# US 10,765,134 B2 · Foodstuff containing citrus products having added 4-hydroxyflavanones

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- Number: US 10,765,134 B2
- Document ID: US10765134B2
- Status: Granted
- Kind: B2
- Application number: 15/755,599
- Filed: 2015-09-01
- Published: 2019-01-24
- Granted: 2020-09-08
- Earliest claimed: 2015-09-01
- Assignees: Symrise AG
- Applicants: Symrise AG
- Inventors: Johannes Kiefl; Susanne Paetz; Jakob Ley; Gerhard Krammer; Thomas Riess; Kathrin Langer; Günter Kindel; Morine Verwohlt
- Web page: https://patentgrep.com/patent/US10765134B2

## CPC

- A23L 19/07: {Fruit waste products, e.g. from citrus peel or seeds}
- A23L 27/13: {from citrus fruits}
- A23L 27/2052: {having oxygen or sulfur as the only hetero atoms}
- A23L 27/84: {Flavour masking or reducing agents}
- A23L 27/86: {Addition of bitterness inhibitors}
- A23V 2002/00: Food compositions, function of food ingredients or processes for food or foodstuffs
- A23V 2200/16: Taste affecting agent
- A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B)
- 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 invention relates to a foodstuff, containing: a) juice, pith, flesh, skins; or other constituents of at least one citrus fruit, b) at least one 4-hydroxyflavanone of the formula (I), in which R1 represents hydrogen or a hydroxy group a or methoxy group and the carbon atom at the position (C2) designated by * is present in a (2S) or a (2R) configuration or in any mixture of the two configurations, and also, if applicable, c) further flavorings or flavoring preparations, with the proviso that the constituent (b) is present in a sufficient quantity to improve the acidic and/or bitter taste of the constituent (a).

## Claims

### Claim 1

A food product consisting essentially of:
(a) juice, flesh or peels or other components of premature and/or HLB-infected oranges, wherein the juice, flesh or peels or other components of the premature and/or HLB-infected oranges comprise:
at least 0.1 ppm of limonin;
at least 5 ppm of polymethoxylated flavanones;
at least 200 ppm of hesperidin; and
a maximum of 2.5 ppm of naringenin, eriodictyol, or homoeriodictyol;
(b) at least one 4-hydroxyflavanone of formula (I)
wherein R1 denotes hydrogen or a hydroxy or methoxy group and the carbon atom at the position (C2) marked by * is present in a (2S) or a (2R) configuration or in an arbitrary mixture of both configurations; and
(c) further flavouring agents or flavour preparations;
provided that component (b) is present in a sufficient amount to improve the sour and bitter taste of component (a).

### Claim 2 (depends on 1)

The food product according to claim 1, characterized in that the food product is a food or a dessert.

### Claim 3 (depends on 2)

The food product according to claim 2, characterized in that the food product is a drink selected from the group consisting of freshly pressed, direct juices, reconstituted juices from juice concentrate, nectars, saftschorle, refreshing drinks containing juice, milk products containing juice, carbonised drinks containing juice, and iced tea containing juice.

### Claim 4 (depends on 2)

The food product according to claim 2, characterized in that the food product is a dessert selected from the group consisting of a yoghurt, a frozen ice product, a sorbet, ice cream, cream, pudding, filling for chocolate or cookie products, a jam, and a dried juice or fruit preparation.

### Claim 5 (depends on 1)

The food product according to claim 1, characterized in that it contains at least one 4-hydroxyflavanone of formula (I) as component (b), which is selected from the group consisting of naringenin, homoeriodictyol and eriodictyol, including the respective stereoisomers.

### Claim 6 (depends on 1)

The food product according to claim 1, characterized in that it contains 4-hydroxyflavanones of formula (I), wherein the (2S)- and (2R)-enantiomers are present in a weight ratio of 99:1 to 1:99.

### Claim 7 (depends on 1)

The food product according to claim 1, characterized that the juice, flesh or peels or other components comprise naringenin.

### Claim 8 (depends on 1)

The food product according to claim 1, characterized that the juice, flesh or peels or other components comprise eriodictyol.

### Claim 9 (depends on 1)

The food product according to claim 1, characterized that the juice, flesh or peels or other components comprise homoeriodictyol.

### Claim 10

A method for reducing the sour and bitter taste of premature and/or HLB-infected oranges consisting essentially of:
(i) providing juice, flesh or peels or other components of premature and/or HLB-infected oranges; and
(ii) adding an amount sufficient to improve the sour and bitter taste of the juice, flesh or peels or other components of the premature and/or HLB-infected oranges of at least one 4-hydroxyflavanone of formula (I),
wherein R1 denotes hydrogen or a hydroxy or methoxy group and the carbon atom at the position (C2) marked by * is present in a (2S) or a (2R) configuration or in an arbitrary mixture of both configurations; and
(iii) adding further flavouring agents or flavour preparations;
provided that component (b) is present in a sufficient amount to improve the sour and bitter taste of component (a).