:Dinitrobisphenol A

{{chembox

| PIN= 4,4′-(Propane-2,2-diyl)bis(2-nitrophenol)

| OtherNames= 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

| ImageFile = Dinitrobisphenol A.svg

| Section1= {{Chembox Identifiers

| CASNo= 5329-21-5

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = SUB3DJ24JL

| ChemSpiderID = 190706

| PubChem= 219958

| SMILES = CC(C)(C1=CC(=C(C=C1)O)[N+](=O)[O-])C2=CC(=C(C=C2)O)[N+](=O)[O-]

}}

|Section2= {{Chembox Properties

| C=15|H=14|N=2|O=6

| Appearance= Yellow powder

| Density=

| MeltingPtC= 130

| BoilingPt=

| Solubility=

}}

}}

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{{cite journal | doi =10.1002/pol.1969.110070303| title =Synthesis and polymerization of a dinitrobisphenol a: A new polycarbonate synthesis| journal =Journal of Polymer Science Part B: Polymer Letters| volume =7| issue =3| pages =185| year =1969| last1 =Sulzberg| first1 =Theodore| last2 =Cotter| first2 =Robert J.| bibcode =1969JPoSL...7..185S}}{{cite journal | doi =10.1107/S1600536811035458| title =3,3′-Dinitrobisphenol A| journal =Acta Crystallographica Section E| volume =67| issue =10| pages =o2556| year =2011| last1 =Babu| first1 =Sainath| last2 =Pathak| first2 =Chintan| last3 =Uppu| first3 =Satvika| last4 =Jones| first4 =Conrad| last5 =Fronczek| first5 =Frank R.| last6 =Uppu| first6 =Rao M.| pmc =3201564| pmid=22065402}}

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.{{cite journal |last1=Masuda |first1=Shuichi |last2=Terashima |first2=Yumeko |last3=Sano |first3=Ayako |last4=Kuruto |first4=Ryoko |last5=Sugiyama |first5=Yasumasa |last6=Shimoi |first6=Kayoko |last7=Tanji |first7=Kenichi |last8=Yoshioka |first8=Hisashi |last9=Terao |first9=Yoshiyasu |last10=Kinae |first10=Naohide |title=Changes in the mutagenic and estrogenic activities of bisphenol A upon treatment with nitrite |journal=Mutation Research/Genetic Toxicology and Environmental Mutagenesis |date=August 2005 |volume=585 |issue=1-2 |pages=137–146 |doi=10.1016/j.mrgentox.2005.04.005}} 3,3'-Dinitrobisphenol A is found to be genotoxic in male ICR mice on a micronucleus test.{{cite journal | doi =10.1271/bbb.80193| title =Genotoxicity and Estrogenic Activity of 3,3′-Dinitrobisphenol a in Goldfish| journal =Bioscience, Biotechnology, and Biochemistry| volume =72| issue =8| pages =2118| year =2014| last1 =Toyoizumi| first1 =Tomoyasu| last2 =Deguchi| first2 =Yuya| last3 =Masuda| first3 =Shuichi| last4 =Kinae| first4 =Naohide| doi-access =free}} Its estrogenic potential is not known however it has shown some binding to estrogen-related receptor gamma to an extent.{{cite journal | doi =10.1016/j.bbrc.2012.08.065| pmid =22935422| title =Molecular docking of bisphenol a and its nitrated and chlorinated metabolites onto human estrogen-related receptor-gamma| journal =Biochemical and Biophysical Research Communications| volume =426| issue =2| pages =215| year =2012| last1 =Babu| first1 =Sainath| last2 =Vellore| first2 =Nadeem A.| last3 =Kasibotla| first3 =Agasthya V.| last4 =Dwayne| first4 =Harlan J.| last5 =Stubblefield| first5 =Michael A.| last6 =Uppu| first6 =Rao M.}}

See also

References