quercetin 3',4'-diacetate | 959833-92-2

• 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: quercetin 3',4'-diacetate
• 英文别名: 3’,4’-diacetylquercetin；[2-Acetyloxy-4-(3,5,7-trihydroxy-4-oxochromen-2-yl)phenyl] acetate
• CAS: 959833-92-2
• 化学式: C₁₉H₁₄O₉
• 分子量: 386.315
• InChiKey: VVKYSZBHHJSZKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  140
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  槲皮素 、 乙酸酐 以 neat (no solvent) 为溶剂， 以60%的产率得到quercetin 3',4'-diacetate
  参考文献：
  名称：

  Tunable microwave-assisted method for the solvent-free and catalyst-free peracetylation of natural products

  摘要：

  背景：过乙酰化是一种简单的化学修饰方法，可用于增强亲水产品的生物利用度，并获得安全稳定的前药。 结果：提出了一种完全绿色、无溶剂、无催化剂的微波辅助方法，用于过乙酰化天然产物，如欧洲叶酸、α-藤黄素、槲皮素和芦丁。通过简单调节微波加热程序，可以对具有化学多样性的多元醇进行过乙酰化，以提高生物活性，而不会降解天然起始分子。对过程的绿色性进行了评估。 结论：该方法可能普遍适用于绿色乙酰化亲水生物分子，可能易于规模化应用于工业领域，包括制药、化妆品和食品行业。

  DOI：

  10.3762/bjoc.12.214

文献信息

• Enzymatic Acylation of Flavonoids: Effect of the Nature of the Substrate, Origin of Lipase, and Operating Conditions on Conversion Yield and Regioselectivity
  作者：Latifa Chebil、Julie Anthoni、Catherine Humeau、Christine Gerardin、Jean-Marc Engasser、Mohamed Ghoul

  DOI：10.1021/jf071943j

  日期：2007.11.1

  The conversion yield at equilibrium, the initial rate, and the regioselectivity of the enzymatic acetylation of aglycone flavonoids (quercetin, naringenin, hesperetin, and chrysin) were investigated and compared to those obtained with a glycosylated one (isoquercitrin). The effects of a wide range of operating conditions were quantified. Fourier transform infrared spectrometry (FT-IR), NMR, and high performance liquid chromatography electrospray ionization mass spectrometry (HPLC-ESI-MS) analyses showed that for glycosylated flavonoids, in the presence of Candida antarctica (CAL-B), the acetylation occurred on the 2 ''-OH, 3 ''-OH, and 6 ''-OH of the glucose part, while with Pseudomonas cepacea lipase (PSL-C) acetylation takes place on 6 ''-OH of the sugar and 4 '-OH of the B-ring. For aglycone flavonoids, the acetyiation occurred only with IPSL-C on 4 '-OH, 3 '-OH, and 7-OH-1 hydroxyls. The conversion yield and the number and the relative proportions of the synthesized products were found dependent on the nature of the enzyme, the molar ratio, and the flavonoid structure. The initial rate was affected only by the origin of the enzyme.