Synthesis of 4’,5,7-trihydroxyflavanone and 3’,4’,5,7-tetrahydroxyflavanone and antioxidant activity
DOI:
https://doi.org/10.11113/mjfas.v6n1.168Keywords:
4’, 5, 7-Trihydroxyflavanone, 3’, 7-Tetrahydroxyflavanone, Chalcones, Antioxidant, ESR,Abstract
Natural flavonoids, 4’,5,7-trihydroxyflavanone and 3’,4’,5,7-tetrahydroxyflavanone were synthesised via their respective chalcone. The initial step was
to synthesise derivatives of 2-hydroxyacetophenone and benzaldehyde by protecting the phenolic hydroxyl groups. The chalcone was synthesised by
Claisen-Schmidt condensation. Acid hydrolysis and subsequent treatment with sodium acetate of 2’-hydroxy-4,4’-6’-tris(methoxymethyloxy)chalcone
and 2’-hydroxy-3,4,4’,6’-tetrakis(methoxymethyloxy)chalcone, gave 4’,5,7-trihydroxyflavanone and 3’,4’,5,7-tetrahydroxyflavanone, respectively.
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 SC50
8.57 μg/mL in the radical scavenging activity by ESR method.
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