N-(β-hydroxy-isobutyl)-lauramide | 83883-11-8

• 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-(β-hydroxy-isobutyl)-lauramide
• 英文别名: 1-Lauroylamino-2-methyl-propan-2-ol；N-(β-Hydroxy-isobutyl)-lauramid；Laurinsaeure-(β-hydroxy-isobutylamid)；N-(β-Hydroxy-isobutyl)-laurinamid；Octahydro-sanshoamid；N-(2-Hydroxy-2-methylpropyl)dodecanamide
• CAS: 83883-11-8
• 化学式: C₁₆H₃₃NO₂
• 分子量: 271.444
• InChiKey: DXRJDPYAUGGBPB-UHFFFAOYSA-N

物化性质

• 熔点：
  56-57 °C
• 沸点：
  426.2±28.0 °C(Predicted)
• 密度：
  0.916±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(β-hydroxy-isobutyl)-lauramide 在 platinum(IV) oxide 吡啶 、 氯化亚砜 、 氢气 作用下， 生成 N-isobutyl-dodecanamide
  参考文献：
  名称：

  不饱和脂肪酸酰胺在日本花椒属植物中的分布

  摘要：

  摘要 对日本7种花椒2个品种的不饱和脂肪酸酰胺进行了研究。除了已知的酰胺 α-sanshool、γ-sanshool 和羟基-γ-sanshool 之外，还通过化学和光谱证据分离并确定了一种新化合物羟基-α-sanshool。这些化合物对应于树皮中酰胺的羟基衍生物，通常存在于所有收集材料的果皮中。日本花椒属物种在化学分类上分为两个分类群。这些分类群与根据植物学分类分配的两个分类群不同。

  DOI：

  10.1016/0031-9422(82)80128-3
• 作为产物：
  描述：

  N-(β-hydroxy-isobutyl)-dodeca-2,4,8,10-tetraenamide 在 palladium on activated charcoal 、 溶剂黄146 作用下， 生成 N-(β-hydroxy-isobutyl)-lauramide
  参考文献：
  名称：

  Asano; Aihara, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1949, vol. 69, p. 80

  摘要：

  DOI：

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。
• 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.
• Aihara, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1951, vol. 71, p. 1112,1115
  作者：Aihara

  DOI：——

  日期：——
• 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