Chemoenzymatically synthesized policosanyl phenolates as autoxidation inhibitors

• Published in: European Journal of Lipid Science and Technology
• Main Authors: Wang, Zhiqiang, Hwang, Seung Hwan, Lim, Soon Sung
• Other Authors: National Research Foundation of Korea, Hallym University Research Fund
• Format: Article in Journal/Newspaper
• Language: English
• Published: Wiley 2014
• Subjects: Antarc*; Antarctica
• Online Access: http://dx.doi.org/10.1002/ejlt.201400296; https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fejlt.201400296; https://onlinelibrary.wiley.com/doi/pdf/10.1002/ejlt.201400296; https://onlinelibrary.wiley.com/doi/full-xml/10.1002/ejlt.201400296

In this study, ten policosanyl phenolates were synthesized via a two‐step chemoenzymatic route. The intermediate vinyl esters were first chemically produced and subsequently esterified with policosanols catalyzed by Novozyme 435 ( Candida antarctica lipase B). The conversion yields of the policosanyl phenolates were in the range of 4.20–37.14%. Their antioxidant activities were evaluated. Results showed that, compared with the corresponding phenolic acids, all synthesized policosanyl phenolates had better activities for peroxide value, but worse for 2,2'‐azinobis(3‐ethylbenzothiazoline‐6‐sulfonic acid) assay; policosanyl p ‐coumarate and policosanyl 5‐phenylvalerate showed a moderate and durable inhibition effect on lipid oxidation both in a linoleic acid system and a cooked pork system. Practical applications: It is important to develop antioxidants from natural sources. The lipophilization of phenolic acids with fatty alcohols can improve the hydrophobicity and change the antioxidant capacity of phenols. This study focuses on policosanol, which is a food‐grade mixture of long‐chain aliphatic primary alcohols, having development and application potential as a cost‐effective food additive. According to our results, policosanyl phenolates, which are a new range of amphiphilic antioxidant molecules, have the potential for use as alternative food antioxidants in the food industry. The policosanyl phenolates were synthesized via a two‐step route as shown in the figure. The intermediate vinyl esters were first chemically produced and subsequently esterified with policosanols catalyzed by Novozyme 435 ( Candida antarctica lipase B).