4-allyl-2-methoxyphenyl cinnamate | 532-08-1

• 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: 4-allyl-2-methoxyphenyl cinnamate
• 英文别名: cinnamic acid eugenyl ester；trans-cinnamic acid-(4-allyl-2-methoxy-phenyl ester)；trans-Zimtsaeure-(4-allyl-2-methoxy-phenylester)；Zimtsaeure-(2-methoxy-4-allyl-phenylester)；(2-methoxy-4-prop-2-enylphenyl) (E)-3-phenylprop-2-enoate
• CAS: 532-08-1
• 化学式: C₁₉H₁₈O₃
• 分子量: 294.35
• InChiKey: SJKFNIODBSUYID-ACCUITESSA-N

物化性质

• 沸点：
  452.0±44.0 °C(Predicted)
• 密度：
  1.113±0.06 g/cm3(Predicted)
• LogP：
  4.570

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2916399090

反应信息

• 作为产物：
  描述：

  4-allyl-2-methoxyphenyl bromoacetate 在 sodium hydroxide 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 20.0h， 生成 4-allyl-2-methoxyphenyl cinnamate
  参考文献：
  名称：

  Mall, Raghao S.; Papalkar, Abhijit S., Journal of Chemical Research, Miniprint, 2003, # 10, p. 1001 - 1013

  摘要：

  DOI：

文献信息

• 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。
• Antileishmanial Lead Structures from Nature: Analysis of Structure-Activity Relationships of a Compound Library Derived from Caffeic Acid Bornyl Ester
  作者：Jan Glaser、Martina Schultheis、Sudipta Hazra、Banasri Hazra、Heidrun Moll、Uta Schurigt、Ulrike Holzgrabe

  DOI：10.3390/molecules19021394

  日期：——

  Bioassay-guided fractionation of a chloroform extract of Valeriana wallichii (V. wallichii) rhizomes lead to the isolation and identification of caffeic acid bornyl ester (1) as the active component against Leishmania major (L. major) promastigotes (IC50 = 48.8 µM). To investigate the structure-activity relationship (SAR), a library of compounds based on 1 was synthesized and tested in vitro against L. major and L. donovani promastigotes, and L. major amastigotes. Cytotoxicity was determined using a murine J774.1 cell line and bone marrow derived macrophages (BMDM). Some compounds showed antileishmanial activity in the concentration range of pentamidine and miltefosine which are the standard drugs in use. In the L. major amastigote assay compounds 15, 19 and 20 showed good activity with relatively low cytotoxicity against BMDM, resulting in acceptable selectivity indices. Molecules with adjacent phenolic hydroxyl groups exhibited elevated cytotoxicity against murine cell lines J774.1 and BMDM. The Michael system seems not to be essential for antileishmanial activity. Based on the results compound 27 can be regarded as new lead structure for further structure optimization.

  在对 Valeriana wallichii (V. wallichii) 根茎的氯仿提取物进行生物测定引导的分馏时，成功分离并鉴定出咖啡酸伯基酯 (1)，作为对 Leishmania major (L. major) 萌发体的活性成分（IC50 = 48.8 µM）。为了研究结构-活性关系 (SAR)，基于化合物 1 合成了一系列化合物，并在体外测试了它们对 L. major 和 L. donovani 萌发体和 L. major 非芽孢体的活性。通过使用鼠类 J774.1 细胞系和骨髓来源的巨噬细胞 (BMDM) 测定了细胞毒性。一些化合物在与标准药物五氟苯和米氟喹范围内的浓度下表现出抗利什曼病活性。在 L. major 非芽孢体实验中，化合物 15、19 和 20 显示出良好的活性，同时对 BMDM 的细胞毒性相对较低，产生了可接受的选择性指数。相邻的酚羟基化合物对鼠类细胞系 J774.1 和 BMDM 显示出较高的细胞毒性。Michael 体系似乎对于抗利什曼病活性并不是必需的。根据结果，化合物 27 可被视为进一步结构优化的新型先导结构。
• PHOTOLABILE PRO-FRAGRANCES
  申请人：Henkel AG & Co. KGaA

  公开号：US20150099809A1

  公开（公告）日：2015-04-09

  Many fragrances that provide a scent of freshness tend to be highly volatile and are therefore not very economical when used in typical applications such as washing or cleaning processes, so they have to be used in relatively large quantities to be able to produce adequate effects. The disclosed photolabile pro-fragrances provide a much longer-lasting sense of fragrance, in particular with a scent of freshness, when used in typical applications, thus allowing said fragrances to be used efficiently.

  许多提供清新气味的香料往往具有高挥发性，因此在典型的应用中，如洗涤或清洁过程中使用时并不经济，因此必须使用相对大量的量才能产生足够的效果。所公开的光敏感前香料提供了更持久的香味感，特别是在典型的应用中具有清新的香味，从而使得这些香料能够有效地使用。
• Synthesis of cinnamic acid ester derivatives with antiproliferative and antimetastatic activities on murine melanoma cells
  作者：Juliana Alves do Vale、Michelle Peixoto Rodrigues、Ângela Maria Almeida Lima、Samira Soares Santiago、Graziela Domingues de Almeida Lima、Alisson Andrade Almeida、Leandro Licursi de Oliveira、Gustavo Costa Bressan、Róbson Ricardo Teixeira、Mariana Machado-Neves

  DOI：10.1016/j.biopha.2022.112689

  日期：2022.4

  Conventional treatments present severe side effects in cancer patients, and melanoma can be refractory to commonly used anticancer drugs, which justify the efforts to find new potential anti-melanoma drugs. An alternative to promote the discovery of new pharmacological substances would be modifying chemical groups from a bioactive compound. Here we describe the synthesis of seventeen compounds derived from

  黑色素瘤是最具侵袭性的皮肤癌，其发病率在过去几十年中持续上升。常规治疗对癌症患者存在严重的副作用，而黑色素瘤对常用的抗癌药物可能难以治愈，这证明了寻找新的潜在抗黑色素瘤药物的努力是合理的。促进发现新药理物质的另一种方法是修饰生物活性化合物的化学基团。在这里，我们描述了源自肉桂酸的 17 种化合物的合成及其对黑色素瘤细胞的生物活性评估。化合物 2,3-二溴-3-苯丙酸苯酯 ( 3q) 对鼠 B16-F10 细胞最有效，如在细胞毒性和细胞迁移测定中所观察到的。同时，该化合物对非肿瘤细胞表现出低细胞毒活性。在最高浓度下，化合物3q能够引发细胞凋亡，而在较低浓度下，它会影响细胞周期和黑色素瘤细胞增殖。此外，肉桂酸3q 会损害细胞侵袭、粘附、定植和肌动蛋白聚合。总之，这些结果突出了肉桂酸衍生物对黑色素瘤的抗增殖和抗转移潜力。
• Air freshening compositions, articles comprising same and methods
  申请人：The Procter & Gamble Company

  公开号：US20030024997A1

  公开（公告）日：2003-02-06

  An air freshening composition including porous carrier particles having a perfume composition entrapped therein, and a second component selected from an inert filer, hygroscopic agent, binder, coating material, moisture providing agent, and mixtures thereof. The composition may further comprise various optional components such as free perfumes, colorants, disintegrants, water swelling agents, porosity modifiers and mixtures thereof. A method for processing the compositions into a solid article includes the steps of entrapping a perfume in the porous carrier particles, heating and incorporating a carrier or binder material. The compositions may be further processed by optionally incorporating a powder inert filler and forming articles from the mixture. The articles may be formed from the compositions through prilling, extrusion, or compaction amongst other techniques. The air freshening articles and compositions will provide a sustained and controlled release of the perfume compositions over a long period of time without the use of a heat to activate the release. Articles of manufacture including the air freshening articles and various packaging are also disclosed.

  一种空气清新组合物，包括内含香水组合物的多孔载体颗粒，以及选自惰性过滤剂、吸湿剂、粘合剂、涂层材料、保湿剂及其混合物的第二种成分。组合物还可进一步包含各种可选成分，如游离香料、着色剂、崩解剂、水膨胀剂、孔隙度调节剂及其混合物。将组合物加工成固体物品的方法包括以下步骤：在多孔载体颗粒中夹带香水、加热和加入载体或粘合剂材料。组合物还可以通过加入粉末惰性填料进一步加工，并由混合物形成物品。除其他技术外，还可以通过挤压、挤出或压制等方法将混合物制成物品。这种空气清新剂制品和组合物可以在长时间内持续、可控地释放香水组合物，而无需使用热量来激活释放。此外，还公开了包括空气清新剂和各种包装在内的制造物品。