n-decyl-3,4-dihydroxybenzoate | 105603-52-9

• 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: n-decyl-3,4-dihydroxybenzoate
• 英文别名: decyl 3,4-dihydroxybenzoate；decyl protocatechuate；Benzoic acid, 3,4-dihydroxy-, decyl ester
• CAS: 105603-52-9
• 化学式: C₁₇H₂₆O₄
• 分子量: 294.391
• InChiKey: IFNDOUMKRMLNES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 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：
  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 、 癸醇 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 以36%的产率得到n-decyl-3,4-dihydroxybenzoate
  参考文献：
  名称：

  多功能食品添加剂的分子设计：抗氧化抗真菌剂。

  摘要：

  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。

  DOI：

  10.1021/jf049687n

文献信息

• Alkyl Hydroxybenzoic Acid Derivatives that Inhibit HIV-1 Protease Dimerization
  作者：O. A. Flausino、L. Dufau、L. O. Regasini、M. S. Petronio、D. H.S. Silva、T. Rose、V. S. Bolzani、M. Reboud-Ravaux

  DOI：10.2174/092986712803251557

  日期：2012.9.1

  The therapeutic potential of gallic acid and its derivatives as anti-cancer, antimicrobial and antiviral agents is well known. We have examined the mechanism by which natural gallic acid and newly synthesized gallic acid alkyl esters and related protocatechuic acid alkyl esters inhibit HIV-1 protease to compare the influence of the aromatic ring substitutions on inhibition. We used Zhang-Poorman's

  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
• Design of Antibacterial Agents: Alkyl Dihydroxybenzoates against Xanthomonas citri subsp. citri
  作者：Ana Nazaré、Carlos Polaquini、Lúcia Cavalca、Daiane Anselmo、Marilia Saiki、Diego Monteiro、Aleksandra Zielinska、Paula Rahal、Eleni Gomes、Dirk-Jan Scheffers、Henrique Ferreira、Luis Regasini

  DOI：10.3390/ijms19103050

  日期：——

  Xanthomonas citri subsp. citri (Xcc) causes citrus canker, affecting sweet orange-producing areas around the world. The current chemical treatment available for this disease is based on cupric compounds. For this reason, the objective of this study was to design antibacterial agents. In order to do this, we analyzed the anti-Xcc activity of 36 alkyl dihydroxybenzoates and we found 14 active compounds. Among them, three esters with the lowest minimum inhibitory concentration values were selected; compounds 4 (52 μM), 16 (80 μM) and 28 (88 μM). Our study demonstrated that alkyl dihydroxybenzoates cause a delay in the exponential phase. The permeability capacity of alkyl dihydroxybenzoates in a quarter of MIC was compared to nisin (positive control). Compound 28 was the most effective (93.8), compared to compound 16 (41.3) and compound 4 (13.9) by percentage values. Finally, all three compounds showed inhibition of FtsZ GTPase activity, and promoted changes in protofilaments, leading to depolymerization, which prevents bacterial cell division. In conclusion, heptyl dihydroxybenzoates (compounds 4, 16 and 28) are promising anti-Xcc agents which may serve as an alternative for the control of citrus canker.

  柑橘溃疡病是由黄单胞菌亚种柑橘亚种（Xcc）引起的，影响全球甜橙产区。目前针对该疾病的化学治疗方法基于铜化合物。因此，本研究的目标是设计抗菌剂。为了实现这一目标，我们分析了36种烷基二羟基苯甲酸酯的抗Xcc活性，发现了14种活性化合物。其中，选择了三种具有最低最小抑制浓度值的酯类化合物；化合物4（52 μM）、16（80 μM）和28（88 μM）。我们的研究表明，烷基二羟基苯甲酸酯导致指数阶段的延迟。在四分之一MIC的渗透能力方面，烷基二羟基苯甲酸酯与尼星（阳性对照）进行了比较。化合物28的效果最好（93.8），相比化合物16（41.3）和化合物4（13.9）的百分比值。最后，所有三种化合物都显示了对FtsZ GTP酶活性的抑制，并促使原丝变化，导致解聚，从而阻止细菌细胞分裂。总之，庚基二羟基苯甲酸酯（化合物4、16和28）是有前途的抗Xcc剂，可能成为控制柑橘溃疡病的替代品。
• Improvement of Pro-Oxidant Capacity of Protocatechuic Acid by Esterification
  作者：Maria Luiza Zeraik、Maicon S. Petrônio、Dyovani Coelho、Luis Octavio Regasini、Dulce H. S. Silva、Luiz Marcos da Fonseca、Sergio A. S. Machado、Vanderlan S. Bolzani、Valdecir F. Ximenes

  DOI：10.1371/journal.pone.0110277

  日期：——

  account that hydroquinone and related moieties are frequently found in biomolecules and quinone-based chemotherapeutics, our demonstration that esters of protocatechuic acid are specific and potent co-catalysts in their oxidations may be very relevant as a pathway to exacerbate redox cycling reactions, which are usually involved in their biological and pharmacological mechanisms of action.

  酚类化合物的促氧化作用通常与苯氧基自由基的单电子氧化还原电位相关。在这里我们证明，除了它们的氧化性外，疏水性也是一个决定性因素。我们发现原儿茶酸 (P0) 的酯化对其促氧化能力产生了深远的影响。带有包含两个 (P2)、四个 (P4) 和七个 (P7) 碳的烷基链的酯，但没有酸前体 (P0)，能够加剧 trolox、α-生育酚和利福平的氧化。这种效果也取决于儿茶酚部分，因为没食子酸和没食子酸丁酯都没有表现出任何促氧化作用。还与夹竹桃素进行了比较，夹竹桃素在其促氧化特性方面具有很好的特征。在 trolox 的共氧化方面，P7 比夹竹桃素更有效。然而，P7 不能共同氧化谷胱甘肽和 NADH，它们是夹竹桃素自由基的目标。正如差分脉冲伏安法实验中峰值电流的强度所表明的那样，在促氧化能力和自由基的稳定性之间发现了相关性。总之，考虑到对苯二酚和相关部分经常存在于生物分子和基于醌的化学治疗剂中，我们证明原
• Protocatechuic Acid Alkyl Esters: Hydrophobicity As a Determinant Factor for Inhibition of NADPH Oxidase
  作者：C. M.Q.G. de Faria、A. C. Nazare、M. S. Petronio、L. C. Paracatu、M. L Zeraik、L. O. Regasini、D. H.S. Silva、L. M. da Fonseca、V. F. Ximenes

  DOI：10.2174/092986712803341557

  日期：2012.10.1

  This study presents the increased efficiency of NADPH oxidase inhibition produced by esterification of protocatechuic acid (P0). Alkyl esters bearing chain lengths of 4 (P4), 7 (P7) and 10 (P10) carbons were synthesized and their oxidation potential, hydrophobicity, antiradical activity, inhibition of superoxide anion (O2 °-), and the abilities to affect hypochlorous acid (HOCl) production by leukocytes and inhibit myeloperoxidase (MPO) chlorinating activity were studied. The increased hydrophobicity (logP, 0.81-4.82) of the esters was not correlated with a significant alteration in their oxidation potential (0.222-0.298 V). However, except for P10, the esters were ~ 2-fold more effective than the acid precursor for the scavenging of DPPH and peroxyl radicals. The esters were strong inhibitors of O2 °- released by activated neutrophils (PMNs) and peripheral blood mononuclear cells (PBMCs). A correlation was found between the carbon chain length and the relative inhibitory potency. P7, the most active ester, was ~ 10-fold more efficient as NADPH oxidase inhibitor than apocynin. The esters strongly inhibited the release of HOCl by PMNs, which was a consequence of the inhibition of NADPH oxidase activity in these cells. In conclusion, as effective inhibitors of NADPH oxidase, the esters of protocatechuic acid are promising drugs for treatment of chronic inflammatory diseases. Moreover, this is the first demonstration that, besides the redox active moiety, the hydrophobicity can also be a determinant factor for the design of NADPH oxidase inhibitors.

  本研究展示了通过对儿茶酸（P0）进行酯化所产生的NADPH氧化酶抑制效率的提高。合成了链长分别为4（P4）、7（P7）和10（P10）碳的烷基酯，研究了它们的氧化潜力、疏水性、抗自由基活性、对超氧阴离子（O2 °-）的抑制以及对白细胞产生次氯酸（HOCl）和抑制髓过氧化物酶（MPO）氯化活性的影响。这些酯的疏水性（logP，0.81-4.82）与其氧化潜力（0.222-0.298 V）之间没有显著关联。然而，除了P10外，这些酯在清除DPPH和过氧自由基方面比酸前体有效约2倍。这些酯对由活化的中性粒细胞（PMNs）和外周血单核细胞（PBMCs）释放的O2 °-具有强抑制作用。研究发现，碳链长度与相对抑制效力之间存在相关性。P7是最活跃的酯，其作为NADPH氧化酶抑制剂的效率约为阿波西宁的10倍。这些酯显著抑制了PMNs释放HOCl，这归因于对这些细胞中NADPH氧化酶活性的抑制。总之，作为有效的NADPH氧化酶抑制剂，儿茶酸酯类化合物在慢性炎症疾病治疗中显示出良好的前景。此外，这是首次证明，除了具有氧化还原活性的基团外，疏水性也可以作为NADPH氧化酶抑制剂设计的决定性因素。
• 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.