4-(乙酰氧基)-3-甲氧基苯并烯乙醇乙酸酯 | 32022-28-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 4-(乙酰氧基)-3-甲氧基苯并烯乙醇乙酸酯
• 中文别名: 4-乙酰氧基-3-甲氧基苯乙醇乙酸酯
• 英文名称: 4-(2-acetoxyethyl)-2-methoxy-1-acetoxy-benzene
• 英文别名: 4,β-di-O-acetyl-3-methoxytyrosol；4-acetoxy-3-methoxyphenethyl acetate；3-methoxytyrosol diacetate；4-(Acetyloxy)-3-methoxybenzenethanol Acetate；2-(4-acetyloxy-3-methoxyphenyl)ethyl acetate
• CAS: 32022-28-9
• 化学式: C₁₃H₁₆O₅
• 分子量: 252.267
• InChiKey: XKNYEIJAGJNUPM-UHFFFAOYSA-N

物化性质

• 沸点：
  330.2±32.0 °C(Predicted)
• 密度：
  1.144±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(乙酰氧基)-3-甲氧基苯并烯乙醇乙酸酯 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到3,4-二羟基苯乙醇醋酸
  参考文献：
  名称：

  Radical-scavenging polyphenols: new strategies for their synthesis

  摘要：

  讨论了合成多酚的新策略，这些化合物具有抗氧化性质，存在于各种植物中。采用简单和环保的方法接近了不同类别的多酚的合成，包括存在于许多自然系统中的泛醌类多酚，其中涉及电子转移机制，羟基酪醇，是橄榄中酚类分数的主要成分，以及在植物界广泛分布的类黄酮。

  DOI：

  10.1211/jpp.59.12.0013
• 作为产物：
  描述：

  对羟基苯乙醇 在 N-溴代丁二酰亚胺(NBS) 、 sodium methylate 、 溶剂黄146 、 copper(I) bromide 作用下， 以 甲醇 为溶剂， 反应 42.0h， 生成 4-(乙酰氧基)-3-甲氧基苯并烯乙醇乙酸酯
  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

• Tunable microwave-assisted method for the solvent-free and catalyst-free peracetylation of natural products
  作者：Manuela Oliverio、Paola Costanzo、Monica Nardi、Carla Calandruccio、Raffaele Salerno、Antonio Procopio

  DOI：10.3762/bjoc.12.214

  日期：——

  Background: The peracetylation is a simple chemical modification that can be used to enhance the bioavailability of hydrophilic products and to obtain safe and stable pro-drugs.

  Results: A totally green, solvent-free and catalyst-free microwave (MW)-assisted method for peracetylation of natural products such as oleuropein, alpha-hederin, quercetin and rutin is presented. By simply tuning the MW heating program, polyols with chemical diverse –OH groups or thermolabile functionalities can be peracetylated to improve the biological activity without degradation of the natural starting molecules. An evaluation of the process greenness was performed.

  Conclusion: The method is potentially universally applicable for green acetylation of hydrophilic biological molecules, potentially easily scalable for industrial applications, including pharmaceutical, cosmetic and food industry.

  背景：过乙酰化是一种简单的化学修饰方法，可用于增强亲水产品的生物利用度，并获得安全稳定的前药。 结果：提出了一种完全绿色、无溶剂、无催化剂的微波辅助方法，用于过乙酰化天然产物，如欧洲叶酸、α-藤黄素、槲皮素和芦丁。通过简单调节微波加热程序，可以对具有化学多样性的多元醇进行过乙酰化，以提高生物活性，而不会降解天然起始分子。对过程的绿色性进行了评估。 结论：该方法可能普遍适用于绿色乙酰化亲水生物分子，可能易于规模化应用于工业领域，包括制药、化妆品和食品行业。
• Simple and efficient synthesis of benzofuran derivatives from tyrosol
  作者：Paolo Bovicelli、Fabrizio Bottaro、Carla Sappino、Michela Tomei、Valentina Nardi、Ilaria Proietti Silvestri、Beatrice Macchi、Caterina Frezza、Giuliana Righi

  DOI：10.1080/00397911.2015.1133828

  日期：2016.2

  A convenient strategy for the preparation of compounds bearing the benzofuran skeleton starting from tyrosol, a phenol largely present in olive oil production waste, with no biological importance, is reported. A bromination/methoxylation sequence, already described for the synthetic transformation of naturally occurring compounds, was exploited. Depending on the solvent used for the methoxylation reaction together with the presence of a 4-phenol moiety respect to the side chain, benzodihydrofurans or a benzofurans derivative can be obtained.
• Expedient Synthesis of Hydroxytyrosol and its Esters
  作者：Paolo Bovicelli、Roberto Antonioletti、Silvia Mancini、Stefano Causio、Giorgio Borioni、Sergio Ammendola、Maurizio Barontini

  DOI：10.1080/00397910701575509

  日期：2007.12

  An efficient and friendly method for obtaining hydroxytyrosol from tyrosol, a component of olive waste, is reported. Hydroxytyrosol also may be obtained in the form of enzymatically convertible precursors (e.g., hydroxytyrosyl acetate), thus increasing the stability of the active principle.
• 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.
• Radical-scavenging polyphenols: new strategies for their synthesis
  作者：Paolo Bovicelli

  DOI：10.1211/jpp.59.12.0013

  日期：2010.2.18

  New strategies for the synthesis of polyphenols, compounds with antioxidant properties contained in every kind of plants, are discussed. Syntheses of different classes of polyphenols, namely ubiquinones, present in many natural systems in which electron-transfer mechanisms are involved, hydroxy-tyrosol, one of the main components of the phenol fraction in olives, and flavonoids, widespread in the plant kingdom, were approached by simple and environmentally sustainable methods.

  讨论了合成多酚的新策略，这些化合物具有抗氧化性质，存在于各种植物中。采用简单和环保的方法接近了不同类别的多酚的合成，包括存在于许多自然系统中的泛醌类多酚，其中涉及电子转移机制，羟基酪醇，是橄榄中酚类分数的主要成分，以及在植物界广泛分布的类黄酮。