Chemo-enzymatic synthesis of renewable sterically-hindered phenolic antioxidants with tunable polarity from lignocellulose and vegetal oil components
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 desi...
Published in: | International Journal of Molecular Sciences |
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Online Access: | http://prodinra.inra.fr/ft/DD61E6AD-5872-40A7-8D80-0D158471238F http://prodinra.inra.fr/record/463609 https://doi.org/10.3390/ijms19113358 |
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ftinraparis:oai:prodinra.inra.fr:463609 2023-05-15T13:58:37+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 2018 application/pdf http://prodinra.inra.fr/ft/DD61E6AD-5872-40A7-8D80-0D158471238F http://prodinra.inra.fr/record/463609 https://doi.org/10.3390/ijms19113358 eng eng https://creativecommons.org/licenses/by/3.0/ CC-BY International Journal of Molecular Sciences 11 (19), . (2018) ferulic acid;fatty acid ethyl esters;CAL-B;antioxidant;DPPH ARTICLE 2018 ftinraparis https://doi.org/10.3390/ijms19113358 2019-03-05T23:25:10Z 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 Institut National de la Recherche Agronomique: ProdINRA International Journal of Molecular Sciences 19 11 3358 |
institution |
Open Polar |
collection |
Institut National de la Recherche Agronomique: ProdINRA |
op_collection_id |
ftinraparis |
language |
English |
topic |
ferulic acid;fatty acid ethyl esters;CAL-B;antioxidant;DPPH |
spellingShingle |
ferulic acid;fatty acid ethyl esters;CAL-B;antioxidant;DPPH Hollande, Louis Domenek, Sandra 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 |
description |
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 |
Allais, Florent |
format |
Article in Journal/Newspaper |
author |
Hollande, Louis Domenek, Sandra |
author_facet |
Hollande, Louis Domenek, Sandra |
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 |
publishDate |
2018 |
url |
http://prodinra.inra.fr/ft/DD61E6AD-5872-40A7-8D80-0D158471238F http://prodinra.inra.fr/record/463609 https://doi.org/10.3390/ijms19113358 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
International Journal of Molecular Sciences 11 (19), . (2018) |
op_rights |
https://creativecommons.org/licenses/by/3.0/ |
op_rightsnorm |
CC-BY |
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_ |
1766266974140104704 |