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Improved Synthesis Methods for N-acylethanolamines
Category(s):
For Information, Contact:
Craig Forney
Commercialization Manager, Chemistry and Materials Sciences
515-294-4740
licensing@iastate.edu
Web Published:
5/4/2015
ISURF #
4021
Summary:
Simple and efficient method to obtain n-stearoyl and n-palmitoylethanolamines

Development Stage:
Samples have been successfully prepared

Description:
N-acylethanolamines of different chain length and structure exhibit a variety of biological activities and have been shown to reduce allergic reactions, inhibit mast cell degranulation, and exert neuroprotective effects in mammals. N-oleoythethanolamine exerts anorexigenic effects by binding to the nuclear receptors that cause appetite suppression, leading to body fat loss.  The University of California, Irvine, holds two patnets on the methods, compounds, and compositions for reducing body fat, appetite, body weight, food intake, and modulating fatty acid metabolism (US Patent Nos. 6,611,474 and 7,423,066) using n-oleoylethanolamine.  Traditional methods for the synthesis of these compounds use fatty acid chlorides, fatty acid methyl esters, free fatty acids and triacylglycerols as acyl donors to react with ethanolamine.  However, these methods result in low yields, and as a consequence, the n-acylethanoloamine compounds were high cost, limiting their commercial application.   Iowa State University researchers have discovered new approaches to obtain n-stearoyl and n-palmitoylethanolamines through simple and efficient methods using economical starting materials, as well as an effective process for the enzymatic synthesis of oleoylethanolamide.  Using these novel schemes, high yields with purities of >95% have been achieved with low energy input and reduced reaction time.  The scalability of these synthesis methods now provide for economical production of these nutraceutical products.  This technology is available for licensing, and ISU is seeking commercialization partners.

Advantage:
• Fast synthesis reaction
• Mild reaction conditions
• High purities (>95%)
Application:
Nutraceuticals

References:
Patent Information:
*To see the full version of the patent(s), follow the link below, then click on "Images" button.
Country Serial No. Patent No. Issued Date
United States 13/869,099 9,221,747* 12/29/2015


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