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(12) Patent Application Publication (10) Pub. No.: US 2008/0292765 A1 Prakash Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2008/0292765 A1 Prakash Et Al US 20080292765A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2008/0292765 A1 Prakash et al. (43) Pub. Date: Nov. 27, 2008 (54) SWEETNESSENHANCERS, SWEETNESS (22) Filed: May 15, 2008 ENHANCED SWEETENER COMPOSITIONS, METHODS FOR THEIR FORMULATION, Related U.S. Application Data AND USES (60) Provisional application No. 60/939,554, filed on May (75) Inventors: Indra Prakash, Alpharetta, GA 22, 2007. (US); Grant E. DuBois, Roswell, GA (US); George A. King, Atlanta, Publication Classification GA (US); Mani Upreti, Dunwoody, GA (US); Josef Klucik, Marietta, (51) Int. Cl. GA (US); Rafael I. San Miguel, A2.3L I/236 (2006.01) Atlanta, GA (US) (52) U.S. Cl. ........................................................ 426/548 Correspondence Address: SUTHERLAND ASBLL & BRENNAN LLP (57) ABSTRACT 999 PEACHTREE STREET, N.E. ATLANTA, GA 30309 (US) The present invention relates generally to Sweetness enhanc ers capable of enhancing the Sweet taste of Sweetener com (73) Assignee: THE COCA-COLACOMPANY., positions and the Sweetener compositions produced there Atlanta, GA (US) from. In particular, the present invention relates to Sweetener compositions comprising Sulfamates capable of enhancing (21) Appl. No.: 12/120,874 the Sweetness of the Sweetener composition. Patent Application Publication Nov. 27, 2008 Sheet 1 of 5 US 2008/0292765 A1 96) 640 30 Patent Application Publication Nov. 27, 2008 Sheet 2 of 5 US 2008/0292765 A1 300 Fig. 2 Patent Application Publication Nov. 27, 2008 Sheet 3 of 5 US 2008/0292765 A1 2400 O) 3. 800 Fig. 3 Patent Application Publication Nov. 27, 2008 Sheet 4 of 5 US 2008/0292765 A1 6) S 800 Fig. 4 Patent Application Publication Nov. 27, 2008 Sheet 5 of 5 US 2008/0292765 A1 US 2008/0292765 A1 Nov. 27, 2008 SWEETNESS ENHANCERS, SWEETNESS ENHANCED SWEETENER COMPOSITIONS, METHODS FOR THEIR FORMULATION, O| /R AND USES OES-N V CROSS-REFERENCE TO RELATED ÓR R2 APPLICATIONS 0001. The present application claims priority under 35 wherein R and R2, independent of one another, comprise a U.S.C. S 119(c) to U.S. Provisional Application No. 60/939, hydrogen, alkoxy, aryloxy, nitro, acyl, cyano, thioester, thio 554, filed on May 22, 2007, the disclosure of which is hereby ether, or a straight chained, branched, or cyclic alkyl alkenyl, incorporated by reference in its entirety. alkynyl, aryl, heteroaryl, or heterocyclic group; wherein R comprises any alkali or alkaline earth metal, hydrogen, or a FIELD OF THE INVENTION straight chained, branched, or cyclic alkyl, alkenyl, alkynyl. aryl, heteroaryl, or heterocyclic group; wherein both R and 0002. The present invention relates to sweeteners having R, may be incorporated into a substituted or an unsubstituted enhanced sweetness. In particular, the present invention heteroaryl or heterocyclic group; and wherein both R- and R relates to use of sulfamate analogues as Sweetness enhancers may be incorporated into a substituted or an unsubstituted and/or taste modulators. heteroaryl or heterocyclic group. The functional groups or moieties of R. R. and R may optionally be substituted with BACKGROUND OF THE INVENTION one or more moities. Non-limiting examples of such moieties include hydrogen, hydroxyl, halogen, haloalkyl, carboxyl, 0003. Although natural caloric sweetener compositions acyl, acyloxy, amino, amido, carboxyl derivatives, alky such as sucrose, fructose, and glucose taste good to most lamino, dialkylamino, arylamino, alkoxy, aryloxy, nitro. consumers, they are caloric. Therefore, alternative non-ca cyano, sulfo, mercapto, imino, sulfonyl, Sulfenyl, sulfinyl. loric or low-caloric sweeteners have been used widely as sulfamoyl carboalkoxy, carboxamido, phosphonyl, phosphi sugar or sucrose substitutes. Many non-caloric or low-caloric nyl, phosphoryl, phosphino, thioester, thioether, oximino, sweeteners, however, are prohibitively expensive. Thus, it hydrazino, carbamyl, phospho, phosphonato, substituted or may be desirable to identify compounds capable of enhancing unsubstituted straight, branched, cyclic, alkyl, alkynl, alk or increasing the perception of Sweetness of such Sweeteners. enyl, aryl, heteroaryl, or heterocyclic group, or any other By combining such compounds with Sweeteners, the amount viable functional groups or moieties known to those of ordi of Sweetener needed to obtain a desired degree of Sweetness nary skill in the art. may be reduced significantly, thereby reducing the calories 0006. The sweetness enhancer may be combined with any imparted by natural caloric Sweeteners or reducing the suitable sweetener to provide a Sweetener composition hav amounts of low-caloric or non-caloric natural or synthetic ing enhanced sweetness. In another embodiment, the Sweet high-potency Sweeteners. ener composition may further comprise at least one Sweet 0004. It is well known to those skilled in the art of food/ taste improving composition. beverage formulation, however, that changing the Sweetener 0007. Other embodiments described herein provide in a composition requires re-balancing of the flavor and other sweetened compositions comprising at least one Sweetener taste components (e.g., acidulants). For example, the Sweet and at least one sweetness enhancer comprising a sulfamate, ness enhanced sweet tastes of natural caloric Sweeteners and methods for enhancing the Sweetness of Sweetener composi alternative non-caloric or low-caloric Sweeteners may be tions by combining a sweetener with a Sweetness enhancer slower in onset and longer in duration than the Sweet taste comprising a sulfamate, and methods for enhancing the produced by sugar and thus change the taste balance of a food sweetness of sweetened composition by combining a Sweet composition. In addition, sweetness enhanced sweet tastes of enable composition with a Sweetener and a Sweetness natural caloric sweeteners and alternative non-caloric or low enhancer comprising a sulfamate. caloric sweeteners may exhibit (i) lower maximal response 0008 Objects and advantages of the invention will be set than sugar, (ii) off tastes including bitter, metallic, cooling. forth in part in the following description, or may be obvious astringent, licorice-like taste, etc., and/or (iii) Sweetness from the description, or may be learned through practice of which diminishes on iterative tasting. If the taste profile of the invention. Unless otherwise defined, all technical and sweetness enhanced sweetener compositions could be modi scientific terms and abbreviations used herein have the same fied to impart specific desired taste characteristics to be more meaning as commonly understood by one of ordinary skill in sugar-like, the type and variety of compositions that may be the art to which this invention pertains. Although methods and prepared with that sweetness enhanced sweetener may be compositions similar or equivalent to those described herein expanded significantly. Accordingly, it may be desirable to can be used in the practice of the present invention, Suitable selectively modify the taste characteristics of Sweetness methods and compositions are described without intending enhanced sweetener compositions. that any such methods and compositions limit the invention herein. SUMMARY OF THE INVENTION BRIEF DESCRIPTION OF THE DRAWINGS 0005 Generally, this invention addresses the above-de scribed need by providing a Sweetness enhancer comprising a 0009 FIG. 1 is a powder X-ray diffraction scan of rebau sulfamate analogue for enhancing Sweetness. In a particular dioside A polymorph Form 1 on a plot of the scattering embodiment, the sweetness enhancer comprises a sulfamate intensity versus the scattering angle 20 in accordance with an having the chemical formula: embodiment of this invention. US 2008/0292765 A1 Nov. 27, 2008 0010 FIG. 2 is a powder X-ray diffraction scan of rebau HNSO, and is synonymous with the phrases amidosulfonic dioside A polymorph Form 2 on a plot of the scattering acid, amidosulfuric acid, aminosulfonic acid, and Sulfamidic intensity versus the scattering angle 20 in accordance with an acid. embodiment of this invention. 0018. In a particular embodiment, the sulfamate has the 0011 FIG. 3 is a powder X-ray diffraction scan of rebau chemical structure of Formula I: dioside A polymorph Form 3A on a plot of the scattering intensity versus the scattering angle 20 in accordance with an embodiment of this invention. (I) O| /R 0012 FIG. 4 is a powder X-ray diffraction scan of rebau OES-N dioside A polymorph Form 3B on a plot of the scattering V intensity versus the scattering angle 20 in accordance with an ÓR R2 embodiment of this invention. 0013 FIG. 5 is a powder X-ray diffraction scan of rebau dioside A polymorph Form 4 on a plot of the scattering wherein R and R, independent of one another, comprise a intensity versus the scattering angle 20 in accordance with an hydrogen, alkoxy, aryloxy, nitro, acyl, cyano, thioester, thio embodiment of this invention. ether, or a straight chained, branched, or cyclic alkyl, alkenyl, alkynyl, aryl, heteroaryl, or heterocyclic group; wherein R comprises any alkali or alkaline earth metal, hydrogen, or a DETAILED DESCRIPTION OF THE straight chained, branched, or cyclic alkyl, alkenyl, alkynyl, EMBODIMENTS aryl, heteroaryl, or heterocyclic group; wherein both R and R, may be incorporated into a substituted or an unsubstituted 0014 Reference now will be made in detail to the pres heteroaryl or heterocyclic group; and wherein both R- and R ently proffered embodiments of the invention. Each example may be incorporated into a substituted or an unsubstituted is provided
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