1,3,11a-trihydroxy-9-(3,5,7-trihydroxy-4H-1-benzopyran-4-on-2-yl)-5a-[1,3,11a-trihydroxy-5a-(3,4-dihydroxyphenyl)-5,6,11-hexahydro-5,6,11-trioxanaphthacene-12-on-9-yl]-5,6,11-hexahydro-5,6,11-trioxanaphthacene-12-one | 868827-93-4

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 黄酮木脂素
• 英文名称: 1,3,11a-trihydroxy-9-(3,5,7-trihydroxy-4H-1-benzopyran-4-on-2-yl)-5a-[1,3,11a-trihydroxy-5a-(3,4-dihydroxyphenyl)-5,6,11-hexahydro-5,6,11-trioxanaphthacene-12-on-9-yl]-5,6,11-hexahydro-5,6,11-trioxanaphthacene-12-one
• 英文别名: 1,3,11a-trihydroxy-9-(4-oxo-3,5,7-trihydroxy-4H-1-benzopyran-2-yl)-5a-[1,3,11a-trihydroxy-5a-(3,4-dihydroxyphenyl)-5,6,11-hexahydro-12-oxo-5,6,11-trioxanaphthacen-9-yl]-5,6,11-hexahydro-5,6,11-trioxanaphthacene-12-one；5a-[5a-(3,4-Dihydroxyphenyl)-1,3,11a-trihydroxy-12-oxochromeno[3,2-b][1,4]benzodioxin-9-yl]-1,3,11a-trihydroxy-9-(3,5,7-trihydroxy-4-oxochromen-2-yl)chromeno[2,3-b][1,4]benzodioxin-12-one；5a-[5a-(3,4-dihydroxyphenyl)-1,3,11a-trihydroxy-12-oxochromeno[3,2-b][1,4]benzodioxin-9-yl]-1,3,11a-trihydroxy-9-(3,5,7-trihydroxy-4-oxochromen-2-yl)chromeno[2,3-b][1,4]benzodioxin-12-one
• CAS: 868827-93-4
• 化学式: C₄₅H₂₆O₂₁
• 分子量: 902.689
• InChiKey: KDXZZVCSADCLQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  66
• 可旋转键数：
  3
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  338
• 氢给体数：
  11
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  1,3,11a-trihydroxy-9-(3,5,7-trihydroxy-4H-1-benzopyran-4-on-2-yl)-5a-[1,3,11a-trihydroxy-5a-(3,4-dihydroxyphenyl)-5,6,11-hexahydro-5,6,11-trioxanaphthacene-12-on-9-yl]-5,6,11-hexahydro-5,6,11-trioxanaphthacene-12-one 、 重氮甲烷 以 甲醇 、 乙醚 为溶剂， 生成 5'a-(3,4-dimethoxy-phenyl)-1,3,11a,1',3',11'a-hexamethoxy-9-(3,5,7-trimethoxy-4-oxo-4H-chromen-2-yl)-5'a,11'a-dihydro-[5a,9']bi[5,6,11-trioxa-naphthacenyl]-12,12'-dione
  参考文献：
  名称：

  Antioxidative Compounds from the Outer Scales of Onion

  摘要：

  Antioxidative compounds were isolated from the methanol extract of dry outer scales of onion (Allium cepa L.). Nine phenolic compounds (1-9) were finally obtained by reversed-phase high-performance liquid chromatography, and their structures were elucidated by NMR and mass spectrometry analyses. They were the six known compounds, protocatechuic acid (1), 2-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxy-3(2H)-benzofuranone (2), quercetin 4'-O-beta-D-glucopyranoside (3), quercetin (5), 4'-O-beta-D-glucopyranoside of quercetin dimer (7), and quercetin dimer (8), and three novel compounds, condensation products of quercetin with protocatechuic acid (4), adduct of quercetin with quercetin 4'-O-beta-D-glucopyranoside (6), and quercetin trimer (9). These phenolic compounds were tested for their antioxiclant properties using autoxidation of methyl linoleate in bulk phase or free radical initiated peroxidation of soybean phosphatidylcholine in liposomes. The flavonoid compounds having o-dihydroxy substituent in the B-ring were shown to be effective antioxidants against nonenzymic lipid peroxidation.

  DOI：

  10.1021/jf051264d
• 作为产物：
  描述：

  槲皮素 在 potassium hexacyanoferrate(III) 作用下， 以 丙酮 为溶剂， 反应 0.55h， 以9%的产率得到1,3,11a-trihydroxy-9-(3,5,7-trihydroxy-4H-1-benzopyran-4-on-2-yl)-5a-(3,4-dihydroxyphenyl)-5,6,11-hexahydro-5,6,11-trioxanaphthacene-12-one
  参考文献：
  名称：

  Oligomeric oxidation products of the flavonoid quercetin

  摘要：

  研究表明，槲皮素的一些主要氧化产物是起始黄酮类化合物低聚形成的化合物。研究人员开发了制备合成这些化合物的条件。利用 HPLC-MS 和 NMR 方法确定了这些化合物的结构。利用色谱法发现了天然样本（改良的薤白匐茎外叶）中的槲皮素低聚物。建议使用槲皮素低聚物作为其氧化的指示剂。

  DOI：

  10.1007/s10600-008-9092-1