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Int. J. Mol. Sci. 2018, 19(11), 3358; https://doi.org/10.3390/ijms19113358

Chemo-Enzymatic Synthesis of Renewable Sterically-Hindered Phenolic Antioxidants with Tunable Polarity from Lignocellulose and Vegetal Oil Components

1
Chaire ABI, AgroParisTech, CEBB 3 rue des Rouges Terres 51110 Pomacle, France
2
UMR GENIAL, AgroParisTech, INRA, Université Paris-Saclay, Avenue des Olympiades, 91300 Massy, France
*
Author to whom correspondence should be addressed.
Received: 28 September 2018 / Revised: 23 October 2018 / Accepted: 24 October 2018 / Published: 26 October 2018
(This article belongs to the Special Issue Biobased and/or Biodegradable Polymeric Materials)
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Abstract

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® and Irganox 1076®. Finally, their greater thermal stabilities (302 < Td5% < 311 °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. View Full-Text
Keywords: ferulic acid; fatty acid ethyl esters; CAL-B; antioxidant; DPPH ferulic acid; fatty acid ethyl esters; CAL-B; antioxidant; DPPH
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Hollande, L.; Domenek, S.; Allais, F. Chemo-Enzymatic Synthesis of Renewable Sterically-Hindered Phenolic Antioxidants with Tunable Polarity from Lignocellulose and Vegetal Oil Components. Int. J. Mol. Sci. 2018, 19, 3358.

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