quercetin 3'-glucuronide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: quercetin 3'-glucuronide
• 英文别名: (2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-[2-hydroxy-5-(3,5,7-trihydroxy-4-oxochromen-2-yl)phenoxy]oxane-2-carboxylic acid
• 化学式: C₂₁H₁₈O₁₃
• 分子量: 478.366
• InChiKey: LBJLXDMWOKJIPQ-YSGAUUIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  224
• 氢给体数：
  8
• 氢受体数：
  13

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 palladium dihydroxide 三氟化硼乙醚 、 sodium carbonate 、 环己烯 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 quercetin 3'-glucuronide
  参考文献：
  名称：

  Convenient syntheses of metabolically important quercetin glucuronides and sulfates

  摘要：

  Synthetic approaches to the major human plasma metabolites of quercetin, quercetin 3'-sulfate and the beta-D-glucopyranosiduronic acid derivatives 3'-methylquercetin 3-glucuronide (isorhamnetin 3-glucuronide), quercetin 3-glucuronide and quercetin 3'-glucuronide are described. This is the first report of the chemical synthesis of quercetin 3'-glucuronide. All procedures start from the same precursor, 4',7-di-O-benzylquercetin, and all are more convenient than existing methods. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.102

文献信息

• Convenient syntheses of metabolically important quercetin glucuronides and sulfates
  作者：Paul W. Needs、Paul A. Kroon

  DOI：10.1016/j.tet.2006.04.102

  日期：2006.7

  Synthetic approaches to the major human plasma metabolites of quercetin, quercetin 3'-sulfate and the beta-D-glucopyranosiduronic acid derivatives 3'-methylquercetin 3-glucuronide (isorhamnetin 3-glucuronide), quercetin 3-glucuronide and quercetin 3'-glucuronide are described. This is the first report of the chemical synthesis of quercetin 3'-glucuronide. All procedures start from the same precursor, 4',7-di-O-benzylquercetin, and all are more convenient than existing methods. (c) 2006 Elsevier Ltd. All rights reserved.