2',4,6'-trihydroxy-4'-methoxydihydrochalcone 2'-O-β-D-glucopyranoside | 11075-15-3

• 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: 2',4,6'-trihydroxy-4'-methoxydihydrochalcone 2'-O-β-D-glucopyranoside
• 英文别名: 2',4-dihydroxy-4'-methoxy-6'-O-β-D-glucopyranoside dihydrochalcone；2',4-dihydroxy-4-methoxy-6'-O-β-D-glucopyranosyl-dihydrochalcone；4,2'-dihydroxy-4'-methoxy-6'-β-glucopyranosyloxydihydrochalcone；asebotin；1-(2-β-D-glucopyranosyloxy-6-hydroxy-4-methoxy-phenyl)-3-(4-hydroxy-phenyl)-propan-1-one；1-(2-β-D-Glucopyranosyloxy-6-hydroxy-4-methoxy-phenyl)-3-(4-hydroxy-phenyl)-propan-1-on；1-[2-hydroxy-4-methoxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3-(4-hydroxyphenyl)propan-1-one
• CAS: 11075-15-3
• 化学式: C₂₂H₂₆O₁₀
• 分子量: 450.442
• InChiKey: PQCIBORQLVRFMR-MIUGBVLSSA-N

物化性质

• 熔点：
  147.5 °C
• 沸点：
  779.1±60.0 °C(Predicted)
• 密度：
  1.471±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  166
• 氢给体数：
  6
• 氢受体数：
  10

安全信息

• 储存条件：
  存储条件：2-8℃，干燥，密闭

反应信息

• 作为反应物：
  描述：

  2',4,6'-trihydroxy-4'-methoxydihydrochalcone 2'-O-β-D-glucopyranoside 在 盐酸 作用下， 反应 0.5h， 生成 4'-O-甲基根皮素
  参考文献：
  名称：

  Dihydrochalcones:  Evaluation as Novel Radical Scavenging Antioxidants

  摘要：

  Dihydrochalcones are a family of bicyclic flavonoids, defined by the presence of two benzene rings joined by a saturated three carbon bridge. In the present study, we systematically examined the antioxidant activities of dihydrochalcones against the stable free radical (1,1-diphenyl-2-picrylhydrazyl) and lipid peroxidation in the erythrocyte membrane. All dihydrochalcones exhibited higher antioxidant activities than the corresponding flavanones. The H-1 NMR analysis indicated that the active dihydrochalcone has a time-averaged conformation in which the aromatic A ring is orthogonal to the carbonyl group, while the inactive dihydrochalcone such as 2'-O-methyl-phloretin has a strongly hydrogen-bonded phenolic hydroxyl group, suggestive of a coplanar conformation. A hydroxyl group at the 2'-position of the dihydrochalcone A ring, newly formed by reduction of the flavanone C ring, is an essential pharmacophore for its radical scavenging potential.

  DOI：

  10.1021/jf0341060
• 作为产物：
  描述：

  phloridizin 、 三甲基硅烷化重氮甲烷 在 二异丙胺 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 1.0h， 生成 2',4,6'-trihydroxy-4'-methoxydihydrochalcone 2'-O-β-D-glucopyranoside
  参考文献：
  名称：

  Dihydrochalcones:  Evaluation as Novel Radical Scavenging Antioxidants

  摘要：

  Dihydrochalcones are a family of bicyclic flavonoids, defined by the presence of two benzene rings joined by a saturated three carbon bridge. In the present study, we systematically examined the antioxidant activities of dihydrochalcones against the stable free radical (1,1-diphenyl-2-picrylhydrazyl) and lipid peroxidation in the erythrocyte membrane. All dihydrochalcones exhibited higher antioxidant activities than the corresponding flavanones. The H-1 NMR analysis indicated that the active dihydrochalcone has a time-averaged conformation in which the aromatic A ring is orthogonal to the carbonyl group, while the inactive dihydrochalcone such as 2'-O-methyl-phloretin has a strongly hydrogen-bonded phenolic hydroxyl group, suggestive of a coplanar conformation. A hydroxyl group at the 2'-position of the dihydrochalcone A ring, newly formed by reduction of the flavanone C ring, is an essential pharmacophore for its radical scavenging potential.

  DOI：

  10.1021/jf0341060

文献信息

• Zemplen; Mester, Chemische Berichte, 1942, vol. 75, p. 1298,1299, 1300
  作者：Zemplen、Mester

  DOI：——

  日期：——
• Dihydrochalcones:  Evaluation as Novel Radical Scavenging Antioxidants
  作者：Yoshimasa Nakamura、Shigeo Watanabe、Nobuyuki Miyake、Hiroyuki Kohno、Toshihiko Osawa

  DOI：10.1021/jf0341060

  日期：2003.5.1

  Dihydrochalcones are a family of bicyclic flavonoids, defined by the presence of two benzene rings joined by a saturated three carbon bridge. In the present study, we systematically examined the antioxidant activities of dihydrochalcones against the stable free radical (1,1-diphenyl-2-picrylhydrazyl) and lipid peroxidation in the erythrocyte membrane. All dihydrochalcones exhibited higher antioxidant activities than the corresponding flavanones. The H-1 NMR analysis indicated that the active dihydrochalcone has a time-averaged conformation in which the aromatic A ring is orthogonal to the carbonyl group, while the inactive dihydrochalcone such as 2'-O-methyl-phloretin has a strongly hydrogen-bonded phenolic hydroxyl group, suggestive of a coplanar conformation. A hydroxyl group at the 2'-position of the dihydrochalcone A ring, newly formed by reduction of the flavanone C ring, is an essential pharmacophore for its radical scavenging potential.