Enzymatic Synthesis of Lipophilic Esters of Phenolic Compounds, Evaluation of Their Antioxidant Activity and Effect on the Oxidative Stability of Selected Oils
The aim of the study was to compare the effect of the substituent and its position in the aromatic ring on the antioxidant activity of hexanoic acid esters obtained in reactions catalyzed by immobilized lipase B from Candida antarctica . 4-Hydroxybenzyl hexanoate, 2-hydroxybenzyl hexanoate, 4-methox...
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MDPI AG
2021
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ftdoajarticles:oai:doaj.org/article:225508519ad84c4ea23928be605c77e3 2024-01-14T10:00:08+01:00 Enzymatic Synthesis of Lipophilic Esters of Phenolic Compounds, Evaluation of Their Antioxidant Activity and Effect on the Oxidative Stability of Selected Oils Bartłomiej Zieniuk Katarzyna Groborz Małgorzata Wołoszynowska Katarzyna Ratusz Ewa Białecka-Florjańczyk Agata Fabiszewska 2021-02-01T00:00:00Z https://doi.org/10.3390/biom11020314 https://doaj.org/article/225508519ad84c4ea23928be605c77e3 EN eng MDPI AG https://www.mdpi.com/2218-273X/11/2/314 https://doaj.org/toc/2218-273X doi:10.3390/biom11020314 2218-273X https://doaj.org/article/225508519ad84c4ea23928be605c77e3 Biomolecules, Vol 11, Iss 2, p 314 (2021) CALB enzymatic esterification phenolic compounds antioxidant activity oxidative stability vanillyl hexanoate Microbiology QR1-502 article 2021 ftdoajarticles https://doi.org/10.3390/biom11020314 2023-12-17T01:45:37Z The aim of the study was to compare the effect of the substituent and its position in the aromatic ring on the antioxidant activity of hexanoic acid esters obtained in reactions catalyzed by immobilized lipase B from Candida antarctica . 4-Hydroxybenzyl hexanoate, 2-hydroxybenzyl hexanoate, 4-methoxybenzyl hexanoate, and vanillyl hexanoate were obtained with conversion yields of 50 to 80%. The antioxidant activity of synthesized esters, their alcohol precursors and BHT (Butylated HydroxyToluene) was compared with DPPH (2,2-diphenyl-1-picrylhydrazyl), CUPRAC (cupric ion reducing antioxidant capacity), and CBA (crocin bleaching assay) methods. Furthermore, it was investigated whether the presence of vanillyl hexanoate in a concentration of 0.01 and 0.1% affected the oxidative stability of sunflower and rapeseed oils in the Rancimat test. It was observed that the antioxidant activity of hexanoic acid esters depends on the presence and position of the hydroxyl group in the aromatic ring. The highest activities were found for vanillyl alcohol, vanillyl hexanoate, and BHT. The addition of the ester and BHT significantly extended the induction times of the tested oils, and these compounds exhibited similar activity. Vanillyl hexanoate increased the induction time from 4.49 to 5.28 h and from 2.73 to 3.12 h in the case of rapeseed and sunflower oils, respectively. Article in Journal/Newspaper Antarc* Antarctica Directory of Open Access Journals: DOAJ Articles Biomolecules 11 2 314 |
institution |
Open Polar |
collection |
Directory of Open Access Journals: DOAJ Articles |
op_collection_id |
ftdoajarticles |
language |
English |
topic |
CALB enzymatic esterification phenolic compounds antioxidant activity oxidative stability vanillyl hexanoate Microbiology QR1-502 |
spellingShingle |
CALB enzymatic esterification phenolic compounds antioxidant activity oxidative stability vanillyl hexanoate Microbiology QR1-502 Bartłomiej Zieniuk Katarzyna Groborz Małgorzata Wołoszynowska Katarzyna Ratusz Ewa Białecka-Florjańczyk Agata Fabiszewska Enzymatic Synthesis of Lipophilic Esters of Phenolic Compounds, Evaluation of Their Antioxidant Activity and Effect on the Oxidative Stability of Selected Oils |
topic_facet |
CALB enzymatic esterification phenolic compounds antioxidant activity oxidative stability vanillyl hexanoate Microbiology QR1-502 |
description |
The aim of the study was to compare the effect of the substituent and its position in the aromatic ring on the antioxidant activity of hexanoic acid esters obtained in reactions catalyzed by immobilized lipase B from Candida antarctica . 4-Hydroxybenzyl hexanoate, 2-hydroxybenzyl hexanoate, 4-methoxybenzyl hexanoate, and vanillyl hexanoate were obtained with conversion yields of 50 to 80%. The antioxidant activity of synthesized esters, their alcohol precursors and BHT (Butylated HydroxyToluene) was compared with DPPH (2,2-diphenyl-1-picrylhydrazyl), CUPRAC (cupric ion reducing antioxidant capacity), and CBA (crocin bleaching assay) methods. Furthermore, it was investigated whether the presence of vanillyl hexanoate in a concentration of 0.01 and 0.1% affected the oxidative stability of sunflower and rapeseed oils in the Rancimat test. It was observed that the antioxidant activity of hexanoic acid esters depends on the presence and position of the hydroxyl group in the aromatic ring. The highest activities were found for vanillyl alcohol, vanillyl hexanoate, and BHT. The addition of the ester and BHT significantly extended the induction times of the tested oils, and these compounds exhibited similar activity. Vanillyl hexanoate increased the induction time from 4.49 to 5.28 h and from 2.73 to 3.12 h in the case of rapeseed and sunflower oils, respectively. |
format |
Article in Journal/Newspaper |
author |
Bartłomiej Zieniuk Katarzyna Groborz Małgorzata Wołoszynowska Katarzyna Ratusz Ewa Białecka-Florjańczyk Agata Fabiszewska |
author_facet |
Bartłomiej Zieniuk Katarzyna Groborz Małgorzata Wołoszynowska Katarzyna Ratusz Ewa Białecka-Florjańczyk Agata Fabiszewska |
author_sort |
Bartłomiej Zieniuk |
title |
Enzymatic Synthesis of Lipophilic Esters of Phenolic Compounds, Evaluation of Their Antioxidant Activity and Effect on the Oxidative Stability of Selected Oils |
title_short |
Enzymatic Synthesis of Lipophilic Esters of Phenolic Compounds, Evaluation of Their Antioxidant Activity and Effect on the Oxidative Stability of Selected Oils |
title_full |
Enzymatic Synthesis of Lipophilic Esters of Phenolic Compounds, Evaluation of Their Antioxidant Activity and Effect on the Oxidative Stability of Selected Oils |
title_fullStr |
Enzymatic Synthesis of Lipophilic Esters of Phenolic Compounds, Evaluation of Their Antioxidant Activity and Effect on the Oxidative Stability of Selected Oils |
title_full_unstemmed |
Enzymatic Synthesis of Lipophilic Esters of Phenolic Compounds, Evaluation of Their Antioxidant Activity and Effect on the Oxidative Stability of Selected Oils |
title_sort |
enzymatic synthesis of lipophilic esters of phenolic compounds, evaluation of their antioxidant activity and effect on the oxidative stability of selected oils |
publisher |
MDPI AG |
publishDate |
2021 |
url |
https://doi.org/10.3390/biom11020314 https://doaj.org/article/225508519ad84c4ea23928be605c77e3 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Biomolecules, Vol 11, Iss 2, p 314 (2021) |
op_relation |
https://www.mdpi.com/2218-273X/11/2/314 https://doaj.org/toc/2218-273X doi:10.3390/biom11020314 2218-273X https://doaj.org/article/225508519ad84c4ea23928be605c77e3 |
op_doi |
https://doi.org/10.3390/biom11020314 |
container_title |
Biomolecules |
container_volume |
11 |
container_issue |
2 |
container_start_page |
314 |
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1788063670417227776 |