WO2023089335A1 - Composition d'édulcorant - Google Patents

Composition d'édulcorant Download PDF

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Publication number
WO2023089335A1
WO2023089335A1 PCT/GB2022/052942 GB2022052942W WO2023089335A1 WO 2023089335 A1 WO2023089335 A1 WO 2023089335A1 GB 2022052942 W GB2022052942 W GB 2022052942W WO 2023089335 A1 WO2023089335 A1 WO 2023089335A1
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WIPO (PCT)
Prior art keywords
sweetener
dfa
sweetener composition
fructofuranose
dianhydride
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PCT/GB2022/052942
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English (en)
Inventor
Shawn Erickson
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Tate & Lyle Solutions Usa Llc
Tate & Lyle Technology Limited
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Publication of WO2023089335A1 publication Critical patent/WO2023089335A1/fr

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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A23L27/33—Artificial sweetening agents containing sugars or derivatives

Definitions

  • the present invention relates to a sweetener composition
  • a sweetener composition comprising at least one difructose anhydride (DFA)
  • DFA difructose anhydride
  • a method of sweetening a food or beverage product comprising adding the sweetener composition, a food or beverage product, table-top sweetener, or syrup comprising the sweetener composition, and use of the sweetener composition to sweeten a food or beverage product.
  • DFA difructose anhydride
  • sucrose generally referred to as ‘sugar’ or ‘table sugar’
  • glucose glucose
  • fructose corn syrup
  • high fructose corn syrup high fructose corn syrup
  • 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 low or no calories.
  • Known replacements for nutritive sweeteners include both natural and synthetic sweeteners, the latter often being referred to as ‘artificial sweeteners’.
  • sweeteners falling within this class have a sweetness many times that of sucrose, such that only very small amounts are needed to provide an equivalent level of sweetness to that of the nutritive sweetener being replaced.
  • High potency sweeteners typically require the addition of a bulking agent (for example, a non-sweet saccharide polymer such as maltodextrin), and generally fail to provide the same taste and functional properties as the nutritive sweetener being replaced.
  • sweetener is represented by ‘sugar alcohols’ or ‘polyols’ (for example, erythritol, xylitol, sorbitol, maltitol etc.). These sweeteners are generally able to provide a degree of calorie reduction (by way of example, sorbitol provides about 2.6 kcal/g compared to about 4 kcal/g for sucrose) while also providing bulk, but are often not able to fully mimic the desired taste characteristics (they often produce a perceived cooling sensation) or functional properties (such as browning). Furthermore, polyols are often not suitable for use at high levels due to low gastro-intestinal tolerance.
  • a low or zero calorie sweetener that is able to replace or partially replace nutritive sweeteners directly, without the need for other components such as bulking agents, temporal profile modifiers, flavor enhancers and the like.
  • Such sweetener should be able to be used in high amounts to provide the bulk, sweetening and functional properties of the nutritive sweeteners being replaced.
  • DFAs Difructose anhydrides
  • sucrose or fructose are a class of compounds that are formed by heating sucrose or fructose. They are the product of dimerization of fructose with the concomitant loss of two water molecules. DFAs occur naturally in small quantities and are found in thermally treated sucrose and fructose. Sucrose caramels, for example, contain a small amount of DFAs.
  • DFA 1 a-D-fructofuranose p-D-fructofuranose-1 ,2':2,3'-dianhydride
  • DFA 2 P-D-fructofuranose a-D-fructopyranose-1 ,2':2,3'-dianhydride
  • DFA 3 P-D-fructofuranose p-D-fructopyranose-1,2':2,3'-dianhydride
  • DFA 4 Di-p -D-fructofuranose-1 ,2':2,3'-dianhydride
  • DFA 5 P-D-fructofuranose-a-D-fructopyranose-1 ,
  • DFA 3 has been commercialised in Japan as Twintose® as a prebiotic. Separation, purification, isolation and characterization of other DFAs has not been reported.
  • the present invention relates to a sweetener composition comprising at least one difructose anhydride (DFA), a method of sweetening a food or beverage product comprising adding the sweetener composition, a food or beverage product, table-top sweetener, or syrup comprising the sweetener composition, and use of the sweetener composition to sweeten a food or beverage product.
  • DFA difructose anhydride
  • the present invention is based on the finding that DFAs exhibit sweetness and desirable sensory performance as sweetener compounds.
  • the invention provides the following embodiments:
  • Embodiment 1 A sweetener composition comprising at least one difructose anhydride in an amount of from about 15% to about 99% by weight relative to the total weight of the sweetener composition on a dry solids basis.
  • Embodiment 2 The sweetener composition according to Embodiment 1, wherein the sweetener composition comprises the at least one difructose anhydride in an amount of from about 20% to 95% by weight relative to the total weight of the sweetener composition on a dry solids basis.
  • Embodiment 3 The sweetener composition according to Embodiment 1 or 2, wherein the at least one difructose anhydride is selected from the group consisting of: a-D-fructofuranose p-D-fructofuranose-1 ,2':2,3'-dianhydride (DFA 1), P-D-fructofuranose a-D-fructopyranose-1 ,2':2,3'-dianhydride (DFA 2), P-D-fructofuranose p-D-fructopyranose-1 ,2':2,3'-dianhydride (DFA 3), Di-p -D-fructofuranose-1 ,2':2,3'-dianhydride (DFA 4), a-D-fructopyranose-p-D-fructopyranose-1 ,2':2,1'-dianhydride (DFA 5), P-D-fructofuranose-a-D-fructopyranose
  • Embodiment 4 The sweetener composition according to any preceding embodiment, wherein the at least one difructose anhydride is selected from the group consisting of: a-D-fructofuranose p-D-fructofuranose-1 ,2':2,3'-dianhydride (DFA 1), P-D-fructofuranose-a-D-fructopyranose-1 ,2':2,1'-dianhydride (DFA 6), and P-D-fructofuranose-p-D-fructopyranose-1 ,2':2,1'-dianhydride (DFA 13).
  • DFA 1 a-D-fructofuranose p-D-fructofuranose-1 ,2':2,3'-dianhydride
  • DFA 6 P-D-fructofuranose-a-D-fructopyranose-1 ,2':2,1'-dianhydride
  • DFA 13 P-D-fructofura
  • Embodiment 5 The sweetener composition according to any preceding embodiment, wherein any one of the at least one difructose anhydrides that are present is present individually in an amount of at least about 20% by weight relative to the total amount of difructose anhydrides present.
  • Embodiment 6 The sweetener composition according to any preceding embodiment, wherein the sweetener composition comprises at least one co-sweetener.
  • Embodiment 7 The sweetener composition according to Embodiment 6, wherein the co-sweetener is selected from the group consisting of at least one sugar alcohol, at least one high intensity sweetener, at least one nutritive sweetener, at least one nonnutritive sweetener, and mixtures thereof.
  • Embodiment 8 The sweetener composition according to Embodiment 7, wherein the high intensity sweetener is selected from the group consisting of stevia extracts, monk fruit extracts, sucralose, aspartame, acesulfame K, and mixtures thereof.
  • Embodiment 9 The sweetener composition according to Embodiment 7 or 8, wherein the at least one nutritive sweetener is selected from the group consisting of sucrose, glucose, glucose syrup, isoglucose, fructose, glucose-fructose syrup, maltose, lactose, corn syrup, high fructose corn syrup, invert sugar, molasses, honey, agave, and mixtures thereof.
  • Embodiment 10 The sweetener composition according to any of Embodiments 7 to 9, wherein the at least one non-nutritive sweetener is allulose.
  • Embodiment 11 The sweetener composition according to any preceding embodiment, wherein the sweetener composition comprises at least one bulking agent.
  • Embodiment 12 The sweetener composition according to Embodiment 11, wherein the at least one bulking agent is selected from the group consisting of maltodextrin, polydextrose, gums, soluble corn fiber (SCF), inulin, a starch, a polyol, and mixtures thereof.
  • the at least one bulking agent is selected from the group consisting of maltodextrin, polydextrose, gums, soluble corn fiber (SCF), inulin, a starch, a polyol, and mixtures thereof.
  • Embodiment 13 A method of sweetening a food or beverage product comprising adding the sweetener composition of any of Embodiments 1 to 12 to at least one additional food or beverage ingredient.
  • Embodiment 14 A food or beverage product comprising the sweetener composition according to any of Embodiments 1 to 12 and at least one additional food or beverage ingredient.
  • Embodiment 15 The food or beverage product according to Embodiment 14, wherein the food or beverage product comprises the sweetener composition in an amount such that the food or beverage product comprises the one or more difructose anhydrides in an amount of at least about 1% by weight relative to the total weight of the food or beverage product.
  • Embodiment 16 The food product according to Embodiment 14 or 15, wherein the food product is any one selected from the group consisting of a confectionary product (including, but not limited to, jelly candies, hard candies and gums), a dessert product such as, yogurt (including, but not limited to, full fat, reduced fat and fat-free dairy yoghurts, as well non-dairy and lactose-free yoghurts and frozen equivalents of all of these), frozen desserts (including, but not limited to, frozen dairy desserts such as icecream - including regular ice cream, soft-serve ice cream and all other types of ice cream - and frozen non-dairy desserts such as non-dairy ice cream, sorbet and the like), sweet bakery products (including, but not limited to, biscuits, cakes, rolls, pies, pastries, and cookies), pre-made sweet bakery mixes for preparing sweet bakery products, pie fillings (including, but not limited to, fruit pie fillings and nut pie fillings such
  • Embodiment 17 The beverage product according to Embodiment 15 or 16, wherein the beverage product is any one selected from the group consisting of a carbonated beverage (including, but not limited to, soft carbonated beverages), a non-carbonated beverage (including, but not limited to, soft non-carbonated beverages such as flavored waters and sweet tea or coffee based beverages), fruit-flavored beverage, fruit-juice, tea, milk, coffee especially those which are reduced sugar or low sugar products, and frozen beverage products.
  • a carbonated beverage including, but not limited to, soft carbonated beverages
  • a non-carbonated beverage including, but not limited to, soft non-carbonated beverages such as flavored waters and sweet tea or coffee based beverages
  • fruit-flavored beverage including, but not limited to, soft non-carbonated beverages such as flavored waters and sweet tea or coffee based beverages
  • fruit-flavored beverage including, but not limited to, soft non-carbonated beverages such as flavored waters and sweet tea or coffee based beverages
  • fruit-flavored beverage including, but not limited to, soft non-carbonated beverages such as
  • Embodiment 18 The beverage product according to Embodiment 14, 15, or 17, wherein the beverage product comprises the one or more difructose anhydrides in an amount of from about 2% to about 30% by weight relative to the total weight of the beverage product
  • Embodiment 19 A table-top sweetener comprising the sweetener composition according to the first aspect.
  • Embodiment 20 The table-top sweetener according to Embodiment 19, wherein the table-top sweetener is a dry table-top sweetener.
  • Embodiment 21 The table-top sweetener according to Embodiment 19 or 20, wherein the table-top sweetener is provided as tablets, granules or as a powder.
  • Embodiment 22 A syrup comprising the sweetener composition according to any of Embodiments 1 to 12.
  • Embodiment 23 Use of the sweetener composition according to any of Embodiments 1 to 12 to sweeten a food or beverage product.
  • Fig. 1 shows a schematic of a purification process for DFA 1, DFA 6 and DFA 13 as described in Example 1.
  • Fig. 2 shows sensory data comparing DFA 1 , DFA 6, DFA 10, sucrose and allulose as described in Example 2.
  • Fig. 3 shows an example of the format of the survey used in the sensory analysis in Example 2.
  • Fig. 4 shows the LCMS spectrum of the reaction product of Example 1.2.
  • Fig. 5 shows the LCMS spectrum of the fractions obtained in Example 1.3.1.
  • Fig. 6a shows the LCMS spectrum of the Fraction 1-1 obtained in Example 1.3.2.
  • Fig. 6b shows the LCMS spectrum of Fraction 1-1-1 obtained in Example 1.3.3.
  • Fig. 7 shows the LCMS spectrum of the product of Example 1.4.1.
  • Fig. 8 shows the LCMS spectrum of the product of Example 1.5.2.
  • the present invention relates to a sweetener composition comprising difructose anhydrides (DFAs) comprising at least one difructose anhydride, a method of sweetening a food or beverage product comprising adding the sweetener composition, a food or beverage product, table-top sweetener, or syrup comprising the sweetener composition, and use of the sweetener composition to sweeten a food or beverage.
  • DFAs difructose anhydrides
  • the present invention is based on the finding that DFAs exhibit sweetness and desirable sensory performance as sweetener compounds.
  • a given amount of the one of more DFAs in the sweetener composition provides a sweetness of from about 30% to about 50% of the sweetness of the same amount of sucrose. That is to say, a given amount of DFAs tastes as sweet as sucrose in an amount of 30% to 50% of the given amount of DFAs.
  • the sweetener composition of the present invention provides a sweetness of from about 30% to about 50% of the sweetness of sucrose.
  • the sweetener composition exhibits low or no off-flavors, particularly bitterness.
  • the one or more DFAs in the sweetener composition provide a sweetness of from 3.0 to 5.0, preferably 4.0 to 4.5, sucrose equivalents (SEV) when the sweetener composition is provided as a solution in water in an amount such that the concentration of DFAs is 10% by weight relative to the total weight of the solution.
  • the one or more DFAs in the sweetener composition provide a sweetness of from 3.0 to 5.0, preferably 4.0 to 4.5, sucrose equivalents (SEV) when the sweetener composition is provided as a solution in water in an amount such that the concentration of DFAs is 10% by weight relative to the total weight of the solution, and exhibit low or no off-flavors, particularly bitterness.
  • DFA difructose anhydride
  • DFA 1 a-D-fructofuranose p-D-fructofuranose-1 ,2':2,3'-dianhydride
  • DFA 2 P-D-fructofuranose a-D-fructopyranose-1 ,2':2,3'-dianhydride
  • DFA 3 P-D-fructofuranose p-D-fructopyranose-1,2':2,3'-dianhydride
  • DFA 4 Di-p -D-fructofuranose-1 ,2':2,3'-dianhydride
  • DFA 5 P-D-fructofuranose-a-D-fructopyranose-1 ,2':2,1'-dianhydride
  • the present invention provides a sweetener composition comprising at least one DFA in an amount of from about 15% to about 99% by weight relative to the total weight of the sweetener composition on a dry solids basis.
  • the sweetener composition comprises the at least one DFA in an amount of from about 20% to about 95% by weight relative to the total weight of the sweetener composition on a dry solids basis.
  • the sweetener composition comprises the at least one DFA in an amount of from about 15% to about 99% by weight relative to the total weight of the sweetener composition on a dry solids basis.
  • the sweetener composition comprises the at least one DFA in an amount of from about 15% to about 97%, from about 20% to about 95%, from about 25% to about 93%, from about 30% to about 91%, from about 35% to about 89%, from about 40% to about 87%, from about 45% to about 87%, from about 50% to about 85%, from about 55% to about 83%, from about 60% to about 81%, from about 65% to about 79%, from about 70% to about 77%, or from about 73% to about 75%, by weight relative to the total weight of the sweetener composition on a dry solids basis.
  • the sweetener composition comprises the at least one DFA in an amount of from about 25%, from about 30%, from about 35%, from about 40%, from about 45%, from about 50%, from about 55%, from about 60%, from about 65%, from about 70%, from about 75%, from about 80%, from about 85%, from about 90%, or from about 95%, to about 99%, by weight relative to the total weight of the sweetener composition on a dry solids basis.
  • the sweetener composition comprises the at least one DFA in an amount of from about 20% to about 30%, to about 35%, to about 40%, to about 45%, to about 50%, to about 55%, to about 60%, to about 65%, to about 70%, to about 75%, to about 80%, to about 85%, or to about 90%, by weight relative to the total weight of the sweetener composition on a dry solids basis.
  • the sweetener composition may comprise the at least one DFA in an amount of 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, 25%, 26%, 27%, 28%, 29%, 30%, 31%, 32%, 33%, 34%, 35%, 36%,
  • the at least one DFA is selected from the group consisting of DFA 1 , DFA 2, DFA 3, DFA 4, DFA 5, DFA 6, DFA 7, DFA 8, DFA 9, DFA 10, DFA 11 , DFA 12, DFA 13, and DFA 14.
  • the at least one DFA is selected from the group consisting of DFA 1, DFA 2, DFA 4, DFA 5, DFA 6, DFA 7, DFA 8, DFA 9, DFA 10, DFA 11 , DFA 12, DFA 13, and DFA 14.
  • the at least one DFA is selected from the group consisting of DFA 1, DFA 6, and DFA 13.
  • the at least one DFA is DFA 1.
  • the at least one DFA is DFA 6.
  • the at least one DFA is DFA 13.
  • any one of the at least one DFAs that are present is present individually in an amount of at least about 20% by weight relative to the total amount of DFAs present.
  • one of the at least one DFA is present in an amount of at least about 25%, at least about 30%, at least about 35%, at least about 40%, at least about 45%, at least about 50%, at least about 55%, at least about 60%, at least about 65%, at least about 70%, at least about 75%, at least about 80%, at least about 85%, at least about 90%, or at least about 95%, or at least about 99%, by weight relative to the total amount of DFAs present.
  • one of the at least one DFA is present in an amount of 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%,
  • the sweetener composition comprises one or more co-sweetener.
  • the co-sweetener may be a natural co-sweetener, a synthetic cosweetener or both may be used.
  • the co-sweetener is selected from the group consisting of at least one sugar alcohol, at least one high intensity sweetener, at least one nutritive sweetener, at least one non-nutritive sweetener, and mixtures thereof.
  • the sweetener composition may comprise the at least one sugar alcohol, the at least one nutritive sweetener, the at least one non-nutritive sweetener or mixtures thereof independently in an amount of from about 5% to about 85%, from about 10% to about 80%, from about 15% to about 75%, from about 20% to about 70%, from about 25% to about 65%, from about 30% to about 60%, from about 35% to about 55%, from about 40% to about 50%, or from about 45% to about 50%, or about 50%, by weight relative to the total weight of the sweetener composition on a dry solids basis.
  • the sweetener composition may comprise the at least one sugar alcohol, the at least one nutritive sweetener, the at least one non-nutritive sweetener or mixtures thereof independently in an amount of from about from about 1% to about 20%, from about 2% to about 15%, from about 3% to about 10%, or from about 5% to about 10%, by weight relative to the total weight of the sweetener composition.
  • the sweetener composition comprises the at least one sugar alcohol, the at least one high intensity sweetener, the at least one nutritive sweetener, the at least one non-nutritive sweetener, or mixtures thereof in an amount of 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, 25%, 26%, 27%,
  • the sweetener composition may comprise the at least one high intensity sweetener in an amount of from about 50 ppm to about 3000 ppm, from about 100 ppm to about 2500 ppm, from about 150 ppm to about 2000 ppm, from about 200 ppm to about 1500 ppm, from about 250 ppm to about 1000 ppm, or from about 500 ppm to about 750 ppm, relative to one million parts of the total sweetener composition on a dry solids basis.
  • the one or more cosweetener of the present invention may be used as the one or more cosweetener of the present invention.
  • specific examples include monk fruit extracts and stevia extracts, as well as any sweet compounds isolated from such extracts (including synthetic equivalents of such compounds).
  • the high intensity sweetener is selected from the group consisting of stevia extracts, monk fruit extracts, sucralose, aspartame, acesulfame K, and mixtures thereof.
  • the high intensity sweetener is a stevia extract.
  • Stevia or Stevia rebaudiana, contains sweet compounds in its leaves. These compounds may be extracted to provide stevia extracts.
  • the sweet taste of stevia extracts is mainly attributed to a family of compounds known as ‘steviol glycosides’, examples of which include rebaudiosides (i.e., rebaudioside A to F, M, N and X), rubusoside, stevioside, and dulcosides.
  • Stevia extracts, as well as sweeteners comprising any one or more steviol glycoside may be used as the one or more co-sweetener of the present invention. Extracts or sweeteners comprising rebaudioside A (Reb A) can be used. Blends or mixtures of individual steviol glycosides which have been individually isolated, produced and/or purified may also be used.
  • the high intensity sweetener is a monk fruit extract.
  • Monk fruit is the fruit of the Siraitia grosvenorii vine, also known as luo han guo.
  • the sweet taste of monk fruit extracts is mainly attributed to a family of compounds known as ‘mogrosides’, examples of which include mogroside V, mogroside IV, mogroside VI, oxomogroside V, mogroside HIE, neomogroside and siamenoside I.
  • Monk fruit extracts, as well as sweeteners comprising any one or more mogroside may be used as the one or more co-sweetener of the present invention. Extracts or sweeteners comprising mogroside V can be used.
  • the sweetener composition comprises a nutritive sweetener.
  • the nutritive sweetener may be selected from the group consisting of sucrose, glucose, glucose syrup, isoglucose, fructose, glucose-fructose syrup, maltose, lactose, corn syrup, high fructose corn syrup, invert sugar, molasses, honey, agave, and mixtures thereof.
  • the nutritive sweetener may be sucrose.
  • said nutritive sweetener may be present in an amount of up to about 30% by weight relative to the total weight of the sweetener composition.
  • the nutritive sweetener may be present in an amount of about 20% by weight relative to the total weight of the sweetener composition.
  • the at least one non-nutritive sweetener is allulose.
  • the sweetener composition comprises at least one bulking agent.
  • the bulking agent may be selected from the group consisting of maltodextrin, polydextrose, gums, soluble corn fiber (SCF), inulin, a starch, a polyol, such as erythritol, xylitol, sorbitol, or maltitol, and mixtures thereof.
  • the amount of bulking agent present in the sweetener composition according to the present invention may be from about 5% by weight to about 85%, for example from about 20% to about 80%, for example from about 50% to about 80%, for example about 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, or 85%, by weight relative to the total weight of the sweetener composition on a dry solids basis.
  • An amount of bulking agent of from about 50% to about 80% by weight relative to the total weight of the sweetener composition will often be particularly convenient, for example an amount of 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%, by weight relative to the total weight of the sweetener composition on a dry solids basis, as well as all intermediate values.
  • the present invention provides a method of sweetening a food or beverage product comprising adding the sweetener composition according to the invention to at least one additional food or beverage ingredient.
  • the present invention provides a food or beverage product comprising the sweetener composition according to the present invention and at least one additional food or beverage ingredient.
  • a sweetener composition in accordance with the present invention may be used in combination with one or more other food or beverage ingredients, including any of the food and beverage ingredients known in the art.
  • the food ingredient is a starchy ingredient, including all suitable types of flours (including bleached, unbleached and self-raising flours) and starches (including native and modified starches).
  • the starchy ingredient may be derived from any suitable source including, but not limited to, wheat, rice, maize (corn), oat, rye, barley, tapioca, sago, amaranth, arrowroot, sorghum, pea, banana, potato and sweet potato.
  • the source may be waxy or non-waxy.
  • the food or beverage ingredient may include one or more ingredients selected from the group consisting of leavening agents (such as yeast, bicarbonate of soda, baking soda, cream of tartar and the like), eggs or egg-derived products, fats, oils, water, milk and/or other dairy products, alcohol, gums, natural and/or artificial colors, natural and/or artificial flavors (such as vanilla), salt, chocolate and/or cocoa, coconut and coconut-derived products, spices, fruits and fruit-derived products, vegetables and vegetable-derived products, legumes and legume-derived products, nuts and nut-derived products, preservatives, stabilizers, antioxidants, emulsifiers, proteins, amino acids, vitamins, minerals, and any other ingredients suitable for inclusion in a food or beverage.
  • leavening agents such as yeast, bicarbonate of soda, baking soda, cream of tartar and the like
  • eggs or egg-derived products such as yeast, bicarbonate of soda, baking soda, cream of tartar and the like
  • fats fats, oils, water, milk and/or other dairy products
  • alcohol
  • the beverage ingredient is one or more ingredients selected from the group consisting of water, gums, natural and/or artificial colors, natural and/or artificial flavors, acidulants, salt, electrolytes, spices, fats, oils, fruits and fruit-derived products, vegetables and vegetable-derived products, legumes and legume-derived products, nuts and nut-derived products, milk and dairy products, preservatives, stabilizers, antioxidants, vitamins, minerals, protein (including whey protein and the like), amino acids, tea and tea extracts, herbs and herbal extracts, coffee and coffee extracts, and any other ingredients suitable for inclusion in a beverage.
  • ingredients selected from the group consisting of water, gums, natural and/or artificial colors, natural and/or artificial flavors, acidulants, salt, electrolytes, spices, fats, oils, fruits and fruit-derived products, vegetables and vegetable-derived products, legumes and legume-derived products, nuts and nut-derived products, milk and dairy products, preservatives, stabilizers, antioxidants, vitamins, minerals, protein (including whey protein and the like),
  • the food or beverage product of the present invention comprises the the sweetener composition in an amount such that the food or beverage product comprises one of more DFAs in an amount of at least about 1% by weight relative to the total weight of the food or beverage product.
  • food products according to the present invention may comprise the one of more DFAs in an amount of from about 8% by weight to about 45% by weight relative to the total weight of the food product, for example in an amount of from about 10% to about 40%, or from about 15% to about 35%, or about 8%, 9%, 10%, 15%, 20%, 25%, 30%, 35%, 40% or 45% by weight relative to the total weight of the food product.
  • the beverage product comprises the one or more DFAs in an amount of from about 2% to about 30% by weight relative to the total weight of the beverage product.
  • beverages according to the present invention may comprise the one or more DFAs in an amount of from about 2% by weight to about 25%, for example from about 2% by weight to about 20%, from about 2% by weight to about 15%, from about 2% by weight to about 7%, or from about 4% by weight to about 6%, or about 2%, 2.2%, 3%, 4%, 4.5%, 5%, 5.5%, 6%, 6.5%, 7%, 8%, 9%, 10%, 15%, 20% or 25% by weight relative to the total weight of the beverage.
  • Food or beverage products which may be contemplated in the context of the present invention include baked goods; sweet bakery products (including, but not limited to, rolls, cakes, pies, pastries, and cookies); pre-made sweet bakery mixes for preparing sweet bakery products; pie fillings and other sweet fillings (including, but not limited to, fruit pie fillings and nut pie fillings such as pecan pie filling, as well as fillings for cookies, cakes, pastries, confectionary products and the like, such as fat-based cream fillings); desserts, gelatins and puddings; frozen desserts (including, but not limited to, frozen dairy desserts such as ice cream - including regular ice cream, soft serve ice cream and all other types of ice cream - and frozen non-dairy desserts such as nondairy ice cream, sorbet and the like); carbonated beverages (including, but not limited to, soft carbonated beverages); non-carbonated beverages (including, but not limited to, soft non-carbonated beverages such as flavored waters and sweet tea or coffee based
  • the beverage product is any one selected from the group consisting of a carbonated beverage (including, but not limited to, soft carbonated beverages), a non-carbonated beverage (including, but not limited to, soft noncarbonated beverages such as flavored waters and sweet tea or coffee based beverages), fruit-flavored beverage, fruit-juice, tea, milk, coffee especially those which are reduced sugar or low sugar products, and frozen beverage products.
  • a carbonated beverage including, but not limited to, soft carbonated beverages
  • a non-carbonated beverage including, but not limited to, soft noncarbonated beverages such as flavored waters and sweet tea or coffee based beverages
  • fruit-flavored beverage including, but not limited to, soft noncarbonated beverages such as flavored waters and sweet tea or coffee based beverages
  • fruit-flavored beverage including, but not limited to, soft noncarbonated beverages such as flavored waters and sweet tea or coffee based beverages
  • fruit-flavored beverage including, but not limited to, soft noncarbonated beverages such as flavored waters and sweet tea or coffee based beverages
  • fruit-flavored beverage including, but not limited to,
  • the present invention provides a table-top sweetener comprising the sweetener composition according to the present invention.
  • the table-top sweetener is a dry table-top sweetener.
  • it may take the form of tablets, granules or a powder.
  • Liquid table-top sweeteners may also be contemplated, and typically take the form of an aqueous solution of the components.
  • the at least one other natural or synthetic sweetener include at least one high intensity sweetener.
  • the table-top sweetener may include sucralose or stevia extracts.
  • the table-top sweetener of the present invention preferably comprises the sweetener composition and at least one other co-sweetener.
  • the at least one other co-sweetener may be as described above.
  • the at least one other co-sweetener is selected from the group consisting of at least one the nutritive sweeteners described above and/or any of the high intensity sweeteners described above and/or any of the sugar alcohols described above and/or any of the non-nutritive sweeteners described above.
  • the table-top sweeteners of the present invention may optionally include one or more further ingredients selected from the group consisting of bulking agents as described above, natural and/or artificial flavors, natural and/or artificial colors, fiber, acidulants, vitamins, antioxidants, preservatives, starch hydrolysates and the like.
  • the dry table-top sweetener of the present invention comprises the sweetener composition in an amount such that the table-top sweetener comprises the one or more DFAs in an amount of from about 97.5% to about 99.8%, from about 98.5% to about 99.7%, or from about 99.0% to about 99.6% by weight relative to the total weight of the table-top sweetener on a dry solids basis.
  • the dry table-top sweetener of the present invention comprises the sweetener composition in an amount such that the table-top sweetener comprises the one or more DFAs in an amount of from about 99.25% to about 99.75% and sucralose in an amount of from about 0.25% to about 0.75% by weight relative to the total weight of the one or more DFAs and sucralose in the table-top sweetener on a dry solids basis.
  • the dry table-top sweetener may comprise the one or more DFAs in an amount of about 99.5% and sucralose in an amount of about 0.5%.
  • the dry table-top sweetener of the present invention comprises the sweetener composition in an amount such that the table-top sweetener comprises the one or more DFAs in an amount of from about 99.25% to about 99.75% and stevia extract in an amount of from about 0.25% to about 0.75% by weight relative to the total weight of the one or more DFAs and stevia extract in the table-top sweetener on a dry solids basis.
  • the dry table-top sweetener may comprise the one or more DFAs in an amount of about 99.5% and stevia extract in an amount of about 0.5%.
  • the dry table-top sweetener further comprises one or more nutritive sweetener or non-nutritive sweetener.
  • the nutritive sweetener may be selected from the group consisting of sucrose, glucose, glucose syrup, isoglucose, fructose, glucose-fructose syrup, maltose, lactose, corn syrup, high fructose corn syrup, invert sugar, molasses, honey, agave, and mixtures thereof.
  • the nutritive sweetener is sucrose in one preferred embodiment.
  • the table-top product includes a nutritive sweetener or non-nutritive sweetener
  • said nutritive sweetener or non-nutritive sweetener may be present in an amount of up to about 30% by weight relative to the total weight of the table-top sweetener on a dry solids basis.
  • the nutritive sweetener or non-nutritive sweetener may be present in an amount of about 26% by weight relative to the total weight of the table-top sweetener on a dry solids basis.
  • liquid table-top sweeteners the preferred composition will depend upon the intended dosage amount. Some liquid table-top sweeteners are formulated such that only a very small amount (e.g. a few drops or around 0.15 g) is required in typical applications (e.g. to sweeten a hot beverage), while other formulations are such that one or two teaspoons are required.
  • liquid table-top sweeteners that are formulated to be dosed in small amounts, it is generally necessary to include a relatively high concentration of natural or synthetic high intensity sweetener in the table-top composition in order to deliver the required level of sweetness per unit volume.
  • Liquid table-top sweeteners of this type may typically comprise the sweetener composition in an amount such that the table-top sweetener comprises one or more DFAs in an amount of from about 25% to about 85% by weight (for example from about 25% to about 35%, or from about 75% to about 85% by weight) relative to the total weight of the one or more DFAs and at least one other natural or synthetic high intensity sweetener in the table-top sweetener.
  • the at least one other natural or synthetic sweetener is therefore typically present in an amount of from about 15% to about 75% by weight (for example from about 65% to about 75%, or from about 15% to about 25% by weight) relative to the total weight of the one or more DFAs and at least one other natural or synthetic high intensity sweetener in the table- top sweetener.
  • the at least one other natural or synthetic sweetener is preferably at least one natural or synthetic high intensity sweetener.
  • a preferred high intensity sweetener is sucralose.
  • Another preferred high intensity sweetener is stevia extract.
  • the present invention provides a syrup comprising the sweetener composition according to the present invention.
  • the syrup comprises from about 70% to about 90% of the sweetener composition by weight relative to the total weight of syrup, for example from about 75% to about 85% by weight.
  • the present invention provides the use of the sweetener composition according to the present invention to sweeten a food or beverage product.
  • a beverage such as a carbonated or non-carbonated beverage or a juice drink comprising the sweetener composition and one or more synthetic high intensity sweeteners such as sucralose
  • a beverage including a beverage concentrate, comprising the sweetener composition, a natural high intensity sweetener (such as a Stevia sweetener), and a dietary fiber (e.g., a soluble dietary fiber, such as a soluble corn fiber), and an acidulant (e.g., citric acid); a yogurt, such as a Greek yogurt, comprising the sweetener composition (which may be free of any artificial sweeteners); a frozen dessert, comprising the sweetener composition, a dietary fiber (e.g., a soluble dietary fiber, such as a soluble corn fiber), a natural high intensity sweetener (such as a Stevia sweetener and/or a
  • DFAs were isolated from a heated fructose product using preparative liquid chromatography techniques (Example 1). The overall isolation scheme is shown in Fig. 1. The DFAs were subject to sensory analysis and were shown to exhibit sweetness and desirable sensory performance as sweetener compounds (Example 2). The results of the sensory analysis are shown in Fig. 2.
  • Fructose 35 g was reacted at 150°C for 3 hours to yield a brown syrup. The mixture was cooled to room temperature.
  • the brown syrup was subject to liquid chromatography-mass spectroscopy (LCMS) according to the conditions shown in Table 1.
  • LCMS liquid chromatography-mass spectroscopy
  • Fig. 4 shows the LCMS spectrum of the reaction product of Example 1.2. The peaks were assigned a number. 10 peaks having mass data consistent with DFAs were observed in the analysis spectrum. Peak 1 , Peak 5 and Peak 10 were selected for further purification and characterization.
  • the MPLC conditions were as follows:
  • Fig. 5 shows the LCMS spectrum of the fractions obtained in Example 1.3.1. Peak 1 was enriched in fraction 1 of Example 1.3.1 as compared with brown syrup of Example 1.2.
  • Step 1.3.1 was run several times in order to generate sufficient material for subsequent separations.
  • Fig. 6a shows the LCMS spectrum of Fraction 1-1.
  • Fig. 6b shows the LCMS spectrum of Fraction 1-1-1.
  • Fraction 2 of Example 1.3.1 was loaded onto a prep-HPLC equipped with a Waters Atlantis T3 column. 6 fractions were obtained (Fractions 2-1 to 2-6).
  • the HPLC conditions were as follows: Column: Waters Atlantis T3 (150 x 30 mm, 5 pm);
  • Step 1.5.1 was run several times in order to generate sufficient material for subsequent separations.
  • the crude DFA 13 was further purified by prep-HPLC with Waters Atlantis T3 column.
  • the prep-HPLC conditions were as follows:
  • DFAs Sensory properties of DFAs as they relate to other bulk sweeteners were evaluated by a panel of experts. 6 experts were selected from a larger panel and asked to taste 5 products and assess their performance. Solutions of all DFAs tested at a concentration of 10 wt.% in water were found to exhibit equivalent sweetness to that of a 4.0 to 4.5 wt.% solution of sucrose in water, i.e. a 10 wt.% solution of the tested DFAs in water had a sucrose equivalent value (SEV) of 4 to 4.5. DFA 6 showed positive sensory performance as a sweetener compared to sucrose and allulose. DFA 6 did not show bitterness and produced a low cooked sugar I cotton candy flavour.
  • SEV sucrose equivalent value
  • Training was accomplished during 1 session.
  • the training framework was to compare various solutions of sucrose, sucrose + caffeine and allulose to evaluate the panelists ability and improvement on performance after discussion from the first to the second repetition. Samples were served in a fixed order to allow discussions.
  • Panelists were asked to familiarize themselves with the intensity of each of Training Examples 2-1 to 2-4 (measured with a 4 g spoon) and its corresponding SEV. After 30 seconds, they cleansed their palate with water and a cracker. Then panelists were asked to taste the entire 4 g sample (identified by a random 3-digit code). Then they were instructed to drag a marker on a line scale to match the sweetness of their test samples relative to the references noted above, with the scale ranging from 0 to 15. The value they selected was shown above the line scale so panelists were aware of what values they were indicating. Once this was complete and without tasting again, inquiries related to the liking of the test sample, the similarity of the taste of the test sample to sugar, the intensity of any off flavors, and the identity of any off-flavors were asked using the format shown in Fig. 3.
  • the values used for the liking scale were a standard 7-point hedonic scale ranging from 1 to 7, and the off flavor scale was a zero-point anchored 6-point intensity scale ranging from 0 to 5.
  • the description of the off-flavor was open ended to allow panelists to give any names they would like to potential off notes. Off flavors were discussed after the first repetition.
  • Fig. 2 shows the DFAs exhibited sweetness of between 4 and 4.5 SEV.
  • Fig. 2 also shows that the quality of the sweetness data is valid given because allulose was estimated around 6.5 SEV and 2% sucrose was estimated at 2.3 SEV, which are the expected values.
  • DFA 6 did not show any bitterness and produced only a low cooked sugar/cotton candy flavor. Therefore, DFA 6 showed positive sensory performance as a sweetener compared to sucrose and allulose. The present results show that DFAs can be useful as full or partial replacements for nutritive sweeteners such as sucrose.

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Abstract

L'invention concerne une composition d'édulcorant comprenant au moins un anhydride de difructose (DFA), un procédé pour édulcorer un produit alimentaire ou de boisson comprenant l'ajout de la composition d'édulcorant, un produit alimentaire ou de boisson, un édulcorant de table, ou un sirop comprenant la composition d'édulcorant et l'utilisation de la composition d'édulcorant pour édulcorer un produit alimentaire ou de boisson.
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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11100395A (ja) * 1997-09-29 1999-04-13 Showa Sangyo Co Ltd 新規二糖、甘味剤、該二糖の製法および酵素
JPH11103814A (ja) * 1997-09-30 1999-04-20 Showa Sangyo Co Ltd 苦味剤、味質改善剤、苦味付与または味質改善のための使用、および苦味を付与したか味質を改善した飲食品または薬品
JPH11155520A (ja) * 1997-09-29 1999-06-15 Showa Sangyo Co Ltd 甘味剤等もしくは甘味付与等のための使用、および甘味付与等した飲食品もしくは薬品
WO2018091759A1 (fr) * 2016-11-18 2018-05-24 Universidad De Granada Procédé de préparation de bonbons ayant une teneur élevée en oligosaccharides prébiotiques

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11100395A (ja) * 1997-09-29 1999-04-13 Showa Sangyo Co Ltd 新規二糖、甘味剤、該二糖の製法および酵素
JPH11155520A (ja) * 1997-09-29 1999-06-15 Showa Sangyo Co Ltd 甘味剤等もしくは甘味付与等のための使用、および甘味付与等した飲食品もしくは薬品
JPH11103814A (ja) * 1997-09-30 1999-04-20 Showa Sangyo Co Ltd 苦味剤、味質改善剤、苦味付与または味質改善のための使用、および苦味を付与したか味質を改善した飲食品または薬品
WO2018091759A1 (fr) * 2016-11-18 2018-05-24 Universidad De Granada Procédé de préparation de bonbons ayant une teneur élevée en oligosaccharides prébiotiques

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 199925, Derwent World Patents Index; AN 1999-296526 *
DATABASE WPI Week 199926, Derwent World Patents Index; AN 1999-305797 *
DATABASE WPI Week 199934, Derwent World Patents Index; AN 1999-398027 *
OSHIMA HISAKA ET AL: "PSICOSE CONTENTS IN VARIOUS FOOD PRODUCTS AND ITS ORIGIN", FOOD SCIENCE AND TECHNOLOGY RESEARCH, KARGER, BASEL, CH, vol. 12, no. 2, 1 January 2006 (2006-01-01), pages 137 - 143, XP003035928, ISSN: 1344-6606, DOI: 10.3136/FSTR.12.137 *

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