Methods of making low odor choline salts of an organic compound

Abstract

Methods of making low odor choline salts of an organic compound, for example, choline ellagate compound(s), and uses and formulations thereof.

1 . A method of preparing at least one choline ellagate compound, the method comprising:
 (a) obtaining an ellagic acid compound;   (b) contacting a choline salt with the ellagic acid compound in a liquid at a pH of 6.95 to 8 and an environment with reduced oxygen to form a liquid suspension containing at least one choline ellagate compound;   (c) cooling the liquid suspension of step (b) to 25° C. or below;   (d) isolating at least one of the choline ellagate compound(s) from the liquid suspension; and   (e) drying the isolated choline ellagate compound(s).   
     
     
         2 . The method of  claim 1 , wherein the ellagic acid compound is ellagic acid dihydrate and/or ellagic acid. 
     
     
         3 . The method of  claim 1 , wherein step (c) further comprises cooling the liquid suspension in the dark and protected from moisture and oxygen for at least 5 hours. 
     
     
         4 . The method of  claim 1 , wherein the contacting in step (b) increases in temperature to a temperature sufficient to dissolve the ellagic acid compound and form the at least one choline ellagate compound. 
     
     
         5 . The method of  claim 1 , wherein step (d) isolation further comprises:
 (i) filtering the liquid suspension to obtain a choline ellagate compound(s) precipitate and a liquid filtrate, wherein the liquid filtrate comprises additional dissolved choline ellagate compound(s); and   (ii) washing the choline ellagate compound(s) precipitate with cold ethanol.   
     
     
         6 . The method of  claim 5 , wherein step (d) further comprises:
 (iii) forming an alcoholic solution comprising the liquid filtrate, the ethanolic wash, or both;   (iv) isolating additional dissolved choline ellagate compound(s) from the alcoholic solution; and   (v) drying the isolated choline ellagate compound(s).   
     
     
         7 . The method of  claim 6 , wherein step (iv) comprises:
 (iv.1) reducing the volume of the alcoholic solution;   (iv.2) cooling the reduced alcoholic solution to a temperature sufficient to precipitate the additional dissolved choline ellagate compound(s) from the solution;   (iv.3) isolating the additional choline ellagate compound(s); and   (iv.4) drying the isolated choline ellagate compound(s).   
     
     
         8 . The method of  claim 1 , wherein the liquid is a solvent for the choline salt and/or the ellagic acid compound. 
     
     
         9 . The method of  claim 1 , wherein the liquid comprises water, methanol, or ethanol, or a combination thereof. 
     
     
         10 . The method of  claim 1 , wherein the choline salt is a hydroxide salt of choline. 
     
     
         11 . The method of  claim 1 , wherein the dried isolated choline ellagate compound(s) are substantially devoid of free amine and/or trimethylamine. 
     
     
         12 . The method of  claim 1 , wherein the dried isolated choline ellagate compound(s) has a low odor or is odorless. 
     
     
         13 . A choline ellagate compound formed by the method of  claim 1 . 
     
     
         14 . A method of preparing a choline salt of an organic compound composition, the method comprising:
 (a) obtaining an organic compound capable of interacting with choline;   (b) contacting a choline salt with the organic compound in a liquid under a reduced oxygen atmosphere and a pH of 6.95 to 8 to form a liquid suspension comprising a choline salt of the organic compound;   (c) cooling the liquid suspension of step (b) to a 25° C. to −80° C.;   (d) isolating the choline salt of the organic compound from the liquid suspension; and   (e) drying the isolated choline salt of the organic compound.   
     
     
         15 . The method of  claim 14 , wherein the organic compound is a phytochemical compound. 
     
     
         16 . The method of  claim 15 , wherein the phytochemical compound is a phenolic compound. 
     
     
         17 . The method of  claim 14 , wherein the choline salt is a hydroxide salt of choline. 
     
     
         18 . A choline salt of an organic compound formed by the method of  claim 14 .