2-(3,4-bis(isobutyryloxy)phenyl)-4-oxo-4H-chromene-3,5,7-triyl tris(2-methylpropanoate) | 102607-68-1

• 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: 2-(3,4-bis(isobutyryloxy)phenyl)-4-oxo-4H-chromene-3,5,7-triyl tris(2-methylpropanoate)
• 英文别名: quercetin penta-O-isobutyrate
• CAS: 102607-68-1
• 化学式: C₃₅H₄₀O₁₂
• 分子量: 652.695
• InChiKey: YHSIRBAIHGAWTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.27
• 重原子数：
  47.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  161.71
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2-(3,4-bis(isobutyryloxy)phenyl)-4-oxo-4H-chromene-3,5,7-triyl tris(2-methylpropanoate) 在 lipase from Mucor miehei (Lipozyme(R) IM) 、 正丁醇 作用下， 以 various solvent(s) 为溶剂， 以92%的产率得到quercetin 3-O-isobutyrate
  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
• 作为产物：
  描述：

  异丁酸酐 、 quercetin 3-O-isobutyrate 生成 2-(3,4-bis(isobutyryloxy)phenyl)-4-oxo-4H-chromene-3,5,7-triyl tris(2-methylpropanoate)
  参考文献：
  名称：

  Kulanthaivel, Palaniappan; Benn, M. H., Canadian Journal of Chemistry, 1986, vol. 64, p. 514 - 519

  摘要：

  DOI：

文献信息

• Regioselective O-Derivatization of Quercetin via Ester Intermediates. An Improved Synthesis of Rhamnetin and Development of a New Mitochondriotropic Derivative
  作者：Andrea Mattarei、Lucia Biasutto、Federico Rastrelli、Spiridione Garbisa、Ester Marotta、Mario Zoratti、Cristina Paradisi

  DOI：10.3390/molecules15074722

  日期：——

  characterization of the two isomeric tetraacetyl quercetin derivatives was obtained by combined HSQC and HMBC 2D-NMR analysis. These molecules can be used as starting materials for the regioselective synthesis of other derivatives. High yield syntheses of the natural polyphenol rhamnetin (7-O-methylquercetin) and of the new mitochondriotropic compound 7-(4-triphenylphosphoniumbutyl) quercetin iodide are reported

  The regioselective synthesis of several quercetin (3,3',4',5,7-pentahydroxy flavone) tetraesters bearing a single free OH on 5-C was achieved in good yield by proper choice of reaction conditions using common esterification procedures. 通过咪唑促进的相应五酯的脱酰基作用，选择性地获得了在 7-C 上带有游离 OH 的四乙酰化槲皮素。通过结合 HSQC 和 HMBC 2D-NMR 分析，获得了两种异构四乙酰槲皮素衍生物的明确结构表征。这些分子可用作其他衍生物的区域选择性合成的起始材料。作为例子报道了天然多酚鼠李素（7-O-甲基槲皮素）和新的线粒体化合物7-（4