4-(heptyloxy)-3,5-dihydroxybenzoic acid methyl ester | 147825-66-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(heptyloxy)-3,5-dihydroxybenzoic acid methyl ester
• 英文别名: Methyl 4-heptoxy-3,5-dihydroxybenzoate
• CAS: 147825-66-9
• 化学式: C₁₅H₂₂O₅
• 分子量: 282.337
• InChiKey: IAINIACQFDIDDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(heptyloxy)-3,5-dihydroxybenzoic acid methyl ester 在 palladium on activated charcoal 吡啶 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 氯化亚砜 、 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 22.33h， 生成 5-Dimethylaminomethyl-2-heptyloxy-benzene-1,3-diol
  参考文献：
  名称：

  Benzylamine antioxidants: relationship between structure, peroxyl radical scavenging, lipid peroxidation inhibition and cytoprotection

  摘要：

  Three homologous series of 3,5-dialkoxy-4-hydroxybenzylamines were prepared and tested (1) as peroxyl radical scavengers in homogeneous aqueous solution, (2) as inhibitors of iron-dependent peroxidation of rabbit brain vesicular membrane lipids, and (3) as cytoprotective agents using primary cultures of rat hippocampal neurons exposed to hydrogen peroxide. The structural requirements for efficient radical trapping in homogeneous solution differed from those for effective lipid peroxidation inhibition: In homogeneous solution a kinetic preference existed for smaller, less sterically encumbered substituents flanking the reactive phenolic hydroxyl group. Lipid peroxidation inhibition, on the other hand, required longer more lipophilic substituents. Consequently, a lipophilic alkoxyl substituent at C3 and a small substituent at C5 appeared optimal for efficient radical scavenging activity in both lipid and homogeneous solution. Maximal cytoprotection of rat hippocampal neurons exposed to hydrogen peroxide was also associated with more lipophilic derivatives although substituent length and substituent bulk may represent independent parameters for relating structure and efficacy in this system.

  DOI：

  10.1021/jm00061a018
• 作为产物：
  描述：

  1-碘庚烷 、 没食子酸甲酯 在 sodium hydride 作用下， 生成 4-(heptyloxy)-3,5-dihydroxybenzoic acid methyl ester
  参考文献：
  名称：

  Benzylamine antioxidants: relationship between structure, peroxyl radical scavenging, lipid peroxidation inhibition and cytoprotection

  摘要：

  Three homologous series of 3,5-dialkoxy-4-hydroxybenzylamines were prepared and tested (1) as peroxyl radical scavengers in homogeneous aqueous solution, (2) as inhibitors of iron-dependent peroxidation of rabbit brain vesicular membrane lipids, and (3) as cytoprotective agents using primary cultures of rat hippocampal neurons exposed to hydrogen peroxide. The structural requirements for efficient radical trapping in homogeneous solution differed from those for effective lipid peroxidation inhibition: In homogeneous solution a kinetic preference existed for smaller, less sterically encumbered substituents flanking the reactive phenolic hydroxyl group. Lipid peroxidation inhibition, on the other hand, required longer more lipophilic substituents. Consequently, a lipophilic alkoxyl substituent at C3 and a small substituent at C5 appeared optimal for efficient radical scavenging activity in both lipid and homogeneous solution. Maximal cytoprotection of rat hippocampal neurons exposed to hydrogen peroxide was also associated with more lipophilic derivatives although substituent length and substituent bulk may represent independent parameters for relating structure and efficacy in this system.

  DOI：

  10.1021/jm00061a018