2,4-dihydroxyphenyl-O-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4-dihydroxyphenyl-O-β-D-glucopyranoside
• 英文别名: 2,4-dihydoxyphenyl-β-D-glucoside；4-O-glucopyranosylresorcinol；(2S,3R,4S,5S,6R)-2-(2,4-dihydroxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₁₂H₁₆O₈
• 分子量: 288.254
• InChiKey: RJOMVDWEROYLOZ-RMPHRYRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  140
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  苯甲酸 、 2,4-dihydroxyphenyl-O-β-D-glucopyranoside 在 吡啶 、 双(2-氧代-3-恶唑烷基)次磷酰氯 作用下， 生成 2,4-dihydroxyphenyl-(6′-O-benzoyl)-O-β-D-glucoside
  参考文献：
  名称：

  Polyphenolic Glycosides from African Proteaceae

  摘要：

  The phytochemical investigation of members of the genus Protea afforded a series of polyphenolic compounds (1-5) that were identified by 1D and 2D NMR experiments. Of these, 2-5 are new compounds. Chemical syntheses of 1-3 were performed in order to confirm the structures and to prepare additional material for biological evaluation.

  DOI：

  10.1021/np9902237
• 作为产物：
  描述：

  2,4-二苄氧基苯甲醛 在 甲醇 、 三氟甲磺酸三甲基硅酯 、 20% palladium hydroxide-activated charcoal 、 氢气 、 sodium methylate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 2,4-dihydroxyphenyl-O-β-D-glucopyranoside
  参考文献：
  名称：

  JP5893442

  摘要：

  公开号：

文献信息

• Chemical synthesis and tyrosinase-inhibitory activity of isotachioside and its related glycosides
  作者：Takashi Matsumoto、Takuya Nakajima、Takehiro Iwadate、Ken-ichi Nihei

  DOI：10.1016/j.carres.2018.06.004

  日期：2018.7

  tyrosinase inhibitory activity was evaluated. The half maximal inhibitory concentration (IC50) of 1-3 could not be determined even when the concentration was increased to 1000 μM. Contrastingly, glycosides 4-7, missing methyl and benzoyl groups, acted as tyrosinase inhibitors with IC50s of 417 μM, 852 μM, 623 μM, and 657 μM, respectively. Among these novel inhibitors, derivative 4 was the most potent

  异黄酮苷（1）及其相关的天然产物2分别从异黄杨和普罗梯亚木中分离出来，并归类为实际应用的酪氨酸酶抑制剂熊果苷（3）的类似物。作为关键步骤，通过施密特糖基化合成了天然产物和几种衍生物，如葡糖苷4，木糖苷5，纤维二糖苷6和麦芽糖苷7，并评估了它们对酪氨酸酶的抑制活性。即使将最大抑制浓度（IC50）增加到1000μM，也无法确定。相反，缺少甲基和苯甲酰基的糖苷4-7充当酪氨酸酶抑制剂，IC50分别为417μM，852μM，623μM和657μM。在这些新型抑制剂中，衍生物4最有效，
• JP5893442
  申请人：——

  公开号：——

  公开（公告）日：——
• Polyphenolic Glycosides from African Proteaceae
  作者：L. Verotta、F. Orsini、F. Pelizzoni、G. Torri、C. B. Rogers

  DOI：10.1021/np9902237

  日期：1999.11.1

  The phytochemical investigation of members of the genus Protea afforded a series of polyphenolic compounds (1-5) that were identified by 1D and 2D NMR experiments. Of these, 2-5 are new compounds. Chemical syntheses of 1-3 were performed in order to confirm the structures and to prepare additional material for biological evaluation.