# US 10,869,493 B2 · Reduced-sweetener products, flavoring mixtures for said reduced-sweetener products and process for the production of products of this type

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- Number: US 10,869,493 B2
- Document ID: US10869493B2
- Status: Granted
- Kind: B2
- Application number: 16/815,212
- Filed: 2020-03-11
- Published: 2020-07-02
- Granted: 2020-12-22
- Earliest claimed: 2009-08-28
- Assignees: Symrise AG
- Applicants: Symrise AG
- Inventors: Katharina Reichelt; Jakob Peter Ley; Petra Hoffmann-Lücke; Maria Blings; Susanne Paetz; Thomas Riess
- Web page: https://patentgrep.com/patent/US10869493B2

## CPC

- A23L 2/60: Sweeteners
- A23G 1/32: characterised by the composition {containing organic or inorganic compounds}
- A23G 1/48: containing plants or parts thereof, e.g. fruits, seeds or extracts (containing gums A23G1/40)
- A23G 3/36: characterised by the composition {containing organic or inorganic compounds}
- A23G 3/48: containing plants or parts thereof, e.g. fruits, seeds, extracts (containing gums A23G3/42)
- A23G 4/06: characterised by the composition {containing organic or inorganic compounds}
- A23G 4/068: {containing plants or parts thereof, e.g. fruits, seeds, extracts (containing gums A23G4/10)}
- A23G 9/32: characterised by the composition {containing organic or inorganic compounds}
- A23G 9/42: containing plants or parts thereof, e.g. fruits, seeds, extracts (containing gums A23G9/34)
- A23L 7/10: Cereal-derived products
- A23L 27/30: Artificial sweetening agents
- A23L 27/63: {Ketchup}
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B)
- A23G: COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## 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

### Claim 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).

### Claim 2 (depends on 1)

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.

### Claim 3 (depends on 1)

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).

### Claim 4 (depends on 2)

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.

### Claim 5 (depends on 1)

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

### Claim 6 (depends on 1)

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.

### Claim 7 (depends on 1)

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

### Claim 8 (depends on 6)

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.

### Claim 9 (depends on 6)

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.

### Claim 10 (depends on 1)

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.

### Claim 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.

### Claim 12 (depends on 11)

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.

### Claim 13 (depends on 11)

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).

### Claim 14 (depends on 12)

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.

### Claim 15 (depends on 11)

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

### Claim 16 (depends on 11)

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.

### Claim 17 (depends on 11)

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

### Claim 18 (depends on 17)

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.

### Claim 19 (depends on 16)

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.

### Claim 20 (depends on 11)

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.