Allantoin

Allantoin is a chemical compound with formula C4H6N4O3. It is also called 5-ureidohydantoin or glyoxyldiureide. It is a diureide of glyoxylic acid. Allantoin is a major metabolic intermediate in most organisms including animals, plants and bacteria. It is produced from uric acid, which itself is a degradation product of nucleic acids, by action of urate oxidase (uricase). Allantoin also occurs as a natural mineral compound (IMA symbol Aan).

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Allantoin
Names
IUPAC name
N-(2,5-Dioxoimidazolidin-4-yl)urea
Other names
1-(2,5-Dioxoimidazolidin-4-yl)urea
Glyoxyldiureide
5-Ureidohydantoin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.358
EC Number
  • 202-592-8
KEGG
PubChem CID
RTECS number
  • YT1600000
UNII
  • InChI=1S/C4H6N4O3/c5-3(10)6-1-2(9)8-4(11)7-1/h1H,(H3,5,6,10)(H2,7,8,9,11) Y
    Key: POJWUDADGALRAB-UHFFFAOYSA-N Y
  • InChI=1/C4H6N4O3/c5-3(10)6-1-2(9)8-4(11)7-1/h1H,(H3,5,6,10)(H2,7,8,9,11)
    Key: POJWUDADGALRAB-UHFFFAOYAE
SMILES
  • O=C1NC(=O)NC1NC(=O)N
  • C1(C(=O)NC(=O)N1)NC(=O)N
Properties
C4H6N4O3
Molar mass 158.117 g·mol−1
Appearance colourless crystalline powder
Odor odorless
Density 1.45 g/cm3
Melting point 230 °C (446 °F; 503 K) (decomposes)
Boiling point 478 °C (892 °F; 751 K)
0.57 g/100 mL (25 °C)
4.0 g/100 mL (75 °C)
Solubility soluble in alcohol, pyridine, NaOH
insoluble in ethyl ether
log P −3.14
Acidity (pKa) 8.48
Hazards
NFPA 704 (fire diamond)
2
1
0
Lethal dose or concentration (LD, LC):
LD50 (median dose)
 > 5000 mg/kg (oral, rat)
Safety data sheet (SDS) Allantoin 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 YN ?)
Infobox references
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