Tmic
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Record Information
Version2.0
Creation Date2009-11-24 00:49:49 UTC
Update Date2014-12-24 20:26:14 UTC
Accession NumberT3D3627
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. (6)
Compound Type
  • Amide
  • Amine
  • Cosmetic Toxin
  • Household Toxin
  • Industrial/Workplace Toxin
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
1,3-Bis(hydroxymethyl)-5,5-dimethyl-2,4-imidazolidinedione
1,3-Bis(hydroxymethyl)-5,5-dimethylhydantoin
1,3-Bis(hydroxymethyl)-5,5-dimethylimidazolidine-2,4-dione
1,3-Di(hydroxymethyl)-5,5-dimethylhydantoin
1,3-dimethylol-5,5-dimethyl-hydantoin
Dantoin dmdmh 55
Dantoin-DMDMH
Dimethylol-5,5-dimethylhydantoin
DMDM hydantoin
Dmdmh
Dmdmh 55
Glycoserve-DMDMH
Glydant
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 KeyInChIKey=WSDISUOETYTPRL-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
LogPNot Available
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-f653d98c20ace646b859View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052s-9100000000-3d0d2971c6802fe234e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05br-9500000000-d388b5e67eb43c5eb4eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-9ff7829acc5f67bc0fe0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-4900000000-6453041479be11c73916View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001l-9100000000-a62cc2ce9d88a336fa35View in MoNA
Toxicity Profile
Route of ExposureOral (5) ; inhalation (5) ; dermal (5)
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). (5, 6)
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. (5)
Toxicity ValuesLD50: 2.0-3.65 g/kg (Oral, Rat) (2)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)1, carcinogenic to humans (for formaldehyde). (4)
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. (6)
Minimum Risk LevelNot Available
Health EffectsDMDM hydantoin releases formaldehyde, a known human carcinogen. (5, 6)
SymptomsDMDM hydantoin may cause contact dermatitis. (1)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID22947
ChEMBL IDNot Available
ChemSpider ID21482
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkDMDM_hydantoin
References
Synthesis ReferenceNot Available
MSDST3D3627.pdf
General References
  1. de Groot AC, van Joost T, Bos JD, van der Meeren HL, Weyland JW: Patch test reactivity to DMDM hydantoin. Relationship to formaldehyde allergy. Contact Dermatitis. 1988 Apr;18(4):197-201. [3378426 ]
  2. Hippe E, Olesen H, Skouby A: [Occurrence of antibodies against transcobalamin II in relation to the number of and the intervals between depot therapy with hydroxocobalamin]. Nord Med. 1970 Dec 3;84(49):1570. [5488577 ]
  3. Cosmetic Ingredient Review Panel (1988). Final Report on the Safety Assessment of DMDM Hydantoin. J Am Coll Toxicol 7 (3): 245-77.
  4. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
  5. ATSDR - Agency for Toxic Substances and Disease Registry (1999). Toxicological profile for formaldehyde. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  6. Wikipedia. DMDM hydantoin. Last Updated 31 October 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

1. RNA
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (1999). Toxicological profile for formaldehyde. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  2. Wikipedia. DMDM hydantoin. Last Updated 31 October 2009. [Link]
2. DNA
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (1999). Toxicological profile for formaldehyde. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  2. Wikipedia. DMDM hydantoin. Last Updated 31 October 2009. [Link]