n-propyl ferulate | 59831-93-5

• 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 ferulate
• 英文别名: propyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• CAS: 59831-93-5
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: XTSFEXUEVQUSQE-FNORWQNLSA-N

物化性质

• 沸点：
  364.5±27.0 °C(Predicted)
• 密度：
  1.147±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  n-propyl ferulate 在 盐酸 、 水 作用下， 250.0 ℃ 、5.0 MPa 条件下， 反应 3.0h， 以50%的产率得到邻苯二酚
  参考文献：
  名称：

  布朗斯台德酸催化生物可再生阿魏酸及其衍生物串联降解成生物邻苯二酚。

  摘要：

  已经开发了将可生物更新的阿魏酸有效转化为生物邻苯二酚的方法。该转化包括在一个步骤中发生的两个连续的底物去官能化，即CO（去甲基化）和CC（去2-羧基乙烯基化）键裂解。该过程仅需要在加压热水（250°C，50 bar N2）中将阿魏酸与HCl（或H2 SO4）作为催化剂加热。在多种其他（生物可再生）底物上也显示出多功能性，可产生高达84％的二-（邻苯二酚，间苯二酚，对苯二酚）和三羟基苯（邻苯三酚，羟基喹啉），在大多数情况下，仅需简单提取即可进行后处理。

  DOI：

  10.1002/anie.201913023
• 作为产物：
  描述：

  ethyl 4-hydroxy-3-methoxycinnamate 在 Sporotrichum thermophile type C feruloyl esterase 、 水 、 乙酰氯 作用下， 反应 16.0h， 生成 n-propyl ferulate
  参考文献：
  名称：

  Mapping the hydrolytic and synthetic selectivity of a type C feruloyl esterase (StFaeC) from Sporotrichum thermophile using alkyl ferulates

  摘要：

  The active site of Sporotrichum thermophile type C feruloyl esterase (StFaeC) was probed using a series Of C-1-C-4 alkyl ferulates. The affinities for straight and branched alkyl ferulates were demonstrated by the K-m values of 1.64-0.51 and 0.19-0.1, respectively. Comparison of k(cat), and k(cat)/K-m values shows that the enzyme hydrolyzed n-propyl ferulate faster and iso-propyl ferulate more efficiently. Alkyl ferulates were applied also for substrate selectivity mapping of feruloyl esterase to catalyze feruloyl group transfer to L-arabinose, using as a reaction system a ternary water-organic mixture consisting of n-hexane, t-butanol and water. Lengthening the aliphatic side chain was the most significant factor causing lower synthetic activity of the enzyme. The reaction parameters affecting the feruloylation rate and the conversion of the enzymatic process, such as the temperature and substrate concentration have been investigated. Under identical reaction conditions, the enzyme feruloylated other monosaccharides such as D-arabinose, D-glucose, D-xylose, D-Mannose, D-fructose, D-galactose, D-ribose and model substrates such as 4-nitrophenyl alpha-L-arabinofuranoside and 4-nitrophenyl alpha-L-arabinopyranoside. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.037

文献信息

• Design, Synthesis, and<i>In Vitro</i>Antiplatelet Aggregation Activities of Ferulic Acid Derivatives
  作者：Peng-Xuan Zhang、Hang Lin、Cheng Qu、Yu-Ping Tang、Nian-Guang Li、Jun Kai、Guanxiong Shang、Baoquan Li、Li Zhang、Hui Yan、Pei Liu、Jin-Ao Duan

  DOI：10.1155/2015/376527

  日期：——

  In order to discover new compounds with antiplatelet aggregation activities, some ferulic acid (FA) derivatives were designed and synthesized. The in vitro antiplatelet aggregation activities of these compounds were assessed by turbidimetric test. The results showed that the target compound 7f had potent antiplatelet aggregation activity with its IC50 27.6 μmol/L, and 7f can be regarded as a novel potent

  为了发现具有抗血小板聚集活性的新化合物，设计并合成了一些阿魏酸（FA）衍生物。这些化合物的体外抗血小板聚集活性通过比浊试验进行评估。结果表明，目标化合物7f具有较强的抗血小板聚集活性，其IC50为27.6 μmol/L，7f可作为一种新型的有效抗血小板聚集候选物。
• Synthesis and Antifungal Activity of Cinnamic Acid Esters
  作者：Shinkichi Tawata、Shigehiko Taira、Naotada Kobamoto、Jun Zhu、Masanobu Ishihara、Seizen Toyama

  DOI：10.1271/bbb.60.909

  日期：1996.1

  Cinnamic, p-coumaric and ferulic acids were isolated from pineapple stems (Ananas comosus var. Cayenne). Twenty-four kinds of esters were prepared from these acids, alcohols and the components of Alpinia. Isopropyl 4-hydroxycinnamate (11) and butyl 4-hydroxycinnamate (12) were found to have almost the same effectiveness in antifungal activity against Pythium sp. at 10 ppm as that of the commercial

  从菠萝茎（Ananas comosus var。Cayenne）中分离了肉桂酸，对香豆酸和阿魏酸。由这些酸，醇和高良姜的成分制得二十四种酯。发现4-羟基肉桂酸异丙酯（11）和4-羟基肉桂酸丁酯（12）在对抗腐霉菌属的真菌活性方面具有几乎相同的功效。含量为商业杀菌剂异丙苯酚（kitazin P）的10 ppm。
• Method for Preparing P-Hydroxycinnamate by Using Ionic Liquid for Catalytic Lignin Depolymerization
  申请人：South China University of Technology

  公开号：US20200181058A1

  公开（公告）日：2020-06-11

  The present invention discloses a method for preparing p-hydroxycinnamate by using an ionic liquid for catalytic lignin depolymerization comprising: 1) preparation of a halogen metal-based ionic liquid: preparing the halogen metal-based ionic liquid by reacting an alkylimidazole chloride with a metal chloride by heating the same to 30° C. to 80° C. with stirring; and 2) catalytic depolymerization of lignin: mixing the halogen metal-based ionic liquid and lignin with an alcohol, and after N 2 replacement, heating the solution to 140° C. to 200° C. and reacting the solution for 4-8 h while stirring to prepare high value-added chemicals with p-hydroxycinnamate as a main product. The present invention has advantages of a simple process, mild conditions, environmental kindness, and high selectivity for a main product. The ionic liquid is simple in preparation, has a good atom economy, and is recyclable. Under optimal conditions, the yield of p-hydroxycinnamate can reach 40-80 mg/g.

  本发明公开了一种利用离子液体催化木质素裂解制备对羟基肉桂酸的方法，包括：1）制备卤金属基离子液体：将烷基咪唑氯化物与金属氯化物在30°C至80°C加热搅拌反应，制备卤金属基离子液体；2）木质素催化裂解：将卤金属基离子液体与木质素和醇混合，在氮气置换后，将溶液加热至140°C至200°C，搅拌反应4-8小时，制备以对羟基肉桂酸为主要产品的高附加值化学品。本发明具有工艺简单、条件温和、环保友好、主要产物选择性高的优点。该离子液体制备简单，原子经济性好，可循环利用。在最佳条件下，对羟基肉桂酸的产率可达40-80毫克/克。
• Laccase-catalyzed oxidative phenolic coupling of vanillidene derivatives
  作者：Mihaela-Anca Constantin、Jürgen Conrad、Uwe Beifuss

  DOI：10.1039/c2gc35848d

  日期：——

  The laccase-catalyzed oxidative phenolic coupling of vanillidene derivatives using aerial oxygen as the oxidant has been developed. Depending on the substitution pattern of the vanillidene double bond of the substrate, either dilactones, dihydrobenzo[b]furans or biphenyls are formed.

  已经开发了使用空气中的氧作为氧化剂的漆酶催化的香草醛衍生物的氧化酚偶联。取决于底物的香兰素双键的取代方式，双内酯，二氢苯并[ b ]呋喃或联苯 形成。
• Highly Efficient Esterification of Ferulic Acid Under Microwave Irradiation
  作者：Nian-Guang Li、Zhi-Hao Shi、Yu-Ping Tang、Bao-Quan Li、Jin-Ao Duan

  DOI：10.3390/molecules14062118

  日期：——

  A highly efficient synthesis of alkyl ferulates under microwave irradiation is described. The time of these reactions ranged from 3 to 5 minutes, which was much shorter than the traditional synthetic methods, and the alkyl ferulates were obtained in higher yields.

  描述了在微波辐射下高效合成阿魏酸烷基酯的方法。这些反应时间为3~5分钟，比传统的合成方法要短得多，并且以较高的收率获得了阿魏酸烷基酯。