Diazolidinyl urea

Diazolidinyl urea
	; newly determined structure
	; "traditional" structure
Names
	IUPAC names 1-[3,4-bis(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl]-1,3-bis(hydroxymethyl)urea (new); 1-[1,3-bis(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl]-1,3-bis(hydroxymethyl)urea (old)
	Other names Diazolidinylurea; Germall II
Identifiers
CAS Number	78491-02-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	56078 ;
ECHA InfoCard	100.071.732
EC Number	278-928-2;
PubChem CID	62277;
UNII	H5RIZ3MPW4 ;
CompTox Dashboard (EPA)	DTXSID0029559 ;
	InChI InChI=1S/C8H14N4O7/c13-1-9-7(18)10(2-14)5-6(17)12(4-16)8(19)11(5)3-15/h5,13-16H,1-4H2,(H,9,18) Key: SOROIESOUPGGFO-UHFFFAOYSA-N ; InChI=1/C8H14N4O7/c13-1-9-7(18)10(2-14)5-6(17)12(4-16)8(19)11(5)3-15/h5,13-16H,1-4H2,(H,9,18) Key: SOROIESOUPGGFO-UHFFFAOYAO;
	SMILES O=C1N(C(=O)C(N(C(=O)NCO)CO)N1CO)CO;
Properties
Chemical formula	C8H14N4O7
Molar mass	278.22 g/mol
Hazards
	GHS labelling:
Signal word	Warning
Hazard statements	H317
Precautionary statements	P261, P272, P280, P302+P352, P321, P333+P313, P363, P501
NFPA 704 (fire diamond)	1 1 0
Related compounds
Related compounds	Imidazolidinyl urea
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Diazolidinyl urea is an antimicrobial preservative used in cosmetics. It is chemically related to imidazolidinyl urea which is used in the same way. Diazolidinyl urea acts as a formaldehyde releaser.

It is used in many cosmetics, skin care products, shampoos and conditioners, as well as a wide range of products including bubble baths, baby wipes and household detergents. Diazolidinyl urea is found in the commercially available preservative Germaben.

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

Chemistry

Synthesis

Diazolidinyl 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:

+ 4 H₂C=O →

Structure

Diazolidinyl 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 one of the hydroxymethyl functional groups of the imidazolidine ring is attached to the carbon, rather than on the urea nitrogen atom:^[2]


Originally reported structure	Hoeck's revised structure

Safety

Some people have a contact allergy to imidazolidinyl urea causing dermatitis.^[3] Such people are often also allergic to diazolidinyl urea.

In addition to being an allergen, it is a formaldehyde releaser, since it generates formaldehyde slowly as it degrades. Although the formaldehyde acts as a bactericidal preservative, it is a known carcinogen.

In 2005–06, it was the 14th-most-prevalent allergen in patch tests (3.7%).^[4]

References

^ HSNO Chemical Classification Information Database, New Zealand Environmental Risk Management Authority, retrieved 2009-09-06
^ ^a ^b Lehmann, Søren Vig; Hoeck, Ulla; Breinholdt, Jens; Olsen, Carl Erik; Kreilgaard, Bo (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.
^ Review of toxicological data (NTP NIEHS)
^ Zug, K. A.; Warshaw, E. M.; Fowler, J. F. Jr; Maibach, H. I.; Belsito, D. L.; Pratt, M. D.; Sasseville, D.; Storrs, F. J.; Taylor, J. S.; Mathias, C. G.; Deleo, V. A.; Rietschel, R. L.; Marks, J. (May–June 2009). "Patch-test results of the North American Contact Dermatitis Group 2005–2006". Dermatitis. 20 (3): 149–160.

[1] HSNO Chemical Classification Information Database, New Zealand Environmental Risk Management Authority, retrieved 2009-09-06

[structure-2] Lehmann, Søren Vig; Hoeck, Ulla; Breinholdt, Jens; Olsen, Carl Erik; Kreilgaard, Bo (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.

[NIEHS-3] Review of toxicological data (NTP NIEHS)

[4] Zug, K. A.; Warshaw, E. M.; Fowler, J. F. Jr; Maibach, H. I.; Belsito, D. L.; Pratt, M. D.; Sasseville, D.; Storrs, F. J.; Taylor, J. S.; Mathias, C. G.; Deleo, V. A.; Rietschel, R. L.; Marks, J. (May–June 2009). "Patch-test results of the North American Contact Dermatitis Group 2005–2006". Dermatitis. 20 (3): 149–160.

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