(Z)-((2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl) octadec-9-enoate | 1261480-33-4

• 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: (Z)-((2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl) octadec-9-enoate
• 英文别名: EGC-(Z)-oleate；[(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] (Z)-octadec-9-enoate
• CAS: 1261480-33-4
• 化学式: C₃₃H₄₆O₈
• 分子量: 570.723
• InChiKey: VZYSEEJMWRFBOG-YPZBJEAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  41
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  137
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  [(2R,3R)-5,7-bis[[tert-butyl(dimethyl)silyl]oxy]-2-[3,4,5-tris[[tert-butyl(dimethyl)silyl]oxy]phenyl]-3,4-dihydro-2H-chromen-3-yl] (Z)-octadec-9-enoate 在 氢氟酸 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (Z)-((2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl) octadec-9-enoate
  参考文献：
  名称：

  Synthesis and structure–activity relationship of 3-O-acylated (–)-epigallocatechins as 5α-reductase inhibitors

  摘要：

  A series of 3-O-acylated (-)-epigallocatechins were synthesized and their inhibition of steroid 5 alpha-reductase was studied. They were prepared from the reaction of EGCG with tert-butyldimethylsilyl chloride followed by reductive cleavage of the ester bond. The resultant (-)-epigallocatechins penta-O-tert-butyldimethylsilyl ether was esterified with different fatty acids then desilylated to provide the corresponding products. The activity of 3-O-acylated (-)-epigallocatechins increased with the increasing carbon numbers of the fatty acid moiety, reaching maximum for 16 carbon atoms (compound 4h) with an IC50 of 0.53 mu M, which was similar to 12-fold more potent than EGCG (IC50 = 6.29 mu M). Introduction of monounsaturated fatty acid provided the most potent compound 6 (IC50 = 0.48 mu M), which showed moderate anti-tumor activity in vivo. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.10.011