Bis-HPPP

2,2-Bis[4(2,3-hydroxypropoxy)phenyl]propane (bis-HPPP) is an organic compound that is formed when the dental composite material bis-GMA is degraded by salivary esterases.[1] It is structurally related to bisphenol A.

Bis-HPPP
Names
IUPAC name
2,2-bis[4-(2,3-hydroxypropoxy)phenyl]propane
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.024.524
UNII
Properties
C21H28O6
Molar mass 376.44 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Formation

Together with methacrylic acid, bis-HPPP is released following the CE-catalyzed 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.[2]

References

  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. 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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