3-nitro bisphenol A | 233756-97-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-nitro bisphenol A
• 英文别名: 2-nitrobisphenol A；4-[2-(4-Hydroxyphenyl)propan-2-yl]-2-nitrophenol
• CAS: 233756-97-3
• 化学式: C₁₅H₁₅NO₄
• 分子量: 273.288
• InChiKey: CWBGCGMRACNKDP-UHFFFAOYSA-N

物化性质

• 沸点：
  420.9±35.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  86.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  双酚A 在 1-甲基咪唑硫酸盐 、 sodium nitrate 作用下， 以 乙腈 为溶剂， 生成 3-nitro bisphenol A
  参考文献：
  名称：

  Molecular docking of bisphenol A and its nitrated and chlorinated metabolites onto human estrogen-related receptor-gamma

  摘要：

  A xenoestrogen and known endocrine disruptor, bisphenol A (BPA) binds the human estrogen-related receptor-gamma (ERR gamma) with high affinity (Kd approximate to 5.5 nM). It is likely that BPA undergoes oxidative biotransformation by hypochlorite/hypochlorous acid (-OCl/HOCl) and peroxynitrite (PN) and the products formed in these reactions may serve as secondary estrogens and contribute to the toxicodynamics of BPA. Therefore, in the present study we have examined the formation of chlorinated and nitrated BPA in reactions of BPA with -OCl/HOCl and PN(+CO2) performed around the neutral pH. We have identified four major products in these reactions and they include 3-chloro-BPA (CBPA), 3,3'-dichloro-BPA (DCBPA), 3-nitro-BPA (NBPA) and 3,3'-dinitro-BPA (DNBPA). Towards understanding the toxicodynamics and estrogenic activity of BPA in biological systems, we have performed molecular docking of BPA, CBPA, DCBPA, DNBPA and NBPA onto the ERR gamma using AutoDock 4.2 software and compared the binding energies with those of estradiol, the natural ligand. Based on the genetic algorithm, the three best conformations were selected and averaged for each ligand and a detailed analysis of molecular interactions based on free energies of binding (kcal/mol) was computed. The results indicate the following rank order of binding to ERR gamma: BPA (-8.78 +/- 0.06) > CBPA (-8.53 +/- 0.41) > NBPA (-7.36 +/- 0.74) > DCBPA (-5.24 +/- 0.17) > DNBPA (-4.95 +/- 0.78) > estradiol (-4.94 +/- 1.04). The docking studies revealed that the OH group of one of the phenyl rings forms a hydrogen bond with Glu275/Arg316, while the OH group of other phenyl ring was bound to Asp346. These results suggest that both BPA and its putative chlorinated and nitrated metabolites have strong binding affinity compared to estradiol. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bbrc.2012.08.065

文献信息

• Melamine-(H2SO4)3 and PVP-(H2SO4)n as solid acids: Synthesis and application in the first mono- and di-nitration of bisphenol A and other phenols
  作者：Gholamabbas Chehardoli、Mohammad Ali Zolfigol、Seyedeh Bahareh Azimi、Ebadollah Alizadeh

  DOI：10.1016/j.cclet.2011.01.021

  日期：2011.7

  Melamine and poly vinylpyrrolidone (PVP) reacted with neat sulfuric acid readily to form two new organic solid acids namely melamine-(H2SO4)(3) and PVP-(H2SO4)(n). These solid acids were used for the first nitration of bisphenol A as well as other phenols in the presence of NH4NO3. Mono- and di-nitro bisphenol A have been characterized with IR and H-1 NMR techniques. (C) 2011 Chehardoli Gholamabbas. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.