3327-24-0

Basic information

• Product Name: 2'-HYDROXY-4-METHOXYCHALCONE
• Synonyms: 2'-HYDROXY-4-METHOXYCHALCONE;1-(2-HYDROXYPHENYL)-3-(4-METHOXYPHENYL)PROP-2-EN-1-ONE;(1-(2-hydroxyphenyl)-3-(4-methoxyphenyl-2-propen-1-one);4-Methoxy-2'-hydroxychalcone;1-(2-hydroxyphenyl)-3-(4-methoxyphenyl)-2-propen-1-one (en)
• CAS NO: 3327-24-0
• Molecular Formula: C₁₆H₁₄O₃
• Molecular Weight: 254.28
• Product Categories: Chalcones
• Mol File: 3327-24-0.mol
• Article Data: 105

Chemical Properties

• Melting Point: 91-92°C
• Boiling Point: 444.8°Cat760mmHg
• Flash Point: 167.3°C
• Appearance: /
• Density: 1.197g/cm³
• Vapor Pressure: 1.59E-08mmHg at 25°C
• Refractive Index: 1.631
• Solubility: soluble in Methanol
• PKA: 7.71±0.30(Predicted)
• CAS DataBase Reference: 2'-HYDROXY-4-METHOXYCHALCONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-HYDROXY-4-METHOXYCHALCONE(3327-24-0)
• EPA Substance Registry System: 2'-HYDROXY-4-METHOXYCHALCONE(3327-24-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 3327-24-0(Hazardous Substances Data)

Usage

General Description

2'-Hydroxy-4-methoxychalcone is a chemical compound from the class of chalcones, naturally occurring aromatic ketones known for various biological activities. The compound can be found in a variety of botanical species and has been documented for its potential pharmacological properties. Its chemical formula is C16H14O3 and it includes functional groups like hydroxyl and methoxy groups attached to a chalcone backbone. Although specific details can vary, many chalcones like 2'-Hydroxy-4-methoxychalcone have been recognized for activities such as anti-inflammatory, antioxidant, anticancer, antimicrobial, and immunomodulatory properties. Its precise mechanism of action or all potential applications may not be fully understood and may require further research.

InChI:InChI=1/C16H14O3/c1-19-13-9-6-12(7-10-13)8-11-16(18)14-4-2-3-5-15(14)17/h2-11,17H,1H3

Upstream product

• 118-93-4 o-hydroxyacetophenone 
• 123-11-5 4-methoxy-benzaldehyde 
• 39729-17-4 2'-hydroxy-4-methoxychalcone dibromide 
• 154903-09-0 C₁₆H₁₃BF₂O₃ 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 42996-84-9 p-methoxycinnamoyl chloride 
• 108-95-2 phenol 

Downstream Products

• 4143-74-2 4'-methoxyflavone 
• 61495-70-3 3-(4-methoxyphenyl)-5-(2-hydroxyphenyl)-isoxazole 
• 43016-21-3 3-(2'-hydroxyphenyl)-5-(p-methoxyphenyl)isoxazole 
• 87544-61-4 (2-Hydroxy-phenyl)-[4-(4-methoxy-phenyl)-4,5-dihydro-1H-pyrazol-3-yl]-methanone 
• 125343-89-7 2'-phenylacetyloxy-4-methoxychalcone 
• 81819-85-4 1-phenyl-3-(o-hydroxyphenyl)-5-(p-methoxyphenyl)pyrazoline 
• 125966-83-8 <4-(2-hydroxyphenyl)-6-(4-methoxyphenyl)>pyrimidine-2-sulphonamido-N⁴-acetamide 
• 61495-71-4 3-Hydroxyamino-1-(2-hydroxy-phenyl)-3-(4-methoxy-phenyl)-propan-1-one oxime 
• 14166-14-4 4'-methoxy-3-iodoflavanone 
• 6953-32-8 2-(4-methoxyphenyl)chroman-4-one oxime 
• 61495-69-0 1-(2-hydroxyphenyl)-3-(4-methoxyphenyl)-2-propen-1-one oxime 
• 58721-63-4 2-[5-(4-methoxy-phenyl)-3,4-dihydro-2H-pyrazol-3-yl]-phenol 
• 3034-08-0 2-(4-methoxyphenyl)-2,3-dihydro-4H-chromen-4-one 
• 6889-78-7 4'-(methoxy)-3-hydroxyflavone 

Relevant articles and documents

Antioxidant flavone analog functionalized fluorescent silica nanoparticles: Synthesis and exploration of their possible use as biomolecule sensor

For the first time, a synthetic fluorescent antioxidant flavone analog was successfully anchored onto the surface of the APTES-modified mesoporous silica nanoparticles (NPs) through sulfonamide linkage. The surface chemistry and morphology of the flavone

A novel one-pot synthesis of flavones

In this paper, a one-pot facile route for the BiCl3/RuCl3-mediated synthesis of functionalized flavones is described, including: (i) intermolecularortho-acylation of substituted phenols with cinnamoyl chlorides, and (ii) intramolecular cyclodehydrogenation of the resultingo-hydroxychalcones. The reaction conditions are discussed herein.

Stereoselective reduction of flavanones by marine-derived fungi

Biotransformation is an alternative with great potential to modify the structures of natural and synthetic flavonoids. Therefore, the bioreduction of synthetic halogenated flavanones employing marine-derived fungi was described, aiming the synthesis of flavan-4-ols 3a-g with high enantiomeric excesses (ee) of both cis- and trans-diastereoisomers (up to >99% ee). Ten strains were screened for reduction of flavanone 2a in liquid medium and in phosphate buffer solution. The most selective strains Cladosporium sp. CBMAI 1237 and Acremonium sp. CBMAI1676 were employed for reduction of flavanones 2a-g. The fungus Cladosporium sp. CBMAI 1237 presented yields of 72–87% with 0–64% ee cis and 0–30% ee trans with diastereoisomeric ratio (dr) from 52:48 to 64:36 (cis:trans). Whereas Acremonium sp. CBMAI 1676 resulted in 31% yield with 77–99% ee of the cis and 95–99% ee of the trans-diastereoisomers 3a-g with a dr from 54:46 to 96:4 (cis:trans). To our knowledge, this is the first report of the brominated flavon-4-ols 3e and 3f. The use of fungi, with emphasis for these marine-derived strains, is an interesting approach for enantioselective reduction of halogenated flavanones. Therefore, this strategy can be explored to obtain enantioenriched compounds with biological activities.