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Alloxan

From Wikipedia, the free encyclopedia

Alloxan[1]

IUPAC name[hide]

1,3-Diazinane-2,4,5,6-tetrone

SMILES

[show]

InChI

[show]

Properties

Molecular formula C4H2N2O4

Molar mass 142.07 g/mol

Melting point 256 C (decomposition)

Solubilityinwater Freely soluble

Hazards

MSDS MSDS

(verify)(what is: / ?)

Except where noted otherwise, data are given for materials

in theirstandard state (at 25 C, 100 kPa)

Infobox references

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Alloxan (2,4,5,6-tetraoxypyrimidine; 2,4,5,6-pyrimidinetetrone) is an oxygenatedpyrimidinederivative. It is present as alloxanhydratein aqueous solution.

d/kiko 2011/bioqumica

History

Alloxan was originally isolated in 1818 by Brugnatelli and was named in 1838 by Whler

and Liebig. The name "Alloxan" emerged from an amalgamation of the words "Allantoin"and "Oxalsure" (oxalic acid).

Biological effects

Alloxan is a toxicglucoseanalogue, which selectively destroys insulin-producing cells in

the pancreas (that is beta cells) when administered to rodents and many other animal

species. This causes an insulin-dependent diabetes mellitus (called "Alloxan Diabetes") inthese animals, with characteristics similar to type 1 diabetes in humans. Alloxan is

selectively toxic to insulin-producing pancreatic beta cells because it preferentially

accumulates in beta cells through uptake via the GLUT2 glucose transporter. Alloxan, inthe presence of intracellular thiols, generatesreactive oxygen species(ROS) in a cyclic

reaction with its reduction product, dialuric acid. The beta cell toxic action of alloxan is

initiated by free radicals formed in this redox reaction. One study suggests that alloxan does

not cause diabetes in humans.[2]

Others found a significant difference in alloxan plasma

levels in children with and without diabetes Type 1.

[3]

Discovery

The compound was discovered byJustus von LiebigandFriedrich Whlerfollowing the

discovery ofureain 1828 and is one of the oldest named organic compounds that exist. The

alloxan model of diabetes was first described in rabbits by Dunn, Sheehan and McLetchiein 1943.

[4]

Etymology

The name is derived fromallantoin, a product ofuric acidexcreted by thefetusinto the

allantoisandoxaluric acidderived fromoxalic acidandurea, found inurine.

Synthesis

http://en.wikipedia.org/wiki/Pyrimidinehttp://en.wikipedia.org/wiki/Pyrimidinehttp://en.wikipedia.org/wiki/Hydratehttp://en.wikipedia.org/wiki/Hydratehttp://en.wikipedia.org/wiki/Hydratehttp://en.wikipedia.org/wiki/Allantoinhttp://en.wikipedia.org/wiki/Allantoinhttp://en.wikipedia.org/wiki/Allantoinhttp://en.wikipedia.org/wiki/Oxalic_acidhttp://en.wikipedia.org/wiki/Oxalic_acidhttp://en.wikipedia.org/wiki/Oxalic_acidhttp://en.wikipedia.org/wiki/Glucosehttp://en.wikipedia.org/wiki/Glucosehttp://en.wikipedia.org/wiki/Glucosehttp://en.wikipedia.org/wiki/Reactive_oxygen_specieshttp://en.wikipedia.org/wiki/Reactive_oxygen_specieshttp://en.wikipedia.org/wiki/Reactive_oxygen_specieshttp://en.wikipedia.org/wiki/Alloxan#cite_note-literature1-1http://en.wikipedia.org/wiki/Alloxan#cite_note-literature1-1http://en.wikipedia.org/wiki/Alloxan#cite_note-literature1-1http://en.wikipedia.org/wiki/Alloxan#cite_note-literature2-2http://en.wikipedia.org/wiki/Alloxan#cite_note-literature2-2http://en.wikipedia.org/wiki/Alloxan#cite_note-literature2-2http://en.wikipedia.org/wiki/Justus_von_Liebighttp://en.wikipedia.org/wiki/Justus_von_Liebighttp://en.wikipedia.org/wiki/Justus_von_Liebighttp://en.wikipedia.org/wiki/Friedrich_W%C3%B6hlerhttp://en.wikipedia.org/wiki/Friedrich_W%C3%B6hlerhttp://en.wikipedia.org/wiki/Friedrich_W%C3%B6hlerhttp://en.wikipedia.org/wiki/Ureahttp://en.wikipedia.org/wiki/Ureahttp://en.wikipedia.org/wiki/Ureahttp://en.wikipedia.org/wiki/Alloxan#cite_note-3http://en.wikipedia.org/wiki/Alloxan#cite_note-3http://en.wikipedia.org/wiki/Alloxan#cite_note-3http://en.wikipedia.org/wiki/Allantoinhttp://en.wikipedia.org/wiki/Allantoinhttp://en.wikipedia.org/wiki/Allantoinhttp://en.wikipedia.org/wiki/Uric_acidhttp://en.wikipedia.org/wiki/Uric_acidhttp://en.wikipedia.org/wiki/Uric_acidhttp://en.wikipedia.org/wiki/Fetushttp://en.wikipedia.org/wiki/Fetushttp://en.wikipedia.org/wiki/Fetushttp://en.wikipedia.org/wiki/Allantoishttp://en.wikipedia.org/wiki/Allantoishttp://en.wikipedia.org/w/index.php?title=Oxaluric_acid&action=edit&redlink=1http://en.wikipedia.org/w/index.php?title=Oxaluric_acid&action=edit&redlink=1http://en.wikipedia.org/w/index.php?title=Oxaluric_acid&action=edit&redlink=1http://en.wikipedia.org/wiki/Oxalic_acidhttp://en.wikipedia.org/wiki/Oxalic_acidhttp://en.wikipedia.org/wiki/Oxalic_acidhttp://en.wikipedia.org/wiki/Ureahttp://en.wikipedia.org/wiki/Ureahttp://en.wikipedia.org/wiki/Ureahttp://en.wikipedia.org/wiki/Urinehttp://en.wikipedia.org/wiki/Urinehttp://en.wikipedia.org/wiki/Urinehttp://en.wikipedia.org/wiki/Urinehttp://en.wikipedia.org/wiki/Ureahttp://en.wikipedia.org/wiki/Oxalic_acidhttp://en.wikipedia.org/w/index.php?title=Oxaluric_acid&action=edit&redlink=1http://en.wikipedia.org/wiki/Allantoishttp://en.wikipedia.org/wiki/Fetushttp://en.wikipedia.org/wiki/Uric_acidhttp://en.wikipedia.org/wiki/Allantoinhttp://en.wikipedia.org/wiki/Alloxan#cite_note-3http://en.wikipedia.org/wiki/Ureahttp://en.wikipedia.org/wiki/Friedrich_W%C3%B6hlerhttp://en.wikipedia.org/wiki/Justus_von_Liebighttp://en.wikipedia.org/wiki/Alloxan#cite_note-literature2-2http://en.wikipedia.org/wiki/Alloxan#cite_note-literature1-1http://en.wikipedia.org/wiki/Reactive_oxygen_specieshttp://en.wikipedia.org/wiki/Glucosehttp://en.wikipedia.org/wiki/Oxalic_acidhttp://en.wikipedia.org/wiki/Allantoinhttp://en.wikipedia.org/wiki/Hydratehttp://en.wikipedia.org/wiki/Pyrimidine

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The original preparation for alloxan was by oxidation ofuric acidbynitric acid. In another

method the monohydrate is prepared by oxidation ofbarbituric acidbychromium trioxide[5]

Alloxan is a strongoxidizing agentand it forms ahemiacetalwith its reduced reactionproduct dialuric acid (in which acarbonylgroup is reduced to ahydroxylgroup) which iscalled alloxantin.

[6]

Alloxane (left) with dialuric acid (right) and alloxantin (center)

Commercial use

Alloxane is a raw material for the production of the purple dyemurexide.Carl Wilhelm

Scheelediscovered the dye in 1776. Murexide is the product of the complex in-situmultistep reaction of alloxantin and gaseousammonia. Murexide results from the

condensation of the unisolated intermediate uramil with alloxan, liberated during the

course of the reaction.

Murexide dye (right) from reaction of alloxantin (left)

Scheele sourceduric acidfrom humancalculi(such askidney stones) and called

the compoundlithicacid.William Proutinvestigated the compound in 1818 and heusedboa constrictorexcrement with up to 90% ammonium acid urate.

Liebig and Whler in the nineteenth century coined the name murexide for the dyeafter theTrunculus Murexwhich is the source of the Tyrian purple of antiquity.

Primo Leviin his novel The Periodic Table in chapterNitrogen considerspythons

as a source for alloxane on behalf of alipstickproducer but he is turned down by

the director of theTurinzoo because the zoo already has lucrative contracts withcosmetics companies.

http://en.wikipedia.org/wiki/Uric_acidhttp://en.wikipedia.org/wiki/Uric_acidhttp://en.wikipedia.org/wiki/Uric_acidhttp://en.wikipedia.org/wiki/Nitric_acidhttp://en.wikipedia.org/wiki/Nitric_acidhttp://en.wikipedia.org/wiki/Nitric_acidhttp://en.wikipedia.org/wiki/Barbituric_acidhttp://en.wikipedia.org/wiki/Barbituric_acidhttp://en.wikipedia.org/wiki/Barbituric_acidhttp://en.wikipedia.org/wiki/Chromium_trioxidehttp://en.wikipedia.org/wiki/Chromium_trioxidehttp://en.wikipedia.org/wiki/Chromium_trioxidehttp://en.wikipedia.org/wiki/Alloxan#cite_note-4http://en.wikipedia.org/wiki/Alloxan#cite_note-4http://en.wikipedia.org/wiki/Oxidizing_agenthttp://en.wikipedia.org/wiki/Oxidizing_agenthttp://en.wikipedia.org/wiki/Oxidizing_agenthttp://en.wikipedia.org/wiki/Hemiacetalhttp://en.wikipedia.org/wiki/Hemiacetalhttp://en.wikipedia.org/wiki/Hemiacetalhttp://en.wikipedia.org/wiki/Carbonylhttp://en.wikipedia.org/wiki/Carbonylhttp://en.wikipedia.org/wiki/Carbonylhttp://en.wikipedia.org/wiki/Hydroxylhttp://en.wikipedia.org/wiki/Hydroxylhttp://en.wikipedia.org/wiki/Hydroxylhttp://en.wikipedia.org/wiki/Alloxan#cite_note-5http://en.wikipedia.org/wiki/Alloxan#cite_note-5http://en.wikipedia.org/wiki/Alloxan#cite_note-5http://en.wikipedia.org/wiki/Murexidehttp://en.wikipedia.org/wiki/Murexidehttp://en.wikipedia.org/wiki/Murexidehttp://en.wikipedia.org/wiki/Carl_Wilhelm_Scheelehttp://en.wikipedia.org/wiki/Carl_Wilhelm_Scheelehttp://en.wikipedia.org/wiki/Carl_Wilhelm_Scheelehttp://en.wikipedia.org/wiki/Carl_Wilhelm_Scheelehttp://en.wikipedia.org/wiki/Ammoniahttp://en.wikipedia.org/wiki/Ammoniahttp://en.wikipedia.org/wiki/Ammoniahttp://en.wikipedia.org/wiki/Uric_acidhttp://en.wikipedia.org/wiki/Uric_acidhttp://en.wikipedia.org/wiki/Uric_acidhttp://en.wikipedia.org/wiki/Calculihttp://en.wikipedia.org/wiki/Calculihttp://en.wikipedia.org/wiki/Calculihttp://en.wikipedia.org/wiki/Kidney_stonehttp://en.wikipedia.org/wiki/Kidney_stonehttp://en.wikipedia.org/wiki/Kidney_stonehttp://en.wikipedia.org/wiki/Lithichttp://en.wikipedia.org/wiki/Lithichttp://en.wikipedia.org/wiki/Lithichttp://en.wikipedia.org/wiki/William_Prouthttp://en.wikipedia.org/wiki/William_Prouthttp://en.wikipedia.org/wiki/William_Prouthttp://en.wikipedia.org/wiki/Boa_(genus)http://en.wikipedia.org/wiki/Boa_(genus)http://en.wikipedia.org/wiki/Boa_(genus)http://en.wikipedia.org/wiki/Trunculus_Murexhttp://en.wikipedia.org/wiki/Trunculus_Murexhttp://en.wikipedia.org/wiki/Trunculus_Murexhttp://en.wikipedia.org/wiki/Primo_Levihttp://en.wikipedia.org/wiki/Primo_Levihttp://en.wikipedia.org/wiki/Pythonidaehttp://en.wikipedia.org/wiki/Pythonidaehttp://en.wikipedia.org/wiki/Pythonidaehttp://en.wikipedia.org/wiki/Lipstickhttp://en.wikipedia.org/wiki/Lipstickhttp://en.wikipedia.org/wiki/Lipstickhttp://en.wikipedia.org/wiki/Turinhttp://en.wikipedia.org/wiki/Turinhttp://en.wikipedia.org/wiki/Turinhttp://en.wikipedia.org/wiki/File:Murexide_dye.pnghttp://en.wikipedia.org/wiki/File:Murexide_dye.pnghttp://en.wikipedia.org/wiki/File:Alloxane_chemistry.pnghttp://en.wikipedia.org/wiki/File:Alloxane_chemistry.pnghttp://en.wikipedia.org/wiki/File:Murexide_dye.pnghttp://en.wikipedia.org/wiki/File:Murexide_dye.pnghttp://en.wikipedia.org/wiki/File:Alloxane_chemistry.pnghttp://en.wikipedia.org/wiki/File:Alloxane_chemistry.pnghttp://en.wikipedia.org/wiki/File:Murexide_dye.pnghttp://en.wikipedia.org/wiki/File:Murexide_dye.pnghttp://en.wikipedia.org/wiki/File:Alloxane_chemistry.pnghttp://en.wikipedia.org/wiki/File:Alloxane_chemistry.pnghttp://en.wikipedia.org/wiki/File:Murexide_dye.pnghttp://en.wikipedia.org/wiki/File:Murexide_dye.pnghttp://en.wikipedia.org/wiki/File:Alloxane_chemistry.pnghttp://en.wikipedia.org/wiki/File:Alloxane_chemistry.pnghttp://en.wikipedia.org/wiki/Turinhttp://en.wikipedia.org/wiki/Lipstickhttp://en.wikipedia.org/wiki/Pythonidaehttp://en.wikipedia.org/wiki/Primo_Levihttp://en.wikipedia.org/wiki/Trunculus_Murexhttp://en.wikipedia.org/wiki/Boa_(genus)http://en.wikipedia.org/wiki/William_Prouthttp://en.wikipedia.org/wiki/Lithichttp://en.wikipedia.org/wiki/Kidney_stonehttp://en.wikipedia.org/wiki/Calculihttp://en.wikipedia.org/wiki/Uric_acidhttp://en.wikipedia.org/wiki/Ammoniahttp://en.wikipedia.org/wiki/Carl_Wilhelm_Scheelehttp://en.wikipedia.org/wiki/Carl_Wilhelm_Scheelehttp://en.wikipedia.org/wiki/Murexidehttp://en.wikipedia.org/wiki/Alloxan#cite_note-5http://en.wikipedia.org/wiki/Hydroxylhttp://en.wikipedia.org/wiki/Carbonylhttp://en.wikipedia.org/wiki/Hemiacetalhttp://en.wikipedia.org/wiki/Oxidizing_agenthttp://en.wikipedia.org/wiki/Alloxan#cite_note-4http://en.wikipedia.org/wiki/Chromium_trioxidehttp://en.wikipedia.org/wiki/Barbituric_acidhttp://en.wikipedia.org/wiki/Nitric_acidhttp://en.wikipedia.org/wiki/Uric_acid

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Impact upon beta cells

Because it selectively kills theinsulin-producingbeta-cellsfound in the pancreas,

alloxan is used to inducediabetesin laboratory animals. This occurs most likelybecause of selective uptake of the compound due to its structural similarity to

glucoseas well as the beta-cell's highly efficient uptake mechanism (GLUT2).

However, alloxan is not toxic to the human beta-cell, even in very high doses,

probably due to differing glucose uptake mechanisms in humans and

rodents.[7][8]

Alloxan is, however, toxic to theliverand thekidneysin highdoses.

[citation needed]

http://en.wikipedia.org/wiki/Insulinhttp://en.wikipedia.org/wiki/Insulinhttp://en.wikipedia.org/wiki/Insulinhttp://en.wikipedia.org/wiki/Beta-cellshttp://en.wikipedia.org/wiki/Beta-cellshttp://en.wikipedia.org/wiki/Beta-cellshttp://en.wikipedia.org/wiki/Diabeteshttp://en.wikipedia.org/wiki/Diabeteshttp://en.wikipedia.org/wiki/Diabeteshttp://en.wikipedia.org/wiki/Glucosehttp://en.wikipedia.org/wiki/Glucosehttp://en.wikipedia.org/wiki/GLUT2http://en.wikipedia.org/wiki/GLUT2http://en.wikipedia.org/wiki/GLUT2http://en.wikipedia.org/wiki/Alloxan#cite_note-6http://en.wikipedia.org/wiki/Alloxan#cite_note-6http://en.wikipedia.org/wiki/Liverhttp://en.wikipedia.org/wiki/Liverhttp://en.wikipedia.org/wiki/Liverhttp://en.wikipedia.org/wiki/Kidneyshttp://en.wikipedia.org/wiki/Kidneyshttp://en.wikipedia.org/wiki/Kidneyshttp://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/wiki/Kidneyshttp://en.wikipedia.org/wiki/Liverhttp://en.wikipedia.org/wiki/Alloxan#cite_note-6http://en.wikipedia.org/wiki/Alloxan#cite_note-6http://en.wikipedia.org/wiki/GLUT2http://en.wikipedia.org/wiki/Glucosehttp://en.wikipedia.org/wiki/Diabeteshttp://en.wikipedia.org/wiki/Beta-cellshttp://en.wikipedia.org/wiki/Insulin