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) wer...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2020-09, Vol.68 (35), p.9308-9318 |
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| container_issue | 35 |
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| container_title | Journal of agricultural and food chemistry |
| container_volume | 68 |
| creator | Laguna, Oscar Durand, Erwann Baréa, Bruno Dauguet, Sylvie Fine, Frédéric Villeneuve, Pierre Lecomte, Jérôme |
| 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. |
| doi_str_mv | 10.1021/acs.jafc.0c03711 |
| format | Article |
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Agric. Food Chem</addtitle><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.</description><subject>Agricultural and Environmental Chemistry</subject><subject>Antioxidants - chemical synthesis</subject><subject>Antioxidants - chemistry</subject><subject>Caffeic Acids - chemistry</subject><subject>Coumaric Acids - chemistry</subject><subject>Esters - chemistry</subject><subject>Food engineering</subject><subject>Life Sciences</subject><subject>Molecular Structure</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kUFv0zAUxy0EYt3gzgnlyKSlPDtx7ByzqlCkCg6Ds_Ua25pHGhc7qZYvwOfGXco4IVny0_Pv_aTnPyHvKCwpMPoR27h8QNsuoYVCUPqCLChnkHNK5UuygMTkklf0glzG-AAAkgt4TS4KJmQlWb0gv--mfrg30cUMe52tj9iNODjfZ95mTZ-qR6exH7KmHdzRDc7E08tXfzRdtpl08I8Tdj-nLlvHwYTZcuti3oR_vVuMRmfJeed6PLj2CVqhtSbVTet0fENeWeyieXu-r8iPT-vvq02-_fb5y6rZ5lgIGHJa74SumbUMGOc7ITlPi3BE4G1V8x0rNdqCsaoEI40wrCpKJrVkJU9HsuKKXM_ee-zUIbg9hkl5dGrTbNWpB6wuATgcaWI_zOwh-F-jiYPau9iarsPe-DEqVhYlcFEXIqEwo23wMQZjn90U1CkplZJSp6TUOak08v5sH3d7o58H_kaTgJsZeBr1Y-jTx_zf9we_053g</recordid><startdate>20200902</startdate><enddate>20200902</enddate><creator>Laguna, Oscar</creator><creator>Durand, Erwann</creator><creator>Baréa, Bruno</creator><creator>Dauguet, Sylvie</creator><creator>Fine, Frédéric</creator><creator>Villeneuve, Pierre</creator><creator>Lecomte, Jérôme</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0002-0306-8081</orcidid><orcidid>https://orcid.org/0000-0001-9942-5858</orcidid><orcidid>https://orcid.org/0000-0003-1685-1494</orcidid></search><sort><creationdate>20200902</creationdate><title>Synthesis and Evaluation of Antioxidant Activities of Novel Hydroxyalkyl Esters and Bis-Aryl Esters Based on Sinapic and Caffeic Acids</title><author>Laguna, Oscar ; Durand, Erwann ; Baréa, Bruno ; Dauguet, Sylvie ; Fine, Frédéric ; Villeneuve, Pierre ; Lecomte, Jérôme</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a370t-19b7d92ff20255b78557865aa05c695b24daf322640e8e7e263428d8245245823</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Agricultural and Environmental Chemistry</topic><topic>Antioxidants - chemical synthesis</topic><topic>Antioxidants - chemistry</topic><topic>Caffeic Acids - chemistry</topic><topic>Coumaric Acids - chemistry</topic><topic>Esters - chemistry</topic><topic>Food engineering</topic><topic>Life Sciences</topic><topic>Molecular Structure</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Laguna, Oscar</creatorcontrib><creatorcontrib>Durand, Erwann</creatorcontrib><creatorcontrib>Baréa, Bruno</creatorcontrib><creatorcontrib>Dauguet, Sylvie</creatorcontrib><creatorcontrib>Fine, Frédéric</creatorcontrib><creatorcontrib>Villeneuve, Pierre</creatorcontrib><creatorcontrib>Lecomte, Jérôme</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Laguna, Oscar</au><au>Durand, Erwann</au><au>Baréa, Bruno</au><au>Dauguet, Sylvie</au><au>Fine, Frédéric</au><au>Villeneuve, Pierre</au><au>Lecomte, Jérôme</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Evaluation of Antioxidant Activities of Novel Hydroxyalkyl Esters and Bis-Aryl Esters Based on Sinapic and Caffeic Acids</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2020-09-02</date><risdate>2020</risdate><volume>68</volume><issue>35</issue><spage>9308</spage><epage>9318</epage><pages>9308-9318</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><abstract>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. 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| ispartof | Journal of agricultural and food chemistry, 2020-09, Vol.68 (35), p.9308-9318 |
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| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Agricultural and Environmental Chemistry Antioxidants - chemical synthesis Antioxidants - chemistry Caffeic Acids - chemistry Coumaric Acids - chemistry Esters - chemistry Food engineering Life Sciences Molecular Structure |
| title | Synthesis and Evaluation of Antioxidant Activities of Novel Hydroxyalkyl Esters and Bis-Aryl Esters Based on Sinapic and Caffeic Acids |
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