1-Monomethylol-5,5-dimethylhydantoin
Basic information
- CAS
116-25-6- Standard SMILES
CC1(C)C(=O)NC(=O)N1CO- InChIKey
SIQZJFKTROUNPI-UHFFFAOYSA-N- Molecular formula
- C6H10N2O3
- Average molar mass
- 158.16 g/mol
- Monoisotopic mass
- 158.06914219
Overview
1-(hydroxymethyl)-5,5-dimethylhydantoin is an imidazolidine-2,4-dione substituted by a hydroxymethyl group at position 1 and two methyl groups at position 5. It is approved by the FDA for use as an adjuvant in the bleaching of recycled paper and board used in food packaging, and is also a decomposition product of DMDM hydantoin, a preservative and antimicrobial agent used in cosmetics and personal care products. It has a role as an antimicrobial agent. It is an imidazolidine-2,4-dione and a hemiaminal.
Names & identifiers
- Preferred name
- 1-Monomethylol-5,5-dimethylhydantoin
- IUPAC
- 1-(hydroxymethyl)-5,5-dimethylimidazolidine-2,4-dione
- English name
- 1-Methylol-5,5-dimethylhydantoin
- Molecular formula
- C6H10N2O3
- Molecular weight
- 158.16
Names & synonyms
1-Monomethylol-5,5-dimethylhydantoinRefChem:74700116-25-61-(Hydroxymethyl)-5,5-dimethylhydantoin1-(hydroxymethyl)-5,5-dimethylimidazolidine-2,4-dioneMDM Hydantoin1-Hydroxymethyl-5,5-dimethylhydantoinMDMHGlycoServeMonomethyloldimethylhydantoinDantoin MDMH27636-82-4
Show more names
Methyldimethylhydantoin1-hydroxymethyl-5,5-dimethylMONO-METHYLOLDIMETHYLHYDANTOIN5,5-dimethyl-1-methylol-hydantoin1,1-METHYLOL-5,5-DIMETHYLHYDANTOIN
methylol dimethylhydantoinMDM Hydantoin (VAN)1-(Hydroxymethyl)-5,5-dimethyl-2,4-imidazolidinedione1-Methylol-5,5-dimethylhydantoinHydroxymethyl-5,5-dimethylhydantoin2,4-Imidazolidinedione, 1-(hydroxymethyl)-5,5-dimethyl-Monomethylol dimethyl hydantoin5,5-Dimethyl-1-hydroxymethylhydantoin
Database identifiers
- CAS
116-25-6、27636-82-4
Properties
Computed structural properties
- XLogP
- -0.3
- Topological polar surface area
- 69.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 212
Experimental & physicochemical properties
CosmeticsAntimicrobial
SolubilityFreely soluble
Melting Point110 - 117 °C
Food Contact SubstancesFCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 104 · 104-106°C
- Density
- 1.257 · 1.257±0.06 g/cm3(Predicted)
- storage temp.
- Hygroscopic, Refrigerator, under inert atmosphere
- solubility
- DMSO (Heated), Methanol (Slightly)
- form
- Solid
- pka
- 8.28 · 8.28±0.10(Predicted)
- color
- White to Off-White
- Water Solubility
- Freely soluble in water.
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 53.8% (77 of 143) of all reports.
Warning
H302 (42.7%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P272, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 143 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
This chemical does not meet GHS hazard criteria for 100% (38 of 38) of all reports.
Hazard information
Regulatory Information
Chemical: 2,4-Imidazolidinedione, 1-(hydroxymethyl)-5,5-dimethyl-
2,4-Imidazolidinedione, 1-(hydroxymethyl)-5,5-dimethyl-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
2,4-Imidazolidinedione, (hydroxymethyl)-5,5-dimethyl-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Other Safety InformationEvaluation - Hydroxymethylated imidazolidinones
Hazard Classes and Categories
Acute Tox. 4 (42.7%)
Not Classified
Safety data
- tsca
- TSCA listed
- rtecs
- NI9454200
- hs_code
- 2933210090
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Uses & manufacturing
Household ProductsInformation on 6 consumer products that contain 2,4-Imidazolidinedione, (hydroxymethyl)-5,5-dimethyl- in the following categories is provided:
Use ClassificationCosmetics -> Antimicrobial
General Manufacturing Information2,4-Imidazolidinedione, 1-(hydroxymethyl)-5,5-dimethyl-: ACTIVE
Applications
Uses1-Hydroxymethyl-5,5-dimethylhydantoin is used as chelator for light-sensitive pharmaceutical drug, and as raw material of water-soluble polymers. It also can be used as a soluble inhibitor for proteins. It is used as an adjuvant in the bleaching of food-contact recycled paper and board used in food packaging.
Additional notes
DefinitionChEBI: 1-(hydroxymethyl)-5,5-dimethylhydantoin is an imidazolidine-2,4-dione substituted by a hydroxymethyl group at position 1 and two methyl groups at position 5. It is approved by the FDA for use as an adjuvant in the bleaching of recycled paper and board used in food packaging, and is also a decomposition product of DMDM hydantoin, a preservative and antimicrobial agent used in cosmetics and personal care products. It has a role as an antimicrobial agent. It is an imidazolidine-2,4-dione and a hemiaminal.
Related reactions
5 records
Compound notes
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