(9Z,12Z,15Z)-N-苄基-9,12,15-十八碳三烯酰胺 | 883715-18-2

• 物质功能分类: 天然产物 - 生物碱
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (9Z,12Z,15Z)-N-苄基-9,12,15-十八碳三烯酰胺
• 中文别名: N-苄基-(9Z,12Z,15Z)-十八碳三烯酰胺
• 英文名称: (9Z,12Z,15Z)-N-benzyloctadeca-9,12,15-trienamide
• 英文别名: N-benzyl-9Z, 12Ζ, 15Z-octadecatrienamide；N-benzyl-(9Z,12Z,15Z)-octadecatrienamide；N-benzyloctadec-9Z,12Z,15Z-trienamide；N-benzyllinolenamide；α-linolenic acid N-benzylamide；N-benzyl-9Z,12Z,15Z-octadecatrienamide
• CAS: 883715-18-2
• 化学式: C₂₅H₃₇NO
• 分子量: 367.575
• InChiKey: VCMMYRWIEZCYDK-PDBXOOCHSA-N

物化性质

• 沸点：
  534.2±39.0 °C(Predicted)
• 密度：
  0.943±0.06 g/cm3(Predicted)
• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  27
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 储存条件：
  室温

制备方法与用途

概述

N-苄基-(9Z,12Z,15Z)-十八碳三烯酰胺是一种玛咖酰胺类化合物。这类化合物属于含氮生物碱，具有较低的碱性特征，在玛咖中由苄胺和脂肪酸分子经过生物转化生成，具有较长的碳链和多元不饱和度。在玛咖干根中的含量约为0.06%至0.52%，非常低，因此提出了大量合成的需求。

用途

N-苄基-(9Z,12Z,15Z)-十八碳三烯酰胺主要用于含量测定、鉴定和药理实验等。

生物活性

N-Benzyllinolenamide 是从玛卡中提取的玛卡酰胺，是一种脂肪酰胺水解酶 (FAAH) 抑制剂，其 IC50 值为 41.8 μM。

靶点

IC50: 41.8 μM (FAAH)

反应信息

• 作为产物：
  描述：

  Γ-十八碳三烯酸 、 苄胺 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以37.27 %的产率得到(9Z,12Z,15Z)-N-苄基-9,12,15-十八碳三烯酰胺
  参考文献：
  名称：

  The Efficient Synthesis and Anti-Fatigue Activity Evaluation of Macamides: The Unique Bioactive Compounds in Maca

  摘要：

  玛卡酰胺是一类酰胺生物碱，只存在于玛卡中，被广泛认为是玛卡的生物活性标志化合物。近年来已发现三十多种玛卡酰胺单体，但由于其结构和特性相似，很难从玛卡植物中获得单一的玛卡酰胺单体。我们采用碳二亚胺缩合法（CCM）高效合成了五种典型的马卡酰胺，包括 N-苄基十六酰胺（NBH）、N-苄基-9Z,12Z,15Z-辛酰胺（NBH）、N-苄基-9Z,12Z,15Z-辛酰胺（NBH）、N-苄基-9Z,12Z,15Z-辛酰胺（NBH12Z,15Z-十八烯酰胺、N-(3-甲氧基苄基)-9Z,12Z-十八烯酰胺、N-苄基-9Z,12Z-十八烯酰胺和 N-(3-甲氧基苄基)-9Z,12Z,15Z-十八烯酰胺。所有合成的大酰胺均通过一步高效液相色谱法纯化，纯度超过 95%。NBH是天然玛咖中含量最高的玛酰胺单体，因此被选来评估玛酰胺的抗疲劳作用。结果表明，NBH能提高肝糖原水平，降低血尿素氮、乳酸脱氢酶、血氨和血乳酸水平，从而增强小鼠的耐力。玛卡酰胺可能是赋予玛卡抗疲劳活性功能的活性物质。

  DOI：

  10.3390/molecules28093943

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。
• 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.
• <i>N</i>-Benzyl-linoleamide, a Constituent of <i>Lepidium meyenii</i> (Maca), Is an Orally Bioavailable Soluble Epoxide Hydrolase Inhibitor That Alleviates Inflammatory Pain
  作者：Nalin Singh、Bogdan Barnych、Christophe Morisseau、Karen M. Wagner、Debin Wan、Ashley Takeshita、Hoang Pham、Ting Xu、Abhaya Dandekar、Jun-Yan Liu、Bruce D. Hammock

  DOI：10.1021/acs.jnatprod.0c00938

  日期：2020.12.24

  Lepidium meyenii (maca), a plant indigenous to the Peruvian Andes, recently has been utilized globally for claimed health or recreational benefits. The search for natural products that inhibit soluble epoxide hydrolase (sEH), with therapeutically relevant potencies and concentrations, led to the present study on bioactive amide secondary metabolites found in L. meyenii, the macamides. Based on known and suspected macamides, 19 possible macamides were synthesized and characterized. The majority of these amides displayed excellent inhibitory potency (IC₅₀ ≈ 20-300 nM) toward the recombinant mouse, rat, and human sEH. Quantitative analysis of commercial maca products revealed that certain products contain known macamides (1-5, 8-12) at therapeutically relevant total concentrations (≥3.29 mg/g of root), while the inhibitory potency of L. meyenii extracts directly correlates with the sum of concentration/IC₅₀ ratios of macamides present. Considering both its in vitro efficacy and high abundance in commercial products, N-benzyl-linoleamide (4) was identified as a particularly relevant macamide that can be utilized for in vivo studies. Following oral administration in the rat, compound 4 not only displayed acceptable pharmacokinetic characteristics but effectively reduced lipopolysaccharide-induced inflammatory pain. Inhibition of sEH by macamides provides a plausible biological mechanism of action to account for several beneficial effects previously observed with L. meyenii treatments.
• A METHOD FOR TREATING PERIPHERAL INFLAMMATORY DISEASE
  申请人：Dublin City University

  公开号：EP3297621A1

  公开（公告）日：2018-03-28
• 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