Tetradecanoic acid 2-(3,4-dihydroxy-phenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl ester

• 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: Tetradecanoic acid 2-(3,4-dihydroxy-phenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl ester
• 英文别名: [2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl] tetradecanoate
• 化学式: C₂₉H₃₆O₈
• 分子量: 512.6
• InChiKey: WCJVBRYIJGFCHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  37
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  Tetradecanoic acid 2-(3,4-bis-tetradecanoyloxy-phenyl)-4-oxo-3,7-bis-tetradecanoyloxy-4H-chromen-5-yl ester 在 lipase from Mucor miehei (Lipozyme(R) IM) 、 正丁醇 作用下， 以 various solvent(s) 为溶剂， 以78%的产率得到Tetradecanoic acid 2-(3,4-dihydroxy-phenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl ester
  参考文献：
  名称：

  Antimicrobial and Anti-Lipase Activity of Quercetin and its C2-C16 3-O-Acyl-Esters

  摘要：

  Neither quercetin (Q). nor 3-Ow-acylquercetines, up to 100 mug/mL, had any significant activity on selected gram-positive strains (Staphylococcus aureus, Bacillus subtilis, Listeria ivanovi, Listeria monocytogenes, Listeria serligeri), gram-negative strains (Escherichia coli, Shigella flexneri, Shigella sonnei, Salmonella enteritidis, Salmonella tiphymurium) and yeasts (Candida albicans and Candida glabrata). In addition, we confirmed the known anti-HIV activity of Q (80% inhibition at 40 muM), which might depend on the free hydroxyl in the C-3 position, as suggested by the lack of activity of the 3-O-acylquercetines. Finally, we described an interesting inhibitory activity on Candida rugosa lipase by Q (IC16 = 10(-4) M) and its esters (3-O-acylquercetines) which, in vivo, could play an important role against lipase producing microorganisms. In particular, 3-O-acyl-quercetines, being more active (IC16 = 10(-4)-10(-6) M) and more lipophilic, could be more effective than Q when applied to the skin or mucosae, and deserve to be studied further. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00275-9