EP3344068A1 - Foodstuff containing citrus products having added 4-hydroxyflavanones - Google Patents

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).

Description

 CITRUS PRODUCTS CONTAINING FOODS CONTAINING 4-HYDROXYFLAVANONE

FIELD OF THE INVENTION

 [0001] The invention is in the field of foodstuffs and relates to foods containing citrus and in particular orange products with added 4-hydroxyflavanones with the aim of reducing the unpleasant, in particular the sour and bitter taste of these foods.

STATE OF THE ART

[0002] Foodstuffs, in particular beverages, which are mainly produced from fruits of various citric species, play a very prominent role in the international food market. In particular, orange juice (Citrus x sinensis L. or Citrus x aurantium) in the form of juice or reconstituted juice from concentrate and foods based on orange juice such as nectars or fruit juice drinks should be mentioned. In addition to the typical citrus / orange aroma, a balanced sweetness in combination with an acidic taste impression and also a certain bitterness are decisive for the sensory quality of these drinks.

 In recent years, in the plantations, the infection of the fruit-bearing trees by the transmitted via leaf fleas Huanglongbing bacterium (for example, Liberobacter ssp., So-called "greening disease"), resulting in insufficiently developed and not ripe fruits Juice is generally less sweet and significantly more acidic than that derived from healthy fruit pulp, and the bitterness is much greater than the tolerated or necessary contribution, but up to a certain percentage of the infected but perishable fruit can be found in the juices or juice products are tolerated, but this is too large in particular, the acidic taste and bitterness for the consumer is usually clearly noticeable and leads to complaints.

Although it is known from EP 2494874 Bl (TROPICANA PRODUCTS) that a few ingredients of citrus fruits above an individual limit concentrations for the bitter and sour taste are responsible, but no specific teaching is given how these substances can be depleted accordingly to obtain flavourless products. Insofar as processes are known from the prior art with the aid of which such depletion could be carried out, this would also lead to other losses of ingredients or shifts in the flavor profile which are not tolerated. The simplest method is the addition of pipe or pipe Fructose, but this is not allowed in many applications for regulatory reasons.

 Therefore, it was the object of the present invention to find flavors or flavoring mixtures, which are able, even at low concentrations, the unpleasant, especially the sour and bitter taste of sour and bitter-tasting foods, and thereby citrus products in general and of orange products in particular to reduce or extinguish, and preferably also to enhance the sweet taste. In addition, the additives should be naturally occurring and preferably obtained from ingredients of the genus Citrus.

DESCRIPTION OF THE INVENTION

 A first aspect of the invention relates to foods containing

 (a) juice, marrow, flesh, peel or other ingredients of at least one citrus fruit,

(b) at least one 4-hydroxyflavanone of the formula (I)

 in which Ri is hydrogen or a hydroxy or a methoxy group and the carbon atom is present at the position (C2) marked with * in a (2S) or a (2R) configuration or in any mixture of the two configurations, and optionally

(c) other flavorings or flavorings,

with the proviso that component (b) is present in an amount sufficient to improve the acidic and / or bitter taste of component (a).

 The 4-hydroxyflavanones naringenin and eriodictyol, for example, are normally only present as glycosides bound in citrus products; e.g. as Narirutin (naringen-rutinoside) in the range of 1 to 50 ppm in orange juice (Gil-lzquierdo, A .; Gil, M.I., Ferreres, F., Tomas-Barberan, FA, "In Vitro Availability of Flavonoids and Other Phenolics in Orange Juice J. Agric.Food Chem., 2001, 49, (2), 1035-1041) or naringin (naringenin neohesperidoside) in lemons (Citrus lemon) or grapefruit (Citrus maxima) In contrast to lemon and lime, eriodictoyl has only been described in traces Homoeriodictyol has hitherto not been described in citrus fruits, especially in oranges.

Naringenin, hesperetin and eriodictyol in free form do not occur in a sufficient for the inventive effect sufficiently high concentration (> 5 ppm) in orange juices. So in Yanez, YES; Remsberg, C.M .; Miranda, N. D .; Vega Villa, KR; Andrews, PK; Davies, N. M., "Pharmacokinetics of selected chiral flavonoids: hesperetin, naringenin and erythrocytes. dictyol in rats and their content in fruit juices "Biopharmaceutics & Drug Disposition 2008, 29, (2), 63-82, describes naringenin in orange juices with a maximum of 0.5 ppm, eriodictyol is only found in trace amounts, homoeriodictyol has not been described Grapefruit juices, on the other hand, found a content of up to about 2.06 ppm for naringenin, but this is a regularly too low concentration for the unfolding of the masking effect, especially since 250 times the concentration of the very bitter naringin was found in the same juices in oranges is not present and is therefore not responsible for their bitterness In drinks containing lemon or lime juice, up to 28 ppm of eriodictyol was found, in contrast to orange drinks, which is naturally covered by an extremely strong sour taste.

 In this respect, it was surprising that the addition of an effective amount of at least 5 ppm of 4-hydroxyflavanones (based on the citrus component) acidic and bitter citrus products and especially Organgensaft entha delimiting foods significantly acidity and simultaneously reduces the bitterness perceived and in parallel caused a clear increase in sweetness. In particular, it is surprising that the perception of acid is perceived to be greatly diminished despite the unchanged pH value. The lowering of the sour taste is achieved without increasing the sweetness perception. FOOD

 The foods of the present invention are preferably beverages or desserts.

 Examples of citrus-containing beverages include the group formed by freshly squeezed, direct juices, reconstituted juices from juice concentrate, nectars, juice spritzers, juice-containing soft drinks, juice-containing dairy products, juice-containing carbonated beverages and juice-containing ice tea.

 Examples of citrus-containing desserts are in the group formed by yogurts, frozen ice-creams, sherbets, ice cream, creams, puddings, fillings for chocolates or biscuit products, jams and dried juice or fruit preparations.

CITRUS PRODUCTS

 The term citrus products for the purposes of the present invention, the juice, the marrow, the meat, the shells and all other ingredients of citrus fruits to understand; it is subsequently used as a synonym for group (a). Citrus fruits whose bitter and / or sour taste is to be improved include oranges, grapefruit, lemons, limes, mandarins and their mixtures.

In particular, group (a) comprises acidic and bitter orange products: orange varieties derived from fruits of the genus Citrus (Citrus x sinensis L. or Citrus x aurantium, Var. Hamlin, Valencia), especially by a proportion of early or emergency maturing Oranges derived from HLB-infected trees such as juices, juice concentrates, juice fractions with or without albedo, with or without pulp. Preferably apply to the citrus products minimum concentrations of special bitter substances and maximum concentrations of natural 4-hydroxyflavanones, namely

• at least 0.1 ppm and especially about 3 to about 5 ppm limonin

 • at least 5 ppm and especially 8 to 15 ppm polymethoxylated flavanones

At least 200 ppm and in particular 300 to 600 ppm hesperidin

 At most 2.5 ppm each and in particular at most 1 ppm naringenin, eriodictyol or homoeriodyctyol,

where the information relates in each case to component (a).

 Furthermore, the citrus products which form group (a) should have a pH in the range of 3 to 6.

4-HYDROXYFLAVANOLE

 [0020] 4-Hydroxyflavanols are known natural products obtainable by the relevant methods of organic chemistry. Preferably, as component (b) contain:

ictyol eriodictyol

The teaching of the present invention comprises the fact that the 4-hydroxyflavanols are present in any desired form of the respective stereoisomers. In a preferred embodiment of the invention, the foods contain 4-hydroxyflavanones of the formula (I) in which the (2S) and (2R) enantiomers in the weight ratio of 99: 1 to 1:99, and more preferably from about 90:10 to about 45:55.

 It is sufficient for a compensation of the acidic and / or bitter taste, if the 4-Hydroxyflavanols of the formula (I) based on the component (a) in amounts of about 5 to about 1000 ppm, and especially about 30 to about 250th ppm, and more preferably about 50 to about 100 ppm are present, added or selectively produced.

AROMAS

Optionally, the food may contain as component (c) further flavoring or flavoring preparations. These may be selected from substances for altering or masking an unpleasant taste impression and / or for enhancing a pleasant taste impression or flavoring agents are preferably selected from the following group: hesperetin as described in EP 2,368,442-Bl or EP 1,909,599-B1, hydroxybenzoic acid amides, such as for example 2,4-dihydroxybenzoic acid vanillylamide (in particular those as described in WO 2006/024587), 4-hydroxydihydrochalcones (preferably as described in US 2008/0227867 Al and WO 2007/107596), in particular phloretin and davidigenin, hesperetin as in WO 2007/014879, or extracts of Rubus suavissimus as described in US Provisional Application 61 / 333,435 (Symrise) and the patent applications based thereon, 3,7'-dihydroxy-4'-methoxyflavan isomers as described in EP 2,253,226, phyllodulcin isomers or phyllodulcine-containing extracts as described in EP 2,298,084-Bl, l- (2,4-dihydroxy-phen yl) -3- (3-hydroxy-4-methoxyphenyl) -propan-1-one as described in EP 2,353,403-Bl, neoisoflavonoids as described in EP 2,570,036-Bl, pellitorin and derived aroma compositions as in EP 2,008 530 AI, vanillylignan, in particular as described in the European patent application with the file reference EP 2,517,574, neoisoflavonoids as described in EP 2,570,035-Bl, neohesperidinedhydrochalcone, hesperetinedihydrochalcone, hesperidinedihydrochalcone, naringindihydro- chalcone, phloridzin, trilobatin, steviosides and / or rebaudiosides, in particular mixtures of various rebaudiosides as described in WO 2015 062,998, rubusosides as described in EP 2,386,211, mixtures of rubusoside isomers and homologues, mogroside, Abrusoside as in and / or balansins as in WO 2012 164,062 described.

Other flavoring or flavoring preparations may be selected from the list of volatile flavoring agents, e.g. Acetaldehyde, acetophenone, alpha-cadinol, alpha-copen, alpha-cubeben, alpha-humulene, alpha-pinene, alpha-terpinene, alpha-terpineol, anisaldehyde, benzaldehyde, benzophenone, beta-copaen, beta-cubeben, beta-cyclocitral, beta-elemen, beta-lonone, beta-myrcene, beta-ocimene, beta-pinene, butanol, butylacetate, camphene, caryophyllene, cis-4-decenal, cis-4-heptenal, cis-3-hexenal, cis 3-hexenol, cis-8-tetradecenal, citric, citronellol, citronellal, citronellyl acetate, cubenol, decanal, decanol, decyl acetate, (E, E) -2,4-decadienal, delta-3-carene, delta-cadinol, delta-carene, dihydronotkatone, dimethyl-anthranilate, dodecanal, dodecanol, dodecenal, elemole, ethoxyethylacetate, ethyl-2-hexanol, ethyl-2-methylbutyrate, ethyl-3-hydroxyhexanoate, ethyl-3-hydroxyoctanoate, ethyl acetate, ethyl butyrate, ethylcaprinate, Ethyl capronate, ethyl caprylate, ethyl crotonate, ethyl propionate, eucalyptol, eugenol, fenchol, gama-eudesmol, gamma-butyrolactones, gamma-terpinene, geraniol, geraniol, geranyl acetate, heptanal, heptane ol, heptyl acetate, hexanal, hexanol, hexyl acetates, isoamyl alcohol, isobutanol, isocascarillic acid, isopiperitole, isopulegol, lonenones, linalool, 12-methyltridecanal, menthadienol, menthadiene, methyl-3-hexanoate, methyl-3- hydroxyoctanoate, methytyrate, methylcapronate, methylcaprylate, methyldihydrojasmonth, methylsalicylate, (E, E) -2,4-nonadienal, neral, nerol, nerylacetate, nonanal, nonanol, nootkatene, nootkatol, nootkatone, octanal, octanol, octylacetate, pentanol, Perillaaldehyde, phenylethanol, piperitenone, rotundone, sinensal, terpinolene, trans-2-ethylhexenoate, trans-2-heptenal, trans-2-hexenal, trans-2-hexenal, trans-2-nonenal, trans-2-octenal, trans- 2- pentenal, 2-undecenal, undecanal, valencene, l-penten-3-οη in the form of any stereoisomers, enantiomers, positional isomers, diastereomers, cis / trans isomers or epimers of these substances.

[0025] AROMACO PREPARATIONS

A further embodiment of the invention relates to aroma preparations containing

(a) at least one 4-hydroxyflavanone of the formula (I) and

 (b) at least one other flavoring agent.

 The proportion of 4-hydroxyflavanones in general and naringenin, homoeriodictyol and / or eriodictyol in particular to these preparations can be from 0.1 to 99.9% by weight, preferably from about 0.5 to about 25% by weight. % and in particular about 1 to about 10 wt .-% amount. Further flavoring substances are the abovementioned substances. The flavorings may be encapsulated and / or adsorbed and / or emulsified, or incorporated into the formulation. CAPSULES

Both the 4-Hydroxyflavanols that form the group (b), as well as flavoring preparations containing these substances can be encapsulated and then added as capsules to food. Capsules are spherical aggregates to understand containing at least one solid or liquid core enclosed by at least one continuous shell. The fragrances may be encapsulated by coating materials and present as macrocapsules having diameters of from about 0.1 to about 5 mm or of microcapsules having diameters from about 0.0001 to about 0.1 mm.

Coating materials

 Suitable coating materials are, for example, starches, including their degradation products and chemically or physically generated derivatives (especially dextrins and maltodextrins), gelatin, gum arabic, agar-agar, ghatti gum, gellan gum, modified and unmodified celluloses, pullulan, Curdlan, carrageenans, alginic acid, alginates, pectin, inulin, xanthan gum and mixtures of two or more of these substances.

 The solid encapsulating material is preferably a gelatin (especially pork, beef, poultry and / or fish gelatin), which preferably has a threshold factor of greater than or equal to 20, preferably greater than or equal to 24. Among these substances, gelatin is particularly preferred because it is well available and can be obtained with different threshold factors.

 Also preferred are maltodextrins (especially based on cereals, especially corn, wheat, tapioca or potatoes), which preferably have DE values in the range of 10 to 20. Further preferred are celluloses (e.g., cellulose ethers), alginates (e.g., sodium alginate), carrageenan (e.g., beta-, jota, lambda, and / or kappa-carrageenan), gum arabic, curdlan, and / or agar agar.

 Also preferred are alginate capsules as described in detail in the following documents: EP 0389700 AI, US 4,251,195, US 6,214,376, WO 2003 055587 or WO 2004 050069 AI.

 In a further preferred embodiment, the shell of the capsules consists of melamine-formaldehyde resins or coacervation products of cationic monomers or biopolymers (such as chitosan) and anionic monomers such as (meth) acrylates or alginates.

Encapsulation process

The capsules are generally finely dispersed liquid or solid phases coated with film-forming polymers, in the preparation of which the polymers precipitate on the material to be coated after emulsification and coacervation or interfacial polymerization. According to another method, molten waxes are taken up in a matrix ("microsponge") which, as microparticles, can additionally be coated with film-forming polymers According to a third method, particles are coated alternately with polyelectrolytes of different charge ("layer-by-layer" process) ). The microscopic capsules can be dried like powder. In addition to monocyclic microcapsules, multinuclear aggregates, also called microspheres, are known which contain two or more cores distributed in the continuous shell material. Mono- or polynuclear microcapsules can also be enclosed by an additional second, third, etc., sheath. The shell may be made of natural, semisynthetic or synthetic consist of materials. Naturally, casing materials are, for example, gum arabic, agar agarose, agarose, maltodextrins, alginic acid or its salts, for example sodium or calcium alginate, fats and fatty acids, cetyl alcohol, collagen, chitosan, lecithins, gelatin, albumin, shellac, polysaccharides, such as starch or dextran, polypeptides, protein hydrolysates, sucrose and waxes. Semi-synthetic shell materials include chemically modified celluloses, in particular cellulose esters and ethers, for example cellulose acetate, ethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose and carboxymethylcellulose, and also starch derivatives, in particular starch ethers and esters. Synthetic envelope materials are, for example, polymers such as polyacrylates, polyamides, polyvinyl alcohol or polyvinylpyrrolidone.

 Examples of microcapsules of the prior art are the following commercial products (in parentheses is the shell material): Hallcrest Microcapsules (gelatin, gum arabic), Coletica Thalaspheres (marine collagen), Lipotec Millicapseln (alginic acid, agar-agar), Indutem unispheres (lactose, microcrystalline cellulose, hydroxypropylmethylcellulose); Unicerin C30 (lactose, microcrystalline cellulose, hydroxypropylmethylcellulose), Kobo Glycospheres (modified starch, fatty acid esters, phospholipids), Softspheres (modified agar-agar) and Kuhs Probiol Nanospheres (phospholipids) as well as Primaspheres and Primasponges (chitosan, alginates) and Primasys (phospholipids) ,

 Chitosan microcapsules and processes for their preparation are well known from the prior art [WO 01/01926, WO 01/01927, WO 01/01928, WO 01/01929].

Microcapsules with average diameters in the range of 0.0001 to 5, preferably 0.001 to 0.5 and in particular 0.005 to 0.1 mm, consisting of an enveloping membrane and a matrix containing the active ingredients can be obtained, for example, by

(a) preparing a matrix from gelling agents, cationic polymers and active compounds, (b) optionally dispersing the matrix in an oil phase,

 (c) treating the dispersed matrix with aqueous solutions of anionic polymers and optionally removing the oil phase.

 The steps (a) and (c) are interchangeable insofar as one uses instead of the cationic polymers in step (a) anionic polymers and vice versa.

It is also possible to produce the capsules by wrapping the active substance alternately with layers of differently charged polyelectrolytes (layer-by-layer technology). In this connection, reference is made to the European patent EP 1064088 Bl (Max Planck Society). INDUSTRIAL APPLICABILITY

 Another object of the invention relates to a method for reducing the acidic and / or bitter taste of citrus fruit products, comprising the following steps:

 (I) providing a citrus fruit product whose acidic and / or bitter taste is to be improved, and

(ii) adding or deliberately producing a flavor enhancing amount, preferably from about 5 to about 1000 ppm, and more preferably from about 30 to about 250 ppm - based on the citrus component - of at least one 4-hydroxyflavanone of the formula (I).

 Of course, instead of the 4-hydroxyflavanols it is also possible to use an aroma preparation containing them.

 Likewise claimed is the use of 4-hydroxyflavanols of the formula (I) or flavoring compositions containing them for improving the acidic and / or bitter taste of citrus fruit products, wherein here too the additional amount or the amount that is generated selectively, again preferably about 5 to about 1000 ppm, especially about 30 to about 250 ppm based on the citrus component.

As far as the preferred selection of components and additives and quantities have been made above, these are also valid for the method according to the invention and the use with, without that it requires a repetition.

EXAMPLES

EXAMPLES 1 to 5

Masking of acid perception and bitterness in orange juice obtained from early ripening and / or HLB-infected fruits with at least 5 ppm limonin

 For the experiments, a commercial orange juice was used, which contains 7.8 ppm of limonin after analysis and was regularly assessed by the panellists as too bitter. The panellists (n = 6) rate the three attributes "sweet", "bitter" and "sour" on an unstructured scale of 0 (no taste) - 10 (strong taste) .The panellists received orange juice in a sample alone, in another sample, the orange juice was added to an amount of 4-hydroxyflavanone listed in the table, the order was arbitrary and not known to the panellists, Table 1 below summarizes the results of the tests for 6 panellists.

Table 1

 Tasty rating

As the examples show, naringenin, at the inherently low concentration of 20 ppm, leads to a marked reduction of the bitter taste, reduction of the acid impression and at the same time an increase in the sweetness impression and improvement of the overall flavor profile of the tested orange juice. In the following Table 2, the results are reproduced with the addition of eriodictyol. Table 2

 Tasty rating

As the examples show, eriodictyol at the very low concentration of 10 ppm also leads to a strong reduction of the bitter taste, lowered acid perception and increased sweetness impression and therefore improves the overall taste profile of the tested orange juice. In the following Tables 3 and 4, the results are shown with addition of Homoeridictyol Na salt.

Table 3

 Tasty rating

As the examples show Homoerictyol sodium salt already in an amount of 30 ppm leads to significant reduction of the bitter taste, reduces the acidity and does not influence the sweetness impression here. At 50 ppm, in particular, acid perception is even more strongly influenced and therefore improves the overall taste profile of the tested orange juice. The following Table 5 shows the results for eriodictyol and naringenin. Table 5

 Tasty rating

In combination experiments C and D, it is clear that the effects of the mixtures of homoeriodictyol and eriodictyol (1E-C) and naringenin and eriodictyol (1E-D) again produce significantly more favorable taste effects, in particular greatly reducing bitterness and acid perception; At the same time, the sweet perception of the drinks was significantly increased.

APPLICATION EXAMPLES FROM THE DRINKING AREA WITH ORANGE JUICE SHARE

 FORMULATION A

 Orange juice drink (all amounts are by weight)

 FORMULATION B

Pectin filling (all quantities are by weight) To prepare the formulation B, the dry substances are dissolved in water and boiled together with the pectin and sodium citrate for about 3-5 minutes at 106 ° C to a Brix value of 77-78 °. Thereafter, the orange juice concentrate and the flavors are stirred. After gentle cooling, the mass is rapidly filled into molds and cooled.

FORMULATION C

 Orange sorbet (all amounts are by weight)

To prepare the emulsifier and stabilizer are mixed with sugar and dissolved in water; Glucose syrup is added and dissolved. The mixture is then pasteurized and cooled. Into the mixture are added the flavor ingredients and the fruit juice concentrate, the pH is adjusted to 3.8-4.2 with 50% citric acid solution, and the preparation is frozen in an ice cream machine with 40-80% overrun.

Formulation D

 Herbal liqueur (all amounts are by weight)

Preparation: Dissolve the sugar with water. Continue to add ingredients and dissolve. Pasteurize and cool.

Formulation E

 Mixed beer drink with grapefruit (all amounts are by weight)

Preparation: Dissolve beer base with sugar and water. Add more ingredients and dissolve. Pasteurize and cool.

Claims

1. Foods containing

 (a) juice, marrow, flesh, peel or other ingredients of at least one citrus fruit,

 (b) at least one 4-hydroxyflavanone of the formula (I)

in which Ri is hydrogen or a hydroxy or a methoxy group and the carbon atom at the position (C2) marked with * is in a (2S) or a (2R) configuration or in any mixture of the two configurations, as well as possibly

 (c) other flavorings or flavorings,

 with the proviso that component (b) is present in an amount sufficient to improve the acidic and / or bitter taste of component (a).

2. Foodstuffs according to claim 1, characterized in that they are drinks or desserts.

 3. The food according to claim 2, characterized in that it is citrus-containing drinks, which are selected from the group consisting of freshly squeezed, direct juices, reconstituted juices from juice concentrate, nectars, juice spritzers, juice-containing soft drinks, juice-containing dairy products , juice-containing carbonated drinks and juice-containing ice tea.

 4. Foodstuffs according to claim 2, characterized in that they are citrus-containing desserts selected from the group consisting of yogurts, frozen ice-creams, sorbets, ice creams, creams, puddings, fillings for chocolates or biscuit products, Jams and dried juice or fruit preparations.

 5. Food according to at least one of claims 1 to 4, characterized in that the citrus fruits are selected from the group consisting of oranges, grapefruit, lemons, limes, mandarins and their mixtures.

6. Food according to at least one of claims 1 to 5, characterized in that juice, marrow, meat, peel or other ingredients of citrus fruits contain at least 0.1 ppm limonin.

7. Food according to at least one of claims 1 to 6, characterized in that juice, marrow, meat, peel or other ingredients of citrus fruits contain at least 5 ppm polymethoxylated flavanones.

 8. Food according to at least one of claims 1 to 7, characterized marked, that juice, marrow, meat, peel or other ingredients of citrus fruits contain at least 200 ppm hesperidin.

 9. Food according to at least one of claims 1 to 8, characterized in that juice, marrow, meat, peel or other ingredients of citrus fruits contains at most 2.5 ppm naringenin, eriodictyol or Homoeriodictyol.

Foodstuff according to at least one of claims 1 to 9, characterized in that it contains as component (b) at least one 4-hydroxyflavanone of formula (I) selected from the group consisting of naringenin, homoeriodictyol and eriodictyol including the respective stereoisomers.

 11. Foodstuffs according to at least one of claims 1 to 10, characterized in that they contain 4-hydroxyflavanones of the formula in which the (2S) - and

(2R) enantiomers in a weight ratio of 99: 1 to 1:99.

 12. A food according to any one of claims 1 to 11, characterized in that they contain based on juice, pith, meat, peel or other ingredients of citrus fruits about 5 to about 1000 ppm at least one 4-hydroxyflavanone of the formula (I).

 13. Flavoring preparation containing

 (a) at least one 4-hydroxyflavanone of the formula (I) and

 (b) at least one other flavoring agent.

 14. A process for reducing the acidic and / or bitter taste of citrus fruit products, comprising the following steps:

 (I) providing a citrus fruit product whose acidic and / or bitter taste is to be improved, and

 (ii) adding or selectively producing a taste-improving amount of at least one 4-hydroxyflavanone of the formula (I) or an aroma preparation containing the same.

 15. Use of 4-hydroxyflavanones of the formula (I) or a flavoring preparation containing them, for improving the acidic and / or bitter taste of citrus fruit products.