2-2'-ethanediylbis(3-hydroxy-6-(hydroxymethyl)-4H-pyran-4-one) | 148992-42-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2-2'-ethanediylbis(3-hydroxy-6-(hydroxymethyl)-4H-pyran-4-one)
• 英文别名: 1,1-bis-(3-hydroxy-6-hydroxymethyl-4-oxo-4H-pyran-2-yl)-ethane；1,1-Bis-(3-hydroxy-6-hydroxymethyl-4-oxo-4H-pyran-2-yl)-aethan；Dikojiacid B；3-hydroxy-2-[1-[3-hydroxy-6-(hydroxymethyl)-4-oxopyran-2-yl]ethyl]-6-(hydroxymethyl)pyran-4-one
• CAS: 148992-42-1
• 化学式: C₁₄H₁₄O₈
• 分子量: 310.26
• InChiKey: LTLNIJQADYJVTG-UHFFFAOYSA-N

物化性质

• 熔点：
  211.2-212 °C
• 沸点：
  675.3±55.0 °C(Predicted)
• 密度：
  1.646±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-2'-ethanediylbis(3-hydroxy-6-(hydroxymethyl)-4H-pyran-4-one) 、 乙酸酐 在 硫酸 作用下， 生成 1,1-bis-(3-acetoxy-6-acetoxymethyl-4-oxo-4H-pyran-2-yl)-ethane
  参考文献：
  名称：

  The Reaction of Kojic Acid with Aldehydes^1,2

  摘要：

  DOI：

  10.1021/ja01274a006
• 作为产物：
  描述：

  曲酸 在 ammonium hydroxide 、 乙醇 、 乙醛 作用下， 生成 2-2'-ethanediylbis(3-hydroxy-6-(hydroxymethyl)-4H-pyran-4-one)
  参考文献：
  名称：

  The Reaction of Kojic Acid with Aldehydes^1,2

  摘要：

  DOI：

  10.1021/ja01274a006

文献信息

• A family of hydroxypyrone ligands designed and synthesized as iron chelators
  作者：Leonardo Toso、Guido Crisponi、Valeria M. Nurchi、Miriam Crespo-Alonso、Joanna I. Lachowicz、M. Amelia Santos、Sergio M. Marques、Juan Niclós-Gutiérrez、Josefa M. González-Pérez、Alicia Domínguez-Martín、Duane Choquesillo-Lazarte、Zbigniew Szewczuk

  DOI：10.1016/j.jinorgbio.2013.06.009

  日期：2013.10

  The use of chelating agents for iron and aluminum in different clinical applications has found increasing attention in the last thirty years. Desferal, deferiprone and deferasirox, chelating agents nowadays in use, are based on hydroxamic groups, hydroxyl-substituted pyridinones or aromatic ring systems. With the aim of designing new chelators, we synthesized a series of kojic acid derivatives composed by two kojic units joined by linkers variously substituted. The huge advantages of these molecules are that they are easy and cheap to produce. Preliminary works on complex formation equilibria of the first group of ligands with iron and aluminium highlighted extremely good pMe values and gave evidence of the ability to scavenge iron from inside cells. On these bases a second set of bis-kojic ligands, whose linkers between the kojic chelating moieties are differentiated both in terms of type and size, has been designed, synthesized and characterized. The structural characterization of these new ligands is presented, and the protonation and iron(III) complex formation equilibria studied by potentiometry, UV-Visible spectrophotometry, electrospray ionization mass (ESI-MS) and H-1 NMR spectroscopy will be described and discussed. (C) 2013 Elsevier Inc. All rights reserved.