(9Z,12Z)-N-dodecyloctadeca-9,12-dienamide

• 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: (9Z,12Z)-N-dodecyloctadeca-9,12-dienamide
• 英文别名: (9z,12z)-N-dodecyloctadeca-9,12-dienamide
• 化学式: C₃₀H₅₇NO
• 分子量: 447.789
• InChiKey: UHJBZQUZDZOLAO-BIXSNLIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.9
• 重原子数：
  32
• 可旋转键数：
  25
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  十二烷基伯胺 、 亚油酸乙酯 在 Candida antarctica lipase B 作用下， 以 neat (no solvent) 为溶剂， 65.0 ℃ 、5.0 kPa 条件下， 反应 20.0h， 以100%的产率得到(9Z,12Z)-N-dodecyloctadeca-9,12-dienamide
  参考文献：
  名称：

  Aminolysis of linoleic and salicylic acid derivatives with Candida antarctica lipase B: A solvent-free process to obtain amphiphilic amides for cosmetic application

  摘要：

  In this biotechnological process, the fatty amides (9Z,12Z)-N-dodecyloctadeca-9,12-dienamide (3) and N-dodecy1-2-hydroxybenzamide (5), respectively derived from linoleic acid and salicylic acid were synthesized through aminolysis reactions catalyzed by Candida antarctica lipase B. These amphiphilic compounds receive great attention from cosmetic industry due to a range of beneficial properties for skin. The aminolysis reactions were performed with the esters ethyl linoleate (1) and ethyl salicylate (4) as acyl group donors and the fatty compound N-dodecylamine (2) as the nucleophilic substrate. The aminolysis reactions were carried out in a solvent-free process, which is beneficial from an environmental and economical perspective, at 65 degrees C and reduced pressure (50 mbar). Parameters as enzyme amount and substrates molar ratios were investigated and the products were monitored by HPLC analysis. The conversion rates were measured through disappearance of ethyl linoleate and ethyl salicylate. The best conversion rates (up to 95%) were obtained by adding an enzyme amount of 5.0 g/mol of acyl donor group substrate and an equimolar substrates ratio (1:1). The products characterization was performed by High Resolution Mass Spectrometry, Infrared spectroscopy and Nuclear Magnetic Ressonance. This work reveals that enzymatic synthesis provides an attractive way for the cosmetic industrial production of fatty amides, which may represent key ingredients to maintain and/or restore a healthy skin. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2016.01.002

文献信息

• Epoxidation of carbon-carbon double bond with membrane bound peroxygenase
  申请人：——

  公开号：US20030040090A1

  公开（公告）日：2003-02-27

  A method has been discovered for the epoxidation of a compound having at least one carbon-carbon double bond, the method involves reacting a compound having at least one carbon-carbon double bond, a solvent, an oxidant, and membrane bound peroxygenase. Also discovered is a method for preparing the membrane bound peroxygenase involving grinding seeds containing peroxygenase to produce ground seeds, homogenizing the ground seeds in a buffer to form a slurry, centrifuging the slurry to produce a first supernatant, centrifuging the first supernatant to produce a second supernatant, and filtering said second supernatant through a protein-binding membrane filter to produce membrane bound peroxygenase; optionally the second supernatant is filtered through a hydrophilic membrane filter prior to filtering the second supernatant through a protein-binding membrane filter.

  发现了一种使具有至少一个碳碳双键的化合物发生环氧化反应的方法，该方法包括使具有至少一个碳碳双键的化合物、溶剂、氧化剂和膜结合过氧酶发生反应。还发现了一种制备膜结合过氧化氢酶的方法，包括研磨含有过氧化氢酶的种子以产生磨碎的种子，在缓冲液中均质磨碎的种子以形成浆液，离心浆液以产生第一上清液，离心第一上清液以产生第二上清液，通过蛋白质结合膜过滤器过滤所述第二上清液以产生膜结合过氧化氢酶；在通过蛋白质结合膜过滤器过滤第二上清液之前，可选择通过亲水膜过滤器过滤第二上清液。
• US6485949B1
  申请人：——

  公开号：US6485949B1

  公开（公告）日：2002-11-26
• US6852315B2
  申请人：——

  公开号：US6852315B2

  公开（公告）日：2005-02-08
• Aminolysis of linoleic and salicylic acid derivatives with Candida antarctica lipase B: A solvent-free process to obtain amphiphilic amides for cosmetic application
  作者：Ana Maria Mouad、Delphine Taupin、Laurent Lehr、Florent Yvergnaux、André Luiz Meleiro Porto

  DOI：10.1016/j.molcatb.2016.01.002

  日期：2016.4

  In this biotechnological process, the fatty amides (9Z,12Z)-N-dodecyloctadeca-9,12-dienamide (3) and N-dodecy1-2-hydroxybenzamide (5), respectively derived from linoleic acid and salicylic acid were synthesized through aminolysis reactions catalyzed by Candida antarctica lipase B. These amphiphilic compounds receive great attention from cosmetic industry due to a range of beneficial properties for skin. The aminolysis reactions were performed with the esters ethyl linoleate (1) and ethyl salicylate (4) as acyl group donors and the fatty compound N-dodecylamine (2) as the nucleophilic substrate. The aminolysis reactions were carried out in a solvent-free process, which is beneficial from an environmental and economical perspective, at 65 degrees C and reduced pressure (50 mbar). Parameters as enzyme amount and substrates molar ratios were investigated and the products were monitored by HPLC analysis. The conversion rates were measured through disappearance of ethyl linoleate and ethyl salicylate. The best conversion rates (up to 95%) were obtained by adding an enzyme amount of 5.0 g/mol of acyl donor group substrate and an equimolar substrates ratio (1:1). The products characterization was performed by High Resolution Mass Spectrometry, Infrared spectroscopy and Nuclear Magnetic Ressonance. This work reveals that enzymatic synthesis provides an attractive way for the cosmetic industrial production of fatty amides, which may represent key ingredients to maintain and/or restore a healthy skin. (C) 2016 Elsevier B.V. All rights reserved.