N-benzyl-5-oxo-6E,8E-octadecadienamide | 405906-95-8

• 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-benzyl-5-oxo-6E,8E-octadecadienamide
• 英文别名: Macamide 2；(6E,8E)-N-benzyl-5-oxooctadeca-6,8-dienamide
• CAS: 405906-95-8
• 化学式: C₂₅H₃₇NO₂
• 分子量: 383.574
• InChiKey: DKMGVACNAAKVRR-MRBSYODNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  28
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-十一炔 在 四(三苯基膦)钯 、 叔丁基锂 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 、 乙醚 、 正庚烷 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 49.17h， 生成 N-benzyl-5-oxo-6E,8E-octadecadienamide
  参考文献：
  名称：

  Macamides and their synthetic analogs: Evaluation of in vitro FAAH inhibition

  摘要：

  Maca (Lepidium meyenii), a traditional food crop of the Peruvian Andes is now widely touted as a dietary supplement. Among the various chemical constituents isolated from the plant are a unique series of non-polar, long-chain fatty acid N-benzylamides known as macamides. We have synthesized 11 of the 19 reported macamides and have tested each as potential inhibitors of the human enzyme, fatty acid amide hydrolase (FAAH). The five most potent macamides were FAAH inhibitors (IC50 = 10-17 mu M). These amides were derivatives of oleic, linoleic and linolenic acids and benzylamine or 3-methoxybenzylamine. Of the three compounds evaluated in a pre-incubation time study, two macamides were not irreversible inhibitors of FAAH. The third, a carbamate structurally related to macamides, was shown to be an irreversible inhibitor of FAAH (IC50 = 0.153 mu M). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.034

文献信息

• 一种玛咖酰胺的合成方法及其用途
  申请人：中国科学院过程工程研究所

  公开号：CN104513171B

  公开（公告）日：2017-09-01

  本发明涉及一种玛咖酰胺的合成方法，所述方法为：以脂肪酸，和苄胺或间甲氧基苄胺为反应原料，在已经溶解有HOAt、EDC·HCl及DIPEA的二氯甲烷溶液中混合，搅拌进行反应，然后将反应产物水洗，将水不溶物干燥即得玛咖酰胺。本发明所述合成玛咖酰胺的方法，步骤简单，原料易得，操作条件易控，产物无需纯化纯度即可达95%以上；为工业化合成玛咖酰胺提供了基础；另外，本发明合成的玛咖酰胺具有提高男性生育能力和治疗男性性功能障碍的作用，为玛咖酰胺的应用提供了市场前景。
• COMPOSITIONS OF ATOMIZED OR LYOPHILIZED MACA (Lepidium meyenii) EXTRACTS AND ATOMIZED OR LYOPHILIZED YACON (Smallanthus sanchifolius) EXTRACTS AS ADJUVANTS IN THE TREATMENT OF DIFFERENT CONDITIONS
  申请人：GONZALES RENGIFO Gustavo Francisco

  公开号：US20090280203A1

  公开（公告）日：2009-11-12

  The present invention refers to compositions of atomized or lyophilized extracts of selected maca hypocotyls of the red and black variety and atomized or lyophilized parts of the yacon plant selected from leaves and roots. The invention also refers to the methods to prepare such compositions using aqueous or hydroalcoholic extraction processes. Likewise, as novel element of the maca hypocotyls extraction process is the selection of the batches of maca hypocotyls having a pH of less than 5.5, which have better biological activity than those with a greater pH. The compositions of the invention are useful in the treatment of different conditions and diseases.
• AROMATIC ALKAMIDES AND METHODS OF USE THEREOF IN TASTE MODULATION
  申请人：INTERNATIONAL FLAVORS & FRAGRANCES INC.

  公开号：US20220202052A1

  公开（公告）日：2022-06-30

  A Lepidium meyenii extract, as well as aromatic alkamides thereof are described for use in compositions and methods for improving the taste of a consumable containing a component having an astringent, bitter or off-taste.
• Macamides and their synthetic analogs: Evaluation of in vitro FAAH inhibition
  作者：Hui Wu、Charles J. Kelley、Alejandro Pino-Figueroa、Huyen D. Vu、Timothy J. Maher

  DOI：10.1016/j.bmc.2013.06.034

  日期：2013.9

  Maca (Lepidium meyenii), a traditional food crop of the Peruvian Andes is now widely touted as a dietary supplement. Among the various chemical constituents isolated from the plant are a unique series of non-polar, long-chain fatty acid N-benzylamides known as macamides. We have synthesized 11 of the 19 reported macamides and have tested each as potential inhibitors of the human enzyme, fatty acid amide hydrolase (FAAH). The five most potent macamides were FAAH inhibitors (IC50 = 10-17 mu M). These amides were derivatives of oleic, linoleic and linolenic acids and benzylamine or 3-methoxybenzylamine. Of the three compounds evaluated in a pre-incubation time study, two macamides were not irreversible inhibitors of FAAH. The third, a carbamate structurally related to macamides, was shown to be an irreversible inhibitor of FAAH (IC50 = 0.153 mu M). (C) 2013 Elsevier Ltd. All rights reserved.