4-hydroxy-3-methoxybenzyl undecanoate | 906465-18-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-hydroxy-3-methoxybenzyl undecanoate
• 英文别名: vanillyl undecanoate；(4-Hydroxy-3-methoxyphenyl)methyl undecanoate
• CAS: 906465-18-7
• 化学式: C₁₉H₃₀O₄
• 分子量: 322.445
• InChiKey: CDKWGGBSPOSAKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  23
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  十一烷酸 在 吡啶 、 盐酸 、 氯化亚砜 、 水 作用下， 以 乙醇 为溶剂， 反应 37.0h， 生成 4-hydroxy-3-methoxybenzyl undecanoate
  参考文献：
  名称：

  Hansch模型在辣椒素和辣椒素中的应用：使用定量结构-活性关系的研究。辣椒素合成的新方法

  摘要：

  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。

  DOI：

  10.1021/jf9035029

文献信息

• Topically applied circulation enhancing agent and skin and hair cosmetic and bath agent containing the same
  申请人：Sagawa Koichiro

  公开号：US20060287390A1

  公开（公告）日：2006-12-21

  A topically applied circulation enhancing agent suited for application over the entire body which has good transdermal absorptivity and causes little irritation is provided. A topically applied circulation enhancing agent is provided which contains a fatty acid ester denoted by general formula (1):

  提供一种适用于全身涂抹的促进循环的药剂，具有良好的经皮吸收性且引起少量刺激。提供一种含有一种由通用公式(1)表示的脂肪酸酯的促进循环的局部应用药剂。
• METHOD FOR THE CHEMICAL SYNTHESIS OF CAPSINOIDS
  申请人：Universidad De Cádiz

  公开号：EP2149548A1

  公开（公告）日：2010-02-03

  Method for the chemical synthesis of capsinoids, natural compounds with proven biological activity, from vanillin, comprising the protection of the alcohol group thereof, reduction of the aldehyde to alcohol, esterification of same and deprotection of the first protected alcohol group. In this way, the desired compounds are generated with high purity and said compounds can be easily separated with no mixing owing to the competitive esterification on the aromatic ring.

  从香草醛合成辣椒素类化合物的化学合成方法，包括对其醇基的保护，将醛还原为醇，酯化反应，以及对第一个保护的醇基的去保护。通过这种方式，可以高纯度地生成所需的化合物，并且由于芳香环上的酯化竞争，这些化合物可以轻松分离而无需混合。
• Production method of capsinoid by dehydrating condensation, stabilizing method of capsinoid, and capsinoid composition
  申请人：Amino Yusuke

  公开号：US20070020738A1

  公开（公告）日：2007-01-25

  Capsinoids of formula (3) may be conveniently prepared in a high yield, in a short time, without using a dehydrating agent by esterification of a fatty acid of formula (1) with a hydroxymethylphenol of formula (2) using an enzyme without a solvent or in a low-polar solvent. Addition of a fatty acid represented by formula (4) is effective for stabilizing the ester compound of formula (3). wherein each symbol is as defined in the specification.

  公式（3）的辣椒素类化合物可以通过使用酶而不使用脱水剂，在无溶剂或低极性溶剂中，将公式（1）的脂肪酸与公式（2）的羟甲基酚酯化反应，高产率地、短时间内方便地制备。公式（4）表示的脂肪酸的加入对于稳定公式（3）的酯化合物是有效的。其中每个符号如规范中所定义。
• PRODUCTION METHOD OF CAPSINOID BY DEHYDRATING CONDENSATION, STABILIZING METHOD OF CAPSINOID, AND CAPSINOID COMPOSITION
  申请人：AMINO Yusuke

  公开号：US20100152291A1

  公开（公告）日：2010-06-17

  Capsinoids of formula (3) may be conveniently prepared in a high yield, in a short time, without using a dehydrating agent by esterification of a fatty acid of formula (1) with a hydroxymethylphenol of formula (2) using an enzyme without a solvent or in a low-polar solvent. Addition of a fatty acid represented by formula (4) is effective for stabilizing the ester compound of formula (3). wherein each symbol is as defined in the specification.

  公式（3）的辣椒素类物质可以通过使用酶而不使用脱水剂，在不使用溶剂或低极性溶剂的情况下，通过将公式（1）的脂肪酸与公式（2）的羟甲基酚酯化反应，高产率地、短时间内方便地制备。公式（4）代表的脂肪酸的添加对于稳定公式（3）的酯化物也是有效的。其中每个符号如规范中所定义。
• Evaluation of the Antioxidant Activity of Capsiate Analogues in Polar, Nonpolar, and Micellar Media
  作者：Kunduru K. Reddy、Thumu Ravinder、Rachapudi B. N. Prasad、Sanjit Kanjilal

  DOI：10.1021/jf104244m

  日期：2011.1.26

  Synthesis of 10 capsiate analogues was conducted by lipase-mediated (Novozyme 435) esterification of vanillyl alcohol with different fatty acids. The antioxidant activity of the synthesized capsiates was evaluated using three in vitro assays: DPPH radical scavenging assay (polar medium), Rancimat assay (nonpolar medium), and autoxidation of linoleic acid (micellar medium). The objective of this study is to find the influence of structural characteristics of the alkyl chain of capsiate analogues on their antioxidant activity. In these assays, BHT and alpha-tocopherol were used as reference compounds. Both DPPH and Rancimat assays did not show any specific trend of antioxidant activity with the increase in lipophilicity and also with the type of fatty acids grafted to the phenolic moiety. In the Tween 20 micellar system for the inhibition of autoxidation of linoleic acid, vanillyl ester attached to a C18 alkyl chain (vanillyl stearate, oleate and ricinoleate) exhibited maximum inhibition of autoxidation of linoleic acid.