hexyl (E)-3-(4-hydroxy-3-methoxyphenyl)-2-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: hexyl (E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoate
• 英文别名: trans-hexyl 3-(4-hydroxy-3-methoxyphenyl)propenoate；(E)-hexyl 3-(4-hydroxy-3-methoxyphenyl) acrylate；hexyl ferulate；hexylferulate；hexyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• 化学式: C₁₆H₂₂O₄
• 分子量: 278.348
• InChiKey: GSUPPTOWPNFMPI-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  阿魏酸 、 溴己烷 在 水 、 sodium hydroxide 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 1.0h， 以27%的产率得到hexyl (E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoate
  参考文献：
  名称：

  Lipophilic phenolic antioxidants: Correlation between antioxidant profile, partition coefficients and redox properties

  摘要：

  Lipophilic compounds structurally based on caffeic, hydrocaffeic, ferulic and hydroferulic acids were synthesized. Subsequently, their antioxidant activity was evaluated as well as their partition coefficients and redox potentials. The structure-property-activity relationship (SPAR) results revealed the existence of a clear correlation between the redox potentials and the antioxidant activity. In addition, some compounds showed a proper lipophilicity to cross the blood-brain barrier. Their predicted ADME properties are also in accordance with the general requirements for potential CNS drugs. Accordingly, one can propose these phenolic compounds as potential antioxidants for tackling the oxidative status linked to the neurodegenerative processes. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.090

文献信息

• Alkyl ferulic acid esters: Evaluating their structure and antibacterial properties
  作者：Wei Song、Jiaying Xin、Chong Yu、Chungu Xia、Yu Pan

  DOI：10.3389/fmicb.2023.1135308

  日期：——

  Ferulic acid (FA) is a natural antibacterial agent rich in plants, FA has excellent antioxidant and antibacterial properties. However, because of its short alkane chain and large polarity, FA is difficult to penetrate the soluble lipid bilayer in the biofilm to enter the cell to play an inhibitory role, limiting its biological activity. To improve the antibacterial activity of FA, with the catalytic condition

  阿魏酸（FA）是一种富含植物的天然抗菌剂，FA具有优良的抗氧化和抗菌性能。但由于其烷烃链短、极性大，FA难以穿透生物膜中的可溶性脂双层进入细胞内发挥抑制作用，限制了其生物活性。为了提高FA的抗菌活性，在Novozym 435的催化条件下，通过脂肪醇（包括1-丙醇（C3）、1-己醇（C6）、1-己醇（C6）、壬醇（C9）和月桂醇（C12））修饰。FC 对铜绿假单胞菌通过最低抑菌浓度（MIC）、最低杀菌浓度（MBC）、生长曲线、碱性磷酸酶（AKP）活性、结晶紫法、扫描电镜（SEM）、膜电位、PI、细胞内容物渗漏测定。结果表明，酯化后FCs的抗菌活性增加，且抗菌活性随着FCs烷基链的延长而显着升高后降低。阿魏酸己酯 (FC6) 对大肠杆菌和铜绿假单胞菌（麦克风为大肠杆菌为 0.5 mg/ml，MIC 为铜绿假单胞菌为 0.4 毫克/毫升）。阿魏酸丙酯 (FC3) 和 FC6 对金黄色葡萄球菌和枯草芽孢杆菌（麦克风为金黄色葡萄球菌为
• Enzymatic synthesis of phenolic acid esters and steryl phenolates
  申请人：ETH Zurich

  公开号：EP2886657A1

  公开（公告）日：2015-06-24

  The present invention relates to a method for obtaining at least one steryl phenolate from at least one phenolic acid in an enzymatic process using a lipase, wherein in a first step a) the at least one phenolic acid and at least one alcohol R1-OH undergo an enzymatic esterification to at least one phenolic acid ester according to reaction scheme (III) , and in at least one second step b) the at least one phenolic acid ester and at least one sterol R2-OH undergo an enzymatic transesterification using a lipase to at least one steryl phenolate according to reaction scheme (IV)

  本发明涉及一种通过使用脂肪酶的酶法工艺从至少一种酚酸中获得至少一种甾基苯酚的方法，其中第一步 a) 至少一种酚酸和至少一种醇 R1-OH 根据反应方案 (III) 进行酶法酯化，生成至少一种酚酸酯 在至少一个第二步中，b) 至少一种酚酸酯和至少一种甾醇 R2-OH 按照反应方案 (IV) 使用脂肪酶进行酶促酯化反应，生成至少一种苯酚甾酯
• 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.
• PROPOLIS AND CAFFEIC ACID PHENETHYL ESTER AND USES THEREOF
  申请人：NEW YORK UNIVERSITY

  公开号：US20140127316A1

  公开（公告）日：2014-05-08

  Methods for treating a subject with cancer using a combined therapeutic regimen comprising administering propolis or caffeic acid phenethyl ester (CAPE) in conjunction with other cancer therapeutics are described herein. More particularly, methods for treating subjects with breast cancer using the combined therapeutic regimen are embodied herein. The present methods are particularly useful for treating cancer patients (e.g., breast cancer patients) who are refractory to or who have become refractory to the cancer therapeutic/s used in combination with propolis or CAPE. Propolis or CAPE for use in a combined treatment with other cancer therapeutics for treating cancer patients and compositions comprising propolis or CAPE and other cancer therapeutics are also encompassed herein wherein the ability of propolis or CAPE to act as a histone deacetylase (HDAC) inhibitor is used to advantage. Also encompassed herein are methods and compositions for the treatment of diseases caused by or associated with viral infections. In particular embodiments, methods and compositions for the treatment of viral infections caused by or associated with retroviruses are envisioned, wherein the ability of propolis or CAPE to act as a histone deacetylase (HDAC) inhibitor is also used to advantage. Also encompassed herein are methods and compositions for the treatment of diseases caused by or associated with viral infections.
• [EN] PROPOLIS AND CAFFEIC ACID PHENETHYL ESTER AND USES THEREOF<br/>[FR] PROPOLIS ET ESTER PHÉNÉTYLIQUE DE L'ACIDE CAFÉIQUE, ET LEURS UTILISATIONS
  申请人：UNIV NEW YORK

  公开号：WO2013012477A1

  公开（公告）日：2013-01-24

  Methods for treating a subject with cancer using a combined therapeutic regimen comprising administering propolis or caffeic acid phenethyl ester (CAPE) in conjunction with other cancer therapeutics are described herein. More particularly, methods for treating subjects with breast cancer using the combined therapeutic regimen are embodied herein. The present methods are particularly useful for treating cancer patients (e.g., breast cancer patients) who are refractory to or who have become refractory to the cancer therapeutic/s used in combination with propolis or CAPE. Propolis or CAPE for use in a combined treatment with other cancer therapeutics for treating cancer patients and compositions comprising propolis or CAPE and other cancer therapeutics are also encompassed herein wherein the ability of propolis or CAPE to act as a histone deacetylase (HDAC) inhibitor is used to advantage. Also encompassed herein are methods and compositions for the treatment of diseases caused by or associated with viral infections.