13351-10-5

Basic information

• Product Name: 2',4-DIHYDROXY-4'-METHOXYCHALCONE
• Synonyms: 2',4-DIHYDROXY-4'-METHOXYCHALCONE;ISOLIQUIRITIGENIN-4'-METHYL ETHER;(2E)-1-(2,4-dihydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one
• CAS NO: 13351-10-5
• Molecular Formula: C₁₆H₁₄O₄
• Molecular Weight: 270.28
• Product Categories: Miscellaneous Natural Products
• Mol File: 13351-10-5.mol
• Article Data: 35

Chemical Properties

• Melting Point: 186 °C
• Boiling Point: 499.4°C at 760 mmHg
• Flash Point: 189°C
• Appearance: /
• Density: 1.282g/cm³
• Vapor Pressure: 1.35E-10mmHg at 25°C
• Refractive Index: 1.657
• PKA: 7.36±0.35(Predicted)
• CAS DataBase Reference: 2',4-DIHYDROXY-4'-METHOXYCHALCONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2',4-DIHYDROXY-4'-METHOXYCHALCONE(13351-10-5)
• EPA Substance Registry System: 2',4-DIHYDROXY-4'-METHOXYCHALCONE(13351-10-5)

Safety Data

• Hazard Codes: Xn,N
• Statements: 50
• Safety Statements: 61
• WGK Germany: 3
• Hazardous Substances Data: 13351-10-5(Hazardous Substances Data)

Usage

General Description

2',4-Dihydroxy-4'-methoxychalcone is a naturally occurring chemical compound belonging to the chalcone class of flavonoids. It is found in various plant sources and is known for its antioxidant and anti-inflammatory properties. The compound has been studied for its potential pharmacological activities, including its role in preventing oxidative stress and promoting overall cellular health. 2',4-Dihydroxy-4'-methoxychalcone has also been investigated for its potential use in the development of new therapeutic agents for various diseases, including cancer, diabetes, and cardiovascular disorders. Additionally, it has been found to have potential applications in the skincare and cosmetic industries.

InChI:InChI=1/C16H14O4/c1-20-13-6-2-11(3-7-13)4-9-15(18)14-8-5-12(17)10-16(14)19/h2-10,17,19H,1H3/b9-4+

Upstream product

• 102553-93-5 C₂₀H₂₂O₆ 
• 123-11-5 4-methoxy-benzaldehyde 
• 136258-01-0 2',4'-bis(tetrahydropyran-2-yloxy)acetophenone 
• 3557-22-0 1-(2-hydroxy-5-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)ethan-1-one 
• 490-78-8 2,5-Dihydroxyacetophenone 
• 20034-62-2 2'-Hydroxy-4'-(aethoxy-methoxy)-acetophenon 
• 114107-22-1 4-methoxy-2',4'-dimethoxymethyl-(E)-chalcone 
• 6515-05-5 2',4'-bis(methoxymethoxy)acetophenone 
• 111841-07-7 2-hydroxy-4-(tetrahydropyran-2-yloxy)acetophenone 
• 65490-08-6 2-hydroxy-4-(methoxymethoxy)acetophenone 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 81674-92-2 (E)-1-(4-(benzyloxy)-2-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one 
• 154407-02-0 (E)-1-(2-hydroxy-4-(tetrahydro-2H-pyran-2-yloxy)phenyl)-3-(4-methoxyphenyl)prop-2-en-1-one 
• 109471-14-9 (2E)-1-[2-hydroxy-4-(methoxymethoxy)phenyl]-3-(4-methoxyphenyl)prop-2-en-1-one 

Downstream Products

• 487-24-1 pratol 
• 255831-59-5 crotaramin 
• 93435-21-3 1-(2,4-dihydroxyphenyl)-3-(4-methoxyphenyl)propane-1-one 
• 67005-90-7 2'-acetoxy-4-methoxy-4'-(tetra-O-acetyl-β-D-glucopyranosyloxy)-trans-chalcone 
• 552-26-1 3,7-dihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one 
• 108837-20-3 7-hydroxy-2-(4'-methoxyphenyl)chroman-4-one 
• 30925-62-3 metochalcone 

Relevant articles and documents

Antioxidant and Cardioprotective Evaluation of Some N-(3-Chloro-2-oxo-4-arylazetidin-1-yl)-2-[(4-oxo-2-aryl-4H-chromen-7-yl)oxy]acetamide Derivatives

A series of N-(3-chloro-2-oxo-4-arylazetidin-1-yl)-2-[(4-oxo-2-aryl-4H-chromen-7-yl)oxy]acetamide derivatives [SLP VI 1(a-d)-2(a-d)] were synthesized from 7-hydroxy flavone derivatives through the intermediate Schiff bases. The synthesized compounds were investigated for in vitro antioxidant property by DPPH radical scavenging assay. The title compounds with good antioxidant potency were further evaluated for possible cardioprotective effect by doxorubicin induced cardiotoxicity. All biochemical changes were normalized after oral administration of the test compounds at the dose of 50 μg/kg. The results showed the significant (p 0.05) increase in antioxidant enzymes catalase and superoxide dismutase in heart tissue homogenates. These observations enable us to conclude that the synthesized derivatives SLP VI 1b, VI 1c, VI 2b and VI 2d have cardioprotective activity against doxorubicin induced cardiotoxicity. Further, an attempt has been made to perform in silico studies on the synthesized compounds to predict the interaction between test ligands and prospective cardiovascular protein targets using molecular docking tools. The title compounds have good binding affinity with MAPkinase P38 and PKCβ cardiovascular targets.

Chromone derivatives bearing pyridinium moiety as multi-target-directed ligands against Alzheimer's disease

A new serise of 7-hydroxy-chromone derivatives bearing pyridine moiety were synthesized, and evaluated as multifunctional agents against Alzheimer's disease (AD). Most of the compounds were good AChE inhibitors (IC50 = 9.8–0.71 μM) and showed remarkable BuChE inhibition activity (IC50 = 1.9–0.006 μM) compared with donepezil as the standard drug (IC50 = 0.023 and 3.4 μM). Compounds 14 and 10 showed the best inhibitory activity toward AChE (IC50 = 0.71 μM) and BuChE (IC50 = 0.006 μM), respectively. The ligand–protein docking simulations and kinetic studies revealed that compound 14 and 10 could bind effectively to the peripheral anionic binding site (PAS) of the AChE and BuChE through mixed-type inhibition. In addition, the most potent compounds showed acceptable neuroprotective activity on H2O2- and Aβ-induced.neurotoxicity in PC12 cells, more than standard drugs. The compounds could block effectively self- and AChE-induced Aβ aggregation. All the results suggest that compounds 14 and 10 could be considered as promising multi-target-directed ligands against AD.

Synthesis and biological evaluation of isoliquiritigenin derivatives as a neuroprotective agent against glutamate mediated neurotoxicity in HT22 cells

Glutamate-induced neurotoxicity is characterized by cellular Ca2+ uptake, which is upstream of reactive oxygen species (ROS)-induced apoptosis signaling and MAPKs activation. In the present study, we synthesized isoliquiritigenin analogs with electron-donating and electron-withdrawing functional groups. These analogs were evaluated for neuroprotective effect against glutamate-induced neurotoxicity in HT22 cells. Among these analogs, compound BS11 was selected as a potent neuroprotective agent. Cellular Ca2+ concentration, ROS level, MAPKs activation and AIF translocation to the nucleus were increased upon treatment with 5 mM glutamate. In contrast, we identified that compound BS11 reduced the cellular Ca2+ concentration and ROS level upon glutamate exposure. Western blot analysis showed that MAPK activation was decreased by treatment with compound BS11. We further identified that cotreatment of compound BS11 and glutamate inhibited translocation of AIF to the nucleus.