methyl (E)-3-[4-(acetyloxy)-3-[(2E)-3,7-dimethyl-2,6-octadienyl]phenyl]-2-propenoate | 908373-08-0

• 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: methyl (E)-3-[4-(acetyloxy)-3-[(2E)-3,7-dimethyl-2,6-octadienyl]phenyl]-2-propenoate
• CAS: 908373-08-0
• 化学式: C₂₂H₂₈O₄
• 分子量: 356.462
• InChiKey: VYMWKRUZMIHRRH-PHZVMYRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.03
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl (E)-3-[4-(acetyloxy)-3-[(2E)-3,7-dimethyl-2,6-octadienyl]phenyl]-2-propenoate 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以89%的产率得到(E)-3-[3-[(2E)-3,7-dimethylocta-2,6-dienyl]-4-hydroxyphenyl]prop-2-enoic acid
  参考文献：
  名称：

  Artepillin C isoprenomics: Design and synthesis of artepillin C isoprene analogues as lipid peroxidation inhibitor having low mitochondrial toxicity

  摘要：

  We designed and synthesized isoprene analogues of artepillin C, a major component of Brazilian propolis, and investigated the inhibitory activity on lipid peroxidation of rat liver mitochondria (RLM) and RLM toxicity based on isoprenomics. We succeeded in the synthesis of artepillin C isoprene analogues using regioselective prenylation within the range from 22% to 53% total yield. Reactivity of artepillin C and its isoprene analogues with ABTS (2,2'-Azinobis(3-ethylbenzothiazoline-6-sulfonate)) radical cations showed only a slight difference among the molecules. The isoprene side-chain elongation analogues of artepillin C showed almost the same inhibitory activity against RLM lipid peroxidation as artepillin C. Artepillin C and its isoprene analogues had very weak RLM uncoupling activity. Moreover, artepillin C and its isoprene analogues exhibited a lower inhibitory activity against adenosine 5'-triphosphate (ATP) synthesis by about two orders of magnitude than the effective inhibitory activity against RLM lipid peroxidation. From these results we conclude that artepillin C isoprene analogues could be potent lipid peroxidation inhibitors having low mitochondrial toxicity. We also conclude that elongation of the isoprene side chain of artepillin C to increase lipophilicity had little influence on the inhibitory activity toward RLM lipid peroxidation. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.04.015
• 作为产物：
  描述：

  (E)-2-(3,7-dimethylocta-2,6-dien-1-yl)-4-iodophenol 在 palladium diacetate 4-二甲氨基吡啶 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 24.0h， 生成 methyl (E)-3-[4-(acetyloxy)-3-[(2E)-3,7-dimethyl-2,6-octadienyl]phenyl]-2-propenoate
  参考文献：
  名称：

  Artepillin C isoprenomics: Design and synthesis of artepillin C isoprene analogues as lipid peroxidation inhibitor having low mitochondrial toxicity

  摘要：

  We designed and synthesized isoprene analogues of artepillin C, a major component of Brazilian propolis, and investigated the inhibitory activity on lipid peroxidation of rat liver mitochondria (RLM) and RLM toxicity based on isoprenomics. We succeeded in the synthesis of artepillin C isoprene analogues using regioselective prenylation within the range from 22% to 53% total yield. Reactivity of artepillin C and its isoprene analogues with ABTS (2,2'-Azinobis(3-ethylbenzothiazoline-6-sulfonate)) radical cations showed only a slight difference among the molecules. The isoprene side-chain elongation analogues of artepillin C showed almost the same inhibitory activity against RLM lipid peroxidation as artepillin C. Artepillin C and its isoprene analogues had very weak RLM uncoupling activity. Moreover, artepillin C and its isoprene analogues exhibited a lower inhibitory activity against adenosine 5'-triphosphate (ATP) synthesis by about two orders of magnitude than the effective inhibitory activity against RLM lipid peroxidation. From these results we conclude that artepillin C isoprene analogues could be potent lipid peroxidation inhibitors having low mitochondrial toxicity. We also conclude that elongation of the isoprene side chain of artepillin C to increase lipophilicity had little influence on the inhibitory activity toward RLM lipid peroxidation. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.04.015