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Imidazolidinyl urea

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Imidazolidinyl urea
Names
IUPAC names Correct new structure (upper pic.):
1,1'-methylenebis{3-urea}
Erroneous old structure (lower pic.):
1,1'-methylenebis{3-urea}
Other names Imidurea, Germall 115;

N',N''-methylenebisurea];

1-- 3- carbamoylamino]methyl]urea
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.049.411 Edit this at Wikidata
EC Number
  • 254-372-6
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C11H16N8O8/c20-2-18-4(6(22)16-10(18)26)14-8(24)12-1-13-9(25)15-5-7(23)17-11(27)19(5)3-21/h4-5,20-21H,1-3H2,(H2,12,14,24)(H2,13,15,25)(H,16,22,26)(H,17,23,27)Key: ZCTXEAQXZGPWFG-UHFFFAOYSA-N
  • InChI=1/C11H16N8O8/c20-2-18-4(6(22)16-10(18)26)14-8(24)12-1-13-9(25)15-5-7(23)17-11(27)19(5)3-21/h4-5,20-21H,1-3H2,(H2,12,14,24)(H2,13,15,25)(H,16,22,26)(H,17,23,27)Key: ZCTXEAQXZGPWFG-UHFFFAOYAS
SMILES
  • O=C2N(CO)C(NC(=O)NCNC(=O)NC1C(=O)NC(=O)N1CO)C(=O)N2
  • C(NC(=O)NC1C(=O)NC(=O)N1CO)NC(=O)NC2C(=O)NC(=O)N2CO
Properties
Chemical formula C11H16N8O8
Molar mass 388.29 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound
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Imidazolidinyl urea is an antimicrobial preservative used in cosmetics . It is chemically related to diazolidinyl urea which is used in the same way. Imidazolidinyl urea acts as a formaldehyde releaser.

Safety

Some people have a contact allergy to imidazolidinyl urea causing dermatitis. Such people are often also allergic to diazolidinyl urea.

Chemistry

Imidazolidinyl urea was poorly characterized until recently and still has a wrong CAS structure assigned to it. New data show that the hydroxymethyl functional group of the imidazolidine ring is attached to the carbon, not the nitrogen atom :

Imidazolidinyl urea (correct new structure) Imidazolidinyl urea (erroneous old structure)
Correct new structure Erroneous old structure

Synthesis

Imidazolidinyl urea is produced by the chemical reaction of allantoin and formaldehyde in the presence of sodium hydroxide solution and heat. The reaction mixture is then neutralized with hydrochloric acid and evaporated:

2 Allantoin + 3 H2C=O → Imidazolidinyl urea

Commercial imidazolidinyl urea is a mixture of different formaldehyde addition products including polymers.

References

  1. Review of toxicological data (NTP NIEHS)
  2. ^ Lehmann SV, Hoeck U, Breinholdt J, Olsen CE, Kreilgaard B. (2006). "Characterization and chemistry of imidazolidinyl urea and diazolidinyl urea". Contact Dermatitis. 54 (1): 50–58. doi:10.1111/j.0105-1873.2006.00735.x. PMID 16426294.{{cite journal}}: CS1 maint: multiple names: authors list (link)
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