oleyl dihydrocaffeate

• 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: oleyl dihydrocaffeate
• 英文别名: Oleyl dihydrocaffeate；[(Z)-octadec-9-enyl] 3-(3,4-dihydroxyphenyl)propanoate
• 化学式: C₂₇H₄₄O₄
• 分子量: 432.644
• InChiKey: GMPMIAVWZLJQNX-KTKRTIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  31
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  油醇 、 甲基3-(3,4-二羟基苯基)丙酸酯 在 Novozym 435 lipase from Candida antarctica 作用下， 80.0 ℃ 、80.0 kPa 条件下， 反应 72.0h， 生成 oleyl dihydrocaffeate
  参考文献：
  名称：

  Highly Efficient Preparation of Lipophilic Hydroxycinnamates by Solvent-free Lipase-Catalyzed Transesterification

  摘要：

  Various medium- or long-chain alkyl cinnamates and hydroxycinnamates, including oleyl p-coumarate as well as palmityl and oleyl ferulates, were prepared in high yield by lipase-catalyzed transesterification of an equimolar mixture of a short-chain alkyl cinnamate and a fatty alcohol such as lauryl, palmityl, and oleyl alcohol under partial vacuum at moderate temperature in the absence of solvents and drying agents in direct contact with the reaction mixture. Immobilized lipase B from Candida antarctica was the most effective biocatalyst for the various transesterification reactions. Transesterification activity of this enzyme was up to 56-fold higher than esterification activity for the preparation of medium- and long-chain alkyl ferulates. The relative transesterification activities found for C. antarctica lipase were of the following order: hydrocinnamate > cinnamate > 4- hydroxyhydrocinnamate > 3-methoxycinnamate > 2-methoxycinnamate approximate to 4-methoxycinnamate approximate to 3-hydroxycinnamate > hydrocaffeate approximate to 4-hydroxycinnamate > ferulate > 2-hydroxycinnamate > caffeate approximate to sinapate. With respect to the position of the hydroxy substituents at the phenyl moiety, the transesterification activity of C. antarctica lipase B increased in the order meta > para > ortho. The immobilized lipases from Rhizomucor miehei and Thermomyces lanuginosus demonstrated moderate and low transesterification activity, respectively. Compounds with inverse chemical structure, that is, 3-phenylpropyl alkanoates such as 3-(4-hydroxyphenyl) propyl oleate and 3-(3,4- dimethoxyphenyl) propyl oleate, were obtained by C. antarctica lipase-catalyzed transesterification of fatty acid methyl esters with the corresponding 3- phenylpropan-1-ols in high yield, as well.

  DOI：

  10.1021/jf0611973

文献信息

• New sustainable biocatalytic approach for producing lipophilic (hydroxy)cinnamic esters based on deep eutectic mixtures
  作者：Susana Nieto、Francisco Martinez-Mora、Inmaculada Lozano、Francisco J. Ruiz、Rocio Villa、Pedro Lozano

  DOI：10.1016/j.cattod.2023.114500

  日期：2024.4

  The biocatalytic acylation of HCAs with fatty alcohols (FAs) is a suitable strategy to facilitate their incorporation to hydrophobic matrices ( cosmetic creams), although this modification is hampered by the immiscibility between both substrates. This work demonstrates the excellent suitability of deep eutectic mixtures to afford the clean biocatalytic synthesis of natural hydrophobic esters derived

  羟基肉桂酸 (HCA) 是天然存在的化合物，因其有助于健康的生物活性而受到高度重视。 HCA 与脂肪醇 (FA) 的生物催化酰化是促进其掺入疏水性基质（美容霜）的合适策略，尽管这种修饰因两种底物之间的不混溶性而受到阻碍。这项工作证明了低共熔混合物具有出色的适用性，可以清洁生物催化合成源自肉桂酸、香豆酸、咖啡酸和氢咖啡酸以及不同脂肪族化合物（1-己醇、1-十二醇、顺式9-十八烯醇）的天然疏水酯。和萜烯（香叶醇、β-香茅醇）醇在无溶剂条件下。通过低共熔混合物技术，两种底物以 1:8 HCA:FA 摩尔比实现轻松共溶，无需添加助剂/溶剂。这些均匀混合物被证明是 Novozym 435 催化的酯化过程（70 °C 下 8-96 小时）的优异反应介质，在大多数情况下，产品收率接近 100%（对于氢咖啡酸的情况：9-十八烯-1-醇混合物），根据 DPPH 测定保留其抗氧化活性。通过这种方法，合成过程的
• Solvent-free Lipase-Catalyzed Preparation of Long-Chain Alkyl Phenylpropanoates and Phenylpropyl Alkanoates
  作者：Klaus Vosmann、Petra Weitkamp、Nikolaus Weber

  DOI：10.1021/jf060052t

  日期：2006.4.1

  An enzymatic method was developed for the preparation of medium- or long-chain alkyl 3-phenylpropenoates (alkyl cinnamates), particularly alkyl hydroxy- and methoxy-substituted cinnamates such as oleyl p-coumarate and oleyl ferulate. The various alkyl cinnamates were formed in high to moderate yield by lipase-catalyzed esterification of cinnamic acid and its analogues with fatty alcohols in vacuo at moderate temperatures in the absence of drying agents and solvents. Immobilized Candida antarctica lipase B was the most effective biocatalyst for the various esterification reactions. The relative esterification activities were of the following order: clihydrocinnamic > cinnamic > 3-methoxycinnamic > dihydrocaffeic approximate to 3-hydroxycinnamic > 4-methoxycinnamic > 2-methoxycinnamic > 4-hydroxycinnamic > ferulic approximate to 3,4-dimethoxycinnamic > 2-hydroxycinnamic acid. With respect to the position of the substituents at the phenyl moiety, the esterification activity increased in the order meta > para > ortho. Rhizomucor miehei lipase demonstrated moderate esterification activity. Compounds with inverse chemical structure, that is, 3-phenylpropyl alkanoates such as 3-(4-hydroxyphenyl)propyl oleate, were also obtained in high yield by esterification of fatty acids with the corresponding 3-phenylpropan-1-ols.
• Highly Efficient Preparation of Lipophilic Hydroxycinnamates by Solvent-free Lipase-Catalyzed Transesterification
  作者：Petra Weitkamp、Klaus Vosmann、Nikolaus Weber

  DOI：10.1021/jf0611973

  日期：2006.9.1

  Various medium- or long-chain alkyl cinnamates and hydroxycinnamates, including oleyl p-coumarate as well as palmityl and oleyl ferulates, were prepared in high yield by lipase-catalyzed transesterification of an equimolar mixture of a short-chain alkyl cinnamate and a fatty alcohol such as lauryl, palmityl, and oleyl alcohol under partial vacuum at moderate temperature in the absence of solvents and drying agents in direct contact with the reaction mixture. Immobilized lipase B from Candida antarctica was the most effective biocatalyst for the various transesterification reactions. Transesterification activity of this enzyme was up to 56-fold higher than esterification activity for the preparation of medium- and long-chain alkyl ferulates. The relative transesterification activities found for C. antarctica lipase were of the following order: hydrocinnamate > cinnamate > 4- hydroxyhydrocinnamate > 3-methoxycinnamate > 2-methoxycinnamate approximate to 4-methoxycinnamate approximate to 3-hydroxycinnamate > hydrocaffeate approximate to 4-hydroxycinnamate > ferulate > 2-hydroxycinnamate > caffeate approximate to sinapate. With respect to the position of the hydroxy substituents at the phenyl moiety, the transesterification activity of C. antarctica lipase B increased in the order meta > para > ortho. The immobilized lipases from Rhizomucor miehei and Thermomyces lanuginosus demonstrated moderate and low transesterification activity, respectively. Compounds with inverse chemical structure, that is, 3-phenylpropyl alkanoates such as 3-(4-hydroxyphenyl) propyl oleate and 3-(3,4- dimethoxyphenyl) propyl oleate, were obtained by C. antarctica lipase-catalyzed transesterification of fatty acid methyl esters with the corresponding 3- phenylpropan-1-ols in high yield, as well.