木犀草素-5-甲醚 | 58115-29-0

• 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: 木犀草素-5-甲醚
• 英文名称: 2-(3,4-dihydroxyphenyl)-7-hydroxy-5-methoxy-4H-chromen-4-one
• 英文别名: 3',4',7-trihydroxy-5-methoxyflavone；7,3',4'-trihydroxy-5-methoxyflavone；luteolin 5-O-methyl ether；luteolin 5-methyl ether；luteolin-5-methyl ether；Luteolin-5-methylether；2-(3,4-dihydroxyphenyl)-7-hydroxy-5-methoxychromen-4-one
• CAS: 58115-29-0
• 化学式: C₁₆H₁₂O₆
• 分子量: 300.268
• InChiKey: OZPMKAZMPNDLKX-UHFFFAOYSA-N

物化性质

• 熔点：
  281-282 °C
• 沸点：
  631.9±55.0 °C(Predicted)
• 密度：
  1.512±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 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：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 储存条件：
  2-8℃

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
  5,7-二甲氧基木犀草素	5,7-dimethoxyluteolin	90363-40-9	C17H14O6	314.295
  木犀草素	2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on	491-70-3	C15H10O6	286.241
  ——	7-(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-5-hydroxy-4Hchromen-4-one	1201807-92-2	C36H28O6	556.615

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  5,7-二甲氧基木犀草素	5,7-dimethoxyluteolin	90363-40-9	C17H14O6	314.295
  木犀草素-5,4'-二甲醚	Luteolin-5,4'-dimethylether	72629-61-9	C17H14O6	314.295
  木犀草素-5,3'-二甲醚	7,4′-dihydroxy-5,3′-dimethoxyflavone	62346-14-9	C17H14O6	314.295
  羟基芫花素	7-methylluteoline	20243-59-8	C16H12O6	300.268
  香叶木素	diosmetin	520-34-3	C16H12O6	300.268
  木犀草素	2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on	491-70-3	C15H10O6	286.241

反应信息

• 作为反应物：
  描述：

  木犀草素-5-甲醚 反应 0.03h， 以8.1%的产率得到羟基芫花素
  参考文献：
  名称：

  Geiger, Hans; Casteele, Karel Vande; Sumere, Christiaan F. Van, Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1984, vol. 39, # 3, p. 393 - 396

  摘要：

  DOI：
• 作为产物：
  描述：

  7-(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-5-methoxy-4H-chromen-4-one 在 20% palladium hydroxide on carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 木犀草素-5-甲醚
  参考文献：
  名称：

  Discovery and synthesis of novel luteolin derivatives as DAT agonists

  摘要：

  Luteolin, 5,7-dihydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-one, has been proposed and proved to be a novel dopamine transporter (DAT) activator. In order to develop this potential of luteolin, a series of novel luteolin derivatives were designed, synthesized, and evaluated for their DAT agonistic activities, utilizing constructed Chinese hamster ovary (CHO) cell lines stably expressing rat DAT. Biological screening results demonstrated that luteolin derivatives 1d, 1e, and 4c carry great DAT agonistic potency (EC(50) = 0.046, 0.869, and 1.375 mu M, respectively) compared with luteolin 8 (EC(50) = 1.45 +/- 0.29 mu M). Luteolin derivative 1d, notably, exhibited a 32-fold-higher DAT agonistic potency than luteolin. These luteolin derivatives represent a novel DAT agonist class, from which lead compounds useful for exploration of additional novel DAT agonists could be drawn. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.049

文献信息

• [EN] PROCESS FOR PREPARATION OF LUTEOLIN<br/>[FR] PROCÉDÉ DE PRÉPARATION DE LUTÉOLINE
  申请人：LAURUS LABS PRIVATE LTD

  公开号：WO2013111148A1

  公开（公告）日：2013-08-01

  The present invention provides a process for preparation of Luteolin by deprotection of the corresponding ethers using Lewis acid mediated Ionic complexes, and to compositions containing the same.

  本发明提供了一种通过使用Lewis酸介导的离子复合物去保护相应醚的方法，制备黄酮素的方法，并提供含有该物质的组合物。
• Computer-aided identification, synthesis, and biological evaluation of DNA polymerase η inhibitors for the treatment of cancer
  作者：Federico Munafò、Michela Nigro、Nicoletta Brindani、Jacopo Manigrasso、Inacrist Geronimo、Giuliana Ottonello、Andrea Armirotti、Marco De Vivo

  DOI：10.1016/j.ejmech.2022.115044

  日期：2023.2
• [EN] THREE-DIMENSIONAL MOLECULAR IMAGING BY INFRARED LASER ABLATION ELECTROSPRAY IONIZATION MASS SPECTROMETRY<br/>[FR] IMAGERIE MOLÉCULAIRE TRIDIMENSIONNELLE PAR SPECTROMÉTRIE DE MASSE À IONISATION PAR ÉLECTRONÉBULISATION À ABLATION INFRAROUGE PAR LASER
  申请人：UNIV GEORGE WASHINGTON

  公开号：WO2010068491A2

  公开（公告）日：2010-06-17

  The field of the invention is atmospheric pressure mass spectrometry (MS), and more specifically a process and apparatus which combine infrared laser ablation with electrospray ionization (ESI).
• Geiger, Hans; Casteele, Karel Vande; Sumere, Christiaan F. Van, Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1984, vol. 39, # 3, p. 393 - 396
  作者：Geiger, Hans、Casteele, Karel Vande、Sumere, Christiaan F. Van

  DOI：——

  日期：——
• Discovery and synthesis of novel luteolin derivatives as DAT agonists
  作者：Jiange Zhang、Xianbo Liu、Xinsheng Lei、Lei Wang、Lihe Guo、Gang Zhao、Guoqiang Lin

  DOI：10.1016/j.bmc.2010.09.049

  日期：2010.11.15

  Luteolin, 5,7-dihydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-one, has been proposed and proved to be a novel dopamine transporter (DAT) activator. In order to develop this potential of luteolin, a series of novel luteolin derivatives were designed, synthesized, and evaluated for their DAT agonistic activities, utilizing constructed Chinese hamster ovary (CHO) cell lines stably expressing rat DAT. Biological screening results demonstrated that luteolin derivatives 1d, 1e, and 4c carry great DAT agonistic potency (EC(50) = 0.046, 0.869, and 1.375 mu M, respectively) compared with luteolin 8 (EC(50) = 1.45 +/- 0.29 mu M). Luteolin derivative 1d, notably, exhibited a 32-fold-higher DAT agonistic potency than luteolin. These luteolin derivatives represent a novel DAT agonist class, from which lead compounds useful for exploration of additional novel DAT agonists could be drawn. (C) 2010 Elsevier Ltd. All rights reserved.