(5Z)-N-(2-hydroxy-2-methylpropyl)-dodec-5-enamide | 1116632-28-0

• 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: (5Z)-N-(2-hydroxy-2-methylpropyl)-dodec-5-enamide
• 英文别名: (Z)-N-(2-hydroxy-2-methylpropyl)dodec-5-enamide
• CAS: 1116632-28-0
• 化学式: C₁₆H₃₁NO₂
• 分子量: 269.428
• InChiKey: ZQNUNPUEOLDMCE-KTKRTIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  顺-5-十二碳烯酸 、 1-氨基-2-甲基-2-丙醇 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以57%的产率得到(5Z)-N-(2-hydroxy-2-methylpropyl)-dodec-5-enamide
  参考文献：
  名称：

  Synthesis and Evaluation of New Alkylamides Derived from α-Hydroxysanshool, the Pungent Molecule in Szechuan Pepper

  摘要：

  Szechuan pepper is widely used in Asia as a spice for its pleasant pungent and tingling sensations, produced by natural alkylamides called sanshools. alpha-Hydroxysanshool, the main alkylamide found in the pericarp of the fruit, stimulates sensory neurons innervating the mouth by targeting two chemosensitive members of the transient receptor potential (TRP) channels, TRPV1 and TRPA1. As it was previously found that configuration of the unsaturations in the alpha-hydroxysanshool alkyl chain is required for TRPA1 but not TRPV1 selectivity, this study aimed at obtaining more potent and selective TRPA1 agonists using alpha-hydroxysanshool as a starting material. This paper reports the preparation of new alkylamides derived from sanshool and their efficacy in stimulating TRPA1 and TRPV1 receptors. The data provide knowledge of the main sanshool chemical functionalities required for TRIP channel activation, but they also evidence new selective and potent TRPA1 agonists based on alpha-hydroxysanshool.

  DOI：

  10.1021/jf803067r

文献信息

• Acylamino acid compounds and food preparations containing same
  申请人：Nestec S.A.

  公开号：EP2140770A1

  公开（公告）日：2010-01-06

  An acylamino acid compound is described which can be used in food preparations to generate a savory tingling sensation without burning effect.

  介绍了一种酰基氨基酸化合物，它可用于食品制备，产生一种没有灼烧感的咸味刺痛感。
• ACYLAMINO ACID COMPOUNDS AND FOOD PREPARATIONS CONTAINING SAME
  申请人：Nestec S.A.

  公开号：EP2296492B1

  公开（公告）日：2017-01-18
• US9560876B2
  申请人：——

  公开号：US9560876B2

  公开（公告）日：2017-02-07
• [EN] ACYLAMINO ACID COMPOUNDS AND FOOD PREPARATIONS CONTAINING SAME<br/>[FR] COMPOSÉS D'ACIDE ACYLAMINÉ ET PRÉPARATIONS ALIMENTAIRES LES CONTENANT
  申请人：NESTEC SA

  公开号：WO2009141294A1

  公开（公告）日：2009-11-26

  An acylamino acid compound is described which can be used in food preparations to generate a savory tingling sensation without burning effect.
• Synthesis and Evaluation of New Alkylamides Derived from α-Hydroxysanshool, the Pungent Molecule in Szechuan Pepper
  作者：Candice Menozzi-Smarrito、Celine E. Riera、Caroline Munari、Johannes Le Coutre、Fabien Robert

  DOI：10.1021/jf803067r

  日期：2009.3.11

  Szechuan pepper is widely used in Asia as a spice for its pleasant pungent and tingling sensations, produced by natural alkylamides called sanshools. alpha-Hydroxysanshool, the main alkylamide found in the pericarp of the fruit, stimulates sensory neurons innervating the mouth by targeting two chemosensitive members of the transient receptor potential (TRP) channels, TRPV1 and TRPA1. As it was previously found that configuration of the unsaturations in the alpha-hydroxysanshool alkyl chain is required for TRPA1 but not TRPV1 selectivity, this study aimed at obtaining more potent and selective TRPA1 agonists using alpha-hydroxysanshool as a starting material. This paper reports the preparation of new alkylamides derived from sanshool and their efficacy in stimulating TRPA1 and TRPV1 receptors. The data provide knowledge of the main sanshool chemical functionalities required for TRIP channel activation, but they also evidence new selective and potent TRPA1 agonists based on alpha-hydroxysanshool.