19056-75-8

Usage

Molecular structure

The compound has a complex molecular structure that belongs to the chromen-4-one class of compounds.

Functional groups

It contains two methoxy groups, a hydroxy group, and a phenyl ring with two methoxy substituents.

Classification

It is a flavonoid, a class of compounds known for their antioxidant and anti-inflammatory properties.

Potential uses

The specific chemical structure of the compound suggests that it may have potential as a pharmaceutical drug or a natural product for use in health and wellness applications.

Further research needed

More research and testing is required to fully understand the potential uses and benefits of 2-(2,4-dimethoxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-chromen-4-one.

Upstream product

• 135566-98-2 5,7-dihydroxy-3,2',4'-trimethoxyflavone 
• 77-78-1 dimethyl sulfate 
• 7555-80-8 pentamethyl morin 
• 186581-53-3 diazomethane 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 75-18-3 dimethylsulfide 
• 480-16-0 morin 
• 613-45-6 2,4-Dimethoxybenzaldehyde 
• 64200-22-2 (E)-1-(2′-hydroxy-4′,6′-dimethoxyphenyl)-3-(2,4-dimethoxyphenyl)prop-2-en-1-one 
• 84757-50-6 2-(2,4-dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-4H-chromen-4-one 

Downstream Products

• 84757-51-7 2-(2,4-Dimethoxy-phenyl)-5,8-dihydroxy-3,7-dimethoxy-chromen-4-one 
• 91-52-1 2,4 dimethoxybenzoic acid 
• 1203579-91-2 2',3,4',7-tetramethoxy-5-hydroxyflavothione 
• 71787-04-7 5-hydroxy-3,7,8,2',4'-pentamethoxyflavone 

Relevant academic research and scientific papers

Neural Glyoxalase Pathway Enhancement by Morin Derivatives in an Alzheimer's Disease Model

The glyoxalase pathway (GP) is an antioxidant defense system that detoxifies metabolic byproduct methylglyoxal (MG). Through sequential reactions, reduced glutathione (GSH), glyoxalase I (glo-1), and glyoxalase II (glo-2) convert MG into d-lactate. Spontaneous reactions involving MG alter the structure and function of cellular macromolecules through the formation of inflammatory advanced glycation endproducts (AGEs). Accumulation of MG and AGEs in neural cells contributes to oxidative stress (OS), a state of elevated inflammation commonly found in neurodegenerative diseases including Alzheimer's disease (AD). Morin is a common plant-produced flavonoid polyphenol that exhibits the ability to enhance the GP-mediated detoxification of MG. We hypothesize that structural modifications to morin will improve its inherent GP enhancing ability. Here we synthesized a morin derivative, dibromo-morin (DBM), formulated a morin encapsulated nanoparticle (MNP), and examined their efficacy in enhancing neural GP activity. Cultured mouse primary cerebellar neurons and Caenorhabditis elegans were induced to a state of OS with MG and treated with morin, DBM, and MNP. Results indicated the morin derivatives were more effective compared to the parent compound in neural GP enhancement and preventing MG-mediated OS in an AD model.

Pharmacokinetics and Metabolites of 12 Bioactive Polymethoxyflavones in Rat Plasma

Polymethoxyflavones (PMFs) are a subgroup of flavonoids possessing various health benefits. 3,5,7,4′-Tetramethoxyflavone (1), 5,6,7,4′-tetramethylflavone (2), 3,7,3′,4′-tetramethoxyflavone (3), 5,7,3′,4′-tetramethoxyflavone (4), 5-hydroxy-3,7,2′,4′-tetramethoxyflavone (5), 3,5,7,2′,4′-pentamethoxyflavone (6), 5-hydroxy-3,7,3′,4′-tetramethoxyflavone (7), 3-hydroxy-5,7,3′,4′-tetramethylflavone (8), 3,5,7,3′,4′-pentamethoxyflavone (9), 5-hydroxy-3,7,3′,4′,5′-pentamethoxyflavone (10), 3-hydroxy-5,7,3′,4′,5′-pentamethoxyflavone (11), and 3,5,7,3′,4′,5′-hexamethoxylflavone (12) were 12 bioactive and available PMFs. The aim of this study was to investigate the pharmacokinetic, metabolite, and antitumor activities as well as the structure-pharmacokinetic-antitumor activity relationships of these 12 PMFs to facilitate further studies of their medicinal potentials. The cytotoxicity of PMFs with a hydroxy group toward HeLa, A549, HepG2, and HCT116 cancer cell lines was generally significantly more potent than that of PMFs without a hydroxy group. Compounds 5, 7, 8, 10, and 11 were all undetectable in rat plasma, while compounds 1-4, 6, 9, and 12 were detectable. Both the number and position of hydroxy and methoxy groups played an important role in modulating PMF pharmacokinetics and metabolites.

Synthesis and biological evaluation of flavones and benzoflavones as inhibitors of BCRP/ABCG2

Multidrug resistance (MDR) often leads to a failure of cancer chemotherapy. Breast Cancer Resistance Protein (BCRP/ABCG2), a member of the superfamily of ATP binding cassette proteins has been found to confer MDR in cancer cells by transporting molecules with amphiphilic character out of the cells using energy from ATP hydrolysis. Inhibiting BCRP can be a solution to overcome MDR.We synthesized a series of flavones, 7,8-benzofl avones and 5,6-benzo flavones with varying substituents at positions 3, 3′ and 4′ of the (benzo)fl avone structure. All synthesized compounds were tested for BCRP inhibition in Hoechst 33342 and pheophorbide A accumulation assays using MDCK cells expressing BCRP. All the compounds were further screened for their P-glycoprotein (P-gp) and Multidrug resistance-associated protein 1 (MRP1) inhibitory activity by calcein AM accumulation assay to check the selectivity towards BCRP. In addition most active compounds were investigated for their cytotoxicity. It was observed that in most cases 7,8-benzoflavones are more potent in comparison to the 5,6-benzoflavones. In general it was found that presence of a 3-OCH3 substituent leads to increase in activity in comparison to presence of OH or no substitution at position 3. Also, it was found that presence of 3′,4′-OCH3 on phenyl ring lead to increase in activity as compared to other substituents. Compound 24, a 7,8-benzoflavone derivative was found to be most potent being 50 times selective for BCRP and showing very low cytotoxicity at higher concentrations.

NMR of a series of novel hydroxyflavothiones

Alkylated hydroxyflavothiones, namely flavothione, 5-hydroxyflavothione, 5,7-dihydroxyflavothione (chrysinthione), 7-dodecyloxy-5-hydroxyflavothione, 7-butyloxy-5-hydroxyflavothione, 2′,3,4′,7-tetramethoxy-5- hydroxyflavothione, 3,3′,4′,7-tetramethoxy-5-hydroxyflavothione, 7-butyloxy-4′,5-dihydroxyflavothione and 7-butyloxy-4′,5- hydroxyflavanonethione have been synthesized from the corresponding hydroxyflavones in two steps, alkylation of the non-hydrogen-bonded hydroxyl groups by bromoalkanes or dimethyl sulfate followedby conversion of the carbonyl group to a thione using Lawesson's Reagent undermicrowave irradiation and solvent-free conditions. Part of the alkylated flavanone, 7-butyloxy-4′,5- dihydroxyflavanone, was oxidized during the treatment with Lawesson's reagent to yield a second product 7-butyloxy-4′,5-dihydroxyflavothione in addition to the target product butyloxy-4′,5-hydroxyflavanonethione. Deuterium isotope effects on 13C chemical shifts have been measured in hydroxyflavones, isoflavones, flavanones and the thio analogs. Formal four-bond deuterium isotope effects on 13C chemical shifts, nΔC= S(OD) are very sensitive to variations in structures and substitution patterns. Density functional theory (DFT) calculations are carried out to obtain geometries. Correlations relating distances around the hydrogen bond system to the deuterium isotope effects on 13C chemical shifts are discussed. 13C chemical shifts are calculated by DFT methods. Effects of thiocarbonyl anisotropies are suggested.

Synthesis of 5-Hydroxy-3,7,8,2',4'-pentamethoxyflavone

The title flavone (II) has been synthesised starting from 2'-hydroxy-2,4,4',6'-tetramethoxychalkone (VII).VII on treatment with H2O2 in the presence of alkali gives 3-hydroxy-5,7,2',4'-tetramethoxyflavone (III), which on methylation affords 3,5,7,2',4'-pe