5-乙酰氧基-7-羟基黄酮 | 132351-58-7

• 物质功能分类: 天然产物 - 黄酮类化合物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 5-乙酰氧基-7-羟基黄酮
• 英文名称: 5-acetoxy-7-hydroxyflavone
• 英文别名: 5-O-acetylchrysin；5-acetoxy-7-hydroxychrysin；7-hydroxy-4-oxo-2-phenyl-4H-chromen-5-yl acetate；5-acetoxy-7-hydroxy-2-phenyl-4H-chromen-4-one；(7-hydroxy-4-oxo-2-phenylchromen-5-yl) acetate
• CAS: 132351-58-7
• 化学式: C₁₇H₁₂O₅
• 分子量: 296.279
• InChiKey: ZCEVJMPLRAGWNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2915390090
• 储存条件：
  存储条件：2-8℃，干燥，密闭。

反应信息

• 作为反应物：
  描述：

  5-乙酰氧基-7-羟基黄酮 在 sodium methylate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 7-(6-溴己氧基)-5-羟基-2-苯基-4H-色烯-4-酮
  参考文献：
  名称：

  类胡萝卜素-黄酮结合物的合成、抗氧化性能及自组装研究

  摘要：

  类黄酮和类胡萝卜素具有有益的生理作用，例如高抗氧化能力、抗癌、免疫调节和抗炎特性，以及对紫外线的保护作用。实现了疏水性类胡萝卜素与亲水性黄酮类化合物（例如大豆黄酮和白杨素）的共价偶联，产生了新的两亲结构。黄豆苷元和白杨素的 7-叠氮己基醚通过五个步骤制备，并且它们的叠氮-炔[4+2]环加成与 8'-apo-β-胡萝卜素、玉米黄质和辣椒红的戊烯酸盐发生类胡萝卜素-类黄酮缀合物。对ABTS•+自由基阳离子的抗氧化能力和最终产品的自组装进行了检测。 1:1 类黄酮-类胡萝卜素杂合体通常表现出比其母体类黄酮更高的抗氧化活性，但低于相应的类胡萝卜素。然而，人们发现玉米黄质和辣椒红的二黄酮混合物在抗氧化能力方面表现出协同增强作用。玉米黄质-类黄酮缀合物的 ECD（电子圆二色性）和 UV-vis 分析表明，根据所用非质子极性溶剂的溶剂比例和类型，它们在丙酮/水和四氢呋喃/水混合物中形成不同的光学活性 J

  DOI：

  10.3390/molecules25030636
• 作为产物：
  描述：

  白杨素 以 二氯甲烷 为溶剂， 反应 2.25h， 生成 5-乙酰氧基-7-羟基黄酮
  参考文献：
  名称：

  类胡萝卜素-黄酮结合物的合成、抗氧化性能及自组装研究

  摘要：

  类黄酮和类胡萝卜素具有有益的生理作用，例如高抗氧化能力、抗癌、免疫调节和抗炎特性，以及对紫外线的保护作用。实现了疏水性类胡萝卜素与亲水性黄酮类化合物（例如大豆黄酮和白杨素）的共价偶联，产生了新的两亲结构。黄豆苷元和白杨素的 7-叠氮己基醚通过五个步骤制备，并且它们的叠氮-炔[4+2]环加成与 8'-apo-β-胡萝卜素、玉米黄质和辣椒红的戊烯酸盐发生类胡萝卜素-类黄酮缀合物。对ABTS•+自由基阳离子的抗氧化能力和最终产品的自组装进行了检测。 1:1 类黄酮-类胡萝卜素杂合体通常表现出比其母体类黄酮更高的抗氧化活性，但低于相应的类胡萝卜素。然而，人们发现玉米黄质和辣椒红的二黄酮混合物在抗氧化能力方面表现出协同增强作用。玉米黄质-类黄酮缀合物的 ECD（电子圆二色性）和 UV-vis 分析表明，根据所用非质子极性溶剂的溶剂比例和类型，它们在丙酮/水和四氢呋喃/水混合物中形成不同的光学活性 J

  DOI：

  10.3390/molecules25030636

文献信息

• Enzyme-catalyzed alcoholysis of flavone acetates in organic solvent
  作者：Mariapina Natoli、Giovanni Nicolosi、Mario Piattelli

  DOI：10.1016/s0040-4039(00)88570-6

  日期：1990.1

  Pseudomonas sp. lipase suspended in tetrahydrofuran was used to deacylate flavone acetates. Regioselectivity of the reaction has been observed.

  假单胞菌属。悬浮在四氢呋喃中的脂肪酶用于使乙酸黄酮去酰化。已经观察到反应的区域选择性。
• Synthesis and hypoglycemic effect of chrysin derivatives
  作者：Joon-Su Shin、Kyoung-Soon Kim、Myoung-Bohm Kim、Jae-Hoon Jeong、Bak-Kwang Kim

  DOI：10.1016/s0960-894x(99)00092-x

  日期：1999.3

  A series of 18 chrysin derivatives, prepared by alkylation and condensation, were fully characterized by NMR and other techniques and tested in vivo against the diabetes mellitus. Several modified compounds especially those with propyl, butyl, octyl and tolyl groups were found to have hypoglycemic effect on diabetec mice in spite of the fact that chrysin itself had inhibited insulin release by 40-60%. None of the test animals died at the maximum dose 500mg/kg and did not cause any significant change in general feature, water and food consumption, body weight and organ weight when we examined the acute oral toxicity of those compounds having significant hypoglycemic effect. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Design and discovery of flavonoid-based HIV-1 integrase inhibitors targeting both the active site and the interaction with LEDGF/p75
  作者：Bo-Wen Li、Feng-Hua Zhang、Erik Serrao、Huan Chen、Tino W. Sanchez、Liu-Meng Yang、Nouri Neamati、Yong-Tang Zheng、Hui Wang、Ya-Qiu Long

  DOI：10.1016/j.bmc.2014.04.016

  日期：2014.6

  HIV integrase (IN) is an essential enzyme for the viral replication. Currently, three IN inhibitors have been approved for treating HIV-1 infection. All three drugs selectively inhibit the strand transfer reaction by chelating a divalent metal ion in the enzyme active site. Flavonoids are a well-known class of natural products endowed with versatile biological activities. Their beta-ketoenol or catechol structures can serve as a metal chelation motif and be exploited for the design of novel IN inhibitors. Using the metal chelation as a common pharmacophore, we introduced appropriate hydrophobic moieties into the flavonol core to design natural product-based novel IN inhibitors. We developed selective and efficient syntheses to generate a series of mono 3/5/7/3'/4'-substituted flavonoid derivatives. Most of these new compounds showed excellent HIV-1 IN inhibitory activity in enzyme-based assays and protected against HIV-1 infection in cell-based assays. The 7-morpholino substituted 7c showed effective antiviral activity (EC50 = 0.826 mu g/mL) and high therapeutic index (TI > 242). More significantly, these hydroxyflavones block the IN-LEDGF/p75 interaction with low-to sub-micromolar IC50 values and represent a novel scaffold to design new generation of drugs simultaneously targeting the catalytic site as well as protein-protein interaction domains. (C) 2014 Elsevier Ltd. All rights reserved.
• Facile Synthesis of Flavonoid 7-<i>O</i>-Glycosides
  作者：Ming Li、Xiuwen Han、Biao Yu

  DOI：10.1021/jo034553e

  日期：2003.8.1

  Highly regioselective removal of the 7-O-acylgroups of the peracyated flavones, isoflavones, and flavonolsyl(PhSH, imidazole, NMP) followed by effective glycosylation with glycosyl trifluoroacetimidates (BF3.Et2O) and cautious deprotection of the acyl groups under basic conditions afforded the desired 7-O-flavonoid glycosides in satisfactory yields.