Enzymatic Lipophilization of Phenolic Acids through Esterification with Fatty Alcohols in Organic Solvents

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  • Zhiyong Yang, Denmark
  • Zheng Guo
  • Xuebing Xu, Denmark
In this study, we investigated and optimized the synthesis of lipophilized esters between selected phenolic acids and fatty alcohols in a binary solvent system, which is composed of hexane and butanone. The effect of different proportion of hexane and butanone was firstly studied by changing the volume ratio from 85:15 to 45:55. It was found that the conversion strongly depended on the proportion of hexane and butanone in the reaction system. Following the effect of carbons of fatty alcohol chains on estererification performance with dihydrocaffeic acid (DHCA) was evaluated by choosing different fatty alcohols from C4 to C18. The conversion of DHCA was significantly affected by the carbons of fatty alcohol chains. Roughly 95% conversion was achieved within 3 days when DHCA was esterified with hexanol (C6), while only 56% and 44% conversion were achieved when esterified with 1-butanol and octadecenol respectively. However, the conversions of ferulic and caffeic acids under the same conditions were much lower than DHCA. The optimal mixture ratio of hexane to butanone was found to be 65:35. Using octanol and DHCA as model, the reaction parameters, such as temperature, enzyme load, reaction time and substrate molar ratio, were optimized with response surface modelling (RSM). The optimum conditions are finalized as: temperature 60 oC, reaction time 7 days, enzyme load 100 mg, and substrate molar ratio 4.34 (octanol/DHCA).
Original languageEnglish
JournalFood Chemistry
Pages (from-to)1311-1315
Number of pages5
Publication statusPublished - 2012

    Research areas

  • Phenolic acids • Fatty alcohols • Novozym 435 • RSM

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