5-hydroxy-4-keto-2-pentenoic acid | 1261348-96-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 5-hydroxy-4-keto-2-pentenoic acid
• 英文别名: HKPA；5-HKPA；5-Hydroxy-4-keto-2-pentenoic acid；5-hydroxy-4-oxopent-2-enoic acid
• CAS: 1261348-96-2
• 化学式: C₅H₆O₄
• 分子量: 130.1
• InChiKey: JXKHAEWBGBMSSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-羟甲基糠醛 在 水 、 氧气 、 亚甲兰 作用下， 25.0 ℃ 、101.33 kPa 条件下， 生成 5-hydroxy-4-keto-2-pentenoic acid
  参考文献：
  名称：

  Production of 5-hydroxy-4-keto-2-pentenoic acid by photo-oxidation of 5-hydroxymethylfurfural with singlet oxygen: A kinetic investigation

  摘要：

  5-Hydroxy-4-keto-2-pentenoic acid (HKPA) is characterized by the presence in its chemical structure of four different chemical groups (hydroxyl, keto, carboxylic and Unsaturated groups) that tender it a possible intermediate or monomer in the chemical industry. The production of this compound is studied by the sensitized photo-oxidation of 5-hydroxymethylfurfural (5-HMF) in aqueous solution at acidic pH. 5-HMF can be easily obtained through the degradation of saccharides such as fructose or inulin.The system reactivity is influenced by the concentration of methylene blue (BM) which is used as the photosensitizer and the oxygen dissolved in the Solution. Only moderate consumptions of the sensitizer are recorded during the oxidation experiments thus Suggesting the possibility to recover and reuse it in new runs. No differences in the reactivity of the system and/or selectivity for HKPA are observed as a result of changes in the starting concentration of the Substrate and/or pH.A simplified reaction scheme of photo-oxidation of 5-HMF is proposed. Two kinetic models are developed according to this scheme to simulate the photo-oxidation processes of the substrate in the absence and in the presence of triethylene blue. A validation of these models is carried out by means of the experimental data, collected at pH = 6.0, at different initial concentrations of 5-HMF and BM. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2009.12.003

文献信息

• Production of 5-hydroxy-4-keto-2-pentenoic acid by photo-oxidation of 5-hydroxymethylfurfural with singlet oxygen: A kinetic investigation
  作者：Canterino Marisa、Di Somma Ilaria、Raffaele Marotta、Andreozzi Roberto、Caprio Vincenzo

  DOI：10.1016/j.jphotochem.2009.12.003

  日期：2010.2

  5-Hydroxy-4-keto-2-pentenoic acid (HKPA) is characterized by the presence in its chemical structure of four different chemical groups (hydroxyl, keto, carboxylic and Unsaturated groups) that tender it a possible intermediate or monomer in the chemical industry. The production of this compound is studied by the sensitized photo-oxidation of 5-hydroxymethylfurfural (5-HMF) in aqueous solution at acidic pH. 5-HMF can be easily obtained through the degradation of saccharides such as fructose or inulin.The system reactivity is influenced by the concentration of methylene blue (BM) which is used as the photosensitizer and the oxygen dissolved in the Solution. Only moderate consumptions of the sensitizer are recorded during the oxidation experiments thus Suggesting the possibility to recover and reuse it in new runs. No differences in the reactivity of the system and/or selectivity for HKPA are observed as a result of changes in the starting concentration of the Substrate and/or pH.A simplified reaction scheme of photo-oxidation of 5-HMF is proposed. Two kinetic models are developed according to this scheme to simulate the photo-oxidation processes of the substrate in the absence and in the presence of triethylene blue. A validation of these models is carried out by means of the experimental data, collected at pH = 6.0, at different initial concentrations of 5-HMF and BM. (C) 2009 Elsevier B.V. All rights reserved.