Medium‐chain alkyl esters of tyrosol and hydroxytyrosol antioxidants by cuphea oil transesterification
Abstract Effective lipophilic antioxidants were prepared by non‐aqueous enzymatic transesterification of plant phenols with cuphea oil. Tyrosol and hydroxytyrosol, abundantly available phenols from olive oil processing byproduct, were found to be predominately acylated with capric acid derived from...
Published in: | European Journal of Lipid Science and Technology |
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crwiley:10.1002/ejlt.201200296 2024-06-02T07:57:49+00:00 Medium‐chain alkyl esters of tyrosol and hydroxytyrosol antioxidants by cuphea oil transesterification Laszlo, Joseph A. Cermak, Steven C. Evans, Kervin O. Compton, David L. Evangelista, Roque Berhow, Mark A. 2013 http://dx.doi.org/10.1002/ejlt.201200296 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fejlt.201200296 https://onlinelibrary.wiley.com/doi/pdf/10.1002/ejlt.201200296 https://onlinelibrary.wiley.com/doi/full-xml/10.1002/ejlt.201200296 en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor European Journal of Lipid Science and Technology volume 115, issue 3, page 363-371 ISSN 1438-7697 1438-9312 journal-article 2013 crwiley https://doi.org/10.1002/ejlt.201200296 2024-05-03T10:39:24Z Abstract Effective lipophilic antioxidants were prepared by non‐aqueous enzymatic transesterification of plant phenols with cuphea oil. Tyrosol and hydroxytyrosol, abundantly available phenols from olive oil processing byproduct, were found to be predominately acylated with capric acid derived from the triglyceride fraction of the Cuphea germplasm line PSR 23 ( Cuphea Viscosissima × C. lanceolata ). The reaction was complete within 2 h, with a >97% conversion of either phenol using immobilized Candida antarctica lipase B. The reaction products were good solvents for tyrosol or hydroxytyrosol, suggesting a facile manufacturing route not dependent on use of organic solvents. Phenolic derivatives were assessed for their ability to serve as antioxidants for preventing the oxidation of polyunsaturated fatty acyl groups. The antioxidant capacities of the cuphea‐derived fatty acyl derivatives of tyrosol or hydroxytyrosol were the same as their respective derivatives prepared from decanoic acid. These biobased antioxidants may improve the oxidative stability of sensitive fatty acids in food applications. Practical applications: A new biobased antioxidant was created for the food industry. Foods can contain fats and oils that are susceptible to deterioration during storage, which can limit product quality and shelf‐life. Synthetic antioxidants can slow the spoilage process, although there are limitations to how much can be added to foods. The food industry is interested in using natural ingredients to solve storage stability problems. We found that the oil from the plant Cuphea, cultivated in the upper Midwest region of the US, is very useful for modifying olive oil waste molecules to create antioxidants for use in foods. The developed process would be suitable for commercial production. This research creates a new commercial use for a specialty oil seed crop, expands the market for cuphea oil, and has developed two novel antioxidants to help the food industry improve food quality. Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library European Journal of Lipid Science and Technology 115 3 363 371 |
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Wiley Online Library |
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English |
description |
Abstract Effective lipophilic antioxidants were prepared by non‐aqueous enzymatic transesterification of plant phenols with cuphea oil. Tyrosol and hydroxytyrosol, abundantly available phenols from olive oil processing byproduct, were found to be predominately acylated with capric acid derived from the triglyceride fraction of the Cuphea germplasm line PSR 23 ( Cuphea Viscosissima × C. lanceolata ). The reaction was complete within 2 h, with a >97% conversion of either phenol using immobilized Candida antarctica lipase B. The reaction products were good solvents for tyrosol or hydroxytyrosol, suggesting a facile manufacturing route not dependent on use of organic solvents. Phenolic derivatives were assessed for their ability to serve as antioxidants for preventing the oxidation of polyunsaturated fatty acyl groups. The antioxidant capacities of the cuphea‐derived fatty acyl derivatives of tyrosol or hydroxytyrosol were the same as their respective derivatives prepared from decanoic acid. These biobased antioxidants may improve the oxidative stability of sensitive fatty acids in food applications. Practical applications: A new biobased antioxidant was created for the food industry. Foods can contain fats and oils that are susceptible to deterioration during storage, which can limit product quality and shelf‐life. Synthetic antioxidants can slow the spoilage process, although there are limitations to how much can be added to foods. The food industry is interested in using natural ingredients to solve storage stability problems. We found that the oil from the plant Cuphea, cultivated in the upper Midwest region of the US, is very useful for modifying olive oil waste molecules to create antioxidants for use in foods. The developed process would be suitable for commercial production. This research creates a new commercial use for a specialty oil seed crop, expands the market for cuphea oil, and has developed two novel antioxidants to help the food industry improve food quality. |
format |
Article in Journal/Newspaper |
author |
Laszlo, Joseph A. Cermak, Steven C. Evans, Kervin O. Compton, David L. Evangelista, Roque Berhow, Mark A. |
spellingShingle |
Laszlo, Joseph A. Cermak, Steven C. Evans, Kervin O. Compton, David L. Evangelista, Roque Berhow, Mark A. Medium‐chain alkyl esters of tyrosol and hydroxytyrosol antioxidants by cuphea oil transesterification |
author_facet |
Laszlo, Joseph A. Cermak, Steven C. Evans, Kervin O. Compton, David L. Evangelista, Roque Berhow, Mark A. |
author_sort |
Laszlo, Joseph A. |
title |
Medium‐chain alkyl esters of tyrosol and hydroxytyrosol antioxidants by cuphea oil transesterification |
title_short |
Medium‐chain alkyl esters of tyrosol and hydroxytyrosol antioxidants by cuphea oil transesterification |
title_full |
Medium‐chain alkyl esters of tyrosol and hydroxytyrosol antioxidants by cuphea oil transesterification |
title_fullStr |
Medium‐chain alkyl esters of tyrosol and hydroxytyrosol antioxidants by cuphea oil transesterification |
title_full_unstemmed |
Medium‐chain alkyl esters of tyrosol and hydroxytyrosol antioxidants by cuphea oil transesterification |
title_sort |
medium‐chain alkyl esters of tyrosol and hydroxytyrosol antioxidants by cuphea oil transesterification |
publisher |
Wiley |
publishDate |
2013 |
url |
http://dx.doi.org/10.1002/ejlt.201200296 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fejlt.201200296 https://onlinelibrary.wiley.com/doi/pdf/10.1002/ejlt.201200296 https://onlinelibrary.wiley.com/doi/full-xml/10.1002/ejlt.201200296 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
European Journal of Lipid Science and Technology volume 115, issue 3, page 363-371 ISSN 1438-7697 1438-9312 |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1002/ejlt.201200296 |
container_title |
European Journal of Lipid Science and Technology |
container_volume |
115 |
container_issue |
3 |
container_start_page |
363 |
op_container_end_page |
371 |
_version_ |
1800741022355947520 |