3-hydroxy-5,6,7-trimethoxyflavone | 103393-09-5

• 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: 3-hydroxy-5,6,7-trimethoxyflavone
• 英文别名: 5,6,7-Trimethoxy-3-hydroxyflavone；3-hydroxy-5,6,7-trimethoxy-2-phenyl-4H-benzopyran-4-one；3-Hydroxy-5,6,7-trimethoxy-4-oxo-2-phenyl-4H-chromen；3-hydroxy-5,6,7-trimethoxy-2-phenyl-chromen-4-one；3-Hydroxy-5,6,7-trimethoxy-2-phenyl-chromen-4-on；Trimethoxy flavonol；3-hydroxy-5,6,7-trimethoxy-2-phenylchromen-4-one
• CAS: 103393-09-5
• 化学式: C₁₈H₁₆O₆
• 分子量: 328.321
• InChiKey: GJMKDCLWSVNOED-UHFFFAOYSA-N

物化性质

• 熔点：
  215-216 °C
• 沸点：
  520.5±50.0 °C(Predicted)
• 密度：
  1.333±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-hydroxy-5,6,7-trimethoxyflavone 在 lithium chloride 作用下， 以 甲醇 、 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 28.0h， 生成
  参考文献：
  名称：

  Discovery and synthesis of rocaglaol derivatives inducing apoptosis in HCT116 cells via suppression of MAPK signaling pathway

  摘要：

  DOI：

  10.1016/j.fitote.2021.104876
• 作为产物：
  描述：

  溴苯乙腈 在 sodium tetrahydroborate 、 正丁基锂 、 sodium hydride 、 二异丙胺 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-hydroxy-5,6,7-trimethoxyflavone
  参考文献：
  名称：

  通过碱介导的环化反应制备黄酮醇的新方法：3,5,6,7-四甲氧基黄酮的全合成

  摘要：

  描述了一种合成黄酮醇的新方法。关键步骤是碱介导的环化-异构化-消除反应，其导致黄酮醇的形成。使用这种策略，合成并表征了三种黄酮醇。 黄酮醇-碱介导的环化-3,5,6,7-四甲氧基黄酮-LDA

  DOI：

  10.1055/s-0031-1290207

文献信息

• Synthesis of highly functionalized flavones and chromones using cycloacylation reactions and C-3 functionalization. A total synthesis of hormothamnione
  作者：Lynda W. McGarry、Michael R. Detty

  DOI：10.1021/jo00301a027

  日期：1990.7
• Oliverio; Bargellini, Gazzetta Chimica Italiana, 1948, vol. 78, p. 386,394
  作者：Oliverio、Bargellini

  DOI：——

  日期：——
• α-Glucosidase inhibition of 6-hydroxyflavones. Part 3: Synthesis and evaluation of 2,3,4-trihydroxybenzoyl-containing flavonoid analogs and 6-aminoflavones as α-glucosidase inhibitors
  作者：Hong Gao、Jun Kawabata

  DOI：10.1016/j.bmc.2004.12.010

  日期：2005.3.1

  The SAR studies suggested that the C-ring of baicalein (1) was not necessary for the activity, and validated the importance of 2,3,4-trihydroxybenzoyl structure of 1. Thus, a series of 2,3,4-trihydroxybenzoyi-containing flavonoid analogs were investigated for the alpha-glucosidase inhibitory activity. The results indicated that 5,6,7-trihydroxy-2-phenyl-4-quinolone (2) and 5,6,7-trihydroxyflavanone (4) showed the comparable activity to 1, while 3,5,6,7-tetrahydroxyflavone (7), 5,6,7-trihydroxyisoflavone (8), and 6-hydroxygenistein (9) showed moderate alpha-glucosidase inhibitory activity. In addition, it was found that 6-amino-5,7-dihydroxyflavone (16) was a more potent and specific rat intestinal alpha-glucosidase inhibitor than 1, and showed the comparable activity to acarbose. This is the first report on mammalian intestinal alpha-glucosidase inhibitory activity of 6-aminoflavones. Kinetic studies revealed that 16 inhibited both sucrose- and maltose-hydrolyzing activities of rat intestinal alpha-glucosidase uncompetitively/ (C) 2004 Elsevier Ltd. All rights reserved.
• Row; Seshadri, Proceedings - Indian Academy of Sciences, Section A, 1946, # 23, p. 23,31
  作者：Row、Seshadri

  DOI：——

  日期：——
• MCGARRY, LYNDA W.;DETTY, MICHAEL R., J. ORG. CHEM., 55,(1990) N4, C. 4349-4356
  作者：MCGARRY, LYNDA W.、DETTY, MICHAEL R.

  DOI：——

  日期：——