2-(4-hydroxy-3-methoxyphenyl)ethyl methyl carbonate | 953422-35-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(4-hydroxy-3-methoxyphenyl)ethyl methyl carbonate
• CAS: 953422-35-0
• 化学式: C₁₁H₁₄O₅
• 分子量: 226.229
• InChiKey: FIBSENSLMUPUCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(4-hydroxy-3-methoxyphenyl)ethyl methyl carbonate 在 polymer-supported IBX 作用下， 以 dimethyl carbonate 为溶剂， 生成 2-(3',4'-二羟基苯基)乙基甲基碳酸酯
  参考文献：
  名称：

  A novel use of the recyclable polymer-supported IBX: an efficient chemoselective and regioselective oxidation of phenolic compounds. The case of hydroxytyrosol derivatives.

  摘要：

  A useful and novel application of polymer-supported IBX for the chemoselective and regioselective oxidation of phenolic compounds has been described. Hydroxytyrosol and carboxymethylated hydroxytyrosol have been prepared in good conversions and yields under green chemistry conditions in the presence of dimethyl carbonate as the solvent. Polymer supported reagent has been recovered by simple filtration, regenerated and reused for more cycles of oxidation reactions without loss of efficiency. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.037
• 作为产物：
  描述：

  对羟基苯乙醇 在 N-溴代丁二酰亚胺(NBS) 、 sodium methylate 、 copper(I) bromide 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 2-(4-hydroxy-3-methoxyphenyl)ethyl methyl carbonate 、 4-羟基-3-甲氧基苯乙醇
  参考文献：
  名称：

  Antioxidant and Biological Activities of Hydroxytyrosol and Homovanillic Alcohol Obtained from Olive Mill Wastewaters of Extra-Virgin Olive Oil Production

  摘要：

  Some constituents of the Mediterranean diet, such as extra-virgin olive oil (EVOO) contain substances such as hydroxytyrosol (HT) and its metabolite homovanillic alcohol (HA). HT has aroused much interest due to its antioxidant activity as a radical scavenger, whereas only a few studies have been made on the HA molecule. Both chemical synthesis and extraction techniques have been developed to obtain these molecules, with each method having its advantages and drawbacks. In this study, we report the use of tyrosol from olive mill wastewaters as a starting molecule to synthesize HT and HA, using a sustainable procedure characterized by high efficiency and low cost. The effects of HT and HA were evaluated on two cell lines, THP-1 human leukemic monocytes and L-6 myoblasts from rat skeletal muscle, after treating the cells with a radical generator. Both HT and HA efficiently inhibited ROS production. In particular, HT inhibited the proliferation of the THP-1 leukemic monocytes, while HA protected L-6 myoblasts from cytotoxicity.

  DOI：

  10.1021/acs.jafc.0c05230

文献信息

• Convenient Synthesis of Hydroxytyrosol and Its Lipophilic Derivatives from Tyrosol or Homovanillyl Alcohol
  作者：Roberta Bernini、Enrico Mincione、Maurizio Barontini、Fernanda Crisante

  DOI：10.1021/jf801558z

  日期：2008.10.8

  chemoselective protection of the alcoholic group of these compounds was performed by using dimethyl carbonate (DMC) as reagent/solvent; second, the oxidation with 2-iodoxybenzoic acid (IBX) or Dess-Martin periodinane reagent (DMP) and in situ reduction with sodium dithionite (Na2S2O4) allowed the preparation of carboxymethylated hydroxytyrosol; finally, by a mild hydrolytic step, hydroxytyrosol was

  羟基酪醇是一种天然存在的具有抗氧化性能的邻酚类化合物，它是通过三步高产率程序从天然和低成本的化合物（例如酪醇或高香草醇）合成的。首先，通过使用碳酸二甲酯（DMC）作为试剂/溶剂，对这些化合物的醇基进行有效的化学选择性保护。其次，用2-碘氧基苯甲酸（IBX）或Dess-Martin高碘烷试剂（DMP）氧化并用连二亚硫酸钠（Na 2 S 2 O 4）原位还原，可以制备羧甲基化羟基酪醇。最终，通过温和的水解步骤，以高收率和高纯度获得了羟基酪醇，这已通过NMR光谱和HPLC谱图得到了证实。通过类似的方法，亲脂性羟基酪醇衍生物被用作药物，食品，和化妆品制剂，都准备好了。实际上，首先，通过使用酰氯在没有任何催化剂的情况下对酪醇和高香草醇的醇基团进行化学选择性保护，以获得相应的亲脂性衍生物，然后将这些化合物以高收率和高纯度转化为羟基酪醇衍生物。 IBX或DMP和Na2S2O4的氧化/还原途径。
• Chemoselective and efficient carbomethoxylation of the alcoholic chain of phenols by dimethyl carbonate (DMC)
  作者：Roberta Bernini、Enrico Mincione、Fernanda Crisante、Maurizio Barontini、Giancarlo Fabrizi、Patrizia Gentili

  DOI：10.1016/j.tetlet.2007.07.109

  日期：2007.9

  The efficiency of dimethyl carbonate (DMC) as chemoselective carbomethoxylating agent of the alcoholic chain of phenols has been investigated. In the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or sulfuric acid as catalysts, new carbomethoxylated phenolic compounds were obtained in quantitative yields. A new efficient derivatization of the aliphatic alcoholic chain of the precious natural hydroxytyrosol is described, which increases the lipophilicity of the hydroxytyrosol. The antioxidant activity of this new carboxymethylated hydroxytyrosol 8 has been investigated using DPPH radical scavenging test. The results showed that this new compound has an antioxidant activity similar to hydroxytyrosol. (c) 2007 Elsevier Ltd. All rights reserved.
• A novel use of the recyclable polymer-supported IBX: an efficient chemoselective and regioselective oxidation of phenolic compounds. The case of hydroxytyrosol derivatives.
  作者：Roberta Bernini、Enrico Mincione、Fernanda Crisante、Maurizio Barontini、Giancarlo Fabrizi

  DOI：10.1016/j.tetlet.2009.01.037

  日期：2009.3

  A useful and novel application of polymer-supported IBX for the chemoselective and regioselective oxidation of phenolic compounds has been described. Hydroxytyrosol and carboxymethylated hydroxytyrosol have been prepared in good conversions and yields under green chemistry conditions in the presence of dimethyl carbonate as the solvent. Polymer supported reagent has been recovered by simple filtration, regenerated and reused for more cycles of oxidation reactions without loss of efficiency. (C) 2009 Elsevier Ltd. All rights reserved.
• Antioxidant and Biological Activities of Hydroxytyrosol and Homovanillic Alcohol Obtained from Olive Mill Wastewaters of Extra-Virgin Olive Oil Production
  作者：Alessandra Ricelli、Fabio Gionfra、Zulema Percario、Martina De Angelis、Ludovica Primitivo、Veronica Bonfantini、Roberto Antonioletti、Simonetta Maria Bullitta、Luciano Saso、Sandra Incerpi、Jens Zacho Pedersen

  DOI：10.1021/acs.jafc.0c05230

  日期：2020.12.30

  Some constituents of the Mediterranean diet, such as extra-virgin olive oil (EVOO) contain substances such as hydroxytyrosol (HT) and its metabolite homovanillic alcohol (HA). HT has aroused much interest due to its antioxidant activity as a radical scavenger, whereas only a few studies have been made on the HA molecule. Both chemical synthesis and extraction techniques have been developed to obtain these molecules, with each method having its advantages and drawbacks. In this study, we report the use of tyrosol from olive mill wastewaters as a starting molecule to synthesize HT and HA, using a sustainable procedure characterized by high efficiency and low cost. The effects of HT and HA were evaluated on two cell lines, THP-1 human leukemic monocytes and L-6 myoblasts from rat skeletal muscle, after treating the cells with a radical generator. Both HT and HA efficiently inhibited ROS production. In particular, HT inhibited the proliferation of the THP-1 leukemic monocytes, while HA protected L-6 myoblasts from cytotoxicity.