Synthesis and evaluation of antioxidant activities of novel hydroxyalkyl esters and bis-aryl esters based on sinapic and caffeic acids
Novel hydroxyalkyl esters and bis-aryl esters were synthesized from sinapic and caffeic acids and aliphatic α,ω-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.
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Language: | eng |
Subjects: | Q04 - Composition des produits alimentaires, Q05 - Additifs alimentaires, acide sinapique, acide caféique, propriété physicochimique, antioxydant, radical libre, estérification, http://aims.fao.org/aos/agrovoc/c_36535, http://aims.fao.org/aos/agrovoc/c_36534, http://aims.fao.org/aos/agrovoc/c_1521, http://aims.fao.org/aos/agrovoc/c_511, http://aims.fao.org/aos/agrovoc/c_33488, http://aims.fao.org/aos/agrovoc/c_28361, |
Online Access: | http://agritrop.cirad.fr/596429/ http://agritrop.cirad.fr/596429/1/Laguna%20et%20al%20JAFC%202020.pdf |
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dig-cirad-fr-5964292024-01-29T03:00:14Z http://agritrop.cirad.fr/596429/ http://agritrop.cirad.fr/596429/ Synthesis and evaluation of antioxidant activities of novel hydroxyalkyl esters and bis-aryl esters based on sinapic and caffeic acids. Laguna Oscar, Durand Erwann, Baréa Bruno, Dauguet Sylvie, Fine Frédéric, Villeneuve Pierre, Lecomte Jérôme. 2020. Journal of Agricultural and Food Chemistry, 68 (35) : 9308-9318.https://doi.org/10.1021/acs.jafc.0c03711 <https://doi.org/10.1021/acs.jafc.0c03711> Synthesis and evaluation of antioxidant activities of novel hydroxyalkyl esters and bis-aryl esters based on sinapic and caffeic acids Laguna, Oscar Durand, Erwann Baréa, Bruno Dauguet, Sylvie Fine, Frédéric Villeneuve, Pierre Lecomte, Jérôme eng 2020 Journal of Agricultural and Food Chemistry Q04 - Composition des produits alimentaires Q05 - Additifs alimentaires acide sinapique acide caféique propriété physicochimique antioxydant radical libre estérification http://aims.fao.org/aos/agrovoc/c_36535 http://aims.fao.org/aos/agrovoc/c_36534 http://aims.fao.org/aos/agrovoc/c_1521 http://aims.fao.org/aos/agrovoc/c_511 http://aims.fao.org/aos/agrovoc/c_33488 http://aims.fao.org/aos/agrovoc/c_28361 Novel hydroxyalkyl esters and bis-aryl esters were synthesized from sinapic and caffeic acids and aliphatic α,ω-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. article info:eu-repo/semantics/article Journal Article info:eu-repo/semantics/publishedVersion http://agritrop.cirad.fr/596429/1/Laguna%20et%20al%20JAFC%202020.pdf text Cirad license info:eu-repo/semantics/restrictedAccess https://agritrop.cirad.fr/mention_legale.html https://doi.org/10.1021/acs.jafc.0c03711 10.1021/acs.jafc.0c03711 info:eu-repo/semantics/altIdentifier/doi/10.1021/acs.jafc.0c03711 info:eu-repo/semantics/altIdentifier/purl/https://doi.org/10.1021/acs.jafc.0c03711 |
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Q04 - Composition des produits alimentaires Q05 - Additifs alimentaires acide sinapique acide caféique propriété physicochimique antioxydant radical libre estérification http://aims.fao.org/aos/agrovoc/c_36535 http://aims.fao.org/aos/agrovoc/c_36534 http://aims.fao.org/aos/agrovoc/c_1521 http://aims.fao.org/aos/agrovoc/c_511 http://aims.fao.org/aos/agrovoc/c_33488 http://aims.fao.org/aos/agrovoc/c_28361 Q04 - Composition des produits alimentaires Q05 - Additifs alimentaires acide sinapique acide caféique propriété physicochimique antioxydant radical libre estérification http://aims.fao.org/aos/agrovoc/c_36535 http://aims.fao.org/aos/agrovoc/c_36534 http://aims.fao.org/aos/agrovoc/c_1521 http://aims.fao.org/aos/agrovoc/c_511 http://aims.fao.org/aos/agrovoc/c_33488 http://aims.fao.org/aos/agrovoc/c_28361 |
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Q04 - Composition des produits alimentaires Q05 - Additifs alimentaires acide sinapique acide caféique propriété physicochimique antioxydant radical libre estérification http://aims.fao.org/aos/agrovoc/c_36535 http://aims.fao.org/aos/agrovoc/c_36534 http://aims.fao.org/aos/agrovoc/c_1521 http://aims.fao.org/aos/agrovoc/c_511 http://aims.fao.org/aos/agrovoc/c_33488 http://aims.fao.org/aos/agrovoc/c_28361 Q04 - Composition des produits alimentaires Q05 - Additifs alimentaires acide sinapique acide caféique propriété physicochimique antioxydant radical libre estérification http://aims.fao.org/aos/agrovoc/c_36535 http://aims.fao.org/aos/agrovoc/c_36534 http://aims.fao.org/aos/agrovoc/c_1521 http://aims.fao.org/aos/agrovoc/c_511 http://aims.fao.org/aos/agrovoc/c_33488 http://aims.fao.org/aos/agrovoc/c_28361 Laguna, Oscar Durand, Erwann Baréa, Bruno Dauguet, Sylvie Fine, Frédéric Villeneuve, Pierre Lecomte, Jérôme Synthesis and evaluation of antioxidant activities of novel hydroxyalkyl esters and bis-aryl esters based on sinapic and caffeic acids |
description |
Novel hydroxyalkyl esters and bis-aryl esters were synthesized from sinapic and caffeic acids and aliphatic α,ω-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. |
format |
article |
topic_facet |
Q04 - Composition des produits alimentaires Q05 - Additifs alimentaires acide sinapique acide caféique propriété physicochimique antioxydant radical libre estérification http://aims.fao.org/aos/agrovoc/c_36535 http://aims.fao.org/aos/agrovoc/c_36534 http://aims.fao.org/aos/agrovoc/c_1521 http://aims.fao.org/aos/agrovoc/c_511 http://aims.fao.org/aos/agrovoc/c_33488 http://aims.fao.org/aos/agrovoc/c_28361 |
author |
Laguna, Oscar Durand, Erwann Baréa, Bruno Dauguet, Sylvie Fine, Frédéric Villeneuve, Pierre Lecomte, Jérôme |
author_facet |
Laguna, Oscar Durand, Erwann Baréa, Bruno Dauguet, Sylvie Fine, Frédéric Villeneuve, Pierre Lecomte, Jérôme |
author_sort |
Laguna, Oscar |
title |
Synthesis and evaluation of antioxidant activities of novel hydroxyalkyl esters and bis-aryl esters based on sinapic and caffeic acids |
title_short |
Synthesis and evaluation of antioxidant activities of novel hydroxyalkyl esters and bis-aryl esters based on sinapic and caffeic acids |
title_full |
Synthesis and evaluation of antioxidant activities of novel hydroxyalkyl esters and bis-aryl esters based on sinapic and caffeic acids |
title_fullStr |
Synthesis and evaluation of antioxidant activities of novel hydroxyalkyl esters and bis-aryl esters based on sinapic and caffeic acids |
title_full_unstemmed |
Synthesis and evaluation of antioxidant activities of novel hydroxyalkyl esters and bis-aryl esters based on sinapic and caffeic acids |
title_sort |
synthesis and evaluation of antioxidant activities of novel hydroxyalkyl esters and bis-aryl esters based on sinapic and caffeic acids |
url |
http://agritrop.cirad.fr/596429/ http://agritrop.cirad.fr/596429/1/Laguna%20et%20al%20JAFC%202020.pdf |
work_keys_str_mv |
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