5,7,8-三甲氧基香豆素 | 60796-65-8

• 物质功能分类: 天然产物 - 香豆素
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: 5,7,8-三甲氧基香豆素
• 英文名称: 5,7,8-trimethoxycoumarin
• 英文别名: 5,7,8-trimethoxychromen-2-one
• CAS: 60796-65-8
• 化学式: C₁₂H₁₂O₅
• 分子量: 236.224
• InChiKey: MSFXSDYNQKVMTJ-UHFFFAOYSA-N

物化性质

• 熔点：
  178 °C
• 沸点：
  422.7±45.0 °C(Predicted)
• 密度：
  1.249±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。
• 保留指数：
  2107

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2932209090

反应信息

• 作为产物：
  描述：

  2-hydroxy-3,4,6-trimethoxybenzaldehyde 、 甲氧羰基亚甲基三苯基正膦 以 various solvent(s) 为溶剂， 反应 4.0h， 以72%的产率得到5,7,8-三甲氧基香豆素
  参考文献：
  名称：

  天然存在的5,6,7-和5,7,8-三加氧香豆素的全合成

  摘要：

  描述了五种天然存在的多加氧香豆素的合成。它涉及两个5,6,7-三加氧香豆素，即6-羟基-5,7-二甲氧基香豆素（fraxinol）1和5,6,7-三甲氧基香豆素2，以及三个5,7,8-三加氧的香豆素，即8-羟基-5,7-二甲氧基（leptodactylone）3，5,7,8- trimethoxycoumarin 4和8-（3-甲基-2-丁烯氧基）-5,7-二甲氧基（artanin）5。合成途径的关键特征是合成合适的四氧化苯甲醛，然后通过维蒂希反应将其转化为相应的香豆素。

  DOI：

  10.1016/j.tet.2008.02.059

文献信息

• Highly oxygenated coumarins from Pelargonium sidoides,
  作者：O Kayser

  DOI：10.1016/0031-9422(95)00166-5

  日期：1995.7

  Abstract The range of natural simple coumarins is extended by discovery of the highly oxygenated representatives 6,8-dihydroxy-7-methoxycoumarin, 6,7,8-trihydroxycoumarin, 6,8-dihydroxy-5,7-dimethoxycoumarin, and 7-acetoxy-5,6-dimethoxycoumarin. They are accompanied in the roots of Pelargonium sidoides by the widely occurring scopoletin, associated withtthe uncommon analogues 5,6,7-trimethoxycoumarin

  摘要 通过发现高度氧化的代表 6,8-二羟基-7-甲氧基香豆素、6,7,8-三羟基香豆素、6,8-二羟基-5,7-二甲氧基香豆素和 7-乙酰氧基香豆素，扩展了天然简单香豆素的范围。 -5,6-二甲氧基香豆素。它们在天竺葵的根部伴随着广泛存在的东莨菪碱，与不常见的类似物 5,6,7-三甲氧基香豆素、7-羟基-5,6-二甲氧基香豆素 (umckalin) 和 5,6,7,8-四甲氧基香豆素有关（artelin），这些是第二次从植物来源报道的。这些化合物的结构是通过化学和光谱研究确定的。在化学位移数据的基础上讨论了氧合模式之间的区别。
• Toward establishing structure–activity relationships for oxygenated coumarins as differentiation inducers of promonocytic leukemic cells
  作者：María E. Riveiro、Dominick Maes、Ramiro Vázquez、Monica Vermeulen、Sven Mangelinckx、Jan Jacobs、Silvia Debenedetti、Carina Shayo、Norbert De Kimpe、Carlos Davio

  DOI：10.1016/j.bmc.2009.08.002

  日期：2009.9

  The presumption that some coumarins might be lead compounds in the search for new differentiation agents against leukemia is based on the fact that natural coumarins, 5-(3-methyl-2-butenyloxy)-6,7-methylenedioxycoumarin (C-2) and 5-methoxy-6,7-methylenedioxycoumarin (C-1) inhibit proliferation and induce differentiation in U-937 cells [Riveiro, M. E.; Shayo, C.; Monczor, F.; Fernandez, N.; Baldi, A.; De Kimpe, N.; Rossi, J.; Debenedetti, S.; Davio, C. Cancer Lett. 2004, 210, 179-188]. These promising findings prompted us to investigate the anti-leukemia activity of a broader range of related polyoxygenated coumarins. Twenty related natural or synthetically prepared coumarins, including a range of 5-substituted ayapin derivatives which have become easy accessible via newly developed synthesis methods, were evaluated, where treatments with 5-(2,3-dihydroxy-3-methylbutoxy)-6,7-methylenedioxycoumarin (D-3) and 5-(2-hydroxy-3-methoxy-3-methylbutoxy)-6,7-methylenedioxycoumarin (D-2) were able to inhibit the cell growth and induce the differentiation of U-937 cells after 48 h treatment. These results provide insight into the correlation between some structural properties of polyoxygenated coumarins and their in vitro leukemic differentiation activity. (C) 2009 Elsevier Ltd. All rights reserved.
• [EN] PRICKLY ASH PREPARATIONS AND USES THEREOF AS ANTIVIRAL AGENTS<br/>[FR] PREPARATIONS A BASE DE CLAVALIER D'AMERIQUE ET LEURS UTILISATIONS COMME AGENTS ANTIVIRAUX
  申请人：BIONICHE LIFE SCIENCES INC

  公开号：WO2006026853A1

  公开（公告）日：2006-03-16

  The present invention provides the use of Z. americanum OR Z. clava-herculis tissue for the preparation of antival agents. The invention also provides a composition for use in treating a viral infection comprising a pyranocoumarin enriched preparation derived from Z. americanum or Z. clava-herculis. The invention also provides a composition containing phenolic or polyphenolic compounds from Z. americanum, which is substantially devoid of furanocoumarins. The invention further provides methods for providing a pyranocoumarin enriched preparation derived from Z. americanum.