6440-58-0
Chemical Structure
DMDM hydantoin
Synonym(s): Dimethyloldimethyl hydantoin
- CAS No.: 6440-58-0
- Formula:C7H12N2O4
- Molecular Weight:188.18
IUPAC Name: 1,3-bis(hydroxymethyl)-5,5-dimethylimidazolidine-2,4-dione
InChIKey: WSDISUOETYTPRL-UHFFFAOYSA-N
SMILES: O=C1N(C(=O)C(N1CO)(C)C)CO
Biological Activity: DMDM hydantoin (Dimethyloldimethyl hydantoin) is a hydantoin-derived formaldehyde-releasing preservative and allergen. DMDM hydantoin releases formaldehyde via hydrolysis in water, including under physiological pH conditions, and the release amount is affected by pH, concentration, composition, temperature and storage duration. DMDM hydantoin exerts bactericidal effects by mediating the cross-linking of proteins, RNA and DNA through the released formaldehyde, thereby inhibiting metabolism and cell division. DMDM hydantoin can induce allergic contact dermatitis directly, via the released formaldehyde, or through both pathways simultaneously. DMDM hydantoin is skin-irritating, and the released formaldehyde brings toxicological risks including carcinogenicity, mutagenicity and reproductive toxicity after entering the body. DMDM hydantoin can be used in studies related to allergic contact dermatitis[1][2][3][4].
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DMDM hydantoin | DMDM hydantoin (Dimethyloldimethyl hydantoin) is a hydantoin-derived formaldehyde-releasing preservative and allergen. DMDM hydantoin releases formaldehyde via hydrolysis in water, including under physiological pH conditions, and the release amount is affected by pH, concentration, composition, temperature and storage duration. DMDM hydantoin exerts bactericidal effects by mediating the cross-linking of proteins, RNA and DNA through the released formaldehyde, thereby inhibiting metabolism and cell division. DMDM hydantoin can induce allergic contact dermatitis directly, via the released formaldehyde, or through both pathways simultaneously. DMDM hydantoin is skin-irritating, and the released formaldehyde brings toxicological risks including carcinogenicity, mutagenicity and reproductive toxicity after entering the body. DMDM hydantoin can be used in studies related to allergic contact dermatitis. | |||||||||||||||||||||
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References
- [1]. Nguyen HL, et al. Contact Dermatitis to Medications and Skin Products. Clinical reviews in allergy & immunology. 2019 Feb;56(1):41-59. [Content Brief]
- [2]. de Groot A, et al. Formaldehyde-releasers in cosmetics: relationship to formaldehyde contact allergy. Part 2. Patch test relationship to formaldehyde contact allergy, experimental provocation tests, amount of formaldehyde released, and assessment of risk to consumers allergic to formaldehyde. Contact Dermatitis. 2010 Jan;62(1):18-31. [Content Brief]
- [3]. Kireche M, et al. Preservatives in cosmetics: reactivity of allergenic formaldehyde-releasers towards amino acids through breakdown products other than formaldehyde. Contact dermatitis. 2010 Oct;63(4):192-202.
- [4]. López-Sánchez L, et al. In vitro skin penetration of bronidox, bronopol and formaldehyde from cosmetics. Regulatory toxicology and pharmacology : RTP. 2021 Jun;122:104888.
