Sweetener compositions and uses thereof

Abstract

The present invention provides compositions containing one or more aspartyl dipeptide derivatives represented by formulas (1) and/or (2) mixed with another high intensity sweetner, such Aspartame, sugar, sugar alcohol, and oligosaccharide; food, beverages, and/or medicinal products containing these compositions, methods of using the compositions to impart sweetness in food, beverages, and/or medicinal products to impart sweetness or suppress a bitter taste; and methods of making the compositions and products.

What is claimed is:  
     
         1 . A composition, comprising an aspartyl dipeptide ester compond represented by formula (1) or a salt thereof; and another high intensity sweetener in an amount sufficient to improve the quality of the sweetness of said aspartyl dipeptide ester compound:  
       
         
           
           
               
               
           
         
       
       wherein R 1 , R 2 , R 3 , R 4  and R 5  are independently selected from the group consisting of a hydrogen atom, a hydroxyl group, a methoxy group and a methyl group, and R 6  and R 7  are independently a hydrogen atom or a methyl group, 
 and when R 6  and R 7  are different substituents, the carbon atom to which these substituents are linked is in the (R), (S) or (RS) configuration.  
 
     
     
         2 . The composition as defined in  claim 1 , wherein the sweetness intensity of said aspartyl dipeptide ester compound is more than 4,000 times that of sucrose.  
     
     
         3 . The composition as defined in  claim 2 , wherein R 3  is a hydroxyl group or a methoxy group; and R 4  and R 5  are hydrogen atoms.  
     
     
         4 . The composition as defined in  claim 3 , wherein R 1  is a hydroxyl group.  
     
     
         5 . The composition as defined in  claim 3 , wherein R 1  is a hydrogen atom.  
     
     
         6 . The composition as defined in  claim 4 , wherein R 2 , R 6  and R 7  are hydrogen atoms.  
     
     
         7 . The composition as defined in  claim 5 , wherein R 2  is a hydrogen atom, a hydroxyl group or a methyl group.  
     
     
         8 . The composition as defined in  claim 1 , wherein the aspartyl dipeptide ester compound is selected from the group consisting of: (1) a compound wherein R 1 , R 4 , R 5 , R 6 , and R 7  are hydrogen, R 2  is OH, R 3  is OCH 3 ; (2) a compound wherein R 1 , R 2 , R 4 , R 5 , R 6 , and R 7  are hydrogen, R 3  is OCH 3 ; (3) a compound wherein R 1 , R 4 , and R 5 , are hydrogen, R 2  is OH, R 3  is OCH 3 , R 6  and R 7  are CH 3 ; (4) a compound wherein R 1 , R 4 , and R 5  are hydrogen, R 2  is CH 3 , R 3  is OH, R 6  and R 7  are CH 3 ; (5) a compound wherein R 1 , R 2 , R 4 , and R 5  are hydrogen, R 3  is a OCH 3 , R 6  and R 7  is CH 3 ; (6) a compound wherein R 1 , R 2 , R 4 , and R 5  are hydrogen, R 3  is OH, R 6  and R 7  is CH 3 ; (7) a compound wherein R 1  is OH, R 2 , R 4 , R 5 , R 6  and R 7  are hydrogen, R 3  is a OCH 3 ; (8) a compound wherein R 1 , R 4 , R 5 , R 6 , and R 7  are hydrogen, R 2  is a CH 3 , R 3  is OH; and (9) a compound wherein R 1  and R 3  are OH, R 2 , R 4 , R 5 , R 6  and R 7  are hydrogen.  
     
     
         9 . The composition as defined in  claim 8 , wherein the aspartyl dipeptide ester compound is a compound wherein R 1 , R 2 , R 4 , R 5 , R 6 , and R 7  are hydrogen and said another high intensity sweetener is Aspartame, wherein the ratio of said Aspartame to the total amount of said compound is from 25 to 99.7% by weight.  
     
     
         10 . The composition as defined in  claim 1 , wherein said another high intensity sweetener is at least one sweetener selected from the group consisting of Aspartame, Acesulfame K, Saccharine, a salt of Saccharine, Sodium cyclamate, sucralose, disodium glycyrrhizinate, Alitame, Glycyrrhizin, a Stevioside compound, and Thaumatin.  
     
     
         11 . The composition as defined in  claim 1 , wherein said another high intensity sweetener is Aspartame.  
     
     
         12 . The composition as defined in  claim 11 , wherein said Aspartame is in an amount of from 5 to 90% by sweetness intensity, relative to a total amount of the aspartyl dipeptide ester derivative.  
     
     
         13 . The composition as defined in  claim 1 , wherein said aspartyl dipeptide ester is in an amount of from 1 to 99.9% by weight.  
     
     
         14 . A product in need of sweetening, comprising the composition as defined in  claim 1  in an amount to sweeten said product.  
     
     
         15 . The product as defined in  claim 14 , which is selected from the group consisting of a food, a beverage, and a medicinal product.  
     
     
         16 . The product as defined in  claim 14 , wherein said product is a cola drink.  
     
     
         17 . A method of imparting a sweet taste into a product in need of sweetening, comprising adding the composition as defined in  claim 1  to said product in an amount to impart a sweet taste into said product.  
     
     
         18 . A composition, comprising an aspartyl dipeptide ester compound represented by formula (1), or a salt thereof; and at least one compound selected from the group consisting of sugar, sugar alcohol and oligosaccharide, which in an amount sufficient to improve the quality of the sweetness of said aspartyl dipeptide ester compound:  
       
         
           
           
               
               
           
         
         wherein R 1 , R 2 , R 3 , R 4  and R 5  are independently selected from the group consisting of a hydrogen atom, a hydroxyl group, a methoxy group and a methyl group; R 6  and R 7  are independently a hydrogen atom or a methyl group;  
         and when R 6  and R 7  are different substituents, the carbon atom to which these substituents are linked are in the (R), (S) or (RS) configuration.  
       
     
     
         19 . The composition as defined in  claim 18 , wherein the sweetness intensity of said aspartyl dipeptide ester derivative is more than 4,000 times that of sucrose.  
     
     
         20 . The composition as defined in  claim 18 , wherein R 3  is a hydroxyl group or a methoxy group; and R 4  and R 5  are hydrogens.  
     
     
         21 . The composition as defined in  claim 18 , wherein R 1  is a hydroxyl group.  
     
     
         22 . The composition as defined in  claim 18 , wherein R 1  is a hydrogen atom.  
     
     
         23 . The composition as defined in  claim 18 , wherein R 2 , R 6  and R 7  are hydrogen.  
     
     
         24 . The composition as defined in  claim 18 , wherein R 2  is a hydrogen atom, a hydroxyl group or a methyl group.  
     
     
         25 . The composition as defined in  claim 18 , wherein the aspartyl dipeptide ester compound is selected from the group consisting of: (1) a compound wherein R 1 , R 4 , R 5 , R 6 , and R 7  are hydrogen, R 2  is OH, R 3  is OCH 3 ; (2) a compound wherein R 1 , R 2 , R 4 , R 5 , R 6 , and R 7  are hydrogen, R 3  is OCH 3 ; (3) a compound wherein R 1 , R 4 , and R 5 , are hydrogen, R 2  is OH, R 3  is OCH 3 , R 6  and R 7  are CH 3 ; (4) a compound wherein R 1 , R 4 , and R 5  are hydrogen, R 2  is CH 3 , R 3  is OH, R 6  and R 7  are CH 3 ; (5) a compound wherein R 1 , R 2 , R 4 , and R 5  are hydrogen, R 3  is a OCH 3 , R 6  and R 7  is CH 3 ; (6) a compound wherein R 1 , R 2 , R 4 , and R 5  are hydrogen, R 3  is OH, R 6  and R 7  is CH 3 ; (7) a compound wherein R 1  is OH, R 2 , R 4 , R 5 , R 6  and R 7  are hydrogen, R 3  is a OCH 3 ; (8) a compound wherein R 1 , R 4 , R 5 , R 6 , and R 7  are hydrogen, R 2  is a CH 3 , R 3  is OH; and (9) a compound wherein R 1  and R 3  are OH, R 2 , R 4 , R 5 , R 6  and R 7  are hydrogen.  
     
     
         26 . The composition as defined in  claim 18 , wherein said sugar is one or more sugars selected from the group consisiting of a sucrose compound, invert sugar, isomerized sugar, glucose, fructose, lactose, malt sugar, D-xylose and isomerized lactose.  
     
     
         27 . The composition as defined in  claim 18 , wherein said sugar alcohol is one or more sugar alcohols selected from the group consisting of maltitol, sorbitol, mannitol, erythritol, xylitol, lactitol, palatinit, and reduced starch sugar.  
     
     
         28 . The composition as defined in  claim 18 , wherein said oligosaccharide is selected from the group consisting of fructooligosaccharide, maltooligosaccharide, isomalto-oligosaccharide, galactooligosaccharide, soy bean oligosaccharide and lactooligosaccharide.  
     
     
         29 . The composition as defined in  claim 18 , which comprises a sugar and wherein said sugar is sucrose.  
     
     
         30 . The composition as defined in  claim 29 , wherein the sucrose is in an amount of 5 to 95% by sweetness intensity.  
     
     
         31 . The composition as defined in  claim 18 , wherein the sugar, sugar alcohol, or oligosaccharide is present in an amount of from 5 to 95% by sweetness intensity.  
     
     
         32 . The composition as defined in  claim 25 , wherein the aspartyl dipeptide ester compound is the compound (1) wherein R 1 , R 4 , R 5 , R 6 , and R 7  are hydrogen, R 2  is OH, R 3  is OCH 3 ; and which comprises a sugar, wherein the sugar is sucrose; and wherein the sucrose is in an amount of from 5 ppm to 850 ppm by weight.  
     
     
         33 . The composition as defined in  claim 25 , wherein the aspartyl dipeptide ester compound is the compound (2) wherein R 1 , R 2 , R 4 , R 5 , R 6 , and R 7  are hydrogen, R 3  is OCH 3 ; and which comprises a sugar, wherein the sugar is sucrose; and wherein the sucrose is in an amount of from 6 ppm to 4000 ppm by weight.  
     
     
         34 . The composition as defined in  claim 18 , which is a sugar alcohol and is at least one sugar alcohol selected from the group consisting of erythritol, maltitol, sorbitol and xylitol.  
     
     
         35 . The composition as defined in  claim 34 , wherein the sugar alcohol is in an amount of from 5 to 95% by sweetness intensity.  
     
     
         36 . The sweetener composition as defined in  claim 25 , wherein the aspartyl dipeptide ester compound is the compound (1) wherein R 1 , R 4 , R 5 , R 6 , and R 7  are hydrogen, R 2  is OH, R 3  is OCH 3 ; and which comprises a sugar alcohol, which is in an amount of from 1 ppm to 3000 ppm by weight.  
     
     
         37 . The composition as defined in  claim 25 , wherein the aspartyl dipeptide ester compound is the compound (2) wherein R 1 , R 2 , R 4 , R 5 , R 6 , and R 7  are hydrogen, R 3  is OCH 3 ; and which comprises a sugar alcohol, which is in an amount of from 1 ppm to 1500 ppm by weight.  
     
     
         38 . The sweetener composition as defined in  claim 18 , wherein said aspartyl dipeptide ester compound is in an amount of from 0.5 ppm to 5000 ppm by weight.  
     
     
         39 . A product in need of sweetening, comprising the composition as defined in  claim 18  in an amount to sweeten said product.  
     
     
         40 . The product as defined in  claim 39 , which is selected from the group consisting of a food, beverage, and a medicinal product.  
     
     
         41 . The product as defined in  claim 39 , wherein said product is a cola drink.  
     
     
         42 . A method of imparting a sweet taste into a product in need of sweetening, comprising adding the composition as defined in  claim 18  to said product in an amount to impart a sweet taste into said product.  
     
     
         43 . A product, which has a bitter taste, comprising an aspartyl dipeptide ester compound of the formula (1) in an amount to reduce the bitter taste compared to the bitter taste of the product that does not contain the aspartyl dipeptide ester compound:  
       
         
           
           
               
               
           
         
         wherein R 1 , R 2 , R 3 , R 4  and R 5  are independently selected from the group consisting of a hydrogen atom, a hydroxyl group, a methoxy group and a methyl group; R 6  and R 7  are independently a hydrogen atom or a methyl group;  
         and when R 6  and R 7  are different substituents, the carbon atom to which these substituents are linked is in the (R), (S) or (RS) configuration.  
       
     
     
         44 . The product as defined in  claim 43 , wherein the intensity of sweetness of said aspartyl dipeptide ester compound is more than 4,000 times that of sucrose.  
     
     
         45 . The product as defined in  claim 44 , wherein R 3  is a hydroxyl group or a methoxy group, and R 4  and R 5  are hydrogens.  
     
     
         46 . The product as defined in  claim 45 , wherein R 1  is a hydroxyl group.  
     
     
         47 . The product as defined in  claim 45 , wherein R 1  is hydrogen.  
     
     
         48 . The product as defined in  claim 45 , wherein R 2 , R 6  and R 7  are hydrogens.  
     
     
         49 . The product as defined in  claim 45 , wherein R 2  is a hydrogen, a hydroxyl group or a methyl group.  
     
     
         50 . The product as defined in  claim 43 , wherein the aspartyl dipeptide ester compound is selected from the group consisting of: (1) a compound wherein R 1 , R 4 , R 5 , R 6 , and R 7  are hydrogen, R 2  is OH, R 3  is OCH 3 ; (2) a compound wherein R 1 , R 2 , R 4 , R 5 , R 6 , and R 7  are hydrogen, R 3  is OCH 3 ; (3) a compound wherein R 1 , R 4 , and R 5 , are hydrogen, R 2  is OH, R 3  is OCH 3 , R 6  and R 7  are CH 3 ; (4) a compound wherein R 1 , R 4 , and R 5  are hydrogen, R 2  is CH 3 , R 3  is OH, R 6  and R 7  are CH 3 ; (5) a compound wherein R 1 , R 2 , R 4 , and R 5  are hydrogen, R 3  is a OCH 3 , R 6  and R 7  is CH 3 ; (6) a compound wherein R 1 , R 2 , R 4 , and R 5  are hydrogen, R 3  is OH, R 6  and R 7  is CH 3 ; (7) a compound wherein R 1  is OH, R 2 , R 4 , R 5 , R 6  and R 7  are hydrogen, R 3  is a OCH 3 ; (8) a compound wherein R 1 , R 4 , R 5 , R 6 , and R 7  are hydrogen, R 2  is a CH 3 , R 3  is OH; and (9) a compound wherein R 1  and R 3  are OH, R 2 , R 4 , R 5 , R 6  and R 7  are hydrogen.  
     
     
         51 . The product as defined in  claim 43 , which is a food, a beverage, or a medicine.  
     
     
         52 . The product as defined in  claim 43 , wherein the bitter taste is imparted on the product by one or more compounds selected from the group consisting of an amino acid, a peptide, quinine, caffeine and a mineral.  
     
     
         53 . The product as defined in  claim 51 , wherein the aspartyl dipeptide ester compound is in an amount of from 0.2 ppm to 10000 ppm by weight.  
     
     
         54 . The product as defined in  claim 47 , which is a liquid product.  
     
     
         55 . A method of correcting the taste of a product, comprising adding a aspartyl dipeptide ester of formula (1) to said product, in an amount sufficient to correct the taste of the product:  
       
         
           
           
               
               
           
         
         wherein R 1 , R 2 , R 3 , R 4  and R 5  are independently selected from the group consisting of a hydrogen atom, a hydroxyl group, a methoxy group and a methyl group; R 6  and R 7  are independently a hydrogen atom or a methyl group; and when R 6  and R 7  are different substituents, the carbon atom to which these substituents are linked is in the (R), (S) or (RS) configuration.  
       
     
     
         56 . The method as defined in  claim 55 , wherein said corrected taste is a bitter taste.