Taste-modified creatine salts, compounds, compositions and uses thereof

Inventors

Lebedyeva, Iryna • Klug, Christopher

Assignees

Augusta University • Augusta University Research Institute Inc

Abstract

Provided are embodiments of creatine and creatine ethyl ester (CEE) salts where the anion is an artificial (non-saccharide) taste-modifier. These compounds represent stable white non-hygroscopic solids or semisolids that can readily dissolve in water and buffer solutions. Synthesis of novel creatine salts using environmentally safe solvents such as ethanol resulted in the formation of products in quantitative yields with sodium or potassium chloride as a byproduct. The creatine and creatine alkyl eater derivative salts are stable sweet-tasting compounds that are more palatable to a consumer than creatine or derivatives thereof.

Core Innovation

The disclosure describes creatine salts and solvates formed by pairing creatine or a cationic derivative of creatine with an anionic taste-modifier. The creatine salts have a structure defined by formula I with substituent options R1 and R2 each independently a hydrogen or an alkyl group, R3 selected as H or an alkyl group, and X selected from saccharinate, acesulfamate, neotamate, cyclamate, steviolate, and taurocholate.

The disclosed embodiments include creatine acesulfamate, creatine saccharinate, creatine ethyl ester acesulfamate, creatine ethyl ester saccharinate, creatine taurocholate, and creatine ethyl ester taurocholate. Additional embodiments refine the substituent selection by restricting R3 and by specifying creatine alkyl ester cations including creatine ethyl ester cations.

In addition to the salts and solvates themselves, the disclosure describes compositions comprising at least one creatine salt or solvate thereof. The disclosure also describes a formulation limitation in which an aqueous medium may be present in an amount that does not dissociate the creatine salt or the cationic creatine derivative, and it characterizes the salt as having improved taste characteristics relative to creatine.

Claims Coverage

The document includes three independent claims covering a creatine salt or solvate with a defined taste-modifier anion set, a composition comprising one or more of those creatine salts or solvates with defined structural features and formulation constraints, and a creatine salt or solvate where X is taurocholate and the salt has a reduced bitter taste compared to creatine. Across the independent claims, the main inventive features are the coupling of a creatine cation or creatine-derived cation to specific anionic taste-modifiers under a formula I structural definition, optionally refined by substituent selections and by non-dissociation formulation constraints.

Overall, the claim set centers on creatine salts and solvates that couple creatine or a cationic creatine derivative to specified anionic taste-modifiers under formula I structural constraints, and on compositions containing one or more such salts or solvates. One independent claim specifically ties a taurocholate-containing creatine salt to a reduced bitter taste compared to creatine.

Stated Advantages

Documented Applications