5,6,7-三羟基-2-(4-羟基-3-甲氧基苯基)-4H-1-苯并吡喃-4-酮 | 23494-48-6

• 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: 5,6,7-三羟基-2-(4-羟基-3-甲氧基苯基)-4H-1-苯并吡喃-4-酮
• 英文名称: O6-Desmethyljaceosidin
• 英文别名: 5,6,7,4′-tetrahydroxy-3′-methoxyflavone；nodifloretin；5,6,7-trihydroxy-2-(4-hydroxy-3-methoxy-phenyl)-chromen-4-one；Batatifolin；5,6,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one
• CAS: 23494-48-6
• 化学式: C₁₆H₁₂O₇
• 分子量: 316.267
• InChiKey: OZVBXGBZPZBKJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

安全信息

• 海关编码：
  2914509090

反应信息

• 作为反应物：
  描述：

  5,6,7-三羟基-2-(4-羟基-3-甲氧基苯基)-4H-1-苯并吡喃-4-酮 、 乙酸酐 以33%的产率得到
  参考文献：
  名称：

  HORIE TOKUHARU, NIXON KAGAKU KAJSI, NIRRON KAGAKU KAISNI, J. CHEM. SOS. JAR., CHEM. AND I+

  摘要：

  DOI：
• 作为产物：
  描述：

  4',5,7,8-tetrahydroxy-3'-methoxyflavone 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 生成 5,6,7-三羟基-2-(4-羟基-3-甲氧基苯基)-4H-1-苯并吡喃-4-酮
  参考文献：
  名称：

  Tlc, uv and acidic treatment in the differentiation of 5,6- and 5,8-dihydroxyflavones, 3-methoxyflavones and flavonols

  摘要：

  DOI：

  10.1016/s0040-4020(01)91379-1

文献信息

• Compositions of flavonoids and flavonoid-containing extracts and the treatment of diseases
  申请人：Gong Qiang Bang

  公开号：US20050049206A1

  公开（公告）日：2005-03-03

  In this invention, we describe a group of flavonoids and flavonoid-containing extracts that have pharmaceutical properties which are useful in the medicinal therapy of fibrotic diseases for the treatment or reparation and prevention of fibrotic lesional tissues. Representative flavonoids and flavonoid-containing extracts have the active compositions of the below formula. Those compositions can be extracted and purified from the botanicals, including Scutellaria baicalensis Georgi, Scutellaria scordifolia Fisch,Oroxylum indicum(L.) Vent, Plantago major L. The compositions of the invention are novel as an anti-fibrotic drugs, as agents for treating fibrosis.

  在这项发明中，我们描述了一组黄酮类化合物和含黄酮类化合物的提取物，具有药物特性，可用于治疗纤维化疾病的药物疗法，用于治疗、修复和预防纤维化病变组织。代表性的黄酮类化合物和含黄酮类化合物的提取物具有以下公式的活性成分。这些成分可以从植物中提取和纯化，包括黄芩、紫花地丁、橙黄木、车前草等。本发明的成分作为抗纤维化药物和治疗纤维化的药剂是新颖的。
• Studies of the selective O-alkylation and dealkylation of flavonoids. 13. An improved method for synthesizing 5,6,7-trihydroxyflavones from 6-hydroxy-5,7-dimethoxyflavones
  作者：Tokunaru Horie、Hideaki Tominaga、Yasuhiko Kawamura、Toshihide Yamada

  DOI：10.1021/jo00038a023

  日期：1992.6

  The demethylation of five 6-hydroxy-5,7-dimethoxyflavones 1 and their acetates with 30% w/v anhydrous aluminum chloride in acetonitrile was studied, and the following results were found. In the demethylation of 6-hydroxy-4',5,7-trimethoxyflavone (1a), 5,6-dihydroxy-4',7-dimethoxyflavone (2a) and 5,6,7-trihydroxy-4'-methoxyflavone (3a) were produced. Although the ratio of the two products varied according to the amount of aluminum chloride used, it became constant after 12-24 h because the cleavage of the 7-methoxy group in 2a was suppressed by iminoesterification of the 6-hydroxy group. In contrast, the demethylation of the 5- and 7-methoxy groups of acetate 4a proceeded smoothly by the process shown in Scheme II. The amount of 3a increased with increasing reaction time to give 3a as the main product after 36-48 h. The same phenomena were observed in the demethylation of the other 6-hydroxyflavones 1b-1e and their acetates 4b-4e. The demethylation of the acetates is widely applicable as a general method for synthesizing 5,6,7-trihydroxyflavones because the protection of hydroxy groups also suppresses the further cleavage of the methoxy group adjacent to the acetoxy group on the B ring of compounds such as 4d and 4e.
• USE OF FLAVONES FOR TREATING PSYCHIATRIC DISORDERS WITH SENSORIMOTOR GATING DEFICITS
  申请人：CHIOU Lih-Chu

  公开号：US20120029066A1

  公开（公告）日：2012-02-02

  Novel Use of flavones having 2-phenylchromen-4-one skeleton is disclosed herein. The flavones are useful as lead compounds for manufacturing a medicament or a pharmaceutical composition for treating a patient diagnosed with a psychiatric disorder with sensorimotor gating deficits.
• [EN] COMPOSITIONS OF FLAVONOIDS AND FLAVONOID-CONTAINING EXTRACTS AND THE TREATMENT OF DISEASES<br/>[FR] COMPOSITIONS DE FLAVONOIDES ET D'EXTRAITS QUI CONTIENNENT DES FLAVONOIDES, ET TRAITEMENT DE MALADIES
  申请人：SHANGHAI COMMAN PHARMACEUTICAL

  公开号：WO2005020881A2

  公开（公告）日：2005-03-10

  In this invention we describe a group of flavonoids and flavonoid-containing extracts that have pharmaceutical properties which are useful in the medicinal therapy of fibrotic diseases for the treatment or reparation and prevention of fibrotic lesional tissues. Representative flavonoids and flavonoid-containing extracts have the active compositions of the below formula (I). Those compositions can be extracted and purified from the botanicals, including Scutellaria baicalensis Georgi, Scutellaria scordifolia Fish, Oroxylum indicum (L.) Vent, Plantago major L. The compositions of the invention are novel as an anti-fibrotic drugs, as agents for treating fibrosis.
• Tlc, uv and acidic treatment in the differentiation of 5,6- and 5,8-dihydroxyflavones, 3-methoxyflavones and flavonols
  作者：F.A.T. Barberán、F. Ferreres、F. Tomás

  DOI：10.1016/s0040-4020(01)91379-1

  日期：1985.1