Bis-HPPP

Bis-HPPP
Names
	Preferred IUPAC name 3,3′-[Propane-2,2-diylbis(4,1-phenyleneoxy)]di(propane-1,2-diol)
	Other names BADGE·2H2O
Identifiers
CAS Number	5581-32-8;
3D model (JSmol)	Interactive image;
ChemSpider	99341 ;
ECHA InfoCard	100.024.524
PubChem CID	110678;
UNII	S5K2510L3D ;
CompTox Dashboard (EPA)	DTXSID10971212 ;
	InChI InChI=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 Key: NISVZEWKUNUGQQ-UHFFFAOYSA-N ; 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 Key: NISVZEWKUNUGQQ-UHFFFAOYAT;
	SMILES OCC(O)COc1ccc(cc1)C(C)(C)c2ccc(OCC(O)CO)cc2;
Properties
Chemical formula	C21H28O6
Molar mass	376.449 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Bis-HPPP (2,2-bis[4(2,3-hydroxypropoxy)phenyl]propane) is an organic compound that is formed when the dental composite material bis-GMA is degraded by salivary esterases.^[1] It is also called BADGE·2H₂O in reference to it being the hydrolyzed form of BADGE, which is used in the formation of epoxy resins.^[2] Structurally, it is a di-ether of bisphenol A.

Formation

Together with methacrylic acid, bis-HPPP is released following the CE-catalyzed^{[clarification needed]} hydrolysis of 2,2-[4(2-hydroxy 3-methacryloxypropoxy)-phenyl]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 acrylic polymers of dental composites.

Analysis by mass spectrometry demonstrated that hydrolytic reactions would cleave the ester bonds of both methacrylate units in bis-GMA and produce bis-HPPP along with two molecules of methacrylic acid.^[3]

References

^ Shokati, Babak; Tam, Laura Eva; Santerre, J. Paul; Finer, Yoav (2010). "Effect of salivary esterase on the integrity and fracture toughness of the dentin-resin interface". Journal of Biomedical Materials Research Part B: Applied Biomaterials. 94 (1): 230–7. doi:10.1002/jbm.b.31645. PMID 20524199.
^ Yonekubo, Jun; Hayakawa, Kazuichi; Sajiki, Junko (1 March 2008). "Concentrations of Bisphenol A, Bisphenol A Diglycidyl Ether, and Their Derivatives in Canned Foods in Japanese Markets". Journal of Agricultural and Food Chemistry. 56 (6): 2041–2047. doi:10.1021/jf073106n.
^ Finer Y, S.J.; Santerre, JP (2004). "The influence of resin chemistry on a dental composite's biodegradation". J Biomed Mater Res. 69A (2): 233–246. doi:10.1002/jbm.a.30000. PMID 15057996.

[1] Shokati, Babak; Tam, Laura Eva; Santerre, J. Paul; Finer, Yoav (2010). "Effect of salivary esterase on the integrity and fracture toughness of the dentin-resin interface". Journal of Biomedical Materials Research Part B: Applied Biomaterials. 94 (1): 230–7. doi:10.1002/jbm.b.31645. PMID 20524199.

[2] Yonekubo, Jun; Hayakawa, Kazuichi; Sajiki, Junko (1 March 2008). "Concentrations of Bisphenol A, Bisphenol A Diglycidyl Ether, and Their Derivatives in Canned Foods in Japanese Markets". Journal of Agricultural and Food Chemistry. 56 (6): 2041–2047. doi:10.1021/jf073106n.

[3] Finer Y, S.J.; Santerre, JP (2004). "The influence of resin chemistry on a dental composite's biodegradation". J Biomed Mater Res. 69A (2): 233–246. doi:10.1002/jbm.a.30000. PMID 15057996.

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