3-羟基-3-十五烷基戊烷二酸 | 52939-64-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 3-羟基-3-十五烷基戊烷二酸
• 英文名称: 3-n-pentadecyl-3-hydroxyglutaric acid
• 英文别名: 3-Hydroxy-3-pentadecylpentanedioic acid
• CAS: 52939-64-7
• 化学式: C₂₀H₃₈O₅
• 分子量: 358.519
• InChiKey: XIMVZSLUNQIRJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  25
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2918199090

反应信息

• 作为反应物：
  描述：

  3-羟基-3-十五烷基戊烷二酸 在 chromium(VI) oxide 、 lithium aluminium tetrahydride 、 硫酸 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 16.0h， 生成 3,5-dihydroxy-3-n-pentadecylvaleric acid lactol
  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
• 作为产物：
  描述：

  棕榈酸乙酯 在 硫酸 、 双氧水 、 臭氧 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 4.0h， 生成 3-羟基-3-十五烷基戊烷二酸
  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

• Pentanedioic acid derivatives
  申请人：G.D. Searle & Co.

  公开号：EP0089674B1

  公开（公告）日：1985-12-27
• HMG-COA SECONDARY METABOLITES AND USES THEREOF
  申请人：Pappan Kirk

  公开号：US20120121554A1

  公开（公告）日：2012-05-17

  The present invention is directed, among other things, to using secondary metabolites in the mevalonate pathway (such as, for example, HMG) and/or structurally related compounds to mediate biological activities (e.g., for therapeutic applications) and/or as diagnostic agents. In some embodiments, the biological activities comprise one or more pleiotropic effects of statins (such as, for example, angiogenesis, promoting vascular function, anti-inflammatory action, immunomodulation, etc.). Also provided are methods of screening for mevalonate pathway secondary metabolites, methods of producing HMG, and methods of diagnosing comprising measuring amount of mevalonate pathway secondary metabolites.
• 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.