantin. -- Wikipedia; Alloxane is a raw material for the production of the purple dye Murexide. Carl Wilhelm Scheele discovered the dye 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 intermdiate 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. Liebig and Wohler in the nineteenth century coined the name murexide for the dye after the Trunculus Murex which is the source of the Tyrian purple of antiquity. Primo Levi in his world famous novel The Periodic Table in chapter Nitrogen considers pythons as a source for alloxane on behalf of a lipstick producer but he is turned down by the director of the Turin zoo because the zoo already has lucrative contracts with cosmetics companies (his attempts with chicken dung end in misery). -- Wikipedia [HMDB]2,4,5,6-Pyrimidinetetrone2,4,5,6-Pyrimidintetron2,4,5,6-Pyrimidintetrone2,4,5,6-Tetraoxohexahydropyrimidine2,4,5,6(1H,3H)-Pyrimidinetetrone5-oxo-barbiturate5-oxo-barbituric acid5-Oxobarbitate5-Oxobarbitic acid5-Oxobarbituric acid5,6-DioxouracilalloxanAlloxan 7169Alloxan tetrahydratAlloxanemesoxalyl-UreaMesoxalylcarbamideMesoxalylureaNSC 7169PyrimidinetetroneC4H2N2O4142.0697142.0014565621,3-diazinane-2,4,5,6-tetronealloxan50-71-5O=C1NC(=O)C(=O)C(=O)N1InChI=1S/C4H2N2O4/c7-1-2(8)5-4(10)6-3(1)9/h(H2,5,6,8,9,10)HIMXGTXNXJYFGB-UHFFFAOYSA-N belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.PyrimidonesOrganic compoundsOrganoheterocyclic compoundsDiazinesPyrimidines and pyrimidine derivativesAliphatic heteromonocyclic compoundsAzacyclic compoundsCyclic ketonesHydrocarbon derivativesHydropyrimidinesOrganic carbonic acids and derivativesOrganic oxidesOrganonitrogen compoundsOrganopnictogen compoundsPropargyl-type 1,3-dipolar organic compounds2,5-dihydropyrimidineAliphatic heteromonocyclic compoundAzacycleCarbonic acid derivativeCarbonyl groupCyclic ketoneHydrocarbon derivativeHydropyrimidineKetoneOrganic 1,3-dipolar compoundOrganic nitrogen compoundOrganic oxideOrganic oxygen compoundOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundPropargyl-type 1,3-dipolar organic compoundPyrimidonean aminepyrimidoneSolidlogp-0.85logs-1.14solubility1.02e+01 g/llogp-0.91pka_strongest_acidic7.07iupac1,3-diazinane-2,4,5,6-tetroneaverage_mass142.0697mono_mass142.001456562smilesO=C1NC(=O)C(=O)C(=O)N1formulaC4H2N2O4inchiInChI=1S/C4H2N2O4/c7-1-2(8)5-4(10)6-3(1)9/h(H2,5,6,8,9,10)inchikeyHIMXGTXNXJYFGB-UHFFFAOYSA-Npolar_surface_area92.34refractivity26.77polarizability10.3rotatable_bond_count0acceptor_count4donor_count2physiological_charge0formal_charge0Specdb::MsIr1832Specdb::MsIr1833Specdb::MsIr1834Specdb::MsMs2137Specdb::MsMs2138Specdb::MsMs2139Specdb::MsMs287671Specdb::MsMs287672Specdb::MsMs287673Specdb::MsMs326566Specdb::MsMs326567Specdb::MsMs326568Specdb::MsMs2364484Specdb::MsMs2364485Specdb::MsMs2364486Specdb::MsMs2597323Specdb::MsMs2597324Specdb::MsMs2597325Specdb::CMs9806Specdb::CMs155441HMDB02818LXN#<Reference:0x0000555676178050>#<Reference:0x0000555676177e48>#<Reference:0x0000555676177c40>#<Reference:0x0000555676177a60>#<Reference:0x0000555676177830>#<Reference:0x0000555676177678>#<Reference:0x00005556761774c0>#<Reference:0x0000555676177308>#<Reference:0x0000555676177150>#<Reference:0x0000555676176ef8>#<Reference:0x0000555676176c50>AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823