trans-geranic acid N-ethylamide

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: trans-geranic acid N-ethylamide
• 英文别名: (2E)-N-ethyl-3,7-dimethyl-2,6-octadienamide；(2E)-N-ethyl-3,7-dimethylocta-2,6-dienamide
• 化学式: C₁₂H₂₁NO
• 分子量: 195.305
• InChiKey: PSALGEPOYXQWKJ-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 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：

  geranic acid N-hydroxysuccinimide ester 、 乙胺盐酸盐 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 0.33h， 生成 trans-geranic acid N-ethylamide 、 cis-geranic acid N-ethylamide
  参考文献：
  名称：

  Identification of Geranic Acid, a Tyrosinase Inhibitor in Lemongrass (Cymbopogon citratus)

  摘要：

  Lemongrass is a popular Asian herb having a lemon-like flavor. Very recently, potent tyrosinase inhibitory activity has been found in lemongrass in addition to various biological activities reported in the literature. The aim of the present study is to identify the active compounds in the lemongrass. An assay-guided purification revealed that one-of the active substances was geranic acid. Geranic acid has two stereoisomers, which are responsible for the trans and cis geometry on the conjugated double bond. Both isomers are present in the active ethyl acetate-soluble extract of the lemongrass, and their IC50 values were calculated to be 0.14 and 2.3 mM, respectively. The structure requirement of geranic acid for the potent tyrosinase inhibitory activity was investigated using geranic acid-related compounds.

  DOI：

  10.1021/jf072893l

文献信息

• ALKYLDIENAMIDES EXHIBITING TASTE AND SENSORY EFFECT IN FLAVOR COMPOSITIONS
  申请人：Dewis Mark L.

  公开号：US20090311402A1

  公开（公告）日：2009-12-17

  Alkyldienamides compounds suitable for use as flavoring agents are disclosed. The compounds are used as flavors since they possess umami characteristics or other desirable organoleptic properties. The disclosed compounds are defined by the structure set forth below: wherein R is ethyl or cyclopropyl; and wherein R′ is methyl or butyl, with the proviso that when R is ethyl, R′ is not methyl.

  本发明公开了适用于作为调味剂的烷基二烯酰胺化合物。这些化合物用作调味剂，因为它们具有鲜味特性或其他理想的感官特性。所公开的化合物由以下结构定义：其中R为乙基或环丙基；R'为甲基或丁基，但当R为乙基时，R'不为甲基。
• Unsaturated N-alkamides exhibiting taste and flavor enhancement effect in flavor compositions
  申请人：International Flavors & Fragrances Inc.

  公开号：EP2348014B1

  公开（公告）日：2017-05-10
• US7632531B2
  申请人：——

  公开号：US7632531B2

  公开（公告）日：2009-12-15
• US8075937B2
  申请人：——

  公开号：US8075937B2

  公开（公告）日：2011-12-13
• [DE] ANTIMIKROBIELL WIRKSAME ZUBEREITUNGEN<br/>[EN] ANTIMICROBIAL ACTIVE PREPARATIONS<br/>[FR] PREPARATIONS A ACTIVITE ANTIMICROBIENNE
  申请人：ANDRE RIEKS LABOR FUER ENZYMTE

  公开号：WO2005012210A2

  公开（公告）日：2005-02-10

  Die vorliegende Erfindung betrifft die Verwendung von Perillasäure, Geraniumsäure, Citronellsäure und Derivaten der Geraniumsäure, der Citronellsäure, des Geraniols und des Citronellols als antimikrobielle Wirkstoffe gegen Bakterien, Hefen und/oder Schimmelpilze, nachfolgend Mikroorganismen genannt. Insbesondere betrifft die vorliegenden Erfindung die Verwendung der genannten antimikrobiellen Wirkstoffe zur Herstellung von kosmetischen oder pharmazeutischen Zubereitungen, sowie von Nahrungs- und Futtermittel-Zusammensetzungen. Bei den antimikrobiellen Wirkstoffen handelt es sich um natürliche Monoterpene und Derivate ihrer Oxidationsprodukte.