2-[2,3-dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxin-6-yl]-2,3-dihydro-3,5-dihydroxy-7-(cis,cis-9,12-octadecadienoyl)-oxy-4H-1-benzopyran-4-one | 1221681-86-2

• 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: 2-[2,3-dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxin-6-yl]-2,3-dihydro-3,5-dihydroxy-7-(cis,cis-9,12-octadecadienoyl)-oxy-4H-1-benzopyran-4-one
• 英文别名: [(2R,3R)-3,5-dihydroxy-2-[3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-4-oxo-2,3-dihydrochromen-7-yl] (9Z,12Z)-octadeca-9,12-dienoate
• CAS: 1221681-86-2
• 化学式: C₄₃H₅₂O₁₁
• 分子量: 744.879
• InChiKey: FVUZSHFNMFPQQP-FJTWCBJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  54
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  161
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  silibinin 、 亚麻酰氯 在 吡啶 作用下， 反应 1.0h， 以29%的产率得到2-[2,3-dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxin-6-yl]-2,3-dihydro-3,5-dihydroxy-7-(cis,cis-9,12-octadecadienoyl)-oxy-4H-1-benzopyran-4-one
  参考文献：
  名称：

  Antioxidant and antiviral activities of silybin fatty acid conjugates

  摘要：

  Two selective acylation methods for silybin esterification with long-chain fatty acids were developed, yielding a series of silybin 7-O- and 23-O-acyl-derivatives of varying acyl chain lengths. These compounds were tested for their antioxidant (inhibition of lipid peroxidation and DPPH-scavenging) and anti-influenza virus activities. The acyl chain length is an important prerequisite for both biological activities, as they improved with increasing length of the acyl moiety. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.11.056

文献信息

• Antioxidant and antiviral activities of silybin fatty acid conjugates
  作者：Radek Gažák、Kateřina Purchartová、Petr Marhol、Lucie Živná、Petr Sedmera、Kateřina Valentová、Nobuo Kato、Hiroyo Matsumura、Kunihiro Kaihatsu、Vladimír Křen

  DOI：10.1016/j.ejmech.2009.11.056

  日期：2010.3

  Two selective acylation methods for silybin esterification with long-chain fatty acids were developed, yielding a series of silybin 7-O- and 23-O-acyl-derivatives of varying acyl chain lengths. These compounds were tested for their antioxidant (inhibition of lipid peroxidation and DPPH-scavenging) and anti-influenza virus activities. The acyl chain length is an important prerequisite for both biological activities, as they improved with increasing length of the acyl moiety. (C) 2009 Elsevier Masson SAS. All rights reserved.