3,4-二羟基苯甲酸3-O-beta-D-葡糖苷酸 | 953037-17-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 中文名称: 3,4-二羟基苯甲酸3-O-beta-D-葡糖苷酸
• 中文别名: 3,4-二羟基苯甲酸3-O-Β-D-葡萄糖醛酸
• 英文名称: 1-O-(2-hydroxy-5-carboxyphenyl)-β-D-glucuronic acid
• 英文别名: 3,4-dihydroxybenzoic acid 3-O-glucuronide；5-carboxy-2-hydroxyphenyl-β-D-glucopyranosiduronic acid；3,4-Dihydroxybenzoic acid 3-O-beta-D-glucuronide；(2S,3S,4S,5R,6S)-6-(5-carboxy-2-hydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 953037-17-7
• 化学式: C₁₃H₁₄O₁₀
• 分子量: 330.248
• InChiKey: CXNFDJSOAJNKSU-CDHFTJPESA-N

物化性质

• 熔点：
  >123°C (dec.)
• 沸点：
  717.5±60.0 °C(Predicted)
• 密度：
  1.822±0.06 g/cm3(Predicted)
• 溶解度：
  甲醇（微溶）、水（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  174
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  3,4,6-三邻乙酰基-alpha-D-吡喃葡萄糖 1,2-(原酸甲酯) 在 三氟化硼乙醚 、 水 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， -20.0~20.0 ℃ 、101.33 kPa 条件下， 反应 76.0h， 生成 3,4-二羟基苯甲酸3-O-beta-D-葡糖苷酸
  参考文献：
  名称：

  Flavonoid metabolism: the synthesis of phenolic glucuronides and sulfates as candidate metabolites for bioactivity studies of dietary flavonoids

  摘要：

  Epidemiological studies indicate that flavonoid intake is inversely associated with the risk of coronary heart disease, yet the mechanisms responsible for their bioactivity are still a matter of debate. Based on the rapid and extensive metabolism of most flavonoids, their health effects most likely result from the biological activity of their metabolites. However, a lack of commercially available compounds/standards has prevented the study of metabolite bioactivity and resulted in a focus on non-physiologically relevant precursor/parent structures. This paper details the synthesis of a series of phenolic glucuronide 1a-e and sulfate 2a-e derivates as candidate metabolites for use as reference compounds in metabolic profiling studies and for the exploration of flavonoid bioactivity. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2012.03.100

文献信息

• Synthesis of New Sulfated and Glucuronated Metabolites of Dietary Phenolic Compounds Identified in Human Biological Samples
  作者：A. Filipa Almeida、Cláudia N. Santos、M. Rita Ventura

  DOI：10.1021/acs.jafc.6b05629

  日期：2017.8.9

  standards has hampered the study of metabolite bioactivity and the exact structural confirmation in biological samples. New (poly)phenol metabolites previously identified in human samples after the intake of berry juice were chemically synthesized. Efficient chemical reactions were performed with moderate to excellent yields and selectivities. These new compounds could be used as standard chemicals

  （多）酚是水果和蔬菜中的一大类饮食化合物；它们的食用与有益健康有关。摄入后，（多）苯酚遭受广泛的代谢，其代谢产物的鉴定是一个新兴领域，因为这些代谢产物被认为是人类有机体中有效的生物活性分子。然而，缺乏可商购的标准阻碍了代谢物生物活性的研究以及生物样品中确切的结构确认。摄入浆果汁后，先前在人体样品中鉴定出的新的（多）苯酚代谢物是化学合成的。以中等至极好的产率和选择性进行了有效的化学反应。
• Flavonoid metabolism: the synthesis of phenolic glucuronides and sulfates as candidate metabolites for bioactivity studies of dietary flavonoids
  作者：Qingzhi Zhang、K. Saki Raheem、Nigel P. Botting、Alexandra M.Z. Slawin、Colin D. Kay、David O'Hagan

  DOI：10.1016/j.tet.2012.03.100

  日期：2012.6

  Epidemiological studies indicate that flavonoid intake is inversely associated with the risk of coronary heart disease, yet the mechanisms responsible for their bioactivity are still a matter of debate. Based on the rapid and extensive metabolism of most flavonoids, their health effects most likely result from the biological activity of their metabolites. However, a lack of commercially available compounds/standards has prevented the study of metabolite bioactivity and resulted in a focus on non-physiologically relevant precursor/parent structures. This paper details the synthesis of a series of phenolic glucuronide 1a-e and sulfate 2a-e derivates as candidate metabolites for use as reference compounds in metabolic profiling studies and for the exploration of flavonoid bioactivity. (C) 2012 Published by Elsevier Ltd.