vanillyl octadecanoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: vanillyl octadecanoate
• 英文别名: vanillyl stearate；(4-Hydroxy-3-methoxyphenyl)methyl octadecanoate
• 化学式: C₂₆H₄₄O₄
• 分子量: 420.633
• InChiKey: WKVXKWKCYNFVFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  30
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  硬酯酸甲酯C18 、 4-羟基-3-甲氧基苄醇 在 Novozym 435 、 4 Angstroem MS 作用下， 以 1,4-二氧六环 为溶剂， 反应 20.0h， 以66%的产率得到vanillyl octadecanoate
  参考文献：
  名称：

  Enzymatic Synthesis of a Capsinoid by the Acylation of Vanillyl Alcohol with Fatty Acid Derivatives Catalyzed by Lipases

  摘要：

  辣椒素类化合物是一组由辣椒植物产生的新型化合物。我们通过脂肪酶催化的酯化反应，在有机溶剂中合成了辣椒素类化合物。其中，17种商业可得的脂肪酶中有7种，特别是Novozym 435，适用于合成辣椒素类化合物的模型化合物——香草基壬酸酯。在最佳条件下，即50 mM香草基酒精和50 mM甲基壬酸酯在500μl的二恶烷中，使用20 mg的Novozym 435和50 mg的4Å分子筛在25°C下，20小时内香草基壬酸酯的产率为86%。从相应的脂肪酸甲酯合成的具有各种酰链长度（C6-C18）的几个辣椒素类同系物，产率在64-86%之间。在最佳条件下进行400倍的反应规模，分别以60%和59%的产率得到了天然辣椒素类化合物——辣椒碱和二氢辣椒碱。

  DOI：

  10.1271/bbb.66.319

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。
• 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.
• US9399030B2
  申请人：——

  公开号：US9399030B2

  公开（公告）日：2016-07-26
• Enzymatic Synthesis of a Capsinoid by the Acylation of Vanillyl Alcohol with Fatty Acid Derivatives Catalyzed by Lipases
  作者：Kenji KOBATA、Manami KAWAGUCHI、Tatsuo WATANABE

  DOI：10.1271/bbb.66.319

  日期：2002.1

  Capsinoids are a novel group of compounds produced by the Capsicum plant. We synthesized a capsinoid by the lipase-catalyzed esterification of vanillyl alcohol with fatty acid derivatives in an organic solvent. The use of seven out of 17 commercially available lipases, especially Novozym 435, was applicable to the synthesis of vanillyl nonanoate, a model compound of capsinoids. The yield of vanillyl nonanoate under the optimum conditions of 50 mM vanillyl alcohol and 50 mM methyl nonanoate in 500 μl of dioxane, using 20 mg of Novozym 435 and 50 mg of 4 Å molecular sieves at 25°C, was 86% in 20 h. Several capsinoid homologues having various acyl chain lengths (C6–C18) were synthesized at 64–86% yields from the corresponding fatty acid methyl ester. The natural capsinoids, capsiate and dihydrocapsiate, were obtained by a 400-fold-scale reaction at these optimum conditions in 60% and 59% isolated yields, respectively.

  辣椒素类化合物是一组由辣椒植物产生的新型化合物。我们通过脂肪酶催化的酯化反应，在有机溶剂中合成了辣椒素类化合物。其中，17种商业可得的脂肪酶中有7种，特别是Novozym 435，适用于合成辣椒素类化合物的模型化合物——香草基壬酸酯。在最佳条件下，即50 mM香草基酒精和50 mM甲基壬酸酯在500μl的二恶烷中，使用20 mg的Novozym 435和50 mg的4Å分子筛在25°C下，20小时内香草基壬酸酯的产率为86%。从相应的脂肪酸甲酯合成的具有各种酰链长度（C6-C18）的几个辣椒素类同系物，产率在64-86%之间。在最佳条件下进行400倍的反应规模，分别以60%和59%的产率得到了天然辣椒素类化合物——辣椒碱和二氢辣椒碱。