(E)-butyl 3-(4-hydroxy-3,5-dimethoxyphenyl )propenoate

• 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)-butyl 3-(4-hydroxy-3,5-dimethoxyphenyl )propenoate
• 英文别名: (E)-butyl 3-(3,5-dimethoxy-4-hydroxyphenyl)propenoate；butyl (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)acrylate；n-butyl 3,5-dimethoxy-4-hydroxycinnamate；butyl sinapate；butyl (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
• 化学式: C₁₅H₂₀O₅
• 分子量: 280.321
• InChiKey: ADHXGGDIBVABLZ-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  (E)-3-(4-Benzyloxy-3,5-dimethoxy-phenyl)-acrylic acid butyl ester 在 三氯化铝 、 N,N-二甲基苯胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (E)-butyl 3-(4-hydroxy-3,5-dimethoxyphenyl )propenoate
  参考文献：
  名称：

  Venkateswarlu, Somepalli; Ramachandra, Mareullapudi S.; Krishnaraju, Alluri V., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 1, p. 252 - 257

  摘要：

  DOI：

文献信息

• Long Chain Alkyl Esters of Hydroxycinnamic Acids as Promising Anticancer Agents: Selective Induction of Apoptosis in Cancer Cells
  作者：José C. J. M. D. S. Menezes、Najmeh Edraki、Shrivallabh P. Kamat、Mahsima Khoshneviszadeh、Zahra Kayani、Hossein Hadavand Mirzaei、Ramin Miri、Nasrollah Erfani、Maryam Nejati、José A. S. Cavaleiro、Tiago Silva、Luciano Saso、Fernanda Borges、Omidreza Firuzi

  DOI：10.1021/acs.jafc.7b01388

  日期：2017.8.23

  alkyl esters may possess enhanced biological activities. We evaluated C4, C14, C16, and C18 alkyl esters of p-coumaric, ferulic, sinapic, and caffeic acids (19 compounds) for their cytotoxic activity against four human cancer cells and also examined their effect on cell cycle alteration and apoptosis induction. The tetradecyl (1c) and hexadecyl (1d) esters of p-coumaric acid and tetradecyl ester of caffeic

  癌症是全世界发病率和死亡率的主要原因。羟基肉桂酸（HCA）是天然存在的化合物，其烷基酯可能具有增强的生物活性。我们评估了对香豆酸，阿魏酸，芥子酸和咖啡酸（19种化合物）的C4，C14，C16和C18烷基酯对四种人类癌细胞的细胞毒活性，并且还研究了它们对细胞周期改变和凋亡诱导的影响。对香豆酸的十四烷基（1c）和十六烷基（1d）和咖啡酸（4c）的十四烷基酯（而非亲本的HCA）具有IC 50对MOLT-4（人淋巴细胞白血病）细胞的选择性作用。分别为0.123±0.012、0.301±0.069和1.0±0.1μM。化合物1c，1d和4c显着增加了亚G1期的凋亡细胞，并激活了MOLT-4细胞中的caspase-3酶。化合物1c对抗药性MES-SA-DX5子宫肉瘤细胞的效力分别比阿霉素和顺铂高15.4倍和23.6倍。这些对香豆酸酯对NIH / 3T3成纤维细胞的功效要低好几倍。对接研究表明1c可能通
• Selective Depolymerisation of γ‐Oxidised Lignin via NHC Catalysed Redox Esterification
  作者：Ganyuan Xiao、Christopher S. Lancefield、Nicholas J. Westwood

  DOI：10.1002/cctc.201900787

  日期：2019.7.18

  The development of new catalytic methods for the processing of lignocellulose‐derived renewable feedstocks continues to gain momentum, despite the considerable challenges associated with the use of complex biopolymers such as lignin. Here, we report a new two‐step depolymerisation method for lignin involving primary alcohol oxidation followed by a NHC‐mediated redox esterification‐depolymerisation

  尽管使用复杂的生物聚合物（如木质素）面临着巨大挑战，但用于处理木质纤维素衍生的可再生原料的新催化方法的开发仍在继续发展。在这里，我们报告了一种新的木质素两步解聚方法，涉及伯醇氧化，然后是NHC介导的氧化还原酯化解聚步骤。该方法利用了所使用的特定类型木质素（丁醇）中存在的β-芳基醚单元的固有结构，并提供了4种保留C 3的新型芳族单体。木质素亚基中存在侧链。对主要产品的实用性进行了评估，表明可以从这种可再生建筑材料中快速获得各种有趣的化学物质。
• 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.
• Venkateswarlu, Somepalli; Ramachandra, Mareullapudi S.; Krishnaraju, Alluri V., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 1, p. 252 - 257
  作者：Venkateswarlu, Somepalli、Ramachandra, Mareullapudi S.、Krishnaraju, Alluri V.、Trimurtulu, Golakoti、Subbaraju, Gottumukkala V.

  DOI：——

  日期：——