Chemo-enzymatic synthesis of renewable sterically-hindered phenolic antioxidants with tunable polarity from lignocellulose and vegetal oil components
International audience Despite their great antioxidant activities, the use of natural phenols as antioxidant additives for polyolefins is limited owing to their weak thermal stability and hydrophilic character. Herein, we report a sustainable chemo-enzymatic synthesis of renewable lipophilic antioxi...
Published in: | International Journal of Molecular Sciences |
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Online Access: | https://hal.inrae.fr/hal-02621016 https://hal.inrae.fr/hal-02621016/document https://hal.inrae.fr/hal-02621016/file/2018_Hollande_International%20Journal%20of%20Molecular%20Sciences_1.pdf https://doi.org/10.3390/ijms19113358 |
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ftccsdartic:oai:HAL:hal-02621016v1 2023-05-15T13:37:36+02:00 Chemo-enzymatic synthesis of renewable sterically-hindered phenolic antioxidants with tunable polarity from lignocellulose and vegetal oil components Hollande, Louis DOMENEK, Sandra Allais, Florent Agro-Biotechnologies Industrielles (ABI) AgroParisTech Ingénierie, Procédés, Aliments (GENIAL) Institut National de la Recherche Agronomique (INRA)-AgroParisTech Université Paris Saclay (COmUE) Grand Reims, Conseil General de la Marne; Region Grand Est 2018 https://hal.inrae.fr/hal-02621016 https://hal.inrae.fr/hal-02621016/document https://hal.inrae.fr/hal-02621016/file/2018_Hollande_International%20Journal%20of%20Molecular%20Sciences_1.pdf https://doi.org/10.3390/ijms19113358 en eng HAL CCSD MDPI info:eu-repo/semantics/altIdentifier/doi/10.3390/ijms19113358 info:eu-repo/semantics/altIdentifier/pmid/30373201 hal-02621016 https://hal.inrae.fr/hal-02621016 https://hal.inrae.fr/hal-02621016/document https://hal.inrae.fr/hal-02621016/file/2018_Hollande_International%20Journal%20of%20Molecular%20Sciences_1.pdf doi:10.3390/ijms19113358 PRODINRA: 463609 PUBMED: 30373201 WOS: 000451528500074 http://creativecommons.org/licenses/by/ info:eu-repo/semantics/OpenAccess ISSN: 1661-6596 EISSN: 1422-0067 International Journal of Molecular Sciences https://hal.inrae.fr/hal-02621016 International Journal of Molecular Sciences, MDPI, 2018, 19 (11), ⟨10.3390/ijms19113358⟩ ferulic acid fatty acid ethyl esters CAL-B antioxidant DPPH [SDV]Life Sciences [q-bio] [SDV.IDA]Life Sciences [q-bio]/Food engineering [SPI.GPROC]Engineering Sciences [physics]/Chemical and Process Engineering [SDV.BV]Life Sciences [q-bio]/Vegetal Biology info:eu-repo/semantics/article Journal articles 2018 ftccsdartic https://doi.org/10.3390/ijms19113358 2021-11-07T01:06:06Z International audience Despite their great antioxidant activities, the use of natural phenols as antioxidant additives for polyolefins is limited owing to their weak thermal stability and hydrophilic character. Herein, we report a sustainable chemo-enzymatic synthesis of renewable lipophilic antioxidants specifically designed to overcome these restrictions using naturally occurring ferulic acid (found in lignocellulose) and vegetal oils (i.e., lauric, palmitic, stearic acids, and glycerol) as starting materials. A predictive Hansen and Hildebrand parameters-based approach was used to tailor the polarity of newly designed structures. A specific affinity of Candida antarctica lipase B (CAL-B) towards glycerol was demonstrated and exploited to efficiently synthesized the target compounds in yields ranging from 81 to 87%. Antiradical activity as well as radical scavenging behavior (H atom-donation, kinetics) of these new fully biobased additives were found superior to that of well-established, commercially available fossil-based antioxidants such as Irganox 1010((R)) and Irganox 1076((R)). Finally, their greater thermal stabilities (302 < T(d)5% < 311 degrees C), established using thermal gravimetric analysis, combined with their high solubilities and antioxidant activities, make these novel sustainable phenolics a very attractive alternative to current fossil-based antioxidant additives in polyolefins. Article in Journal/Newspaper Antarc* Antarctica Archive ouverte HAL (Hyper Article en Ligne, CCSD - Centre pour la Communication Scientifique Directe) International Journal of Molecular Sciences 19 11 3358 |
institution |
Open Polar |
collection |
Archive ouverte HAL (Hyper Article en Ligne, CCSD - Centre pour la Communication Scientifique Directe) |
op_collection_id |
ftccsdartic |
language |
English |
topic |
ferulic acid fatty acid ethyl esters CAL-B antioxidant DPPH [SDV]Life Sciences [q-bio] [SDV.IDA]Life Sciences [q-bio]/Food engineering [SPI.GPROC]Engineering Sciences [physics]/Chemical and Process Engineering [SDV.BV]Life Sciences [q-bio]/Vegetal Biology |
spellingShingle |
ferulic acid fatty acid ethyl esters CAL-B antioxidant DPPH [SDV]Life Sciences [q-bio] [SDV.IDA]Life Sciences [q-bio]/Food engineering [SPI.GPROC]Engineering Sciences [physics]/Chemical and Process Engineering [SDV.BV]Life Sciences [q-bio]/Vegetal Biology Hollande, Louis DOMENEK, Sandra Allais, Florent Chemo-enzymatic synthesis of renewable sterically-hindered phenolic antioxidants with tunable polarity from lignocellulose and vegetal oil components |
topic_facet |
ferulic acid fatty acid ethyl esters CAL-B antioxidant DPPH [SDV]Life Sciences [q-bio] [SDV.IDA]Life Sciences [q-bio]/Food engineering [SPI.GPROC]Engineering Sciences [physics]/Chemical and Process Engineering [SDV.BV]Life Sciences [q-bio]/Vegetal Biology |
description |
International audience Despite their great antioxidant activities, the use of natural phenols as antioxidant additives for polyolefins is limited owing to their weak thermal stability and hydrophilic character. Herein, we report a sustainable chemo-enzymatic synthesis of renewable lipophilic antioxidants specifically designed to overcome these restrictions using naturally occurring ferulic acid (found in lignocellulose) and vegetal oils (i.e., lauric, palmitic, stearic acids, and glycerol) as starting materials. A predictive Hansen and Hildebrand parameters-based approach was used to tailor the polarity of newly designed structures. A specific affinity of Candida antarctica lipase B (CAL-B) towards glycerol was demonstrated and exploited to efficiently synthesized the target compounds in yields ranging from 81 to 87%. Antiradical activity as well as radical scavenging behavior (H atom-donation, kinetics) of these new fully biobased additives were found superior to that of well-established, commercially available fossil-based antioxidants such as Irganox 1010((R)) and Irganox 1076((R)). Finally, their greater thermal stabilities (302 < T(d)5% < 311 degrees C), established using thermal gravimetric analysis, combined with their high solubilities and antioxidant activities, make these novel sustainable phenolics a very attractive alternative to current fossil-based antioxidant additives in polyolefins. |
author2 |
Agro-Biotechnologies Industrielles (ABI) AgroParisTech Ingénierie, Procédés, Aliments (GENIAL) Institut National de la Recherche Agronomique (INRA)-AgroParisTech Université Paris Saclay (COmUE) Grand Reims, Conseil General de la Marne; Region Grand Est |
format |
Article in Journal/Newspaper |
author |
Hollande, Louis DOMENEK, Sandra Allais, Florent |
author_facet |
Hollande, Louis DOMENEK, Sandra Allais, Florent |
author_sort |
Hollande, Louis |
title |
Chemo-enzymatic synthesis of renewable sterically-hindered phenolic antioxidants with tunable polarity from lignocellulose and vegetal oil components |
title_short |
Chemo-enzymatic synthesis of renewable sterically-hindered phenolic antioxidants with tunable polarity from lignocellulose and vegetal oil components |
title_full |
Chemo-enzymatic synthesis of renewable sterically-hindered phenolic antioxidants with tunable polarity from lignocellulose and vegetal oil components |
title_fullStr |
Chemo-enzymatic synthesis of renewable sterically-hindered phenolic antioxidants with tunable polarity from lignocellulose and vegetal oil components |
title_full_unstemmed |
Chemo-enzymatic synthesis of renewable sterically-hindered phenolic antioxidants with tunable polarity from lignocellulose and vegetal oil components |
title_sort |
chemo-enzymatic synthesis of renewable sterically-hindered phenolic antioxidants with tunable polarity from lignocellulose and vegetal oil components |
publisher |
HAL CCSD |
publishDate |
2018 |
url |
https://hal.inrae.fr/hal-02621016 https://hal.inrae.fr/hal-02621016/document https://hal.inrae.fr/hal-02621016/file/2018_Hollande_International%20Journal%20of%20Molecular%20Sciences_1.pdf https://doi.org/10.3390/ijms19113358 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
ISSN: 1661-6596 EISSN: 1422-0067 International Journal of Molecular Sciences https://hal.inrae.fr/hal-02621016 International Journal of Molecular Sciences, MDPI, 2018, 19 (11), ⟨10.3390/ijms19113358⟩ |
op_relation |
info:eu-repo/semantics/altIdentifier/doi/10.3390/ijms19113358 info:eu-repo/semantics/altIdentifier/pmid/30373201 hal-02621016 https://hal.inrae.fr/hal-02621016 https://hal.inrae.fr/hal-02621016/document https://hal.inrae.fr/hal-02621016/file/2018_Hollande_International%20Journal%20of%20Molecular%20Sciences_1.pdf doi:10.3390/ijms19113358 PRODINRA: 463609 PUBMED: 30373201 WOS: 000451528500074 |
op_rights |
http://creativecommons.org/licenses/by/ info:eu-repo/semantics/OpenAccess |
op_doi |
https://doi.org/10.3390/ijms19113358 |
container_title |
International Journal of Molecular Sciences |
container_volume |
19 |
container_issue |
11 |
container_start_page |
3358 |
_version_ |
1766094502111477760 |