4'-羟基-3'-甲氧基肉桂酸丁酯 | 4657-33-4

• 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: 4'-羟基-3'-甲氧基肉桂酸丁酯
• 英文名称: butyl ferulate
• 英文别名: n-butyl ferulate；Butyl 4'-hydroxy-3'-methoxycinnamate；butyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• CAS: 4657-33-4
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: JTQRZRRDNZAHMH-SOFGYWHQSA-N

物化性质

• 沸点：
  190-194 °C(Press: 0.01 Torr)
• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2918990090

反应信息

• 作为反应物：
  描述：

  4'-羟基-3'-甲氧基肉桂酸丁酯 在 Sporotrichum thermophile type C feruloyl esterase 、 水 作用下， 生成 阿魏酸
  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
• 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 4'-羟基-3'-甲氧基肉桂酸丁酯
  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。
• (±)-trans-2-phenyl-2,3-dihydrobenzofurans as leishmanicidal agents: Synthesis, in vitro evaluation and SAR analysis
  作者：Freddy A. Bernal、Marcel Gerhards、Marcel Kaiser、Bernhard Wünsch、Thomas J. Schmidt

  DOI：10.1016/j.ejmech.2020.112493

  日期：2020.11

  (SI > 4.6). Nonetheless, structural optimization as further requirement was inferred from the high clearance of the most potent compound (8m) observed during determination in vitro of its metabolic stability. On the other hand, chiral separation of 8m and subsequent biological evaluation of its enantiomers demonstrated no effect of chirality on activity and cytotoxicity. Holistic analysis of in silico

  利什曼病是由利什曼原虫属的寄生虫引起的一种被忽视的热带病，在世界范围内造成了严重的疾病负担，对数百万人的生命构成了威胁，因此是主要的公共卫生问题。需要更有效且无毒的新疗法，特别是对于内脏利什曼病（一种最严重的疾病）。在二氢苯并呋喃以前具有抗霉菌活性的背景下，我们在此介绍一组70种反式-2-苯基-2,3-二氢苯并呋喃的合成及其对利什曼原虫donovani的体外活性的评估，并讨论结构-活动关系。化合物8m-o和8r表现出最高的效价（IC 50  <2μmol/ L）和抗真菌活性相对于对哺乳动物细胞的细胞毒性的有趣的选择性（SI> 4.6）。尽管如此，从体外代谢测定中观察到的最有效化合物（8m）的高清除率可以推断出结构优化是进一步的要求。另一方面，手性分离8m并随后对其对映异构体进行生物学评估表明，手性对活性和细胞毒性没有影响。通过简单的评分函数估算药物相似性对计算机模拟ADME的性质和配体效率
• 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。