Reduced-sweetener products, flavoring mixtures for said reduced-sweetener products and process for the production of products of this type

Abstract

A flavoring mixture, comprising (i) one or more sweet-tasting substances, selected from the group of naturally occurring sweet-tasting substances and the physiologically compatible salts thereof without phyllodulcin and the physiologically compatible salts thereof, and (ii) phyllodulcin and/or one or more of the physiologically compatible salts thereof,
wherein the ratio of the sucrose equivalence of the concentration of the substance or substances of group (i) to the sucrose equivalence of the concentration of the substance or substances of group (i) is 2.

Claims

1. A flavoring mixture comprising: (i) sucrose; (ii) phyllodulcin and/or a salt thereof; and (iii) hydrangenol and/or a salt thereof; wherein a ratio of a sucrose equivalence of a concentration of the sucrose of (i) to a sucrose equivalence of a concentration of the phyllodulcin and/or salt of (ii) is 4, and the flavoring mixture synergistically enhances the sweetness of an aqueous composition comprising the flavoring mixture in comparison to an otherwise identical aqueous composition without the phyllodulcin and/or salt of (ii).

2. The flavoring mixture of claim 1, further comprising: (iv) at least one substance selected from the group consisting of a flavoring, an aromatic substance which enhances a sweet taste, and a physiologically compatible salt thereof.

3. The flavoring mixture of claim 1, further comprising at least one naturally occurring sweet-tasting substance selected from the group consisting of: a) carbohydrates selected from the subgroup consisting of trehalose, lactose, maltose, melizitose, melibiose, raffinose, palatinose, lactulose, D-fructose, D-glucose, D-galactose, L-rhamnose, D-sorbose, D-mannose, D-tagatose, D-arabinose, L-arabinose, D-ribose, D-gyceraldehyde and maltodextrin; b) naturally occurring sugar alcohols selected from the subgroup consisting of glycerol, erythritol, threitol, arabitol, ribitol, xylitol, sorbitol, mannitol, maltitol, isomaltitol, dulcitol, and lactitol; c) naturally occurring sweeteners, selected from the subgroup consisting of miraculin, curculin, monellin, mabinlin, thaumatin, curculin, brazzein, pentadin, D-phenylalanine and D-tryptophan; d) naturally occurring sweeteners, selected from the subgroup consisting of stevioside, steviolbioside, rebaudioside A, further stevilglycosides selected from rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside G, rebaudioside H, dulcoside and/or rubusoside, oslandin, polypodoside A, strogin 1, strogin, 2 strogin 4, selligueanin A, dihydroquercetin-3-acetate, perillartin, telosmoside A15, periandrin I-V, pterocaryosides, cyclocaryosides, mukuroziosides, trans-anethol, trans-cinnamaldehyde, bryosides, bryonosides, bryonodulcosides, carnosiflo sides, scandenosides, gypenosides, trilobatin, phloridzin, dihydroflavanols, hematoxylin, cyanin, chlorogenic acid, albiziasaponin, telosmosides, gaudichaudio side, mogrosides, hernandulcin and glycyrrhetinic acid; e) a physiologically compatible, sweet-tasting derivative of the naturally occurring sweet-tasting substance of a) to d); and f) a physiologically compatible salt of the substance or derivative of a) to e).

4. The flavoring mixture of claim 2, wherein the at least one substance of (iii) is selected from the group consisting of: hesperetin, phloretin, 3,7-dihydroxy-4-methoxyflavan, and (S)-3,7-dihydroxy-4-methoxyflavan.

5. The flavoring mixture of claim 1, further comprising at least one flavoring, auxiliary, or carrier.

6. The flavoring mixture of claim 1, wherein the ratio of the sucrose equivalence of the concentration of the sucrose of (i) to the sucrose equivalence of the concentration of the phyllodulcin and/or salt of (ii) is 6.

7. An orally consumable product comprising the flavoring mixture of claim 1.

8. The orally consumable product of claim 6, wherein a concentration of the flavoring mixture is adjusted such that a concentration of the phyllodulcin and/or salt of (ii) is from 0.5 to 15 ppm, based on the weight of the orally consumable product.

9. The orally consumable product of claim 6 selected from the group consisting of a pharmaceutical preparation, an oral care preparation, a semi-finished product, a liquid, and a solid foodstuff.

10. A method for enhancing sweetness of an orally consumable product, the method comprising adding the flavoring mixture of claim 1 to the orally consumable product.

11. A flavoring mixture comprising (i) sucrose; and (ii) an extract of Hydrangea Dulcis, the extract comprising from 0.1 to 50 wt. % of phyllodulcin and/or a salt thereof and from 0.01 to 30 wt. % of hydrangenol and/or a salt thereof, wherein the weight percent of the phyllodulcin, hydrangenol, and salts thereof is based on the dry weight of the extract; and wherein a ratio of a sucrose equivalence of a concentration of the sucrose of group (i) to a sucrose equivalence of a concentration of the phyllodulcin and/or salt of group (ii) is 4, and the flavoring mixture synergistically enhances the sweetness of an aqueous composition comprising the flavoring mixture in comparison to an otherwise identical aqueous composition without the extract of Hydrangea Dulcis.

12. The flavoring mixture of claim 11, further comprising (iii) at least one substance selected from the group consisting of a flavoring, an aromatic substance which enhances a sweet taste, and a physiologically compatible salt thereof.

13. The flavoring mixture of claim 11, further comprising at least one naturally occurring sweet-tasting substance selected from the group consisting of: a) carbohydrates selected from the subgroup consisting of trehalose, lactose, maltose, melizitose, melibiose, raffinose, palatinose, lactulose, D-fructose, D-glucose, D-galactose, L-rhamnose, D-sorbose, D-mannose, D-tagatose, D-arabinose, L-arabinose, D-ribose, D-gyceraldehyde and maltodextrin; b) naturally occurring sugar alcohols selected from the subgroup consisting of glycerol, erythritol, threitol, arabitol, ribitol, xylitol, sorbitol, mannitol, maltitol, isomaltitol, dulcitol, and lactitol; c) naturally occurring sweeteners, selected from the subgroup consisting of miraculin, curculin, monellin, mabinlin, thaumatin, curculin, brazzein, pentadin, D-phenylalanine and D-tryptophan; d) naturally occurring sweeteners, selected from the subgroup consisting of stevioside, steviolbioside, rebaudioside A, further stevilglycosides selected from rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside G, rebaudioside H, dulcoside and/or rubusoside, oslandin, polypodoside A, strogin 1, strogin, 2 strogin 4, selligueanin A, dihydroquercetin-3-acetate, perillartin, telosmoside A15, periandrin I-V, pterocaryosides, cyclocaryosides, mukuroziosides, trans-anethol, trans-cinnamaldehyde, bryosides, bryonosides, bryonodulcosides, carnosiflo sides, scandenosides, gypenosides, trilobatin, phloridzin, dihydroflavanols, hematoxylin, cyanin, chlorogenic acid, albiziasaponin, telosmosides, gaudichaudio side, mogrosides, hernandulcin and glycyrrhetinic acid; e) a physiologically compatible, sweet-tasting derivative of the naturally occurring sweet-tasting substance of subgroups a) to d); and f) a physiologically compatible salt of the substance or derivative of subgroups a) to e).

14. The flavoring mixture of claim 12, wherein the at least one substance of (iii) is selected from the group consisting of hesperetin, phloretin, 3,7-dihydroxy-4-methoxyflavan, and (S)-3,7-dihydroxy-4-methoxyflavan.

15. The flavoring mixture of claim 11, further comprising at least one flavoring, auxiliary, or carrier.

16. The flavoring mixture of claim 11, wherein the ratio of the sucrose equivalence of the concentration of the sucrose of group (i) to the sucrose equivalence of the concentration of the phyllodulcin and/or salt of (ii) is 6.

17. An orally consumable product comprising the flavoring mixture of claim 11.

18. The orally consumable product of claim 17, wherein a concentration of the flavoring mixture is adjusted such that a concentration of the phyllodulcin and/or salt of (ii) is from 0.5 to 15 ppm, based on the weight of the orally consumable product.

19. The orally consumable product of claim 16 selected from the group consisting of a pharmaceutical preparation, an oral care preparation, a semi-finished product, a liquid, and a solid foodstuff.

20. A method for enhancing sweetness of an orally consumable product, the method comprising adding the flavoring mixture of claim 11 to the orally consumable product.

Description

EXAMPLES

Example 1: Consecutive Extraction of Hydrangea dulcis

(1) 100 g of plant material (mainly leaves) dried directly from/out of the living plant (Hydrangea dulcis) are moistened with deionized water and left to stand for 16 hrs at room temperature such that fermentation takes place. The fermented plant material is dried again for 3 hrs at 40 C. 100 g of the fermented, dried plant material is then extracted with stirring using different solvents in increasing polarity (heptane, methylene chloride, ethyl acetate, ethanol/water 4:1) for 1 hour in each case at room temperature. The solvent is removed under vacuum and the dried extracts are tasted in a dose of 500 ppm on sugar solution (5%) and salt solution (0.5%) and assessed sensorially.

(2) TABLE-US-00001 Content of phyllodulcin (based Solvent Yield on dry mass) Sensory assessment Heptane 0.8 g 12.7% Herby, sweet, sweetener note Methylene 1.6 g 15.4% Sweetener note, licorice, chloride bitter Ethyl acetate 1.7 g 10.5% Bitter, sweet, green, herby Ethanol/water 20.2 g 1.4% Bitter, sweet, herby

Example 2: Production of an Ethanolic Hydrangea dulcis Dry Extract

(3) 2 g of dried fermented plant material (produced as described in Example 1) were extracted in 50 ml of ethanol for one hour under reflux. The solvent was removed under vacuum and the dried extract was tasted in a dose of 110 ppm on sugar solution (5%) and assessed sensorially.

(4) TABLE-US-00002 Content of phyllodulcin (based Solvent Yield on dry mass) Sensory assessment Ethanol 0.29 g 7.2% Herby, sweet, licorice, depth, woody

(5) The exemplary extract was tested for stability under an elevated thermal stress in comparison to pure phyllodulcin. A solution of 100 mg/l of phyllodulcin and 1.38% of the exemplary ethanolic extract (corresponds to 100 mg of phyllodulcin) in an aqueous phosphate buffer, adjusted to pH 9, was tested immediately after preparation and then at regular weekly intervals for its phyllodulcin content. In this respect, an aliquot of the respective test solution was separated in an HPLC installation (RP phase) and quantified by UV detection compared to a calibration with pure phyllodulcin. The samples were stored at 40 C. in closed glass vessels to prevent evaporation. The phyllodulcin contents of the test solutions are plotted against time in FIG. 1.

(6) As can clearly be seen from FIG. 1, pure phyllodulcin is decomposed more rapidly than a comparable quantity of phyllodulcin in the form of an extract according to the invention. In a rough estimation, the stability is approximately tripled.

Example 3: Production of an Ethyl Acetate Hydrangea dulcis Dry Extract

(7) 2 g of dried fermented plant material (produced as described in Example 1) were extracted in 50 ml of ethyl acetate for one hour at 40 C. with stirring. The solvent was removed under vacuum and the dried extract was tasted in a dose of 55 ppm on sugar solution (5%) and assessed sensorially.

(8) TABLE-US-00003 Content of phyllodulcin (based Solvent Yield on dry mass) Sensory assessment Ethyl acetate 0.1 mg 14.4% Herby, sweet, similar to sweetener

Example 4: Production of an Ethanolic/Aqueous Hydrangea dulcis Dry Extract

(9) 2 g of dried fermented plant material (produced as described in Example 1) were extracted in 50 ml of ethanol/water (7:3) for one hour at room temperature with stirring. The solvent was removed under vacuum and the dried extract was tasted in a dose of 145 ppm on sugar solution (5%) and assessed sensorially.

(10) TABLE-US-00004 Content of phyllodulcin (based Solvent Yield on dry mass) Sensory assessment Ethanol/water 0.52 g 5.3% Sweet, relatively neutral (v/v 7:3)

Example 5: Production of an Aqueous/Ethanolic Ethyl Acetate Hydrangea Dulcis Dry Extract

(11) 2 g of dried fermented plant material (produced as described in Example 1) were extracted in 50 ml of water/ethanol (1:1) for one hour at 40 C. with stirring. The solvent was removed under vacuum and the dried extract was tasted in a dose of 240 ppm on sugar solution (5%) and assessed sensorially.

(12) TABLE-US-00005 Content of phyllodulcin (based Solvent Yield on dry mass) Sensory assessment Water/ethanol 0.52 g 3.2% Sweet, honey (v/v 1:1)

Application Example 1: Sweetness Enhancement Using Hydrangea dulcis Extracts

(13) Preliminary Test: Inherent Sweetness of the Extract

(14) The inherent sweetness of the extract from Example 2 (containing 7.2% by weight of phyllodulcin, based on dry mass) which was dissolved in different concentrations in pure form in water (0.0010, 0.0025, 0.0050, 0.0100, 0.0250, 0.0500% by weight in water) was determined using a comparative series of different sucrose concentrations in water (0, 0.25, 0.5, 0.75, 1, 1.5, 2, 3, 4 and 5% by weight sucrose in water). The panelists were requested to test and grade each individual extract solution compared to the sucrose series (sucrose equivalence). The inherent sweetness of the extract for the concentrations mentioned above could be determined from the results obtained from the panelists.

(15) TABLE-US-00006 Concentration of Determination the extract from Phyllodulcin of the sucrose Example 2 in water concentration equivalence Other sensory [% by weight] in ppm in water description 0.0010 0.7 0.2% Tea note 0.0025 1.75 0.45% Tea note, hay 0.0050 3.5 0.64% Green tea 0.0100 7 0.83% Fennel, aniseed, black tea, slightly bitter 0.0250 17.5 1.78% Strong tea note, green, fishy, slightly bitter 0.0500 35 2.7 Licorice root, fishy, astringent, tea, hay, bitter

(16) It can be seen by extrapolation from the Table that it is possible to achieve a sucrose equivalence of 1.5% with approximately 200 ppm of the extract (corresponding to approximately 15 ppm of phyllodulcin) and 1% with approximately 150 ppm of the extract (corresponding to approximately 10 ppm of phyllodulcin).

(17) Enhancement of the Sweetness Sensation of a Sucrose Solution

(18) In order to quantify the enhancement of the sweetness sensation, the sweetness of a 5% sucrose solution and of a sample containing 5% of sucrose and an amount of the test substance or of the test extract, was determined by a group of experts (grade 1 [not sweet] to grade 10 [extremely sweet]). The evaluation was made as a calculation of the reduction (in %) of the sweetness sensation from the averages of the assessments of the sucrose solution or of the sucrose and the test substance or of the solution containing the test extract.

(19) TABLE-US-00007 Extract % Enhancement concentration Sweetness sensation of the (ppm)/phyllodulcin (1-10) sweetness Substance/extract concentration (ppm) without with sensation Ethanolic extract from 10/0.7 5.0 0.8 5.4 1.5 8% Example 2 (contains 7.2% phyllodulcin) ditto 25/1.75 5.6 1.2 5.9 1.1 6% ditto 50/3.5 5.3 1.3 6.9 1.5 31% (p < 0.01) ditto 100/7 5.5 0.9 7.4 1.3 34% (p < 0.001) ditto 110/7.7 5.6 1.7 7.5 1.8 33% (p < 0.01) ditto 200/14.sup. 5.1 0.8 7.6 1.3 49% (p < 0.001) Ethyl acetate extract 55/7.7 4.9 1.1 6.9 1.3 42% (p < 0.001) from Example 3 (contains 14.4% phyllodulcin) Ethanolic/aqueous 145/7.7 5.3 1.6 6.9 1.5 30% (p < 0.01) extract from Example 4 (contains 5.3% phyllodulcin) Ethanolic/aqueous 240/7.7 5.3 1.1 7.6 1.6 43% (p < 0.001) extract from Example 5 (contains 3.2% phyllodulcin)

(20) It is possible to detect a very good sweetness enhancement even with the concentration of approximately 100 ppm ethanolic extract, which is not sweet per se, from Example 2, corresponding to less than 10 ppm of phyllodulcin. Purely by way of calculation, it would be expected that a 5% sucrose solution (corresponds sensorially by definition to 5% sucrose equivalents) which contains 100 ppm of ethanolic extract from Example 2, would produce additively a sweetness of approximately 5.8 sucrose equivalents. However, the sensory assessment of a mixed solution of this type of 5% sucrose with 100 ppm of the extract according to the invention from Example 2 produced by the method described in the preliminary test, a sucrose equivalence of 7.7%, which corresponds to a synergy of more than 30% above the expected value.

Application Example 2: Reduced-Sugar Soft Drink

(21) Preparation A: comparative preparation with 10% sugar Preparation B: comparative preparation with 8% sugar Preparation C: comparative preparation with 8% sugar and neohesperidin dihydochalcone Preparations D-H: reduced-sugar preparations according to the invention with 8% sugar

(22) TABLE-US-00008 Use in % by weight Preparation Ingredient A B C D E F G H Sugar 10 8 8 8 8 8 8 8 Citric acid 0.15 0.15 0.15 0.15 0.15 0.15 0.15 0.15 Lemon flavoring 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 Neohesperidin- 0.0001 dihydrochalcone Extract from 0.011 0.005 0.005 0.005 0.005 Example 2, containing 7% phyllodulcin Phloretin 0.002 Hesperetin 0.001 Extract of Rubus 0.010 suavissimus, containing 5% by weight rubusoside based on the total weight of the extract Water Make up to 100

(23) The ingredients were mixed in the stated sequence and made up to 100% with water. The mixtures were poured into glass bottles and carbonized.

(24) The preparations were tested sensorially in blind duo tests. In this respect, the sweetness was assessed by experts using a grading of 1 [not sweet to 10 [extremely sweet].

(25) TABLE-US-00009 Comparison Between 1st Sweetness sensation Significance and 2nd (1-10) (n.s. = not samples 1st sample 2nd sample Change (%) significant) A and B 7.1 1.4 4.6 1.3 36% p < 0.001 A and C 6.3 1.2 4.6 1.9 28% p < 0.01 A and D 6.9 1.4 7.0 1.5 2% n.s. A and E 6.8 1.8 5.9 1.9 13% n.s. A and F 5.4 1.3 5.9 1.4 9% n.s. A and G 6.8 1.5 6.3 1.8 7% n.s. A and H 6.8 1.9 6.4 2.2 6% n.s.

(26) By omitting sugar (20% by weight, based on sucrose), a reduction in sweetness of approximately 36% was observed (preparations A and B).

(27) As comparison (preparation C), the known sweetener neohesperidin dihydrochalcone was used in a concentration which alone in water corresponds to approximately 0.5% sucrose equivalence (determined by the method mentioned in Application example 1, first part). Compared to Comparative example A, the sweetness of the comparative preparation C, reduced in sugar by %, could not be reproduced alone by 1 ppm of neohesperidin dihydrochalcone.

(28) By adding the extracts according to the invention on their own (preparations D and E) to the reduced-sugar preparation, the panelists were no longer able to detect any significant difference between the full sugar preparation and the relatively sugar-depleted preparation according to the invention (A as opposed to D or A as opposed to E); however, with the lower dosing (preparation E), it was still possible to detect a sweetness which was not completely reproduced.

(29) This means that the extracts according to the invention are better able to reproduce the sweetness of reduced-sucrose applications than conventional sweeteners in low dosings of less than 1% sucrose equivalent.

(30) However, by combining the lower dosing of 50 ppm of the extract of the invention according to Example 2 with known flavorings for sweetness enhancement (G, H), the sweetness could then be substantially reproduced or even more sweetness could be achieved by using extracts of Rubus suavissimus (F).

Application Example 3: Flavoring Mixtures, Containing Sweeteners

(31) TABLE-US-00010 Preparation (use in % by weight) Ingredient A B C D E F G H I Liquid sugar, 99.87 contains 80% sucrose Rebaudioside A 98% 80 70 70 60 70 73.5 Rebaudioside A 90% 90 Stevioside 95% 75 Extract of Hydrangea 0.10 20 20 20 10 10 20 20 dulcis according to Example 2 (ethanolic, 7.7% phyllodulcin) Extract of Hydrangea 10 dulcis according to Example 3 (ethyl acetate, 14.4% phyllodulcin) Extract of Rubus 25 suavissimus, containing 5% by weight rubusoside, e.g. from plant extract Phloretin 0.02 4 5 3.2 3.5 5 5 Hesperetin 0.01 1 5 0.8 1 4.9 1 Neohesperidin- 0.5 dihydrochalcone Homoeriodictyol- 16 sodium salt Vanillin, natural 0.1 Sugar distillate from 0.5 cane sugar (e.g. Treatt)

(32) The substances or solutions are mixed in the proportions stated above and are used thus. The typical dosing of preparation A in the finished product is from 7 to 15% by weight, based on the finished product; the typical dosing of preparations B to I is from 0.01 to 0.1, based on the finished product, and preferably from 0.03 to 0.06%.

Application Example 4: Spray-Dried Preparation as Semi-Finished Product for the Flavoring of Finished Products

(33) TABLE-US-00011 Use in % by weight Preparation Ingredient A B C D E F G H I Drinking water 60 60 60 60 60 60 60 60 60 Maltodextrin from wheat 10 25 25 25 25 25 25 25 25 Gum arabic 5 5 5 5 5 10 10 10 10 Flavoring mixture A from 25 Application example 3 Flavoring mixture B from 10 Application example 3 Flavoring mixture C from 10 Application example 3 Flavoring mixture D from 10 Application example 3 Flavoring mixture E from 10 Application example 3 Flavoring mixture F from 5 Application example 3 Flavoring mixture G from 5 Application example 3 Flavoring mixture H from 5 Application example 3 Flavoring mixture I from 5 Application example 3

(34) The drinking water is introduced into a container and the maltodextrin and gum arabic are dissolved therein. The flavoring mixtures are then emulsified into the carrier solution using a Turrax. The temperature of the spray solution should not exceed 30 C. The mixture is then spray-dried (set temperature at inlet 185-195 C., set temperature at outlet: 70-75 C.).

Application Example 5: Solutions of the Flavoring Mixtures

(35) The compositions of Application example 3 can also be taken up with water, propylene glycol, glycerol or ethanol or preferably with mixtures of the aforementioned solvents (for example water-propylene glycol, water-glycerol, water-ethanol, glycerol-ethanol, glycerol-propylene glycol, propylene glycol-ethanol) for example as a 1-20% solution, preferably a 2-20% solution, more preferably a 5% solution and are completely dissolved by gentle heating.

Application Example 6: Cola-Type Soft Drink

(36) TABLE-US-00012 Preparation (use in % by weight) Ingredient A B C D E F G H Saccharose 0 8 7 7 7 7 Glucose/fructose corn 8 7 syrup, containing 55% by weight of fructose Flavoring mixture A from 10 Application example 3 Flavoring mixture B from 0.05 Application example 3 Flavoring mixture C from 0.05 Application example 3 Flavoring mixture D from 0.05 Application example 3 Flavoring mixture E from 0.05 Application example 3 Flavoring mixture F from 0.05 Application example 3 Flavoring mixture G from 0.05 Application example 3 Flavoring mixture I from 0.05 Application example 3 Phosphoric acid 0.07 0.07 0.07 0.07 0.07 0.07 0.07 0.07 Citric acid 0.06 0.06 0.06 0.06 0.06 0.06 0.06 0.06 Caramel 0.14 0.14 0.14 0.14 0.14 0.14 0.14 0.14 Caffeine 0.01 0.01 0.01 0.01 0.01 0.01 0.01 0.01 .sub.Cola-type emulsion 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 drink Water Make up to 100%

(37) The ingredients were mixed in the stated sequence, poured into bottles and carbonized.

Application Example 7: Iced Tea Drink

(38) TABLE-US-00013 Preparation (use in % by weight) Ingredient A B C D E F G H Flavoring mixture A from 6 Application example 3 Flavoring mixture F from 0.03 0.03 0.03 Application example 3 Flavoring mixture G from 0.03 0.03 Application example 3 Flavoring mixture H from 0.03 0.03 Application example 3 Citric acid 0.15 0.12 0.15 0.12 0.15 0.12 0.15 0.12 Ascorbic acid 0.02 0.02 0.02 0.02 0.02 0.02 0.02 0.02 Black tea extract 0.15 0.15 0.15 0.15 Green tea extract (at 0.1 0.1 0.33 0.33 least 50% polyphenols) Lemon-type natural 0.1 0.1 0.1 0.1 flavoring Peach-type natural 0.07 0.07 0.07 0.07 flavoring Water Make up to 100%

(39) The ingredients were mixed in the stated sequence, poured into bottles and sterilized.

Application Example 8: Use in a Chewing Gum

(40) TABLE-US-00014 Part Ingredient Use in % by weight A Chewing gum base, Company Jagum T 30.00 B Sorbitol, pulverised 38.975 Isomalt (Palatinit GmbH) 9.50 Xylitol 2.00 Mannitol 3.00 Rebaudioside A 98% 0.20 Ethanolic extract from Example 2 0.02 Hesperetin 0.005 Emulgum (Colloides Naturels, Inc.) 0.30 C Sorbitol, 70% 14.00 Glycerol 1.00 D Mint flavoring 1

(41) Parts A to D are mixed and kneaded intensively. The raw mass can be processed into ready-for-use chewing gum, for example as thin strips.

Application Example 9: Sugar-Free Hard Caramels

(42) TABLE-US-00015 Content (%) Ingredient A B C D Palatinite, type M 75.00 74.00 75.50 75.00 Citric acid 1.0 0.5 Water 24.88 24.842 23.88 24.844 Yellow coloring 0.01 Red coloring 0.01 Blue coloring 0.01 0.01 Peppermint flavoring 0.1 0.1 Lemon flavoring 0.1 Red fruit flavoring 0.1 Rebaudioside A 98% 0.040 0.040 Extract from Example 2 0.010 0.005 0.010 0.005 Hesperetin 0.001 0.001 Phloretin 0.002

(43) Palatinite was mixed with water optionally after the addition of citric acid and the mixture was melted at 165 C. and then cooled to 115 C. The flavoring and the other ingredients were added and after being thoroughly mixed, the mixture was poured into moulds, removed from the moulds after solidifying and then packaged individually.

Application Example 10: Reduced-Sugar Steamed Pudding

(44) Preparation A, B: comparative preparations with full sugar content (A) and reduced sugar content (B)

(45) TABLE-US-00016 Preparation (amounts as % by weight) Ingredient A B C D E F Sucrose 7.8% 5.4% 5.4% 5.4% 5.4% 5.4% Starch 3.0% 3.0% 3.0% 3.0% 3.0% 3.0% Skimmed milk 1.5% 1.5% 1.5% 1.5% 1.5% 1.5% powder Aubygel MR50 0.5% 0.5% 0.5% 0.5% 0.5% 0.5% Vanilla bean extract, 0.1% 0.1% 0.1% 0.1% 0.1% 0.1% spray-dried, Symrise Extract from 0.01% 0.005% 0.005% 0.005% Example 2 Extract of Rubus 0.010% 0.005% suavissimus, containing 5% by weight rubusoside, e.g. from plant extract Hesperetin 0.001% 0.001% Phloretin 0.002% 0.002% Milk 1.5% fat Make up to 100% content

(46) The solids were introduced and stirred up with the milk. The mixture was heated to 95 C. for 2 minutes with thorough stirring, decanted and cooled to 5-8 C.

Application Example 11: Low-Fat Yoghurts

(47) Comparative Preparation with Sugar (A)

(48) Preparations according to the invention with sweetener mixture and extract from Example 2 (B-D)

(49) TABLE-US-00017 Preparation (amounts as % by weight) Ingredient A B C D Sucrose 10 8 6 Rebaudioside A 98% 0.050 Extract from Example 2 0.010 0.005 0.010 Extract of Rubus 0.010 suavissimus, containing 5% by weight rubusoside, e.g. from plant extract Hesperetin 0.001 0.001 0.001 Phloretin 0.002 Homoeriodictyol 0.005 sodium salt Yoghurt 0.1% fat Make up to 100%

(50) The ingredients were mixed and cooled at 5 C.

Application Example 12: Mixed Milk Drinks

(51) Comparative Preparations with Sugar (A)

(52) Preparations According to the Invention (B-D)

(53) TABLE-US-00018 Preparation (amounts as % by weight) Ingredient A B C D Sucrose 10 8 7 Fructose 0.5 Rebaudioside A 98% 0.040 Extract from Example 2 0.010 0.005 0.010 Extract of Rubus 0.010 suavissimus, containing 5% by weight rubusoside, e.g. from plant extract Hesperetin 0.003 0.002 0.005 Phloretin 0.002 Homoeriodictyol 0.002 sodium salt UHT milk, 1.5% fat Make up to 100%

(54) The ingredients were mixed, made up with milk, stirred thoroughly, poured into bottles and stored, chilled, at 5 C.

Application Example 13: Reduced-Sugar Tomato Ketchup

(55) Comparative Preparation with Sugar (A)

(56) Comparative Preparation with Reduced Sugar Content (B)

(57) Preparations According to the Invention (C-I)

(58) TABLE-US-00019 Preparation (amounts as % by weight) Ingredient A B C E F G H I Common salt 2 2 2 2 2 2 2 2 Starch, Farinex 1 1 1 1 1 1 1 1 WM 55 Sucrose 12 9.6 9.2 8.4 9.6 9.6 8.4 4.2 Tomato 40 40 40 40 30 30 30 30 concentrate 2 Glucose syrup 80 18 18 18 18 18 18 18 18 Brix Spirit vinegar 10% 7 7 7 7 3 3 3 3 Rebaudioside A 0.05 98% Extract from 0.01 0.005 0.005 0.01 0.005 0.01 Example 2 Extract of Rubus 0.01 suavissimus, containing 5% by weight rubusoside, e.g. from plant extract Hesperetin 2.5% 0.1 0.1 in 1,2-propylene glycol Phloretin 2.5% in 0.2 0.2 0.3 1,2-propylene glycol Water Make up to 100%

(59) The ingredients are mixed in the stated sequence and the finished ketchup is homogenized using an agitator, poured into bottles and sterilized.

Application Example 14: Reduced-Sugar Ice Cream

(60) Comparative Preparation with Sugar (A)

(61) Comparative Preparation with Reduced Sugar Content (B)

(62) Preparations According to the Invention (C-F)

(63) TABLE-US-00020 Preparation (content in % by weight) Ingredient A B C D E F Vegetable fat, 20.00 20.00 20.00 20.00 20.00 20.00 melting range 35-40 C. Sugar (Saccharose) 12.00 8.00 8.00 8.00 8.00 8.00 Skimmed milk powder 5.00 5.00 5.00 5.00 5.00 5.00 Glucose syrup 72% 5.00 5.00 5.00 5.00 5.00 5.00 dry matter Emulsifier SE 30 0.65 0.65 0.65 0.65 0.65 0.65 (Grindstedt Products, Denmark) Flavoring, 0.20 0.20 0.20 0.20 0.20 0.20 containing 0.1% diacetyl and 1% vanillin Extract from 0.01 0.005 0.01 0.005 Example 2 Extract of Rubus 0.010 suavissimus, containing 5% by weight rubusoside, e.g. from plant extract Hesperetin 2.5% in 0.10 0.10 1,2-propylene glycol Phloretin 2.5% in 0.05 0.05 1,2-propylene glycol Skimmed milk Make up to 100%

(64) The vegetable fat was heated to 58 C. Skimmed milk and glucose syrup were heated to 55 C. and sugar, skimmed milk powder as well as emulsifier and flavoring were added and the mixture was introduced into the vegetable fat. The mixture was homogenized using a through-flow high-pressure homogenizer (180/50 bar). The resulting mass was tempered for 1 minute at 78 C., then cooled to 2-4 C. and incubated at this temperature for 10 hrs for maturing. The matured mass was then filled into containers and stored frozen at 18 C.

Application Example 15: Ice Cream Suitable for Diabetics

(65) An ice cream suitable for diabetics was prepared from the following ingredients and filled into 95 ml portion tubs:

(66) concentrated, skimmed milk, fructose syrup, strawberry pieces and strawberry puree (15%), vegetable fat, diet chocolate chips (3.5% with soya lecithin emulsifier), whey product, beetroot juice, locust bean gum, guar gum, carrageen, emulsifier (E 471), gelatin, acidifying agent citric acid, 0.1% strawberry flavoring (containing 1% by weight of the extract from Example 2 and 1% by weight of phloretin), based on the total weight of the strawberry flavoring), carotene coloring.

(67) Nutritional Value (Per 95 ml):

(68) Protein 1.8 g, carbohydrates 13.3 g (of which fructose 9.5 g), fat 4.2 g.

Application Example 16: Diet Chocolate Based on Maltitol

(69) A chocolate suitable for diabetics was prepared from the following ingredients and poured into rectangular bars:

(70) maltitol, hazelnut mass, cocoa butter, skimmed milk powder, cocoa mass, inulin, concentrated butter, emulsifier soya lecithins, 0.1% vanilla flavoring (containing vanilla bean extract, vanillin and 1% by weight of the extract from Example 2 and 0.3% by weight of hesperetin, based on the total weight of the vanilla flavoring).

(71) Nutritional Value (Per 100 g):

(72) Protein 8 g, carbohydrates 43 g (of which maltitol 34 g), fat 34 g.

Application Example 17: Diet Chocolate Based on Fructose

(73) A chocolate suitable for diabetics was prepared from the following ingredients and poured into rectangular bars:

(74) cocoa mass, fructose, skimmed milk powder, cocoa butter, inulin, concentrated butter, emulsifier soya lecithin, walnuts, cooking salt, 0.1% vanilla flavoring (containing vanillin and 1% by weight of the extract from Example 2 and 0.2% by weight of hesperetin and 1% by weight of homoeriodictyol sodium salt, based on the total weight of the vanilla flavoring).

(75) Nutritional Value (Per 100 g):

(76) Protein 8.8 g, carbohydrates 34 g (of which fructose 23 g, lactose 7.5 g, saccharose 1.4 g), fat 36 g; dietary fiber 18.5 (of which 12.2 g inulin); sodium: 0.10 g. Cocoa content at least 50% by weight.

Application Example 18: Reduced-Sugar Musli Mixture

(77) TABLE-US-00021 Preparation (content in % by weight) Ingredient A B Oat flakes 17.00 18.90 Crunchy oat flake clusters 10.00 12.00 Rice Crispies 16.90 17.80 Cornflakes 16.50 17.50 Currants 3.50 3.50 Hazelnuts, chopped 2.50 2.50 Glucose syrup from wheat, DE 30 9.50 9.50 Saccharose 20.00 14.00 Water 4.00 4.00 Citric acid powder, anhydrous 0.10 0.10 Flavoring, containing 1% by weight of 0.20 extract from Example 2 and 0.1% hesperetin, based on the flavoring

(78) Ingredients Nos. 1 to 6 are mixed in each case in a rotary drum (Mix 1). Ingredients Nos. 7 to 9 are each heated and ingredient No. 10 (in recipe B also ingredient No. 11) is added (Mix 2). Mix 2 is added to Mix 1 and then they are thoroughly mixed together. Finally, the resulting muesli mixture is turned out onto a baking tray and dried in an oven for 8 minutes at 130 C.

Application Example 19: Reduced-Sugar Fruit Gums

(79) TABLE-US-00022 Preparation (content in % by weight) Ingredient A B Water 23.70 25.70 Saccharose 34.50 8.20 Glucose syrup, DE 40 31.89 30.09 Iso Syrup C* Tru Sweet 01750 1.50 2.10 (Cerestar GmbH) Gelatine 240 Bloom 8.20 9.40 Polydextrose (Litesse Ultra, 24.40 Danisco Cultor GmbH) Yellow and red colorings 0.01 0.01 Citric acid 0.20 Cherry flavoring, containing 1% by 0.10 weight of extract from Example 2 and 0.3% by weight of phloretin, based on the flavoring

(80) Polydextrose is itself a non-sweet-tasting polysaccharide with a low calorific value.

Application Example 20: Choco-Cappuccino Ice Cream

(81) TABLE-US-00023 Preparation (content in % by weight) Ingredient A B Glucose-fructose syrup 14.10 14.10 Saccharose 10.00 7.50 Skimmed milk powder 5.00 5.00 Cream (36% fat content) 24.00 24.00 Emulsifier and stabilizer 0.50 0.50 Cremodan 709VEG (Danisco) Cocoa powder 5.975 5.975 Carrageenan 0.025 0.025 Water 40.20 42.50 Cappuccino flavoring 0.20 0.20 Containing 1% by weight of extract 0.20 from Example 2 and 1% by weight of homoeriodictyol sodium salt, based on the flavoring

Application Example 21: Gelatin Capsules for Direct Consumption

(82) TABLE-US-00024 Preparation (content in % by weight) Ingredient A B C Gelatin sheath: Glycerin 2.014 2.014 2.014 Gelatine 240 Bloom 7.91 7.91 7.91 Sucralose 0.065 0.065 0.065 Allura Red 0.006 0.006 0.006 Brilliant Blue 0.005 0.005 0.005 Core composition: Vegetable oil-triglyceride 79.55 68.70 58.95 (coconut oil fraction) Orange flavoring containing 10.0 20.0 28.65 1% by weight of extract from Example 2 and 1% by weight of homoeriodictyol sodium salt, based on the flavoring Rebaudioside A 98% 0.05 0.05 2-hydroxypropyl- 0.33 0.20 menthylcarbonate 2-hydroxyethylmenthyl- 0.20 1.00 carbonate (1R,3R,4S) menthyl-3- 0.55 0.50 carboxylic acid-N- ethylamide (WS-3) ()-Menthone glycerin 0.30 0.80 acetal (Frescolat MGA) Vanillin 0.07 0.10

(83) The gelatin capsules suitable for direct consumption were prepared according to WO 2004/050069 and had a diameter of 5 mm and the weight ratio of core material to sheath material was 90:10. The capsules opened in the mouth in less than 10 seconds and dissolved completely in less than 50 seconds.