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Alloxan information


Alloxan[1]
Alloxan
Alloxan hydrate
Names
Preferred IUPAC name
5,5-Dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione
Other names
5,5-Dihydroxybarbituric acid
Identifiers
CAS Number
  • 50-71-5 (Anhydrous) checkY
  • 3237-50-1 (monohydrate) checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:76451 checkY
ChEMBL
  • ChEMBL1096009 checkY
ChemSpider
  • 5577 checkY
ECHA InfoCard 100.000.057 Edit this at Wikidata
EC Number
  • 200-062-0
MeSH Alloxan
PubChem CID
  • 5781
UNII
  • 6SW5YHA5NG (anhydrous) checkY
  • O2AAP9F8B6 (monohydrate) checkY
CompTox Dashboard (EPA)
  • DTXSID5044946 Edit this at Wikidata
InChI
  • InChI=1S/C4H2N2O4/c7-1-2(8)5-4(10)6-3(1)9/h(H2,5,6,8,9,10) checkY
    Key: HIMXGTXNXJYFGB-UHFFFAOYSA-N checkY
  • InChI=1/C4H2N2O4/c7-1-2(8)5-4(10)6-3(1)9/h(H2,5,6,8,9,10)
    Key: HIMXGTXNXJYFGB-UHFFFAOYAQ
SMILES
  • C1(=O)C(=O)NC(=O)NC1=O
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[2]
Hazards
Safety data sheet (SDS) MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Alloxan, sometimes referred to as alloxan hydrate, is an 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 exhibit a variety of biological activities.

  1. ^ Merck Index, 11th Edition, 281.
  2. ^ Cite error: The named reference OS was invoked but never defined (see the help page).

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Alloxan

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Alloxan, sometimes referred to as alloxan hydrate, is an organic compound with the formula OC(N(H)CO)2C(OH)2. It is classified as a derivative of pyrimidine...

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Strecker degradation

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German chemist. The original observation by Strecker involved the use of alloxan as the oxidant in the first step, followed by hydrolysis: The reaction...

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Pyrimidine

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the nucleotides cytosine, thymine and uracil, thiamine (vitamin B1) and alloxan. It is also found in many synthetic compounds such as barbiturates and...

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Stevia rebaudiana

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medium-polar extract from the leaves of Stevia rebaudiana Bert. (Bertoni) on alloxan-induced diabetic rats". J Pharm Bioallied Sci. 3 (2): 242–8. doi:10.4103/0975-7406...

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Artemisia pallens

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observed to reduce blood glucose levels in glucose−fed hyperglycemic and alloxan-treated rabbits and rats. Davana oil is used in making perfumes of sweet...

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Streptozotocin

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N-N bond in the N-nitrosourea pharmacophore by oxidative rearrangement. Alloxan Brentjens R, Saltz L (June 2001). "Islet cell tumors of the pancreas: the...

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Phosphatidylserine

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macrophage phagocytosis and lymphocyte response to concanavalin A: a study in alloxan-induced diabetic rats". Cell Biochemistry and Function. 26 (8): 859–865...

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Barbituric acid

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chemist Adolf von Baeyer, by reducing what Baeyer called Alloxanbromid (alloxan dibromide, now: 5,5-dibromobarbituric acid) with hydrocyanic acid, and...

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Heterocyclic compound

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organic chemistry. Some noteworthy developments: 1818: Brugnatelli makes alloxan from uric acid 1832: Dobereiner produces furfural (a furan) by treating...

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Gymnema sylvestre

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antidiabetic and hypolipidemic effect of Gymnema sylvestre in non-diabetic and alloxan-diabetic rats". Braz. Arch. Biol. Technol. 47 (4): 545–551. doi:10...

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Stevia

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medium-polar extract from the leaves of Stevia rebaudiana Bert. (Bertoni) on alloxan-induced diabetic rats". J Pharm Bioallied Sci. 3 (2): 242–248. doi:10.4103/0975-7406...

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Pleurotus pulmonarius

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effect, halted the progression of diabetes, and reduced the mortality of alloxan induced diabetic mice by approximately 50%. It showed a synergistic effect...

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Euphorbia prostrata

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EUPHORBIA PROSTRATA along with FUMARIA PARVIFLORA in noemoglycaemic and alloxan treated hyper glycaemic rabbits as quoted in the book MAJOR HERBS OF AURVEDA:...

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Diospyros melanoxylon

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Antihyperglycemic effect of Diospyros melanoxylon (Roxb.) bark against Alloxan-induced diabetic rats Jadhav J. K*.Masirkar V. J., Deshmukh V. N.International...

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Riboflavin

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aniline, produced by reductive amination using D-ribose, was condensed with alloxan in the final step: Keratoconus is the most common form of corneal ectasia...

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Murexide

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(5-aminobarbituric acid) with mercury oxide. It may also be prepared by digesting alloxan with alcoholic ammonia. Justus von Liebig and Friedrich Wöhler in Giessen...

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Maud Menten

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"Changes in alkaline phosphatase of kidney following renal damage with alloxan". Proceedings of the Society for Experimental Biology and Medicine. 63...

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Purpuric acid

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Purpuric acid is a nitrogenous acid related to barbituric acid that yields alloxan and uramil upon hydrolysis. It is noteworthy for its purple-red salts,...

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Diethyl oxomalonate

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in pure form, starting from decomposition of the barium salt of alloxan to oxomalonic acid followed by esterification with ethanol in the presence...

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Type 1 diabetes

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Stojanović M, Prostran M (March 2016). "Experimental diabetes induced by alloxan and streptozotocin: The current state of the art". Journal of Pharmacological...

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Toona sinensis

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Hyperglycemia and Protects Hepatocytes in High-Carbohydrate/High-Fat Diet and Alloxan Induced Experimental Diabetic Mice". Journal of Diabetes Research. 2016:...

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Violuric acid

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barbituric acid with nitrous acid. It can also be produced by condensation of alloxan with hydroxylamine. as typical for forming the oxime of other carbonyl...

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Beta cell

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experimentally induced in vivo for research purposes by streptozotocin or alloxan, which are specifically toxic to beta cells. Mouse and rat models of diabetes...

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Mesoxalic acid

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dihydroxymalonate. Mesoxalic acid can be obtained synthetically by hydrolysis of alloxan with baryta water, by warming caffuric acid with lead acetate solution...

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Momordica cymbalaria

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and hypolipidemic effects of Momordica cymbalaria Hook. Fruit powder in alloxan-diabetic rats". Journal of Ethnopharmacology. 67 (1): 103–109. doi:10...

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GLUT4

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(September 1959). "Regulation of glucose uptake in heart muscle from normal and alloxan-diabetic rats: the effects of insulin, growth hormone, cortisone, and anoxia"...

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