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Scalable synthesis of oleoyl ethanolamide by chemical amidation in a mixed solvent

  • Original Paper
  • Published:
Journal of the American Oil Chemists' Society

Abstract

Oleoyl ethanolamide is a lipid mediator that exhibits biological activity in animal and cell models. In this study, an effective process is described to synthesize oleoyl ethanolamide by chemical amidation with native oil used as an acyl donor in the presence of sodium methoxide. Reaction conditions were optimized. When the amidation reaction was conducted in a mixed solvent, by reacting 2 mmol high oleic sunflower oil and 20 mmol ethanolamine in the presence of 1.5 % sodium methoxide with agitation, >90 % fatty acid ethanolamide was formed after 3 h of reaction time. The fatty acid ethanolamide product was purified by a two-step crystallization process to prepare oleoyl ethanolamide. Highly pure oleoyl ethanolamide was obtained in a 70.3 % molar yield. The novelty of the work is the use of native oil as acyl donor and the mixed solvent used as the reaction media. The use of native oil avoids the formation of ion pairs with ethanolamine that can occur in other synthesis routes.

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Acknowledgments

This work was financially supported by “The Natural Science Foundation of Jiangsu Province (Grants No BK20150137)” and “National Natural Science Foundation of China (31401525)”.

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Authors and Affiliations

  1. State Key Laboratory of Food Science and Technology, Synergetic Innovation Center of Food Safety and Nutrition, School of Food Science and Technology, Jiangnan University, 1800 Lihu Road, Wuxi, Jiangsu, 214122, People’s Republic of China

    Xiaosan Wang, Zhengyang Han, Yang Chen, Qingzhe Jin & Xingguo Wang

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  1. Xiaosan Wang
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  2. Zhengyang Han
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  3. Yang Chen
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  4. Qingzhe Jin
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  5. Xingguo Wang
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Correspondence to Xiaosan Wang or Xingguo Wang.

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Wang, X., Han, Z., Chen, Y. et al. Scalable synthesis of oleoyl ethanolamide by chemical amidation in a mixed solvent. J Am Oil Chem Soc 93, 125–131 (2016). https://doi.org/10.1007/s11746-015-2749-6

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  • DOI: https://doi.org/10.1007/s11746-015-2749-6

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