5,7-二羟基-3,3,4,5-四甲氧基黄酮 | 14585-04-7

• 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: 5,7-二羟基-3,3,4,5-四甲氧基黄酮
• 英文名称: 5,7-dihydroxy-3,3',4',5'-tetramethoxyflavone
• 英文别名: myricetin 3,3',4',5'-tetramethyl ether；3',3',4',5'-tetra-O-methylmyricetin；5,7-dihydroxy-3-methoxy-2-(3,4,5-trimethoxy-phenyl)-chromen-4-one；5,7-Dihydroxy-3-methoxy-2-(3,4,5-trimethoxy-phenyl)-chromen-4-on；5,7-Dihydroxy-3,3',4',5'-tetramethoxyflavon；3,3',4',5'-Tetramethyl-myricetin；5,7-dihydroxy-3-methoxy-2-(3,4,5-trimethoxyphenyl)chromen-4-one
• CAS: 14585-04-7
• 化学式: C₁₉H₁₈O₈
• 分子量: 374.347
• InChiKey: YSXLGTWJLNLXKQ-UHFFFAOYSA-N

物化性质

• 沸点：
  594.2±50.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  8

安全信息

• 海关编码：
  2914509090

反应信息

• 作为反应物：
  描述：

  5,7-二羟基-3,3,4,5-四甲氧基黄酮 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以95.2%的产率得到杨梅素
  参考文献：
  名称：

  一种杨梅素的制备方法

  摘要：

  本发明属于药物化学合成技术领域，具体涉及一种杨梅素的制备方法。本发明所述的杨梅素的制备方法步骤为：一、以1‑1所示化合物为原料，在酸性条件下与甲氧基乙腈发生酰基化反应得到1‑3所示化合物；二、1‑3所示化合物再与3，4，5‑三甲氧基苯甲酸酐发生重排反应生成1‑5所示化合物；三、1‑5所示化合物在BBr3的二氯甲烷溶液中发生脱甲基反应生成3‑1所示的化合物，即为杨梅素。本发明所述的全合成路线从间苯三酚出发，经三步反应，以60％的总收率成功地合成了杨梅素。具有原料便宜易得、反应条件温和、合成路线短、产物收率高、操作简单、环境污染小等优点。

  公开号：

  CN109020938A
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲酸 在 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.41h， 生成 5,7-二羟基-3,3,4,5-四甲氧基黄酮
  参考文献：
  名称：

  Effects of Flavonoids on Cell Proliferation and Caspase Activation in a Human Colonic Cell Line HT29:  An SAR Study

  摘要：

  A library of 42 natural and synthetic flavonoids has been screened for their effect on cell proliferation and apoptosis in a human colonic cell line (HT-29). Examples of different classes of flavonoids have been screened, and the effects of hydroxylation, methoxylation and/or C-alkylation at various positions in the A- and B-rings have been assessed. Flavones and flavonols possess greater antiproliferative activity than chalcones and flavanones. With respect to structural modification of flavonoids, C-isoprenylation was by far the most effective, with substitution at the 8-position and longer chains, such as geranyl giving the best results. Finally, most compounds that significantly reduced cell survival also increased caspase activity, suggesting that at least part of their antiproliferative activity might be attributable to an apoptotic response.

  DOI：

  10.1021/jm040770b

文献信息

• Rao; Seshadri, Proceedings - Indian Academy of Sciences, Section A, 1947, # 25, p. 444,445
  作者：Rao、Seshadri

  DOI：——

  日期：——
• Kalff; Robinson, Journal of the Chemical Society, 1925, vol. 127, p. 182
  作者：Kalff、Robinson

  DOI：——

  日期：——
• Ahluwalia et al., Journal of the Chemical Society, 1954, p. 3988
  作者：Ahluwalia et al.

  DOI：——

  日期：——
• Srivastava, Santosh K.; Gupta, Rakesh K.; Srivastava, Savitri D., Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1981, vol. <B> 20, # 9, p. 833
  作者：Srivastava, Santosh K.、Gupta, Rakesh K.、Srivastava, Savitri D.

  DOI：——

  日期：——
• Effects of Flavonoids on Cell Proliferation and Caspase Activation in a Human Colonic Cell Line HT29:  An SAR Study
  作者：Jean-Baptiste Daskiewicz、Flore Depeint、Lionel Viornery、Christine Bayet、Geraldine Comte-Sarrazin、Gilles Comte、Jennifer M. Gee、Ian T. Johnson、Karine Ndjoko、Kurt Hostettmann、Denis Barron

  DOI：10.1021/jm040770b

  日期：2005.4.1

  A library of 42 natural and synthetic flavonoids has been screened for their effect on cell proliferation and apoptosis in a human colonic cell line (HT-29). Examples of different classes of flavonoids have been screened, and the effects of hydroxylation, methoxylation and/or C-alkylation at various positions in the A- and B-rings have been assessed. Flavones and flavonols possess greater antiproliferative activity than chalcones and flavanones. With respect to structural modification of flavonoids, C-isoprenylation was by far the most effective, with substitution at the 8-position and longer chains, such as geranyl giving the best results. Finally, most compounds that significantly reduced cell survival also increased caspase activity, suggesting that at least part of their antiproliferative activity might be attributable to an apoptotic response.