E-咖啡酸戊酯 | 136944-11-1

• 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
• 中文名称: E-咖啡酸戊酯
• 中文别名: 丁酸,2,2'-[亚环己基二(4,1-亚苯基氧代)]二[2-甲基-,(R*,R*)-(-)-(9CI)
• 英文名称: Caffeic Acid n-Pentyl Ester
• 英文别名: pentyl (E)-3-(3,4-dihydroxyphenyl)acrylate；pentyl caffeate；amyl caffeate；E-Caffeic acid pentyl ester；pentyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• CAS: 136944-11-1
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: ULPIXLKKVGJPCT-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 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：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  E-咖啡酸戊酯 、 阿司匹林 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到pentyl (E)-3-[3,4-bis(2-acetoxybenzoyloxy)phenyl]acrylate
  参考文献：
  名称：

  Design and Synthesis of Novel Aspirin-Caffeic Acid Ester Hybrids for Cardioprotection with Reduced Risk of Hemorrhagic Stroke

  摘要：

  一系列新型阿司匹林-咖啡酸酯杂合体被设计并合成为降低出血性卒中风险的护心药物，灵感来自NCX-4016。通过ADP诱导的体外抗血小板聚集和DPPH试验测定了所合成化合物中能够被酯酶如NCX 4016在体内释放的咖啡酸酯的抗氧化活性。结果显示，化合物3d展现出了比阿司匹林及其中间体咖啡酸异丙酯（2d）更强的抗血小板活性，而且表现出良好的抗氧化活性，因而可被认为是降低出血性卒中风险的新型高效护心药物候选者。

  DOI：

  10.14233/ajchem.2015.17896
• 作为产物：
  描述：

  戊醇 、 (E)-3-(3,4-dihydroxyphenyl)acryloyl chloride 生成 E-咖啡酸戊酯
  参考文献：
  名称：

  Impact of Alkyl Esters of Caffeic and Ferulic Acids on Tumor Cell Proliferation, Cyclooxygenase Enzyme, and Lipid Peroxidation

  摘要：

  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.

  DOI：

  10.1021/jf060899p

文献信息

• Enzymatic Synthesis and Antioxidant Activity of 1-Caffeoylglycerol Prepared from Alkyl Caffeates and Glycerol
  作者：Xiang-Yun Meng、Yan Xu、Jin-Xian Wu、Chang-Tong Zhu、Dong-Yang Zhang、Guo-Hua Wu、Fu-An Wu、Jun Wang

  DOI：10.1002/aocs.12036

  日期：2018.2

  CA, 1‐caffeoylglycerol (1‐CG) was synthesized by lipase‐catalyzed transesterification of alkyl caffeates in solvent‐free system and its antioxidant capacity was investigated. Methyl caffeate was screened as the appropriate substrate from tested alkyl caffeates with a yield of 90.63%. Ethyl acetate was used for extracting 1‐CG from enzymatic reactants and could be easily recycled. The produced 1‐CG had

  咖啡酸（CA）作为强抗氧化剂，在非极性介质中的溶解度较低，这限制了其在食品工业中的应用。为了增加CA的亲脂性，在无溶剂体系中，通过脂肪酶催化烷基咖啡酸酯的酯交换反应合成了1-咖啡酰甘油（1-CG），并研究了其抗氧化能力。从测试的咖啡酸烷基酯中筛选出咖啡酸甲酯作为合适的底物，收率为90.63％。乙酸乙酯用于从酶促反应物中提取1-CG，并易于回收利用。产生的1–CG的半数最大抑制浓度（IC 50）（10.86和3.99μM）分别比1,1-二苯基-2-吡啶甲基肼基自由基清除和β的丁基化羟基茴香醚低2.5和10倍-胡萝卜素-亚油酸测定法。因此，1-CG是用于功能性食品行业的出色抗氧化剂。在无溶剂的系统中，使用烷基咖啡酸酯和甘油作为底物，通过固定化脂肪酶催化生产1-CG是一种简单，选择性和安全的生物过程，可以在食品工业中轻松实现，并且1-CG产品的应用范围很广用于食品，营养保健品和生物技术产品。
• Synthesis, antifungal activity of caffeic acid derivative esters, and their synergism with fluconazole and nystatin against Candida spp.
  作者：Janaína de Cássia Orlandi Sardi、Fernanda Patrícia Gullo、Irlan Almeida Freires、Nayla de Souza Pitangui、Maicon Petrônio Segalla、Ana Marisa Fusco-Almeida、Pedro Luiz Rosalen、Luís Octávio Regasini、Maria José Soares Mendes-Giannini

  DOI：10.1016/j.diagmicrobio.2016.08.002

  日期：2016.12

  We tested the antifungal potential of caffeic acid and 8 of its derivative esters against Candidaalbicans ATCC 90028 and 9 clinical isolatesand carried out a synergism assay with fluconazole and nystatin. Propyl caffeate (C3) showed the best antifungal activity against the tested strains. When in combination, C3 markedly reduced the MIC of fluconazole and nystatin with synergistic effect up to 64-fold

  我们测试了咖啡酸及其8种衍生物对白念珠菌ATCC 90028和9种临床分离株的抗真菌潜力，并与氟康唑和制霉菌素进行了协同试验。咖啡酸丙酯（C3）对测试菌株显示出最佳的抗真菌活性。组合使用时，C3可以显着降低氟康唑和制霉菌素的MIC，协同作用最多可达到64倍。最后，C3对口服角质形成细胞表现出较高的IC50值和选择性指数，表明对这种细胞类型的毒性低，对酵母细胞的选择性低。进一步的研究应证实其抗真菌潜力，可用于开发治疗白色念珠菌感染的联合疗法。
• A lipoxygenase inhibitor
  申请人：GREEN CROSS CORPORATION

  公开号：EP0163270A2

  公开（公告）日：1985-12-04

  A lipoxygenase inhibitor comprising as active ingredient a substituted styrene derivative having a radical of the general formula wherein X denotes a hydroxyl group or a lower alkoxy group and q is an integer of 2 or 3, and containing carbon atoms in total of at least 8.

  一种脂氧合酶抑制剂，其活性成分包括具有通式基团的取代苯乙烯衍生物，其中 X 表示羟基或低级烷氧基，q 为 2 或 3 的整数，且总共含有至少 8 个碳原子。
• Pharmaceutical composition containing slightly water-soluble drug
  申请人：THE GREEN CROSS CORPORATION

  公开号：EP0448091A2

  公开（公告）日：1991-09-25

  The orally administrable pharmaceutical compositions containing a slightly water-soluble drug, characterized by improved stability and improved absorption of the drug from digestive tract into blood. The use of the compositions of the present invention enables decrease of the dose amount of a slightly water-soluble drug, which eventually leads to alleviation of pains and side effects on the part of patients.

  本发明的口服药物组合物含有微水溶性药物，其特点是稳定性更好，药物从消化道进入血液的吸收率更高。使用本发明的组合物可以减少微水溶性药物的剂量，从而最终减轻患者的痛苦和副作用。
• US4733002A
  申请人：——

  公开号：US4733002A

  公开（公告）日：1988-03-22