3-(4-hydroxyphenyl)propyl palmitate

• 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: 3-(4-hydroxyphenyl)propyl palmitate
• 英文别名: 3-(4-Hydroxyphenyl)propyl hexadecanoate
• 化学式: C₂₅H₄₂O₃
• 分子量: 390.607
• InChiKey: XJDWPLYPGSZWHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  28
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-hydroxyphenyl)propyl palmitate 在 2-碘酰基苯甲酸 、 sodium dithionite 作用下， 以 甲醇 、 水 为溶剂， 反应 1.08h， 生成 3-(3,4-dihydroxyphenyl)propyl palmitate
  参考文献：
  名称：

  Synthesis and Structure/Antioxidant Activity Relationship of Novel Catecholic Antioxidant Structural Analogues to Hydroxytyrosol and Its Lipophilic Esters

  摘要：

  A large panel of novel catecholic antioxidants and their fatty acid or methyl carbonate esters has been synthesized in satisfactory to good yields through a 2-iodoxybenzoic acid (IBX)-mediated aromatic hydroxylation as the key step. The new catechols are structural analogues of naturally occurring hydroxytyrosol (3,4-DHE). To evaluate structure/activity relationships, the antioxidant properties of all catecholic compounds were evaluated in vitro by ABTS assay and on whole cells by DCF fluorometric assay and compared with that of the corresponding already known hydroxytyrosyl derivatives. Results outline that all of the new catechols show antioxidant capacity in vitro higher than that of the corresponding hydroxytyrosyl derivatives. Less evident positive effects have been detected in whole cells experiments. Cytotoxicity experiments, using MTT assay, on a representative set of compounds evidenced no influence in cell survival.

  DOI：

  10.1021/jf301131a
• 作为产物：
  描述：

  棕榈酸甲酯 、 3-(4-羟基苯基)-1-丙醇 在 Novozym 435 lipase from Candida antarctica 作用下， 80.0 ℃ 、80.0 kPa 条件下， 反应 24.0h， 生成 3-(4-hydroxyphenyl)propyl palmitate
  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

• 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.
• Synthesis and Structure/Antioxidant Activity Relationship of Novel Catecholic Antioxidant Structural Analogues to Hydroxytyrosol and Its Lipophilic Esters
  作者：Roberta Bernini、Fernanda Crisante、Maurizio Barontini、Daniela Tofani、Valentina Balducci、Augusto Gambacorta

  DOI：10.1021/jf301131a

  日期：2012.8.1

  A large panel of novel catecholic antioxidants and their fatty acid or methyl carbonate esters has been synthesized in satisfactory to good yields through a 2-iodoxybenzoic acid (IBX)-mediated aromatic hydroxylation as the key step. The new catechols are structural analogues of naturally occurring hydroxytyrosol (3,4-DHE). To evaluate structure/activity relationships, the antioxidant properties of all catecholic compounds were evaluated in vitro by ABTS assay and on whole cells by DCF fluorometric assay and compared with that of the corresponding already known hydroxytyrosyl derivatives. Results outline that all of the new catechols show antioxidant capacity in vitro higher than that of the corresponding hydroxytyrosyl derivatives. Less evident positive effects have been detected in whole cells experiments. Cytotoxicity experiments, using MTT assay, on a representative set of compounds evidenced no influence in cell survival.