ethyl 3-(3,4,5-trihydroxyphenyl)-2-propenoate | 709007-51-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl 3-(3,4,5-trihydroxyphenyl)-2-propenoate
• 英文别名: ethyl trans-3-(3,4,5-trihydroxyphenyl)-2-propenoate；ethyl trans-3,4,5-trihdyroycinnamate；ethyl 3,4,5-trihydroxycinnamate；3,4,5-trihydroxy-trans-cinnamic acid ethyl ester；3,4,5-Trihydroxy-trans-zimtsaeure-aethylester；ethyl (E)-3-(3,4,5-trihydroxyphenyl)prop-2-enoate
• CAS: 709007-51-2
• 化学式: C₁₁H₁₂O₅
• 分子量: 224.213
• InChiKey: IBBPTXFHLRTGAW-ONEGZZNKSA-N

物化性质

• 熔点：
  170 °C
• 沸点：
  444.0±45.0 °C(Predicted)
• 密度：
  1.382±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  ethyl 3-(3,4,5-trihydroxyphenyl)-2-propenoate 、 原甲酸三乙酯 在 Amberlyst 15-E 作用下， 以 苯 为溶剂， 以98%的产率得到ethyl 3-hydroxy-4,5-(ethoxymethylenedioxy)cinnamate
  参考文献：
  名称：

  Straightforward Total Synthesis of 2-O-Feruloyl-l-malate, 2-O-Sinapoyl-l-malate and 2-O-5-Hydroxyferuloyl-l-malate

  摘要：

  本发明介绍了一种利用 Steglich 酯化法分别从苹果酸和阿魏酸、山奈酸和羟基阿魏酸制备 2-O-阿魏酰-l-苹果酸、2-O-山奈酰-l-苹果酸和 2-O-5-羟基阿魏酰-l-苹果酸的合成方法。

  DOI：

  10.1055/s-0029-1216983
• 作为产物：
  描述：

  3,4,5-三乙酰氧基苯甲醛 在 吡啶 、 氯仿 、 sodium methylate 、 苯胺 作用下， 生成 ethyl 3-(3,4,5-trihydroxyphenyl)-2-propenoate
  参考文献：
  名称：

  Freudenberg; Huebner, Chemische Berichte, 1952, vol. 85, p. 1181,1188

  摘要：

  DOI：

文献信息

• Antioxidant Versus Cytotoxic Properties of Hydroxycinnamic Acid Derivatives – A New Paradigm in Phenolic Research
  作者：Mário Esteves、Christophe Siquet、Alexandra Gaspar、Vitor Rio、Joana B. Sousa、Salette Reis、Maria P. M. Marques、Fernanda Borges

  DOI：10.1002/ardp.200700168

  日期：2008.3

  trihydroxycinnamic derivatives correlate well both with their structural characteristics and with their antioxidant/cytotoxic activities. A positive structure‐activity‐property relationship between cytotoxic and antioxidant activities, which is intrinsically related with physico‐chemical and conformational properties, is anticipated, as a noteworthy study that must be done for phenolic systems. As damage

  合成了三羟基肉桂衍生物并评估了它们的抗氧化和细胞毒活性。当脂质体用作目标系统时，酯衍生物表现出更高的自由基清除活性，这一事实可能与其亲脂性和构象偏好有关。发现这些化合物对人子宫颈腺癌细胞系 (HeLa) 显示出显着的生长抑制和细胞毒性作用。目前获得的三羟基肉桂酸衍生物的分配系数与其结构特征和抗氧化/细胞毒活性密切相关。预计细胞毒性和抗氧化活性之间存在正构-活性-特性关系，这与物理化学和构象特性具有内在相关性，作为一项值得注意的研究，必须对酚醛系统进行。由于损伤事件经常与氧化应激相关，单一化合物中两种特性的普遍存在可能有益于预防或治疗目的。
• Conformational analysis of a trihydroxylated derivative of cinnamic acid—a combined Raman spectroscopy and Ab initio study
  作者：S.M. Fiuza、E. Van Besien、N. Milhazes、F. Borges、M.P.M. Marques

  DOI：10.1016/j.molstruc.2004.02.019

  日期：2004.5

  A conformational analysis of 3-(3,4,5-trihydroxyphenyl)-2-propenoic acid (3,4,5-trihydroxycinnamic acid, THPPE), a trihydroxylated cinnamic acid analogous to caffeic acid (a natural compound often present in diet), was carried out by Raman spectroscopy coupled to Ab initio MO calculations. Apart from the optimised geometrical parameters for the most stable conformers of this compound, and for one of its dimeric species, the corresponding harmonic vibrational frequencies, as well as potential-energy profiles for rotation around several bonds within the molecule, were obtained. Twenty one distinct conformers were found for THPPE, the lowest energy ones-THPPE 1 and THPPE 2-displaying a completely planar geometry. The conformational preferences of this system were thus found to be mainly ruled by the stabilising effect of pi-electron delocalisation. At the light of these results, a complete assignment of the corresponding solid state Raman spectra was performed. (C) 2004 Elsevier B.V. All rights reserved.
• Exploring nature profits: Development of novel and potent lipophilic antioxidants based on galloyl–cinnamic hybrids
  作者：José Teixeira、Tiago Silva、Sofia Benfeito、Alexandra Gaspar、E. Manuela Garrido、Jorge Garrido、Fernanda Borges

  DOI：10.1016/j.ejmech.2012.12.049

  日期：2013.4

  Phenolic acids are ubiquitous antioxidants accounting for approximately one third of the phenolic compounds in our diet. Their importance was supported by epidemiological studies that suggest an inverse relationship between dietary intake of phenolic antioxidants and the occurrence of diseases, such as cancer and neurodegenerative disorders. However, until now, most of natural antioxidants have limited therapeutic success a fact that could be related with their limited distribution throughout the body and with the inherent difficulties to attain the target sites.The development of phenolic antioxidants based on a hybrid concept and structurally based on natural hydroxybenzoic (gallic acid) and hydroxycinnamic (caffeic acid) scaffolds seems to be a suitable solution to surpass the mentioned drawbacks. Galloyl cinnamic hybrids were synthesized and their antioxidant activity as well as partition coefficients and redox potentials evaluated. The structure property activity relationship (SPAR) study revealed the existence of a correlation between the redox potentials and antioxidant activity. The galloyl cinnamic acid hybrid stands out as the best antioxidant supplementing the effect of a blend of gallic acid plus caffeic acid endorsing the hypothesis that the whole is greater than the sum of the parts. In addition, some hybrid compounds possess an appropriate lipophilicity allowing their application as chain-breaking antioxidant in biomembranes or other type of lipidic systems. Their predicted ADME properties are also in accordance with the general requirements for drug-like compounds. Accordingly, these phenolic hybrids can be seen as potential antioxidants for tackling the oxidative status linked to the neurodegenerative, inflammatory or cancer processes. (C) 2013 Elsevier Masson SAS. All rights reserved.