壬酸香草酯 | 131119-10-3

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 壬酸香草酯
• 中文别名: 合成辣椒素酯
• 英文名称: Vanillyl nonanoate
• 英文别名: (4-hydroxy-3-methoxyphenyl)methyl nonanoate
• CAS: 131119-10-3
• 化学式: C₁₇H₂₆O₄
• 分子量: 294.391
• InChiKey: VSINWHDOHWBJCS-UHFFFAOYSA-N

物化性质

• 密度：
  1.050

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  壬酸香草酯 以 乙醇 为溶剂， 反应 4.0h， 生成 4-羟基-3-甲氧基苄醇
  参考文献：
  名称：

  Protective Effect of Vanilloids against tert-Butyl Hydroperoxide-Induced Oxidative Stress in Vero Cells Culture

  摘要：

  This study investigated the effect of synthetic capsiate, a simplified analogue of capsiate, and vanillyl alcohol on the oxidative stress induced by tert-butyl hydroperoxide (TBH) in a line of fibroblasts derived from monkey kidney (Vero cells). In response to the TBH-mediated oxidative stress, a reduction of the levels of total unsaturated fatty acids and cholesterol was observed, and a rise in the concentrations of conjugated dienes fatty acids hydroperoxides and 7-ketocholesterol. Pretreatment with both synthetic capsiate and vanillyl alcohol preserved Vero cells from oxidative damage and showed a remarkable protective effect on the reduction of the levels of total unsaturated fatty acids and cholesterol, inhibiting the increase of MIDA, conjugated dienes fatty acids hydroperoxides, and 7-ketocholesterol. Both compounds were effective against peroxidation of cell membrane lipids induced by TBH, with synthetic capsiate essentially acting as a pro-drug of vanillyl alcohol, its hydrophilic hydrolytic derivative.

  DOI：

  10.1021/jf073448t
• 作为产物：
  描述：

  4-羟基-3-甲氧基苄醇 在 四氢吡咯 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 14.0h， 生成 壬酸香草酯
  参考文献：
  名称：

  Analogs of capsaicin with agonist activity as novel analgesic agents; structure-activity studies. 3. The hydrophobic side-chain "C-region"

  摘要：

  Structural variants of the hydrophobic side chain (''C region'') of the capsaicin molecule have been incorporated into a series of vanillylamides and vanillylthioureas. These compounds have been tested in an in vitro assay for agonism (Ca-45(2+) influx into dorsal root ganglia neurones), previously shown to be predictive of analgesic activity. The results of this study have established the requirement for a hydrophobic substituent of limited size (molar refractivity, MR, <55) in order to obtain high potency. Combination of the information gained here about the ''C-region'' of the capsaicin molecule with the studies described in the preceding two papers provides a rational basis for the design of compounds of increased potency.

  DOI：

  10.1021/jm00068a016

文献信息

• 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。
• ESTER DERIVATIVE AND USE THEREOF
  申请人：AMINO Yusuke

  公开号：US20090170942A1

  公开（公告）日：2009-07-02

  A compound represented by the following formula (I′) wherein X 1 is a methylene group, an ethylene group, a trimethylene group or a vinylene group, X 2 is a divalent group represented by the following formula A or B, Y is an ethylene group or a vinylene group, m and n are each an integer of 0 to 7, which satisfy m+n=0 to 8, R1 and R2 are each independently a hydrogen atom, a methyl group or an ethyl group, provided that when X 1 is a methylene group, then X 2 is not a divalent group represented by the formula A, and when X 1 is a vinylene group, then X 2 is not a divalent group represented by the formula A. The compound is a stable capsinoid derivative, and is useful as an active ingredient of an external blood circulation enhancer or a cosmetic composition, a pharmaceutical composition, or a food composition.

  以下式(I')表示的化合物 其中X1是亚甲基基团，亚乙基基团，亚丙基基团或乙烯基基团，X2是由以下式A或B表示的二价基团， Y是亚乙基基团或乙烯基基团，m和n都是0到7的整数，满足m+n=0到8，R1和R2各自独立为氢原子，甲基基团或乙基基团，条件是当X1是亚甲基基团时，那么X2不是由式A表示的二价基团，并且当X1是乙烯基基团时，那么X2不是由式A表示的二价基团。该化合物是一种稳定的辣椒素衍生物，并且作为外周血液循环增强剂，化妆品组合物，药物组合物或食品组合物的有效成分是有用的。
• Chemoselective Esterification of Phenolic Acids and Alcohols
  作者：Giovanni Appendino、Alberto Minassi、Nives Daddario、Federica Bianchi、Gian Cesare Tron

  DOI：10.1021/ol0266471

  日期：2002.10.1

  [formula: see text] The Mitsunobu reaction can distinguish between alcohol and phenol hydroxyls in esterification reactions, providing an expeditious and broadly applicable entry into various phenolics and polyphenolics of biomedical and nutritional relevance.

  Mitsunobu反应可以区分酯化反应中的醇羟基和酚羟基，为生物医学和营养相关的各种酚类和多酚类化合物提供了快速而广泛适用的入口。
• 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。
• Cerium(III) chloride-promoted chemoselective esterification of phenolic alcohols
  作者：Elisabetta Torregiani、Gianfranco Seu、Alberto Minassi、Giovanni Appendino

  DOI：10.1016/j.tetlet.2005.02.042

  日期：2005.3

  method for the chemoselective esterification of phenolic alcohols is described. The reaction overcomes the tyranny of protection, and capitalizes on the activation of acyl halides with cerium(III) chloride to selectively esterify alcohol hydroxyls in the presence of phenolic ones. The generality of the reaction was demonstrated with a series of phenolic alcohols of dietary relevance (vanillol, hydroxytyrosol

  描述了一种温和且操作简单的酚醇化学选择性酯化方法。该反应克服了保护的专制，并利用了氯化铈（III）活化酰基卤来在酚类羟基的存在下选择性酯化醇羟基。一系列具有饮食相关性的酚醇（香草醛，羟基酪醇，表儿茶素）证明了该反应的普遍性，从而迅速进入了一系列与生物医学研究相关的化合物，其中一些以前只能通过酶促方法获得。