64200-22-2

Basic information

• Product Name: 2'-HYDROXY-2,4,4',6'-TETRAMETHOXYCHALCONE
• Synonyms: 2'-HYDROXY-2,4,4',6'-TETRAMETHOXYCHALCONE;Cerasidin;(2E)-3-(2,4-Dimethoxyphenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)-2-propen-1-one;2,4-Dimethoxyflavokawain B
• CAS NO: 64200-22-2
• Molecular Formula: C₁₉H₂₀O₆
• Molecular Weight: 344.36
• Mol File: 64200-22-2.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2'-HYDROXY-2,4,4',6'-TETRAMETHOXYCHALCONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-HYDROXY-2,4,4',6'-TETRAMETHOXYCHALCONE(64200-22-2)
• EPA Substance Registry System: 2'-HYDROXY-2,4,4',6'-TETRAMETHOXYCHALCONE(64200-22-2)

Safety Data

• Hazardous Substances Data: 64200-22-2(Hazardous Substances Data)

Usage

Description

2'-Hydroxy-2,4,4',6'-tetramethoxychalcone is a chalcone compound characterized by the presence of an aromatic ketone and enone structure. It possesses a unique chemical structure with hydroxy and methoxy groups, which contribute to its biological properties and potential applications.

Uses

Used in Pharmaceutical Industry:
2'-Hydroxy-2,4,4',6'-tetramethoxychalcone is used as a cytotoxic agent for its potential anticancer properties. It has been studied for its ability to inhibit the growth and proliferation of cancer cells, making it a promising candidate for further research and development in cancer therapy.
Used in Neuropharmacology Research:
2'-Hydroxy-2,4,4',6'-tetramethoxychalcone is used as a positive allosteric modulator for α7 acetylcholine nicotine receptors. Its chalcone structure allows it to interact with these receptors, potentially enhancing their function and providing therapeutic benefits in neurological disorders and cognitive enhancement.

Upstream product

• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 613-45-6 2,4-Dimethoxybenzaldehyde 
• 108-73-6 3,5-dihydroxyphenol 
• 480-66-0 2,4,6-trihydroxyacetophenone 

Downstream Products

• 84757-50-6 2-(2,4-dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-4H-chromen-4-one 
• 109688-40-6 2-(2,4-dimethoxy-benzylidene)-4,6-dimethoxy-benzofuran-3-one 
• 110048-36-7 2-(2,4-dimethoxy-phenyl)-5,7-dimethoxy-chroman-4-one 
• 71787-04-7 5-hydroxy-3,7,8,2',4'-pentamethoxyflavone 
• 19056-75-8 2-(2,4-dimethoxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-chromen-4-one 
• 7555-80-8 pentamethyl morin 
• 84757-51-7 2-(2,4-Dimethoxy-phenyl)-5,8-dihydroxy-3,7-dimethoxy-chromen-4-one 
• 1335008-89-3 (E)-1-(3-bromo-2-hydroxyl-4,6-dimethoxyphenyl)-3-(2,4-dimethoxyphenyl)prop-2-en-1-one 

Relevant articles and documents

Development of a novel nitric oxide (NO) production inhibitor with potential therapeutic effect on chronic inflammation

Inflammation is a complex biological response to stimuli. Activated macrophages induced excessively release of pro-inflammatory cytokines and mediators such as endogenous radical nitric oxide (NO) play a significant role in the progression of multiple inflammatory diseases. Both natural and synthetic chalcones possess a wide range of bioactivities. In this work, thirty-nine chalcones and three related compounds, including several novel ones, based on bioactive kava chalcones were designed, synthesized and their inhibitory effects on NO production in RAW 264.7 cells were evaluated. The novel compound (E)-1-(2′-hydroxy-4′,6′-dimethoxyphenyl)-3-(3-methoxy-4-(3-morpholinopropoxy)phenyl)prop-2-en-1-one (53) exhibited a better inhibitory activity (84.0%) on NO production at 10 μM (IC50 = 6.4 μM) with the lowest cytotoxicity (IC50 > 80 μM) among the tested compounds. Besides, western blot analysis indicated that compound 53 was a potent down-regulator of inducible nitric oxide synthase (iNOS) protein. Docking study revealed that compound 53 also can dock into the active site of iNOS. Furthermore, at the dose of 10 mg/kg/day, compound 53 could both significantly suppress the progression of inflammation on collagen-induced arthritis (CIA) and adjuvant-induced arthritis (AIA) models. In addition, the structure-activity relationship (SAR) of the kava chalcones based analogs was also depicted.

13C Nuclear Magnetic Resonance Studies on 1,3-Diphenylprop-2-enones

The 13C NMR spectra of 48 differently substituted chalcones (1,3-diphenylprop-2-enones) have been recorded and the results are discussed.The data will be useful in the identification of new/natural chalcones.

Substituted acetophenones and compositions containing them

Antivirally active compounds of the formula STR1 wherein R1 represents hydroxy, acyloxy derived from an aliphatic acid having 2-18 carbon atoms or a heterocyclic carboxylic acid containing nitrogen atom(s), lower alkoxycarbonyloxy, aminoacyloxy or carboxyalkanoyloxy; R2 represents lower alkoxy; R3 represents hydrogen or lower alkoxy; and R4 represents phenyl which may be substituted by one or more substituents selected from the group consisting of lower alkyl, lower alkoxy, benzyloxy, allyloxy, alkylthio, dialkylamino, amino, cyano, hydroxy, halo and alkylenedioxy; or pyridyl, furyl, thienyl or pyrrolyl which may be substituted by lower alkyl, pharmaceutical compositions containing them and a process for the preparation of those compounds of formula I which are novel.