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Synthesis and evaluation of antioxidant activities of novel hydroxyalkyl esters and bis-aryl esters based on sinapic and caffeic acids

Laguna O., Durand E., Baréa B., Dauguet S., Fine F., Villeneuve P., Lecomte J.. 2020. Journal of Agricultural and Food Chemistry, 68 (35) : p. 9308-9318.

DOI: 10.1021/acs.jafc.0c03711

Novel hydroxyalkyl esters and bis-aryl esters were synthesized from sinapic and caffeic acids and aliphatic a,¿-diols of increasing chain lengths from 2 to 12 carbon atoms. Then, their antiradical reactivity (DPPH assay) and their antioxidant activity in a model oil-in-water emulsion (CAT assay) were evaluated. All the esters showed lower antiradical activities compared to their corresponding phenolic acid. This decrease was associated with the steric hindrance in hydroxyalkyl esters, and intramolecular interactions in bis-aryl esters. Regarding the two bis-aryl esters series in emulsion, the antioxidant capacity was improved with alkyl chain lengthening up to four carbons, after which it decreased for longer chains. This ¿cutoff¿ effect was not observed for both hydroxyalkyl esters series for which the alkyl chain lengthening results in a decrease of the antioxidant activity.

Mots-clés : acide sinapique; acide caféique; propriété physicochimique; antioxydant; radical libre; estérification

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