2107-77-9

Usage

Uses

Used in Chemical Synthesis:
7,8-DIHYDROXY-4-METHYLCOUMARIN is used as a fluorescent sensor for monitoring the consumption of a boronic acid in a Suzuki cross-coupling reaction. This application is particularly useful in the field of chemical synthesis, where precise monitoring of reaction progress is crucial for achieving desired outcomes.
Used in Analytical Chemistry:
In the field of analytical chemistry, 7,8-DIHYDROXY-4-METHYLCOUMARIN serves as a valuable tool for detecting and quantifying specific chemical species. Its fluorescent properties allow for the sensitive detection of boronic acid, making it an essential component in the development of new analytical methods and techniques.
Used in Research and Development:
7,8-DIHYDROXY-4-METHYLCOUMARIN is also utilized in research and development, where its unique properties can be explored for potential applications in various scientific disciplines. The compound's ability to act as a fluorescent sensor opens up possibilities for its use in the creation of new diagnostic tools, imaging agents, and other innovative technologies.
Used in Pharmaceutical Industry:
The pharmaceutical industry may benefit from the use of 7,8-DIHYDROXY-4-METHYLCOUMARIN as a starting material or intermediate in the synthesis of new drugs. Its solid state and chemical properties make it a promising candidate for further exploration and development in the context of drug discovery and design.
Used in Material Science:
In material science, 7,8-DIHYDROXY-4-METHYLCOUMARIN could be investigated for its potential to contribute to the development of new materials with unique optical, electronic, or mechanical properties. Its solid state and chemical characteristics may be harnessed to create novel materials with specific applications in various industries.
Overall, 7,8-DIHYDROXY-4-METHYLCOUMARIN is a versatile compound with a wide range of potential applications across different industries, including chemical synthesis, analytical chemistry, research and development, pharmaceuticals, and material science. Its unique properties, such as its ability to function as a fluorescent sensor and its solid state, make it a valuable asset in the ongoing pursuit of scientific and technological advancements.

InChI:InChI=1/C10H8O4/c1-5-4-8(12)14-10-6(5)2-3-7(11)9(10)13/h2-4,11,13H,1H3

Upstream product

• 674-82-8 4-methyleneoxetan-2-one 
• 87-66-1 2-hydroxyresorcinol 
• 14003-96-4 8-formyl-4-methyl-7-hydroxycoumarin 
• 141-97-9 ethyl acetoacetate 
• 92098-63-0 4-methylchromene-2,7,8-trione 
• 1560-54-9 allyltriphenylphosphonium bromide 
• 1530-34-3 (3-methylbut-2-enyl)triphenylphosphonium bromide 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 20913-05-7 (Benzoylmethylene)triphenylphosphorane 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 75-77-4 chloro-trimethyl-silane 
• 64-19-7 acetic acid 
• 68454-15-9 7,8-diacetoxy-4-methylcoumarin 

Downstream Products

• 14002-97-2 4-methyl-7,8-dimethoxycoumarin 
• 382174-30-3 7,8-dibenzyloxy-4-methylchromen-2-one 
• 62113-97-7 4-methyl-2-oxo-2H-chromene-7,8-diyl dimethanesulfonate 
• 859922-36-4 8-hydroxy-4-methyl-7-(toluene-4-sulfonyloxy)-coumarin 
• 22084-94-2 8-Hydroxy-7-methoxy-4-methyl-cumarin 
• 16574-14-4 4-methyl-6,7,8-trihydroxycoumarin 
• 132961-70-7 8-methoxy-4-methyl-7-(toluene-4-sulfonyloxy)-coumarin 
• 857782-59-3 7,8-bis-benzyloxy-3-bromo-4-methyl-coumarin 
• 186303-90-2 4-methyl-7,8-diretinoyloxy-coumarin 

Relevant academic research and scientific papers

Coumarins: Facile and expeditious synthesis via keggin-type heteropolycompounds under solvent-free condition

Different Keggin-type heteropolycompounds were used in Pechmann reaction to obtain biologically active coumarins. Effect of solvent, catalyst loading, and molar ratios of substrates was studied to introduce the best reaction condition. The optimized reaction condition was extended to Pechmann reaction of methylacetoacetate with various monohydric and polyhydric phenols. This rapid procedure afforded structurally diverse coumarins with high to excellent yields. Short reaction times, simple work-up, and mild reaction conditions were advantages of this method. The optimized catalysts were reusable for four runs.

Targeted photoresponsive TiO2-coumarin nanoconjugate for efficient combination therapy in MDA-MB-231 breast cancer cells: Synergic effect of photodynamic therapy (PDT) and anticancer drug chlorambucil

Coupling of photodynamic therapy (PDT) with chemotherapy is an emerging treatment modality because of its ability to improve the antitumor effect and reduce the toxicity of the anticancer agents. Metallic NPs, silica NPs and carbon nanotubes have become r

Novel coumarins and benzocoumarins acting as isoform-selective inhibitors against the tumor-associated carbonic anhydrase IX

A series of coumarins and benzocoumarins incorporating methyl and hydroxyl moieties in the heterocyclic ring were investigated for the inhibition of the zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1). These coumarins were very weak or ineffective as inhibitors of the house-keeping, offtarget isoforms CA I and II, but showed effective, submicromolar inhibition of the transmembrane, tumor-associated isoforms CA IX and to a slightly less extent, CA XII. The nature and position of the groups substituting the coumarin ring influenced CA inhibitory properties. 4-Methyl-5,7-dihydroydroxycoumarin showed KIs >200 μM against CA I and II, of 0.19 μM against CA IX and of 6.4 μM against CA XII, being thus a selective, efficient inhibitor for the tumor-associated over cytosolic CA isoforms. These compounds are interesting leads for designing isoform-selective enzyme inhibitors.

Reactions of 4-methylchromene-2,7,8-trione with phosphonium ylides. Synthesis and evaluation of fused 1,3-dioxolocoumarins as antioxidants and antiinflammatories

4-Methylchromene-2,7,8-trione 1 reacts with stabilized 2a-c and non-stabilized ylides 11a-c bearing an α-methylene group to give 7,8-fused 1,3-dioxolocoumarins 4a-c and 12a-c along with betaine 6 and 7-hydroxycoumarin derivative 9. The reaction of 4,5-fused 1,3-dioxolo-o-benzoquinone 13 with the ylide 14 leads to 4-ethoxycarbonylayapin 18 and benzofuranone 19. Deethoxycarbonylation of 18 gives ayapin 20. Compounds 4b, 12a-c, 18 and 20 were tested for their ability to interact with 1,1-diphenyl-2-picrylhydrazyl stable free radical (DPPH), to scavenge superoxide anion radicals, to compete with DMSO for hydroxyl radicals, and to inhibit proteolysis, β-glucuronidase and soybean lipoxygenase activity in vitro. These compounds were also tested for their effect on the ferrous ion-stimulated peroxidation of linoleic acid. They showed a potent inhibitory effect (55-57%) against inflammation induced by carrageenan in the rat paw edema model. On the contrary their reducing ability was found to be low and no inhibition on soybean lipoxygenase was recorded.

FeCl3-catalyzed Pechmann synthesis of coumarins in ionic liquids

The synthesis of coumarin derivatives via Pechmann reaction using anhydrous FeCl3 as Lewis acid catalyst in ionic liquid medium has been carried out. The best results were obtained (yields as high as 89%) with ionic liquids having bis(triflic)imide as a counteranion. The ionic liquid could easily be recovered and reused. Copyright Taylor & Francis Group, LLC.

Recyclable CMK-5 supported sulfonic acid as an environmentally benign catalyst for solvent-free one-pot construction of coumarin through Pechmann condensation

Sulfonic acid modified nanostructured CMK-5 is used as an alternative to conventional acid catalysts in the von Pechmann condensation of a neat mixture of substituted phenols with ethyl acetoacetate leading to the formation of coumarin derivatives at 130 °C. In comparison, CMK-5-SO3H showed a greater activity than some other homogeneous and heterogeneous catalysts. Additionally, the catalyst is reused repeatedly for 6 reaction cycles without any evidence of loss of activity, confirming the stability of the covalent bonding of acidic centers. The methodology presented offers reusable strategy for the efficient synthesis of coumarin, simplicity in operation, and green aspects by avoiding toxic conventional catalysts and solvents.

Protein acyltransferase function of purified calreticulin. Part 1: Characterization of propionylation of protein utilizing propoxycoumarin as the propionyl group donor

We have earlier reported that an endoplasmic reticulum luminal protein calreticulin (CR) mediated the acetylation of certain receptor proteins such as glutathione S-transferase (GST) by polyphenolic acetates, leading to irreversible inhibition. This function of calreticulin was termed calreticulin transacetylase. In this communication, we have demonstrated for the first time the ability of the purified recombinant calreticulin of a parasitic nematode Haemonchus contortus to transfer propionyl group from 7,8-Dipropoxy-4- methylcoumarin (DPMC) to recombinant Schistosoma japonicum glutathione S-transferase (rGST). Calreticulin transacetylase exhibited hyperbolic kinetics and yielded Km (140 μM) and Vmax (105 units) when the concentration of DPMC was varied keeping the concentration of rGST constant. rGST thus propionylated was found to positively interact with anti-acetyl lysine antibody. Also, the nanoscale LC-MS/MS analysis identified the propionylation sites on three lysine residues: Lys-11, -180 and -181 of rGST. These results highlight the transacylase function of calreticulin (CRTAase). The Authors 2009. Published by Oxford University Press on behalf of the Japanese Biochemical Society. All rights reserved.

Novel Fe3+-based 1H MRI β-galactosidase reporter molecules

There is increasing interest in the development of reporter agents to reveal enzyme activity in vivo using imaging in small animals. We have previously demonstrated the feasibility of detecting lacZ gene activity using the commercially available 3,4-cyclohexenoesculetin-β-D-galactopyranoside (S-Gal) as a 1H MRI reporter. Specifically, β-galactosidase (β-gal) releases the aglycone, which forms a magnetic resonance contrast-inducing paramagnetic precipitate in the presence of Fe3+. Contrast was primarily T2-weighted signal loss, but T1 effects were also observed. Since T1-contrast generally provides signal enhancement as opposed to loss, it appeared attractive to explore whether analogues could be generated with enhanced characteristics. We now report the design and synthesis of novel analogues together with characterization of 1H MRI contrast based on both T1 and T2 response to b-gal activity in vitro for the lead agent.

Acetoxy drug: Protein transacetylase catalyzed activation of human platelet nitric oxide synthase by polyphenolic peracetates

An enhanced intracellular level of Nitric oxide (NO) is essential to ameliorate several pathological conditions of heart and vasculature necessitating the activation of NOS. We have projected in this report the acetylation of eNOS by polyphenolic peracetates (PA) catalyzed by the novel enzyme acetoxy drug: protein transacetylase (TAase) discovered in our laboratory as an unambiguous way of activating NOS which results in the manifestation of physiological action. The human platelet was chosen as the experimental system in order to validate the aforementioned proposition. PA caused profound irreversible activation of platelet NADPH cytochrome c reductase mediated by TAase. The convincing biochemical evidences are presented to show that PA could cause acetylation of the reductase domain of NOS leading to the activation of eNOS in tune with their specificities to platelet TAase. As a result, the enhanced level of NO due to activation of platelet eNOS by PA was found to inhibit the ADP-induced platelet aggregation. The present studies highlight for the first time the role of PA as the novel potent agent for enhancing the intracellular NO levels.

Regioselective IBX-Mediated Synthesis of Coumarin Derivatives with Antioxidant and Anti-influenza Activities

Different catechol and pyrogallol derivatives have been synthesized by oxidation of coumarins with 2-iodoxybenzoic acid (IBX) in DMSO at 25 °C. A high regioselectivity was observed in accordance with the stability order of the incipient carbocation or radical benzylic-like intermediate. The oxidation was also effective in water under heterogeneous conditions by using IBX supported on polystyrene. The new derivatives showed improved antioxidant effects in the DPPH test and inhibitory activity against the influenza A/PR8/H1N1 virus. These data represent a new entry for highly oxidized coumarins showing an antiviral activity possibly based on the control of the intracellular redox value.