quercetin 3,7-O-β-D-diglucoside | 6892-74-6

• 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 3,7-O-β-D-diglucoside
• 英文别名: quercetin-3-O-β-D-glucopyranoside-7-O-β-D-glucopyranoside；7-O-β-D-glucopyranosyl-quercetin-3-O-β-D-glucopyranoside；quercetin 3,7-di-O-β-D-glucopyranoside；quercetin-3,7-di-O-β-D-glucopyranoside；quercetin 3,7-O-β-D-diglucopyranoside；quercetin-3,7-O-β-D-diglucopyranoside；Quercetin 3,7-diglucoside；2-(3,4-dihydroxyphenyl)-5-hydroxy-3,7-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]chromen-4-one
• CAS: 6892-74-6
• 化学式: C₂₇H₃₀O₁₇
• 分子量: 626.525
• InChiKey: BNSCASRSSGJHQH-DEFKTLOSSA-N

物化性质

• 熔点：
  181-186 °C
• 沸点：
  1049.9±65.0 °C(Predicted)
• 密度：
  1.89±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  44
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  286
• 氢给体数：
  11
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  quercetin 3,7-O-β-D-diglucoside 生成 槲皮素
  参考文献：
  名称：

  IMOMNAZAROV, B. A.;BANDYUKOVA, V. A., XIMIYA PRIROD. SOED.,(1988) N, S. 876-877

  摘要：

  DOI：
• 作为产物：
  描述：

  芦丁 在 盐酸 、 palladium 10% on activated carbon 、 氢气 、 sodium methylate 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 20.0~80.0 ℃ 、100.0 kPa 条件下， 反应 50.0h， 生成 quercetin 3,7-O-β-D-diglucoside
  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

• Kodama, Tohru; Ishida, Hidekatsu; Kokubo, Tetsuro, Agricultural and Biological Chemistry, 1990, vol. 54, # 12, p. 3283 - 3288
  作者：Kodama, Tohru、Ishida, Hidekatsu、Kokubo, Tetsuro、Yamakawa, Takashi、Noguchi, Hiroshi

  DOI：——

  日期：——
• Synthesis of quercetin glycosides and their melanogenesis stimulatory activity in B16 melanoma cells
  作者：Kosei Yamauchi、Tohru Mitsunaga、Irmanida Batubara

  DOI：10.1016/j.bmc.2013.12.062

  日期：2014.2

  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.
• IMOMNAZAROV, B. A.;BANDYUKOVA, V. A., XIMIYA PRIROD. SOED.,(1988) N, S. 876-877
  作者：IMOMNAZAROV, B. A.、BANDYUKOVA, V. A.

  DOI：——

  日期：——