benzyl 3,4,5-trihydroxybenzoate | 50888-96-5

• 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: benzyl 3,4,5-trihydroxybenzoate
• 英文别名: benzyl gallate；Gallic Acid Benzyl Ester
• CAS: 50888-96-5
• 化学式: C₁₄H₁₂O₅
• 分子量: 260.246
• InChiKey: HPCCQNGKAFBWAU-UHFFFAOYSA-N

物化性质

• 熔点：
  90-90.5 °C
• 沸点：
  528.3±45.0 °C(Predicted)
• 密度：
  1.419±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于丙酮（少量）。DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl 3,4,5-trihydroxybenzoate 在 邻四氯苯醌 、 potassium carbonate 、 溶剂黄146 、 potassium iodide 作用下， 以 四氢呋喃 、 乙醚 、 水 、 丙酮 、 乙腈 为溶剂， 反应 46.0h， 生成 benzyl 5-(benzyloxy)-2-(S-cysteinyl)-3,4-dihydroxybenzoate
  参考文献：
  名称：

  Galloyl-Derived Orthoquinones as Reactive Partners in Nucleophilic Additions and Diels−Alder Dimerizations:  A Novel Route to the Dehydrodigalloyl Linker Unit of Agrimoniin-Type Ellagitannins

  摘要：

  Orthochloranil-mediated oxidation of galloyl monoethers furnishes the derived orthoquinones in excellent yield. These reactive electrophiles participate in a variety of nucleophilic addition reactions with heteroatomic and carbanionic partners. In addition, Lewis acid-mediated dimerization of the orthoquinones provides an efficient route to dehydrodigalloyl-type diaryl ether units characteristic of several ellagitannin natural products. The implications for ellagitannin biosynthesis and gallotannin-protein covalent attachment are discussed.

  DOI：

  10.1021/jo961043u
• 作为产物：
  描述：

  三乙酰基没食子酰氯 在 4-二甲氨基吡啶 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 5.5h， 生成 benzyl 3,4,5-trihydroxybenzoate
  参考文献：
  名称：

  Galloyl-Derived Orthoquinones as Reactive Partners in Nucleophilic Additions and Diels−Alder Dimerizations:  A Novel Route to the Dehydrodigalloyl Linker Unit of Agrimoniin-Type Ellagitannins

  摘要：

  Orthochloranil-mediated oxidation of galloyl monoethers furnishes the derived orthoquinones in excellent yield. These reactive electrophiles participate in a variety of nucleophilic addition reactions with heteroatomic and carbanionic partners. In addition, Lewis acid-mediated dimerization of the orthoquinones provides an efficient route to dehydrodigalloyl-type diaryl ether units characteristic of several ellagitannin natural products. The implications for ellagitannin biosynthesis and gallotannin-protein covalent attachment are discussed.

  DOI：

  10.1021/jo961043u

文献信息

• Synthesis and evaluation of gallocyanine dyes as potential agents for the treatment of Alzheimer's disease and related neurodegenerative tauopathies
  作者：Spyros Mpousis、Savvas Thysiadis、Nicolaos Avramidis、Sotirios Katsamakas、Spiros Efthimiopoulos、Vasiliki Sarli

  DOI：10.1016/j.ejmech.2015.11.024

  日期：2016.1

  In search of safe and effective anti-Alzheimer disease agents a series of gallocyanine dyes have been synthesized and evaluated for their ability to inhibit LRPs/DKK1 interactions. Modulation of the interactions between LRPS and DKK1, regulate Wnt signaling pathway and affect Tau phosphorylation. The current efforts resulted in the identification of potent DKK1 inhibitors which are able to inhibit

  为了寻找安全有效的抗阿尔茨海默氏病病原体，已合成了一系列没食子花青染料，并对其抑制LRP / DKK1相互作用的能力进行了评估。LRP S和DKK1之间的相互作用的调节，调节Wnt信号通路并影响Tau磷酸化。当前的努力导致鉴定出有效的DKK1抑制剂，该抑制剂能够抑制前列腺素J2诱导的丝氨酸396的tau磷酸化。
• Chemoselective Esterification of Phenolic Acids in the Presence of Sodium Bicarbonate in Ionic Liquids
  作者：Ambika、Pradeep Pratap Singh、S. M. S. Chauhan

  DOI：10.1080/00397910701845480

  日期：2008.2.1

  Abstract Chemoselective esterification of phenolic acids with dialkyl sulphates or alkyl halides in the presence of sodium bicarbonate in 1,3‐dialkylimidazolium ionic liquids is reported in excellent yields and less reaction time as compared to organic solvents.

  摘要 与有机溶剂相比，在 1,3-二烷基咪唑鎓离子液体中，在碳酸氢钠存在下，酚酸与硫酸二烷基酯或烷基卤化物的化学选择性酯化反应收率高，反应时间更短。
• Design, Synthesis, and Antifungal Activity of Alkyl Gallates Against Plant Pathogenic Fungi In Vitro and In Vivo
  作者：Xiao-Long Zhao、Chun-Qing Li、Xiao-Mei Song、Shuang-Mei Yan、Du-Qiang Luo

  DOI：10.1007/s10600-021-03276-3

  日期：2021.1

  A series of alkyl gallates was synthesized by reacting gallic acid with the corresponding alcohols. Their structures were determined on the basis of spectroscopic data, including NMR and MS. The antifungal activities of these compounds against plant pathogenic fungi in vitro and in vivo were assessed.

  通过没食子酸与相应的醇反应，合成了一系列没食子酸烷基酯。根据 NMR 和 MS 等光谱数据确定了这些化合物的结构。评估了这些化合物在体外和体内对植物病原真菌的抗真菌活性。
• Self-Sorting and Coassembly of Fluorinated, Hydrogenated, and Hybrid Janus Dendrimers into Dendrimersomes
  作者：Qi Xiao、Jack D. Rubien、Zhichun Wang、Ellen H. Reed、Daniel A. Hammer、Dipankar Sahoo、Paul A. Heiney、Srujana S. Yadavalli、Mark Goulian、Samantha E. Wilner、Tobias Baumgart、Sergei A. Vinogradov、Michael L. Klein、Virgil Percec

  DOI：10.1021/jacs.6b08069

  日期：2016.9.28

  simple injection from ethanol solution into water or buffer. Since RF and RH dendrons are not miscible, RF-NBD and RH-RhB were employed to investigate by fluorescence microscopy the self-sorting and coassembly of RF and RH as well as of phospholipids into hybrid DSs mediated by the hybrid hydrogenated-fluorinated RHF Janus dendrimer. The hybrid RHF Janus dendrimer coassembled with both RF and RH. Three-component

  报告了包含七个自组装两亲 Janus 树枝状聚合物的库的模块化合成。其中三个分子在其疏水部分 (RF) 中含有环保的手性-外消旋氟化树突，一个包含非手性氢化树突​​ (RH)，而一种称为混合 Janus 树枝状大分子，包含手性-外消旋氟化和非手性氢化树突​​ (RHF) 的组合) 在其疏水部分。两个 Janus 树枝状聚合物包含手性外消旋氟化树枝状分子和与其亲水部分 (RF-NBD) 共轭的绿色荧光染料，或在其亲水部分 (RH-RhB) 中包含非手性氢化和红色荧光染料。这些 RF、RH 和 RHF Janus 树枝状大分子自组装成单层或洋葱状软泡状树枝状体 (DSs)，通过简单地将乙醇溶液注入水或缓冲液中，可以获得与生物膜厚度相似的膜。由于 RF 和 RH 树突不混溶，RF-NBD 和 RH-RhB 被用于通过荧光显微镜研究 RF 和 RH 以及磷脂的自分选和共组装成混合 DSs 由混合氢化氟化
• Erectile Dysfunction Treatment
  申请人：——

  公开号：US20040247698A1

  公开（公告）日：2004-12-09

  A method for extracting compositions from a natural product, their pharmaceutical compositions, the pharmaceutical compounds, and their therapeutic uses as a sexual performance enhancer, in the treatment of erectile dysfunction, and in the treatment of hypertension in humans and animals.

  一种从天然产物中提取化合物的方法，以及它们的制药组合物、制药化合物，以及它们作为性能增强剂的治疗用途，用于治疗人类和动物的勃起功能障碍和高血压。