76650-20-9

Basic information

• Product Name: (2E)-3-(3,4-dimethoxyphenyl)-1-(2,4,6-trimethoxyphenyl)prop-2-en-1-one
• CAS NO: 76650-20-9
• Molecular Formula: C₂₀H₂₂O₆
• Molecular Weight: 358.3851
• Mol File: 76650-20-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 538.8°C at 760 mmHg
• Flash Point: 236.1°C
• Density: 1.156g/cm³
• Vapor Pressure: 1.12E-11mmHg at 25°C
• Refractive Index: 1.562
• CAS DataBase Reference: (2E)-3-(3,4-dimethoxyphenyl)-1-(2,4,6-trimethoxyphenyl)prop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-3-(3,4-dimethoxyphenyl)-1-(2,4,6-trimethoxyphenyl)prop-2-en-1-one(76650-20-9)
• EPA Substance Registry System: (2E)-3-(3,4-dimethoxyphenyl)-1-(2,4,6-trimethoxyphenyl)prop-2-en-1-one(76650-20-9)

Safety Data

• Hazardous Substances Data: 76650-20-9(Hazardous Substances Data)

Usage

General Description

The chemical compound "(2E)-3-(3,4-dimethoxyphenyl)-1-(2,4,6-trimethoxyphenyl)prop-2-en-1-one" is a type of chalcone, which is a class of organic compounds belonging to the flavonoids group. Chalcones are widely known for their diverse pharmacological properties, including anti-inflammatory, antioxidant, anticancer, and antimicrobial effects. The specific compound mentioned contains two methoxy groups on the 3,4-dimethoxyphenyl ring and three methoxy groups on the 2,4,6-trimethoxyphenyl ring. Its chemical structure suggests potential biological activities and possible applications in drug development and medicinal chemistry.

Upstream product

• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 832-58-6 1-(2,4,6-trimethoxyphenyl)ethanone 
• 67-56-1 methanol 
• 10496-67-0 3-(3,4-dimethoxyphenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one 
• 77-78-1 dimethyl sulfate 
• 108-73-6 3,5-dihydroxyphenol 
• 861015-19-2 1,3,5-tris-methoxycarbonyloxy-benzene 
• 139-85-5 3,4-dihydroxybenzaldehyde 

Downstream Products

• 17060-22-9 1-(3,4-dimethoxyphenyl)-3-(2,4,6-trimethoxyphenyl)propane 
• 114021-60-2 2'-hydroxy-3,4,4',6'-tetramethoxychalcone 
• 10496-67-0 3-(3,4-dimethoxyphenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one 
• 1178-24-1 3,3',4',5,6,7,8-heptamethoxyflavone 
• 35154-55-3 3-hydroxy-5,6,7,8,3′,4′-hexamethoxyflavone 
• 478-01-3 nobiletin 
• 7741-47-1 hexa-O-methylogossypetin 
• 17290-70-9 isosinensetin 
• 1247-97-8 pentamethyl quercetin 
• 1245-15-4 retusin 
• 1244-78-6 2-(3,4-dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-4H-4-chromenone 
• 2306-27-6 sinensetin 
• 71847-58-0 5,8-dihydroxy-7-methoxy-2-(3,4-dimethoxyphenyl)-4-benzopyrone 
• 855-97-0 2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one 

Relevant articles and documents

Identification of methoxylchalcones produced in response to CuCl2 treatment and pathogen infection in barley

Changes in specialized metabolites were analyzed in barley (Hordeum vulgare) leaves treated with CuCl2 solution as an elicitor. LC-MS analysis of the CuCl2-treated leaves showed the induced accumulation of three compounds. Among them

Synthesis of xanthohumol analogues and discovery of potent thioredoxin reductase inhibitor as potential anticancer agent

The selenoprotein thioredoxin reductases (TrxRs) are attractive targets for anticancer drugs development. Xanthohumol (Xn), a naturally occurring polyphenol chalcone from hops, has received increasing attention because of its multiple pharmacological activities. We synthesized Xn and its 43 analogues and discovered that compound 13n displayed the highest cytotoxicity toward HeLa cells (IC50 = 1.4 μM). Structure-activity relationship study indicates that the prenyl group is not necessary for cytotoxicity, and introducing electron-withdrawing group, especially on the meta-position, is favored. In addition, methylation of the phenoxyl groups generally improves the potency. Mechanistic study revealed that 13n selectively inhibits TrxR and induces reactive oxygen species and apoptosis in HeLa cells. Cells overexpressing TrxR are resistant to 13n insult, while knockdown of TrxR sensitizes cells to 13n treatment, highlighting the physiological significance of targeting TrxR by 13n. The clarification of the structural determinants for the potency would guide the design of novel potent molecules for future development.

Dye-sensitized Photoconversion of Chalkones into Aurones

Dye-sensitized photooxygenation of 2'-hydroxy-4',6',3,4-tetramethoxychalkone yields 4,6,3',4'-tetramethoxyaurone.It is the first report of photochemical conversion of chalkones into aurones.Besides this, methylation of chelated hydroxyl is also being reported for the first time from this reaction.