487-06-9

Usage

Uses

Used in Photodynamic Therapy:
5,7-Dimethoxycoumarin is used as a photosensitizing agent for photodynamic therapy. It plays a crucial role in the treatment of various types of cancer by generating reactive oxygen species upon light activation, leading to the destruction of cancerous cells.
Used in Pharmaceutical Industry:
5,7-Dimethoxycoumarin is used as a chemical intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and properties make it a valuable building block for the development of new drugs with potential applications in different therapeutic areas.
Used in Research and Development:
5,7-Dimethoxycoumarin is utilized as a research tool in the study of genetic mutations and cellular processes. Its ability to induce frameshift mutagenesis and affect sister chromatid exchanges makes it a valuable compound for understanding the mechanisms underlying these biological events.
Used in Analytical Chemistry:
5,7-Dimethoxycoumarin can be employed as a fluorescent marker or probe in analytical chemistry. Its fluorescence properties allow for the detection and quantification of specific molecules or interactions, which can be useful in various analytical techniques and applications.

Synthesis Reference(s)

Journal of the American Chemical Society, 118, p. 6305, 1996 DOI: 10.1021/ja961107i

Biochem/physiol Actions

5,7-Dimethoxycoumarin induces the processes of differentiation and melanogenesis in murine (B16) and human (A375).

InChI:InChI=1/C11H10O4/c1-13-7-5-9(14-2)8-3-4-11(12)15-10(8)6-7/h3-6H,1-2H3

Upstream product

• 186581-53-3 diazomethane 
• 2732-18-5 5,7-dihydroxy-2H-chromen-2-one 
• 23053-61-4 5,7-dihydroxycoumarin 7-methyl ether 
• 67-56-1 methanol 
• 13221-57-3 2-hydroxy-4,6-dimethoxy-trans-cinnamic acid 
• 74-88-4 methyl iodide 
• 81017-27-8 5,7-dimethoxy-2-oxo-2H-chromene-3-carboxylic acid 
• 708-76-9 2-hydroxy-4,6-dimethoxybenzaldehyde 
• 108-24-7 acetic anhydride 
• 500-99-2 3,5-dimethoxyphenol 
• 6191-99-7 (2E)-3-ethoxyprop-2-enoyl chloride 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 85-32-5 Guanosine 5'-monophosphate 
• 82235-61-8 ethyl 5,7-dimethoxy-2-oxo-2H-chromene-3-carboxylate 

Downstream Products

• 486-28-2 fraxinol 
• 13221-57-3 2-hydroxy-4,6-dimethoxy-trans-cinnamic acid 
• 749879-24-1 3-(2-hydroxy-4,6-dimethoxy-phenyl)-propionic acid 
• 37719-98-5 glabra-lactone 
• 108-73-6 3,5-dihydroxyphenol 
• 64-19-7 acetic acid 
• 142878-03-3 toddacoumaquinone 
• 1427192-78-6 C₁₈H₁₆O₆ 
• 1427192-07-1 4-(3-(3,5-cis-dimethlpiperidin-1-yl)-3-oxo-1-(2,4,6-trimethoxyphenyl)-propyl)benzoic acid 
• 1427192-08-2 4-(3-(3,5-cis-dimethylpiperidin-1-yl)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-oxopropyl)benzoic acid 
• 1427192-12-8 1-(3,5-dimethylpiperidin-1-yl)-3-(4,6-dimethoxy-2-hydroxy-phenyl)-3-(2-methoxypyrid-5-yl)propan-1-one 
• 1427192-76-4 4-(3-(3,5-cis-dimethylpiperidin-1-yl)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-oxopropyl)benzoic acid, sodium salt 
• 17245-25-9 coumurrayin 
• 1334470-43-7 3-(3-(3,5-dimethylpiperidin-1-yl)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-oxopropyl)benzonitrile 

Relevant academic research and scientific papers

Amido compounds as RORγt modulators and uses thereof

Amido compounds are disclosed that have a formula represented by the following: and wherein Cy1, Cy2, n1, n2, R1a, R1b, R2, R3, R4, R5, and R6 are as described herein. The compounds may be prepared as pharmaceutical compositions, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example, inflammatory conditions, autoimmune disorders, cancer, and graft-versus-host disease.

Microwave-Assisted Synthesis of Phenylpropanoids and Coumarins: Total Synthesis of Osthol

Herein we describe a one-pot microwave-assisted method for the synthesis of cinnamic acid and coumarin derivatives. The synthesis begins with an aldehyde synthon, and the chosen reaction conditions determine whether a cinnamic acid or coumarin derivative is formed. A regioselective Claisen rearrangement was also efficiently incorporated into the synthetic sequence to further increase the complexity of the product. Notably, this approach provides high product yields and selectivities without the need of a phenol protecting group.

Rh-Catalyzed Synthesis of Coumarin Derivatives from Phenolic Acetates and Acrylates via C-H Bond Activation

An efficient annulation strategy involving the reaction of phenolic acetates with acrylates in the presence of [Rh2(OAc)4] as catalyst and formic acid as reducing agent, leading to the high yield synthesis of coumarin derivatives, has been developed. The addition of NaOAc as a base increased the yield of the products. The reaction is quite successful for both electron-rich as well as electron-deficient phenolic acetates, affording coumarins with excellent regioselectivity, and proceeds via C-H bond activation proven by deuterium incorporation studies.

Reduction of substituted phenyl 2-chloroacetates at silver cathodes: Electrosynthesis of coumarins

To explore the electrosynthesis of coumarins, cyclic voltammetry and controlled-potential (bulk) electrolysis have been employed to investigate the reduction of the carbon-chlorine bond of five substituted phenyl 2-chloroacetates at silver cathodes in dimethylformamide (DMF) containing 0.10 M tetra-n-butylammonium tetrafluoroborate (TBABF4) as supporting electrolyte; the five substrates are 2-formylphenyl 2-chloroacetate (1a), 2-acetylphenyl 2-chloroacetate (2a), methyl 2-(2-chloroacetoxy)benzoate (3a), 2-formyl-5-methoxyphenyl 2-chloroacetate (4a), and 2-formyl-3,5-dimethoxyphenyl 2-chloroacetate (5a). We have examined (a) the effects of substituents on the benzene ring of the substrate as well as the nature of the aryl carbonyl moiety on the formation of the coumarin product and (b) the effect of solvent - namely, DMF, acetonitrile (CH3CN), benzonitrile (PhCN), and propylene carbonate (PC) - and substrate concentration on the yield of the coumarin. It was found that the most unsubstituted substrate (1a) afforded the highest yield (41%) of the desired coumarin in a DMF-TBABF4 medium. A mechanistic scheme is proposed to account for the formation of the coumarin. Furthermore, the only other products seen in these reductions are 2-substituted phenols, which are precursors for synthesis of the various substrates.

AMIDO COMPOUNDS AS RORGAMMATMODULATORS AND USES THEREOF

Amido compounds are disclosed that have a formula represented by the following: 1 and wherein Cy1, Cy2, n1, n2, R1a, R1b, R2, R3, R4, R5, and R6 are as described herein. The compounds may be prepared as pharmaceutical compositions, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example, inflammatory conditions, autoimmune disorders, cancer, and graftversus-host disease

A catalyst-free one-pot construction of skeletons of 5-methoxyseselin and alloxanthoxyletin in water

In refluxing water and without an additional catalyst, electron-rich phenols could react with alkynoic acids or alkynoates to provide coumarin structures. The skeletons of two natural pyranocoumarins, 5-methoxyseselin and alloxanthoxyletin, could be constructed (total yield up to 76%) in an aqueous multicomponent reaction in which isoprenyl acetate, propiolic acid, and phloroglucinol were simply mixed and refluxed in water.

Cascade synthesis of 3-alkenylcoumarins by palladium-catalyzed reaction of phenols and ethyl propiolate

A highly effective cascade process giving 3-alkenylcoumarins is furnished by a series of reactions involving palladaarylation of ethyl propiolate with phenols, intramolecular transesterification to 3-coumarylpalladium species, its alkyne insertion, and protonation. [Pd(OAc)2(dppe)] is an effective catalyst for the synthesis of 3-alkenylcoumarins from phenols and ethyl propiolate.

New approach for the construction of the coumarin frame and application in the total synthesis of natural products

A new synthetic approach is described for building the coumarin scaffold through the Lewis acid-promoted cyclization of novel aryl 3-(dimethylamino)prop- 2-enoates 2a - 2f. The latter precursors were prepared via aminomethylenation of the corresponding aryl acetates 4a - 4f with the Bredereck reagent. This approach was used for the synthesis of biologically active natural compounds 1a - 1f, through a three-step procedure starting from the corresponding phenols.

Synthesis of coumarins and neoflavones through zinc chloride catalyzed hydroarylation of acetylenic esters with phenols

Acetylenic esters react with oxygenated phenols under solvent-free conditions in the presence of only 5 mol% of zinc chloride as a catalyst to give coumarins and neoflavones in reasonable-to-good yields. Georg Thieme Verlag Stuttgart. New York.

Improved synthesis of coumarins by iron(III)-catalyzed cascade reaction of propiolic acids and phenols

The reaction of propiolic acids with phenols in the presence of FeClAgOTf catalyst proceeded efficiently in a mixed solvent of trifluoroacetic acid and 1,2-dichloroethane, and provided coumarins in good to high yields. This iron-catalyzed reaction offers a much-improved synthesis of coumarins. Thieme Stuttgart New York.