methyl 5-(4-Acetoxy-3,5-dimethoxyphenyl)-penta-2E,4E-dienoate | 878800-16-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: methyl 5-(4-Acetoxy-3,5-dimethoxyphenyl)-penta-2E,4E-dienoate
• 英文别名: methyl (2E,4E)-5-(4-acetyloxy-3,5-dimethoxyphenyl)penta-2,4-dienoate
• CAS: 878800-16-9
• 化学式: C₁₆H₁₈O₆
• 分子量: 306.315
• InChiKey: KZTJGABUIJQIMS-KQQUZDAGSA-N

物化性质

• 沸点：
  412.9±45.0 °C(Predicted)
• 密度：
  1.166±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 5-(4-Acetoxy-3,5-dimethoxyphenyl)-penta-2E,4E-dienoate 在 sodium hydroxide 作用下， 以95%的产率得到(2E,4E)-5-(4-hydroxy-3,5-dimethoxyphenyl)penta-2,4-dienoic acid
  参考文献：
  名称：

  An effective strategy to develop active cinnamic acid-directed antioxidants based on elongating the conjugated chains

  摘要：

  To optimize antioxidant activity and lipophilicity of cinnamic acid derivatives (CAs) including ferulic acid, sinapic acid, 3,4-dimethoxycinnamic acid, and p-hydroxycinnamic acid, four analogs bearing an additional double bond between their aromatic ring and propenoic acid moiety were designed and synthesized based on the conjugated chain elongation strategy. The antioxidant performance of the CAs were investigated by 2,2'-diphenyl-1-picrylhydrazyl (DPPH.)-scavenging, ferric reducing/antioxidant power, cyclic voltammetry, DNA strand breakage-inhibiting and anti-haemolysis activity assays. It was found that CAs with elongation of conjugated chains display increased DPPH.-scavenging, DNA strand breakage-inhibiting and anti-haemolysis activities as compared to their parent molecules, due to their improved hydrogen atom-donating ability and lipophilicity. Overall, this work highlights an effective strategy to develop potential CA-directed antioxidants by elongating their conjugated chain. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.foodchem.2014.02.092
• 作为产物：
  描述：

  丁香醛 在 吡啶 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 methyl 5-(4-Acetoxy-3,5-dimethoxyphenyl)-penta-2E,4E-dienoate
  参考文献：
  名称：

  An effective strategy to develop active cinnamic acid-directed antioxidants based on elongating the conjugated chains

  摘要：

  To optimize antioxidant activity and lipophilicity of cinnamic acid derivatives (CAs) including ferulic acid, sinapic acid, 3,4-dimethoxycinnamic acid, and p-hydroxycinnamic acid, four analogs bearing an additional double bond between their aromatic ring and propenoic acid moiety were designed and synthesized based on the conjugated chain elongation strategy. The antioxidant performance of the CAs were investigated by 2,2'-diphenyl-1-picrylhydrazyl (DPPH.)-scavenging, ferric reducing/antioxidant power, cyclic voltammetry, DNA strand breakage-inhibiting and anti-haemolysis activity assays. It was found that CAs with elongation of conjugated chains display increased DPPH.-scavenging, DNA strand breakage-inhibiting and anti-haemolysis activities as compared to their parent molecules, due to their improved hydrogen atom-donating ability and lipophilicity. Overall, this work highlights an effective strategy to develop potential CA-directed antioxidants by elongating their conjugated chain. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.foodchem.2014.02.092

文献信息

• Novel compounds useful for modulating abnormal cell proliferation
  申请人：Roifman Chaim

  公开号：US20060058554A1

  公开（公告）日：2006-03-16

  There is described compounds of Formula I, and salts, solvates and hydrates thereof: wherein: R 1 , R 2 and R 3 are each independently selected from OH, C 1-6 alkyl, OC 1-6 alkyl, OC(O)C 1-6 alkyl, C(O)OC 1-6 alkyl, NH 2 , NH-C 1-6 alkyl, N(C 1-6 alkyl)(C 1-6 alkyl), C(O)NHC 1-6 alkyl, C(O)N(C 1-6 alkyl)(C 1-6 alkyl), SH, SC 1-6 alkyl, NO 2 , CF 3 , OCF 3 and halogen; and Ar is an aromatic or heteroaromatic group chosen from benzene, naphthalene, quinoline, isoquinoline, indole, pyridine, pyrasine, pyrimidine, imidazole, furan and thiophene, unsubstituted or substituted with 1-4 substituents independently selected from OH, C 1-6 alkyl, C 1-6 alkoxy, C 1-3 alkylenedioxy, NH 2 , NH-C 1-6 alkyl, N(C 1-6 alkyl)(C 1-6 alkyl), SH, S-C 1-6 alkyl, NO 2 , CF 3 , OCF 3 and halogen. The compounds of Formula I are useful: in therapeutic methods and compositions for modulating cell proliferation, in diagnostic assays and as research tools.

  描述了化合物I的结构，以及其盐、溶剂合物和水合物：其中：R1、R2和R3分别独立地选择自OH、C1-6烷基、OC1-6烷基、OC(O)C1-6烷基、C(O)OC1-6烷基、NH2、NH-C1-6烷基、N(C1-6烷基)(C1-6烷基)、C(O)NHC1-6烷基、C(O)N(C1-6烷基)(C1-6烷基)、SH、SC1-6烷基、NO2、CF3、O 和卤素；Ar是从苯、萘、喹啉、异喹啉、吲哚、吡啶、吡啉、嘧啶、咪唑、呋喃和噻吩中选择的芳香或杂环芳基，未取代或取代有1-4个取代基，独立地选择自OH、C1-6烷基、C1-6烷氧基、C1-3烷基二氧基、NH2、NH-C1-6烷基、N(C1-6烷基)(C1-6烷基)、SH、S-C1-6烷基、 、 、O 和卤素。化合物I的结构在治疗方法和组合物中用于调节细胞增殖，在诊断分析和研究工具中有用。
• NOVEL COMPOUNDS USEFUL FOR MODULATING ABNORMAL CELL PROLIFERATION
  申请人：THE HOSPITAL FOR SICK CHILDREN

  公开号：EP1807386A1

  公开（公告）日：2007-07-18
• EP1807386A4
  申请人：——

  公开号：EP1807386A4

  公开（公告）日：2008-09-17
• US7202383B2
  申请人：——

  公开号：US7202383B2

  公开（公告）日：2007-04-10
• US7407989B2
  申请人：——

  公开号：US7407989B2

  公开（公告）日：2008-08-05