genistein 7-O-(6-O-((E)-caffeoyl)-β-D-glucopyranoside) | 1401251-26-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: genistein 7-O-(6-O-((E)-caffeoyl)-β-D-glucopyranoside)
• 英文别名: [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• CAS: 1401251-26-0
• 化学式: C₃₀H₂₆O₁₃
• 分子量: 594.529
• InChiKey: BKEBCFOVVYCSFF-LKCCXEKDSA-N

物化性质

• 沸点：
  956.3±65.0 °C(Predicted)
• 密度：
  1.615±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  43
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  213
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  genistein 7-O-(6-O-((E)-caffeoyl)-β-D-glucopyranoside) 在 硫酸 、 水 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 葡萄糖 、 TRANS-咖啡酸 、 染料木素
  参考文献：
  名称：

  A new isoflavone from Blepharis ciliaris of an Egyptian origin

  摘要：

  A phytochemical study of the aerial parts of Blepharis ciliaris (L.) B.L. Burtt. led to the isolation of one new isoflavone glycoside caffeic acid ester: genistein-7-O-(6aEuro(3)-O-E-caffeoyl-beta-d-glucopyranoside) (4), along with seven known compounds: methyl veratrate (1), methyl vanillate (2), protocatechuic acid (3), naringenin-7-O-(3aEuro(3)-acetyl-6aEuro(3)-E-p-coumaroyl-beta-d-glucopyranoside) (5), naringenin-7-O-(6aEuro(3)-E-p-coumaroyl-beta-d-glucopyranoside) (6), apigenin-7-O-(6aEuro(3)-E-p-coumaroyl-beta-d-glucopyranoside) (7), and acteoside (8). Their structures were established on the basis of detailed analyses of physical, chemical, and spectral data. Compounds 1, 2, 3, 6, and 8 were isolated for the first time from this plant. The antioxidant activity of the different extracts as well as for some of the isolated compounds was evaluated.

  DOI：

  10.1007/s00044-012-0228-2

文献信息

• A new isoflavone from Blepharis ciliaris of an Egyptian origin
  作者：Mohamed A. El-Shanawany、Hanaa M. Sayed、Sabrin R. M. Ibrahim、Marwa A. A. Fayed、Mohamed M. Radwan、Samir A. Ross

  DOI：10.1007/s00044-012-0228-2

  日期：2013.5

  A phytochemical study of the aerial parts of Blepharis ciliaris (L.) B.L. Burtt. led to the isolation of one new isoflavone glycoside caffeic acid ester: genistein-7-O-(6aEuro(3)-O-E-caffeoyl-beta-d-glucopyranoside) (4), along with seven known compounds: methyl veratrate (1), methyl vanillate (2), protocatechuic acid (3), naringenin-7-O-(3aEuro(3)-acetyl-6aEuro(3)-E-p-coumaroyl-beta-d-glucopyranoside) (5), naringenin-7-O-(6aEuro(3)-E-p-coumaroyl-beta-d-glucopyranoside) (6), apigenin-7-O-(6aEuro(3)-E-p-coumaroyl-beta-d-glucopyranoside) (7), and acteoside (8). Their structures were established on the basis of detailed analyses of physical, chemical, and spectral data. Compounds 1, 2, 3, 6, and 8 were isolated for the first time from this plant. The antioxidant activity of the different extracts as well as for some of the isolated compounds was evaluated.