Dodecyl caffeate

• 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: Dodecyl caffeate
• 英文别名: n-dodecanyl caffeate；trans-dodecyl 3-(3,4-dihydroxyphenyl)propenoate；3,4-dihydroxycinnamic acid n-dodecylester；2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, dodecyl ester；dodecyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• 化学式: C₂₁H₃₂O₄
• 分子量: 348.483
• InChiKey: XXFZUZXCHYDOJO-FYWRMAATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  25
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  TRANS-咖啡酸 在 氯化亚砜 作用下， 以 1,4-二氧六环 为溶剂， 反应 9.0h， 生成 Dodecyl caffeate
  参考文献：
  名称：

  Selective antiproliferative activity of caffeic acid phenethyl ester analogues on highly liver-Metastatic murine colon 26-L5 carcinoma cell line

  摘要：

  Caffeic acid phenethyl ester (CAPE, 2) and its twenty analogues (1, 3-21) were prepared. These esters were tested by MTT assay on growth of murine colon 26-L5 carcinoma, murine B16-BL6 malonoma, murine Lewis lung carcinoma, human HT-1080 fibrosarcoma, human lung A549 adenocarcinoma, and human cervix HeLa adenocarcinoma cell lines. It was found that CAPE analogues possessed selective antiproliferative activity toward highly liver-metastatic murine colon 26-L5 carcinoma cell line. Among them, 4-phenylbutyl caffeate (4), (Z)-8-phenyl-7-octenyl (10a) and (E)-8-phenyl-7-octenyl (10b) caffeate showed the most potent antiproliferative activity (EC50 value, 0.02 muM). In addition, CAPE (2) induced DNA fragmentation at concentrations of 1 to 10 mug/mL towards murine colon 26-L5 carcinoma cells. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00138-4

文献信息

• PAIN RELIEF COMPOUNDS
  申请人：ECOLE NATIONALE SUPERIEURE DE CHIMIE DE CLERMONT FERRAND

  公开号：US20150038466A1

  公开（公告）日：2015-02-05

  The present invention relates to the use of compounds for the treatment or prevention of pain in mammals, in particularly in human beings, and also to a process for preparing these compounds.

  本发明涉及使用化合物治疗或预防哺乳动物（尤其是人类）的疼痛，并且涉及一种制备这些化合物的方法。
• [EN] CAFFEIC ACID DERIVATIVES AND USES THEREOF<br/>[FR] DÉRIVÉS D'ACIDE CAFÉIQUE ET LEURS UTILISATIONS
  申请人：MUSC FOUND FOR RES DEV

  公开号：WO2017161093A1

  公开（公告）日：2017-09-21

  The present invention relates to compounds of formula (I): including any stereochemically isomeric form thereof, or pharmaceutically acceptable salts thereof, for the treatment of tuberculosis.

  本发明涉及公式(I)的化合物，包括其任何立体化异构体，或其药用可接受的盐，用于治疗结核病。
• Lipophilic alkyl caffeate synthesis using a novel green binuclear ionic liquid 1,1-bis(2-pyrrolidinone) sulfate ([C3(Hnhp)2][HSO4]2) catalyst
  作者：Xuejing Liu、Yaoyao Zhang、Shangde Sun

  DOI：10.1016/j.foodchem.2023.137500

  日期：2024.2

  successfully synthesized and characterized by FT-IR and 1H NMR. The physico-chemical properties of [C3(Hnhp)2][HSO4]2, including the density, viscosity, thermal stability and Brønsted acidity, were analyzed. As a novel catalyst for the esterification of CA with model dodecanol, its catalytic performance was investigated and optimized by response surface methodology. Under the optimal conditions, a 95

  咖啡酸（CA）作为一种潜在的绿色抗氧化剂，在食品加工中发挥着重要作用。然而，CA的低脂溶性限制了其应用。为了克服这个问题，通常通过引入亲脂基团（例如烷基醇）来修饰CA，从而形成咖啡酸烷基酯，从而可以显着增强CA的脂溶性。在本研究中，成功​​合成了双核离子液体1,1-双(2-吡咯烷酮)硫酸盐([C 3 (Hnhp) 2 ][HSO 4 ] 2 )，并通过FT-IR和1 H NMR进行了表征。分析了[C 3 (Hnhp) 2 ][HSO 4 ] 2的物理化学性质，包括密度、粘度、热稳定性和布朗斯台德酸度。作为CA与模型十二醇酯化反应的新型催化剂，采用响应面法对其催化性能进行了研究和优化。在最佳条件下，十二烷醇咖啡酸酯的产率为95.42±1.01%。此外，[C 3 (Hnhp) 2 ][HSO 4 ] 2表现出优异的稳定性和可重复使用性，使其成为合成各种亲脂性咖啡酸烷基酯的极具前景的催化剂。
• Impact of Alkyl Esters of Caffeic and Ferulic Acids on Tumor Cell Proliferation, Cyclooxygenase Enzyme, and Lipid Peroxidation
  作者：Bolleddula Jayaprakasam、Mulabagal Vanisree、Yanjun Zhang、David L. Dewitt、Muraleedharan G. Nair

  DOI：10.1021/jf060899p

  日期：2006.7.1

  The antioxidant ferulic and caffeic acid phenolics are ubiquitous in plants and abundant in fruits and vegetables. We have synthesized a series of ferulic and caffeic acid esters and tested for tumor cell proliferation, cyclooxygenase enzymes (COX-1 and -2) and lipid peroxidation inhibitory activities in vitro. In the tumor cell proliferation assay, some of these esters showed excellent growth inhibition of colon cancer cells. Among the phenolics esters assayed, compounds 10 (C-12-caffeate), 11 (C-16-caffeate), 21 (C-8-ferulate), and 23 (C-12-ferulate) showed strong growth inhibition with IC50 values of 16.55, 13.46, 18.67, and 7.57 mu g/mL in a breast cancer cell line; 9.65, 7.45, 17.05, and 4.35 mu g/mL in a lung cancer cell line; 5.78, 3.5, 4.29, and 2.46 mu g/mL in a colon cancer cell line; 12.04, 12.21, 14.63, and 8.09 mu g/mL in a central nervous system cancer cell line; and 8.62, 7.76, 11.0, and 5.37 in a gastric cancer cell line. In COX enzyme inhibitory assays, ferulic and caffeic acid esters significantly inhibited both COX-1 and COX-2 enzymes. Caffeates 5-10 (C-4-C-12), inhibited COX-1 enzyme between 50% and 90% and COX-2 enzyme by about 70%, whereas ferulates 15-21 (C-3-C-8) inhibited COX-1 and COX-2 enzymes by 85-95% 25 mu g/mL. Long-chain caffeates 11-14 (C-16-C-22) and short-chain ferulates 15-20 (C-3-C-5) were the most active in lipid peroxidation inhibition and showed 6070% activity at 5 mu g/mL concentration.
• 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.