Structure via PubChem · Public domain (PubChem)
alloxan
Sign in to saveAlso known as NSC 7169, 5,6-dioxouracil, 5-oxobarbituric acid, 2,4,5,6-pyrimidinetetrone, pyrimidinetetrone, 2,4,5,6(1H,3H)-pyrimidinetetrone, alloxane, 2,4,5,6-tetraoxohexahydropyrimidine
Alloxan, sometimes referred to as alloxan monohydrate, is an organic compound with the formula . It is classified as a derivative of pyrimidine. The anhydrous derivative 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.
Chemical data
- Formula
- C4H2N2O4
- Molecular weight
- 142.07 g/mol
- IUPAC name
- 1,3-diazinane-2,4,5,6-tetrone
- SMILES
- C1(=O)C(=O)NC(=O)NC1=O
- InChIKey
- HIMXGTXNXJYFGB-UHFFFAOYSA-N
- XLogP
- -1
- Polar surface area
- 92.3 Ų
- H-bond donors
- 2
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Research
8,503 papers- Alloxan diabetes.Physiological reviews · 1948
- Alloxan diabetes.Canadian Medical Association journal · 1947
- [Alloxan diabetes].Deutsche medizinische Wochenschrift (1946) · 1946
- Maternal alloxan exposure induces damage in rat offspring lumbar vertebrae and protective role of arachidonic acid.Romanian journal of morphology and embryology = Revue roumaine de morphologie et embryologie · 2022
- [Alloxan anemia].Biulleten' eksperimental'noi biologii i meditsiny · 1956
via PubMed
Wikidata facts
- Mass
- 142.001
Show 3 more facts
- Commons category
- Alloxan
- chemical formula
- C₄H₂N₂O₄
- canonical SMILES
- C1(=O)C(=O)NC(=O)NC1=O
via Wikidata · CC0
~5 min read
Article
11 sectionsContents
- History and literature
- Synthesis
- Reactions
- Hydrolysis
- Reduction
- Biological effects
- Reactive oxygen species generation
- Impact upon beta cells
- See also
- References
- External links
Alloxan, sometimes referred to as alloxan monohydrate, is an organic compound with the formula . It is classified as a derivative of pyrimidine. The anhydrous derivative 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.
==History and literature== 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 Luigi Valentino Brugnatelli (1761-1818) and was named in 1838 by Wöhler and Liebig. The name "Alloxan" emerged from an amalgamation of the words "Allantoïn" 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.