1,3-Dimethylol-5,5-dimethylhydantoin (CHEM002600)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (2)XML
Record Information
Version1.0
Creation Date2009-11-24 00:49:49 UTC
Update Date2026-04-17 18:09:53 UTC
Accession NumberCHEM002600
Identification
Common Name1,3-Dimethylol-5,5-dimethylhydantoin
ClassSmall Molecule
Description1,3-Dimethylol-5,5-dimethylhydantoin (DMDM hydantoin) is an antimicrobial formaldehyde releaser preservative with the trade name Glydant. DMDM hydantoin is an organic compound belonging a class of compounds known as hydantoins. It is used in the cosmetics industry and found in products like shampoos, hair conditioners and skin care products. (5)
Contaminant Sources
  • Cosmetic Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 1
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Amine
  • Cosmetic Toxin
  • Household Toxin
  • Industrial/Workplace Toxin
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DMDM HydantoinMeSH
Chemical FormulaC7H12N2O4
Average Molecular Mass188.181 g/mol
Monoisotopic Mass188.080 g/mol
CAS Registry Number6440-58-0
IUPAC Name1,3-bis(hydroxymethyl)-5,5-dimethylimidazolidine-2,4-dione
Traditional Namedmdm hydantoin
SMILESCC1(C)N(CO)C(=O)N(CO)C1=O
InChI IdentifierInChI=1S/C7H12N2O4/c1-7(2)5(12)8(3-10)6(13)9(7)4-11/h10-11H,3-4H2,1-2H3
InChI KeyWSDISUOETYTPRL-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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
Solubility261 mg/mL at 25°C
Predicted Properties
PropertyValueSource
Water Solubility307 g/LALOGPS
logP-0.9ALOGPS
logP-1.2ChemAxon
logS0.21ALOGPS
pKa (Strongest Acidic)13.63ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area81.08 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity42.25 m³·mol⁻¹ChemAxon
Polarizability17.87 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-f653d98c20ace646b859Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052s-9100000000-3d0d2971c6802fe234e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05br-9500000000-d388b5e67eb43c5eb4eaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-9ff7829acc5f67bc0fe0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-4900000000-6453041479be11c73916Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001l-9100000000-a62cc2ce9d88a336fa35Spectrum
Toxicity Profile
Route of ExposureOral (4) ; inhalation (4) ; dermal (4)
Mechanism of ToxicityDMDM hydantoin is a formaldehyde releaser. It is likely that formaldehyde toxicity occurs when intracellular levels saturate formaldehyde dehydrogenase activity, allowing the unmetabolized intact molecule to exert its effects. Formaldehyde is known to form cross links between protein and DNA and undergo metabolic incorporation into macromolecules (DNA, RNA, and proteins). (4, 5)
MetabolismFormaldehyde may be absorbed following inhalation, oral, or dermal exposure. It is an essential metabolic intermediate in all cells and is produced during the normal metabolism of serine, glycine, methionine, and choline and also by the demethylation of N-, S-, and O-methyl compounds. Exogenous formaldehyde is metabolized to formate by the enzyme formaldehyde dehydrogenase at the initial site of contact. After oxidation of formaldehyde to formate, the carbon atom is further oxidized to carbon dioxide or incorporated into purines, thymidine, and amino acids via tetrahydrofolatedependent one-carbon biosynthetic pathways. Formaldehyde is not stored in the body and is excreted in the urine (primarily as formic acid), incorporated into other cellular molecules, or exhaled as carbon dioxide. (4)
Toxicity ValuesLD50: 2.0-3.65 g/kg (Oral, Rat) (1)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)1, carcinogenic to humans (for formaldehyde). (3)
Uses/Sources1,3-Dimethylol-5,5-dimethylhydantoin (DMDM hydantoin) is an antimicrobial formaldehyde releaser preservative with the trade name Glydant. It is used in the cosmetics industry and found in products like shampoos, hair conditioners and skin care products. (5)
Minimum Risk LevelNot Available
Health EffectsDMDM hydantoin releases formaldehyde, a known human carcinogen. (4, 5)
SymptomsDMDM hydantoin may cause contact dermatitis. (2)
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available