121245-87-2

Basic information

• Product Name: 1-(2-HYDROXY-4,6-DIMETHOXYPHENYL)-3-(3-HYDROXY-4-METHOXYPHENYL)-2-PROPEN-1-ONE
• Synonyms: 1-(2-HYDROXY-4,6-DIMETHOXYPHENYL)-3-(3-HYDROXY-4-METHOXYPHENYL)-2-PROPEN-1-ONE;3,2'-DIHYDROXY-4,4',6'-TRIMETHOXYCHALCONE
• CAS NO: 121245-87-2
• Molecular Formula: C₁₈H₁₈O₆
• Molecular Weight: 330.33
• Mol File: 121245-87-2.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(2-HYDROXY-4,6-DIMETHOXYPHENYL)-3-(3-HYDROXY-4-METHOXYPHENYL)-2-PROPEN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-HYDROXY-4,6-DIMETHOXYPHENYL)-3-(3-HYDROXY-4-METHOXYPHENYL)-2-PROPEN-1-ONE(121245-87-2)
• EPA Substance Registry System: 1-(2-HYDROXY-4,6-DIMETHOXYPHENYL)-3-(3-HYDROXY-4-METHOXYPHENYL)-2-PROPEN-1-ONE(121245-87-2)

Safety Data

• Hazardous Substances Data: 121245-87-2(Hazardous Substances Data)

Upstream product

• 621-59-0 isovanillin 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 108-73-6 3,5-dihydroxyphenol 

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.