3-(3,4-dihydroxyphenyl)propanoic acid propyl ester | 90522-64-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-(3,4-dihydroxyphenyl)propanoic acid propyl ester
• 英文别名: propyl dihydrocaffeate；propyl hydrocaffeate；3-(3,4-dihydroxy-phenyl)-propionic acid propyl ester；3-(3,4-Dihydroxy-phenyl)-propionsaeure-propylester；n-Propyl dihydrocaffeate；propyl 3-(3,4-dihydroxyphenyl)propanoate
• CAS: 90522-64-8
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: KSVFKVOUIYWQBG-UHFFFAOYSA-N

物化性质

• 沸点：
  371.8±27.0 °C(Predicted)
• 密度：
  1.188±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对羟基苯丙酸 在 三甲基氯硅烷 、 Agaricus bisporus tyrosinase immobilized on polydiallyldimethyl ammonium chloride functionalized oxidized multi-walled carbonanotubes 、 氧气 作用下， 以 aq. phosphate buffer 、 二氯甲烷 为溶剂， 反应 48.08h， 生成 3-(3,4-dihydroxyphenyl)propanoic acid propyl ester
  参考文献：
  名称：

  Carbon nanotubes supported tyrosinase in the synthesis of lipophilic hydroxytyrosol and dihydrocaffeoyl catechols with antiviral activity against DNA and RNA viruses

  摘要：

  Hydroxytyrosol and dihydrocaffeoyl catechols with lipophilic properties have been synthesized in high yield using tyrosinase immobilized on multi-walled carbon nanotubes by the Layer-by-Layer technique. All synthesized catechols were evaluated against a large panel of DNA and RNA viruses, including Poliovirus type 1, Echovirus type 9, Herpes simplex virus type 1 (HSV-1), Herpes simplex virus type 2 (HSV-2), Coxsackievirus type B3 (Cox B3), Adenovirus type 2 and type 5 and Cytomegalovirus (CMV). A significant antiviral activity was observed in the inhibition of HSV-1, HSV-2, Cox B3 and CMV. The mechanism of action of the most active dihydrocaffeoyl derivative was investigated against a model of HSV-1 infection. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.07.061

文献信息

• Tyrosinase and Layer-by-Layer supported tyrosinases in the synthesis of lipophilic catechols with antiinfluenza activity
  作者：Tiziana Bozzini、Giorgia Botta、Michela Delfino、Silvano Onofri、Raffaele Saladino、Donatella Amatore、Rossella Sgarbanti、Lucia Nencioni、Anna Teresa Palamara

  DOI：10.1016/j.bmc.2013.10.026

  日期：2013.12

  Catechol derivatives with lipophilic properties have been selectively synthesized by tyrosinase in high yield avoiding long and tedious protection/deprotection steps usually required in traditional procedures. The synthesis was effective also with immobilized tyrosinase able to perform for more runs. The novel catechols were evaluated against influenza A virus, that continue to represent a severe threat worldwide. A significant antiviral activity was observed in derivatives characterized by antioxidant activity and long carbon alkyl side-chains, suggesting the possibility of a new inhibition mechanism based on both redox and lipophilic properties. (C) 2013 Elsevier Ltd. All rights reserved.
• Tamura et al., Nippon Nogeikagaku Kaishi, 1952, vol. 26, p. 413
  作者：Tamura et al.

  DOI：——

  日期：——
• Carbon nanotubes supported tyrosinase in the synthesis of lipophilic hydroxytyrosol and dihydrocaffeoyl catechols with antiviral activity against DNA and RNA viruses
  作者：Giorgia Botta、Bruno Mattia Bizzarri、Adriana Garozzo、Rossella Timpanaro、Benedetta Bisignano、Donatella Amatore、Anna Teresa Palamara、Lucia Nencioni、Raffaele Saladino

  DOI：10.1016/j.bmc.2015.07.061

  日期：2015.9

  Hydroxytyrosol and dihydrocaffeoyl catechols with lipophilic properties have been synthesized in high yield using tyrosinase immobilized on multi-walled carbon nanotubes by the Layer-by-Layer technique. All synthesized catechols were evaluated against a large panel of DNA and RNA viruses, including Poliovirus type 1, Echovirus type 9, Herpes simplex virus type 1 (HSV-1), Herpes simplex virus type 2 (HSV-2), Coxsackievirus type B3 (Cox B3), Adenovirus type 2 and type 5 and Cytomegalovirus (CMV). A significant antiviral activity was observed in the inhibition of HSV-1, HSV-2, Cox B3 and CMV. The mechanism of action of the most active dihydrocaffeoyl derivative was investigated against a model of HSV-1 infection. (C) 2015 Elsevier Ltd. All rights reserved.