isoquercitrin 2'',3'',6''-triacetate | 959833-95-5

• 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: isoquercitrin 2'',3'',6''-triacetate
• CAS: 959833-95-5
• 化学式: C₂₇H₂₆O₁₅
• 分子量: 590.494
• InChiKey: MFXWMQUUZDTDKK-YPLLZZNTSA-N

物化性质

• 沸点：
  832.8±65.0 °C(Predicted)
• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.17
• 重原子数：
  42.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  228.72
• 氢给体数：
  5.0
• 氢受体数：
  15.0

反应信息

• 作为产物：
  描述：

  异槲皮苷 、 乙酸乙烯酯 在 Candida antarctica lipase 作用下， 以 丙酮 为溶剂， 生成 栎精-3-O-Β-D-吡喃葡萄糖基-6’’-乙酸盐 、 isoquercitrin 3'',6''-diacetate 、 isoquercitrin 2'',3'',6''-triacetate
  参考文献：
  名称：

  Enzymatic Acylation of Flavonoids: Effect of the Nature of the Substrate, Origin of Lipase, and Operating Conditions on Conversion Yield and Regioselectivity

  摘要：

  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.

  DOI：

  10.1021/jf071943j