1,3,5-三羟基2-甲氧基苯 | 487-71-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 1,3,5-三羟基2-甲氧基苯
• 中文别名: 2-甲氧基苯-1,3,5-三醇
• 英文名称: Iretol
• 英文别名: 1,3,5-trihydroxy-2-methoxybenzene；2-methoxyphloroglucinol；2-Methoxybenzene-1,3,5-triol
• CAS: 487-71-8
• 化学式: C₇H₈O₄
• mdl: MFCD00597045
• 分子量: 156.138
• InChiKey: ASTPOGDWGNJVEW-UHFFFAOYSA-N

物化性质

• 溶解度：
  二甲基亚砜：62.5 mg/mL（400.28 mM）

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2909499000
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温密封，干燥保存。

制备方法与用途

生物活性方面，Iretol（2,4,6-三羟基苯甲醚）是从 Iris Jorentina 中获得的一种葡萄糖苷降解产物。Iretol 是合成天然异黄酮如 Tectorigenin、Irigenin 和 Caviunin 的中间体。

反应信息

• 作为反应物：
  描述：

  1,3,5-三羟基2-甲氧基苯 在 盐酸 、 三氟化硼乙醚 、 甲基磺酰氯 作用下， 以 乙醚 为溶剂， 反应 27.0h， 生成 鸢尾黄素
  参考文献：
  名称：

  Polyphenols based on isoflavones as inhibitors of Helicobacter pylori urease

  摘要：

  Twenty polyphenols were synthesized and evaluated for their effect on Helicobacter pylori urease. Among these compounds, 4-(p-hydroxyphenethyl)pyrogallol (15) (IC50 = 0.03 mM) and 7,8,4'-trihydroxyisoflavone (19) (IC50 = 0.14 mM) showed potent inhibitory activities, and inhibited Helicobacter pylori urease in a time-dependent manner. The structure-activity relationship of these polyphenols revealed: the two ortho hydroxyl groups were essential for inhibitory activity of polyphenol. When the C-ring of isoflavone was broken, the inhibitory activity markedly decreased. As for deoxybenzoin, the carboxyl group was clearly detrimental. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.03.045
• 作为产物：
  描述：

  2,4,6-三硝基苯甲醚 在 镍 盐酸 、 氢气 作用下， 生成 1,3,5-三羟基2-甲氧基苯
  参考文献：
  名称：

  异黄酮的合成。第五部分Irigenin和Tectorigenin

  摘要：

  合成异黄酮的一般乙氧基化方法已应用于合成irigenin（VII）和tectorigenin（XVI）。该合成途径也产生了异构体，ψ -irigenin（XI）和ψ -tectorigenin（XX）。讨论了有关某些乙氧基化反应中产物比例以及5,6,7-和5,7,8-三取代异黄酮的相对热力学稳定性的信息。

  DOI：

  10.1039/j39700001219

文献信息

• PROCESS FOR STRAIGHTENING KERATIN FIBRES WITH A HEATING MEANS AND DENATURING AGENTS
  申请人：Philippe Michel

  公开号：US20100028280A1

  公开（公告）日：2010-02-04

  The invention relates to a process for straightening keratin fibres, comprising: (i) a step in which a straightening composition containing at least two denaturing agents is applied to the keratin fibres, (ii) a step in which the temperature of the keratin fibres is raised, using a heating means, to a temperature of between 110 and 250° C.

  该发明涉及一种直发角蛋白纤维的拉直过程，包括：(i)将至少两种变性剂含有的拉直组合物涂抹到角蛋白纤维上的步骤，(ii)使用加热装置将角蛋白纤维的温度升高至110至250°C的步骤。
• METHOD FOR PREPARING HISPIDULIN AND ITS DERIVATIVES
  申请人：TAIPEI MEDICAL UNIVERSITY

  公开号：US20190322637A1

  公开（公告）日：2019-10-24

  Provided is a method for preparing hispidulin or a derivative thereof. The method includes selective protection of trihydroxybenzaldehyde, followed by regioselective iodination, selective protection, Stille coupling, Baeyer-Villiger oxidation and basic hydrolysis to obtain a protected intermediate compound. Then, alkylation, Claisen-Schmidt condensation, cyclization and deprotection of the protected intermediate compound are performed to obtain hispidulin or the derivative thereof. The present disclosure provides an efficient method for total synthesis of hispidulin or the derivative thereof with concise reaction steps and high yield.

  提供了一种制备hispidulin或其衍生物的方法。该方法包括选择性保护三羟基苯甲醛，然后进行选择性碘化、选择性保护、Stille偶联、Baeyer-Villiger氧化和碱性水解，以获得一种受保护的中间化合物。然后，进行烷基化、Claisen-Schmidt缩合、环化和去保护受保护中间化合物，以获得hispidulin或其衍生物。本公开提供了一种高效的hispidulin或其衍生物的全合成方法，具有简洁的反应步骤和高产率。
• Method for straightening keratinous fibers using heating means and an aromatic compound
  申请人：L'Oreal

  公开号：US11044978B2

  公开（公告）日：2021-06-29

  The invention concerns a method for straightening keratinous fibers including: (i) a step of applying on the keratinous fibers a hair straightening composition containing at least one polyhydroxylated aromatic compound, (ii) a step of increasing the temperature of the keratinous fibers, using heating means, to a temperature ranging between 110 and 250° C.

  本发明涉及一种拉直角质纤维的方法，包括：(i) 在角质纤维上涂抹含有至少一种多羟基芳香族化合物的拉直头发组合物，(ii) 使用加热装置将角质纤维的温度提高到 110 至 250 摄氏度之间。
• Chapman; Perkin; Robinson, Journal of the Chemical Society, 1927, p. 3020
  作者：Chapman、Perkin、Robinson

  DOI：——

  日期：——
• Total Synthesis of Hispidulin and the Structural Basis for Its Inhibition of Proto-oncogene Kinase Pim-1
  作者：Shi-Wei Chao、Ming-Yuan Su、Lih-Chu Chiou、Liang-Chieh Chen、Chung-I Chang、Wei-Jan Huang

  DOI：10.1021/acs.jnatprod.5b00324

  日期：2015.8.28

  A new method is applied to synthesize hispidulin, a natural flavone with a broad spectrum of biological activities. Hispidulin exhibits inhibitory activity against the oncogenic protein kinase Pim-1. Crystallographic analysis of Pim-1 bound to hispidulin reveals a binding mode distinct from that of quercetin, suggesting that the binding potency of flavonoids is determined by their hydrogen-bonding interactions with the hinge region of the kinase. Overall, this work may facilitate construction of a library of hispidulin-derived compounds for investigating the structure activity relationship of flavone-based Pim-1 inhibitors.