23-O-octanoylsilybin | 1220982-33-1

• 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: 23-O-octanoylsilybin
• 英文别名: [3-(4-hydroxy-3-methoxyphenyl)-6-[(2R,3R)-3,5,7-trihydroxy-4-oxo-2,3-dihydrochromen-2-yl]-2,3-dihydro-1,4-benzodioxin-2-yl]methyl octanoate
• CAS: 1220982-33-1
• 化学式: C₃₃H₃₆O₁₁
• 分子量: 608.642
• InChiKey: PLRIBWVTXLKBTA-VOXJNARSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  44
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  161
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  23-O-octanoylsilybin 在 Candida antarctica lipase B 、 正丁醇 作用下， 以 甲基叔丁基醚 为溶剂， 反应 29.0h， 生成 水飞蓟素A,B
  参考文献：
  名称：

  Enzymatic Kinetic Resolution of Silybin Diastereoisomers

  摘要：

  In nature, the flavonolignan silybin (1) occurs as a mixture of two diastereomers, silybin A and silybin B, which in a number of biological assays exhibit different activities. A library of hydrolases (lipases, esterases, and proteases) was tested for separating the silybin A and B diastereomers by selective transcsterification or by stereoselective alcoholysis of 23-O-acetylsilybin (2). Novozym 435 proved to be the most suitable enzyme for the preparative production of both optically pure silybins A and B by enzymatic discrimination. Gram amounts of the optically pure substances can be produced within one week, and the new method is robust and readily scalable to tens of grams.

  DOI：

  10.1021/np900758d
• 作为产物：
  描述：

  水飞蓟素A,B 、 辛酰氯 在 三氟化硼乙醚 作用下， 以 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 以0.189 g的产率得到23-O-octanoylsilybin
  参考文献：
  名称：

  Enzymatic Kinetic Resolution of Silybin Diastereoisomers

  摘要：

  In nature, the flavonolignan silybin (1) occurs as a mixture of two diastereomers, silybin A and silybin B, which in a number of biological assays exhibit different activities. A library of hydrolases (lipases, esterases, and proteases) was tested for separating the silybin A and B diastereomers by selective transcsterification or by stereoselective alcoholysis of 23-O-acetylsilybin (2). Novozym 435 proved to be the most suitable enzyme for the preparative production of both optically pure silybins A and B by enzymatic discrimination. Gram amounts of the optically pure substances can be produced within one week, and the new method is robust and readily scalable to tens of grams.

  DOI：

  10.1021/np900758d

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.
• Enzymatic Kinetic Resolution of Silybin Diastereoisomers
  作者：Daniela Monti、Radek Gažák、Petr Marhol、David Biedermann、Kateřina Purchartová、Mirko Fedrigo、Sergio Riva、Vladimír Křen

  DOI：10.1021/np900758d

  日期：2010.4.23

  In nature, the flavonolignan silybin (1) occurs as a mixture of two diastereomers, silybin A and silybin B, which in a number of biological assays exhibit different activities. A library of hydrolases (lipases, esterases, and proteases) was tested for separating the silybin A and B diastereomers by selective transcsterification or by stereoselective alcoholysis of 23-O-acetylsilybin (2). Novozym 435 proved to be the most suitable enzyme for the preparative production of both optically pure silybins A and B by enzymatic discrimination. Gram amounts of the optically pure substances can be produced within one week, and the new method is robust and readily scalable to tens of grams.