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Advisor(s)
Abstract(s)
Long chain alkyl hydroxycinnamates (8e21) were synthesized from the corresponding half esters of
malonic acid (5e7) and benzaldehyde derivatives by Knoevenagel condensation. The total antioxidant
capacity of these hydroxycinnamyl esters was evaluated using DPPH and ABTS assays. The observed
antioxidant activity was highest for esters of caffeic acid followed by sinapic esters and ferulic esters. The
parameters for drug-likeness of these hydroxycinnamyl esters were also evaluated according to the
Lipinski’s ‘rule-of-five’. All the ester derivatives were found to violate one of the Lipinski’s parameters
(cLogP >5), even though they have been found to be soluble in protic solvents. The predictive topological
polar surface area (TPSA) data allow concluding that they could have a good capacity for penetrating cell
membranes. Therefore, one can propose these novel lipophilic compounds as potential antioxidants for
tackling oxidative processes.
Description
Keywords
Alkyl hydroxycinnamates Antioxidant activity Caffeic acid Ferulic acid Sinapic acid Drug-likeness properties
Citation
Publisher
Elsevier