Structure via PubChem · Public domain (PubChem)
hydantoin
Sign in to saveAlso known as imidazole-2,4(3H,5H)-dione, 2,4(3H,5H)-imidazoledione, 2,4-imidazolidinedione
Hydantoin, or glycolylurea, is a heterocyclic organic compound with the formula CH2C(O)NHC(O)NH. It is a colorless solid that arises from the reaction of glycolic acid and urea. It is an oxidized derivative of imidazolidine. In a more general sense, hydantoins can refer to groups or a class of compounds with the same ring structure as the parent compound. For example, phenytoin (mentioned below) has two phenyl groups substituted onto the number 5 carbon in a hydantoin molecule.
Chemical data
- Formula
- C3H4N2O2
- Molecular weight
- 100.08 g/mol
- IUPAC name
- imidazolidine-2,4-dione
- SMILES
- C1C(=O)NC(=O)N1
- InChIKey
- WJRBRSLFGCUECM-UHFFFAOYSA-N
- XLogP
- -1.7
- Polar surface area
- 58.2 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 100.027
Show 4 more facts
- canonical SMILES
- C1C(=O)NC(=O)N1
- chemical formula
- C₃H₄N₂O₂
- Commons category
- Hydantoin
- melting point
- 222
Sources (2)
via Wikidata · CC0
~4 min read
Article
10 sectionsContents
- Synthesis
- Uses and occurrence
- Pharmaceuticals
- Pesticides
- Synthesis of amino acids
- Methylation
- Halogenation
- DNA oxidation to hydantoins after cell death
- External links and further reading
- References
Hydantoin, or glycolylurea, is a heterocyclic organic compound with the formula CH2C(O)NHC(O)NH. It is a colorless solid that arises from the reaction of glycolic acid and urea. It is an oxidized derivative of imidazolidine. In a more general sense, hydantoins can refer to groups or a class of compounds with the same ring structure as the parent compound. For example, phenytoin (mentioned below) has two phenyl groups substituted onto the number 5 carbon in a hydantoin molecule.
==Synthesis== Hydantoin was first isolated in 1861 by Adolf von Baeyer in the course of his study of uric acid. He obtained it by hydrogenation of allantoin, hence the name. left|700px