Phenol, 2,6-bis[(2E)-3,7-dimethyl-2,6-octadienyl]-4-iodo- | 641614-03-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Phenol, 2,6-bis[(2E)-3,7-dimethyl-2,6-octadienyl]-4-iodo-
• 英文别名: (2'E,2''E)-4-iodo-2-(3',7'-dimethylocta-2',6'-dienyl)-6-(3'',7''-dimethylocta-2'',6''-dienyl)phenol；2,6-di[(2E)-3,7-dimethyl-2,6-octadienyl]-4-iodophenol
• CAS: 641614-03-1
• 化学式: C₂₆H₃₇IO
• 分子量: 492.484
• InChiKey: NSKITLCETANCEJ-JFMUQQRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.47
• 重原子数：
  28.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  Phenol, 2,6-bis[(2E)-3,7-dimethyl-2,6-octadienyl]-4-iodo- 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)-3,5-di[(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
• 作为产物：
  描述：

  香叶基溴 、 4-碘苯酚 在 sodium hydroxide 作用下， 以26%的产率得到Phenol, 2,6-bis[(2E)-3,7-dimethyl-2,6-octadienyl]-4-iodo-
  参考文献：
  名称：

  Myrsinoic Acid E, an Anti-inflammatory Compound fromMyrsine seguinii

  摘要：

  Myrsine seguinii 的甲醇提取物产生了新型消炎化合物 myrsinoic acid E（1），其结构被阐明为 3,5-二茂烷基-4-羟基苯甲酸。我们合成了 1-及其 3,5-二丙烯基（2）和 3,5-二呋喃基类似物（3）。在剂量为 1.4 μmol 时，化合物 1-3 对 12-O- 十四碳酰樟脑酚-13-乙酸酯（TPA）诱发的小鼠耳朵炎症的抑制率分别为 59%、14% 和 69%。

  DOI：

  10.1271/bbb.67.2038