55004-77-8

Usage

Uses

Used in Perfume and Cosmetic Industry:
4-HYDROXY-6 7-DIMETHYLCOUMARIN 98 is used as a fixative in fragrances for its sweet and fresh odor, helping to enhance and prolong the scent of perfumes and other scented products.
Used in Food and Beverage Industry:
4-HYDROXY-6 7-DIMETHYLCOUMARIN 98 is used as a flavoring agent in food products and beverages, imparting a unique taste and aroma to these products.
Used in Pharmaceutical Industry:
4-HYDROXY-6 7-DIMETHYLCOUMARIN 98 has potential medicinal properties, such as antioxidant and anti-inflammatory effects. It is being studied for its potential use in treating certain conditions, making it a promising candidate for pharmaceutical applications.

InChI:InChI=1/C11H10O3.H2O/c1-6-3-8-9(12)5-11(13)14-10(8)4-7(6)2;/h3-5,12H,1-2H3;1H2

Upstream product

• 36436-65-4 2-acetyl-4,5-dimethylphenol 
• 105-58-8 Diethyl carbonate 
• 22618-23-1 3,4-dimethylphenyl acetate 
• 95-65-8 3,4-Dimethylphenol 

Downstream Products

• 98411-90-6 5-(2-Hydroxy-4,5-dimethyl-phenyl)-2-methyl-2,4-dihydro-pyrazol-3-one 
• 1152668-63-7 4-(4-methoxyphenyl)-6,7-dimethyl-2H-chromen-2-one 
• 1152668-68-2 C₁₇H₁₃ClO₂ 
• 1187472-23-6 6,7-dimethyl-4-(phenylethynyl)-2H-chromen-2-one 
• 1609132-89-9 C₃₉H₂₈O₃ 
• 1449795-52-1 C₂₅H₁₉NO₂ 
• 1446694-18-3 C₃₃H₂₆N₂O₆ 
• 1416056-15-9 4-O-benzoyl-6,7-dimethylcoumarin 

Relevant academic research and scientific papers

Synthesis and anti-inflammatory activity of 2-oxo-2H-chromenyl and 2H-chromenyl-5-oxo-2,5-dihydrofuran-3-carboxylates

Cycloaddition reaction of 4-chloro-2-oxo-2H-chromene-3-carbaldehydes (3a-g) and 4-chloro-2H-chromene-3-carbaldehydes (7a-h) with activated alkynes (4a-b) provided the 2-oxo-2H-chromenyl-5-oxo-2,5-dihydrofuran-3-carboxylates (5a-n) and 2H-chromenyl-5-oxo-2,5-dihydrofuran-3-carboxylates (8a-p). All the prepared compounds were screened for anti-inflammatory activity. In vitro anti-inflammatory activity data demonstrated that the compounds 5g, 5i, 5k-l and 8f are effective among the tested compounds against TNF-α (1.108 ± 0.002, 0.423 ± 0.022, 0.047 ± 0.001, 0.070 ± 0.002 and 0.142 ± 0.001 μM) in comparison with standard compound Prednisolone (0.033 ± 0.002 μM). Based on in vitro results, three compounds (5i, 5k and 8f) have been selected for in vivo experiments and these compounds are identified as better compounds with respect to anti-inflammatory activity in LPS induced mice model. Compound 5i was identified as potent and showed significant reduction in TNF-α and IL-6.

Regioselective Synthesis of 4,5-Dihydro-6H-oxepino[3,2-c]chromene-2,6(3H)-diones through Palladium-Catalyzed Intramolecular Alkoxycarbonylation of 3-Allyl-4-hydroxycoumarins

Seven-membered ring lactones fused to coumarin scaffolds were obtained via a palladium-catalyzed regioselective intramolecular alkoxycarbonylation under a CO atmosphere. Cyclocarbonylation of 3-allyl-4-hydroxycoumarin derivatives was accessed in the absen

Affinity-based small fluorescent probe for NAD(P)H:quinone oxidoreductase 1 (NQO1). Design, synthesis and pharmacological evaluation

NQO1 is a dimeric flavoprotein which intimately associated with cancer and overexpressed in the cytosol of numerous human tumor cells. Given that the cellular environment is quite dynamic and versatile, further investigation of the function of NQO1 depends on tools for specific detection of it. Currently, several activity-based assays have been developed to detect NQO1-expressing cancerous tissues. Herein, we report the development of a functional affinity-based small-molecule probe which is composed of a potent small-molecule NQO1 inhibitor 3d as the recognition group, a linker and the fluorophores group FITC. The probe exhibits good inhibitory activity of NQO1 and has been successfully used to label the protein in A549 cells at the micromolar level. These features make the probe favorable for mechanistic studies and cancer diagnostic biomarker. Based on these preliminary results, our laboratory will focus on the further development of fluorescent probe for NQO1, which could be anticipated to be applied in physiological and pathological studies of NQO1.

Palladium-catalyzed [2+2+1] oxidative annulation of 4-hydroxycoumarins with unactivated internal alkynes: Access to spiro cyclopentadiene-chroman-2,4-dione complexes

Herein, we report our new results regarding a palladium-catalyzed [2+2+1] oxidative annulation of 4-hydroxycoumarins with unactivated internal alkynes, which affords a new class of compounds: the spiro cyclopentadiene-chroman-2,4- diones.

Palladium-catalyzed oxidative annulation via C-H/N-H functionalization: Access to substituted pyrroles

Pyrroles, ubiquitous bioactive heterocycles in nature, are readily prepared via a palladium-catalyzed oxidative annulation of cyclic trans-enamines to various internal alkynes in the absence of a directing group. Copyright

Use of 4-cyanocoumarins as dienophiles in a facile synthesis of highly substituted dibenzopyranones

(Chemical Equation Presented) A new synthesis of dibenzopyranones 14 is reported via the Diels-Alder cycloaddition of 4-cyanocoumarins 12 with 1-silyloxydienes 10 to give the adducts 13 which are then converted into 14 in one step via treatment with base and loss of the cyano and silyloxy groups.

Synthesis and biological evaluation of coumarin-based inhibitors of NAD(P)H: Quinone oxidoreductase-1 (NQO1)

The synthesis is reported here of two novel series of inhibitors of human NAD(P)H quinone oxidoreductase-1 (NQO1), an enzyme overexpressed in several types of tumor cell. The first series comprises substituted symmetric dicoumarol analogues; the second series contains hybrid compounds where one 4-hydroxycoumarin systemis replaced by a different aromatic moiety. Several compounds show equivalent or improved NQO1 inhibition over dicoumarol, both in the presence and in the absence of added protein. Further, correlation is demonstrated between the ability of these agents to inhibit NQO1 and computed binding affinity. We have solved the crystal structure of NQO1 complexed to a hybrid compound and find good agreement with the in silico model. For both MIA PaCa-2 pancreatic tumor cells and HCT116 colon cancer cells, dicoumarol shows the greatest toxicity of all compounds. Thus, we provide a computational, synthetic, and biological platform to generate competitive NQO1 inhibitors with superior pharmacological properties to dicoumarol. This will allow a more definitive study of NQO1 activity in cells, in particular, its drug activating/detoxifying properties and ability to modulate oncoprotein stability. 2009 American Chemical Society.

Coumarin derivatives for the treatment of allergies

Pharmaceutical compositions for the treatment of allergies are produced using coumarin derivatives as the active agent. Certain of these compounds and their salts are novel.