4315-88-2

Basic information

• Product Name: (2E)-1-(2,4-dihydroxyphenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one
• CAS NO: 4315-88-2
• Molecular Formula: C₁₇H₁₆O₅
• Molecular Weight: 300.3059
• Mol File: 4315-88-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 517.6°C at 760 mmHg
• Flash Point: 191.6°C
• Density: 1.279g/cm³
• Vapor Pressure: 2.47E-11mmHg at 25°C
• Refractive Index: 1.636
• CAS DataBase Reference: (2E)-1-(2,4-dihydroxyphenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-1-(2,4-dihydroxyphenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one(4315-88-2)
• EPA Substance Registry System: (2E)-1-(2,4-dihydroxyphenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one(4315-88-2)

Safety Data

• Hazardous Substances Data: 4315-88-2(Hazardous Substances Data)

Usage

Description

(2E)-1-(2,4-dihydroxyphenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one is a chalcone, a type of natural phenol, with a propenone backbone and two aromatic rings, one with two hydroxyl groups and the other with two methoxy groups. This organic compound has a complex molecular structure and has been studied for its potential biological activities, such as antioxidant, anti-inflammatory, and anti-cancer properties.

Uses

Used in Pharmaceutical Industry:
(2E)-1-(2,4-dihydroxyphenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one is used as a potential pharmaceutical candidate for its potential pharmacological effects due to its antioxidant, anti-inflammatory, and anti-cancer properties.
Used in Drug Development:
(2E)-1-(2,4-dihydroxyphenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one is used in drug development for further research into its potential biological activities and pharmacological effects, given its unique chemical structure and classification as a chalcone.

Upstream product

• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 1417453-14-5 2’,4’-diisopropoxy-3,4-dimethoxychalcone 
• 728911-59-9 2,4-diisopropoxyacetophenone 
• 2079-52-9 1-(2,4-bis(allyloxy)phenyl)ethanone 
• 65490-08-6 2-hydroxy-4-(methoxymethoxy)acetophenone 

Downstream Products

• 128995-99-3 1-(2,4-dihydroxyphenyl)-3-(3,4-dimethoxyphenyl)propane-1-one 
• 743442-96-8 3-(3,4-dimethoxyphenyl)-1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)propan-1-one 
• 32396-83-1 2-(3,4-dimethoxybenzylidene)-6-hydroxybenzofuran-3(2H)-one 

Relevant articles and documents

Flavonoid glycosides with a triazole moiety for marine antifouling applications: Synthesis and biological activity evaluation

Over the last decades, antifouling coatings containing biocidal compounds as active ingre-dients were used to prevent biofouling, and eco-friendly alternatives are needed. Previous research from our group showed that polymethoxylated chalcones and glycosy

Reactivity assessment of chalcones by a kinetic thiol assay

The electrophilic nature of chalcones (1,3-diphenylprop-2-en-1-ones) and many other α,β-unsaturated carbonyl compounds is crucial for their biological activity, which is often based on thiol-mediated regulation processes. To better predict their biological activity a simple screening assay for the assessment of the second-order rate constants (k2) in thia-Michael additions was developed. Hence, a clear structure-activity relationship of 16 differentially decorated hydroxy-alkoxychalcones upon addition of cysteamine could be established. Moreover, amongst other naturally occurring α,β-unsaturated carbonyl compounds k2 values for curcumin and cinnamaldehyde were gained while cinnamic acids or esters gave no or very slow reactions.

Synthesis and insight into the structure-activity relationships of chalcones as antimalarial agents

Licochalcone A (I), isolated from the roots of Chinese licorice, is the most promising antimalarial compound reported so far. In continuation of our drug discovery program, we isolated two similar chalcones, medicagenin (II) and munchiwarin (III), from Crotalaria medicagenia, which exhibited antimalarial activity against Plasmodium falciparum. A library of 88 chalcones were synthesized and evaluated for their in vitro antimalarial activity. Among these, 67, 68, 74, 77, and 78 exhibited good in vitro antimalarial activity against P. falciparum strains 3D7 and K1 with low cytotoxicity. These chalcones also showed reduction in parasitemia and increased survival time of Swiss mice infected with Plasmodium yoelii (strain N-67). Pharmacokinetic studies indicated that low oral bioavailability due to poor ADME properties. Molecular docking studies revealed the binding orientation of these inhibitors in active sites of falcipain-2 (FP-2) enzyme. Compounds 67, 68, and 78 showed modest inhibitory activity against the major hemoglobin degrading cysteine protease FP-2.