2-methoxy-3,5,6-trimethyl-4-hydroxybenzoic acid | 148014-35-1

• 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: 2-methoxy-3,5,6-trimethyl-4-hydroxybenzoic acid
• 英文别名: 4-hydroxy-2-methoxy-3,5,6-trimethylbenzoic acid；3,5,6-Trimethyl-4-hydroxy-2-methoxybenzoic acid
• CAS: 148014-35-1
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: CFCNRJSLZDWEGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methoxy-3,5,6-trimethyl-4-hydroxybenzoic acid 在 正丁基锂 作用下， 以 乙酸乙酯 为溶剂， 反应 0.5h， 生成 Benzhydryl 4-[5-[3-(4-benzhydryloxycarbonyl-3-methoxy-2,5,6-trimethylphenoxy)carbonyl-4-methoxyphenoxy]-2-methoxybenzoyl]oxy-2-methoxy-3,5,6-trimethylbenzoate
  参考文献：
  名称：

  Synthesis and Phospholipase A₂ Inhibitory Activity of Thielocin B3 Derivatives

  摘要：

  We prepared several types of derivatives of thielocin B3, a very potent naturally occurring inhibitor for human nonpancreatic secretory PLA(2) (sPLA(2)-II), and conducted a structure-activity relationship study to identify potent sPLA(2)-II inhibitors with the aim of developing antiinflammatory drugs. The total number of aromatic rings is critical for sPLA(2)-II inhibition, and the best result was obtained in the case of six rings. The structure of the central part of the inhibitors was not specific, and potent inhibitors were found among the sulfide, sulfone, ether, methylene, and amino derivatives. Although a diester of the terminal carboxylic acid lost its inhibitory activity, having both of the carboxylic acids was not necessary for expression of activity, as illustrated by a glycine derivative with the benzyl ester group 36. Among the newly synthesized derivatives, 18, 20, 29, and 36 showed very potent human sPLA(2)-II inhibitory activity comparable to that of natural thielocin B3. Their IC50 values are in the range 0.069-0.14 mu M, and they are a class of compounds showing the most potent sPLA(2)-II inhibition to date.

  DOI：

  10.1021/jm960437a
• 作为产物：
  描述：

  4-Benzyloxy-2-methoxy-3,5,6-trimethyl-benzoic acid 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 以3.8 g的产率得到2-methoxy-3,5,6-trimethyl-4-hydroxybenzoic acid
  参考文献：
  名称：

  Synthesis and Phospholipase A₂ Inhibitory Activity of Thielocin B3 Derivatives

  摘要：

  We prepared several types of derivatives of thielocin B3, a very potent naturally occurring inhibitor for human nonpancreatic secretory PLA(2) (sPLA(2)-II), and conducted a structure-activity relationship study to identify potent sPLA(2)-II inhibitors with the aim of developing antiinflammatory drugs. The total number of aromatic rings is critical for sPLA(2)-II inhibition, and the best result was obtained in the case of six rings. The structure of the central part of the inhibitors was not specific, and potent inhibitors were found among the sulfide, sulfone, ether, methylene, and amino derivatives. Although a diester of the terminal carboxylic acid lost its inhibitory activity, having both of the carboxylic acids was not necessary for expression of activity, as illustrated by a glycine derivative with the benzyl ester group 36. Among the newly synthesized derivatives, 18, 20, 29, and 36 showed very potent human sPLA(2)-II inhibitory activity comparable to that of natural thielocin B3. Their IC50 values are in the range 0.069-0.14 mu M, and they are a class of compounds showing the most potent sPLA(2)-II inhibition to date.

  DOI：

  10.1021/jm960437a

文献信息

• Phytochemical Composition of Lichen Parmotrema hypoleucinum (J. Steiner) Hale from Algeria
  作者：Marwa Kerboua、Ali Ahmed Monia、Nsevolo Samba、Lúcia Silva、Cesar Raposo、David Díez、Jesus Miguel Rodilla

  DOI：10.3390/molecules27165229

  日期：——

  methyl esters of the predominant fatty acids in the lichen were identified: palmitic acid, linoleic acid, oleic acid and stearic acid; a hydrocarbon was also identified: 13-methyl-17-norkaur-15-ene and several derivatives of orsellinic acid. In the 1-Cires and 2-Cires fractions, the previous fatty acids were no longer observed, and only the derivatives of orsellinic acid were found. The analysis of the 1-Hexane

  在这项工作中，我们对在阿尔及利亚采集的两份 Parmotrema hypoleucinum地衣样品的己烷、氯仿和乙醇提取物的化学成分进行了研究。地衣P. hypoleucinum的每个样品都收集在两个不同的支持物上：Olea europaea和Quercus coccifera. 在 Soxhlet 中制备己烷提取物；每种己烷提取物根据其在甲醇中的溶解度进行分级；分离（冷）溶于甲醇的产物：1-己烷、2-己烷；不溶于甲醇的产品（冷）：1-Cires、2-Cires。用 GC-MS 分析了 1-Hexane、2-Hexane、1-Cires 和 2-Cires 的重氮甲烷酯化样品，其成分被鉴定为甲酯。在 1-己烷和 2-己烷馏分中，确定了地衣中主要脂肪酸的甲酯：棕榈酸、亚油酸、油酸和硬脂酸；还发现了一种碳氢化合物：13-methyl-17-norkaur-15-ene 和几种 orsellinic