(E)-4-hydroxy-3,5-dimethoxycinnamic acid propyl ester

• 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: (E)-4-hydroxy-3,5-dimethoxycinnamic acid propyl ester
• 英文别名: (E)-propyl 3-(4-hydroxy-3,5-dimethoxyphenyl )propenoate；propyl sinapate；propyl (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
• 化学式: C₁₄H₁₈O₅
• 分子量: 266.294
• InChiKey: NNWZNWDZXFTCCH-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  7
• 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

• 作为产物：
  描述：

  3,5-二甲氧基-4-羟基肉桂酸 、 溴丙烷 在 sodium carbonate 、 potassium iodide 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 24.0h， 以68%的产率得到(E)-4-hydroxy-3,5-dimethoxycinnamic acid propyl ester
  参考文献：
  名称：

  靶向 5-脂氧合酶产物生物合成的新芥子酸苯乙酯类似物的构效关系研究：酚基、酯功能和生物等排性的作用

  摘要：

  芥子酸存在于许多可食用植物和水果中，例如油菜籽，它是主要的酚类化合物。合成并筛选了新的芥子酸苯乙酯 (SAPE) 类似物作为受刺激的 HEK293 细胞和多形核白细胞 (PMNL) 中 5-脂氧合酶 (5-LO) 生物合成的抑制剂。抑制 5-LO 催化的白三烯生物合成是针对某些炎症性疾病和过敏症的有效治疗策略。不幸的是，迄今为止唯一获批的抑制剂由于其药代动力学特征和肝毒性较差，临床应用有限。利用本研究中合成的新类似物，研究了酚部分、酯功能和生物等排性的作用。34 种化合物中有几种抑制 5-LO 产物的生物合成，在 PMNL 中，20 种化合物的效力是齐留通的 2-11 倍，后者是 5-LO 产品的重要生产商。化合物在苯乙基部分的间位带有 4-三氟甲基、甲基或甲氧基取代基的5i (IC 50 : 0.20 μM)、5l (IC 50 : 0.20 μM) 和5o (IC 50 : 0.21 μM)

  DOI：

  10.1021/acs.jnatprod.1c00982

文献信息

• Antimicrobial compositions
  申请人：Novozymes A/S

  公开号：US20020102246A1

  公开（公告）日：2002-08-01

  The present invention relates to an enzymatic method for killing or inhibiting microbial cells or microorganisms, e.g. in laundry, on hard surfaces, in water systems, on skin, on teeth or on mucous membranes. The present invention also relates to the use of said enzymatic composition for preserving food products, cosmetics, paints, coatings, etc.

  本发明涉及一种用于杀灭或抑制微生物细胞或微生物的酶法，例如在洗涤、硬表面、水系统、皮肤、牙齿或粘膜上。本发明还涉及利用所述酶性组合物来保护食品产品、化妆品、涂料等的用途。
• Dietary Phenolic Acids and Derivatives. Evaluation of the Antioxidant Activity of Sinapic Acid and Its Alkyl Esters
  作者：Alexandra Gaspar、Marta Martins、Paulo Silva、E. Manuela Garrido、Jorge Garrido、Omidreza Firuzi、Ramin Miri、Luciano Saso、Fernanda Borges

  DOI：10.1021/jf103075r

  日期：2010.11.10

  and lipophilicity of these phenolic compounds were also evaluated. From the overall results it was concluded that alkyl ester sinapates (linear alkyl esters) present almost the same antioxidant activity, albeit slightly lower, exhibited by the parent compound (sinapic acid). Furthermore, the addition of an alkyl ester side chain has a positive effect on the partition coefficient of sinapic acid, improving

  已经研究了芥子酸及其烷基酯作为潜在的抗氧化剂的作用。为此目的，合成了一系列芥子酸酯衍生物，并使用独特的分析方法，即2,2-二苯基-1-吡啶并乙酰肼（DPPH）和FRAP UV-vis方法以及差示扫描量热法对它们的抗氧化活性进行了评估。还评估了这些酚类化合物的供电子活性和亲脂性。从总体结果可以得出结论，母体化合物（芥子酸）表现出烷基芥子酸酯（线性烷基酯）具有几乎相同的抗氧化活性，尽管稍低。此外，添加烷基酯侧链对芥子酸的分配系数有积极的影响，在亲脂性更强的介质中提高了其作为抗氧化剂的效用。通过不同分析方法获得的抗氧化活性数据相互关联良好，并且揭示了芥子酸烷基酯的有趣抗氧化数据。
• Discovery of neurotrophic agents based on hydroxycinnamic acid scaffold
  作者：Razieh Hosseini、Fatemeh Moosavi、Hamid Rajaian、Tiago Silva、Diogo Magalhães e Silva、Pedro Soares、Luciano Saso、Najmeh Edraki、Ramin Miri、Fernanda Borges、Omidreza Firuzi

  DOI：10.1111/cbdd.12829

  日期：2016.12

  The number of people affected by neurodegenerative disorders such as Alzheimer's disease and Parkinson's disease is rapidly increasing owing to the global increase in life expectancy. Small molecules with neurotrophic effects have great potential for management of these neurological disorders. In this study, different (C1–C12) alkyl ester derivatives of hydroxycinnamic acids (HCAs) were synthesized (a total of 30 compounds). The neurotrophic capacity of the test compounds was examined by measuring promotion of survival in serum‐deprived conditions and enhancement of nerve growth factor (NGF)‐induced neurite outgrowth in PC12 neuronal cells. p‐Coumaric, ferulic, and sinapic acids and their esters did not alter cell survival, while caffeic acid and all its alkyl esters, especially decyl and dodecyl caffeate, significantly promoted neuronal survival at 25 μm. Methyl, ethyl, propyl, and butyl caffeate esters also significantly enhanced NGF‐induced neurite outgrowth, among which the most effective ones were propyl and butyl esters, which at 5 μm led to 25‐ and 22‐fold increases in the number of neurites, respectively. The findings of the docking study suggested phosphatidylinositol 3‐kinase (PI3K) as the potential molecular target. In conclusion, our findings demonstrate that alkyl esters of caffeic acid can be useful as scaffolds for the discovery of therapeutic agents for neurodegenerative diseases.
• [EN] OXIDOREDUCTASE MEDIATED ANTIMICROBIAL ACTIVITY<br/>[FR] ACTIVITE ANTIMICROBIENNE INDUITE PAR OXYDOREDUCTASE
  申请人：NOVOZYMES AS

  公开号：WO2001084937A1

  公开（公告）日：2001-11-15

  The present invention relates to an enzymatic method for killing or inhibiting microbial cells or micro-organisms, e.g. in laundry, on hard surfaces, in water systems, on skin, on teeth or on mucous membranes. The present invention also relates to the use of said enzymatic composition for preserving food products, cosmetics, paints, coatings, etc.
• Structure–Activity Relationship Studies of New Sinapic Acid Phenethyl Ester Analogues Targeting the Biosynthesis of 5-Lipoxygenase Products: The Role of Phenolic Moiety, Ester Function, and Bioisosterism
  作者：Mohamed Touaibia、Diene Codou Faye、Jérémie A. Doiron、Audrey Isabel Chiasson、Sébastien Blanchard、Pierre-Philippe Roy、Marc E. Surette

  DOI：10.1021/acs.jnatprod.1c00982

  日期：2022.1.28

  toxicity. With the new analogues synthesized in this study, the role of the phenolic moiety, ester function, and bioisosterism was investigated. Several of the 34 compounds inhibited the biosynthesis of 5-LO products, and 20 compounds were 2–11 times more potent than zileuton in PMNL, which are important producers of 5-LO products. Compounds 5i (IC50: 0.20 μM), 5l (IC50: 0.20 μM), and 5o (IC50: 0.21 μM)

  芥子酸存在于许多可食用植物和水果中，例如油菜籽，它是主要的酚类化合物。合成并筛选了新的芥子酸苯乙酯 (SAPE) 类似物作为受刺激的 HEK293 细胞和多形核白细胞 (PMNL) 中 5-脂氧合酶 (5-LO) 生物合成的抑制剂。抑制 5-LO 催化的白三烯生物合成是针对某些炎症性疾病和过敏症的有效治疗策略。不幸的是，迄今为止唯一获批的抑制剂由于其药代动力学特征和肝毒性较差，临床应用有限。利用本研究中合成的新类似物，研究了酚部分、酯功能和生物等排性的作用。34 种化合物中有几种抑制 5-LO 产物的生物合成，在 PMNL 中，20 种化合物的效力是齐留通的 2-11 倍，后者是 5-LO 产品的重要生产商。化合物在苯乙基部分的间位带有 4-三氟甲基、甲基或甲氧基取代基的5i (IC 50 : 0.20 μM)、5l (IC 50 : 0.20 μM) 和5o (IC 50 : 0.21 μM)