Diazolidinyl urea

Last updated
Diazolidinyl urea
Diazolidinyl urea correct formula.png
newly determined structure
Diazolidinyl urea erroneous formula.png
"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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.071.732 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 278-928-2
PubChem CID
UNII
  • 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) Yes check.svgY
    Key: SOROIESOUPGGFO-UHFFFAOYSA-N Yes check.svgY
  • 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
  • O=C1N(C(=O)C(N(C(=O)NCO)CO)N1CO)CO
Properties
C8H14N4O7
Molar mass 278.22 g/mol
Hazards GHS-pictogram-exclam.svg [1]
GHS labelling:
Warning
H317
P261, P272, P280, P302+P352, P321, P333+P313, P363, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

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:

Allantoin.svg + 4 H2C=O → Diazolidinyl urea correct formula.png

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]

Diazolidinyl urea erroneous formula.png Diazolidinyl urea correct formula.png
Originally reported structureHoeck'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]

Related Research Articles

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Methylchloroisothiazolinone, also referred to as MCI, is the organic compound with the formula S(C2HCl)C(O)N(CH3). It is a white solid that melts near room temperature. The compound is an isothiazolinone, a class of heterocycles used as biocides. These compounds have an active sulphur moiety that is able to oxidize thiol-containing residues, thereby effectively killing most aerobic and anaerobic bacteria. MCI is often used in combination with methylisothiazolinone, a mixture known as Kathon. The isothiazolinones have attracted attention because they can cause contact dermatitis. Methylchloroisothiazolinone is effective against gram-positive and gram-negative bacteria, yeast, and fungi.

<span class="mw-page-title-main">Formaldehyde</span> Organic compound (H–CHO); simplest aldehyde

Formaldehyde ( for-MAL-di-hide, fər-) (systematic name methanal) is an organic compound with the chemical formula CH2O and structure H−CHO, more precisely H2C=O. The compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde. It is stored as aqueous solutions (formalin), which consists mainly of the hydrate CH2(OH)2. It is the simplest of the aldehydes (R−CHO). As a precursor to many other materials and chemical compounds, in 2006 the global production of formaldehyde was estimated at 12 million tons per year. It is mainly used in the production of industrial resins, e.g., for particle board and coatings. Small amounts also occur naturally.

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<span class="mw-page-title-main">Methylisothiazolinone</span> Chemical compound

Methylisothiazolinone, MIT, or MI, is the organic compound with the formula S(CH)2C(O)NCH3. It is a white solid. Isothiazolinones, a class of heterocycles, are used as biocides in numerous personal care products and other industrial applications. MIT and related compounds have attracted much attention for their allergenic properties, e.g. contact dermatitis.

<span class="mw-page-title-main">Contact dermatitis</span> Human disease

Contact dermatitis is a type of acute or chronic inflammation of the skin caused by exposure to chemical or physical agents. Symptoms of contact dermatitis can include itchy or dry skin, a red rash, bumps, blisters, or swelling. These rashes are not contagious or life-threatening, but can be very uncomfortable.

<span class="mw-page-title-main">Quaternium-15</span> Salt used as a surfactant

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<span class="mw-page-title-main">Bronopol</span> Chemical compound

Bronopol is an organic compound that is used as an antimicrobial. It is a white solid although commercial samples appear yellow.

<span class="mw-page-title-main">Patch test</span> Medical test to determine substances causing allergic reactions

A patch test is a diagnostic method used to determine which specific substances cause allergic inflammation of a patient's skin.

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<span class="mw-page-title-main">Imidazolidinyl urea</span> Chemical compound

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.

<span class="mw-page-title-main">Formaldehyde releaser</span> Chemical compound used as a preservative that slowly releases formaldehyde.

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DMDM hydantoin is an antimicrobial formaldehyde releaser preservative with the trade name Glydant. DMDM hydantoin is an organic compound belonging to a class of compounds known as hydantoins. It is used in the cosmetics industry and found in products like shampoos, hair conditioners, hair gels, and skin care products.

Eyelid dermatitis is commonly related to atopic dermatitis or allergic contact dermatitis. Volatile substances, tosylamide, epoxy hardeners, insect sprays, and lemon peel oil may be implicated, with many cases of eyelid contact dermatitis being caused by substances transferred by the hands to the eyelids.

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<span class="mw-page-title-main">Iodopropynyl butylcarbamate</span> Chemical compound

Iodopropynyl Butyl Carbamate (IPBC) is a water-soluble preservative used globally in the paints & coatings, wood preservatives, personal care, and cosmetics industries. IPBC is a member of the carbamate family of biocides. IPBC was invented in the 1970s and has a long history of effective use as an antifungal technology.

The Human maximisation test (HMT) is a test method for testing for contact allergens. It was first developed by Albert Kligman in 1966 and updated by Kligman and William Epstein in 1975. The first paper appeared 1966 and was a citation classic in 1985.

<span class="mw-page-title-main">Methyldibromo glutaronitrile</span> Chemical compound

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<span class="mw-page-title-main">Tetramethyl acetyloctahydronaphthalenes</span> Chemical compound

Tetramethyl acetyloctahydronaphthalenes is a synthetic ketone fragrance also known as OTNE and by other commercial trade names such as: Iso E Super, Iso Gamma Super, Anthamber, Amber Fleur, Boisvelone, Iso Ambois, Amberlan, Iso Velvetone, Orbitone, Amberonne. It is a synthetic woody odorant and is used as a fragrance ingredient in perfumes, laundry products and cosmetics.

References

  1. ↑ HSNO Chemical Classification Information Database, New Zealand Environmental Risk Management Authority, retrieved 2009-09-06
  2. 1 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.
  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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