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Medium-chain alkyl esters of tyrosol and hydroxytyrosol antioxidants by cuphea oil transesterification†
Article first published online: 29 JAN 2013
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
European Journal of Lipid Science and Technology
Volume 115, Issue 3, pages 363–371, March 2013
How to Cite
Laszlo, J. A., Cermak, S. C., Evans, K. O., Compton, D. L., Evangelista, R. and Berhow, M. A. (2013), Medium-chain alkyl esters of tyrosol and hydroxytyrosol antioxidants by cuphea oil transesterification. Eur. J. Lipid Sci. Technol., 115: 363–371. doi: 10.1002/ejlt.201200296
- Issue published online: 13 MAR 2013
- Article first published online: 29 JAN 2013
- Accepted manuscript online: 25 NOV 2012 06:50PM EST
- Manuscript Accepted: 30 OCT 2012
- Manuscript Revised: 12 OCT 2012
- Manuscript Received: 16 AUG 2012
- Olive oil waste;
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.