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{{Orphan|date=February 2009}} |
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{{chembox |
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{{chembox |
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|Verifiedfields = changed |
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| Name = Bis-HPPP |
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|Watchedfields = changed |
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| ImageFile = Bis-HPPP.PNG |
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|verifiedrevid = 424942077 |
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| ImageSize = 200px |
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|Name = Bis-HPPP |
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| ImageName = |
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|ImageFile = Bis-HPPP.svg |
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| IUPACName = 2,2-bispropane |
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|ImageSize = 200px |
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| Section1 = {{Chembox Identifiers |
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|PIN = 3,3′-di(propane-1,2-diol) |
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| CASNo = 116-37-0 |
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|OtherNames = BADGE·2H<sub>2</sub>O |
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| SMILES = OCC(O)COc1ccc(cc1)C(C)(C)c2ccc(OCC(O)CO)cc2 |
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|Section1 = {{Chembox Identifiers |
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}} |
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|CASNo = 5581-32-8 |
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| Section2 = {{Chembox Properties |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| Formula = C<sub>21</sub>H<sub>28</sub>O<sub>6</sub> |
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|UNII = S5K2510L3D |
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| MolarMass = 376.44 g/mol |
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|SMILES = OCC(O)COc1ccc(cc1)C(C)(C)c2ccc(OCC(O)CO)cc2 |
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| Density = |
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|PubChem = 110678 |
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| MeltingPt = |
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|ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| BoilingPt = |
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|ChemSpiderID = 99341 |
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}} |
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|InChI = 1/C21H28O6/c1-21(2,15-3-7-19(8-4-15)26-13-17(24)11-22)16-5-9-20(10-6-16)27-14-18(25)12-23/h3-10,17-18,22-25H,11-14H2,1-2H3 |
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|InChIKey = NISVZEWKUNUGQQ-UHFFFAOYAT |
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|StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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|StdInChI = 1S/C21H28O6/c1-21(2,15-3-7-19(8-4-15)26-13-17(24)11-22)16-5-9-20(10-6-16)27-14-18(25)12-23/h3-10,17-18,22-25H,11-14H2,1-2H3 |
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|StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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|StdInChIKey = NISVZEWKUNUGQQ-UHFFFAOYSA-N |
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|Section2 = {{Chembox Properties |
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|C = 21 | H = 28 | O = 6 |
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'''Bis-HPPP''' ('''2,2-bispropane''') is an ] that is formed when the ] material ] is degraded by ] ]s.<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> It is also called '''BADGE·2H<sub>2</sub>O''' in reference to it being the hydrolyzed form of ], which is used in the formation of ].<ref>{{cite journal |last1=Yonekubo |first1=Jun |last2=Hayakawa |first2=Kazuichi |last3=Sajiki |first3=Junko |title=Concentrations of Bisphenol A, Bisphenol A Diglycidyl Ether, and Their Derivatives in Canned Foods in Japanese Markets |journal=Journal of Agricultural and Food Chemistry |date=1 March 2008 |volume=56 |issue=6 |pages=2041–2047 |doi=10.1021/jf073106n}}</ref> Structurally, it is a di-] of ]. |
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'''2,2-Bispropane''' ('''bis-HPPP''') is an organic compound structurally related to ]. |
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== Formation == |
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Together with ], bis-HPPP is released following the CE-catalyzed hydrolysis of 2,2-propane (bis-GMA). This reaction is very common in hydrolytic degradation of the dental resin since salivary esterases are able to cleave the ester bonds in ] polymers of dental composites. |
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Together with ], bis-HPPP is released following the CE-catalyzed{{huh|date=April 2022}} hydrolysis of 2,2-propane (bis-GMA). This reaction is very common in hydrolytic degradation of the dental resin since salivary esterases are able to cleave the ester bonds in ] polymers of dental composites. |
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Analysis by ] demonstrated that ] reactions would cleave the ] bonds of both methacrylate units in bis-GMA and produce bis-HPPP along with two molecules of methacrylic acid.<ref>{{cite journal | author = Finer Y, S.J. | title = The influence of resin chemistry on a dental composite's biodegradation | journal = ] | year = 2004 | volume = 69A | pages = 233–246 | doi = 10.1002/jbm.a.30000 | pmid = 15057996 | last2 = Santerre | first2 = JP | issue = 2}}</ref> |
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Analysis by ] demonstrated that ] reactions would cleave the ] bonds of both methacrylate units in bis-GMA and produce bis-HPPP along with two molecules of methacrylic acid.<ref>{{cite journal | author = Finer Y, S.J. | title = The influence of resin chemistry on a dental composite's biodegradation | journal = ] | year = 2004 | volume = 69A | pages = 233–246 | doi = 10.1002/jbm.a.30000 | pmid = 15057996 | last2 = Santerre | first2 = JP | issue = 2| doi-access = free }}</ref> |
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==References== |
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==References== |
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