Bis-GMA
{{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
}}
|Section3={{Chembox Hazards
|GHSPictograms = {{GHS05}}{{GHS07}}
|GHSSignalWord = Danger
|HPhrases = {{H-phrases|315|317|318|319}}
|PPhrases = {{P-phrases|261|264|272|280|302+352|305+351+338|310|321|332+313|333+313|337+313|362|363|501}}
}}
}}
Bis-GMA (bisphenol A-glycidyl methacrylate) is a resin commonly used in dental composite, dental sealants.{{PubChem|15284}}. Retrieved 27 May 2022.{{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 |pages=CD001830|doi=10.1002/14651858.CD001830.pub5|issn=1469-493X|pmc=6483295|pmid=28759120}} and dental cement. It is the diester derived from methacrylic acid and the bisphenol A diglycidyl ether. Bearing two polymerizable groups, it is prone to form a crosslinked polymer that is used in dental restorations.{{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}} 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.{{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=972–9 |pmid=21243545 |access-date=28 May 2022}} Bis-GMA was incorporated into composite dental resins in 1962 by Rafael Bowen. Until matrix development work in the early 2000s, bis-GMA and related methacrylate monomers were the only options for organic matrix composition.{{Cite journal |vauthors=Fugolin AP, Pfeifer CS |date=21 July 2017 |title=New Resins for Dental Composites |journal=Journal of Dental Research |volume=96 |issue=10 |pages=1085–91 |doi=10.1177/0022034517720658 |pmid=28732183 |pmc=5582688 }}
Safety
Concerns have been raised about the potential for bis-GMA to break down into or be contaminated with the related compound bisphenol A.{{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 }} However, no negative health effects of bis-GMA use in dental resins have been found.{{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}}
Composition
Salivary esterases can slowly degrade bis-GMA-based sealants, forming Bis-HPPP.{{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}}
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 |url=https://www.sciencedirect.com/science/article/abs/pii/S0890623813003456 |journal=Reproductive Toxicology |volume=42 |pages=132–155 |doi=10.1016/j.reprotox.2013.08.008 |pmid=23994667 |url-access=limited |via=ScienceDirect}}