MIXTURES COMPRISING RARE SUGARS AND TASTE MODIFYING COMPOUNDS

Abstract

The present invention primarily relates to a mixture comprising or consisting of components a), b) and c), and optionally component d), wherein component a) is at least one rare sugar, component b) is at least one taste modifying compound, component c) is at least one natural sweet tasting compound, and component d) is at least one natural caloric sweet-tasting carbohydrate and/or at least one non-caloric sweet tasting sugar alcohol.

Claims

1. A mixture comprising components a), b) and c), and optionally, component d), wherein component a) is at least one rare sugar, component b) is at least one taste modifying compound chosen from hydroxyflavonoids, dihydrochalcons, dihydroisocoumarins, hydroxylignans, and mixtures thereof, component c) is at least one natural sweet tasting compound, and component d), if present, is at least one natural caloric sweet-tasting carbohydrate and/or at least one non-caloric sweet tasting sugar alcohol.

2. The mixture according to claim 1, wherein component b) comprises hesperetin, hesperetin dihydrochalcone, naringenin, phloretin, eriodictyol, homoeriodictyol, or mixtures thereof.

3. The mixture according to claim 1, wherein component b) comprises hesperetin or hesperetin dihydrochalcone or phloretin or phyllodulcin, or hesperetin and hesperetin dihydrochalcone, or hesperetin and phloretin, or hesperetin and phyllodulcin, or hesperetin dihydrochalcone and phloretin, or hesperetin dihydrochalcone and phyllodulcin, or phloretin and phyllodulcin, hesperetin and hesperetin dihydrochalcone and phloretin, or hesperetin and hesperetin dihydrochalcone and phyllodulcin, or hesperetin and phloretin and phyllodulcin, or hesperetin dihydrochalcone and phloretin and phyllodulcin, or hesperetin and hesperetin dihydrochalcone and phloretin and phyllodulcin.

4. The mixture according to claim 1, wherein component c) comprises at least one steviol glycoside.

5. The mixture according to claim 1, wherein component d) comprises at least one sugar chosen from sucrose, fructose, glucose, galactose, lactose, dextrose, maltose, sorbitol, xylitol, isomalt, lactitol, maltitsorbitol, erythritol, mannitol, galactitol, and mixtures thereof, preferably sucrose, D-fructose, D-glucose, D-galactose, D-lactose, D-maltose, sorbitol, xylitol, isomalt, lactitol, maltitsorbitol, erythritol, mannitol, galactitol, and mixtures thereof.

6. The mixture according to claim 1, wherein: the weight ratio of component a) to component b) ranges from 100,000:1 to 10:1, and/or the weight ratio of component a) to component c) ranges from 20,000:1 to 2:1, and/or the weight ratio of component a) to component d), if present, ranges from 10:1 to 1:200, and/or the weight ratio of component b) to component c) ranges from 100:1 to 1:100.

7. The mixture according to claim 1, further comprising component e), wherein component e) is at least one substance chosen from flavorings and/or aromatic substances other than compounds falling within one of the definitions of components a) to d).

8. A flavoring composition, concentrate, and/or intermediate for a food or beverage product comprising the mixture of claim 1.

9. A food or beverage product comprising a flavoring composition, concentrate, and/or intermediate according to claim 8.

10. The food or beverage product according to claim 9, wherein the amount of the mixture ranges from 0.05 to 25% by weight, based on the total weight of the food or beverage product.

11. The food or beverage product according to claim 9, wherein the amount of component a) ranges from 0.1 to 10% by weight, based on the total weight of the food or beverage product, and/or the amount of component b) ranges from 1 to 100 ppm by weight, based on the total weight of the food or beverage product, and/or the amount of component c) ranges from 5 to 500 ppm by weight, based on the total weight of the food or beverage product, and/or the amount of component d), if present, ranges from 1.0 to 30% by weight, based on the total weight of the food or beverage product.

12. The food or beverage product according to claim 9, wherein component a) comprises L-arabinose, D-tagatose, D-allulose, D-allose, L-rhamnose, D-trehalose, or combinations thereof, component b) comprises phloretin, hesperetin, or combinations thereof, component c) comprises rebaudioside A, glycosylated rubusoside, glucosylated steviosides, luo han guo extract, or combinations thereof, and component d), if present, comprises sucrose, glucose, fructose, lactose, or combinations thereof.

13. The food or beverage product according to claim 9, further comprising component f), wherein component f) is at least one artificial sweet tasting compound.

14. A method for imparting a sweet taste impression and/or reinforcing a sweet taste impression of a flavoring composition, a concentrate, and/or an intermediate for a food or beverage product comprising incorporating a mixture of claim 1 into the flavoring composition, concentrate, and/or intermediate.

15. A method for enhancing the onset of sweetness intensity, overall sweetness intensity, and/or full body of a flavoring composition, a concentrate, and/or an intermediate for a food or beverage product comprising incorporating a mixture of claim 1 into the flavoring composition, concentrate, and/or intermediate.

16. The mixture of claim 1, wherein the at least one rare sugar of component a) is chosen from D-(+)-allulose, L-(+)-rhamnose, L-fucose, L-(+)-arabinose, D-(−)-tagatose, D-(+)-trehalose, D-(+)-xylose, D-(+)-allose, D-(+)-altrose, D-(−)-gulose, D-(+)-mannose, D-(−)-idose, D-(+)-talose, D-(−)-lyxose, (D)-xylulose, (D)-ribulose, D-(−)-erythrose, D-(−)-threose, D-(+)-melezitiose, D-(+)-raffinose and mixtures thereof, preferably D-(+)-allulose, L-(+)-rhamnose, L-(+)-arabinose, D-(−)-tagatose, D-(+)-trehalose, D-(+)-allose and mixtures thereof.

17. The mixture of claim 1, wherein the at least one natural sweet tasting compound of component c) is chosen from steviol glycoside, steviolmonoside, steviolbioside A, steviolbioside B, stevioside B, stevioside C, rebaudioside A, rebaudioside AM, rebaudioside B, rebaudioside C (dulcoside B), rebaudioside D, rebaudioside E, rebaudioside E2, rebaudioside E3, rebaudioside F, rebaudioside I, rebaudioside H, rebaudioside L, rebaudioside K, rebaudioside KA, rebaudioside J, rebaudioside N, rebaudioside O, rebaudioside M, rebaudioside X, dulcoside A, rubusoside, glycosylated rubusosides, suavososides, Rubus suavissumus leaf extract, Stevia leaf extract, stevioside, glycosylated steviol glycosides, glycosylated steviosides, mogroside V, isomogroside, mogroside IV, Luo Han Guo fruit extract, siamenoside, monatin and its salts (monatin SS, RR, RS, SR), curculin, glycyrrhizic acid and its salts, thaumatin, monellin, mabinlin, brazzein, hernandulcin, Lippia dulcis extract, glycyphyllin, Smilax glycyphylla extract, phloridzin, Malus derived extracts, trilobatin, Malus trilobata derived extraxts, baiyunoside, osladin, polypodoside A, pterocaryoside A, pterocaryoside B, mukurozioside, phlomisoside I, periandrin I, abrusoside A, cyclocarioside I, Balansin A, Balansin B, and combinations thereof.

18. The mixture of claim 4, wherein the at least one steviol glycoside is rebaudioside A, glucosylated steviosides, rubusoside, glycosylated rubusoside, Stevia leaf extract, Rubus suavissimus extract, mogrosides, luo han guo, or mixtures thereof.

19. The mixture according to claim 1 wherein: the weight ratio of component a) to component b) ranges from 100,000:1 to 10:1, the weight ratio of component a) to component c) ranges from 20,000:1 to 2:1, the weight ratio of component a) to component d), if present, ranges from 10:1 to 1:200, and the weight ratio of component b) to component c) ranges from 100:1 to 1:100.

20. The mixture according to claim 1, wherein: the weight ratio of component a) to component b) ranges from 20,000:1 to 100:1, the weight ratio of component a) to component c) ranges from 5,000:1 to 20:1, the weight ratio of component a) to component d), if present, ranges from 10:1 to 1:20, and the weight ratio of component b) to component c) ranges from 10:1 to 1:40.

Description

EXAMPLES

[0093] Unless otherwise stated, percentages given herein refer to weight percentages per weight, i.e. % (w/w). The term “x° Brix” denotes a mixture comprising x % sucrose; that is, 2°Brix means a mixture comprising 2% sucrose and 5°Brix means a mixture comprising 5% sucrose.

[0094] Further, in the column headers below, the following abbreviations are used. The phrase “onset intensity” is short for onset sweetness intensity <2 sec. The phrase “overall intensity” is short for overall sweetness intensity. The phrase “lingering artificial” is short for “lingering artificial sweetness”. The phrase “off-notes” is short for off-notes (bitter, metallic, astringent).

[0095] Moreover, the following abbreviations are referred to in the following:

[0096] allulose D-(+)-allulose,

[0097] arabinose L-(+)-arabinose,

[0098] rhamnose L-(+)-rhamnose,

[0099] tagatose D-(−)-tagatose,

[0100] trehalose D-(+)-trehalose

[0101] HC hesperetin dihydrochalkon,

[0102] HT hespertin,

[0103] PH phloretin,

[0104] SG steviol glycoside,

[0105] OR glycosylated rubusoside,

[0106] LHG Lo Han Guo

Example 1: Sweetness-Enhancing Effect Imparted by a Rare Sugar in a Mixture Further Comprising a Natural Sweet Tasting Compound and a Natural Caloric Sweet-Tasting Carbohydrate

[0107] In this example, a mixture comprising 2% sucrose (2°Brix) and 30 ppm rebaudioside A (Reb A) was used as a base and compared to like mixtures that additionally comprised a rare sugar and to a mixture comprising 5% sucrose (5°Brix), which does neither comprise Reb A nor a rare sugar.

[0108] The rare sugar was added in a final amount of 2%. Different rare sugars were evaluated in this example, including allulose, rhamnose, trehalose, tagatose and arabinose.

[0109] The resulting mixtures were subjected to a sensory evaluation conducted by an expert panel. Two repetitions were made. The results are summarized in the following Tables 1 to 3 (results on arabinose are not shown).

TABLE-US-00002 TABLE 1 Results from two repetitions on the sweetness evaluation of different mixtures by an expert panel (n = 10). Onset Overall Full Lingering Composition intensity intensity body artificial Off-notes Remarks 2° Brix + 3.09 3.83 3.21 2.38 1.26 30 ppm Reb A 5° Brix 5.59 5.87 5.76 1.39 0.8 2° Brix + 4.27 4.69 4.3 2.21 1.26 30 ppm Reb A + 2% allulose 2° Brix + 4.62 5.16 4.63 2.72 1.27 30 ppm Reb A + 2% rhamnose 2° Brix + 3.99 4.49 3.92 2.5 1.25 30 ppm Reb A + 2% trehalose

TABLE-US-00003 TABLE 2 Results from two repetitions on the sweetness evaluation of different mixtures by an expert panel (n = 9-10). Onset Overall Full Lingering Composition intensity intensity body artificial Off-notes Remarks 2° Brix + 2.94 3.89 2.9 2.42 0.97 Cloggy 30 ppm Reb A 5° Brix 4.77 5.5 4.76 1.37 1.3 Fungal, caramel 2° Brix + 3.41 4.05 3.49 2.07 1.08 Bitter 30 ppm Reb A + 2% allulose 2° Brix + 3.81 4.54 3.96 1.76 0.97 Slightly 30 ppm Reb bitter, A + 2% cloggy rhamnose 2° Brix + 4.6 5.66 4.73 1.67 0.8 30 ppm Reb A + 2% tagatose

TABLE-US-00004 TABLE 3 Tukey (HSD) analysis of differences between categories with a 95% confidence interval. Onset Overall Full Lingering Composition intensity intensity body artificial Off-notes Remarks 2° Brix + B B C A A 30 ppm Reb A 5° Brix A A A A A 2° Brix + B B BC A A 30 ppm Reb A + 2% allulose 2° Brix + AB AB AB A A 30 ppm Reb A + 2% rhamnose 2° Brix + A A A A A 30 ppm Reb A + 2% tagatose

[0110] It was found that rhamnose is significantly more potent than allulose in sugar-reduced applications. In stevioside-sweetened applications, rhamnose and tagatose are found to be superior to allulose.

Example 2: Sweetness-Enhancing Effect Imparted by a Taste Modifying Compound, Optionally in Combination with an Additional Natural Sweet Tasting Compound, in a Natural Caloric Sweet-Tasting Carbohydrate-Free Mixture of the Present Invention

[0111] In this example, a sweetening solution comprising 100 ppm Reb A (as natural sweet tasting compound) and 1% rhamnose (as rare sugar) was used as a base and compared to like solutions that additionally comprised one or more taste modifying compound(s) and, optionally, at least one additional natural sweet tasting compound. As the taste modifying compound(s), hesperetin dihydrochalkon (HC), hespertin (HT) and/or phloretin (PH) was/were used. As additional natural sweet tasting compound, a steviol glycoside (SG), glycosylated rubusoside (OR) or Lo Han Guo (LHG) was used.

[0112] The results of the sensory evaluation are summarized in Table 4 below. Effects that were found to be particularly strong are highlighted in the table by values marked in bold.

TABLE-US-00005 TABLE 4 Results on the sweetness evaluation of different mixtures. Components in addition to Onset Overall Full Lingering Off- the base.sup.1 intensity intensity body artificial notes Remarks — 3.24 2.92 3.14 3.58 2.29 Bitter, carrot like taste 5 ppm HC 4.08 4.97 3.65 5.13 2.68 Cloggy, phenolic 10 ppm HT + 5.01 5.81 4.01 5.46 3.07 Plastic, 20 ppm PH + herbaceous 9 ppm LHG off-note 7 ppm HT + 4.85 5.20 3.75 4.34 2.24 Balsamic, 56 ppm SG bitter 20 ppm PH + 4.87 5.63 3.80 5.02 2.36 Bitter 45 ppm OR .sup.1base = 100 ppm Reb A + 1% rhamnose.

[0113] It was found that the sweet intensity (overall and impact) is strongly increased with all taste modifying compounds. Simultaneously, an undesired lingerie effect is increased.

Example 3: Sweetness-Enhancing Effect Imparted by a Taste Modifying Compound, Optionally in Combination with an Additional Natural Sweet Tasting Compound, in a Natural Caloric Sweet-Tasting Carbohydrate Containing Mixture of the Present Invention

[0114] In this example, a sweetening solution comprising 2% sucrose (as natural caloric sweet-tasting carbohydrate), 60 ppm Reb A (as natural sweet tasting compound) and 1% rhamnose (as rare sugar) was prepared as a base and compared to like solutions that additionally comprised one or more taste modifying compound(s) and, optionally, at least one additional natural sweet tasting compound. The taste modifying compound(s) and additional natural sweet tasting compound were the same as in Example 2.

[0115] The results of the sensory evaluation are summarized in Table 5 below. Effects that were found to be particularly strong are highlighted in the table by values marked in bold.

TABLE-US-00006 TABLE 5 Results on the sweetness evaluation of different mixtures. Components in addition to Onset Overall Full Lingering Off- base.sup.2 intensity intensity body artificial notes Remarks — 3.89 4.38 3.72 2.55 1.39 5 ppm HC 5.43 6.01 4.65 3.82 1.96 Phenolic, balsamic 10 ppm HT + 6.07 6.84 4.36 4.94 2.79 Phenolic, 20 ppm PH + balsamic, 9 ppm LHG bitter 56 ppm SG + 4.72 5.68 4.14 3.55 2.16 Alcoholic 7 ppm HT side note, bitter, slight vanilla note 20 ppm PH + 5.06 5.97 4.39 3.50 2.09 Honey like, 45 ppm OR herbaceous off-note, tea note .sup.2base = 2% sucrose + 60 ppm Reb A + 1% rhamnose.

[0116] It was again found that the sweet intensity (overall and impact) is strongly increased with all taste modifying compounds and that, simultaneously, an undesired lingerie effect is increased. When comparing to the results shown in Table 4, it can be concluded that presence of a natural caloric sweet-tasting carbohydrate (here: sucrose) had a beneficial effect on the complete sweetness profile including an emphasis of the desired effects and a suppression of the undesired effects.

Example 4: Sweetness-Enhancing Effect Imparted by a Rare Sugar in a Natural Caloric Sweet-Tasting Carbohydrate Free Mixture of the Present Invention

[0117] In this example, a sweetening solution comprising 100 ppm Reb A (as natural sweet tasting compound), 56 ppm SG (as additional natural sweet tasting compound) and 7 ppm HT (as taste modifying compound) was used as a base sweetening solution and compared to like solutions that additionally comprised a rare sugar in an amount of 1%. The tested rare sugars included rhamnose, allulose, trehalose, tagatose and arabinose.

[0118] The results of the sensory evaluation are summarized in Table 6 below. Effects that were found to be particularly strong are highlighted in the table by values marked in bold.

TABLE-US-00007 TABLE 6 Results on the sweetness evaluation of different mixtures. Components in addition Onset Overall Full Lingering Off- to base.sup.3 intensity intensity body artificial notes Remarks — 3.41 4.18 3.27 3.54 1.92 Balsamic note 1% rhamnose 4.03 4.73 3.91 3.85 2.17 Vanilla like, peppery notes, woody notes 1% allulose 4.28 5.06 3.51 4.42 2.76 Phenolic, peppery notes, woody notes, balsamic notes 1% trehalose 4.16 5.01 3.48 4.32 2.19 Vanilla like, balsamic notes 1% tagatose 4.16 4.82 4.01 3.38 2.39 Balsamic notes, smoky notes, stronger phenolic off notes 1% arabinose 3.82 4.22 3.99 2.98 2.09 Slightly herbaceous .sup.3base = 100 ppm Reb A + 56 ppm SG + 7 ppm HT.

[0119] Among the tested combinations, those containing rhamnose or trehalose performed best in regard of impact and intensity.

Example 5: Sweetness-Enhancing Effect Imparted by a Rare Sugar in a Natural Caloric Sweet-Tasting Carbohydrate Free Mixture of the Present Invention

[0120] In this example, a mixture comprising 2% sucrose (as natural caloric sweet-tasting carbohydrate), 60 ppm Reb A (as natural sweet tasting compound), 20 ppm PH (as a taste modifying compound) and 45 ppm OR (as additional natural sweet tasting compound) was used as a base and compared to like mixtures that additionally comprised a rare sugar in an amount of 1%. The tested rare sugars included rhamnose, allulose, trehalose, tagatose and arabinose.

[0121] The results of the sensory evaluation are summarized in Table 7 below. Effects that were found to be particularly strong are highlighted in the table by values marked in bold.

TABLE-US-00008 TABLE 7 Results on the sweetness evaluation of different mixtures. Components in addition to Onset Overall Full Lingering Off- base.sup.4 intensity intensity body artificial notes Remarks — 4.07 5.02 4.11 3.38 2.21 Woody, peppery note 1% rhamnose 4.89 5.63 4.71 3.32 2.36 Rum like note 1% allulose 4.67 5.42 4.68 3.19 2.30 Rum like note 1% trehalose 4.54 5.45 4.74 3.63 2.29 Rum like note 1% tagatose 4.78 5.55 4.81 3.18 2.16 Appley, slightly fermented 1% arabinose 4.58 5.33 4.51 2.99 2.13 .sup.4base = 60 ppm Reb A + 20 ppm PH + 45 ppm OR.

[0122] As can be gathered from Table 7, a mixture comprising a rare sugar, a taste modifying compound and at least one natural sweet tasting compound turned out to have a superior property profile as compared to a like mixture that does not contain a rare sugar. All desired effects were remarkably increased for all tested rare sugars, whereas the presence of rhamnose, allulose, tagatose and arabinose lead to a strong decrease of the lingering artificial sweetness. The addition of rhamnose or tagatose to the base was found to lead to a particular improvement of the impact sweetness and the mouth feeling (full body).

Example 6: Further Evaluation of the Sweetness-Enhancing Effect Imparted by Tagatose in a Natural Caloric Sweet-Tasting Carbohydrate Containing Mixture of the Present Invention

[0123] In this example, a mixture comprising 2% sucrose (as natural caloric sweet-tasting carbohydrate) and 60 ppm Reb A (as natural sweet tasting compound) was used as a base and compared to like mixtures that additionally comprised PH (as taste modifying compound) in combination with OR (as additional natural sweet tasting compound) and/or tagatose (as rare sugar) in an amount of 1%.

[0124] The results of the sensory evaluation are summarized in Table 8 below. Effects that were found to be particularly strong are highlighted in the table by values marked in bold.

TABLE-US-00009 TABLE 8 Results on the sweetness evaluation of different mixtures. Components in addition to Onset Overall Full Lingering Off- base.sup.5 intensity intensity body artificial notes Remarks — 3.55 4.20 3.69 2.70 1.85 20 ppm PH + 4.80 5.57 4.18 3.72 2.36 45 ppm OR 1% Tagatose 4.47 4.71 4.13 2.51 1.97 Woody, peppery 20 ppm PH + 5.35 5.69 4.89 3.15 2.55 Fruity, tea, 45 ppm OR + slightly 1% Tagatose dairy note .sup.5base = 2% sucrose + 60 ppm Reb A.

[0125] It was surprisingly found that a combination comprising a rare sugar, a taste modifying compound, at least one natural sweet tasting compound, and a natural caloric sweet-tasting carbohydrate was superior over like combinations that already performed superior but either lacked a rare sugar or a taste modifying compound. These results demonstrate that a mixture comprising a rare sugar, a taste modifying compound, at least one natural sweet tasting compound, and a natural caloric sweet-tasting carbohydrate is associated with beneficial effects including a remarkably increased onset sweetness intensity, overall sweetness intensity and full body. The beneficial effect was particularly pronounced with respect to the full body effect.

[0126] Moreover, when comparing the results from Tables 7 and 8 it can be concluded that replacing a natural caloric sweet-tasting carbohydrate (here: sucrose) in a mixture further comprising a taste modifying compound and at least one natural sweet tasting compound by a rare sugar leads to a remarkably improved property profile, where desired effects are increased and undesired effects are suppressed. Even more surprising is the observation that the increased lingering artificial sweetness from 3.38 to 3.72 associated with sucrose (cf. Table 7) could be completely neutralized and even lowered to 3.15 by the addition of tagatose (cf. Table 8). These results clearly demonstrate the superior sweetness taste profile associated with the mixture of the present invention.

Example 7: Ice Tea Containing a Natural Caloric Sweet-Tasting Carbohydrate Containing Mixture of the Invention

[0127] In this example, different ice tea preparations were prepared. The ingredients were mixed in the order listed in Table 9 into bottles and then sterilized.

TABLE-US-00010 TABLE 9 Ice tea preparations. Preparations (amounts in wt.-% or ppm if specified accordingly) Ingredients A B C D E F G H sucrose 7 3.5 3.5 3.5 3.5 3.5 1.5 — allulose — — 1 — — 0.5 2 7 rhamnose 1 2 — — — — — allose 3 — 3 — — — — trehalose — — — 3 — — — tagatose — — — — 2 — — arabinose — — — — — 3 — Hesperetin (HT) — — 5 ppm — — — — 7 ppm Phloretin (PH) — — — 15 ppm — — — 15 pmm Hersperetin — — — — 15 ppm —  5 ppm — dihydrochalcone (HC) Alpha- — — — — — 5 ppm 10 ppm — glycosylated rubusosides (OR) Alpha- — 10 10 — 10 — — — glycosylated steviosides (SG) Rebaudioside A — — — 10 — — — — Rebaudioside M — — — — 10 10 — — Citric acid 0.15 0.15 0.15 0.15 0.15 0.15 0.15 0.15 ascorbic acid 0.02 0.02 0.02 0.02 0.02 0.02 0.02 0.02 Black tea extrakt 0.15 0.15 0.15 0.15 0.15 0.15 0.15 0.15 natural lemon 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 flavor Water to 100% A and H: Comparative preparations. B-G: preparations in accordance to the invention.

Example 8: Carbonated Soft Drink (Flavor Direction: Cola) Containing a Mixture of the Invention

[0128] In this example, carbonated soft drinks are prepared. The solid components or ingredients shown in Table 10 are individually mixed with water, combined and made up to 100 g with water. The concentrate obtained is then allowed to age over night at ambient temperature. Finally, 1 part concentrate is mixed with 5 parts carbonated water, filled into bottles and sealed.

TABLE-US-00011 TABLE 10 Carbonated soft drinks. Ingredient (% by weight) A B C D E F G H I J Phosphoric acid 85% 0.635 0.635 0.635 0.635 0.700 0.5 0.5 0.5 0.5 0.5 Citric acid, anhydrous 0.064 0.064 0.064 0.064 — 0.25 0.25 0.25 0.25 0.25 Caffeine 0.064 0.064 0.070 0.064 0.060 0.064 0.064 0.064 0.064 0.03 Sucrose 63.60 — — — 12.9 15.1 0 0 0 0 Rebaudioside M — 0.200 — — — 0.100 0.200 — — — Glycosylated steviosides — — 0.150 — — — — 0.150 — — Aspartame — — — — 0.07 — — — — 0.07 Rebaudioside A — — — 0.150 — — — — 0.150 — Acesulfame K — — — — 0.07 — — — — 0.07 Mogroside V — — — 0.150 — — — — 0.150 — Sugar colouring 0.00 0.700 0.650 0.800 0.800 0.700 0.800 0.800 0.800 0.800 Cola type drink emulsion 1.545 1.445 1.445 1.445 1.445 1.300 1.445 1.2 1.6 1.3 Sodium benzoate 0.106 0.106 0.106 0.106 0.106 — — — — — D-Allulose 10 — 2 — — 5 — 1 — — rhamnose — 6 — 2 2 — 3 — 1 1 allose — 2 2 — — — 1 1 — — trehalose — — 2 4 3 — — 1 2 3 Tagatose — — 2 2 3 — — 1 1 3 arabinose — — — 4 — — — — 2 — D-Xylulose — — — — — 5 3 — — — D-Xylitol — — — — — — 2 — — — Erythritol — — — — — — — 4 3 — Mannitol — — — — — — — — 3 — Galactitol — — — — — — — — — 1 Alpha- — — — — 0.001 0.001 — — — 0.001 GlucosylatedRubusosides (OR) Hesperetin, racemic, 2.5% — 2.0 2.0 — — — 2.0 2.0 — — in 1,2-propylene glycol Phloretin, 2.5% in — — 1.0 — — 1.0 — 1.0 — — 1,2-propylene glycol Phyllodulcin, 0.5% in — — — 1.0 — — — — 1.0 — 1,2-propylene glycol Hesperetin — — — — 1.0 — — — — 1.0 dihydrochalcone (I) 0.5% in 1,2-propylene glycol Water ad 100 A: drink containing sugar (comparative drink). B-E: low-calorie drinks (in accordance to the invention)

Example 9: Sugar-Reduced Tomato Ketchup Containing a Natural Caloric Sweet-Tasting Carbohydrate Containing Mixture of the Invention

[0129] In this example, sugar-reduced tomato ketchup preparations are prepared. The Flavoring Part is mixed first and added to the other ingredients which are mixed in the stated sequence and the finished ketchup is homogenized using an agitator, poured into bottles and sterilized.

TABLE-US-00012 TABLE 11 Sugar-reduced tomato ketchup preparations. Preparation (amounts in weight-%) Ingredients A B C D E F G H Common salt 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 Starch, Farinex WM 55 1.0 1.0 1.0 1.0 1.0. 1.0 1.0 1.0 Sucrose 12.0 5 6 7 4 7 5 — Tomato concentrate ×2 40.0 40.0 40.0 40.0 30.0 30.0 30.0 30.0 Glucose syrup 80 Brix 18.0 18.0 18.0 18.0 18.0 18.0 18.0 18.0 Spirit vinegar 10% 7.0 7.0 7.0 7.0 3.0 3.0 3.0 3.0 Flavoring Part: spice flavour 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 D-Allulose 3 5 Rhamnose — — 3 — — — — — Allose — — — 4 — — — — Trehalose — — — — 5 — — 2 Tagatose — — — — — 3 — 5 Arabinose — — — — — — 6 — Alpha-glycosylated — — — 20 ppm  20 ppm — — — rubusosides (OR) Rebaudioside A — — 100 ppm — — — — — Rebaudiosid M — 100 ppm — — 100 ppm — — — Hesperetin 2.5% in — — 0.1 0.1 — 0.1 — 0.1 1,2-Propylene glycol Phloretin 2.5% in — — 0.1 0.1 — 0.1 — 0.1 1,2-Propylene glycol Alpha-Glycosylated — — — 0.1 0.1 0.05 — — rubusoside Hesperetin — — — — — — 0.2 — dihydrochalcone 0.5% in 1,2-Propylene glycol Phyllodulcin, 0.5% in — — — — 0.2 0.1 — 0.2 ethanol/1,2-propylene glycol Water ad 100 A: Comparative preparation with sugar. B-F: Preparations in accordance with the invention.

Example 10: Instant Ice Tea Type Peach

[0130] In this example, instant ice tea preparations are prepared by mixing the ingredients listed in Table 12 together. The standard dosage in water for preparing a peach ice tea beverage based on the instant is 7.5% by weight.

TABLE-US-00013 TABLE 12 Instant Ice Tea Type Peach preparations. A-C: Comparative preparations. D: preparation according to the present invention. Preparations (amounts in weight-%) Ingredients A B C D Sucrose, extra fine 95.06 70.09 70.25 — Citric acid, anhydrous 2.2 2.0 2.0 1.8 Black Tea extract, 1.34 1.34 1.34 1.34 powdered Peach aroma spray dried 0.66 0.66 0.66 0.66 Tea aroma type 0.27 0.27 0.27 0.27 Ceylon dried Trisodium citrate 0.25 0.25 0.25 0.25 Ascorbic acid 0.22 0.22 0.22 0.22 Polydextrose — — — 25 D-Allulose, crystalline — 10 — 30 Trehalose — 10 25 — Rhamnose — — — 30 Tagatose — 5 — 10 Hesperetin — — 0.01 0.01 dihydrochalcone (I) Hesperetin — 0.05 — — Rebaudioside A — — 0.01 0.01 Phloretin — 0.02 — — Rebaudioside M — 0.1 — 0.20 Homoeriodictyol- — 0.1 — 0.05 Sodium salt

Example 11: Chocolate Drink Instant Powder

[0131]

TABLE-US-00014 TABLE 13 instant powder preparations for a chocolate drink. A-C: Comparative preparations. D: preparation according to the present invention. Ingredient Use in weight % Preparation A B C D Sucrose, extra fine 73.5 48.475 43.69 13.325 Cocoapowder 25.0 25.0 25.0 25.0 alkalized, 10-12% by weight fat Maltodextrin DE15- 0.43 0.43 0.43 0.43 19 from corn starch Salt (NaCl), extra 0.43 0.43 0.43 0.43 fine Ascorbic acid 0.29 0.29 0.29 0.29 Vitamin mix M8 0.145 0.145 0.145 0.145 40-1507 D-Allulose, — 10 — 30 crystalline Trehalose — 10 30 — Rhamnose — — — 30 Tagatose — 5 — 10 Hesperetin — — 0.015 0.01 dihydrochalcone (I) Hesperetin — 0.05 — — Rebaudioside A — — 0.01 0.02 Phloretin — 0.03 — — Rebaudioside M — — — 0.30 Homoeriodictyol- — 0.15 — 0.05 Sodium salt

Example 12: Sucrose Reduced Yogurt (−50% Added Sucrose)

[0132] Part I: Yoghurt

TABLE-US-00015 TABLE 14 Ingredient Use in weight % Preparation A B C D E F G H I J Sucrose, extra fine 11.20 5.60 5.60 5.60 4.10 5.60 5.60 5.60 5.60 Standard Yogurt Culture 0.004 0.004 0.004 0.004 0.004 0.004 0.004 0.004 0.004 0.004 Natural Strawberry Flavor 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 D-Allulose, crystalline 3.15 0.5 1.0 2.0 D-Galactose 2.5 2.0 2.0 D-Tagatose 3.05 2.05 3.05 0.5 1.05 Hesperetin, 1% Lösung in 0.1 — 0.03 0.1 0.05 0.1 1,2-Propylenglycol Phloretin, 1% Lösung in 0.1 0.03 0.1 0.03 0.06 0.05 0.05 1,2-Propylenglycol Steviol Glycoside 95% — 1.05 alpha-glucosylated steviol glycosides — 0.013 0.13 0.0325 0.0325 pasteurized Milk, 3.5% ad to 100 A: Comparative full sugar preparation. E: Comparative reduced sugar preparation with steviolgylcosides as sweetener. B-D, F-J: preparation according to the present invention.

[0133] The ingredients are mixed and fermented at 22-30° C. for 6-12 h. The product is stored at 4-8° C. before consummation.

[0134] Part II: Fruit Preparation for Yogurt with No Added Sucrose

TABLE-US-00016 TABLE 15 Ingredient A B C D E Water 21.82% 21.85% 21.75% 21.75% 21.75% Fruit Residue Puree e.g. from 27.00% Strawberry, Apple, Banana Pectin 0.25% 0.15% 0.25% 0.25% 0.25% Sucrose 27.00% 0.00% Guar Gum 0.15% 0.15% 0.15% 0.15% 0.15% Potassium Sorbate 0.13% 0.13% 0.13% 0.13% 0.13% Frozen Fruit e.g. Strawberry 50.00% 50.00% 50.00% 50.00% 50.00% Natural Strawberry Flavor 0.65% 0.65% 0.65% 0.65% 0.65% D-Allulose 27.00% 5.00% D-Galactose 22.00% D-Tagatose 27.00% alpha-glucosylated rubusoside 0.07% 0.07% 0.07% 0.07%

[0135] Blend 20% Fruit Preparation Part II with 80% Yogurt Part I, fill and store at 5-8° C.