4115-76-8

Basic information

• Product Name: 7-HYDROXY-4,8-DIMETHYLCOUMARIN
• Synonyms: 7-HYDROXY-4,8-DIMETHYLCOUMARIN;4,8-Dimethyl-7-hydroxy-2H-1-benzopyran-2-one;7-Hydroxy-4,8-dimethyl-2H-1-benzopyran-2-one;8-Methyl-7-hydroxy-4-methyl-2H-1-benzopyran-2-one;2H-1-Benzopyran-2-one,7-hydroxy-4,8-diMethyl-;4, 8-Dimethylumbelliferone;4,8-Dimethyl-7-hydroxycoumarin;4,8-Dimethylumbelliferone
• CAS NO: 4115-76-8
• Molecular Formula: C₁₁H₁₀O₃
• Molecular Weight: 190.1953
• Mol File: 4115-76-8.mol
• Article Data: 63

Chemical Properties

• Boiling Point: 375 °C at 760 mmHg
• Flash Point: 169.2 °C
• Appearance: /
• Density: 1.269 g/cm³
• Vapor Pressure: 3.71E-06mmHg at 25°C
• Refractive Index: 1.599
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 7-HYDROXY-4,8-DIMETHYLCOUMARIN(CAS DataBase Reference)
• NIST Chemistry Reference: 7-HYDROXY-4,8-DIMETHYLCOUMARIN(4115-76-8)
• EPA Substance Registry System: 7-HYDROXY-4,8-DIMETHYLCOUMARIN(4115-76-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 4115-76-8(Hazardous Substances Data)

Usage

General Description

7-HYDROXY-4,8-DIMETHYLCOUMARIN is a chemical compound that belongs to the coumarin family. It is a derivative of coumarin with a hydroxy group at the 7th position and methyl groups at the 4th and 8th positions. 7-HYDROXY-4,8-DIMETHYLCOUMARIN is known for its potential pharmaceutical and industrial applications, including its use as a flavoring agent, fragrance, and in the synthesis of pharmaceutical drugs. 7-HYDROXY-4,8-DIMETHYLCOUMARIN has also been studied for its antioxidant, anti-inflammatory, and antimicrobial properties, making it a subject of interest in the field of natural products chemistry and drug discovery. Overall, the compound has a diverse range of applications and potential biological activities that warrant further research and exploration.

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

Upstream product

• 14003-96-4 8-formyl-4-methyl-7-hydroxycoumarin 
• 7664-93-9 sulfuric acid 
• 608-25-3 2-methylbenzene-1,3-diol 
• 141-97-9 ethyl acetoacetate 
• 141-78-6 ethyl acetate 
• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 105-45-3 acetoacetic acid methyl ester 
• 504-15-4 orcinol 
• 74-88-4 methyl iodide 

Downstream Products

• 93087-54-8 4,8-dimethyl-2-oxo-2H-chromen-7-yl acetate 
• 3993-43-9 7-allyloxy-4,8-dimethyl-2H-chromen-2-one 
• 73290-83-2 6,7-Dihydro-4,8,8,10-tetramethyl-2H,8H-benzo<1,2-b:5,4-b'>dipyran-2-one 
• 109028-96-8 4,8-dimethyl-7-(2'-oxocyclohexyloxy)coumarin 
• 130278-47-6 6,7-Dihydro-4,8,10-trimethyl-2H,8H-benzo<1,2-b:5,4-b'>dipyran-2-one 
• 69897-63-8 4,8-dimethyl-7-<(β-chloroalllyl)oxy>coumarin 
• 85878-74-6 4,8-dimethyl-7-(3-nitro-4-pyridyloxy)coumarin 
• 69897-62-7 4,8-dimethyl-7-(prop-2-yn-1-yloxy)-2H-chromen-2-one 
• 23863-90-3 1,3-bis(4'-methylcoumarin-7'-oxy)-2-hydroxypropane 
• 125733-66-6 C₂₅H₂₄O₇ 
• 137449-17-3 1,3-bis(6'-ethyl-4'-methylcoumarin-7'-oxy)-2-hydroxypropane 
• 76387-84-3 7-hydroxy-4,8-dimethylcoumarin dimethylthiocarbamate 
• 145801-08-7 7-cinnamyloxy-4,8-dimethylcoumarin 
• 72478-66-1 4,8-dimethyl-7-<(β-bromoallyl)oxy>coumarin 

Relevant articles and documents

Design, synthesis and aggregation induced emission properties of two bichromophores with a triphenylamine-coumarin dyad structure

On the basis of molecular design about the donor-acceptor (D-A) triphenylamine-coumarin (TPA-coumarin) dyad, two new bichromophores 7-butoxy-6-(4-(diphenylamino)phenyl)-4,8-dimethyl-2H-chromen-2-one (TC) and 7-butoxy-6-(4-(diphenylamino)phenyl)-8-methyl-4-(trifluoromethyl)-2H-chromen-2-one (TF), were synthesized and characterized by using IR, 1H NMR, 13C NMR and HRMS. Both TC and TF exhibited the expected solid-state fluorescence emission due to the aggregation induced emission effect and different degrees of positive solvatochromism due to their different molecular conformations in various solvents. Owing to the different push-pull electronic effects of substituents on the coumarin moiety, TC and TF, acting as the D-A compounds, showed different HOMO-LUMO gaps and a variable red-shifted emission in their solid-state, substantiating the possibility to effectively tune the photophysical properties of these bichromophores by rational molecular design.

Discovery of triaromatic flexible agents bearing 1,2,3-Triazole with selective and potent anti-breast cancer activity and CDK9 inhibition supported by molecular dynamics

This study reports an efficient and convenient click synthesis of novel series of chromene scaffold linked to 1,2,3 triazole ring and terminal lipophilic fragments. Structures of all newly synthesized compounds were well characterized by IR, 1H NMR, 13C NMR and elemental analyses. In vitro MTT cytotoxic screening was performed using staurosporine as a reference drug against three different types: aggressive and invasive human breast cancer cell line (MDA-MB 231), Michigan cancer foundation-7 (MCF-7) and human colorectal carcinoma cell line (HCT116). These screening data showed considerable anticancer activity for these newly synthesized compounds compared to reference staurosporine drug with high degree of cell line selectivity and excellent activity with micromolar (μM) half maximal inhibitory concentration (IC50) values against tumor cells. In addition, Cyclin-Dependent Kinase1 and 9 (CDK1 and 9) assays were performed for the most active compounds to get more details about their mechanism of action. In order to assess and explain their binding affinities, molecular docking simulation was studied against CDK9 site. The results obtained from molecular docking study and those obtained from cytotoxic screening and enzyme inhibition were correlated. One of the most prominent analogs is 34 that showed high selective cytotoxicity profile against single breast cancer cell line MCF-7 and MDA-MB 231 with IC50 3.4 μM and 1.4 uM respectively. Molecular dynamics (MD) simulation of the CDK9 complex by Desmond revealed stability during 100 ns with RMSD of CDK9 complex converged at 2.1 ? after 20 ns. During MD, the interaction fractions confirmed multiple interactions of 34 with Cys106, a crucial residue for inhibition of CDK9 activity. A novel 34 triazole compound was introduced for drug design works as potent and selective hit for treatment of breast cancers after processing of optimization steps.

Design, synthesis, and antifungal evaluation of novel coumarin-pyrrole hybrids

A series of coumarin derivatives bearing a pyrrole scaffold were designed, prepared, and assessed for their in vitro antifungal activities against six phytopathogenic fungi. The antifungal activity screening results suggest that some synthesized hybrids exhibited potential fungicidal activities against the tested fungi. In particular, compounds 6j, 6k, 6o, 6p, and 6r displayed significant antifungal effects against Rhizoctorzia solani, and possessed EC50 values of 3.94, 7.75, 6.38, 6.25, and 7.67 μg/ mL, respectively. The above activities are more potent than the commercialized fungicide Boscalid (11.52 μg/mL) and Osthole (9.79 μg/mL). These results provide a significant reference for further rational design of coumarin-based fungicides.