| 1542609-18-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• CAS: 1542609-18-6
• 化学式: C₄₁H₄₈O₂₆
• 分子量: 956.817
• InChiKey: ZZEVPEJGOAHDLP-RRYHWMOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.96
• 重原子数：
  67.0
• 可旋转键数：
  14.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  393.09
• 氢给体数：
  10.0
• 氢受体数：
  26.0

反应信息

• 作为反应物：
  描述：

  在 sodium methylate 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Synthesis of quercetin glycosides and their melanogenesis stimulatory activity in B16 melanoma cells

  摘要：

  4'-O-beta-D-Glucopyranosyl-quercetin-3-O-beta-D-glucopyranosyl-(1 -> 4)-beta-D-glucopyra-noside (3) was isolated from Helminthostachys zeylanica root extract as a melanogenesis acceleration compound and was synthesized using rutin as the starting material. Related compounds were also synthesized to understand the structure-activity relationships in melanin biosynthesis.Melanogenesis activities of the glycosides were determined by measuring intracellular melanin content in B16 melanoma cells. Among the synthesized quercetin glycosides, quercetin-3-O-beta-D-glucopyranoside (1), quercetin-3-O-beta-D-glucopyranosyl-(1 -> 4)-beta-D-glucopyranoside (2), and 3 showed more potent intracellular melanogenesis acceleration activities than theophyline used as positive control in a dose-dependent manner with no cytotoxic effect. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.062
• 作为产物：
  描述：

  在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 8.0h， 生成
  参考文献：
  名称：

  Synthesis of quercetin glycosides and their melanogenesis stimulatory activity in B16 melanoma cells

  摘要：

  4'-O-beta-D-Glucopyranosyl-quercetin-3-O-beta-D-glucopyranosyl-(1 -> 4)-beta-D-glucopyra-noside (3) was isolated from Helminthostachys zeylanica root extract as a melanogenesis acceleration compound and was synthesized using rutin as the starting material. Related compounds were also synthesized to understand the structure-activity relationships in melanin biosynthesis.Melanogenesis activities of the glycosides were determined by measuring intracellular melanin content in B16 melanoma cells. Among the synthesized quercetin glycosides, quercetin-3-O-beta-D-glucopyranoside (1), quercetin-3-O-beta-D-glucopyranosyl-(1 -> 4)-beta-D-glucopyranoside (2), and 3 showed more potent intracellular melanogenesis acceleration activities than theophyline used as positive control in a dose-dependent manner with no cytotoxic effect. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.062