4-[(4-acryloyloxyphenyl)azo]benzoic acid | 185101-97-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 4-[(4-acryloyloxyphenyl)azo]benzoic acid
• 英文别名: 4-{(E)-[4-(Acryloyloxy)phenyl]diazenyl}benzoic acid；4-[(4-prop-2-enoyloxyphenyl)diazenyl]benzoic acid
• CAS: 185101-97-7
• 化学式: C₁₆H₁₂N₂O₄
• 分子量: 296.282
• InChiKey: YCGSXXYWIBUNNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  88.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  丙烯酰氯 、 4-(4-羟基苯偶氮基)苯甲酸 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 50.0h， 生成 4-[(4-acryloyloxyphenyl)azo]benzoic acid
  参考文献：
  名称：

  Multiresponsive Hydrogels Based on Xylan-Type Hemicelluloses and Photoisomerized Azobenzene Copolymer as Drug Delivery Carrier

  摘要：

  Stimulus-responsive hydrogels, which can undergo significant physicochemical changes in response to various physical or chemical stimuli, have drawn wide attention in many fields. In this study, novel photoresponsive hydrogels prepared by free radical copolymerization of xylan-type hemicellulose methacrylate with 4-[(4-acryloyloxyphenyl)azo]benzoic acid (AOPAB) were investigated, which showed multiresponsive behaviors to pH, water/ethanol alternating solutions, and light. The swelling ratios of the prepared hydrogels in distilled water decreased from 9.8 to 2.2 g/g with AOPAB content increase from 2% to 16%. The hydrogel displayed rapid swelling and deswelling performance in water and ethanol alternating solutions. Additionally, under UV irradiation the trans-conformation of azobenzene in the hydrogel would generally convert into the cis-conformation and resulted in the hydrophilic/hydrophobic balance variation of the hydrogel. Therefore, the hydrogel loaded with vitamin B-12 (VB12) showed a higher drug cumulative release rate under UV irradiation than that without UV irradiation.

  DOI：

  10.1021/jf504040s

文献信息

• Multiresponsive Hydrogels Based on Xylan-Type Hemicelluloses and Photoisomerized Azobenzene Copolymer as Drug Delivery Carrier
  作者：Xuefei Cao、Xinwen Peng、Linxin Zhong、Runcang Sun

  DOI：10.1021/jf504040s

  日期：2014.10.15

  Stimulus-responsive hydrogels, which can undergo significant physicochemical changes in response to various physical or chemical stimuli, have drawn wide attention in many fields. In this study, novel photoresponsive hydrogels prepared by free radical copolymerization of xylan-type hemicellulose methacrylate with 4-[(4-acryloyloxyphenyl)azo]benzoic acid (AOPAB) were investigated, which showed multiresponsive behaviors to pH, water/ethanol alternating solutions, and light. The swelling ratios of the prepared hydrogels in distilled water decreased from 9.8 to 2.2 g/g with AOPAB content increase from 2% to 16%. The hydrogel displayed rapid swelling and deswelling performance in water and ethanol alternating solutions. Additionally, under UV irradiation the trans-conformation of azobenzene in the hydrogel would generally convert into the cis-conformation and resulted in the hydrophilic/hydrophobic balance variation of the hydrogel. Therefore, the hydrogel loaded with vitamin B-12 (VB12) showed a higher drug cumulative release rate under UV irradiation than that without UV irradiation.