Imidazolidinyl urea

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.

Imidazolidinyl urea
Names
IUPAC names
Correct new structure (upper pic.):
1,1′-methylenebis{3-[4-(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl]urea}
Erroneous old structure (lower pic.):
1,1′-methylenebis{3-[1-(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl]urea}
Other names
Imidurea, Germall 115;

N′,N″-methylenebis[3-[1-(hydroxymethyl)- 2,5-dioxoimidazolidin-4-yl]urea];

1-[1-(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl]- 3-[[[1-(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl] carbamoylamino]methyl]urea
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.049.411
EC Number
  • 254-372-6
UNII
  • 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) checkY
    Key: ZCTXEAQXZGPWFG-UHFFFAOYSA-N checkY
  • 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
  • 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
C11H16N8O8
Molar mass 388.29 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Safety

Some people have a contact allergy to imidazolidinyl urea causing dermatitis.[1] Such people are often also allergic to diazolidinyl urea.

Chemistry

Imidazolidinyl urea was poorly characterized until recently and the single Chemical Abstracts Service structure assigned to it is probably not the major one in the commercial material. Instead, new data indicate that the hydroxymethyl functional group of each imidazolidine ring is attached to the carbon, rather than on the nitrogen atom:[2]

Originally reported structure Hoeck's revised structure
Originally reported structure Hoeck's revised 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.[2]

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. S2CID 25897828.
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