monoethyl 3-hydroxy-3-n-pentadecylglutarate | 95249-39-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: monoethyl 3-hydroxy-3-n-pentadecylglutarate
• 英文别名: 3-Hydroxy-3-pentadecyl-pentanedioic acid monoethyl ester；3-(2-ethoxy-2-oxoethyl)-3-hydroxyoctadecanoic acid
• CAS: 95249-39-1
• 化学式: C₂₂H₄₂O₅
• 分子量: 386.572
• InChiKey: DTOFHRLUBVJPQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  27
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  棕榈酸乙酯 在 吡啶 、 硫酸 、 双氧水 、 乙酸酐 、 臭氧 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 、 苯 为溶剂， 反应 38.0h， 生成 monoethyl 3-hydroxy-3-n-pentadecylglutarate
  参考文献：
  名称：

  3-Alkyl-3-hydroxyglutaric Acids: A New Class of Hypocholesterolemic HMG CoA Reductase Inhibitors. 1

  摘要：

  Derivatives of 3-hydroxy-3-methylglutaric acid (HMG), a portion of the substrate for HMG CoA reductase, were prepared and tested for their inhibitory action against rat liver HMG CoA reductase and for their hypocholesterolemic activity. Structure-dependent competitive inhibition was observed. Optimal structures had a free dicarboxylic acid with an alkyl group of 13-16 carbons at position 3. 3-n-Pentadecyl-3-hydroxyglutaric acid (3j) (IC50 = 50 microM) reduced serum cholesterol in the Triton-treated rat and HMG CoA reductase activity in the 20,25-diazacholesterol-treated rat.

  DOI：

  10.1021/jm50001a011

文献信息

• 3-Alkyl-3-hydroxyglutaric Acids: A New Class of Hypocholesterolemic HMG CoA Reductase Inhibitors. 1
  作者：John S. Baran、Ivar Laos、Donna D. Langford、James E. Miller、Charlene Jett、Beatrice Taite、Elaine Rohrbacher

  DOI：10.1021/jm50001a011

  日期：1985.5

  Derivatives of 3-hydroxy-3-methylglutaric acid (HMG), a portion of the substrate for HMG CoA reductase, were prepared and tested for their inhibitory action against rat liver HMG CoA reductase and for their hypocholesterolemic activity. Structure-dependent competitive inhibition was observed. Optimal structures had a free dicarboxylic acid with an alkyl group of 13-16 carbons at position 3. 3-n-Pentadecyl-3-hydroxyglutaric acid (3j) (IC50 = 50 microM) reduced serum cholesterol in the Triton-treated rat and HMG CoA reductase activity in the 20,25-diazacholesterol-treated rat.