Ascorbate 2-polyphosphate esters and method of making same

Details Ascorbate 2-polyphosphate esters and method of making same Ascorbate 2-polyphosphate esters and method of making same

C - Chemistry, Metallurgy

07

F

260/361.3

C07F 9/09 (2006.01) C07F 9/655 (2006.01)

Patent

CA 1246593

Abstract of the Disclosure A new stable derivative of ascorbic acid, ascorbate 2-polyphosphate, Is disclosed, together with a high-yield method of synthesis thereof. The method preferably includes steps of reacting an ascorbic acid such as L-ascorbic acid or a deriva- tive thereof such as 5,6-0-isopropylidene-L-ascor- bic acid with salts of metaphosphoric acid in an aqueous system and in the presence of sufficient base to maintain the pH of the reaction mixture at a level of at least above 9 to obtain 2-polyphos- phorylation of the ascorbic acid. In particularly preferred forms, 1 M L-ascorbic acid is reacted in water with 1.5-3 equivalents of sodium or potassium trimetaphosphate at a temperature of 25-55°C, and an alkali metal hydroxide such as potassium hydrox- ide is intermittently added to the reaction mixture as needed over a 1-10hr. reaction period to main- tain the pH thereof at a level of about 10.5-12 during the entire reaction. After neutralization the reaction mixture contains no noxious or toxic materials, and the entire mixture may be added to food or feed. Pure salts of ascorbate 2-triphos- phate can be isolated readily using conventional chromatographic techniques. It has also been found that the compounds of the invention are more diffi- cult to oxidize, and release ascorbic acid and are more slowly hydrolyzed than the monophosphate derivative of ascorbic acid.

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