tetradecyl protocatechuate

• 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: tetradecyl protocatechuate
• 英文别名: Tetradecyl 3,4-dihydroxybenzoate
• 化学式: C₂₁H₃₄O₄
• 分子量: 350.499
• InChiKey: JIQWKYMKDDDXGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  25
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  原儿茶酸 、 十四醇 在 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 48.0h， 生成 tetradecyl protocatechuate
  参考文献：
  名称：

  抑制HIV-1蛋白酶二聚的烷基羟基苯甲酸衍生物。

  摘要：

  没食子酸及其衍生物作为抗癌剂，抗微生物剂和抗病毒剂的治疗潜力是众所周知的。我们已经研究了天然没食子酸和新合成的没食子酸烷基酯以及相关的原儿茶酸烷基酯抑制HIV-1蛋白酶的机制，以比较芳香环取代对抑制的影响。我们使用Zhang-Poorman的动力学分析和荧光探针结合来证明几种没食子酸和蛋白儿茶酸烷基酯通过阻止这种专性同二聚天冬氨酸蛋白酶的二聚作用而不是靶向活性位点来抑制HIV-1蛋白酶。没食子酸酯中的三羟基取代的苯甲酸部分比原儿茶酸酯中的二取代的苯甲酸部分更有利。在这两个系列中，抑制的类型 其机理和抑制效率极大地取决于烷基链的长度：对长度小于8个碳原子的烷基链没有抑制作用。分子动力学模拟证实了动力学数据，并提出没食子酸酯插在两个N和C单体末端之间。他们完成了β-折叠并破坏了二聚酶。最好的没食子酸酯（14个碳原子，K（id）为320 nM）也抑制了多突变蛋白酶MDR-HM。这些结果将有助于合

  DOI：

  10.2174/092986712803251557

文献信息

• Molecular Design of Multifunctional Food Additives:  Antioxidative Antifungal Agents
  作者：Ken-ichi Nihei、Atsuko Nihei、Isao Kubo

  DOI：10.1021/jf049687n

  日期：2004.8.1

  by pH values. The fungicidal activity of alkyl 3,4-dihydroxybenzoates was noted in combination with their ability to disrupt the native membrane-associated function nonspecifically as surface-active agents (surfactants) and to inhibit the respiratory electron transport. However, the primary fungicidal activity of nonyl 3,4-dihydroxybenzoate likely comes from its ability to act as a surfactant.

  合成了一系列的3,4-二羟基苯甲酸烷基酯（原儿茶酸酯），并使用2-倍连续肉汤稀释法测定了它们对酿酒酵母的杀真菌活性。3,4-二羟基苯甲酸壬基酯和辛基酯被认为对这种酵母最有效，其杀真菌剂的最低浓度分别为12.5微克/毫升。发现该活性与疏水性烷基链长相关。时间杀灭曲线研究表明，3,4-二羟基苯甲酸壬酯在任何生长阶段均对啤酒酵母有杀真菌作用，且该活性不受pH值的影响。烷基3的杀菌活性 注意到4-二羟基苯甲酸酯具有非特异性破坏天然膜相关功能作为表面活性剂（表面活性剂）并抑制呼吸电子转运的能力。但是，3,4-二羟基苯甲酸壬酯的主要杀真菌活性可能来自其作为表面活性剂的能力。
• Structure-Activity Relationships of Neuritogenic Gentiside Derivatives
  作者：Yan Luo、Kaiyue Sun、Lin Li、Lijuan Gao、Guangfa Wang、Yuan Qu、Lan Xiang、Ling Chen、Yongzhou Hu、Jianhua Qi

  DOI：10.1002/cmdc.201100348

  日期：2011.11.4

  Relationship advice: Studying the structure–activity relationships of gentisides revealed that the length of the alkyl chain, number and position of hydroxy groups on the benzene ring, and the type of linker between the benzene ring and alkyl chain have significant effects on their neuritogenic activities. Tetradecyl 2,3‐dihydroxybenzoate (ABG‐001) was the most promising lead compound, inducing significant

  关系建议：研究龙胆苷的结构-活性关系发现，烷基链的长度，苯环上羟基的数量和位置以及苯环和烷基链之间的连接基类型对它们的神经生成活性有重要影响。2,3-二羟基苯甲酸十四烷基酯（ABG-001）是最有前途的先导化合物，可通过激活ERK信号传导途径诱导明显的神经突长出。
• Thermochromic solid having reversibly invisible/visible construction enclosed therein
  申请人：THE PILOT INK CO., LTD.

  公开号：EP1095996A1

  公开（公告）日：2001-05-02

  A solid has a reversibly invisible/visible thermochromic internal construction enclosed therein which is composed of a solid made of a transparent resin and a fluorescent internal construction showing the internal structure of the solid enclosed therein, wherein a reversible thermochromic layer containing a reversible thermochromic composition is formed on the surface of the solid, or the transparent resin contains a reversible thermochromic composition.

  一种固体具有可逆的不可见/可见热致变色内部结构，它由透明树脂制成的固体和显示内部结构的荧光内部结构组成，其中固体表面形成含有可逆热致变色成分的可逆热致变色层，或透明树脂含有可逆热致变色成分。
• Antioxidant activity of protocatechuates evaluated by DPPH, ORAC, and CAT methods
  作者：Claudia Grajeda-Iglesias、Erika Salas、Nathalie Barouh、Bruno Baréa、Atikorn Panya、Maria Cruz Figueroa-Espinoza

  DOI：10.1016/j.foodchem.2015.07.119

  日期：2016.3

  Hibiscus sabdariffa L. is a worldwide consumed plant, principally after infusion of its dried sepals and calyces, which are usually discarded. Nevertheless, they represent a potential source of natural bioactive compounds, e.g. polyphenols, which could add value to this under-exploited plant. Protocatechuic acid (PA) was chosen as a model of the phenolic acids that can be extracted from H. sabdariffa. In order to modify PA hydrophilic character, which limits its use in lipid-rich food products, PA was esterified to C-1-C-18 alcohols, and the impact of lipophilization on its antioxidant activity was evaluated in both, an homogeneous (DPPH and ORAC methods) and an heterogeneous (CAT method) system. Results herein obtained showed that, depending on the grafted alkyl chain length, lipophilization could positively affect the antioxidant activity of PA in heterogeneous media; therefore, support its use as an innovative way to synthesize molecules with an improved antioxidant capacity and potential to be used as multifunctional preservatives in food. (C) 2015 Elsevier Ltd. All rights reserved.
• US6468088B1
  申请人：——

  公开号：US6468088B1

  公开（公告）日：2002-10-22