1.0 2011-09-21 00:24:12 UTC 2015-10-09 22:32:13 UTC FDB023068 Alloxan Alloxan 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-Pyrimidinetetrone 2,4,5,6-Pyrimidintetron 2,4,5,6-Pyrimidintetrone 2,4,5,6-Tetraoxohexahydropyrimidine 2,4,5,6(1H,3H)-Pyrimidinetetrone 5-oxo-barbiturate 5-oxo-barbituric acid 5-Oxobarbitate 5-Oxobarbitic acid 5-Oxobarbituric acid 5,6-Dioxouracil alloxan Alloxan 7169 Alloxan tetrahydrat Alloxane mesoxalyl-Urea Mesoxalylcarbamide Mesoxalylurea NSC 7169 Pyrimidinetetrone C4H2N2O4 142.0697 142.001456562 1,3-diazinane-2,4,5,6-tetrone alloxan 50-71-5 O=C1NC(=O)C(=O)C(=O)N1 InChI=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. Pyrimidones Organic compounds Organoheterocyclic compounds Diazines Pyrimidines and pyrimidine derivatives Aliphatic heteromonocyclic compounds Azacyclic compounds Cyclic ketones Hydrocarbon derivatives Hydropyrimidines Organic carbonic acids and derivatives Organic oxides Organonitrogen compounds Organopnictogen compounds Propargyl-type 1,3-dipolar organic compounds 2,5-dihydropyrimidine Aliphatic heteromonocyclic compound Azacycle Carbonic acid derivative Carbonyl group Cyclic ketone Hydrocarbon derivative Hydropyrimidine Ketone Organic 1,3-dipolar compound Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Propargyl-type 1,3-dipolar organic compound Pyrimidone an amine pyrimidone Solid logp -0.85 ALOGPS logs -1.14 ALOGPS solubility 1.02e+01 g/l ALOGPS logp -0.91 ChemAxon pka_strongest_acidic 7.07 ChemAxon iupac 1,3-diazinane-2,4,5,6-tetrone ChemAxon average_mass 142.0697 ChemAxon mono_mass 142.001456562 ChemAxon smiles O=C1NC(=O)C(=O)C(=O)N1 ChemAxon formula C4H2N2O4 ChemAxon inchi InChI=1S/C4H2N2O4/c7-1-2(8)5-4(10)6-3(1)9/h(H2,5,6,8,9,10) ChemAxon inchikey HIMXGTXNXJYFGB-UHFFFAOYSA-N ChemAxon polar_surface_area 92.34 ChemAxon refractivity 26.77 ChemAxon polarizability 10.3 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsIr 1832 Specdb::MsIr 1833 Specdb::MsIr 1834 Specdb::CMs 9806 Specdb::CMs 155441 Specdb::MsMs 2137 Specdb::MsMs 2138 Specdb::MsMs 2139 Specdb::MsMs 287671 Specdb::MsMs 287672 Specdb::MsMs 287673 Specdb::MsMs 326566 Specdb::MsMs 326567 Specdb::MsMs 326568 Specdb::MsMs 2364484 Specdb::MsMs 2364485 Specdb::MsMs 2364486 Specdb::MsMs 2597323 Specdb::MsMs 2597324 Specdb::MsMs 2597325 HMDB02818 LXN #<Reference:0x000055ce3188c9d0> #<Reference:0x000055ce3188c818> #<Reference:0x000055ce3188c660> #<Reference:0x000055ce3188c4a8> #<Reference:0x000055ce3188c2f0> #<Reference:0x000055ce3188c138> #<Reference:0x000055ce3188bf30> #<Reference:0x000055ce3188bd78> #<Reference:0x000055ce3188bbc0> #<Reference:0x000055ce3188ba08> #<Reference:0x000055ce3188b850> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823