香兰素胺硬脂酸盐 | 58493-50-8

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 香兰素胺硬脂酸盐
• 英文名称: N-Vanillyloctadecanamide
• 英文别名: N-(4-hydroxy-3-methoxybenzyl)octadecanamide；N-vanillyl-octadecanamide；stevanil；N-vanillyl-stearamide；N-Vanillyl-stearinamid；N-Vanillyl-stearamid；Octadecanamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-；N-[(4-hydroxy-3-methoxyphenyl)methyl]octadecanamide
• CAS: 58493-50-8
• 化学式: C₂₆H₄₅NO₃
• 分子量: 419.648
• InChiKey: SBFFPOWNFONUBK-UHFFFAOYSA-N

物化性质

• 熔点：
  94.5-95 °C
• 沸点：
  586.1±40.0 °C(Predicted)
• 密度：
  0.973±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  30
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090
• 储存条件：
  2-8℃，存放在密闭和干燥的环境中。

反应信息

• 作为产物：
  描述：

  硬脂酸 在 草酰氯 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 香兰素胺硬脂酸盐
  参考文献：
  名称：

  香草。1.具有抗伤害感受和抗炎活性的辣椒素类似物。

  摘要：

  作为建立香草醛的结构活性关系的程序的一部分，辛辣成分辣椒素的类似物，母体结构的烷基链部分（以及衍生自高香草酸的相关化合物）发生了变化。在抗伤害感受和抗炎试验（大鼠和小鼠热板以及巴豆油刺激的小鼠耳朵）中，具有广泛变化的烷基链结构的化合物具有活性。短链化合物在上述测定中通过全身给药具有活性，但它们保留了辣椒素的高刺激性和急性毒性特征。相比之下，长链顺式不饱和物NE-19550（香草基油酰胺）和NE-28345（油基单香草酰胺）具有口服活性，刺激性较低，并且比辣椒素的急性毒性小。

  DOI：

  10.1021/jm00070a002

文献信息

• Salt taste modification
  申请人：DeSimone A. John

  公开号：US20050031717A1

  公开（公告）日：2005-02-10

  The pharmacology of the capsaicin receptor has been discovered to be predictive of the enhancement of the non-specific salt taste channel. Salt taste in a mammal may be modified by introducing to a mammalian taste receptor cell, a non-salty ligand which is a taste modulator. Examples of the ligand include capsaicin; resiniferatoxin (RTX); piperine; 2-(3,4-dimethylbenzyl)-3-[(4-hydroxy-3-methoxybenzyl)amino]carbothioyl}propyl pivalate (agonist 23); olvanil, capsiate; evodiamine; ethanol; cetylpyridinium chloride; dodecylpyridinium bromide; capsazepin; SB366791, etc. Salt taste thus may be modified by a non-salty ligand. By introducing certain non-salty ligands into the salt transduction process, the cation non-specific salt taste transduction process may be modified.

  人们发现，辣椒素受体的药理学可以预测非特异性盐味通道的增强。哺乳动物的盐味可以通过向哺乳动物味觉受体细胞引入一种非咸味配体来改变，这种配体是一种味觉调节剂。配体的例子包括辣椒素、树脂松香霉素（RTX）、胡椒碱、2-(3,4-二甲基苄基)-3-[(4-羟基-3-甲氧基苄基)氨基]碳硫酰基}丙基特戊酸酯（激动剂 23）、奥尔万尼尔、辣椒碱、依伏二胺、乙醇、十六烷基氯化吡啶、十二烷基溴化吡啶、辣椒平、SB366791 等。因此，盐味可以通过非咸味配体来改变。通过在盐味转导过程中引入某些非咸味配体，可以改变阳离子非特异性盐味转导过程。
• Ford-Moore; Phillips, Recueil des Travaux Chimiques des Pays-Bas, 1934, vol. 53, p. 855
  作者：Ford-Moore、Phillips

  DOI：——

  日期：——
• <i>N</i>-Acylvanillamides:  Development of an Expeditious Synthesis and Discovery of New Acyl Templates for Powerful Activation of the Vanilloid Receptor
  作者：Giovanni Appendino、Alberto Minassi、Aniello Schiano Morello、Luciano De Petrocellis、Vincenzo Di Marzo

  DOI：10.1021/jm020844o

  日期：2002.8.1

  A simple and general synthesis of vanillamides was developed and employed to screen acids from the fatty and isoprenoid pools for new acyl templates of biological relevance as capsaicin analogues. Potent activation of the human vanilloid receptor 1 (VR1) was observed for the vanillamides of certain polyfunctional acids from both pools, showing that the vanilloid activity of capsaicinoids can be. substantially improved by introducing polar groups and/or unsaturations on the acyl moiety. The activity of the unsaturated analogues was maintained or even increased by cyclopropAnation, while omega dimerization led to a substantial increase of activity. Because of the Wide structural diversity of the library of compounds screened, these observations could not be translated into a single framework of structure-activity relationships. Nevertheless, a series of new highly active leads was identified, validating the pharmacological potential of the unnatural combination of natural building blocks to provide new bioactive compounds.
• Highly efficient synthesis of capsaicin analogues by condensation of vanillylamine and acyl chlorides in a biphase H2O/CHCl3 system
  作者：Bo Wang、Fan Yang、Yi-Fan Shan、Wen-Wei Qiu、Jie Tang

  DOI：10.1016/j.tet.2009.04.046

  日期：2009.7

  Highly efficient synthesis of capsaicin analogues was developed using condensation of vanillylamine with acyl chlorides in a biphase H2O/CHCl3 System under mild conditions. For C-4-C-18 aliphatic or aromatic acyl chlorides, the yields were up to 93-96% with high purity after a simple work-up procedure, and only 1-1.16 equiv of acyl chloride was needed in the reaction. (C) 2009 Elsevier Ltd. All rights reserved.
• Lipophilicity of capsaicinoids and capsinoids influences the multiple activation process of rat TRPV1
  作者：Akihito Morita、Yusaku Iwasaki、Kenji Kobata、Tohko Iida、Tomohiro Higashi、Kyoko Oda、Asami Suzuki、Masataka Narukawa、Shiho Sasakuma、Hidehiko Yokogoshi、Susumu Yazawa、Makoto Tominaga、Tatsuo Watanabe

  DOI：10.1016/j.lfs.2006.07.024

  日期：2006.11

  Analogs of capsaicin, such as capsaicinoids and capsinoids, activate a cation channel, transient receptor potential cation channel vanilloid subfamily 1 (TRPV1), and then increase the intracellular calcium concentration ([Ca2+](i)). These compounds would be expected to activate TRPV1 via different mechanism(s), depending on their properties. We synthesized several capsaicinoids and capsinoids that have variable lengths of acyl moiety. The activities of these compounds towards TRPV1 heterologously expressed in HEK293 cells were determined by measuring [Ca2+](i). When an extracellular or intracellular Ca2+ source was removed, some agonists such as capsaicin could increase [Ca2+](i). However, a highly lipophilic capsaicinoid containing C18:0 and capsinoids containing C14:0, C18:0, or C18:1 (the latter was named olvanilate) could not elicit a large increase in [Ca2+](i) in the absence of an extracellular or intracellular Ca2+ source. These results suggest that highly lipophilic compounds cause only a slight Ca2+ influx, via TRPV1 in the plasma membrane, and are not able to activate TRPV1 in the endoplasmic reticulum. (c) 2006 Elsevier Inc. All rights reserved.