(Z,E,E)-5-羟基-1,7-二(4-羟基苯基)-1,4,6-庚三烯-3-酮 | 52328-96-8

• 物质功能分类: 天然产物 - 酚类
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 中文名称: (Z,E,E)-5-羟基-1,7-二(4-羟基苯基)-1,4,6-庚三烯-3-酮
• 英文名称: bis-demethoxycurcumin
• 英文别名: bis(4-hydroxycinnamoyl)methane；(1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxyphenyl)hepta-1,4,6-trien-3-one
• CAS: 52328-96-8
• 化学式: C₁₉H₁₆O₄
• 分子量: 308.334
• InChiKey: YXAKCQIIROBKOP-HSSGTREWSA-N

物化性质

• 沸点：
  553.4±50.0 °C(Predicted)
• 密度：
  1.319±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z,E,E)-5-羟基-1,7-二(4-羟基苯基)-1,4,6-庚三烯-3-酮 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 2.0h， 以65%的产率得到四氢双脱甲氧基二阿魏酰甲烷
  参考文献：
  名称：

  A comparative study on the antioxidant properties of tetrahydrocurcuminoids and curcuminoids

  摘要：

  Several curcuminoids and tetrahydrocurcuminoids (THCs), bearing various hydroxyl and/or methoxy groups on their benzene rings, have been synthesized to study their antioxidant and hydrogen donating capacities using the DPPH method at 25 degrees C in methanol. The results show that the tetrahydrocurcuminoids are in general much more efficient than their curcuminoid analogs if they include a phenol group in meta- or para-position of the linking chain and a neighboring phenol or methoxy group. This efficiency gain of THCs by comparison to curcuminoids was attributed to the presence of benzylic hydrogens involved in the oxidation process of these compounds and not to the beta-diketone moiety in the chain. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.085
• 作为产物：
  描述：

  乙酰丙酮 在 盐酸 、 boron trioxide 、 硼酸三丁酯 、 正丁胺 作用下， 生成 (Z,E,E)-5-羟基-1,7-二(4-羟基苯基)-1,4,6-庚三烯-3-酮
  参考文献：
  名称：

  A comparative study on the antioxidant properties of tetrahydrocurcuminoids and curcuminoids

  摘要：

  Several curcuminoids and tetrahydrocurcuminoids (THCs), bearing various hydroxyl and/or methoxy groups on their benzene rings, have been synthesized to study their antioxidant and hydrogen donating capacities using the DPPH method at 25 degrees C in methanol. The results show that the tetrahydrocurcuminoids are in general much more efficient than their curcuminoid analogs if they include a phenol group in meta- or para-position of the linking chain and a neighboring phenol or methoxy group. This efficiency gain of THCs by comparison to curcuminoids was attributed to the presence of benzylic hydrogens involved in the oxidation process of these compounds and not to the beta-diketone moiety in the chain. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.085

文献信息

• Curcuminoids Form Reactive Glucuronides In Vitro
  作者：Erika Pfeiffer、Simone I. Hoehle、Stephan G. Walch、Alexander Riess、Anikó M. Sólyom、Manfred Metzler

  DOI：10.1021/jf0623283

  日期：2007.1.1

  the glucuronic acid moiety at the alcoholic hydroxyl group was formed from the same curcuminoids, but not hexahydro-curcuminoids, by human microsomes. Curcuminoids without a phenolic hydroxyl group gave rise to the aliphatic glucuronide only. The phenolic glucuronides of curcuminoids, but not of hexahydro-curcuminoids, were rather lipophilic and, in part, unstable in aqueous solution, their stability

  由于姜黄素具有抗炎，抗癌和抗阿尔茨海默氏病的活性，因此备受关注，但对其药代动力学和代谢命运知之甚少。因此，目前已经对姜黄素及其主要的I相代谢产物六氢姜黄素以及各种天然和人工类似物的葡糖醛酸苷化进行了体外研究。根据LC-MS / MS分析，由大鼠和人类肝脏微粒体由姜黄素，六氢姜黄素和其他具有酚羟基的类似物产生的主要葡萄糖醛酸苷为酚醛酸葡萄糖苷。然而，由人微粒体由相同的姜黄素而不是六氢姜黄素形成了在醇羟基上带有葡糖醛酸部分的第二葡糖醛酸。没有酚羟基的姜黄素仅产生脂族葡糖醛酸。姜黄素类的酚类葡糖醛酸而不是六氢姜黄素类的酚类葡糖醛酸具有相当的亲脂性，并且在水溶液中部分不稳定，其稳定性在很大程度上取决于芳族取代基的类型。姜黄素及其天然同源物的酚醛葡萄糖醛酸苷，而不是母体化合物，明显抑制了无细胞条件下微管蛋白的组装，暗示了葡糖醛酸苷的化学反应性。姜黄素主要II期代谢产物的这些新颖性质值得进一步研究。它
• Mechanochemical synthesis of 2,2-difluoro-4, 6-bis(β-styryl)-1,3,2-dioxaborines and their use in cyanide ion sensing
  作者：Daisy R. Sherin、Sherin G. Thomas、Kallikat N. Rajasekharan

  DOI：10.1515/hc-2015-0096

  日期：2015.12.1

  The conversion of arylaldehydes to 1,7-diaryl-5-hydroxyhepta-1,4,6-trien-3-ones (curcuminoids) and the mechanochemical cyclization of these products to 2,2-difluoro-4,6-bis(β-styryl)-1,3,2-dioxaborines using BF₃-Et₂O are described. Investigation of the cyanide ion sensing ability of the 2,2-difluoro-4,6-bis(β-styryl)-1,3,2-dioxaborines, in relation to the substituent groups on the aryl ring, showed that a hydroxy susbstituent is required, preferably para to the intervening carbon bridge.

  摘要：将芳基醛转化为1,7-二芳基-5-羟基庚烷-1,4,6-三烯-3-酮（姜黄素类化合物），并描述了利用BF₃-Et₂O进行这些产物的机械化学环化反应，制备2,2-二氟-4,6-双(β-苯乙烯基)-1,3,2-二氧硼杂环。研究了2,2-二氟-4,6-双(β-苯乙烯基)-1,3,2-二氧硼杂环对氰离子的感应能力，发现与芳基环上的取代基团相关，需要一个羟基取代基，最好是位于介入碳桥的para位置。
• 一种人工合成姜黄素及其衍生物的方法
  申请人：杭州瑞树生化有限公司

  公开号：CN106748705B

  公开（公告）日：2020-05-05

  本发明公开一种人工合成姜黄素及其衍生物的方法。该方法以乙酰丙酮钙为乙酰丙酮供源，经与相应的苯甲醛衍生物进行克莱森‑施密特酯缩合反应并在脱水剂硼酸三正丁酯催化下脱水后得到产物中间体(Ⅰ)姜黄素钙盐；然后中间体(Ⅰ)经一锅法水解得粗品，粗品提纯后得到最终产物姜黄素及其衍生物。与乙酰丙酮硼酸络合物法相比，本发明使用乙酰丙酮钙可以使得反应过程中乙酰丙酮基活性位点更为精确、活化，从而减少副产物的生成，提高姜黄素及其衍生物的产率。
• Versatility of the Curcumin Scaffold: Discovery of Potent and Balanced Dual BACE-1 and GSK-3β Inhibitors
  作者：Rita Maria Concetta Di Martino、Angela De Simone、Vincenza Andrisano、Paola Bisignano、Alessandra Bisi、Silvia Gobbi、Angela Rampa、Romana Fato、Christian Bergamini、Daniel I. Perez、Ana Martinez、Giovanni Bottegoni、Andrea Cavalli、Federica Belluti

  DOI：10.1021/acs.jmedchem.5b00894

  日期：2016.1.28

  multifactorial maladies such as Alzheimer’s disease (AD). The concurrent inhibition of the validated AD targets β-secretase (BACE-1) and glycogen synthase kinase-3β (GSK-3β) by attacking both β-amyloid and tau protein cascades has been identified as a promising AD therapeutic strategy. In our study, curcumin was identified as a lead compound for the simultaneous inhibition of both targets; therefore, synthetic

  作为解决诸如阿尔茨海默氏病（AD）等复杂和多因素疾病的有用工具，多目标方法已得到越来越多的接受。通过攻击β-淀粉样蛋白和tau蛋白级联反应，同时抑制经过验证的AD靶标β-分泌酶（BACE-1）和糖原合酶激酶-3β（GSK-3β）被认为是一种有前途的AD治疗策略。在我们的研究中，姜黄素被确定为同时抑制两个靶点的先导化合物。因此，合成努力致力于获得一个新的基于姜黄素的类似物的小图书馆，并获得了许多有效和平衡的双靶标抑制剂。特别地，2，6，和7作为具有神经保护潜力和脑通透性的有前途的候选药物出现的。值得注意的是，对于一些新的化合物的对称二酮和β酮-烯醇互变异构形式被有意分离并测试在体外，使我们深入了解用于BACE-1和GSK-3β抑制的关键要求。
• COMPOUNDS AND MATRICES FOR USE IN BONE GROWTH AND REPAIR
  申请人：HUMAN BIOMOLECULAR RESEARCH INSTITUTE

  公开号：US20160038641A1

  公开（公告）日：2016-02-11

  Compositions of small molecules, matrices, and isolated cells including methods of preparation, and methods for differentiation, transdifferentiation, and proliferation of animal cells into the osteoblast blast cell lineage were described. Examples of osteogenic materials that were administered to cells or co-cultured with cells are represented by compounds of Formula II, IV, and VI independently or preferably in combination with a matrix to afford bone cells. Small molecule-stimulated cells were also combined with a matrix, placed with a cellular adhesive or material carrier and implanted to a site in an animal for bone repair. Matrix pretreated with compounds of Formula II, IV, and VI were also used to cause cells to migrate to the matrix that is of use for therapeutic purposes.

  描述了由小分子、基质和孤立细胞组成的组合物，包括制备方法，以及动物细胞分化、转分化和增殖成骨母细胞谱系的方法。给细胞施加的或与细胞共培养的成骨材料的示例由独立或首选与基质组合的Formula II、IV和VI化合物代表。受小分子刺激的细胞还与基质结合，与细胞粘合剂或材料载体一起植入到动物体内的部位进行骨修复。预先用Formula II、IV和VI化合物处理的基质也被用于导致细胞迁移到用于治疗目的的基质上。

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