Preparation of amino acid-fatty acid anhydrides
View Patent ↗The present invention describes compounds produced from an amino acid molecule and a fatty acid molecule. The compounds being in the form of amino-fatty acid compounds being bound by an anhydride linkage, or mixtures thereof made by reacting amino acids or derivatives thereof with an appropriate fatty acid previously reacted with a thionyl halide. The administration of such molecules provides supplemental amino acids with enhanced bioavailability and the additional benefits conferred by the specific fatty acid.
1. A method for producing amino acid fatty acids comprising at least the steps of:
reacting an excess of a thionyl halide with a fatty acid to form an acyl halide;
neutralizing the carboxylic acid of an amino acid with an inorganic base to form an amino acid salt;
reacting the acyl halide with the amino acid salt to form an amino acid fatty acid.
2. The method of claim 1 further comprising the step of:
isolating the amino acid fatty acid.
3. The method of claim 1 wherein the halide of the thionyl halide is selected from the group consisting of fluorine, chlorine, bromine and iodine.
4. The method of claim 1 wherein the fatty acid comprises between 4 and 22 carbons.
5. The method of claim 1 wherein the acyl halide is produced at temperatures from about 35° C. to about 50° C.
6. The method of claim 1 wherein the inorganic base is selected from the group consisting of sodium hydroxide, potassium hydroxide, lithium hydroxide, ammonium hydroxide and sodium carbonate.
7. The method of claim 1 wherein the amino acid is selected from the group consisting of Glycine, Alanine, Valine, Leucine, Isoleucine, Asparagine, Glutamine, Lysine and Arginine.
8. The method of claim 2 wherein the amino acid fatty acid is isolated by distillation.
9. The method of claim 1 wherein the amino acid fatty acid has the general structure of:
wherein R 1 is selected from the group consisting of alkanes and alkenes;
said alkanes and alkenes comprise between 3 and 21 carbons;
wherein R 2 is selected from the group consisting of hydrogen, methyl, isopropyl, isobutyl, sec butyl, acetylamide, propylamide, butyl-1-amine, and 1-butylguanidine.