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Revision as of 12:32, 20 September 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report errors or [[use← Previous edit Latest revision as of 18:37, 4 May 2023 edit undoGarrettw87 (talk | contribs)Extended confirmed users2,299 editsm updated HPD -> CPID template link 
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{{Short description|Chemical compound}}
{{chembox {{chembox
| verifiedrevid = 451463905 | verifiedrevid = 451492246
|ImageFile=DMDM_hydantoin.svg | ImageFile=DMDM_hydantoin.svg
|ImageSize=150px | ImageSize=
|IUPACName=1,3-Bis(hydroxymethyl)-5,5-dimethylimidazolidine-2,4-dione | PIN=1,3-Bis(hydroxymethyl)-5,5-dimethylimidazolidine-2,4-dione
|OtherNames=1,3-Dimethylol-5,5-dimethylhydantoin<br>Glydant | OtherNames=1,2-Dimethylol-5,6-dimethylhydantoine<br>Glydant
|Section1={{Chembox Identifiers |Section1={{Chembox Identifiers
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
⚫ | Abbreviations=DMDMH
⚫ | CASNo=6440-58-0
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | Abbreviations=DMDMH
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 21482 | ChemSpiderID = 21482
⚫ | PubChem=22947
⚫ | EINECS =229-222-8
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = BYR0546TOW | UNII = BYR0546TOW
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WSDISUOETYTPRL-UHFFFAOYSA-N | StdInChIKey = WSDISUOETYTPRL-UHFFFAOYSA-N
⚫ | SMILES = O=C1N(C(=O)C(N1CO)(C)C)CO
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
⚫ | CASNo=6440-58-0
⚫ | PubChem=22947
⚫ | EINECS =229-222-8
⚫ | SMILES = O=C1N(C(=O)C(N1CO)(C)C)CO
}} }}
|Section2={{Chembox Properties |Section2={{Chembox Properties
| Formula=C<sub>7</sub>H<sub>12</sub>N<sub>2</sub>O<sub>4</sub> | Formula=C<sub>7</sub>H<sub>12</sub>N<sub>2</sub>O<sub>4</sub>
| MolarMass=188.18 g/mol | MolarMass=188.18 g/mol
| Appearance= | Appearance=
| Density= | Density=
| MeltingPt= | MeltingPt=
| BoilingPt= | BoilingPt=
| Solubility= | Solubility=
}} }}
|Section3={{Chembox Hazards |Section3={{Chembox Hazards
| NFPA-H =
⚫ | MainHazards=
| FlashPt= | NFPA-F =
| NFPA-R =
| Autoignition=
⚫ | MainHazards=
| FlashPt=
| AutoignitionPt =
| Hazards_ref=<ref>{{cite web |title=GESTIS-Stoffdatenbank 1,3-Bis(hydroxymethyl)-5,5-dimethylimidazolidin-2,4-dion |url=https://gestis.dguv.de/data?name=120562 |website=gestis.dguv.de}}</ref>
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|302}}
| PPhrases = {{P-phrases|301+312}}
}} }}
}} }}


'''DMDM hydantoin''' is an ] ] ] with the trade name Glydant. DMDM hydantoin is an ] belonging to a class of compounds known as ]s. It is used in the ] industry and found in products like ], ]s, hair gels and skin care products.<ref>{{HPD|2211}}</ref><ref> at sci-toys.com</ref> '''DMDM hydantoin''' is an ] ] ] with the trade name Glydant. DMDM hydantoin is an ] belonging to a class of compounds known as ]s. It is used in the ] industry and found in products like ], ]s, hair gels, and skin care products.<ref>{{CPID|id=711}}</ref><ref> at sci-toys.com</ref>


DMDM hydantoin works as a preservative because the released ] makes the environment less favorable to the ]s. DMDM hydantoin slowly releases ] and works as a preservative by making the environment less favorable to ]s.


==Safety== ==Safety==
Cosmetic Ingredient Review (CIR) Expert Panel has evaluated DMDM hydantoin and concluded "that it was safe to a great majority of consumers but has limited the concentration to 0.2% free formaldehyde due to the skin sensitivity of some individuals to this agent."<ref></ref> A study found "An increase in the use of DMDM hydantoin in cosmetic products will also inevitably increase the risk of cosmetic dermatitis in consumers allergic to formaldehyde."<ref>{{cite journal |journal=Contact Dermatitis |year=1988 |volume=18 |issue=4 |pages=197–201 |title=Patch test reactivity to DMDM hydantoin. Relationship to formaldehyde allergy |author=de Groot AC, van Joost T, Bos JD, van der Meeren HL, Weyland JW |pmid=3378426 |doi=10.1111/j.1600-0536.1988.tb02802.x}}</ref> A ] study found that "an increase in the use of DMDM hydantoin in cosmetic products will also inevitably increase the risk of ] in consumers allergic to formaldehyde."<ref>{{cite journal |journal=Contact Dermatitis |year=1988 |volume=18 |issue=4 |pages=197–201 |title=Patch test reactivity to DMDM hydantoin. Relationship to formaldehyde allergy |vauthors=de Groot AC, van Joost T, Bos JD, van der Meeren HL, Weyland JW |pmid=3378426 |doi=10.1111/j.1600-0536.1988.tb02802.x|s2cid=221577901 }}</ref>

The ] is a topic of ongoing concern, given the prevalence of formaldehyde and formaldehyde releasers in ]. Formaldehyde is considered "an important metabolic product in plants and animals (including humans), where it occurs in low but measurable concentrations."<ref>{{Citation|last1=Franz|first1=Adam W.|title=Formaldehyde|date=2016|url=https://onlinelibrary.wiley.com/doi/abs/10.1002/14356007.a11_619.pub2|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|pages=1–34|publisher=American Cancer Society|language=en|doi=10.1002/14356007.a11_619.pub2|isbn=978-3-527-30673-2|access-date=2021-07-03|last2=Kronemayer|first2=Helmut|last3=Pfeiffer|first3=Daniel|last4=Pilz|first4=Roman D.|last5=Reuss|first5=Gänther|last6=Disteldorf|first6=Walter|last7=Gamer|first7=Armin Otto|last8=Hilt|first8=Albrecht}}</ref> However, long-term exposure to formaldehyde (particularly routine inhalation of its fumes) is thought to cause irritation of the eyes and mucous membranes,<ref>{{Cite web|date=2019-04-11|title=Safety and Health Topics {{!}} Formaldehyde {{!}} Occupational Safety and Health Administration|url=https://www.osha.gov/SLTC/formaldehyde/index.html|access-date=2021-07-03|archive-url=https://web.archive.org/web/20190411185734/https://www.osha.gov/SLTC/formaldehyde/index.html|archive-date=2019-04-11}}</ref> headaches, shortness of breath, and aggravation of asthma symptoms.<ref>{{Cite web|date=2019-03-23|title=Notice of Adoption of Air Toxics Hot Spots Program Technical Support Document for the Derivation of Noncancer Reference Exposure Levels and 6 RELs {{!}} OEHHA|url=https://oehha.ca.gov/air/crnr/notice-adoption-air-toxics-hot-spots-program-technical-support-document-derivation#page=128|access-date=2021-07-03|archive-url=https://web.archive.org/web/20190323081914/https://oehha.ca.gov/air/crnr/notice-adoption-air-toxics-hot-spots-program-technical-support-document-derivation#page=128|archive-date=2019-03-23}}</ref><ref>{{Cite web|last=Canada|first=Health|date=2012-03-29|title=Formaldehyde in your home|url=https://www.canada.ca/en/health-canada/services/environmental-workplace-health/reports-publications/air-quality/formaldehyde-indoor-air-environment-workplace-health.html|access-date=2021-07-03|website=www.canada.ca}}</ref> It was declared a "toxic product" by the 1999 Canadian Environmental Protection Act,<ref>{{Cite web|date=April 2007|title=Health Canada - Proposed residential indoor air quality guidelines for formaldehyde|url=http://www.hc-sc.gc.ca/ewh-semt/pubs/air/formaldehyde/preamble-eng.php|url-status=dead|archive-url=https://web.archive.org/web/20130530085603/http://www.hc-sc.gc.ca/ewh-semt/pubs/air/formaldehyde/preamble-eng.php|archive-date=2013-05-30|access-date=July 3, 2021|website=Health Canada}}</ref> and the US National Toxicology Program officially classed formaldehyde as "known to be a human ] in June 2011.<ref>{{Cite news|last=Harris|first=Gardiner|date=2011-06-10|title=Government Says 2 Common Materials Pose Risk of Cancer|language=en-US|work=The New York Times|url=https://www.nytimes.com/2011/06/11/health/11cancer.html|access-date=2021-07-03|issn=0362-4331}}</ref><ref>{{Cite web|date=2011-06-08|title=Report on Carcinogens (RoC) - National Toxicology Program|url=https://ntp.niehs.nih.gov/index.cfm?objectid=72016262-BDB7-CEBA-FA60E922B18C2540|access-date=2021-07-03|archive-url=https://web.archive.org/web/20110608205825/https://ntp.niehs.nih.gov/index.cfm?objectid=72016262-BDB7-CEBA-FA60E922B18C2540|archive-date=2011-06-08}}</ref><ref>{{Cite web|title=National Toxicology Program: 14th Report on Carcinogens|url=https://ntp.niehs.nih.gov/go/roc14|access-date=2021-07-03|website=National Toxicology Program (NTP)|language=en}}</ref>

In the EU, the maximum allowed concentration of formaldehyde in finished products is 0.2%, and any product that exceeds 0.05% has to include a warning that the product contains formaldehyde.<ref>{{Cite journal|last1=Groot|first1=Anton C. de|last2=Flyvholm|first2=Mari-ann|last3=Lensen|first3=Gerda|last4=Menne|first4=Torkil|last5=Coenraads|first5=Pieter-Jan|date=2009|title=Formaldehyde-releasers: relationship to formaldehyde contact allergy. Contact allergy to formaldehyde and inventory of formaldehyde-releasers|url=https://research.rug.nl/en/publications/formaldehyde-releasers-relationship-to-formaldehyde-contact-aller-2|journal=Contact Dermatitis|language=English|volume=61|issue=2|pages=63–85|doi=10.1111/j.1600-0536.2009.01582.x|pmid=19706047|s2cid=23404196|issn=0105-1873|hdl=11370/c3ff7adf-9f21-4564-96e0-0b9c5d025b30|hdl-access=free}}</ref>


== References == == References ==
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