n-propyl caffeate | 83504-42-1

• 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
• 英文名称: n-propyl caffeate
• 英文别名: propyl (E)-3-(3,4-dihydroxyphenyl)acrylate；propyl caffeate；3,4-dihydroxy-trans-cinnamic acid propyl ester；3,4-Dihydroxy-trans-zimtsaeure-propylester；3-(3,4-dihydroxy-phenyl)-acrylic acid n-propyl ester；Propyl 3-(3,4-Dihydroxyphenyl)Acrylate；propyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• CAS: 83504-42-1；142234-81-9
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: BPJXSLLUNRTWHM-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  n-propyl caffeate 以96的产率得到(E)-methyl 3-(3,4-bis(methoxymethoxy)phenyl)acrylate
  参考文献：
  名称：

  Tetrahedron 2015, 71, 3120-3130

  摘要：

  DOI：
• 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 n-propyl 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

• Design and Synthesis of Novel Aspirin-Caffeic Acid Ester Hybrids for Cardioprotection with Reduced Risk of Hemorrhagic Stroke
  作者：Zhi-Hao Shi、Nian-Guang Li、Yu-Ping Tang、Qian-Ping Shi、Wei Zhang、Peng-Xuan Zhang、Ze-Xi Dong、Wei Li、Jin-Ao Duan

  DOI：10.14233/ajchem.2015.17896

  日期：——

  A series of novel aspirin-caffeic acid ester hybrids for cardioprotection with reduced risk of hemorrhagic stroke were designed and synthesized by coupling aspirin and caffeic acid esters inspired by NCX-4016. The synthesized compounds were evaluated for their in vitro antiplatelet aggregations induced by ADP and antioxidant activity of the caffeic acid esters which could be released from the hybrids by esterases in vivo like NCX 4016 were determined by DPPH assay. The results showed that compound 3d exhibited potent antiplatelet activity than aspirin and its intermediate caffeic acid isopropyl ester (2d) showed good antioxidant activity and thus could be considered to be novel potent cardioprotectic drug candidates with reduced risk of hemorrhagic stroke.

  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。
• Syntheses of Certain 3-Aryl-2-propenoates and Evaluation of their Cytotoxicity
  作者：Nguyen-Hai Nam、Young-Jae You、Yong Kim、Dong-Ho Hong、Hwan-Mook Kim、Byung Zun Ahn

  DOI：10.1016/s0960-894x(01)00165-2

  日期：2001.5

  A series of 3-aryl-2-propenoates including cinnamates, (E)-methyl/ethyl 3-[2-(1,4-dimethoxy-5,8-dione)naphthalenyl]-2-propenoates (8ba, 8bb) and (E)-methyl/ethyl 3-[2-(1,4-dihydroxy-9,10-dione)anthracenyl]-2-propenoates (9aa,9ab) was synthesized and evaluated for antitumor cytotoxicity. It was found that the ortho- or para-dihydroxy funtionality on the aryl ring was essential for the cytotoxicity of

  一系列3-芳基-2-丙烯酸酯，包括肉桂酸酯，（E）-甲基/乙基3- [2-（2-（1,4-二甲氧基-5,8-二酮）萘] -2-丙烯酸酯（8ba，8bb）和合成（E）3- [2-（1,4-二羟基-9,10-二酮）蒽基] -2-丙烯酸（9aa，9ab）-甲基/乙基（9aa，9ab），并评估其抗肿瘤细胞毒性。发现芳基环上的邻或对二羟基官能对于肉桂酸酯的细胞毒性至关重要。化合物8ba，8bb和9aa，9ab对多种肿瘤细胞系显示出强力的细胞毒性。
• 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。
• Phenolic acid derivatives with potential anticancer properties––a structure–activity relationship study. Part 1: Methyl, propyl and octyl esters of caffeic and gallic acids
  作者：S.M. Fiuza、C. Gomes、L.J. Teixeira、M.T. Girão da Cruz、M.N.D.S. Cordeiro、N. Milhazes、F. Borges、M.P.M. Marques

  DOI：10.1016/j.bmc.2004.04.026

  日期：2004.7

  cytotoxic properties of polyphenolic acid derivatives, structurally related with the natural models caffeic and gallic acids, have been tested in human cervix adenocarcinoma cells (HeLa). Simultaneous structural information was obtained for these compounds through theoretical ab initio methods. This study was conducted for the following esters: methyl caffeate (MC, 1), propyl caffeate (PC, 2), octyl caffeate

  在人子宫颈腺癌细胞（HeLa）中已经测试了与自然模型咖啡酸和没食子酸相关的多酚酸衍生物的抗增殖和细胞毒性特性。通过理论上从头算的方法获得了这些化合物的同时结构信息。这项研究针对以下酯类进行：咖啡酸甲酯（MC，1），咖啡酸丙酯（PC，2），咖啡酸辛酯（OC，3），没食子酸甲酯（MG，4），没食子酸丙酯（PG，5）和辛基没食子酸酯（OG，6）。对其中某些化合物的显着生长抑制作用进行了评估，显然取决于它们的结构特征。发现标记的结构-活性关系（SAR），即羟基环取代基的数目，决定了这类系统的生物学作用。
• 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。