p-coumaric acid octadecyl ester | 72943-88-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: p-coumaric acid octadecyl ester
• 英文别名: octadecyl 4-hydroxycinnamate；octadecyl-p-coumarate；octadecyl coumarate；Octadecyl 3-(4-hydroxyphenyl)prop-2-enoate
• CAS: 72943-88-5
• 化学式: C₂₇H₄₄O₃
• 分子量: 416.645
• InChiKey: SXXOKKBSVARFFB-UHFFFAOYSA-N

物化性质

• 熔点：
  84-87 °C
• 沸点：
  529.5±25.0 °C(Predicted)
• 密度：
  0.970±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.7
• 重原子数：
  30
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 储存条件：
  室温

反应信息

• 作为产物：
  描述：

  硬脂醇 、 对羟基肉桂酸 在 硫酸 作用下， 以 四氢呋喃 为溶剂， 生成 p-coumaric acid octadecyl ester
  参考文献：
  名称：

  Antioxidant Properties and Efficacies of Synthesized Alkyl Caffeates, Ferulates, and Coumarates

  摘要：

  Caffeic, ferulic, and coumaric acids were lipophilized with saturated fatty alcohols (C1-C20). The antioxidant properties of these hydroxycinnamic acids and their alkyl esters were evaluated in various assays. Furthermore, the antioxidant efficiency of the compounds was evaluated in a simple o/w microemulsion using the conjugated autoxidizable triene (CAT) assay. All evaluated phenolipids had radical scavenging, reducing power, and metal chelating properties. Only caffeic acid and caffeates were able to form a complex with iron via their catechol group in the phenolic ring. In the o/w emulsion, the medium chain phenolipids of the three homologues series were most efficient. The antioxidant properties and efficacies were dependent upon functional groups substituted to the ring structure and were in the following order: caffeic acid and caffeates > ferulic acid and ferulates > coumaric acid and coumarates. Moreover, the results demonstrated that the test system has an impact on the antioxidative properties measured.

  DOI：

  10.1021/jf500588s

文献信息

• [EN] COMPOSITIONS FOR TOPICAL DELIVERY OF A PHARMACEUTICALLY ACTIVE AGENT HAVING REDUCED OXIDATION<br/>[FR] COMPOSITIONS A OXYDATION REDUITE UTILISEES POUR L'ADMINISTRATION LOCALE D'UN AGENT ACTIF SUR LE PLAN PHARMACEUTIQUE
  申请人：PROCTER & GAMBLE

  公开号：WO2001060337A1

  公开（公告）日：2001-08-23

  The present invention relates to compositions for the topical delivery of at least one pharmaceutically active agent comprising from about 1% to about 50% by weight of at least one phospholipid, from about 0.01% to about 10% of at least one pharmaceutically active agent, from about 0.01% to about 0.5% by weight of at least one chelating agent, and at least one suitable carrier material selected from components used in compositions for topical application. The at least one chelating agent prevents or reduces the oxidation of the topical compositions of the present invention.
• [EN] COMPOSITIONS FOR TOPICAL DELIVERY OF A PHARMACEUTICALLY ACTIVE AGENT HAVING REDUCED SKIN IRRITATION<br/>[FR] COMPOSITIONS REDUISANT L'IRRITATION CUTANEE UTILISEES POUR L'ADMINISTRATION LOCALE D'UN AGENT ACTIF SUR LE PLAN PHARMACEUTIQUE
  申请人：PROCTER & GAMBLE

  公开号：WO2001060336A1

  公开（公告）日：2001-08-23

  The present invention relates to compositions for the topical delivery of at least one pharmaceutically active agent comprising from about 1 % to about 50 % by weight of at least one phospholipid and from about 0.1 % to about 50 % by weight of at least one skin conditioning agent. The at least one skin conditioning agent prevents or reduces the drying, irritation, and/or itching of the skin of animals and/or humans caused by the continuous or repetitive application of topical compositions to the skin of animals and/or humans, which contain high levels of phospholipids.
• Antioxidant Properties and Efficacies of Synthesized Alkyl Caffeates, Ferulates, and Coumarates
  作者：Ann-Dorit Moltke Sørensen、Erwann Durand、Mickaël Laguerre、Christelle Bayrasy、Jérôme Lecomte、Pierre Villeneuve、Charlotte Jacobsen

  DOI：10.1021/jf500588s

  日期：2014.12.31

  Caffeic, ferulic, and coumaric acids were lipophilized with saturated fatty alcohols (C1-C20). The antioxidant properties of these hydroxycinnamic acids and their alkyl esters were evaluated in various assays. Furthermore, the antioxidant efficiency of the compounds was evaluated in a simple o/w microemulsion using the conjugated autoxidizable triene (CAT) assay. All evaluated phenolipids had radical scavenging, reducing power, and metal chelating properties. Only caffeic acid and caffeates were able to form a complex with iron via their catechol group in the phenolic ring. In the o/w emulsion, the medium chain phenolipids of the three homologues series were most efficient. The antioxidant properties and efficacies were dependent upon functional groups substituted to the ring structure and were in the following order: caffeic acid and caffeates > ferulic acid and ferulates > coumaric acid and coumarates. Moreover, the results demonstrated that the test system has an impact on the antioxidative properties measured.