2-(3,4-bis(palmitoyloxy)phenyl)-4-oxo-4H-chromene-3,5,7-triyl tripalmitate

• 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(palmitoyloxy)phenyl)-4-oxo-4H-chromene-3,5,7-triyl tripalmitate
• 英文别名: [2-Hexadecanoyloxy-4-[3,5,7-tri(hexadecanoyloxy)-4-oxochromen-2-yl]phenyl] hexadecanoate
• 化学式: C₉₅H₁₆₀O₁₂
• 分子量: 1494.31
• InChiKey: BHZNNKAAZKNNPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  38.8
• 重原子数：
  107
• 可旋转键数：
  81
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 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-(3,4-bis(palmitoyloxy)phenyl)-4-oxo-4H-chromene-3,5,7-triyl tripalmitate 在 lipase from Mucor miehei (Lipozyme(R) IM) 、 正丁醇 作用下， 以 various solvent(s) 为溶剂， 以82%的产率得到2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-ylpalmitate
  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 、 棕榈酰氯 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以64.7%的产率得到2-(3,4-bis(palmitoyloxy)phenyl)-4-oxo-4H-chromene-3,5,7-triyl tripalmitate
  参考文献：
  名称：

  [EN] MEDICAL COMPOUNDS
  [FR] COMPOSÉS MÉDICAUX

  摘要：

  公开号：

  WO2019008537A9

文献信息

• [DE] ULTRAMIKROEMULSIONEN AUS SPONTAN DISPERGIERBAREN KONZENTRATEN MIT ANTITUMORAL, ANTIVIRAL, VIRUZID UND ANTIPARASITÄR WIRKSAMEN ESTERN VON BIOFLAVONOID-VERBINDUNGEN<br/>[EN] ULTRAMICROEMULSIONS FROM SPONTANEOUSLY DISPERSIBLE CONCENTRATES WITH ANTITUMOR, ANTIVIRAL, VIRUCIDE AND ANTIPARASITICALLY ACTIVE ESTERS OF BIOFLAVONOID COMPOUNDS<br/>[FR] ULTRAMICROEMULSIONS COMPOSEES DE CONCENTRES A DISPERSION SPONTANEE RENFERMANT DES ESTERS DE COMPOSES DE BIOFLAVONOIDE A ACTION ANTITUMORALE, ANTIVIRALE, VIRUCIDE ET ANTIPARASITAIRE
  申请人：MARIGEN S.A.

  公开号：WO1998011889A1

  公开（公告）日：1998-03-26

  (DE) Spontan dispergierbare Konzentrate mit antitumoral, antiviral, viruzid und antiparasitär einsetzbaren Estern von Bioflavonoid-Verbindungen, wässerige Ultramikroemulsionen aus solchen Konzentraten, neue Ester von ausgewählten Bioflavonoid-Verbindungen, Verfahren zu ihrer Herstellund und Aufbereitung, sowie ihre Verwendung als Mittel zur Herstellung von Heilmitteln mit Wirksamkeit gegen virale und parasitäre Erkrankungen, gegen Tumore, Ekzeme und Psoriasis, zur anhaltenden Tumor-Prophylaxe und zur verstärkten Aufnahme von exogenen Aktivatoren, metabolischen Modulatoren und Regulatoren werden beschrieben.(EN) This invention concerns spontaneously dispersible concentrates of esters with antitumor, antiviral, virucidal and antiparasitic effect which are made from bioflavonoid compounds, aqueous ultramicroemulsions out of such concentrates, new esters of selected bioflavonoid compounds, processes for producing and preparing them, and their use as agents for producing medicaments effective against viral and parasitic illnesses, against tumors, eczema and psoriasis, for ongoing tumor prophylaxis and for enhanced absorption of exogenic activators, metabolic modulators and regulators.(FR) L'invention concerne des concentrés à dispersion spontanée renfermant des esters de composés de bioflavonoïde à action antitumorale, antivirale, virucide et antiparasitaire. L'invention concerne également des ultramicroémulsions aqueuses de ces concentrés, de nouveaux esters de composés de bioflavonoïde sélectionnés, un procédé de production et de préparation correspondant ainsi que leur utilisation comme agent pour la production de médicaments agissant contre les maladies virales et parasitaires, les tumeurs, l'eczéma et le psoriasis, pour une prophylaxie durable contre les tumeurs et pour une absorption accrue d'activateurs exogènes, de modulateurs et régulateurs métaboliques.

  本发明涉及从生物花青素化合物制备的自溶性混合物，这些混合物中含有抗肿瘤、抗病毒、抗病毒性、抗寄生虫等作用的 esters。 invention 还涉及使用这类混合物制备的水超微微溶胶，以及从选择性生物花青素化合物制备的新 esters，生产及制备上述物质的方法，以及上述物质作为作用于抗病毒、抗寄生虫、抗肿瘤、抗干燥症及白癜疯等疾病的药物，同时也能用于增强外源激活因子、代谢调节剂及其调节剂的吸收的药物用途。
• ULTRAMIKROEMULSIONEN AUS SPONTAN DISPERGIERBAREN KONZENTRATEN MIT ANTITUMORAL, ANTIVIRAL, VIRUZID UND ANTIPARASITÄR WIRKSAMEN ESTERN VON BIOFLAVONOID-VERBINDUNGEN
  申请人：MARIGEN S.A.

  公开号：EP0862427A1

  公开（公告）日：1998-09-09
• [EN] MEDICAL COMPOUNDS<br/>[FR] COMPOSÉS MÉDICAUX
  申请人：VERA SALUS RICERCA S R L

  公开号：WO2019008537A9

  公开（公告）日：2020-02-20
• Antimicrobial and Anti-Lipase Activity of Quercetin and its C2-C16 3-O-Acyl-Esters
  作者：Maria Teresa Gatto、Serena Falcocchio、Eleonora Grippa、Gabriela Mazzanti、Lucia Battinelli、Giovanni Nicolosi、Daniela Lambusta、Luciano Saso

  DOI：10.1016/s0968-0896(01)00275-9

  日期：2002.2

  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.