Dinitrobisphenol A

3,3'-Dinitrobisphenol A is an organic compound with the formula (HO(O2N)C6H3)2C(CH3)2. It is a yellow-orange solid prepared by nitration of bisphenol A[1][2]

Dinitrobisphenol A
Names
Preferred IUPAC name
4,4′-(Propane-2,2-diyl)bis(2-nitrophenol)
Other names
3,3'-Dinitro-bisphenol A; Dinitro-bisphenol A; 2,2-Bis(4-hydroxy-3-nitrophenyl)propane; 4-[2-(4-Hydroxy-3-nitrophenyl)propan-2-yl]-2-nitrophenol
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • CC(C)(C1=CC(=C(C=C1)O)[N+](=O)[O-])C2=CC(=C(C=C2)O)[N+](=O)[O-]
Properties
C15H14N2O6
Molar mass 318.285 g·mol−1
Appearance Yellow powder
Melting point 130 °C (266 °F; 403 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Carcinogenicity

It has been proposed that dinitrobisphenol A might be formed in vivo by peroxynitrite mediated oxidations of bisphenol A and that it may exhibit higher toxicity than BPA itself.[3] 3,3'-Dinitrobisphenol A is found to be genotoxic in male ICR mice on a micronucleus test.[4] Its estrogenic potential is not known however it has shown some binding to estrogen-related receptor gamma to an extent.[5]

See also

References
  1. Sulzberg, Theodore; Cotter, Robert J. (1969). "Synthesis and polymerization of a dinitrobisphenol a: A new polycarbonate synthesis". Journal of Polymer Science Part B: Polymer Letters. 7 (3): 185. Bibcode:1969JPoSL...7..185S. doi:10.1002/pol.1969.110070303.
  2. Babu, Sainath; Pathak, Chintan; Uppu, Satvika; Jones, Conrad; Fronczek, Frank R.; Uppu, Rao M. (2011). "3,3′-Dinitrobisphenol A". Acta Crystallographica Section E. 67 (10): o2556. doi:10.1107/S1600536811035458. PMC 3201564. PMID 22065402.
  3. Masuda, Shuichi; Terashima, Yumeko; Sano, Ayako; Kuruto, Ryoko; Sugiyama, Yasumasa; Shimoi, Kayoko; Tanji, Kenichi; Yoshioka, Hisashi; Terao, Yoshiyasu; Kinae, Naohide (August 2005). "Changes in the mutagenic and estrogenic activities of bisphenol A upon treatment with nitrite". Mutation Research/Genetic Toxicology and Environmental Mutagenesis. 585 (1–2): 137–146. doi:10.1016/j.mrgentox.2005.04.005.
  4. Toyoizumi, Tomoyasu; Deguchi, Yuya; Masuda, Shuichi; Kinae, Naohide (2014). "Genotoxicity and Estrogenic Activity of 3,3′-Dinitrobisphenol a in Goldfish". Bioscience, Biotechnology, and Biochemistry. 72 (8): 2118. doi:10.1271/bbb.80193.
  5. Babu, Sainath; Vellore, Nadeem A.; Kasibotla, Agasthya V.; Dwayne, Harlan J.; Stubblefield, Michael A.; Uppu, Rao M. (2012). "Molecular docking of bisphenol a and its nitrated and chlorinated metabolites onto human estrogen-related receptor-gamma". Biochemical and Biophysical Research Communications. 426 (2): 215. doi:10.1016/j.bbrc.2012.08.065. PMID 22935422.
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