4-羟基-5-氧代己酸乙酯 | 105469-26-9

• 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: 4-羟基-5-氧代己酸乙酯
• 英文名称: ethyl 4-hydroxy-5-oxo-hexanoate
• 英文别名: Hexanoic acid, 4-hydroxy-5-oxo-, ethyl ester；ethyl 4-hydroxy-5-oxohexanoate
• CAS: 105469-26-9
• 化学式: C₈H₁₄O₄
• 分子量: 174.197
• InChiKey: NCMWEHNWCPHXTR-UHFFFAOYSA-N

物化性质

• LogP：
  0.400 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氧代丁酸乙基酯 、 sodium pyruvate 在 citrate buffer 、 pyruvate decarboxylase 、 焦磷酸硫胺素 、 magnesium sulfate 作用下， 以 水 为溶剂， 反应 72.0h， 以4%的产率得到4-羟基-5-氧代己酸乙酯
  参考文献：
  名称：

  Rationalizing the Origin of Solerone (5-Oxo-4-hexanolide):  Biomimetic Synthesis and Identification of Key Metabolites in Sherry Wine

  摘要：

  A biomimetic synthesis of solerone (5-oxo-4-hexanolide, 1) using both enzymatic and acid-catalyzed reactions was performed. Starting from L-glutamic acid 5-ethyl ester (2) enzymatic oxidative deamination followed by subsequent decarboxylation of the corresponding 2-oxoglutaric acid Ei-ethyl ester (3) led to ethyl 4-oxobutanoate (4). In the presence of pyruvate, 4 served as key substrate for a novel acyloin condensation catalyzed by pyruvate decarboxylase (EC 4.1.1.1) from Saccharomyces cerevisiae. Finally, the resulting ethyl 4-hydroxy-5-oxo-hexanoate (5) was easily converted into solerone (1) in the presence of acid. The acyloin condensation of 3 with acetaldehyde to ethyl 5-hydroxy-4-oxohexanoate (6) revealed an alternative route to solerone (1). Acid-catalyzed lactonization of 6 produced 4-oxo-5-hexanolide (7) as well as 5 and 1 via keto-enol tautomerization. Confirming the relevance of the proposed biogenetic pathway, the solerone precursors 2-6 as well as delta-lactone 7 were identified in sherry by GC/MS analysis for the first time.

  DOI：

  10.1021/jf960316j

文献信息

• Rationalizing the Origin of Solerone (5-Oxo-4-hexanolide):  Biomimetic Synthesis and Identification of Key Metabolites in Sherry Wine
  作者：Dietmar Häring、Peter Schreier、Markus Herderich

  DOI：10.1021/jf960316j

  日期：1997.2.1

  A biomimetic synthesis of solerone (5-oxo-4-hexanolide, 1) using both enzymatic and acid-catalyzed reactions was performed. Starting from L-glutamic acid 5-ethyl ester (2) enzymatic oxidative deamination followed by subsequent decarboxylation of the corresponding 2-oxoglutaric acid Ei-ethyl ester (3) led to ethyl 4-oxobutanoate (4). In the presence of pyruvate, 4 served as key substrate for a novel acyloin condensation catalyzed by pyruvate decarboxylase (EC 4.1.1.1) from Saccharomyces cerevisiae. Finally, the resulting ethyl 4-hydroxy-5-oxo-hexanoate (5) was easily converted into solerone (1) in the presence of acid. The acyloin condensation of 3 with acetaldehyde to ethyl 5-hydroxy-4-oxohexanoate (6) revealed an alternative route to solerone (1). Acid-catalyzed lactonization of 6 produced 4-oxo-5-hexanolide (7) as well as 5 and 1 via keto-enol tautomerization. Confirming the relevance of the proposed biogenetic pathway, the solerone precursors 2-6 as well as delta-lactone 7 were identified in sherry by GC/MS analysis for the first time.