3-geranyl-2-hydroxybenzoic acid | 1580490-62-5

• 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: 3-geranyl-2-hydroxybenzoic acid
• 英文别名: Geranyl hydroxybenzoic acid；3-[(2E)-3,7-dimethylocta-2,6-dienyl]-2-hydroxybenzoic acid
• CAS: 1580490-62-5
• 化学式: C₁₇H₂₂O₃
• 分子量: 274.36
• InChiKey: ASNTWOYHNWXDDP-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,6-二溴苯酚 在 叔丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 9.16h， 生成 3-geranyl-2-hydroxybenzoic acid
  参考文献：
  名称：

  Synthesis and antibacterial evaluation of 3-Farnesyl-2-hydroxybenzoic acid from Piper multiplinervium

  摘要：

  3-Famesyl-2-hydroxybenzoic acid is an antibacterial agent isolated from the leaves of Piper multiplinervium. This compound has activity against both Gram positive and Gram negative bacteria including Escherichia coli, Staphylococcus aureus and Helicobacter pylori. This research aimed to synthesize a natural antibacterial compound and its analogs. The synthesis of 3-Famesyl-2-hydroxybenzoic acid consists of three steps: straightforward synthesis involving protection of phenolic hydroxyl group, coupling of suitable isoprenyl chain to the protected aromatic ring at ortho position followed by carboxylation with concomitant deprotection to give the derivatives of the salicylic acid. All the three prenylated compounds synthesized were found to exhibit spectrum of activity against S. aureus (ATCC) having MIC: 5.84 x 10(-3), 41.46 x 10(-2) and 6.19 x 10(-1) mu mol/ml respectively. The compounds also displayed activity against resistance strain of S. aureus (SA1119B) having MIC: 5.84 x 10(-3), 7.29 x 10(-3) and 3.09 x 10(-1) mu mol/ml respectively. This synthesis has been achieved and accomplished with the confirmation of it structure to that of the original natural product, thus producing the first synthesis of the natural product and providing the first synthesis of its analogs with 3-Farnesyl-2-hydroxybenzoic acid having biological activity higher than that of the original natural product. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.fitote.2014.01.005

文献信息

• Synthesis and antibacterial evaluation of 3-Farnesyl-2-hydroxybenzoic acid from Piper multiplinervium
  作者：Ibrahim Malami、Simon Gibbons、John P. Malkinson

  DOI：10.1016/j.fitote.2014.01.005

  日期：2014.3

  3-Famesyl-2-hydroxybenzoic acid is an antibacterial agent isolated from the leaves of Piper multiplinervium. This compound has activity against both Gram positive and Gram negative bacteria including Escherichia coli, Staphylococcus aureus and Helicobacter pylori. This research aimed to synthesize a natural antibacterial compound and its analogs. The synthesis of 3-Famesyl-2-hydroxybenzoic acid consists of three steps: straightforward synthesis involving protection of phenolic hydroxyl group, coupling of suitable isoprenyl chain to the protected aromatic ring at ortho position followed by carboxylation with concomitant deprotection to give the derivatives of the salicylic acid. All the three prenylated compounds synthesized were found to exhibit spectrum of activity against S. aureus (ATCC) having MIC: 5.84 x 10(-3), 41.46 x 10(-2) and 6.19 x 10(-1) mu mol/ml respectively. The compounds also displayed activity against resistance strain of S. aureus (SA1119B) having MIC: 5.84 x 10(-3), 7.29 x 10(-3) and 3.09 x 10(-1) mu mol/ml respectively. This synthesis has been achieved and accomplished with the confirmation of it structure to that of the original natural product, thus producing the first synthesis of the natural product and providing the first synthesis of its analogs with 3-Farnesyl-2-hydroxybenzoic acid having biological activity higher than that of the original natural product. (C) 2014 Elsevier B.V. All rights reserved.