dodecyl ferulate | 864082-02-0

• 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 ferulate
• 英文别名: dodecyl (E)-3-(4-hydroxy-3-methoxyphenyl)-prop-2-enoate；(e)-Dodecyl 3-(4-hydroxy-3-methoxyphenyl)acrylate；dodecyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• CAS: 864082-02-0
• 化学式: C₂₂H₃₄O₄
• 分子量: 362.51
• InChiKey: GSGVKEOQRLQPPH-JQIJEIRASA-N

物化性质

• 熔点：
  46 °C
• 沸点：
  481.3±30.0 °C(Predicted)
• 密度：
  1.022±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  26
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  环氧氯丙烷 、 dodecyl ferulate 在 sodium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 反应 8.0h， 以83%的产率得到dodecyl (2E)-3-[3-methoxy-4-(oxiran-2-ylmethoxy)phenyl]acrylate
  参考文献：
  名称：

  Synthesis of New L-Ascorbic Ferulic Acid Hybrids

  摘要：

  基于多种抗氧化剂混合物的已知协同效应，本文描述了L-抗坏血酸与阿魏酸衍生物耦合条件的可行性及化学研究。我们以保护醇功能和烯二醇体系为目标，制备了在C-3羟基上连接的新型L-抗坏血酸阿魏酸杂化物。

  DOI：

  10.3390/12112533
• 作为产物：
  描述：

  十二烷醇 在 吡啶 、 苯胺 作用下， 以 环己烷 、 甲苯 为溶剂， 反应 4.0h， 生成 dodecyl ferulate
  参考文献：
  名称：

  Discovery of neurotrophic agents based on hydroxycinnamic acid scaffold

  摘要：

  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.

  DOI：

  10.1111/cbdd.12829

文献信息

• Thermally stable ferulic acid derivatives
  申请人：——

  公开号：US20040152912A1

  公开（公告）日：2004-08-05

  A ferulic acid derivative represented by the general formula (1); a process for preparing a ferulic acid derivative represented by the general formula (1), comprising reacting ferulic acid or an ester thereof represented by the general formula (2) with a dihalomethane represented by the general formula CH 2 X 2 , wherein X is a halogen atom; and an ultraviolet light-absorbent composition comprising the ferulic acid derivative. Since the ultraviolet light absorbent composition is not only excellent in the ultraviolet light absorption but also very stable against heat, the ultraviolet light absorbent composition can be suitably used as cosmetics which especially require long-term stability.

  一种由通式（1）表示的香豆酸衍生物；一种制备由通式（1）表示的香豆酸衍生物的方法，包括将由通式（2）表示的香豆酸或其酯与由通式CH2X2表示的二卤甲烷（其中X是卤素原子）反应；以及包含该香豆酸衍生物的紫外光吸收组合物。由于该紫外光吸收组合物不仅在紫外光吸收方面表现出色，而且对热稳定性非常好，因此该紫外光吸收组合物可作为特别需要长期稳定性的化妆品而合适地使用。
• Natural product-inspired esters and amides of ferulic and caffeic acid as dual inhibitors of HIV-1 reverse transcriptase
  作者：Vijay P. Sonar、Angela Corona、Simona Distinto、Elias Maccioni、Rita Meleddu、Benedetta Fois、Costantino Floris、Nilesh V. Malpure、Stefano Alcaro、Enzo Tramontano、Filippo Cottiglia

  DOI：10.1016/j.ejmech.2017.02.054

  日期：2017.4

  Using an HIV-1 Reverse Transcriptase (RT)-associated RNase H inhibition assay as lead, bioguided fractionation of the dichloromethane extract of the Ocimum sanctum leaves led to the isolation of five triterpenes (1-5) along with three 3-methoxy-4-hydroxy phenyl derivatives (6-8). The structure of this isolates were determined by 1D and 2D NMR experiments as well as ESI-MS. Tetradecyl ferulate (8) showed

  使用HIV-1逆转录酶（RT）相关的RNase H抑制试验作为先导，乌头叶的二氯甲烷提取物的生物引导分级分离导致分离出5个三萜（1-5）和3个3-甲氧基-4 -羟基苯基衍生物（6-8）。该分离物的结构通过1D和2D NMR实验以及ESI-MS确定。阿魏十四酸（8）显示出有趣的RNase H IC50值为12.4μM，并且由于该次生代谢产物的合成可及性，因此进行了结构-活性关系研究。合成了一系列阿魏酸和咖啡酸的酯和酰胺，其中最活跃的是N-油基咖啡酰胺，对RT相关功能，核糖核酸酶H和DNA聚合酶均显示出强大的抑制活性。
• 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
• Highly Efficient Preparation of Lipophilic Hydroxycinnamates by Solvent-free Lipase-Catalyzed Transesterification
  作者：Petra Weitkamp、Klaus Vosmann、Nikolaus Weber

  DOI：10.1021/jf0611973

  日期：2006.9.1

  Various medium- or long-chain alkyl cinnamates and hydroxycinnamates, including oleyl p-coumarate as well as palmityl and oleyl ferulates, were prepared in high yield by lipase-catalyzed transesterification of an equimolar mixture of a short-chain alkyl cinnamate and a fatty alcohol such as lauryl, palmityl, and oleyl alcohol under partial vacuum at moderate temperature in the absence of solvents and drying agents in direct contact with the reaction mixture. Immobilized lipase B from Candida antarctica was the most effective biocatalyst for the various transesterification reactions. Transesterification activity of this enzyme was up to 56-fold higher than esterification activity for the preparation of medium- and long-chain alkyl ferulates. The relative transesterification activities found for C. antarctica lipase were of the following order: hydrocinnamate > cinnamate > 4- hydroxyhydrocinnamate > 3-methoxycinnamate > 2-methoxycinnamate approximate to 4-methoxycinnamate approximate to 3-hydroxycinnamate > hydrocaffeate approximate to 4-hydroxycinnamate > ferulate > 2-hydroxycinnamate > caffeate approximate to sinapate. With respect to the position of the hydroxy substituents at the phenyl moiety, the transesterification activity of C. antarctica lipase B increased in the order meta > para > ortho. The immobilized lipases from Rhizomucor miehei and Thermomyces lanuginosus demonstrated moderate and low transesterification activity, respectively. Compounds with inverse chemical structure, that is, 3-phenylpropyl alkanoates such as 3-(4-hydroxyphenyl) propyl oleate and 3-(3,4- dimethoxyphenyl) propyl oleate, were obtained by C. antarctica lipase-catalyzed transesterification of fatty acid methyl esters with the corresponding 3- phenylpropan-1-ols in high yield, as well.
• 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.