Imidazolidinyl urea

Last updated
Imidazolidinyl urea
Imidazolidinyl urea correct formula.png
Imidazolidinyl urea erroneous formula.png
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

Contents

Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.049.411 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 254-372-6
PubChem CID
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) Yes check.svgY
    Key: ZCTXEAQXZGPWFG-UHFFFAOYSA-N Yes check.svgY
  • 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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Imidazolidinyl urea is an antimicrobial preservative used in cosmetics [ citation needed ]. 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. [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]

Imidazolidinyl urea erroneous formula.png Imidazolidinyl urea correct formula.png
Originally reported structureHoeck'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.svg + 3 H2C=O → Imidazolidinyl urea correct formula.png

Commercial imidazolidinyl urea is a mixture of different formaldehyde addition products including polymers. [2]

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References

  1. Review of toxicological data (NTP NIEHS)
  2. 1 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.