3,5-二羟基-4-(苯基甲氧基)苯甲酸 | 100622-15-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3,5-二羟基-4-(苯基甲氧基)苯甲酸
• 英文名称: 3,5-dihydroxy-4-(phenylmethoxy)benzoic acid
• 英文别名: 4-(benzyloxy)-3,5-dihydroxybenzoic acid；4-Benzyloxy-3,5-dihydroxy-benzoesaeure；3,5-Dihydroxy-4-phenylmethoxybenzoic acid
• CAS: 100622-15-9
• 化学式: C₁₄H₁₂O₅
• 分子量: 260.246
• InChiKey: VXINPVWEXXYCFC-UHFFFAOYSA-N

物化性质

• 熔点：
  170 °C(Solv: water (7732-18-5); methanol (67-56-1))
• 沸点：
  509.3±50.0 °C(Predicted)
• 密度：
  1.417±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,5-二羟基-4-(苯基甲氧基)苯甲酸 在 palladium on activated charcoal 吡啶 、 lithium aluminium tetrahydride 、 氯化亚砜 、 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 丙酮 、 甲苯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 32.0h， 生成 2,6-Dibutoxy-4-dimethylaminomethyl-phenol
  参考文献：
  名称：

  Benzylamine antioxidants: relationship between structure, peroxyl radical scavenging, lipid peroxidation inhibition and cytoprotection

  摘要：

  Three homologous series of 3,5-dialkoxy-4-hydroxybenzylamines were prepared and tested (1) as peroxyl radical scavengers in homogeneous aqueous solution, (2) as inhibitors of iron-dependent peroxidation of rabbit brain vesicular membrane lipids, and (3) as cytoprotective agents using primary cultures of rat hippocampal neurons exposed to hydrogen peroxide. The structural requirements for efficient radical trapping in homogeneous solution differed from those for effective lipid peroxidation inhibition: In homogeneous solution a kinetic preference existed for smaller, less sterically encumbered substituents flanking the reactive phenolic hydroxyl group. Lipid peroxidation inhibition, on the other hand, required longer more lipophilic substituents. Consequently, a lipophilic alkoxyl substituent at C3 and a small substituent at C5 appeared optimal for efficient radical scavenging activity in both lipid and homogeneous solution. Maximal cytoprotection of rat hippocampal neurons exposed to hydrogen peroxide was also associated with more lipophilic derivatives although substituent length and substituent bulk may represent independent parameters for relating structure and efficacy in this system.

  DOI：

  10.1021/jm00061a018
• 作为产物：
  描述：

  没食子酸甲酯 在 sodium hydroxide 、 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 19.17h， 生成 3,5-二羟基-4-(苯基甲氧基)苯甲酸
  参考文献：
  名称：

  Benzylamine antioxidants: relationship between structure, peroxyl radical scavenging, lipid peroxidation inhibition and cytoprotection

  摘要：

  Three homologous series of 3,5-dialkoxy-4-hydroxybenzylamines were prepared and tested (1) as peroxyl radical scavengers in homogeneous aqueous solution, (2) as inhibitors of iron-dependent peroxidation of rabbit brain vesicular membrane lipids, and (3) as cytoprotective agents using primary cultures of rat hippocampal neurons exposed to hydrogen peroxide. The structural requirements for efficient radical trapping in homogeneous solution differed from those for effective lipid peroxidation inhibition: In homogeneous solution a kinetic preference existed for smaller, less sterically encumbered substituents flanking the reactive phenolic hydroxyl group. Lipid peroxidation inhibition, on the other hand, required longer more lipophilic substituents. Consequently, a lipophilic alkoxyl substituent at C3 and a small substituent at C5 appeared optimal for efficient radical scavenging activity in both lipid and homogeneous solution. Maximal cytoprotection of rat hippocampal neurons exposed to hydrogen peroxide was also associated with more lipophilic derivatives although substituent length and substituent bulk may represent independent parameters for relating structure and efficacy in this system.

  DOI：

  10.1021/jm00061a018

文献信息

• Synthetic Studies toward C-Glucosidic Ellagitannins: A Biomimetic Total Synthesis of 5-O-Desgalloylepipunicacortein A
  作者：Gaëlle Malik、Anna Natangelo、Jaime Charris、Laurent Pouységu、Stefano Manfredini、Dominique Cavagnat、Thierry Buffeteau、Denis Deffieux、Stéphane Quideau

  DOI：10.1002/chem.201200517

  日期：2012.7.16

  5‐O‐desgalloylepipunicacortein A (1 β) was achieved by either using the natural ellagic acid bis‐lactone as a precursor of the requested HHDP unit or by implementing an atroposelective intramolecular oxidative biarylic coupling to forge this HHDP unit. Both routes converged in the penultimate step of this synthesis to enable a biomimetic formation of the key C‐aryl glucosidic bond in the title compound.

  C-葡糖苷鞣花单宁是具有强抗氧化性能的生物活性多酚天然产物的一个子类，以及与它们与功能蛋白和结构蛋白相互作用的能力有关的有希望的抗肿瘤和抗病毒活性。迄今为止，大多数针对鞣花单宁的合成研究都涉及吡喃葡糖苷类。正在开发一种合成策略以获取C葡糖苷鞣花单宁，其特征结构特征包括通过C芳基葡糖苷键与开链葡萄糖核连接的促转异构六氢二苯甲酰基（HHDP）或九羟基二苯甲酰（NHTP）单元。本文所述。含二元HHDP的5- O的总合成通过使用天然鞣花酸双内酯作为要求的HHDP单元的前体或通过实施熵选择性分子内氧化双芳基偶合以锻造该HHDP单元，可以实现desgalloylepipunicacortein A（1β）。两种途径都在该合成的倒数第二个步骤中收敛，从而能够在目标化合物中仿生形成关键的C-芳基糖苷键。
• Bioinspired Total Synthesis of (−)-Vescalin: A Nonahydroxytriphenoylated<i>C</i>-Glucosidic Ellagitannin
  作者：Antoine Richieu、Philippe A. Peixoto、Laurent Pouységu、Denis Deffieux、Stéphane Quideau

  DOI：10.1002/anie.201707613

  日期：2017.10.23

  first total synthesis of the 2,3,5‐O‐(S,R)‐nonahydroxytriphenoylated (NHTP) C‐glucosidic ellagitannin (−)‐vescalin was accomplished through a series of transformations mimicking the sequence of events leading to its biogenesis. The key steps of this synthesis encompass a Wittig‐mediated ring opening of a glucopyranosic hemiacetal, a C‐glucosidation event through a phenolic aldol‐type reaction, and a W

  2,3,5 - O-（S，R）-壬羟基三苯甲酰化（NHTP）C-葡萄糖苷鞣花单宁（-）-维斯卡林的第一个全合成是通过模拟导致其生物发生的事件序列的一系列转化来完成的。该合成的关键步骤包括维蒂希介导的吡喃葡萄糖半缩醛的开环，通过酚醛羟型反应进行的C-葡萄糖苷化事件以及Wynberg-Feringa-Yamada型氧化酚醛偶联，其锻造了NHTP单元。 （-）-维斯卡林
• Plant Polyphenols. VI. Experiments on the Synthesis of 3,3'- and 4,4'-Di-O-Methylellagic Acid¹
  作者：Leonard Jurd

  DOI：10.1021/ja01526a039

  日期：1959.9
• [EN] GALLIC ACID DERIVATIVES, METHOD FOR THEIR PREPARATION AND THEIR USE AS DRUGS<br/>[FR] DERIVES DE L'ACIDE GALLIQUE, LEUR PROCEDE DE PREPARATION ET LEUR APPLICATION A TITRE DE MEDICAMENTS
  申请人：ROUSSEL UCLAF

  公开号：WO1996008483A1

  公开（公告）日：1996-03-21

  (EN) Products of formula (ID), in which R1 is hydrogen, carboxy, formyl, alkyl, hydroxyalkyl, alkoxyalkyl, carbamoyl, N-alkyl-carbamoyl, NNdialkylcarbamoyl, alkoxycarbothioate or alkylcarbonyl, V1 is oxygen or -NH-, V2 is -V1H or hydrogen and A is optionally substituted alkyl or aryl, the products of formula (ID) being in all the possible isomeric forms. The invention also concerns the acid addition salts and bases of the products of formula (ID).(FR) L'invention a pour objet les produits de formule (ID), dans laquelle R1 représente hydrogène, carboxy, formyle, alkyle, hydroxyalkyle, alcoxyalkyle, carbamoyle, N-alkyl-carbamoyle, NNdialkylcarbamoyle, alcoxycarbothioate ou alkylcarbonyle, V1 représente oxygène ou -NH-, V2 représente -V1H ou hydrogène et A représente alkyle ou aryle éventuellement substitués, lesdits produits de formule (ID) étant sous toutes les formes isomères possibles ainsi que les sels d'addition avec les acides et les bases desdits produits de formule (ID).
• Benzylamine antioxidants: relationship between structure, peroxyl radical scavenging, lipid peroxidation inhibition and cytoprotection
  作者：Melvin J. Yu、Jefferson R. McCowan、Lee A. Phebus、Richard D. Towner、Peter P. K. Ho、Priscilla T. Keith、Charlotte A. Luttman、Royal D. Saunders、Kenneth J. Ruterbories

  DOI：10.1021/jm00061a018

  日期：1993.4

  Three homologous series of 3,5-dialkoxy-4-hydroxybenzylamines were prepared and tested (1) as peroxyl radical scavengers in homogeneous aqueous solution, (2) as inhibitors of iron-dependent peroxidation of rabbit brain vesicular membrane lipids, and (3) as cytoprotective agents using primary cultures of rat hippocampal neurons exposed to hydrogen peroxide. The structural requirements for efficient radical trapping in homogeneous solution differed from those for effective lipid peroxidation inhibition: In homogeneous solution a kinetic preference existed for smaller, less sterically encumbered substituents flanking the reactive phenolic hydroxyl group. Lipid peroxidation inhibition, on the other hand, required longer more lipophilic substituents. Consequently, a lipophilic alkoxyl substituent at C3 and a small substituent at C5 appeared optimal for efficient radical scavenging activity in both lipid and homogeneous solution. Maximal cytoprotection of rat hippocampal neurons exposed to hydrogen peroxide was also associated with more lipophilic derivatives although substituent length and substituent bulk may represent independent parameters for relating structure and efficacy in this system.