2-(3-羟基苯基)乙基油酸酯 | 1037077-57-8

• 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: 2-(3-羟基苯基)乙基油酸酯
• 英文名称: 2-(3-hydroxyphenyl)ethyl oleate
• CAS: 1037077-57-8
• 化学式: C₂₆H₄₂O₃
• 分子量: 402.618
• InChiKey: WEEMJLNTBZTTQL-KTKRTIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.52
• 重原子数：
  29.0
• 可旋转键数：
  18.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  油酸甲酯 、 2-(3-羟基苯基)乙醇 在 Candida antarctica lipase B immobilized 作用下， 80.0 ℃ 、80.0 kPa 条件下， 生成 2-(3-羟基苯基)乙基油酸酯
  参考文献：
  名称：

  Lipophilic (Hydroxy)phenylacetates by Solvent-Free Lipase-Catalyzed Esterification and Transesterification in Vacuo

  摘要：

  Various long-chain alkyl (hydroxy)phenylacetates were prepared in high yield by lipase-catalyzed transesterification of the corresponding short-chain alkyl hydroxyphenyl acetates and fatty alcohols in equimolar ratios. The reactions were performed in vacuo at moderate temperatures in the absence of solvents and drying agents in direct contact with the reaction mixture. Immobilized lipase B from Candida antarctica(Novozym 435) was the most effective biocatalyst for the various transesterification reactions. Generally, Novozym 435-catalyzed transesterifications of short-chain alkyl (hydroxy)phenylacetates with long-chain alcohols led to higher conversions and enzyme activities than the corresponding esterifications. For example, the transesterification activity was up to 4-fold higher than the esterification activity for the formation of oleyl 4-hydroxy-3-methoxyphenylacetate using Novozym 435 as a biocatalyst. The relative transesterification activities were as follows: phenylacetate > 3-methoxyphenylacetate approximate to 4-methoxyphenylacetate > 4-hydroxy-3-methoxyphenylacetate > 3-hydroxyphenylacetate approximate to 4-hydroxyphenylacetate >> 2-methoxyphenylacetate >> 3,4-dihydroxyphenylacetate. With respect to the position of methoxy and hydroxy substituents, the transesterification activity of Novozym 435 decreased in the order meta approximate to para >> ortho. Compounds with inverse chemical structures, for example, tyrosyl oleate, were obtained by Novozym 435-catalyzed esterification and transesterification of fatty acids and their methyl esters, respectively, with 2-phenylethan-1-ols. In contrast to the transesterifications of short-chain alkyl (hydroxy)phenylacetates with fatty alcohols, higher conversions and enzyme activities were observed for the Novozym 435-catalyzed esterifications of (hydroxy)phenylethanols with long-chain fatty acids than the corresponding transesterifications with fatty acid methyl esters.

  DOI：

  10.1021/jf8002224