3,7-dimethylocta-2,6-dienyl 3,4,5-trihydroxybenzoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,7-dimethylocta-2,6-dienyl 3,4,5-trihydroxybenzoate
• 英文别名: geranyl gallate；[(2E)-3,7-dimethylocta-2,6-dienyl] 3,4,5-trihydroxybenzoate
• 化学式: C₁₇H₂₂O₅
• 分子量: 306.359
• InChiKey: MSJJHLNDRMIKET-KPKJPENVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  香叶醇 、 没食子酸 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以57%的产率得到3,7-dimethylocta-2,6-dienyl 3,4,5-trihydroxybenzoate
  参考文献：
  名称：

  抗真菌剂的分子设计。

  摘要：

  在设计啤酒酵母抗真菌剂的合理方法中，合成了一系列烷基没食子酸酯（3,4,5-三羟基苯甲酸酯）并进行了分析。没食子酸壬酯（1）最有效，最小杀真菌剂浓度（MFC）为12.5 microg / mL（42 microM），其次为没食子酸辛酯（2），MFC为25 microg / mL（89 microM）。这些MFC受pH值的影响很小。时间杀灭曲线研究表明，没食子酸壬酯在任何生长阶段均表现出对啤酒酵母的杀真菌活性。没食子酸壬酯的抗真菌活性主要是由于其充当非离子表面活性剂（表面活性剂）的能力。烷基的长度不是主要的贡献因素，但是在很大程度上引起活性方面起作用。就没食子酸烷基酯而言，

  DOI：

  10.1021/jf020088v

文献信息

• Inhibition of vertebrate squalene epoxidase by isoprenyl gallates and phenylalkyl gallates
  作者：Ikuro Abe、Yasuhiko Kashiwagi、Hiroshi Noguchi

  DOI：10.1016/s0960-894x(00)00526-6

  日期：2000.11

  'substrate-like' isoprenoid or phenylalkyl side chains were newly synthesized and tested for the enzyme inhibition activities toward recombinant rat squalene epoxidase. Isoprenyl gallates (4-6) showed good inhibition (IC50 = 1.5 5.1 microM), as potent as previously reported substrate analogues, while phenylalkyl gallates (7-10) were moderate inhibitors of the enzyme (IC50 = 12-61 microM).

  新合成了具有“底物状”类异戊二烯或苯烷基侧链的Galloy酯，并测试了其对重组大鼠角鲨烯环氧酶的酶抑制活性。异戊烯酸没食子酸酯（4-6）显示出良好的抑制作用（IC50 = 1.5 5.1 microM），与以前报道的底物类似物一样有效，而没食子酸苯烷基酯（7-10）则是该酶的中度抑制剂（IC50 = 12-61 microM）。
• Antifungal activity of octyl gallate: structural criteria and mode of action
  作者：Isao Kubo、Ping Xiao、Ken'ichi Fujita

  DOI：10.1016/s0960-894x(00)00656-9

  日期：2001.2

  Octyl gallate (3,4,5-trihydroxybenzoate) was found to possess antifungal activity against Saccharomyces cerevisiae and Zygosaccharomyces bailii, in addition to its potent antioxidant activity. Catechol moiety is essential to elicit this activity. The primary fungicidal activity of octyl gallate comes from its ability to act as a nonionic surface-active agent (surfactant). The length of the alkyl chain is not a major contributor but plays an important role in eliciting the activity. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Anti-<i>Salmonella</i> Activity of Alkyl Gallates
  作者：Isao Kubo、Ken-ichi Fujita、Ken-ichi Nihei

  DOI：10.1021/jf020467o

  日期：2002.11.1

  A series of alkyl gallates (3,4,5-trihydroxybenzoates) was synthesized and tested for their antibacterial activity against Salmonella choleraesuis. Nonyl (C-9) and octyl (C-8) gallates were noted to be the most effective against this food-borne bacterium, each with a minimum bactericidal concentration (MBC) of 12.5 mug/mL, followed by decyl (C-10) gallate, with a MBC of 25 mug/mL. Dodecyl (C-12) gallate exhibited activity against S. choleraesuis, with a MBC of 50 mug/mL. Propyl (C-3) gallate showed no activity against S. choleraesuis up to 3200 mug/mL. The length of the alkyl group is not a major contributor but plays a role in eliciting the activity to a large extent. The same series of alkyl gallates, regardless of alkyl chain length, all showed nearly the same potent scavenging activity on the 1,1-diphenyl-2-picrylhydrazyl radical, indicating that the length of the alkyl group is not associated with the activity.
• [EN] LIPID-BASED GYNAECOLOGIC SUPPOSITORY<br/>[FR] SUPPOSITOIRE GYNÉCOLOGIQUE À BASE DE LIPIDES
  申请人：GHISALBERTI CARLO

  公开号：WO2008090440A1

  公开（公告）日：2008-07-31

  [EN] Vaginal suppository essentially formed by C 10-C12 lipids, namely medium chain fatty acid (MCFA) and monoglycerides thereof, with melting point from 32° to 36°C, optionally comprising additional ingredients to enhance the overall biocidal effect.
  [FR] La présente invention concerne un suppositoire vaginal essentiellement formé de lipides en C₁₀-C₁₂, à savoir un acide gras à chaîne moyenne (Medium Chain Fatty Acid : MCFA) et des monoglycérides de celui-ci, dont le point de fusion est compris entre 32 et 36 °C, comprenant facultativement des ingrédients supplémentaires destinés à améliorer l'effet biocide global.