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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:44:45 UTC
Update Date2019-07-23 06:09:14 UTC
HMDB IDHMDB0031670
Secondary Accession Numbers
  • HMDB31670
Metabolite Identification
Common Name1-(Hydroxymethyl)-5,5-dimethyl-2,4-imidazolidinedione
Description1-(Hydroxymethyl)-5,5-dimethyl-2,4-imidazolidinedione, also known as 1-hydroxymethyl-5,5-dimethylhydantoin or monomethylol dimethyl hydantoin, belongs to the class of organic compounds known as hydantoins. These are heterocyclic compounds containing an imidazolidine substituted by ketone group at positions 2 and 4. 1-(Hydroxymethyl)-5,5-dimethyl-2,4-imidazolidinedione is an extremely weak basic (essentially neutral) compound (based on its pKa). FDA approved for use as an adjuvant in the bleaching of food-contact recycled paper and board used in food packaging.
Structure
Data?1563862154
Synonyms
ValueSource
(5,5-Dimethyl-2,4-dioxoimidazolidin-1-yl)methanolChEBI
(Hydroxymethyl)-5,5-dimethyl-2,4-imidazolidinedioneChEBI
1-Hydroxymethyl-5,5-dimethyl-2,4-imidazolidinedioneChEBI
1-Hydroxymethyl-5,5-dimethylhydantoinChEBI
1-Methylol-5,5-dimethylhydantoinChEBI
1-Monomethylol-5,5-dimethylhydantoinChEBI
5,5-Dimethyl-1-(hydroxymethyl)hydantoinChEBI
5,5-Dimethyl-1-(hydroxymethyl)imidazolidine-2,4-dioneChEBI
5,5-Dimethyl-1-hydroxymethylhydantoinChEBI
Hydroxymethyl-5,5-dimethylhydantoinChEBI
MDM HydantoinChEBI
MDMHChEBI
Methylol dimethylhydantoinChEBI
Monomethylol dimethyl hydantoinChEBI
1-(Hydroxymethyl)-5,5-dimethyl hydantoinHMDB
1-(Hydroxymethyl)-5,5-dimethyl-hydantoinHMDB
1-(Hydroxymethyl)-5,5-dimethylhydantoinHMDB
1-(Hydroxymethyl)-5,5-dimethylhydantoin, 8ciHMDB
GlycoserveHMDB
Hydantoin, 1-(hydroxymethyl)-5,5-dimethyl- (8ci)HMDB
mono-MethyloldimethylhydantoinHMDB
MonomethyloldimethylhydantoinHMDB
MethyloldimethylhydantoinMeSH
CPD With unspecified hydroxymethyl locants OF 1-monomethylol-5,5-dimethylhydantoinMeSH
Chemical FormulaC6H10N2O3
Average Molecular Weight158.1552
Monoisotopic Molecular Weight158.069142196
IUPAC Name1-(hydroxymethyl)-5,5-dimethylimidazolidine-2,4-dione
Traditional Name1-(hydroxymethyl)-5,5-dimethylimidazolidine-2,4-dione
CAS Registry Number116-25-6
SMILES
CC1(C)N(CO)C(=O)NC1=O
InChI Identifier
InChI=1S/C6H10N2O3/c1-6(2)4(10)7-5(11)8(6)3-9/h9H,3H2,1-2H3,(H,7,10,11)
InChI KeySIQZJFKTROUNPI-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydantoins. These are heterocyclic compounds containing an imidazolidine substituted by ketone group at positions 2 and 4.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzolidines
Sub ClassImidazolidines
Direct ParentHydantoins
Alternative Parents
Substituents
  • Hydantoin
  • Alpha-amino acid or derivatives
  • N-acyl urea
  • Ureide
  • Dicarboximide
  • Carbonic acid derivative
  • Urea
  • Alkanolamine
  • Carboxylic acid derivative
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point110 - 117 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0 solubleNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility125 g/LALOGPS
logP-0.53ALOGPS
logP-0.81ChemAxon
logS-0.1ALOGPS
pKa (Strongest Acidic)10.11ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area69.64 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity36.25 m³·mol⁻¹ChemAxon
Polarizability14.84 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9400000000-e297abe1b764d5297bf9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fkl-9520000000-53c477462d8b81b9e117Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1900000000-01b54d12be7c0eaa4629Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052k-9000000000-52ce6e5d976601ede175Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-6eeffadb59e74fd3feb2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-06vi-0900000000-696c8b390e874a7cae2fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-8900000000-bbb6605e3436ccfdc9beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-5f717def0cd2eaa75ebeSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008330
KNApSAcK IDNot Available
Chemspider ID60357
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound67000
PDB IDNot Available
ChEBI ID143246
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .