(Z)-N-benzyltetracos-15-enamide

• 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: (Z)-N-benzyltetracos-15-enamide
• 英文别名: N-benzyl-15Z-tetracosenamide
• 化学式: C₃₁H₅₃NO
• 分子量: 455.768
• InChiKey: LQJKLTWHJMDOQD-KTKRTIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.8
• 重原子数：
  33
• 可旋转键数：
  23
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  神经酸 、 苄胺 在 N,N'-羰基二咪唑 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以94%的产率得到(Z)-N-benzyltetracos-15-enamide
  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

• New Alkamides from Maca (<i>Lepidium meyenii</i>)
  作者：Jianping Zhao、Ilias Muhammad、D. Chuck Dunbar、Jamal Mustafa、Ikhlas A. Khan

  DOI：10.1021/jf048529t

  日期：2005.2.1

  Maca (Lepidium meyenii) has been used as a food in Peru for thousands of years. More recently a wide array of commercial maca products have gained popularity as dietary supplements, with claims of anabolic and aphrodisiac effects, although the biologically active principles are not fully known. In an earlier chemical investigation, two new alkamides and a novel fatty acid, as well as the N-hydroxypyridine derivative, macaridine, were isolated from L. meyenii. Further examination has led to the isolation of five additional new alkamides, namely, N-benzyl-9-oxo-12Z-octadecenamide (1), N-benzyl-9-oxo-12Z, 15Z-octadecadienamide (2), N-benzyl-13-oxo-9E,11E-octadecadienamide (3), N-benzyl-15Z-tetracosenamide (4), and N-(m-methoxybenzyl)hexadecanamide (5). Their structures were established by spectrometric and spectroscopic methods including ESI-HRMS, EI-MS, H-1, C-13, and 2D NMR, as well as H-1-N-15 2D HMBC experiments. In addition, the identity of N-benzyl-15Z-tetracosenamide (4) was confirmed by synthesis. These compounds have been found from only L. meyenii and could be used as markers for authentication and standardization.
• AROMATIC ALKAMIDES AND METHODS OF USE THEREOF IN TASTE MODULATION
  申请人：International Flavors & Fragrances Inc.

  公开号：EP3955752A1

  公开（公告）日：2022-02-23
• [EN] AROMATIC ALKAMIDES AND METHODS OF USE THEREOF IN TASTE MODULATION<br/>[FR] ALKAMIDES AROMATIQUES ET LEURS PROCÉDÉS D'UTILISATION DANS LA MODULATION DU GOÛT
  申请人：INT FLAVORS & FRAGRANCES INC

  公开号：WO2020214892A1

  公开（公告）日：2020-10-22

  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.