1-(6-Hydroxy-2,3,4-trimethoxy-phenyl)-tetradecan-1-one | 134081-74-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(6-Hydroxy-2,3,4-trimethoxy-phenyl)-tetradecan-1-one
• 英文别名: 1-(6-Hydroxy-2,3,4-trimethoxyphenyl)-1-tetradecanone；1-(6-hydroxy-2,3,4-trimethoxyphenyl)tetradecan-1-one
• CAS: 134081-74-6
• 化学式: C₂₃H₃₈O₅
• 分子量: 394.552
• InChiKey: LNMRPHXDMOVXDC-UHFFFAOYSA-N

物化性质

• 熔点：
  52.5-54.0 °C(Solv: methanol (67-56-1))
• 沸点：
  513.8±45.0 °C(Predicted)
• 密度：
  1.012±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  28
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(6-Hydroxy-2,3,4-trimethoxy-phenyl)-tetradecan-1-one 在 氢氧化钾 、 aluminum tri-bromide 、 potassium-<3,4-bis-benzyloxy benzoate> 作用下， 以 乙腈 为溶剂， 反应 9.0h， 生成 2-(3,4-Bis-benzyloxy-phenyl)-3-dodecyl-5-hydroxy-6,7-dimethoxy-chromen-4-one
  参考文献：
  名称：

  Syntheses of 5,7,8- and 5,6,7-trioxygenated 3-alkyl-3',4'-dihydroxyflavones and their inhibitory activities against arachidonate 5-lipoxygenase

  摘要：

  5,6,7- and 5,7,8-Trioxygenated 3',4'-dihydroxyflavones were derivatized by introducing alkyl groups of various chain lengths at the 3-position of the flavone skeleton. These compounds were tested as inhibitors for arachidonate 5-lipoxygenase purified from porcine leukocytes. Modification of the 3-position with an alkyl group of 6-10 carbons markedly decreased the IC50 values. 3-Hexyl-3',4'-dihydroxy-5,7,8-trimethoxyflavone inhibited 5-lipoxygenase with an IC50 value of 58 nM. The platelet and leukocyte 12-lipoxygenases, 15-lipoxygenase of reticulocytes, and cyclooxygenase of vesicular gland were inhibited less potently (IC50 = 0.4, 0.4, 2.7, and 30-mu-M). Thus, the compound was a relatively selective inhibitor for 5-lipoxygenase.

  DOI：

  10.1021/jm00111a037
• 作为产物：
  描述：

  1-(6-Benzyloxy-2-hydroxy-3,4-dimethoxy-phenyl)-tetradecan-1-one 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 甲醇 、 乙酸乙酯 、 丙酮 为溶剂， 生成 1-(6-Hydroxy-2,3,4-trimethoxy-phenyl)-tetradecan-1-one
  参考文献：
  名称：

  Syntheses of 5,7,8- and 5,6,7-trioxygenated 3-alkyl-3',4'-dihydroxyflavones and their inhibitory activities against arachidonate 5-lipoxygenase

  摘要：

  5,6,7- and 5,7,8-Trioxygenated 3',4'-dihydroxyflavones were derivatized by introducing alkyl groups of various chain lengths at the 3-position of the flavone skeleton. These compounds were tested as inhibitors for arachidonate 5-lipoxygenase purified from porcine leukocytes. Modification of the 3-position with an alkyl group of 6-10 carbons markedly decreased the IC50 values. 3-Hexyl-3',4'-dihydroxy-5,7,8-trimethoxyflavone inhibited 5-lipoxygenase with an IC50 value of 58 nM. The platelet and leukocyte 12-lipoxygenases, 15-lipoxygenase of reticulocytes, and cyclooxygenase of vesicular gland were inhibited less potently (IC50 = 0.4, 0.4, 2.7, and 30-mu-M). Thus, the compound was a relatively selective inhibitor for 5-lipoxygenase.

  DOI：

  10.1021/jm00111a037

文献信息

• HORIE, TOKUNARU;TOMINAGA, HIDEAKI;KAWAMURA, YASUHIKO;HADA, TAKAHIKO;UEDA,+, J. MED. CHEM., 34,(1991) N, C. 2169-2176
  作者：HORIE, TOKUNARU、TOMINAGA, HIDEAKI、KAWAMURA, YASUHIKO、HADA, TAKAHIKO、UEDA,+

  DOI：——

  日期：——