n-hexadecyl 4-methoxycinnamate | 125628-87-7

• 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: n-hexadecyl 4-methoxycinnamate
• 英文别名: palmityl 4-methoxycinnamate；Hexadecyl 3-(4-methoxyphenyl)prop-2-enoate
• CAS: 125628-87-7
• 化学式: C₂₆H₄₂O₃
• 分子量: 402.618
• InChiKey: ROFQZXOTPNHKQU-UHFFFAOYSA-N

物化性质

• 熔点：
  57-58 °C(Solv: hexane (110-54-3))
• 沸点：
  512.5±25.0 °C(Predicted)
• 密度：
  0.954±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  29
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-十六烷醇 、 4-甲氧基肉桂酸 在 Novozym 435 作用下， 80.0 ℃ 、80.0 kPa 条件下， 生成 n-hexadecyl 4-methoxycinnamate
  参考文献：
  名称：

  Solvent-free Lipase-Catalyzed Preparation of Long-Chain Alkyl Phenylpropanoates and Phenylpropyl Alkanoates

  摘要：

  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.

  DOI：

  10.1021/jf060052t

文献信息

• Treatment of Collagen gene related diseases by inhibition of natural antisense transcript to a collagen gene
  申请人：CuRNA, Inc.

  公开号：US10370657B2

  公开（公告）日：2019-08-06

  The present invention relates to antisense oligonucleotides that modulate the expression of and/or function of a Collagen gene, in particular, by targeting natural antisense polynucleotides of a Collagen gene. The invention also relates to the identification of these antisense oligonucleotides and their use in treating diseases and disorders associated with the expression of Collagen genes.

  本发明涉及调节胶原蛋白基因表达和/或功能的反义寡核苷酸，特别是通过靶向胶原蛋白基因的天然反义多核苷酸。本发明还涉及这些反义寡核苷酸的鉴定及其在治疗与胶原基因表达有关的疾病和失调中的用途。
• Abedi, Jaleh Azmi; Roscher, Nina Matheny, Synthetic Communications, 1989, vol. 19, # 9-10, p. 1539 - 1550
  作者：Abedi, Jaleh Azmi、Roscher, Nina Matheny

  DOI：——

  日期：——
• MISCHUNGEN AUS MIKROPIGMENTEN
  申请人：BASF SE

  公开号：EP1187598B1

  公开（公告）日：2009-10-21
• TREATMENT OF COLLAGEN GENE RELATED DISEASES BY INHIBITION OF NATURAL ANTISENSE TRANSCRIPT TO A COLLAGEN GENE
  申请人：CuRNA, Inc.

  公开号：US20170073680A1

  公开（公告）日：2017-03-16

  The present invention relates to antisense oligonucleotides that modulate the expression of and/or function of a Collagen gene, in particular, by targeting natural antisense polynucleotides of a Collagen gene. The invention also relates to the identification of these antisense oligonucleotides and their use in treating diseases and disorders associated with the expression of Collagen genes.
• 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.