Antioxidant properties of two novel lipophilic gallic acid derivatives

The effectiveness of two lipophilic derivatives of the natural phenol, gallic acid (GA), synthesized using methyl gallate as starting material was investigated. The antioxidant activities of these novel phenolics compared to GA, tert-butylhydroquinone (TBHQ) and butylated hydroxytoluene (BHT) were...

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Main Authors: T.M. Olajide, T. Liu, X.C. Weng, X.Y. Liao, J.Y. Huang
Format: Article
Language:English
Published: Consejo Superior de Investigaciones Científicas 2022-09-01
Series:Grasas y Aceites
Subjects:
Online Access:https://grasasyaceites.revistas.csic.es/index.php/grasasyaceites/article/view/1950
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author T.M. Olajide
T. Liu
X.C. Weng
X.Y. Liao
J.Y. Huang
author_facet T.M. Olajide
T. Liu
X.C. Weng
X.Y. Liao
J.Y. Huang
author_sort T.M. Olajide
collection DOAJ
description The effectiveness of two lipophilic derivatives of the natural phenol, gallic acid (GA), synthesized using methyl gallate as starting material was investigated. The antioxidant activities of these novel phenolics compared to GA, tert-butylhydroquinone (TBHQ) and butylated hydroxytoluene (BHT) were evaluated in bulk oil, emulsion and the DPPH systems. The results showed that the new compounds effectively delayed lipid oxidation much better than GA and other antioxidants under Rancimat (100-140 °C) and emulsion tests. In the bulk oil system at 65 °C, they still behaved better than GA, but TBHQ had the highest activity. Thus, replacing the electron-withdrawing carboxylic group on GA by covalently linking sterically hindered phenols to its phenyl ring increased its lipophilicity and also resulted in synergistic effects which improved overall antioxidant activity through stabilization of the phenoxy radical. These new antioxidant variants satisfy industrial demands for bioactive ingredients with strong antioxidant potentials under different food processing conditions.
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spelling doaj.art-8a19dfba5e8b40f8a083f4e42533e97a2022-12-22T04:32:20ZengConsejo Superior de Investigaciones CientíficasGrasas y Aceites0017-34951988-42142022-09-0173310.3989/gya.0325211Antioxidant properties of two novel lipophilic gallic acid derivativesT.M. Olajide0T. Liu1X.C. Weng2X.Y. Liao3J.Y. Huang4School of Environmental and Chemical Engineering, Shanghai University - School of Life Sciences, Shanghai UniversitySchool of Environmental and Chemical Engineering, Shanghai University - School of Life Sciences, Shanghai UniversitySchool of Life Sciences, Shanghai UniversitySchool of Life Sciences, Shanghai UniversitySchool of Life Sciences, Shanghai University The effectiveness of two lipophilic derivatives of the natural phenol, gallic acid (GA), synthesized using methyl gallate as starting material was investigated. The antioxidant activities of these novel phenolics compared to GA, tert-butylhydroquinone (TBHQ) and butylated hydroxytoluene (BHT) were evaluated in bulk oil, emulsion and the DPPH systems. The results showed that the new compounds effectively delayed lipid oxidation much better than GA and other antioxidants under Rancimat (100-140 °C) and emulsion tests. In the bulk oil system at 65 °C, they still behaved better than GA, but TBHQ had the highest activity. Thus, replacing the electron-withdrawing carboxylic group on GA by covalently linking sterically hindered phenols to its phenyl ring increased its lipophilicity and also resulted in synergistic effects which improved overall antioxidant activity through stabilization of the phenoxy radical. These new antioxidant variants satisfy industrial demands for bioactive ingredients with strong antioxidant potentials under different food processing conditions. https://grasasyaceites.revistas.csic.es/index.php/grasasyaceites/article/view/1950Antioxidant activityFree radical scavengingGallic acid derivativesLipophilicityOil-in-water emulsionRancimat test
spellingShingle T.M. Olajide
T. Liu
X.C. Weng
X.Y. Liao
J.Y. Huang
Antioxidant properties of two novel lipophilic gallic acid derivatives
Grasas y Aceites
Antioxidant activity
Free radical scavenging
Gallic acid derivatives
Lipophilicity
Oil-in-water emulsion
Rancimat test
title Antioxidant properties of two novel lipophilic gallic acid derivatives
title_full Antioxidant properties of two novel lipophilic gallic acid derivatives
title_fullStr Antioxidant properties of two novel lipophilic gallic acid derivatives
title_full_unstemmed Antioxidant properties of two novel lipophilic gallic acid derivatives
title_short Antioxidant properties of two novel lipophilic gallic acid derivatives
title_sort antioxidant properties of two novel lipophilic gallic acid derivatives
topic Antioxidant activity
Free radical scavenging
Gallic acid derivatives
Lipophilicity
Oil-in-water emulsion
Rancimat test
url https://grasasyaceites.revistas.csic.es/index.php/grasasyaceites/article/view/1950
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AT tliu antioxidantpropertiesoftwonovellipophilicgallicacidderivatives
AT xcweng antioxidantpropertiesoftwonovellipophilicgallicacidderivatives
AT xyliao antioxidantpropertiesoftwonovellipophilicgallicacidderivatives
AT jyhuang antioxidantpropertiesoftwonovellipophilicgallicacidderivatives