# US 2023/0054857 A1 · Flavonoid compositions and related uses

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- Number: US 2023/0054857 A1
- Document ID: US20230054857A1
- Status: Published application
- Kind: A1
- Application number: 17/790,630
- Filed: 2021-02-02
- Published: 2023-02-23
- Earliest claimed: 2020-02-04
- Assignees: Firmenich SA
- Applicants: Firmenich SA
- Inventors: Eva MUELLER; Wolfgang FIEBER; Barbara BUCHS
- Web page: https://patentgrep.com/patent/US20230054857A1

## CPC

- A23L 2/52: Adding ingredients (adding preservatives A23B70/10)
- A23L 33/105: Plant extracts, their artificial duplicates or their derivatives
- A23C 9/1307: {Milk products or derivatives; Fruit or vegetable juices; Sugars, sugar alcohols, sweeteners; Oligosaccharides; Organic acids or salts thereof or acidifying agents; Flavours, dyes or pigments; Inert or aerosol gases; Carbonation methods}
- A23C 9/152: containing additives (fermented milk preparations containing additives A23C9/13)
- A23C 9/156: Flavoured milk preparations {; Addition of fruits, vegetables, sugars, sugar alcohols or sweeteners}
- A23L 2/56: Flavouring or bittering agents (sweeteners A23L2/60)
- A23L 2/60: Sweeteners
- A23L 27/84: {Flavour masking or reducing agents}
- A23V 2002/00: Food compositions, function of food ingredients or processes for food or foodstuffs
- A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B)
- A23C: DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; PREPARATION THEREOF (preservation thereof A23B11/00)
- A23V: INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION

## Abstract

The present disclosure generally relates to the use of certain compounds, such as anthocyanins, saponins, or combinations thereof, at low concentrations to improve the aqueous solubility of flavonoid compounds. Thus, in certain aspects, the disclosure provides aqueous compositions including flavonoid compounds, such as naringenin or phloretin, and one or more compounds selected rom anthocyanin compounds, saponins, and combinations thereof. In related aspects, the disclosure provides methods and uses of certain compounds, such as anthocyanins, saponins, or combinations thereof, to enhance the aqueous solubility of flavonoid compounds. In related aspects, the disclosure provides methods to maintain the stability of a supersaturated aqueous solution of flavonoid compounds, for example, by increasing the kinetic stability of such supersaturated aqueous solutions. In some further embodiments of the foregoing aspects, the aqueous compositions are used to make flavored articles, such as beverage or dairy products, that contain concentration of surfactants, co-solvents, hydrotropes, or complexing agents below the typical taste-affecting thresholds in humans.

## Claims

### Claim 1

A method of increasing aqueous solubility of a flavonoid compound, the method comprising introducing to an aqueous medium comprising a flavonoid composition one or more anthocyanin compounds, saponin compounds, or any combinations thereof, to increase an aqueous solubility of the flavonoid compound, wherein a molar ratio of the one or more anthocyanins, saponin compounds, or any combinations thereof, to the flavonoid compound in the aqueous medium ranges from 1:50 to 50:1.

### Claim at position 2

2-6. (canceled)

### Claim 7 (depends on 1)

The method of claim 1, wherein the method comprises introducing one or more saponin compounds in combination with the flavonoid compound to the aqueous medium.

### Claim 8 (depends on 7)

The method of claim 7, wherein the aqueous medium further comprises one or more sweeteners.

### Claim 9 (depends on 7)

The method of claim 7, further comprising one or more additional taste-modifying compounds, such as sweetness-enhancing compounds, umami-enhancing compounds, kokumi-enhancing compounds, bitter-reducing compounds, sourness-reducing compounds, and any combinations thereof.

### Claim 10 (depends on 1)

The method of claim 1, wherein the anthocyanin composition is a plant extract, such as an extract of one or more plants selected from the group consisting of blueberry, bilberry, cranberry, lingonberry, blackberry, black raspberry, red raspberry, blackcurrant, cherry, eggplant, black rice, black corn, black soybean, ube, Okinawan sweet potato, red cabbage, violet, peach, apple, and any combinations thereof.

### Claim 11 (depends on 1)

The method of claim 1, comprising introducing one or more anthocyanin compounds to the aqueous medium, wherein the one or more anthocyanin compounds are compounds of formula (I):
wherein:
R1, R2, R3, R4, R5, and R6 are each independently —H, —OH, or —OCH3; and
R7 is —H or a glucosyl moiety.

### Claim 12 (depends on 11)

The method of claim 11, wherein the one or more anthocyanin compounds comprise cyanidin.

### Claim 13 (depends on 11)

The method of claim 11, wherein the flavonoid compound is hesperetin, naringenin, phloretin, rhoifolin, or any combinations thereof.

### Claim 14 (depends on 1)

The method of claim 1, wherein the aqueous medium is a dairy product.

### Claim 15 (depends on 1)

The method of claim 1, wherein the aqueous medium comprises any surfactants, co-solvents, hydrotropes, or complexing agents, each at a concentration of no more than 1000 ppm.