N-(4-hydroxy-3-methoxybenzyl)tetradecanamide | 69693-12-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-(4-hydroxy-3-methoxybenzyl)tetradecanamide
• 英文别名: N-myristoylvanillylamine；N-vanillyl-tetradecanamide；N-Vanillyl-tetradecanamid；N-Vanillyl-myristinamid；N-vanillylmyristamide；N-[(4-hydroxy-3-methoxyphenyl)methyl]tetradecanamide
• CAS: 69693-12-5
• 化学式: C₂₂H₃₇NO₃
• 分子量: 363.541
• InChiKey: CDJVNVARFLTQIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  26
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  棕榈酸甲酯 、 N-(4-hydroxy-3-methoxybenzyl)tetradecanamide 在 borate buffer 、 N,N-二异丙基乙胺 作用下， 以 水 为溶剂， 反应 48.0h， 以12.9%的产率得到N-[(4-羟基-3-甲氧基苯基)甲基]十六烷酰胺
  参考文献：
  名称：

  肝丙酮粉酶促合成辣椒素类似物

  摘要：

  通过使用肝丙酮粉末作为催化剂已经实现了具有饱和或不饱和酰基部分的辣椒素类似物的酶促合成。

  DOI：

  10.1016/0040-4039(96)00429-7
• 作为产物：
  描述：

  五甲基呋喃溴酸酯 、 香兰素胺盐酸盐 在 borate buffer 、 N,N-二异丙基乙胺 作用下， 以 水 为溶剂， 反应 48.0h， 以17.2%的产率得到N-(4-hydroxy-3-methoxybenzyl)tetradecanamide
  参考文献：
  名称：

  肝丙酮粉酶促合成辣椒素类似物

  摘要：

  通过使用肝丙酮粉末作为催化剂已经实现了具有饱和或不饱和酰基部分的辣椒素类似物的酶促合成。

  DOI：

  10.1016/0040-4039(96)00429-7

文献信息

• Application of Hansch’s Model to Capsaicinoids and Capsinoids: A Study Using the Quantitative Structure−Activity Relationship. A Novel Method for the Synthesis of Capsinoids
  作者：Gerardo F. Barbero、José M. G. Molinillo、Rosa M. Varela、Miguel Palma、Francisco A. Macías、Carmelo G. Barroso

  DOI：10.1021/jf9035029

  日期：2010.3.24

  been synthesized, and a new method for the synthesis of these compounds has been developed. The yields range from 48.35 to 98.98%. It has been found that the synthetic capsaicinoids and capsinoids present a lipophilia similar to those of the natural compounds and present similar biological activity. The bioactivity of the synthetic capsaicinoids and capsinoids decreases proportionally to the degree of

  作为结构和活性之间定量关系研究的一部分，我们描述了两种类化合物的合成方法：辣椒素和辣椒素。总共合成了14个增加的侧链长度（从2到16个碳原子）的辣椒素。另外，已经合成了14个具有相同侧链的辣椒素以及衣壳和二氢衣壳，并且已经开发了用于合成这些化合物的新方法。产率为48.35至98.98％。已经发现，合成的辣椒素类和辣椒素类具有与天然化合物相似的亲脂性，并具有相似的生物学活性。与天然化合物相比，合成辣椒素和辣椒素的生物活性与亲脂性差异程度（较高或较低）成比例地降低。使用黄化的小麦测定生物活性（小麦胚芽鞘生物测定法，并通过将合成结果与其对应的天然化合物呈现的结果进行比较。发现的生物活性与合成化合物的亲脂性直接相关。
• Anti-tumor pharmaceutical composition comprising N-vanillyl fatty acid amide
  申请人：KUREHA CHEMICAL INDUSTRY COMPANY, Limited

  公开号：US20040110844A1

  公开（公告）日：2004-06-10

  The present invention provides an anti-tumor pharmaceutical composition having a high anti-tumor effect with low side-effects. The anti-tumor pharmaceutical composition comprises a N-vanillyl fatty acid amide of formula (1): 1 wherein —CO—R group represents a saturated or unsaturated fatty acid residue containing from 14 to 32 carbon atoms. According to the invention, there was provided an anti-tumor pharmaceutical composition comprising a N-vanillyl fatty acid amide which relates to capsaicin wherein the composition has a low side-effect and a high anti-tumor effect, in particular an anti-melanoma effect and an anti-leukemia cell effect; and is very low pungent, stimulatory and preinflammatory effect.

  本发明提供了一种抗肿瘤药物组合物，具有高抗肿瘤效果和低副作用。该抗肿瘤药物组合物包括式（1）中的N-香草酰基脂肪酰胺：其中，—CO—R基团代表含有14至32个碳原子的饱和或不饱和脂肪酸残基。根据本发明，提供了一种抗肿瘤药物组合物，包括一种与辣椒素相关的N-香草酰基脂肪酰胺，该组合物具有低副作用和高抗肿瘤效果，特别是抗黑色素瘤效果和抗白血病细胞效果；且具有非常低的刺激性和预炎症效果。
• Method of producing capsaicin analogues
  申请人：Maruzen Pharmaceuticals Co., Ltd.

  公开号：US06022718A1

  公开（公告）日：2000-02-08

  A method of producing a capsaicin analogue, comprising reacting a fatty acid having 12 or more carbon atoms or an ester thereof (inclusive of fats and oils) with capsaicin in the presence of lipase to produce an N-vanillyl fatty acid amide having an acyl group containing 12 or more carbon atoms, and a method of producing fats and oils containing capsaicin analogues, comprising reacting edible fats and oils with capsaicin in the presence of lipase to produce N-vanillyl fatty acid amides from a portion of the edible fats and oils are provided. It is possible to produce non-pungent capsaicin analogues and other capsaicin analogues, which facilitates utilization of non-pungent capsaicin analogues in the food industry.

  一种制备辣椒素类似物的方法，包括在脂肪酶存在下，将含有12个或更多碳原子的脂肪酸或其酯（包括脂肪和油）与辣椒素反应，生成含有12个或更多碳原子的酰基的N-香草酰胺脂肪酸，并提供一种制备含有辣椒素类似物的脂肪和油的方法，包括在脂肪酶存在下，将可食用的脂肪和油与辣椒素反应，从部分可食用的脂肪和油中生成N-香草酰胺脂肪酸。可以生产非辣的辣椒素类似物和其他辣椒素类似物，从而促进非辣的辣椒素类似物在食品工业中的利用。
• Anti-tumour pharmaceutical composition comprising N-vanillyl fatty acid amide
  申请人：Kureha Chemical Industry Company, Limited

  公开号：EP1426047A1

  公开（公告）日：2004-06-09

  The present invention provides an anti-tumor pharmaceutical composition having a high anti-tumor effect with low side-effects. The anti-tumor pharmaceutical composition comprises a N-vanillyl fatty acid amide of formula (1):    wherein -CO-R group represents a saturated or unsaturated fatty acid residue containing from 14 to 32 carbon atoms. According to the invention, there is provided an anti-tumor pharmaceutical composition comprising a N-vanillyl fatty acid amide which is related to capsaicin wherein the composition has a low side-effect and a high anti-tumor effect, in particular an anti-melanoma effect and an anti-leukemia cell effect; and has a very low pungency, a stimulatory and a preinflammatory effect.

  本发明提供了一种抗肿瘤药物组合物，其抗肿瘤效果好，副作用小。 该抗肿瘤药物组合物包括式（1）的 N-香草醛脂肪酸酰胺： 其中 -CO-R 基团代表含有 14 至 32 个碳原子的饱和或不饱和脂肪酸残基。 根据本发明，提供了一种抗肿瘤药物组合物，其中包含一种与辣椒素有关的 N-香草醇脂肪酸酰胺，该组合物具有低副作用和高抗肿瘤效果，特别是抗黑色素瘤效果和抗白血病细胞效果；并且具有极低的辛辣味、刺激和预炎效果。
• A Novel Acylase from <i>Streptomyces mobaraensis</i> that Efficiently Catalyzes Hydrolysis/Synthesis of Capsaicins as Well as <i>N</i>-Acyl-<scp>l</scp>-amino Acids and <i>N</i>-Acyl-peptides
  作者：Mayuko Koreishi、Demin Zhang、Hiroyuki Imanaka、Koreyoshi Imamura、Shuji Adachi、Ryuichi Matsuno、Kazuhiro Nakanishi

  DOI：10.1021/jf052102k

  日期：2006.1.1

  A novel enzyme that catalyzes efficient hydrolysis of capsaicin (8-methyl-N-vanillyl-6-nonenamide) was isolated from the culture broth of Streptomyces mobaraensis. The enzyme consisted of two dissimilar subunits with molecular masses of 61 and 19 kDa. The enzyme was activated and stabilized in the presence of Co2+. It showed a pH optimum of about 8 and was stable at temperatures of up to 55 degrees C for 1 h at pH 7.8. The specific activity of the enzyme for the hydrolysis of capsaicin was 10(2)-10(4) times higher than those for the enzymes reported to date. In an aqueous/n-hexane biphasic system, capsaicin analogues such as octanoyl, decanoyl, and lauroyl vanillylamides were synthesized from the corresponding fatty acids and vanillylamine at yields of 50% or greater. In addition, the enzyme catalyzed the deacylation of N-lauroyl-L-amino acids and N-lauroyl-L-dipeptides and the efficient synthesis of N alpha-lauroyl-L-lysine, N epsilon-lauroyl-L-lysine, and various N-lauroyl-peptides in aqueous solution in both the absence and the presence of glycerol.