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An Improved Method for Synthesis of N-stearoyl and N-palmitoylethanolamine

  • Original Paper
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Journal of the American Oil Chemists' Society

Abstract

Certain N-acylethanolamines interact with cannabinoid receptors and have anorexic and neuroprotective effects. Traditional methods for the synthesis of N-acylethanolamines use fatty acid chlorides, fatty acid methyl esters, free fatty acids and triacylglycerols as acyl donors to react with ethanolamine. In the present study, we investigated the feasibility of using fatty acid vinyl esters as the acyl donor to synthesize N-stearoyl and N-palmitoylethanolamine. Theoretically, the use of fatty acid vinyl esters should lead to an irreversible reaction because the volatile acetaldehyde by-product is easily removed. Four reaction conditions, i.e. catalyst concentration, substrate ratio, temperature, and time were evaluated. The reaction performed at mild temperatures and with an excess amount of ethanolamine which acted as both reactant and solvent resulted in the formation of high purity N-stearoyl and N-palmitoylethanolamine. When 20 mmol ethanolamine was reacted with 1 mmol vinyl stearate at 80 °C for 1 h with 1% sodium methoxide as catalyst, N-stearoylethanolamine with 96% purity was obtained after the removal of excess ethanolamine without further purification, while N-palmitoylethanolamine with 98% purity was obtained by reacting with the same substrate ratio at 60 °C for 1.5 h with 3% catalyst. Complete conversion of vinyl stearate and palmitate was achieved.

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Acknowledgments

We thank Drs. Linxing Yao and Jose Gerde for assistance with GC instrumentation from Department of Food Science and Human Nutrition, Iowa State University. We also acknowledge the Chinese Government for providing sponsorship for the Ph.D. graduate student, Xiaosan Wang, who conducted this research.

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Authors and Affiliations

  1. Department of Food Science and Human Nutrition, Iowa State University, 2312 Food Science Building, Ames, IA, 50011-1061, USA

    Xiaosan Wang & Tong Wang

  2. State Key Laboratory of Food Science and Technology, School of Food Science and Technology, Jiangnan University, No. 1800 Lihu Road Wuxi, 214122, Jiangsu, People’s Republic of China

    Xiaosan Wang & Xingguo Wang

Authors
  1. Xiaosan Wang
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  2. Tong Wang
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  3. Xingguo Wang
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Correspondence to Tong Wang.

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Wang, X., Wang, T. & Wang, X. An Improved Method for Synthesis of N-stearoyl and N-palmitoylethanolamine. J Am Oil Chem Soc 89, 1305–1313 (2012). https://doi.org/10.1007/s11746-012-2017-y

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  • DOI: https://doi.org/10.1007/s11746-012-2017-y

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