MIXTURE COMPRISING D-ALLULOSE AND TASTE MODIFYING COMPOUNDS

Abstract

The present invention primarily relates to a mixture comprising or consisting of a) D-allulose and b) a taste modifying compound selected from the group consisting of hesperetin, hersperetindihydrochalcone, phloretin, glycosylated rubusosides, balansines, phyllodulcin, eriodictyol, homoeriodictyol, matairesinol, and mixtures thereof. A further aspect of the present invention relates to a food or beverage product comprising a mixture according to the present invention.

Claims

1. A mixture comprising: a) D-allulose; and b) a taste modifying compound chosen from selected from the group consisting of hesperetin, hesperetin dihydrochalcone, phloretin, alpha-glycosyl rubusosides, balansines, phyllodulcin, eriodictyol, homoeriodictyol, matairesinol, and mixtures thereof, preferably hesperetin, hesperetin dihydrochalcone, alpha-glycosyl rubusosides, phloretin, and mixtures thereof.

2. A mixture according to claim 1 comprising: b1) a taste modifying compound chosen from hesperetin, homoeriodictyol, eriodictyol, phloretin, matairesinol, and mixtures thereof, and b2) a taste modifying compound chosen from hesperetin dihydrochalcone, alpha-glycosyl rubusosides, balansines, phyllodulcin, and mixtures thereof.

3. A mixture according to claim 1, wherein the weight ratio of D-allulose to the total mass of all compounds of group b) ranges from 100,000:1 to 10:1.

4. A mixture according to claim 2, wherein the weight ratio of the total mass of all compounds of group b1) to the total mass of all compounds of group b2) ranges from 100:1 to 1:100.

5. A mixture according to claim 1, further comprising one or more flavorings and/or aroma substances.

6. A mixture according to claim 1, further comprising one or more carbohydrates chosen from sucrose, D-fructose, D-glucose, lactose, palatinose, lactulose, D-tagatose, and mixtures thereof.

7. A mixture according to claim 1, wherein the total amount by weight of D-allulose ranges from 0.1 to 95.0%, based upon the total weight of the mixture.

8. A food or beverage product comprising a mixture according to claim 1.

9. A food or beverage product according to claim 8, wherein the amount of all compounds of group a) and b) contributes less than 2.0% sucrose equivalents to the food or beverage product.

10. A food or beverage product according to claim 8, wherein the sum of all compounds of group a) and b) is below its sweetness threshold.

11. A food or beverage product according to claim 8, wherein the amount of D-allulose ranges from 0.01 to 3.0 wt. %, based upon the total weight of the food or beverage product.

12. A food or beverage product according to claim 8, wherein the amount of D-allulose and of all compounds of group b) ranges from 0.01 to 3.0 wt. %, based upon the total weight of the food or beverage product.

13. A food or beverage product according to claim 8, further comprising an artificial sweetener and/or natural high-potency sweetener.

14. A food or beverage product according to claim 8, wherein the sum of all carbohydrates, except D-allulose, and all artificial and natural sweeteners cause a sweet intensity of at least 2% sucrose equivalents.

15. A method for imparting a sweet taste impression and/or reinforcing a sweet taste impression of one or more sweet-tasting substances and/or producing an orally consumable formulation comprising: a) providing a mixture according to claim 1, b) providing an orally consumable formulation comprising one or more sweet-tasting substances, and c) bringing into contact or mixing of the ingredients provided in steps a) and b).

16. A mixture according to claim 2 comprising: b1) a taste modifying compound chosen from hesperetin, phloretin, and mixtures thereof; and b2) a taste modifying compound chosen from hesperetin dihydrochalcone, alpha-glycosyl rubusosides, phyllodulcin, and mixtures thereof. 2

17. A mixture according to claim 1, wherein the weight ratio of D-allulose to the total mass of all compounds of group b) ranges 50,000:1 to 50:1. 3

18. A mixture according to claim 1, wherein the weight ratio of D-allulose to the total mass of all compounds of group b) ranges 50,000:1 to 100:1. 3

19. A mixture according to claim 2, wherein the weight ratio of the total mass of all compounds of group b1) to the total mass of all compounds of group b2) ranges from 10:1 to 1:10. 4

20. A mixture according to claim 2, wherein the weight ratio of the total mass of all compounds of group b1) to the total mass of all compounds of group b2) ranges from 5:1 to 1:5. 4

Description

EXAMPLES

Example 1: Ice Tea

Comparative Example with Sucrose (A)

Comparative Example with Sucrose and D-Allulose (B)

[0069] Examples according to the invention with D-allulose and a taste modifying compound (C-H)

TABLE-US-00001 Preparation (wt.-% or ppm if specified accordingly) Ingrediens A B C D E F G H sucrose 7 3.5 3.5  3.5  3.5  3.5  1.5 — D-allulose — 2 2  2  2  2  3  7 Hesperetin (HT) — — 5 ppm — — — —  7 ppm Phloretin (PH) — — — 15 ppm — — — 15 pmm Hersperetin — — — — 15 ppm —  5 ppm — dihydrochalcone (HC) Alpha-glycosylated — — — — — 10 ppm 10 ppm — rubusosides (OR) 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 flavor 0.1 0.1 0.1  0.1  0.1  0.1  0.1  0.1 water to 100%

[0070] The ingredients were mixed in the order listed in the order listed into bottled and sterilized.

[0071] According to sensory studies, the examples C-H show a better sweet impact, intensity, and mouthfeel without significantly increasing sweet lingering effects. The acidity is reduced in the formulations compared to allulose alone (B).

Example 2: Carbonated Soft Drink (Flavour Direction: Cola)

[0072] A: drink containing sugar (comparative drink)

[0073] B: low-calorie drink

[0074] C: low-calorie drink

[0075] D: low-calorie drink

[0076] E: low-calorie drink

TABLE-US-00002 A B C D E (% by (% by (% by (% by (% by Ingredient weight) weight) weight) weight) weight) Phosphoric acid 0.635 0.635 0.635 0.635 0.635 85% Citric acid, 0.064 0.064 0.064 0.064 0.064 anhydrous Caffeine 0.064 0.064 0.064 0.064 0.064 Sucrose 63.60 — — — 12.9 Rebaudioside M — 0.200 — — — Glycosylated — — 0.150 — — steviosides Aspartame — — — — 0.07 Rebaudioside A — — — 0.150 — Acesulfame K — — — — 0.07 Mogroside V — — — 0.150 — Sugar colouring 0.800 0.800 0.800 0.800 0.800 Cola type drink 1.445 1.445 1.445 1.445 1.445 emulsion Sodium benzoate 0.106 0.106 0.106 0.106 0.106 D-Allulose 10 8    8    12 8 Hesperetin, — 2.0  2.0  — — racemic, 2.5% in 1,2- propylene glycol Phloretin, 2.5% — — 1.0  — — in 1,2-propylene glycol Phyllodulcin, — — — 1.0 — 0.5% in 1,2-propylene glycol Hesperetin — — — — 1.0 dihydrochalcone (I) 0.5% in 1,2-propylene glycol Water ad 100

[0077] The solid components or ingredients 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.

Example 3: Sugar-Reduced Tomato Ketchup

[0078] A: Comparative preparation with sugar [0079] B: Comparative preparation with reduced sugar content (compared to A) [0080] C-H: Preparations according to the invention with reduced sugar content (compared to A) and mixture

TABLE-US-00003 Preparation (amounts in % by weight) Ingredient 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  9.6  9.2  8.4  9.6  9.6  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 — —  1  1.5  1  1  5 12 Hesperetin 2.5% in 1,2-Propylene glycol — —  0.1  0.1 —  0.1 —  0.1 Phloretin 2.5% in 1,2-Propylene glycol — —  0.1  0.1 —  0.1 —  0.1 Alpha-Glycosylated rubusoside — — —  0.1  0.1  0.05 — — Hesperetin dihydrochalcone 0.5% in — — — — — —  0.2 — 1,2-Propylene glycol Phyllodulcin, 0.5% in ethanol/1,2- — — — —  0.2  0.1 —  0.2 propylene glycol Water ad 100

[0081] 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.

Example 4: Reduced-Sugar Fruit Gums

[0082] A: Comparative Preparation

[0083] B-E: preparation according to the present invention

TABLE-US-00004 A B C D E (% by (% by (% by (% by (% by Ingredient weight) weight) weight) weight) weight) Saccharose 34.50 8.20 8.20 9.0 0 Glucose syrup, 31.89 30.09 30    30 35 DE 40 Iso Syrup C* Tru  1.50 2.10 1.5  2 3 Sweet 01750 (Cerestar GmbH) Gelatin 240  8.20 9.40 10   8.5 9 Bloom Polydextrose — 24.40 25   23 — (Litesse ® Ultra, Danisco Cultor GmbH) Green, yellow and  0.01 0.01 0.01 0.01 0.01 red colorings Citric acid  0.20 0.20 0.20 0.20 0.20 D-Allulose — 2 2.5  1.5 34 Orange flavour, — 0.5 — — — containing 1% by weight hesperetin Strawberry — — 0.4  — — flavour, containing 0.5% Phloretin and 0.5% Hesperetin Apple flavour, — — — 0.35 — containing 0.5% Phloretin and 0.5% Hesperetin Cherry flavoring, — — — — 0.10 containing 1% by weight of hesperetin dihydrochalcone (I) based on the flavoring Water Quantum satis 25.80 Note: Polydextrose is itself a non-sweet-tasting polysaccharide with a low calorific value.

Example 5: Spray-Dried Preparation as a Semi-Finished Product for Flavoring of Finished Products

[0084]

TABLE-US-00005 Ingredient Use in % by weight Preparation A B C D E F Maltodextrin from wheat 10  5  5  0 —  5 Rice flour according to — — — — 10 — WO 2018 219,465 Gum Arabic  0.5  1  0.5  1  0.3 — D-Allulose, crystalline  20 25 25  0 30 25 D-Allulose, syrup — — — 30 — — Hesperetin dihydrochalcone (I)  0.05 — — — — — Hesperetin —  0.2 —  0.3  0.3 — Homoeriodictyol-sodium salt — — —  0.2 — — Phloretin — —  0.5 —  0.2 — Extract from Hydrangea — — — — —  0.02 dulcis, ctg. 40% Phyllodulcin Drinking water Add to 100

[0085] The drinking water is placed in a container and maltodextrin and gum arabic is dissolved in it. Then the flavoring is emulsified in the carrier solution with a Turrax. The temperature of the spray solution should not exceed 30° C. The mixture is then spray-dried (inlet nominal temperature: 185-195° C., outlet nominal temperature: 70-75° C.).

[0086] Typical dosage: 1-3% by weight depending on the application.

Example 6: Instant Ice Tea Type Peach

[0087] Preparation A: Standard Preparation

[0088] Preparation B-D: Preparation According to the Present Invention

TABLE-US-00006 Ingredient Use in weight % Preparation A B C D Sucrose, extra fine 95.06 70.09 70.25 — Citric acid, 2.2 2.0 2.0 1.8 anhydrous Black Tea extract, 1.34 1.34 1.34 1.34 powdered Peach aroma 0.66 0.66 0.66 0.66 spray dried 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, — 25 25 70 crystalline Hesperetin — — 0.01 0.01 dihydrochalcone (I) Hesperetin — 0.05 — — Rebaudioside A — — — 0.01 Phloretin — 0.02 — — Rebaudioside M — — — 0.20 Homoeriodictyol- — 0.1 — 0.05 Sodium salt

[0089] Standard dosage in water for preparing a peach ice tea beverage: 7.5% by weight.

Example 7: Drink Chocolate Instant Powder

[0090] Preparation A: Standard Preparation

[0091] Preparation B-D: Preparation According to the Present Invention

TABLE-US-00007 Ingredient Use in weight % Preparation A B C D Sucrose, extra fine 73.5   48.475 43.69 13.325 Cocoa powder alkalized, 10-12% 25.0   25.0 25.0 25.0 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, — 25 30 60 crystalline Hesperetin — — 0.015 0.01 dihydrochalcone (I) Hesperetin — 0.05 — — Rebaudioside A — — — 0.02 Phloretin — 0.03 — — Rebaudioside M — — — 0.30 Homoeriodictyol- — 0.15 — 0.05 Sodium salt

[0092] Standard dosage in milk for preparing an choco beverage: 6.9% by weight.

Example 8: Sensory Tests

[0093] Abbreviations used in the following tables: Hesperetin (HT), Phloretin (PH), Hersperetin dihydrochalcone (HC), alpha-glycosylated rubusosides (OR)

a) Taste solution: 5% Sucrose+60 ppm Rebaudioside A in water

TABLE-US-00008 Profile Name Mouth- After- No. Sample Description Impact Intensity feel taste A1 Base i (5% 5   6   4   3.5  sucrose + 60 ppm rebaudioside A in water) A2 A3 + 1% allulose 6   7   5   4   A3 A1 + 5 ppm HT + 5.5  6.5  5   4   10 ppm OR + 10 ppm PH + 1 ppm HC A4 A3 + 2% allulose 6.5  7.5  6   4.5  B1 Base i (5% 5   6   4   3.5  sucrose + 60 ppm rebaudioside A in water) B2 B4 + 5 ppm 6.5  7.5  5   4.5  HC +10 ppm OR B3 B4 + 7 ppm HT + 6   7   5   4   15 ppm PH B4 B1 + 1% allulose 5.25 6.25 4.5 3.5  B1 Base i (5% 5   6   4   3.5  sucrose + 60 ppm rebaudioside A in water) B5 B1 + 2% allulose 5.5  6.5  4.5 3.75 B6 B5 + 7 ppm 7   8   5.5 4.75 HT + 15 ppm PH B7 B5 + 5 ppm 7   8.5  5.5 5.5  HC + 10 ppm OR
b) Taste solution: 7% Sucrose+0.15% Citric Acid+60 ppm Rebaudioside A

TABLE-US-00009 Name Profile No. Sample Description Impact Intensity Mouthfeel Aftertaste Acidity A5 Base ii (7% sucrose + 5.5 6.5 4.5 2.75 3 0.15% Citric Acid + 60 ppm rebaudioside A) A6 A5 + 5 ppm HT + 10 ppm 6.25 8 5.5 3.5 2 OR + 10 ppm PH + 1 ppm HC A7 A6 + 1% allulose 6.25 8 6 3.75 2 A8 A6 + 2% allulose 6.75 8 6.5 3.75 2 B8 Base ii (7% sucrose + 5.5 6.5 4.5 2.75 3 0.15% citric Acid + 60 ppm rebaudioside A) B9 B10 + 7 ppm HT + 50 ppm 6 7 5.5 3.5 2.75 OR B10 B8 + 1% allulose 5.5 6.5 4.5 2.75 3 B11 B10 + 15 ppm PH + 50 ppm 6.5 7.5 5.75 3.5 2 OR B8 Base ii (7% sucrose + 5.5 6.5 4.5 2.75 3 0.15% citric Acid + 60 ppm rebaudioside A) B12 B14 + 15 ppm PH + 50 ppm 6.5 7.5 5.5 3.25 1.75 OR B13 B14 + 7 ppm HT + 50 ppm 6.5 8 6 3.25 1.75 OR B14 B8 + 2% allulose 6 7 5 3 3