5,7-dihydroxy-3-[β-D-glucopyranosyl-(1->2)-β-D-glucopyranosyl-(1->2)-β-D-glucopyranosyl]-2-(3,4-dihydroxyphenyl)-4H-1-benzopyran-4-one | 38681-85-5

• 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: 5,7-dihydroxy-3-[β-D-glucopyranosyl-(1->2)-β-D-glucopyranosyl-(1->2)-β-D-glucopyranosyl]-2-(3,4-dihydroxyphenyl)-4H-1-benzopyran-4-one
• 英文别名: quercetin 3-<β-D-glucopyranosyl(1->2)-β-D-glucopyranosyl(1->2)-β-D-glucopyranoside>；quercetin 3-O-β-D-glucopyranosyl-(1->2)-β-D-glucopyranosyl-(1->2)-β-D-glucopyranoside；quercetin β-D-glucopyranosyl (1->2)-β-D-glucopyranosyl (1->2)-β-D-glucopyranoside；quercetin 3-O-sophorotrioside；quercetin-3-O-sophorotrioside；quercetin3-sophorotriose；Quercetin 3-sophorotrioside；3-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
• CAS: 38681-85-5
• 化学式: C₃₃H₄₀O₂₂
• 分子量: 788.667
• InChiKey: IQBMWEYFKNVACH-MEBVLIOMSA-N

物化性质

• 沸点：
  1182.0±65.0 °C(Predicted)
• 密度：
  1.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  55
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  365
• 氢给体数：
  14
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  5,7-dihydroxy-3-[β-D-glucopyranosyl-(1->2)-β-D-glucopyranosyl-(1->2)-β-D-glucopyranosyl]-2-(3,4-dihydroxyphenyl)-4H-1-benzopyran-4-one 在 盐酸 作用下， 以 盐酸 为溶剂， 反应 1.0h， 生成 D-葡萄糖 、 槲皮素
  参考文献：
  名称：

  豌豆芽中酰化黄酮醇槐三苷

  摘要：

  从豌豆 (cv Solara) 芽中分离并鉴定出七种黄酮醇。槲皮素的3-葡萄糖苷和3-槐树三苷[β-D-吡喃葡萄糖基(1-->2)-β-D-吡喃葡萄糖基(1-->2)-β-D-吡喃葡萄糖苷]、槲皮素的3-槐三苷山奈酚，以及槲皮素3-槐三苷与末端糖6位羟基上的对香豆酸、咖啡酸、阿魏酸和芥子酸的酰化衍生物。咖啡酸酯和芥子酸酯是两种新的天然化合物。这是第一份通过 1H NMR 研究（包括 COSY、NOESY 和 TOCSY 实验）完全确定了槲皮素的对香豆基和阿魏基槐三苷的结构的报告，这些化合物以前是从豌豆叶中报道的。

  DOI：

  10.1016/0031-9422(95)00137-v
• 作为产物：
  描述：

  5,7-bis(acetyloxy)-3-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-acetyl-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-acetyl-β-D-glucopyranosyl]-2-[3,4-bis(acetyloxy)phenyl]-5-hydroxy-4H-1-benzopyran-4-one 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 以95%的产率得到5,7-dihydroxy-3-[β-D-glucopyranosyl-(1->2)-β-D-glucopyranosyl-(1->2)-β-D-glucopyranosyl]-2-(3,4-dihydroxyphenyl)-4H-1-benzopyran-4-one
  参考文献：
  名称：

  Total Synthesis of Quercetin 3-Sophorotrioside

  摘要：

  5,7-Dihydroxy-3-[beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl]-2-(3,4-dihydroxy- phenyl)-4H-1-benzopyran-4-one (quercetin 3-sophorotrioside), a flavonol triglycoside, isolated from Pisum sativurn shoots and showing protective effects on liver injury induced by chemicals, was synthesized for the first time. The target compound was successfully synthesized in eight linear steps and in 39% overall yield through a combination of phasetransfer-catalyzed (PTC) quercetin C-3 glycosylation and silver triflate (AgOTf) promoted carbohydrate chain elongation using both sugar bromide and trichloroacetimidate donors.

  DOI：

  10.1021/jo035722y

文献信息

• Acylated flavonol sophorotriosides from pea shoots
  作者：Federico Ferreres、Elvira Esteban、Ramón Carpena-Ruiz、María A. Jiménez、Francisco A. Tomás-Barberán

  DOI：10.1016/0031-9422(95)00137-v

  日期：1995.8

  Seven flavonols were isolated and identified from Pisum sativum (cv Solara) shoots. The 3-glucoside, and 3-sophorotrioside [beta-D-glucopyranosyl(1-->2)-beta-D- glucopyranosyl(1-->2)-beta-D-glucopyranoside] of quercetin, the 3-sophorotrioside of kaempferol, and the acylated derivatives of quercetin 3-sophorotrioside with p-coumaric, caffeic, ferulic and sinapic acids on the hydroxyl at the 6-position

  从豌豆 (cv Solara) 芽中分离并鉴定出七种黄酮醇。槲皮素的3-葡萄糖苷和3-槐树三苷[β-D-吡喃葡萄糖基(1-->2)-β-D-吡喃葡萄糖基(1-->2)-β-D-吡喃葡萄糖苷]、槲皮素的3-槐三苷山奈酚，以及槲皮素3-槐三苷与末端糖6位羟基上的对香豆酸、咖啡酸、阿魏酸和芥子酸的酰化衍生物。咖啡酸酯和芥子酸酯是两种新的天然化合物。这是第一份通过 1H NMR 研究（包括 COSY、NOESY 和 TOCSY 实验）完全确定了槲皮素的对香豆基和阿魏基槐三苷的结构的报告，这些化合物以前是从豌豆叶中报道的。
• Total Synthesis of Quercetin 3-Sophorotrioside
  作者：Yuguo Du、Guohua Wei、Robert J. Linhardt

  DOI：10.1021/jo035722y

  日期：2004.3.1

  5,7-Dihydroxy-3-[beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl]-2-(3,4-dihydroxy- phenyl)-4H-1-benzopyran-4-one (quercetin 3-sophorotrioside), a flavonol triglycoside, isolated from Pisum sativurn shoots and showing protective effects on liver injury induced by chemicals, was synthesized for the first time. The target compound was successfully synthesized in eight linear steps and in 39% overall yield through a combination of phasetransfer-catalyzed (PTC) quercetin C-3 glycosylation and silver triflate (AgOTf) promoted carbohydrate chain elongation using both sugar bromide and trichloroacetimidate donors.