5-hydroxy-7,8-dimethoxy-2-(4-methoxyphenyl)-4-benzopyrone | 57096-03-4

• 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: 5-hydroxy-7,8-dimethoxy-2-(4-methoxyphenyl)-4-benzopyrone
• 英文别名: 5-hydroxy-4’,7,8-trimethoxyflavone；5-hydroxy-7,8,4′-trimethoxyflavone；isoscutellarein 7,8,4'-trimethyl ether；5-hydroxy-4',7,8-trimethoxyflavone；5-hydroxy-7,8,4'-trimethoxyflavone；5-hydroxy-4,7,8-trimethoxyflavone；5-hydroxy-7,8-dimethoxy-2-(4-methoxyphenyl)chromen-4-one
• CAS: 57096-03-4
• 化学式: C₁₈H₁₆O₆
• 分子量: 328.321
• InChiKey: RRZRJBICWWNHRB-UHFFFAOYSA-N

物化性质

• 物理描述：
  Solid
• 熔点：
  220-221°C

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 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

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	galangustin	65501-87-3	C17H14O6	314.295
  4',5,7,8-四甲氧基黄酮	6-demethoxytangeretin	6601-66-7	C19H18O6	342.348
  ——	5,8-dihydroxy-7-methoxy-2-(4-methoxyphenyl)-4-benzopyrone	89456-41-7	C17H14O6	314.295
  5-羟基-4',7-二甲氧基黄酮	5-hydroxy-7,4'-dimethoxyflavone	5128-44-9	C17H14O5	298.295

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  4',5,7,8-四甲氧基黄酮	6-demethoxytangeretin	6601-66-7	C19H18O6	342.348

反应信息

• 作为反应物：
  描述：

  5-hydroxy-7,8-dimethoxy-2-(4-methoxyphenyl)-4-benzopyrone 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 5.0h， 生成 4',5,7,8-四甲氧基黄酮
  参考文献：
  名称：

  Studies on the constituents of useful plants. V. Multisubstituted flavones in the fruit peel of Citrus reticulata and their examination by gas-liquid chromatography.

  摘要：

  在对柑橘（芸香科）果皮氯仿提取物中的成分进行深入研究的基础上，从柑橘果皮中分离出 13 种黄酮类化合物，其中包括两种新的黄酮类化合物。通过光谱数据分析以及结构转换或全合成，确认了这些黄酮的结构。此外，还分离出了β-谷甾醇、柠檬甙、橙皮甙、阿魏酸和 5, 5'-oxydimethylene-bis(2-furaldehyde) 等黄酮以外的成分。通过气-液色谱法对所获得的多取代黄酮类化合物进行了检测，这些化合物可能为柑橘类化学分类学研究提供了一个很好的标记。

  DOI：

  10.1248/cpb.28.717
• 作为产物：
  描述：

  5-羟基-4',7-二甲氧基黄酮 在 二甲基二环氧乙烷 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 5.0h， 生成 5-hydroxy-7,8-dimethoxy-2-(4-methoxyphenyl)-4-benzopyrone
  参考文献：
  名称：

  Regioselective hydroxylation of 2-hydroxychalcones by dimethyldioxirane towards polymethoxylated flavonoids

  摘要：

  The flavone nucleus is part of a large number of natural products and medicinal compounds. In this presentation the novel regioselective hydroxylation of hydroxyarenes with DMD is described. The results showed further that flavonoids with 5-hydroxy group were selectively oxyfunctionalized at the para-position C8 carbon atom by DMD. Finally, according to this methodology, the naturally occurring isosinensetin, tangeretin, sinensetin, nobiletin, natsudaidain, gardenin B, 3,3',4',5,6,7,8-heptamethoxyflavone, quercetin and its derivatives were synthesized. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.01.023

文献信息

• Savona, Giuseppe; Piozzi, Franco; Rodriguez, Benjamin, Heterocycles, 1982, vol. 19, # 9, p. 1581 - 1584
  作者：Savona, Giuseppe、Piozzi, Franco、Rodriguez, Benjamin、Servettaz, Orietta

  DOI：——

  日期：——
• Chinese traditional medicines for psoriasis
  申请人：——

  公开号：US20030152588A1

  公开（公告）日：2003-08-14

  The invention relates to disclose some Chinese formula for psoriasis. Whether treatment for psoriasis is targeted at both the hyperproliferative and inflammatory aspect of the topical therapy. Specially, the administration dosage is soft gel, cream, tincture and aerosol etc. topical dosages.
• Regioselective hydroxylation of 2-hydroxychalcones by dimethyldioxirane towards polymethoxylated flavonoids
  作者：Han-Wei Chu、Huan-Ting Wu、Yean-Jang Lee

  DOI：10.1016/j.tet.2004.01.023

  日期：2004.3

  The flavone nucleus is part of a large number of natural products and medicinal compounds. In this presentation the novel regioselective hydroxylation of hydroxyarenes with DMD is described. The results showed further that flavonoids with 5-hydroxy group were selectively oxyfunctionalized at the para-position C8 carbon atom by DMD. Finally, according to this methodology, the naturally occurring isosinensetin, tangeretin, sinensetin, nobiletin, natsudaidain, gardenin B, 3,3',4',5,6,7,8-heptamethoxyflavone, quercetin and its derivatives were synthesized. (C) 2004 Elsevier Ltd. All rights reserved.
• Studies on the constituents of useful plants. V. Multisubstituted flavones in the fruit peel of Citrus reticulata and their examination by gas-liquid chromatography.
  作者：MUNEKAZU IINUMA、SHIN MATSUURA、KAZUAKI KUROGOCHI、TSUGIO TANAKA

  DOI：10.1248/cpb.28.717

  日期：——

  Thirteen kinds of flavones, including two new flavones, were isolated from the fruit peel of Citrus reticulata BLANCO (Rutaceae) on the basis of thorough examination of the components in the chloroform extract of the peel. The structures of these flavones were confirmed by analysis of the spectral data and by structural conversion or total synthesis. β-Sitosterol, limonin, hesperidin, ferulic acid, and 5, 5'-oxydimethylene-bis(2-furaldehyde) were also isolated as components other than flavones. The multisubstituted flavones obtained were examined by gas-liquid chromatography, and may provide a good marker for chemotaxonomical studies of Citrus species.

  在对柑橘（芸香科）果皮氯仿提取物中的成分进行深入研究的基础上，从柑橘果皮中分离出 13 种黄酮类化合物，其中包括两种新的黄酮类化合物。通过光谱数据分析以及结构转换或全合成，确认了这些黄酮的结构。此外，还分离出了β-谷甾醇、柠檬甙、橙皮甙、阿魏酸和 5, 5'-oxydimethylene-bis(2-furaldehyde) 等黄酮以外的成分。通过气-液色谱法对所获得的多取代黄酮类化合物进行了检测，这些化合物可能为柑橘类化学分类学研究提供了一个很好的标记。