Synthesis of 4’,5,7-trihydroxyflavanone and 3’,4’,5,7-tetrahydroxyflavanone and antioxidant activity

• Main Authors: Ahmad, Farediah, Mohamed Adib, Adiana, Idris , Muhamad Sum
• Format: Article
• Language: English; English
• Published: ibnu Sina Institute for Fundamental Science Studies, Universiti Teknologi Malaysia 2010
• Subjects: Q Science (General)
• Online Access: http://eprints.utm.my/id/eprint/25999/3/FarediahAhmad2010_Synthesisof4%E2%80%99%2C5%2C7-trihydroxyflavanoneand3%E2%80%99%2C4%E2%80%99%2C5%2C7-tetrahydroxyflavanone.pdf; http://eprints.utm.my/id/eprint/25999/2/83; http://eprints.utm.my/id/eprint/25999/; http://mjfas.ibnusina.utm.my/index.php/jfs/article/view/146; http://mjfas.ibnusina.utm.my/index.php/jfs/article/view/146/83

Natural flavonoid, namely 4’,5,7-trihydroxyflavanone and 3’,4’,5,7-tetrahydroxyflavanone were synthesised via its chalcone. The initial step was to synthesize derivatives of 2-hydroxyacetophenone and benzaldehyde by protecting the phenolic hydroxyl groups. The respective chalcone was synthesised by Claisen-Schmidt condensation. 4’,5,7-Trihydroxyflavanone and 3’,4’,5,7-tetrahydroxyflavanone were synthesised by acid hydrolysis and subsequent treatment with sodium acetate of the respective chalcones, 2’-hydroxy-4,4’-6’-tris(methoxymethyloxy)chalcone and 2’-hydroxy-3,4,4’,6’-tetrakis(methoxymethyloxy)chalcone. 3’,4’,5,7-Tetrahydroxyflavanone was found to be more potent as an antioxidant agent than 4’,5,7-trihydroxyflavanone with 83.11% inhibition and IC50 8.57 ?g/mL in the radical scavenging activity by ESR method.