Record Information
Version1.0
Creation date2015-10-09 22:27:43 UTC
Update date2017-01-19 02:36:11 UTC
FoodComEx IDPC000048
FoodDB RecordFDB006426
Chemical Information
NameUracil
DescriptionUracil, also known as U or hybar X, belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. Uracil is an extremely weak basic (essentially neutral) compound (based on its pKa). Uracil exists in all living species, ranging from bacteria to humans. Within humans, uracil participates in a number of enzymatic reactions. In particular, uracil and ribose 1-phosphate can be biosynthesized from uridine; which is catalyzed by the enzyme uridine phosphorylase 2. In addition, uracil can be converted into dihydrouracil through its interaction with the enzyme dihydropyrimidine dehydrogenase [nadp(+)]. In humans, uracil is involved in pyrimidine metabolism. Outside of the human body, Uracil is found, on average, in the highest concentration within beers. Uracil has also been detected, but not quantified in, several different foods, such as radish (var.), green beans, cauliflowers, prickly pears, and citrus. This could make uracil a potential biomarker for the consumption of these foods. Uracil is a potentially toxic compound. Uracil, with regard to humans, has been found to be associated with several diseases such as canavan disease, hypertension, and cerebral infarction; uracil has also been linked to several inborn metabolic disorders including carbamoyl phosphate synthetase deficiency and dihydropyrimidine dehydrogenase deficiency.
CAS Number66-22-8
Structure
Thumb
Synonyms
SynonymSource
1H-Pyrimidine-2,4-dionebiospider
2,4-dihydroxypyrimidinebiospider
2,4-Dioxopyrimidinebiospider
2,4-Pyrimidinediolbiospider
2,4-Pyrimidinedionebiospider
2,4(1H,3H)-Pyrimidinedionebiospider
2,4(1H,3H)-Pyrimidinedione (9CI)biospider
Hybar XHMDB
PirodHMDB
Pyrodbiospider
UChEBI
UraChEBI
Urazilbiospider
Chemical FormulaC4H4N2O2
IUPAC name1,2,3,4-tetrahydropyrimidine-2,4-dione
InChI IdentifierInChI=1S/C4H4N2O2/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8)
InChI KeyISAKRJDGNUQOIC-UHFFFAOYSA-N
Isomeric SMILESO=C1NC=CC(=O)N1
Average Molecular Weight112.0868
Monoisotopic Molecular Weight112.027277382
Chemical Taxonomy
ClassificationNot classified
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logP-1.07HANSCH,C ET AL. (1995)
Experimental Water Solubility3.6 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting Point330 oC
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 6 g
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci A390
AKSci J91282
Glentham GK0306
MetaSci HMDB0000300
Sigma-Aldrich HMDB0000300
Toronto Research Chemicals U801000