2',4',3-trihydroxychalcone | 42220-83-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2',4',3-trihydroxychalcone
• 英文别名: 3,2',4'-Trihydroxy-chalkon；1-(2,4-Dihydroxyphenyl)-3-(3-hydroxyphenyl)prop-2-en-1-one；1-(2,4-dihydroxyphenyl)-3-(3-hydroxyphenyl)prop-2-en-1-one
• CAS: 42220-83-7
• 化学式: C₁₅H₁₂O₄
• 分子量: 256.258
• InChiKey: WKMQGQZPDSFACZ-UHFFFAOYSA-N

物化性质

• 熔点：
  182 °C
• 沸点：
  526.0±50.0 °C(Predicted)
• 密度：
  1.384±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• 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',4',3-trihydroxychalcone 在 双氧水 作用下， 以 sodium hydroxide 为溶剂， 反应 2.0h， 生成 3,7-dihydroxy-2-(3-hydroxyphenyl)-4H-chromen-4-one
  参考文献：
  名称：

  On the antioxidant properties of three synthetic flavonols

  摘要：

  评估了一系列合成和天然类黄酮对酶促产生的含氧物质超氧阴离子（O2·—）的抗氧化特性。7-羟基黄酮、7,3′-二羟基黄酮和3′-羟基黄酮在C3、C7、C3′和C4′位置上的羟基取代存在系统变化，并分别与已鉴定的天然类黄酮槲皮素、山奈酚和芦丁的抗氧化能力进行了比较。类黄酮对O2·—的失活效率与其各自的氧化电位无关，表明O2·—淬灭的纯一电子转移机制可能不是主要的清除过程。实验证据表明，类黄酮对O2·—生成酶系统的可能抑制作用不应被视为氧化物质抑制的间接原因。抑制O2·—的一种可能机制高度依赖于类黄酮的取代模式，可能与生成过氧化氢或二氧杂环丁烷作为氧化产物有关，正如其他生物相关化合物所假设的那样。类黄酮骨架上C3和C7位置同时发生羟基取代在增强O2·—抑制作用方面起着决定性作用。C7位置上的羟基被O-芦丁基取代会抑制这种作用，而7位置没有羟基会显著降低抗氧化能力。最后，3′和4′位置上的羟基不会

  DOI：

  10.1691/ph.2007.1.6559
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 、 间羟基苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 2.17h， 以65.2%的产率得到2',4',3-trihydroxychalcone
  参考文献：
  名称：

  Natural product-based design, synthesis and biological evaluation of 2′,3,4,4′-tetrahydrochalcone analogues as antivitiligo agents

  摘要：

  A bioactive component, 2',3,4,4'-tetrahydrochalcone (RY3-a) was first isolated from Vernohia anthelmintica (L.) willd seeds, and a set of its analogs, RY3-a-1-RY3-a-15 and RY3-c were designed and synthesized. Biological activity assays showed that RY3-c exhibited better melanogenesis and antioxidant activity and lower toxicity in comparison with RY3-a and butin. Further study tests showed that RY3-c exhibited better melanogenesis activity compared with the positive control 8-methoxypsoralan (8-MOP) in a vitiligo mouse model, suggesting that RY3-c is a good candidate antivitiligo agent. Mechanistic studies showed that RY3-c could repair cell damage induced by excessive oxidative stress and may exert melanin synthesis activity in the mouse melanoma B16F10 cell line by activating the mitogen-activated protein kinase (MAPK) pathway and the upregulation of c-kit.

  DOI：

  10.1016/j.bioorg.2019.03.054

文献信息

• Chalcones as Analytical Reagents of Aluminum: Stability, Thermodynamic and Kinetic Study
  作者：Vanesa A. Muñoz、Carolina G. Kretek、M. Paulina Montaña、Nora  B. Pappano、Nora  B. Debattista、Gabriela V. Ferrari

  DOI：10.1515/zpch-2014-0617

  日期：2015.3.28

  Chalcones, a group of polyphenolic compounds, has been studied for a long time due to their biological properties and their ability as analytical reagents. In this work the stability and thermodynamic parameters concerning the fotmation in ethanolic medium of two chalcone–aluminium complexes (2′,3-dihydroxychalcone-Al(III) and 2′,4′,3-trihydroxychalcone-Al(III)) were studied and a kinetic study of the formation reaction was aslo performed. Both systems showed 1:1 L : M stoichiometry and stability constants at four temperatures were determined. Thermodynamic parameters indicate that both formation reactions are endothermic and driving force is entropic. Kinetic study revealed that 2′,4′,3-trihydroxychalcone-Al(III) formation is faster than 2′,3-dihydroxyclacone-Al(III), a factor which can be interesting when proposing new analytical reagents.

  查尔酮是一类多酚化合物，由于其生物性质和作为分析试剂的能力而被长期研究。本研究探讨了两种查尔酮铝络合物（2'，3-二羟基查尔酮-Al（III）和2'，4'，3-三羟基查尔酮-Al（III））在乙醇介质中的稳定性和热力学参数，并进行了形成反应的动力学研究。两个系统均显示了1：1 L：M化学计量比，并确定了四个温度下的稳定常数。热力学参数表明，两种形成反应均为吸热反应，驱动力是熵增。动力学研究表明，2'，4'，3-三羟基查尔酮-Al（III）的形成速度比2'，3-二羟基查尔酮-Al（III）快，这一因素在提出新的分析试剂时可能很有趣。

• Calcium Hydroxide Is an Efficient Catalyst for Synthesis of Polyhydroxy Chalcones
  作者：P. S. Kulkarni、P. M. Swami、P. K. Zubaidha

  DOI：10.1080/15533174.2012.752392

  日期：2013.1.1

  Calcium hydroxide was found to be an efficient catalyst for synthesis of polyhydroxy chalcones. This method has been employed to synthesize various 2,4-dihydroxychalcones having various substituents on the B ring. The merits of this method include shorter reaction time, inexpensive and easily available catalyst, high yield, and easy workup compared to other reported methods.
• Design and synthesis of 3,5-diaryl-4,5-dihydro-1H-pyrazoles as new tyrosinase inhibitors
  作者：Zhixuan Zhou、Jiaru Zhuo、Sujun Yan、Lin Ma

  DOI：10.1016/j.bmc.2012.12.054

  日期：2013.4

  In this study, twenty 3,5-diaryl-4,5-dihydro-1H-pyrazole derivatives with hydroxyl(s) (1a-1p, 2a-2d) were synthesized and their inhibitory activity on mushroom tyrosinase was examined. The results showed that among these compounds, 1-(5-(3,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone 1d was found to be the most potent tyrosinase inhibitor with IC50 value of 0.301 mu M. Kinetic study revealed that these compounds were competitive inhibitors of tyrosinase and their structure-activity relationships were investigated in this article. (C) 2013 Published by Elsevier Ltd.
• Tambor, Chemische Berichte, 1916, vol. 49, p. 1708
  作者：Tambor

  DOI：——

  日期：——
• Novel Synthesis of 3,3′-Dihydroxyflavone and Apparent Formation Constants of Flavonoid−Ga(III) Complexes
  作者：Gabriela V. Ferrari、Nora B. Pappano、M. Paulina Montaña、Norman A. García、Nora B. Debattista

  DOI：10.1021/je901091f

  日期：2010.9.9

  Flavonoids are a wide variety of polyphenolic compounds. They have many biological properties. They also exhibit a metallic ion complexation capacity, which is important since it has been found that biological properties these ligands present can be enhanced when complexation occurs. In this work four flavonoid-Ga(III) complexes were studied: 2',4',3-trihydroxychalcone-Ga(III), 2',3-dihydroxychalcone-Ga(III), 3,7,3'-trihydroxyflavone-Ga(III), and 3,3'-dihydroxyflavone-Ga(III). All ligands were synthesized by our working group, contributing a novel, cheaper, and more simple way to obtain 3,3'-dihydroxyflavone. The stoichiometry of the complexes was determined using the Yoe-Jones method. Both chalcone-Ga(III) complexes presented 1: 1 L:M stoichiometry; meanwhile flavone-Ga(III) complexes presented 2:1 L:M stoichiometry. The pK values were determined by means of a spectrophotometric method. Values obtained were: 2',4',3-trihydroxychalcone-Ga(M), pK = 4.35 +/- 0.38; 2',3-dihydroxychalcone-Ga(III), pK = 3.40 +/- 0.17; 3,7,3'-trihydroxyflavone-Ga(III), pK = 7.74 +/- 0.19; and 3,3'-dihydroxyflavone-Ga(III), pK = 8.46 +/- 0.27.