5,7-bisbenzyloxy-2-(3,4-bisbenzyloxyphenyl)-3-(β-D-glucopyranosyloxy)-4H-chromen-4-one | 1332833-27-8

• 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-bisbenzyloxy-2-(3,4-bisbenzyloxyphenyl)-3-(β-D-glucopyranosyloxy)-4H-chromen-4-one
• 英文别名: 2-[3,4-bis(phenylmethoxy)phenyl]-5,7-bis(phenylmethoxy)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• CAS: 1332833-27-8
• 化学式: C₄₉H₄₄O₁₂
• 分子量: 824.881
• InChiKey: HHSPGEDNEJLEDO-WENQLMTDSA-N

物化性质

• 沸点：
  1007.6±65.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  61
• 可旋转键数：
  16
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  163
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  5,7-bisbenzyloxy-2-(3,4-bisbenzyloxyphenyl)-3-(β-D-glucopyranosyloxy)-4H-chromen-4-one 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 2.0h， 生成 异槲皮苷
  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：

  溴甲苯 在 盐酸 、 sodium methylate 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 5,7-bisbenzyloxy-2-(3,4-bisbenzyloxyphenyl)-3-(β-D-glucopyranosyloxy)-4H-chromen-4-one
  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

文献信息

• An expeditious synthesis of quercetin 3-O-β-d-glucuronide from rutin
  作者：Mohammed Kajjout、Rajae Zemmouri、Christian Rolando

  DOI：10.1016/j.tetlet.2011.06.108

  日期：2011.9

  We report the synthesis of the major human metabolite of quercetin, quercetin 3-O-β-d-glucuronide, from rutin (quercetin-3-rutinoside), which is commercially available at low cost. This straightforward synthesis is based on the key intermediate 3′,4′,5,7-tetra-O-benzyl-quercetin which is obtained in only two steps by the total benzylation of rutin followed by acid hydrolysis of the rutinoside residue

  我们报道了槲皮素的主要人类代谢产物，槲皮素3- O- β- d-葡萄糖苷酸的合成，得自芦丁（槲皮素-3-芸香糖苷），其价格低廉。这种简单的合成是基于关键中间体3'，4'，5,7-四-O-苄基-槲皮素，该步骤仅通过两步进行，即芦丁的总苄基化，然后通过芸苔苷残基的酸水解即可获得。1-溴-3,4,6-四-O-乙酰基-α- d对游离3羟基的糖基化作用-吡喃葡糖苷产生被保护的葡糖苷。TEMPO介导的脱保护的葡糖苷上伯醇的氧化使人们能够接触到苄基化的葡糖醛酸苷。通过H 2（10％Pd / C）除去保护槲皮素羟基的苄基产生槲皮素3- O- β- d-葡糖醛酸苷。