60796-65-8

Usage

Uses

Used in Pharmaceutical Industry:
5,7,8-Trimethoxycoumarin is used as a potential therapeutic agent for its possible anti-coagulant, anti-tumor, anti-inflammatory, and antimicrobial properties. These biological activities suggest that it could be a candidate for the development of new drugs, particularly in the treatment of various diseases where these properties are beneficial.
Used in Research Applications:
5,7,8-Trimethoxycoumarin is used as a research compound for studying the structure-activity relationships of coumarin derivatives. Understanding how the presence of methoxy groups at specific positions affects the biological activity can provide insights into the design of more effective and targeted therapeutic agents.
Used in Chemical Synthesis:
5,7,8-Trimethoxycoumarin is used as a starting material or intermediate in the synthesis of more complex coumarin-based compounds. Its unique structure can be further modified to create novel molecules with potential applications in various fields, such as medicine, agriculture, or materials science.
Used in Analytical Chemistry:
5,7,8-Trimethoxycoumarin can be used as a reference compound or standard in analytical methods for the identification and quantification of coumarin derivatives. Its distinct chemical properties can help in the development of more accurate and reliable analytical techniques.
Used in Material Science:
5,7,8-Trimethoxycoumarin may be used in the development of new materials with specific properties, such as fluorescence or photoreactivity. Its incorporation into polymers or other materials could lead to innovative applications in areas like sensors, imaging, or photovoltaics.

Upstream product

• 65162-31-4 2-hydroxy-3,4,6-trimethoxybenzaldehyde 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 52249-80-6 2,4-dihydroxy-3,6-dimethoxybenzaldehyde 
• 127-09-3 sodium acetate 
• 108-24-7 acetic anhydride 
• 77-78-1 dimethyl sulfate 

Relevant academic research and scientific papers

HIGHLY OXYGENATED COUMARINS FROM PELARGONIUM SIDOIDES

The sample 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 occuring scopoletin, associated with the uncommon analoges 5,6,7-trimethoxycoumarin, 7-hydroxy-5,6-dimethoxycoumarin (umckalin), and 5,6,7,8-tetramethoxycoumarin (artelin), these being reported from a plant source for the second time.The structures of these compounds were established from chemical and spectroscopic studies.Differentiation between oxygenation patterns is discussed on the basis of chemical shift data.

Toward establishing structure-activity relationships for oxygenated coumarins as differentiation inducers of promonocytic leukemic cells

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.

Total synthesis of naturally occurring 5,6,7- and 5,7,8-trioxygenated coumarins

The synthesis of five naturally occurring polyoxygenated coumarins is described. It concerns two 5,6,7-trioxygenated coumarins, i.e., 6-hydroxy-5,7-dimethoxycoumarin (fraxinol) 1 and 5,6,7-trimethoxycoumarin 2, and three 5,7,8-trioxygenated coumarins, i.e., 8-hydroxy-5,7-dimethoxycoumarin (leptodactylone) 3, 5,7,8-trimethoxycoumarin 4 and 8-(3-methyl-2-butenyloxy)-5,7-dimethoxycoumarin (artanin) 5. Key feature of the synthetic pathway is the synthesis of suitable tetraoxygenated benzaldehydes, which are then converted to the corresponding coumarins via a Wittig reaction.