geranyl levulinate

• 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: geranyl levulinate
• 英文别名: Geranyl levulinate；[(2E)-3,7-dimethylocta-2,6-dienyl] 4-oxopentanoate
• 化学式: C₁₅H₂₄O₃
• 分子量: 252.354
• InChiKey: LYZVOWORCQDZCM-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  香叶醇 、 乙酰丙酸 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 生成 geranyl levulinate
  参考文献：
  名称：

  Formation of 4-Alkoxy-.gamma.-valerolactones from Levulinic Acid and Alcohols during Storage at Room Temperature

  摘要：

  Levulinic acid (LA) is a flavor ingredient used for many products. During the storage of LA in alcohols at room temperature, chemical changes were observed. Specifically, two groups of compounds were formed, esters of LA and 4-alkoxy-gamma-valerolactones. All of these compounds were identified by spectral data and synthesis. Mechanistically, it is proposed that the alcohol reacts reversibly either with the keto group of LA to form 4-alkoxy-gamma-valerolactone via a hemiketal intermediate or with the acid group of LA to form the ester. All of the data obtained from this study suggest that during the initial stages of storage the reactions are kinetically controlled to form the 4-alkoxy-gamma-valerolactone more than the ester; however, as the reactions proceed toward equilibrium, they become thermodynamically controlled to form the ester more than the 4-alkoxy-gamma-valerolactone.

  DOI：

  10.1021/jf00051a041

文献信息

• Formation of 4-Alkoxy-.gamma.-valerolactones from Levulinic Acid and Alcohols during Storage at Room Temperature
  作者：Chi-Kuen Shu、Brian M. Lawrence

  DOI：10.1021/jf00051a041

  日期：1995.3

  Levulinic acid (LA) is a flavor ingredient used for many products. During the storage of LA in alcohols at room temperature, chemical changes were observed. Specifically, two groups of compounds were formed, esters of LA and 4-alkoxy-gamma-valerolactones. All of these compounds were identified by spectral data and synthesis. Mechanistically, it is proposed that the alcohol reacts reversibly either with the keto group of LA to form 4-alkoxy-gamma-valerolactone via a hemiketal intermediate or with the acid group of LA to form the ester. All of the data obtained from this study suggest that during the initial stages of storage the reactions are kinetically controlled to form the 4-alkoxy-gamma-valerolactone more than the ester; however, as the reactions proceed toward equilibrium, they become thermodynamically controlled to form the ester more than the 4-alkoxy-gamma-valerolactone.