# Patent

## Title
Sweetener

## Abstract

A low calorie sweetener composition with sweetness synergy, providing a reduction in off-taste and a desirable temporal profile. The sweetener composition is suitable for use as a substitute for high calorie sugars. The sweetener composition is for use in food and beverage products, pharmaceutical products, nutritional product and cosmetic products.

## Background
CROSS REFERENCE TO RELATED APPLICATION
This application claims priority to U.S. Provisional Application No. 61/793,469 filed Mar. 15, 2013, which is incorporated herein by reference in its entirety for all purposes.


FIELD OF THE INVENTION
The present invention relates to a low calorie sweetener composition having sweetness synergy. The present invention also relates to food or beverage products comprising said sweetener composition.
BACKGROUND OF THE INVENTION
Many food and beverage products contain nutritive sweeteners such as sucrose (generally referred to as ‘sugar’ or ‘table sugar’), glucose, fructose, corn syrup, high fructose corn syrup and the like. Such sweeteners supply not only sweetness to the food and beverage products, but also bulk, texture and desirable functional properties such as browning, humectancy, freezing point depression and the like. They also produce a favorable sensory response, for example in terms of quality of sweetness, lack of bitterness and off taste, desirable temporal profile and desirable mouthfeel.
Although desirable in terms of taste and functional properties, excess intake of nutritive sweeteners, such as sucrose, has long been associated with an increase in diet-related health issues, such as obesity, heart disease, metabolic disorders and dental problems. This worrying trend has caused consumers to become increasingly aware of the importance of adopting a healthier lifestyle and reducing the level of nutritive sweeteners in their diet.
In recent years, there has been a movement towards the development of replacements for nutritive sweeteners, with a particular focus on the development of low or zero-calorie sweeteners. An ideal replacement for a nutritive sweetener is a sweetener that has the same desirable taste characteristics and functional properties as the nutritive sweetener, but which also has fewer calories. Aiming to meet this growing need, the market has been flooded with possible candidates to replace conventional nutritive sweeteners. Unfortunately, however, many of the low or zero calorie replacements offered on the market lack one or all of the necessary characteristics, and often exhibit bitterness or off-taste. Therefore, many of the proposed sweeteners are not an ideal replacement for nutritive sweeteners.
One proposed alternative to nutritive sweeteners is allulose (also known as D-psicose). Allulose is known as a “rare sugar”, since it occurs in nature in only very small amounts. It provides around 70% of the sweetness of sucrose, but only around 5% of the calories (approximately 0.2 kcal/g). It may therefore essentially be considered to be a ‘zero’ calorie sweetener.
In view of its scarcity in nature, production of allulose relies on the epimerization of readily available fructose. Ketose-3-epimerases can interconvert fructose and allulose, and various ketose-3-epimerases are known for carrying out this conversion.
U.S. Pat. No. 8,030,035 and PCT Publication No. WO2011/040708 disclose that D-psicose (an alternative name for allulose) can be produced by reacting D-fructose with a protein derived from Agrobacterium tumefaciens, and having psicose 3-epimerase activity.
US Patent Publication No. 2011/0275138 discloses a ketose 3-epimerase derived from a microorganism of the Rhizobium genus. This protein shows a high specificity to D- or L-ketopentose and D- or L-ketohexose, and especially to D-fructose and D-psicose. This document also discloses a process for producing ketoses by using the protein.
Korean Patent No. 100832339 discloses a Sinorhizobium YB-58 strain which is capable of converting fructose into psicose (i.e. allulose), and a method of producing psicose using a fungus body of the Sinorhizobium YB-58 strain.
Korean Patent Application No. 1020090098938 discloses a method of producing psicose using E. coli wherein the E. coli expresses a polynucleotide encoding a psicose 3-epimerase.
Allulose is present in processed cane and beet molasses, steam-treated coffee, wheat plant products and high fructose corn syrup. D-allulose is the C-3 epimer of D-fructose and the structural differences between allulose and fructose result in allulose not being metabolized by the human body to any significant extent, and thus having “zero” calories. Thus, allulose is thought to be a promising candidate as a replacement for nutritive sweeteners and as a sweet bulking agent, as it has no calories and is reported to be sweet while maintaining similar properties to sucrose.
Alternative sweeteners on the market include acesulfame (Ace K) and fructose. Acesulfame K (Ace K) is a ‘high potency’ or ‘high intensity’ sweetener that is approximately 200 times sweeter than sucrose.
Fructose (also known as “fruit sugar”) is a 6-carbon polyhydroxyketone monosaccharide sugar that is often found in plants and in honey. The monosaccharide is found in crystalline form, often referred to as D-fructose. Fructose can also be found as a component of other sweeteners such as high-fructose corn syrup (HFCS) which is a mixture of glucose and fructose. Fructose is frequently used to enhance the sweetness and taste of food and beverage products.
However, the use of allulose alone as a table sugar substitute may have some limitations due to cost and digestive tolerance in some applications. Furthermore, when used alone, AceK has been shown to exhibit a metallic aftertaste and an undesirable temporal profile. In addition, using fructose as a replacement for sucrose and other nutritive sweeteners also has its limitations, as fructose is fully caloric and thus does not provide an effective calorie reduction strategy.
Therefore, there is a need to provide an improved replacement for nutritive sweeteners that has low or zero-calories and is without limitations in use, but which also has taste characteristics and functional properties similar to those of sucrose and other nutritive sweeteners.
SUMMARY OF THE INVENTION
The present invention seeks to provide a solution to the above mentioned problem by providing a sweetener composition having taste characteristics comparable to sucrose but having low calories. Advantageously, the present invention also seeks to provide a sweetener composition having sweetness synergy, a reduction in off-taste or off-flavor, a desirable temporal profile and improved mouthfeel, compared with proposed sweeteners currently available on the market.
A first aspect of the present invention provides a sweetener composition comprising allulose, acesulfame K (Ace K) and fructose.
According to an embodiment, the sweetener composition comprises allulose in an amount of about 40% to about 80%, Ace K in an amount of about 0.1% to about 0.2% and fructose in an amount of about 20% to about 60% by weight relative to the total weight of the composition.
According to another embodiment, the sweetener composition comprises allulose in an amount of about 77.3%, Ace K in an amount of about 0.14%, and fructose in an amount of about 22.56% by weight relative to the total weight of the composition.
Alternatively, the sweetener composition comprises allulose in an amount of about 44.4%, Ace K in an amount of about 0.16%, and fructose in an amount of about 55.44% by weight relative to the total weight of the composition.
In some embodiments, the sweetener composition further comprises a sweet taste improving additive, a bulking agent, a flavoring agent, and/or a stabilizer.
A further aspect of the present invention provides a food or beverage product, comprising a sweetener composition of the invention.
A further aspect of the present invention provides a table-top sweetener comprising a sweetener composition of the invention.
Further aspects of the present invention provide a bulking agent comprising a sweetener composition according to the invention; a coating agent comprising a sweetener composition according to the invention; a cosmetic product comprising a sweetener composition according to the invention; a pharmaceutical product comprising a sweetener composition according to the invention; a nutritional product comprising a sweetener composition according to the invention; and a sports product comprising a sweetener composition according to the invention.
Another aspect of the present invention provides the use of a sweetener composition according to the present invention in a food product, a beverage product, a pharmaceutical product, a nutritional product, a sports product, or a cosmetic product. Another aspect of the present invention provides the use of the sweetener composition according to the present invention as a bulking agent. Another aspect of the present invention provides the use of the sweetener composition according to the present invention as a coating agent.



DETAILED DESCRIPTION OF THE FIGURES
FIG. 1: Graph illustrating the Mean SEV for allulose, Ace K and fructose and a composition comprising allulose, Ace K and fructose.



DETAILED DESCRIPTION OF THE INVENTION
The present invention is based on the surprising finding that allulose, Ace K and fructose exhibit sweetness synergy, whereby the blend is sweeter than the expected sweetness based on the sweetness of its components. That is to say, the relative sweetness of the sweetener composition is greater than the sweetness calculated from the individual components of the composition.
Furthermore, it has been found that this blend of allulose, Ace K and fructose addresses problems associated with the individual components, in particular, with regard to the metallic taste and/or undesirable temporal profile that may be associated with Ace K alone. In addition, due to the presence of the zero calorie sweeteners, allulose and Ace K the sweetener composition is low calorie. Furthermore, as a consequence of the sweetness synergy exhibited by the composition, the amount of the composition required to provide a given level of sweetness is less than would be expected in the absence of synergy, thereby allowing a further reduction in calories. Thus, the sweetener composition of the present invention provides enhanced sweetness, improves the balance of flavor by reducing off-taste, and provides a more desirable temporal profile, while at the same time allowing a significant reduction in calories compared to a sweet-equivalent amount of a conventional nutritive sweetener.
Using the sweetener composition of the present invention allows delivery of an increased sweetness in food or beverage products when compared to the individual components used separately. This enhanced sweetness means that a smaller amount of sweetener can be used in these products, to provide a temporal and taste profile that closely matches that of sucrose, with the benefits of allulose, such as better overall acceptability, mouthfeel, reduced off-taste, desirable temporal profile, while being cost effective and reducing the likelihood of digestive tolerance issues.
In general terms, the present invention relates to a sweetener composition comprising the sweeteners allulose, Ace K, and fructose.
The term “allulose” as used herein refers to a monosaccharide sugar of the structure shown as a Fischer projection in below Formula I. It is also known as “D-psicose”:




The term “fructose” as used herein refers to the monosaccharide sugar of the structure shown as a Fischer projection in below Formula II:




Acesulfame is an artificial sweetener also known as acesulfame potassium or Ace K. Acesulfame is the potassium salt of 6-methyl-1,2,3-oxathiazine-4(3H)-one 2,2-dioxide and has the structure shown in Formula III:




The term “temporal profile” of a composition, sugar or sweetener, as used herein, is a measure of the perceived sweetness intensity of said composition, sugar or sweetener over time. A desirable or advantageous temporal profile is one wherein sweetness is observed quickly and has a short linger similar to that of sucrose.
The term “sucrose equivalent value” or “SEV” as used herein refers to the sweetness equivalent of a sweetener related to the sweetness of sucrose. For example, a sweetener at an SEV value of 5 would have a sweetness similar to a 5% by weight solution of sucrose.
The term “low calorie” as used herein refers to a sweetener having 40 calories or fewer per reference amount customarily consumed (RACC) and per labeled serving.
All amounts given in % by weight are quoted on a dry solids (ds) basis unless specifically stated otherwise. Thus, where components are provided other than in their pure form, the amount added should be adjusted to provide the required amount on a dry solids basis. For example, where allulose is provided as a syrup, the amount of syrup used should be adjusted to supply the required amount of allulose on a dry solids basis.
The present invention provides a sweetener composition comprising allulose, fructose and Ace K.
According to an embodiment of the present invention, the sweetener composition comprises allulose in an amount of about 40% to about 80%, Ace K in an amount of about 0.1% to about 0.2% and fructose in an amount of about 20% to about 60% by weight relative to the total weight of the composition.
Preferably, the sweetener composition of the invention comprises allulose in an amount of about 40%, 41%, 42%, 43%, 44%, 45%, 46%, 47%, 48%, 49%, 50%, 51%, 52%, 53%, 54%, 55%, 56%, 57%, 58%, 59%, 60%, 61%, 62%, 63%, 64%, 65%, 66%, 67%, 68%, 69%, 70%, 71%, 72%, 73%, 74%, 75%, 76%, 77%, 78%, 79% or 80%, Ace K in an amount of about 0.10%, 0.11%, 0.12%, 0.13%, 0.14%, 0.15%, 0.16%, 0.17%, 0.18%, 0.19%, or 0.20% and fructose in an amount of about 20%, 21%, 22%, 23%, 24%, 25%, 26%, 27%, 28%, 29%, 30%, 31%, 32%, 33%, 34%, 35%, 36%, 37%, 38%, 39%, 40%, 41%, 42%, 43%, 44%, 45%, 46%, 47%, 48%, 49%, 50%, 51%, 52%, 53%, 54%, 55%, 56%, 57%, 58%, 59%, or 60%, by weight relative to the total weight of the composition.
In a preferred embodiment of the present invention, the sweetener composition comprises allulose in an amount of about 77.3% (preferably, about 65% to about 80%, or about 75% to about 79%), Ace K in an amount of about 0.14% (preferably, 0.1% to about 0.8%, preferably 0.12% to about 0.16%), and fructose in an amount of about 22.56% (preferably, about 20% to about 35%, preferably, 21% to about 25%) by weight relative to the total weight of the composition. In an alternative embodiment, the sweetener composition comprises allulose in an amount of about 44.4% (preferably, about 40% to about 55%, preferably, about 42% to about 47%), Ace K in an amount of about 0.16% (preferably, about 0.11% to about 0.19%, preferably, 0.13% to about 0.17%) and fructose in an amount of about 55.44% (preferably, about 45% to about 60%, preferably about 52% to about 57%) by weight relative to the total weight of the composition.
Advantageously, the sweetener composition comprises allulose in an amount of about 25%, Ace K in an amount of about 25% and fructose in an amount of about 50% (by percentage of added sweetness in terms of relative sugar equivalent value (SEV)). In an alternative embodiment, the sweetener composition comprises allulose in an amount of about 50%, Ace K in an amount of about 25%, and fructose in an amount of about 25% (by percentage of added sweetness in terms of relative sugar equivalent value (SEV)).
In some embodiments, the sweetener composition may further comprise a sweet taste improving additive, a bulking agent, a flavoring agent, and/or a stabilizer.
A further aspect of the present invention provides a food product comprising the sweetener composition of the invention. Non-limiting examples of a food product include a confectionary product, a dessert product such as yogurt, ice-cream, biscuits, and cakes, a cereal product, baked goods, frozen dairy products, meats, dairy products, condiments, snack bars, soups, dressings, mixes, prepared foods, baby foods, diet preparations, syrups, food coatings, dried fruit, sauces, gravies, jams/jellies, and the like, especially those which are reduced sugar or low sugar products. The food product may be an animal feed product. The food product of the invention may comprise a sweetener composition as a coating or frosting formed on the surface of the product. A coating improves the flavor of the food product as well as its shelf life.
Another aspect of the invention provides a beverage product comprising a sweetener composition of the present invention. Non-limiting examples of a beverage product include a carbonated beverage, a non-carbonated beverage, fruit-flavored beverage, fruit-juice, tea, milk, coffee especially those which are reduced sugar or low sugar products.
A further aspect of the present invention provides a table-top sweetener comprising a sweetener composition according to the invention.
Another aspect of the present invention provides a bulking agent comprising a sweetener composition according to the invention.
Another aspect of the present invention provides a coating agent comprising a sweetener composition according to the invention.
Another aspect of the present invention provides a pharmaceutical product comprising a sweetener composition according to the invention.
Another aspect of the present invention provides a nutritional or sports product comprising a sweetener composition according to the invention.
Another aspect of the present invention provides a cosmetic product comprising a sweetener composition according to the invention.
It will be appreciated that the amount of a sweetener composition according to the invention present in a food product, a beverage product, a pharmaceutical product, a nutritional product, a sports product, or a cosmetic product, will depend upon the type and amount of sweetener present in the sweetener composition and the desired sweetness of the food or beverage product.
An alternative aspect of the present invention provides the use of a sweetener composition according to the invention in a food product, a beverage product, a pharmaceutical product, a nutritional product, a sports product, or a cosmetic product, as a bulking agent or as a coating agent.
The sweetener composition may be formulated in any ingestible form, for example, as a syrup, in powder form, tablet form, as granules, in a solution or in any other suitable form including beverages and food products.
As outlined in the below examples, the sweetener composition of the invention exhibits a sucrose equivalent value (SEV) greater than the predicted value based on its individual components. Therefore, the sweetener composition of the present invention displays sweetness synergy.
The following example is exemplary only and is not intended to be limiting in any way.
Example
Demonstration of Sweetness Synergy of the Composition of the Present Invention
Round table evaluations were performed with test panelists. Equal sweet 10 SEV concentrations in neutral pH water were made for allulose, AceK and fructose, as well as a composition comprising allulose, AceK and fructose. The components of the test compositions are described in the below tables. The mixed compositions were calculated using the Beidler mixture equation for the sweeteners. The Beidler mixture equation for sweeteners is as follows:




  SEV
  =
  
    
      conc
      ·
      
        R
        
          ma
          ⁢
          
            
          
          ⁢
          x
        
      
    
    
      conc
      +
      
        1
        /
        K
      
    
  




The concentration of each component in the mixture in ppm is divided by SEV (c/R) and is plotted against concentration, c. The slope of the linear regression is the maximum SEV (Rmax). The y-intercept of the linear regression multiplied by Rmax is the half-maximal sweetness concentration, 1/K. Rmax and 1/K are the two parameters used in the Beidler equation
The equal-molar mixture was tested against reference samples for the panelists to determine SEV values. References samples were 4%, 6%, 8%, 10%, 12%, and 14% sucrose in neutral pH water. The test samples were served in 2 ounce soufflé cups (approximately 60 ml) coded with 3-digit codes at room temperature. A two minute wait period between samples was enforced. Water and unsalted crackers was available for the panelists to clear their palates before and during testing. EyeQuestion, software distributed by Logic8 BV of Elst, The Netherlands, was used for ballot development and recording of results. Results were collected in EyeQuestion for calculating approximate SEV level of each test sample.
The test products analyzed in this experiment are described below in Table 1.
Product Information















TABLE 1






Allulose
Allulose
AceK
AceK SEV
Fructose
Fructose
Allulose/AceK/
Allulose/AceK/



10%
10%
SEV 10
10
SEV 10
SEV 10
Fructose
Fructose


INGREDIENT
%
GRAMS
%
GRAMS
%
GRAMS
%
GRAMS























Allulose
17.02
40.848
0
0
0
0
5.6733
13.616


89% DS


syrup


AceK
0
0
0.2938
0.70512
0
0
0.0979
0.23504


Fructose
0
0
0
0
8.55
20.52
2.85
6.84


RO Water
82.98
199.152
99.7062
239.29488
91.45
219.48
91.378
219.308


TOTAL
100
240
100
240
100
240
100
240









Results

FIG. 1 illustrates the mean sucrose equivalent values for a sweetener composition according to the present invention, as well as the SEV for each of the individual components of the sweetener composition.
Table 2 recites the mean and median sucrose equivalent values (SEV) for the sweetener composition, as well as the SEV for each of the individual components of the sweetener composition.












TABLE 2







Mean 1
StDev
Median 1
1 STDEV




















AceK
9.285714
2.9277
8
1.46385


Fructose
10.14286
1.214986
10
0.607493


Allulose
10.14286
1.46385
10
0.731925


Allulose/AceK/Fructose
12.71429
2.13809
12
1.069045









The sweetener composition comprising allulose, Ace K and fructose was significantly higher in sweetness than all of the three components at a 95% confidence level.
CONCLUSION
A sweetener composition according to the present invention exhibits a statistically significant sweetness synergy.
Although the invention is illustrated and described herein with reference to specific embodiments, the invention is not intended to be limited to the details shown. Rather, various modifications may be made in the details within the scope and range of equivalents of the claims and without departing from the invention.

## Claims

1. A sweetener composition consisting of allulose in an amount of about 61% to about 80%, acesulfame K (Ace K) in an amount of about 0.1% to about 0.2% and fructose in an amount of about 39% to about 60% by weight relative to the total weight of the sweetener composition.

2. The sweetener composition according to claim 1, consisting of allulose in an amount of about 77.3%, Ace K in an amount of about 0.14%, and fructose in an amount of about 22.56% by weight relative to the total weight of the composition.

3. A sweetener composition consisting of allulose in an amount of about 44.4%, Ace K in an amount of about 0.16%, and fructose in an amount of about 55.44% by weight relative to the total weight of the composition.

4. A method of manufacturing a reduced-calorie product comprising adding the sweetener composition according to claim 1 to a food product, a beverage product, a pharmaceutical product, a nutritional product, a sports product, or a cosmetic product.

5. A method of increasing bulk of a product comprising adding the sweetener composition according to claim 1 to the product.

6. A method of coating a product comprising applying the sweetener composition according to claim 1 to the product.