[2-butanoyloxy-4-[3,5,7-tri(butanoyloxy)-4-oxochromen-2-yl]phenyl] butanoate | 82546-97-2

• 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: [2-butanoyloxy-4-[3,5,7-tri(butanoyloxy)-4-oxochromen-2-yl]phenyl] butanoate
• CAS: 82546-97-2
• 化学式: C₃₅H₄₀O₁₂
• 分子量: 652.695
• InChiKey: LXNHITMYMNDEMD-UHFFFAOYSA-N

物化性质

• 沸点：
  743.3±60.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  47
• 可旋转键数：
  21
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  158
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  [2-butanoyloxy-4-[3,5,7-tri(butanoyloxy)-4-oxochromen-2-yl]phenyl] butanoate 在 lipase from Mucor miehei (Lipozyme(R) IM) 、 正丁醇 作用下， 以 various solvent(s) 为溶剂， 以90%的产率得到quercetin-3-O-butyrate
  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：

  槲皮素 、 丁酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以52%的产率得到[2-butanoyloxy-4-[3,5,7-tri(butanoyloxy)-4-oxochromen-2-yl]phenyl] butanoate
  参考文献：
  名称：

  [EN] ACYLATED ACTIVE AGENTS AND METHODS OF THEIR USE FOR THE TREATMENT OF AUTOIMMUNE DISORDERS
  [FR] AGENTS ACTIFS ACYLÉS ET LEURS PROCÉDÉS D'UTILISATION POUR LE TRAITEMENT DE TROUBLES AUTO-IMMUNS

  摘要：

  公开号：

  WO2019236772A8

文献信息

• Peracetylation of polyphenols under rapid and mild reaction conditions
  作者：Douglas Chaves de Alcântara Pinto、Paulo Pitasse-Santos、Gabriela Alves de Souza、Rosane Nora Castro、Marco Edilson Freire de Lima

  DOI：10.1080/14786419.2022.2031186

  日期：——

  polyphenols under mild reaction conditions by using acetic anhydride, catalytic amount 4-dimethylaminopyridine (DMAP) and dimethylformamide (DMF) as solvent. Reaction conditions were adjusted for optimal formation of peracetylated polyphenols while minimizing the formation of byproducts. Butyric anhydride was employed as an alternative acylating agent and showed similar results. Reaction yields varied

  摘要 结构修饰是研究天然多酚特性的重要工具。关于乙酰酯的制备，通过分子内氢键稳定的羟基的存在可能会对这些化合物的全乙酰化造成障碍。在本文中，我们提出了一种简单的方案，使用乙酸酐、催化量的 4-二甲基氨基吡啶 (DMAP) 和二甲基甲酰胺 (DMF) 作为溶剂，在温和的反应条件下乙酰化选定的多酚。调整反应条件以获得全乙酰化多酚的最佳形成，同时最大限度地减少副产物的形成。丁酸酐被用作替代酰化剂并显示出类似的结果。反应产率从 78% 到 97% 不等，并且根据 LCMS(ESI+) 测定，获得了高纯度的产物，1 H NMR 和13 C NMR。
• Active agents and methods of their use for the treatment of metabolic disorders and nonalcoholic fatty liver disease
  申请人：Flagship Pioneering Innovations V, Inc.

  公开号：US10953027B2

  公开（公告）日：2021-03-23

  Disclosed herein are active agents, compositions containing them, unit dosage forms containing them, and methods of their use, e.g., for treating a metabolic disorder or nonalcoholic fatty liver disease or for modulating a metabolic marker or nonalcoholic fatty liver disease marker.

  本文公开了活性剂、含有活性剂的组合物、含有活性剂的单位剂型以及活性剂的使用方法，例如用于治疗代谢紊乱或非酒精性脂肪肝或调节代谢标志物或非酒精性脂肪肝标志物。
• Acylated active agents and methods of their use for the treatment of autoimmune disorders
  申请人：Flagship Pioneering Innovations V, Inc.

  公开号：US11058698B2

  公开（公告）日：2021-07-13

  Disclosed herein are acylated active agents and methods of their use, e.g., for modulating an autoimmunity marker or for treating an autoimmune disorder.

  本文公开了酰化活性剂及其使用方法，例如用于调节自身免疫标记物或治疗自身免疫性疾病的方法。
• Pentasubstituted quercetin analogs as selective inhibitors of particulate 3',5'-cyclic-AMP phosphodiesterase from rat brain
  作者：Madeleine Picq、Annie F. Prigent、Georges Nemoz、Annie C. Andre、Henri Pacheco

  DOI：10.1021/jm00352a019

  日期：1982.10

  Some penta-O-substituted analogues of quercetin were synthesized and tested for the inhibition of cytosolic and particulate rat brain cyclic AMP and cyclic GMP phosphodiesterase activities. Ten of these compounds are potent and highly selective inhibitors of cAMP hydrolysis with respect to cGMP hydrolysis. They inhibit more potently the particulate enzyme than the cytosolic preparation. The highest selectivity was observed with penta-O-ethylquercetin and analogue 6d, which proved to be more selective and more potent inhibitors than the reference compound Ro 20-1724. Some structure-activity relationships are discussed.
• WO2019236775A5
  申请人：——

  公开号：WO2019236775A5

  公开（公告）日：2022-06-13