2-hydroxy-3-(4-hydroxyphenyl)acrylic acid | 52178-61-7

• 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: 2-hydroxy-3-(4-hydroxyphenyl)acrylic acid
• 英文别名: p-hydroxyphenylpyruvic acid；3-(4-Hydroxyphenyl)benztraubensaeure；(Z)-2,p-dihydroxycinnamic acid；(Z)-2-hydroxy-3-(4-hydroxyphenyl)acrylic acid；para,α-Dihydroxyzimtsaeure；2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid；(Z)-2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoic acid
• CAS: 52178-61-7
• 化学式: C₉H₈O₄
• 分子量: 180.16
• InChiKey: GQYBCIHRWMPOOF-YVMONPNESA-N

物化性质

• 沸点：
  408.5±45.0 °C(Predicted)
• 密度：
  1.491±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-hydroxy-3-(4-hydroxyphenyl)acrylic acid 在 盐酸 、 汞 、 锌 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以78%的产率得到DL-4-羟基苯乳酸
  参考文献：
  名称：

  A Modified Synthesis of (±)-β-Aryllactic acids

  摘要：

  据报道，丹参中活性成分的外消旋形式，即（±）-ß-(3,4-二羟基苯基)乳酸[(±)-3-(3,4-二羟基苯基)-2-羟基丙酸]及其七种外消旋衍生物已成功合成。

  DOI：

  10.1055/s-1992-26228
• 作为产物：
  描述：

  DL-酪氨酸 在 盐酸 、 4-二甲氨基吡啶 、 三氟乙酸酐 作用下， 生成 2-hydroxy-3-(4-hydroxyphenyl)acrylic acid
  参考文献：
  名称：

  Klein, Christian; Schulz, Guenter; Steglich, Wolfgang, Liebigs Annalen der Chemie, 1983, # 9, p. 1638 - 1639

  摘要：

  DOI：

文献信息

• [EN] AZETIDINE AND CYCLOBUTANE DERIVATIVES AS JAK INHIBITORS<br/>[FR] DÉRIVÉS D'AZÉTIDINE ET DE CYCLOBUTANE EN TANT QU'INHIBITEURS DE JANUS KINASE (JAK)
  申请人：INCYTE CORP

  公开号：WO2009114512A1

  公开（公告）日：2009-09-17

  The method includes the steps of performing in-vitro liver, intestinal and/or expressed enzyme assays with selected ethnobotanical substances, for both humans and a variety of animal species, to produce an array of resulting chemical entities, such as metabolites, for the human and the animals. Comparisons are then made between the chemical entities from the human in-vitro studies and the animal in-vitro studies to determine the closest match. The animal with the closest match is then used for an in-vivo study. If a match is present between the animal in-vivo results and the human in-vitro results, the matched chemical entity is isolated or synthesized and then further tested to determine the suitability of the matched chemical entity as a treatment drug.

  该方法包括以下步骤：使用选择的民族植物物质进行体外肝脏、肠道和/或表达酶测定，针对人类和多种动物物种，以产生一系列化学实体，如代谢物，用于人类和动物。然后将人体体外研究和动物体外研究得到的化学实体进行比较，以确定最接近的匹配。然后选择最接近匹配的动物进行体内研究。如果动物体内结果与人体体外结果相匹配，则分离或合成匹配的化学实体，并进一步测试以确定匹配的化学实体是否适用于治疗药物。
• Synthesis and Biological Evaluation of Analogues of Butyrolactone I as PTP1B Inhibitors
  作者：Bihong Hong、Jianlin He、Chaochun Fan、Chao Tang、Qingqing Le、Kaikai Bai、Siwen Niu、Meitian Xiao

  DOI：10.3390/md18110526

  日期：——

  metabolites of marine microorganisms. Butyrolactone I was found to be produced by Aspergillus terreus isolated from several marine-derived samples. The hypoglycemic activity of butyrolactone I has aroused our great interest. In this study, we synthesized six racemic butenolide derivatives (namely BL-1–BL-6) by modifying the C-4 side chain of butyrolactone I. Among them, BL-3 and BL-5 improved the insulin

  近年来，已经从海洋微生物的次生代谢物中分离出了许多含有丁烯内酯官能团的药理活性化合物。发现丁内酯由土曲霉产生从几个海洋样本中分离出来。丁内酯I的降血糖活性引起了我们的极大兴趣。在这项研究中，我们通过修饰丁内酯I的C-4侧链合成了六种外消旋丁烯内酯衍生物（即BL-1–BL-6）。其中BL-3和BL-5改善了HepG2细胞的胰岛素抵抗，并不影响RIN-m5f细胞系的增殖，这表明BL-3和BL-5的功效和安全性。此外，BL-3，BL-4，BL-5和BL-6表现出显着的蛋白质酪氨酸磷酸酶1B（PTP1B）抑制作用，而BL-3的对映异构体表现出不同的50％百分比抑制浓度（IC 50）针对PTP1B的值。BLs和PTP1B分子对接模拟的结果解释了BL-3对映异构体之间观察到的生物学结果的差异，该对映异构体支持BLs作为PTP1B抑制剂，并且还表明C-4的手性可能会影响Cb-1的抑制作用BL。我们的发现
• Corrosion inhibitor-drag reducer combinations
  申请人：——

  公开号：US20020063241A1

  公开（公告）日：2002-05-30

  Drag reducers having the formula: 1 where R 1 is a straight or branched saturated alkyl having at least 12 carbon atoms; R 2 , R 3 and R 4 are independently lower alkyl of 1 to 4 carbon atoms, aryl, alkylaryl, or alkoxide where the alkoxide units constitute from 1 to 16 alkoxy moieties where the alkoxy moieties are independently from 2 to 4 carbon atoms, or any two of R 2 , R 3 and R 4 are joined together to form cycloalkyl of 5 to 6 carbon atoms, or all three of R 2 , R 3 and R 4 together with the N form a pyridinium ring, where R 2 , R 3 and R 4 may be independently substituted with O or S; and X − is selected from the group of anions consisting of salicylate, thiosalicylate, sulfonate, and hydroxynaphthenate, have been found to simultaneously function as corrosion inhibitors. Cetyltrimethylammonium salicylate (CTAS) and Cetylpyridinium salicylate (CPS) are particularly preferred drag reducers.

  减阻剂的计算公式为 1 其中 R 1 是至少有 12 个碳原子的直链或支链饱和烷基； R 2 , R 3 和 R 4 独立地为 1 至 4 个碳原子的低级烷基、芳基、烷芳基或烷氧基，其中烷氧基单元构成 1 至 16 个烷氧基，其中烷氧基独立地为 2 至 4 个碳原子，或任意两个 R 2 , R 3 和 R 4 连接在一起形成 5 至 6 个碳原子的环烷基，或所有三个 R 2 , R 3 和 R 4 与 N 一起形成一个吡啶鎓环，其中 R 2 , R 3 和 R 4 可独立地被 O 或 S 取代；以及 X - 选自由水杨酸盐、硫代水杨酸盐、磺酸盐和羟基环烷酸盐组成的阴离子组、 已被发现同时具有缓蚀剂的功能。十六烷基三甲基水杨酸铵（CTAS）和十六烷基吡啶水杨酸铵（CPS）是特别理想的减阻剂。
• Corrosion inhibitor-drag reducer compounds
  申请人：——

  公开号：US20040206937A1

  公开（公告）日：2004-10-21

  Drag reducers having the formula: 1 where R 1 is a straight or branched saturated alkyl having at least 12 carbon atoms; R 2 , R 3 and R 4 are independently lower alkyl of 1 to 4 carbon atoms, aryl, alkylaryl, or alkoxide where the alkoxide units constitute from 1 to 16 alkoxy moieties where the alkoxy moieties are independently from 2 to 4 carbon atoms, or any two of R 2 , R 3 and R 4 are joined together to form cycloalkyl of 5 to 6 carbon atoms, or all three of R 2 , R 3 and R 4 together with the N form a pyridinium ring, where R 2 , R 3 and R 4 may be independently substituted with O or S; and X − is selected from the group of anions consisting of salicylate, thiosalicylate, sulfonate, and hydroxynaphthenate, have been found to simultaneously function as corrosion inhibitors. Cetyltrimethylammonium salicylate (CTAS) and Cetylpyridinium salicylate (CPS) are particularly preferred drag reducers.

  减阻剂的计算公式为 1 其中 R 1 是至少有 12 个碳原子的直链或支链饱和烷基； R 2 , R 3 和 R 4 独立地为 1 至 4 个碳原子的低级烷基、芳基、烷芳基或烷氧基，其中烷氧基单元构成 1 至 16 个烷氧基，其中烷氧基独立地为 2 至 4 个碳原子，或任意两个 R 2 , R 3 和 R 4 连接在一起形成 5 至 6 个碳原子的环烷基，或所有三个 R 2 , R 3 和 R 4 与 N 一起形成一个吡啶鎓环，其中 R 2 , R 3 和 R 4 可独立地被 O 或 S 取代；以及 X - 选自由水杨酸盐、硫代水杨酸盐、磺酸盐和羟基环烷酸盐组成的阴离子组、 已被发现同时具有缓蚀剂的功能。十六烷基三甲基水杨酸铵（CTAS）和十六烷基吡啶水杨酸铵（CPS）是特别理想的减阻剂。
• New 3- and 4-hydroxyfuranones as anti-oxidants and anti-inflammatory agents
  作者：Valérie Weber、Catherine Rubat、Eliane Duroux、Claire Lartigue、Michel Madesclaire、Pascal Coudert

  DOI：10.1016/j.bmc.2005.04.055

  日期：2005.7

  Two series of new furationes substituted by methylsulfonylphenyl or methylsulfamidophenyl moieties were found to protect against oxidation damage by inhibiting or quenching free radicals and reactive oxygen species in in vitro experiments. The effect on lipid peroxidation was also examined. In addition, we investigated the activity of products in two models of inflammation: phorbol ester-induced ear edema in mice and carrageenan-induced paw edema in rat. The most powerful compounds and with reducing activity against DPPH (IC50 = 1779 and 57 mu M, respectively), superoxide anion quenching capacity (IC50 = 511 and 49 mu M, respectively), lipid peroxidation inhibitory effect and anti-inflammatory properties (about 50-65% inhibition of edema at 200 mg/kg ip in both tests used) were selected for further pharmacological and toxicological tests because of their attractive profile for the treatment of inflammatory diseases. (c) 2005 Elsevier Ltd. All rights reserved.

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