# Bis-GMA

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Bis-GMA
> Markdown URL: https://mediated.wiki/source/Bis-GMA.md
> Source: https://en.wikipedia.org/wiki/Bis-GMA
> Source revision: 1314496690
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{{Chembox
|ImageFile = MethmethacrylateBPA-glyc.png
|PIN = Propane-2,2-diylbis[4,1-phenyleneoxy(2-hydroxypropane-3,1-diyl)] bis(2-methylprop-2-enoate)
|OtherNames = Bowen monomer; Silux; Delton; NuvaSeal; Retroplast
|Section1={{Chembox Identifiers
|CASNo = 1565-94-2
|CASNo_Ref = {{cascite|correct|CAS}}
|ChemSpiderID = 14549
|EINECS = 216-367-7
|UNII_Ref = {{fdacite|correct|FDA}}
|UNII = 454I75YXY0
|PubChem = 15284
|StdInChI=1S/C29H36O8/c1-19(2)27(32)36-17-23(30)15-34-25-11-7-21(8-12-25)29(5,6)22-9-13-26(14-10-22)35-16-24(31)18-37-28(33)20(3)4/h7-14,23-24,30-31H,1,3,15-18H2,2,4-6H3
|StdInChIKey = AMFGWXWBFGVCKG-UHFFFAOYSA-N
|SMILES = CC(=C)C(=O)OCC(COC1=CC=C(C=C1)C(C)(C)C2=CC=C(C=C2)OCC(COC(=O)C(=C)C)O)O
}}
|Section2={{Chembox Properties
|C=29|H=36|O=8 
|Appearance = colorless oil
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|Section3={{Chembox Hazards
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|GHSSignalWord = Danger
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'''Bis-GMA''' (bisphenol A-glycidyl methacrylate) is a [resin](/source/resin) commonly used in [dental composite](/source/dental_composite), [dental sealant](/source/dental_sealant)s.<ref>{{PubChem|15284}}. Retrieved 27 May 2022.</ref><ref name=":0">{{Cite journal|last1=Ahovuo-Saloranta|first1=Anneli|last2=Forss|first2=Helena|last3=Walsh|first3=Tanya|last4=Nordblad|first4=Anne|last5=Mäkelä|first5=Marjukka|last6=Worthington|first6=Helen V.|date=31 July 2017|title=Pit and fissure sealants for preventing dental decay in permanent teeth|journal=The Cochrane Database of Systematic Reviews|volume=2017|issue=7 |article-number=CD001830|doi=10.1002/14651858.CD001830.pub5 |pmc=6483295|pmid=28759120}}</ref> and [dental cement](/source/dental_cement). It is the [diester](/source/diester) derived from [methacrylic acid](/source/methacrylic_acid) and the [bisphenol A diglycidyl ether](/source/bisphenol_A_diglycidyl_ether).  Bearing two polymerizable groups, it is prone to form a crosslinked polymer that is used in dental restorations.<ref name="Ull">{{Ullmann|title=Dental Materials|year=2006|doi=10.1002/14356007.a08_251.pub2|vauthors=Craig RG, Welker D, Rothaut J, Krumbholz KG, Stefan KP, Dermann K, Rehberg HJ, Franz G, Lehmann KM, Borchert M}}</ref>  For dental work, highly viscous bis-GMA is mixed with aluminosilicate particles, crushed quartz and other related acrylates; changes to component ratios lead to different physical properties in the end product.<ref>{{Cite journal |vauthors=Zimmerli B, Strub M, Jeger F, Stadler O, Lussi A |date=November 2010 |title=Composite Materials: Composition, properties and clinical applications |url=https://www.sso.ch/pubmed.cfm?a=smfz-2010-11-30 |format=PDF |journal=Schweiz Monatsschr Zahnmed |volume=120 |issue=11 |pages=972&ndash;9 |pmid=21243545 |access-date=28 May 2022}}</ref> Bis-GMA was incorporated into composite dental resins in 1962 by Rafael Bowen.<ref name=Ull/>  Until matrix development work in the early 2000s, bis-GMA and related methacrylate monomers were the only options for organic matrix composition.<ref>{{Cite journal |vauthors=Fugolin AP, Pfeifer CS |date=21 July 2017 |title=New Resins for Dental Composites |journal=[Journal of Dental Research](/source/Journal_of_Dental_Research) |volume=96 |issue=10 |pages=1085&ndash;91 |doi=10.1177/0022034517720658 |pmid=28732183 |pmc=5582688 }}</ref>

==Safety==
Concerns have been raised about the potential for bis-GMA to break down into or be contaminated with the related compound [bisphenol A](/source/bisphenol_A).<ref name=Labauve2012>{{cite journal|vauthors=LaBauve JR, Long KN, Hack GD, Bashirelahi N |title=What every dentist should known about bisphenol A |journal=General Dentistry |volume=60 |issue=5 |date=2012 |pmid=23032231 |pages=424–32 }}</ref> However, no negative health effects of bis-GMA use in dental resins have been found.<ref name=":0" /><ref name=Soderholm1999>{{cite journal|vauthors=Soderholm KJ, Mariotti A |title=Bis-GMA–based resins in dentistry: are they safe?|journal=The Journal of the American Dental Association|date=February 1999|volume=130|issue=2|pages=201–209|doi=10.14219/jada.archive.1999.0169|pmid=10036843}}{{Subscription required}}</ref>

==Composition==
[Saliva](/source/Saliva)ry [esterase](/source/esterase)s can slowly degrade bis-GMA-based sealants, forming [Bis-HPPP](/source/Bis-HPPP).<ref>{{cite journal|last1=Shokati|first1=Babak|last2=Tam|first2=Laura Eva|last3=Santerre|first3=J. Paul|last4=Finer|first4=Yoav|title=Effect of salivary esterase on the integrity and fracture toughness of the dentin-resin interface|journal=Journal of Biomedical Materials Research Part B: Applied Biomaterials|date=2010|volume=94|issue=1|pages=230–7|doi=10.1002/jbm.b.31645|pmid=20524199}}</ref>

==References==
{{Reflist}}

== Further reading ==
* {{Cite journal |last=Rochester |first=Johanna R. |date=30 August 2013 |title=Bisphenol A and human health: a review of the literature |journal=[Reproductive Toxicology](/source/Reproductive_Toxicology_(journal)) |volume=42 |pages=132&ndash;155 |doi=10.1016/j.reprotox.2013.08.008 |pmid=23994667 |bibcode=2013RepTx..42..132R }}

Category:Dental materials
Category:2,2-Bis(4-hydroxyphenyl)propanes
Category:Enones

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Adapted from the Wikipedia article [Bis-GMA](https://en.wikipedia.org/wiki/Bis-GMA) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Bis-GMA?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.