Use of naringenin for improving taste quality of phloretin

Abstract

To provide a use of naringenin for improving the taste quality of phloretin, a method for improving the taste quality of phloretin, and aroma compositions containing naringenin and phloretin as well as semi-finished and finished products containing the aroma compositions.SOLUTION: Naringenin is used in an amount of 10 ppm to 100 ppm, preferably of 15 ppm to 80 ppm, most preferably of 20 ppm to 50 ppm, based on the total amount of the preparation, with the proviso that in a case where naringenin is used for decreasing the bitterness of or in a preparation comprising 30 ppm phloretin, naringenin is not contained in an amount of 30 ppm, in each case based on the total amount of the preparation, and in a case where naringenin is used for improving the mouthfeel of a preparation comprising 30 ppm phloretin, naringenin is not contained in an amount of 30 ppm, in each case based on the total amount of the preparation.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention relates to the use of naringenin for improving the taste of phloretin.Furthermore, the present invention relates to a method for improving the taste of phloretin.Furthermore, the present invention relates to an aroma composition containing naringenin and phloretin, and semi-finished products and finished products containing the aroma composition. [Background technology]

[0002] Foods or beverages with a high sugar content (mainly sucrose, lactose, glucose, or fructose, or mixtures thereof) and therefore a sweet taste are usually highly preferred by consumers. It is generally known that the consumption of a high content of easily metabolizable carbohydrates, such as the sugars mentioned above, can significantly increase blood glucose levels, potentially leading to the formation of fatty deposits if consumed excessively. This, if left uncontrolled and unaddressed, can lead to overweight, obesity, insulin resistance, late-onset diabetes, and related secondary diseases. In particular, many of the carbohydrates mentioned above can be broken down by certain types of bacteria in the oral cavity into lactic acid, which can attack tooth enamel in adolescents and adults, leading to the formation of pits or inflammation, thus affecting dental health.

[0003] Therefore, the goal is to reduce the amount of sugar in foods and beverages, preferably to the minimum level that consumers do not notice a difference in taste. One possibility for preserving sweetness is the use of sweeteners. These are substances that have no or only a very low caloric value themselves and at the same time produce a strong sweetness impression. These substances are usually non-cariogenic (review: Non-Patent Document 1). Some of them, known as bulk sweeteners, such as sorbitol, mannitol, or other sugar alcohols, can partially replace the residual food technology-related properties of sugar, but infrequent consumption can lead to osmotically induced digestive problems in some people. Due to their low concentrations when used, non-nutritive high-intensity sweeteners are well suited to providing sweetness to foods. Nevertheless, they often exhibit taste-related challenges as a result of time-intensity profiles that are not similar to sugars (e.g., sucralose, stevioside, cyclamate), bitter and / or astringent aftertastes (e.g., aceflufam K, saccharin) or additional undesirable flavor impressions (e.g., ammonium glycyrrhetinate).

[0004] One of the sweeteners with high potential is phloretin, which is described in U.S. Patent No. 5,629,999. Phloretin imparts a strong sweetness to a composition when incorporated into the composition, even at low levels. It has been observed that the use of phloretin may introduce additional undesirable tastes into the composition in which it is used.

[0005] Bitter taste is produced by specific substances that bind to special bitter receptors on taste cells (found in taste buds on the tongue) and trigger signals in a subsequent neurochemical cascade that result in a defensive response and a negative taste impression (see Non-Patent Document 2).

[0006] One strategy to mask this bitter aftertaste is the use of taste modifiers that do not themselves exhibit a specific taste perception but are able to minimize the so-called "off-notes" that describe undesirable tastes in the composition. One such substance is naringenin, a flavonoid naturally derived from citrus fruits. The prior art, e.g., U.S. Patent No. 5,949,999, has already described the use of naringenin for taste modulation in the context of citrus products, in particular for enhancing the sweetness of the composition.

[0007] It has already been described in Patent Document 3 that naringenin can potentially affect the taste of phloretin in a composition. It is disclosed that this effect is observed in an example of a composition containing 30 ppm phloretin and 30 ppm naringenin.

[0008] In the aroma industry, specific formulation regions are often desired or required. In complex aroma compositions, the concentration regions often depend not only on a single compound but also on the interaction of various sweeteners, flavors and / or taste modifiers, and therefore must be perfectly balanced.

[0009] A first object of the present invention was therefore to find new concentration ranges in which the undesirable taste properties of phloretin can be adjusted or masked in an advantageous manner.

[0010] Other objects will become apparent in view of the appended claims and the following description. [Prior art documents] [Patent documents]

[0011] [Patent Document 1] International Publication No. 2007 / 014879 [Patent Document 2] International Publication No. 2017 / 036518(A1) [Patent Document 3] International Publication No. 2017 / 092796(A1) [Non-patent literature]

[0012] [Non-Patent Document 1] Valerie B. Duffy, Madeleine Sigman-Grant, Margaret A. Powers, Denise Elmore, Esther F. Myers, Diane Quagliani, Marie Spano, Kimberly F. Stitzel, Sue Taylor, Robert Earl, and Sonja Connor, Journal of the American Dietetic Association, Volume 104, Number 2, pages 255-275 (2004). [Non-patent document 2] Wolfgang Meyerhof, Reviews of Physiology, Biochemistry and Pharmacology, Vol. 154, pp. 37-72 (2005) Summary of the Invention [Means for solving the problem]

[0013] The first object is to provide a method for the use of naringenin to reduce bitterness and / or improve mouthfeel and / or reduce astringency and / or improve sweetness intensity of or in a preparation containing phloretin, Naringenin is used in an amount of 10 ppm to 100 ppm, preferably 15 ppm to 80 ppm, and most preferably 20 ppm to 50 ppm, based on the total amount of the preparation; As a prerequisite, When naringenin is used to reduce the bitterness of or in a preparation containing 30 ppm phloretin, the naringenin is not contained in an amount of 30 ppm, in each case based on the total amount of the preparation; When naringenin is used to improve the mouthfeel of a preparation containing 30 ppm phloretin, naringenin is not contained in an amount of 30 ppm, in each case based on the total amount of the preparation. This was resolved by using naringenin.

[0014] In one embodiment of the present invention, naringenin is used to reduce the bitterness of or in a preparation comprising phloretin, as defined above. In another embodiment, naringenin is used to reduce the bitterness and improve the mouthfeel of or in a preparation comprising phloretin, as defined above. Another embodiment relates to the use of naringenin to reduce the bitterness, improve the mouthfeel, and reduce astringency of or in a preparation comprising phloretin. One embodiment of the present invention relates to the use of naringenin to reduce the bitterness, improve the mouthfeel, reduce astringency, and improve sweetness of or in a preparation comprising phloretin. In yet another embodiment, naringenin is used to improve the mouthfeel of or in a preparation comprising phloretin. Another embodiment relates to the use of naringenin to improve the mouthfeel and reduce astringency of or in a preparation comprising phloretin. Yet another embodiment relates to the use of naringenin to improve the mouthfeel, reduce astringency, and improve sweetness of or in a composition comprising phloretin. One embodiment of the present invention relates to the use of naringenin to reduce the astringency of or in a composition comprising phloretin. In yet another embodiment, naringenin is used to reduce the astringency and improve the sweetness of a composition containing phloretin, and in another embodiment, the present invention relates to the use of naringenin to improve the sweetness of a composition containing phloretin.

[0015] "Reducing bitterness" in the context of the present invention should be understood as a perceptible positive change in the bitterness of a preparation compared to a reference preparation not containing naringenin, meaning that the reference preparation is perceptibly more bitter than the preparation defined in the course of the present invention.

[0016] In the context of the present invention, "improved mouthfeel" should be understood as a fuller taste perception, with a richer taste sensation in the mouth, compared to a reference preparation that does not contain naringenin. The taste perception "mouthfeel" is known as "kokumi" in Japan. This taste is thought to be caused by degraded protein fragments that form in foods or beverages over long processing times. These protein fragments themselves do not exhibit a specific taste sensation, but can stimulate the overall taste perception by binding to specific receptors in the oral cavity.

[0017] In the context of the present invention, "reducing astringency" should be understood as a reduction in the furry mouthfeel in a preparation compared to a reference preparation that does not contain naringenin. The "gustatory" perception of astringency is not an actual taste, but more like a "painful" perception that is detected by the trigeminal nerve and triggers the astringent sensation on the tongue or in the oral cavity. The perception of astringency is often also described as a dull sensation in the mouth.

[0018] "Improving sweetness" in the context of the present invention should be understood as an increase in the sweetness perception of a preparation compared to a reference preparation not containing naringenin.

[0019] Those skilled in the art are aware of methods and experimental testing procedures for assessing differences in taste perception between two preparations. A commonly used testing procedure is the taste testing of two preparations with different compositions by a panel of trained tasters.

[0020] Surprisingly, it has been found that naringenin can reduce the bitterness of phloretin in various formulation ranges of naringenin between 10 ppm and 100 ppm of or in compositions containing phloretin.

[0021] One preferred embodiment of the present invention relates to the use according to the present invention, provided that if the preparation contains 30 ppm of phloretin, then naringenin is not contained in an amount of 30 ppm.

[0022] In the context of the present invention, the weight ratio of naringenin to phloretin in the preparation is preferably in the range of 1:5 to 5:1, preferably 1:3 to 3:1, more preferably 1:1.5 to 1.5:1.

[0023] Since the object of the present invention is to explore a new concentration range for improving the taste of phloretin, it is also very important to find various formulation ratios between naringenin and phloretin to provide more flexible formulations for achieving the effects of the present invention.

[0024] It has been found by the inventors of the present invention that naringenin can improve the above-defined taste perception of or in a composition comprising phloretin at various ratios of naringenin to phloretin.

[0025] It is particularly preferred if naringenin and phloretin are used in equal concentrations, resulting in a 1:1 weight ratio.

[0026] Furthermore, preferably, the preparation is selected from the group consisting of aroma compositions, preparations intended for nutritional, recreational or cosmetic or pharmaceutical purposes, and semi-finished products for producing such preparations.

[0027] Preferably, preparations intended for nutritional or recreational purposes are (low-calorie) baked goods (e.g. bread, dry biscuits, cakes, other baked goods), confectionery (e.g. mousse bar products, chocolate, chocolate bars, other products in bar form, fruit gums, dragées, hard and soft caramels, chewing gum), non-alcoholic drinks (e.g. cocoa, coffee, green tea, black tea, (green, red) tea drinks enriched with (green, red) tea extracts, rooibos tea, other herbal teas, fruit-containing soft drinks, isotonic drinks, refreshing drinks, nectars, fruit and vegetable juices, fruit or vegetable juice preparations), instant drinks (e.g. instant cocoa drinks, instant tea drinks, instant coffee drinks), meat products (e.g. ham, fresh sausage or raw sausage preparations, spiced or marinated fresh or salted meat products), eggs or egg products (dried eggs, egg whites, egg yolks), cereal products (e.g. breakfast cereals, mousse bars, cooked ready-to-eat rice products), dairy products (e.g. high-fat or low-fat milk or non-fat milk drinks, rice pudding, yogurt, kefir, cream cheese, soft cheese, hard cheese, dried milk powder, whey, butter, buttermilk, ice cream, partially or fully hydrolyzed milk protein-containing products), products made from soy protein or other soy fractions (e.g., soy milk and products made therefrom, beverages containing isolated or enzymatically treated soy protein, beverages containing soy flour, preparations containing soy lecithin, fermented products such as tofu or tempeh or products made therefrom) products and mixtures with fruit preparations and optionally flavors), dairy-like preparations (milk-type, yogurt-type, dessert-type, ice cream) from high-protein plant materials (e.g. from oats, almonds, beans, lupins, lentils, broad beans, chickpeas, rice, canola seed materials), non-dairy drinks enriched with plant proteins, fruit preparations (e.g. jams, sorbets, fruit sauces, fruit fillings), plant preparations (e.g. ketchup, sauces, dried vegetables, frozen vegetables, cooked vegetables, boiled vegetables),They may be selected from the group consisting of snacks (such as baked or fried potato chips or potato dough products, corn or peanut extrudates), fat-based products or emulsions (such as high-fat or low-fat mayonnaise, remoulades, dressings, in each case), other ready-made dishes and soups used (such as dry soups, instant soups, ready-to-cook soups), spices, spice mixtures and seasonings used in particular, for example in the snacks sector, sweetener preparations, tablets or sachets, other preparations for sweetening or whitening beverages.

[0028] Preparations intended for nutritional or recreational purposes within the meaning of the present invention may be present as dietary supplements in the form of capsules, tablets (uncoated and coated tablets, e.g. with a gastro-resistant coating), dragees, granules, pellets, solid mixtures, dispersions in a liquid phase, as emulsions, as powders, as solutions, as pastes or other formulations that can be swallowed or chewed.

[0029] Preferably, the semi-finished preparations may be flavouring compositions, concentrates and / or intermediates intended to be used to prepare or to be part of (finished) preparations intended for nutritional or recreational purposes as defined above. The semi-finished preparations may also be used to prepare or to be part of another semi-finished preparation.

[0030] The preparation further preferably comprises: Plant extracts, such as sweet carbohydrates (sucrose, 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-glyceraldehyde, maltodextrin, etc.), sugar alcohols (erythritol, threitol, arabitol, ribitol, xylitol, sorbitol, maltodextrin, etc.), extracts or fractions obtained from natural sources containing amino acids and / or proteins, as well as physiologically acceptable salts of these amino acids and / or proteins, in particular their sodium, potassium, calcium or ammonium salts;Neohesperidin dihydrochalcone, Naringin dihydrochalcone, Steviol diurcoside, Stevioside, Steviolbioside, Rebaudioside, Rebaudioside A, Rebaudioside B, Rebaudioside C, Rebaudioside D, Rebaudioside E, Rebaudioside F, Rebaudioside G, Rebaudioside H, Rebaudioside M, Rebaudioside N, Rebaudioside Geoside X, dulcoside, rubusoside, suavioside A, suavioside B, suavioside G, suavioside H, suavioside I, suavioside J, bayunoside 1, bayunoside 2, phlomisoside 1, phlomisoside 2, phlomisoside 3, phlomisoside 4, abrusoside A, abrusoside B, abrusoside C, abrusoside D, cyclocarioside A, cyclocarioside oside I, oslandin, polypodoside A, strogin 1, strogin 2, strogin 4, seligueanin A, dihydroquercetin-3-acetate, perillartine, telosmoside A15, periandrins I to V, pterocaryosides, cyclocaryosides, mukuroziosides, trans-anethole, trans-cinnamaldehyde, bryosides, bryonosides, bryonodulcosides, carnosiflosides, scandenosides, gypenosides, hematoxylin, cyanin, chlorogenzoile, albizia saponin, telosmosides, gaudichaudioside, mogrosides such as mogroside V, hernandurcin, monatin, glycyrrhetinic acid and derivatives thereof, in particular glycyrrhizin, preferably glycyrrhizin ammonium salt;natural sweeteners, preferably naturally occurring sweet substances, including extracts or concentrated fractions of such extracts, such as extracts of Thaumatococcus spp. or Stevia spp., in particular Stevia rebaudiana, Swingle extracts, in particular Momordica charantia or Siratio grosvenorii or Monk fruit, extracts of Glyceridia spp., in particular Glyceridia glabra, extracts of Rubus spp., in particular Rubus suavissimus, extracts of Lippia dulcis, extracts of Mycetia balansae, preferably containing balancin A and / or balancin B; Preferably, synthetic sweeteners, preferably synthetic sweeteners, selected from the group consisting of magap, sodium cyclamate or other physiologically acceptable salts of cyclamic acid, acesulfam K; neohesperidin dihydrochalcone, naringin dihydrochalcone, saccharin, saccharin sodium salt, aspartame, superaspartame, neotam, alitam, advantam, perillartine, sucralose, lugudname, carrelame, sucrononate or sucrooctate or mixtures thereof; Preferably, the sweetener comprises at least one compound that provides a sweet taste, selected from the group consisting of:

[0031] Additionally or alternatively, the preparation preferably further comprises: Aliphatic flavoring substances, in particular saturated aliphatic alcohols such as ethanol, isopropanol, butanol, isoamyl alcohol, hexanol, 2-heptanol, octanol (1 / 2 / 3), decanol, unsaturated aliphatic alcohols such as cis-2 pentenol, cis-3 hexenol, trans-2 hexenol, trans-3 hexenol, cis-2 octenol, 1-octen-3-ol, cis-6 nonen-1-ol, trans-2,cis-6 nonadienol, aliphatic aldehydes such as saturated aliphatic aldehydes (e.g. acetaldehyde, propionaldehyde, butyraldehyde, isobutyraldehyde, valeraldehyde, isovaleraldehyde, hexanal, 3-methylhexanal, octanal, nonanal), or mono- or polyunsaturated aliphatic aldehydes such as 2-methylbutanol. trans-2-enal, trans-2 hexenal, cis-3 hexenal, cis-4 hexenal, trans-2 octenal, trans-2 nonenal, cis-6 nonenal, trans-2, cis-6 nonadienal, trans-2 decenal, trans-2, trans-decadienal, aliphatic ketones, such as saturated ketones (2-butanone, 2-pentanone, 2-heptanone, 2-octanone, etc.) non-, 2-methylheptan-3-one, 2-decanone, 2-undecanone, etc.), unsaturated ketones (1-penten-3-one, 1-hexen-3-one, 5-methyl-3-hexenone, 3-hepten-2-one, 1-octen-3-one, 2-octen-4-one, 3-octen-2-one, 3-nonen-2-one, etc.), aliphatic diketones and aliphatic diketol, such as diacetyl, acetylmethylcarbinol, 2,3-hexanedione, fatty acids, such as straight-chain saturated acids, e.g., acetic acid, propionic acid, butyric acid, isobutyric acid, valeric acid, heptanoic acid, octanoic acid, decanoic acid, branched-chain saturated acids, e.g., 2-methylheptanoic acid, 4-ethyloctanoic acid, as well as unsaturated acids, e.g., 2-butenoic acid, 2-pentenoic acid, 4-pentenoic acid, 2-methylpentenoic acid, trans-3 hexenoic acid, cis-3 hexenoic acid, 3-octenoic acid, linoleic acid, etc., aliphatic esters, such as saturated esters, e.g., methyl acetate, methyl butyrate , methyl 2-methylbutyrate, methyl hexanoate, ethyl acetate, ethyl butyrate, ethyl 2-methylbutyrate, ethyl 3-methylbutyrate, ethyl hexanoate, ethyl decanoate, isopropyl acetate, isobutyl acetate, isobutyl valerate, isoamyl acetate, isoamyl butyrate, isoamyl isovalerate, hexyl acetate, hexyl hexanoate, 3-octyl acetate and unsaturated esters such as methyl 2-hexenoate, allyl hexanoate, cis-3 hexenyl acetate, cis- 3-hexenyl, aliphatic thiols and dithiols (e.g., propanethiol, allyl mercaptan, 1-methoxy-3-methylbutane-3-thiol, dimethyl sulfide, dimethyl trisulfide, dipropyl sulfide, diallyl trisulfide), other aliphatic sulfur compounds, e.g., 2-mercapto-3-butanol, methylthiopropanal, 3-mercaptopentanone, 4-methoxy-2-methyl-2-mercaptobutanone, methyl thiobutyrate, methyl thiobutyrate, 3-methylthio Methyl propionate, aliphatic nitrogen compounds such as butylamine, trimethylamine, allyl isothiocyanate, isopropyl isothiocyanate, alicyclic compounds such as alicyclic ketones such as cis-jasmone, isophorone, 4-ketoisophorone, alicyclic esters such as methyl jasmonate, hydrion, terpenes such as terpene alcohols such as linalool, citronellol, geraniol, nerol, α-terpineol, menthol, 8-p-menthen-1,2-Diols, fenchol, borneol, nerolidol, hotrienol, terpene aldehydes such as geranial, neral, citronellal, β-sinensal, terpene ketones such as α-ionone, (D)-carvone, (L)-carvone, nootkatone, piperitone, menthone, α-damascone, β-damascene, damascenone, terpene esters such as linalyl acetate, geranyl acetate , citronellyl acetate, carbyl acetate, fenchyl acetate, terpene sulfur compounds, 4-mentha-8-thiol-3-one, thiogeraniol, para-menth-1-ene-8-thiol, mercapto-p-menthan-3-one, terpene hydrocarbons such as D-limonene, L-limonene, α-pinene, β-pinene, ocimene, α-terpinene, γ-terpinene, β-bisabolene, valencene, terpene oxides such as 1,8-cineole, rose oxide, mint lactone, menthofuran, aromatic compounds such as aromatic alcohols such as benzyl alcohol, cinnamyl alcohol, 2-phenyl alcohol, aromatic aldehydes such as benzaldehyde, cinnamaldehyde, 5-methyl-2-phenylhexenal, salicylaldehyde, 4-hydroxybenzaldehyde, cyclamen aldehyde, 2-phenyl-2-butenal, aromatic acids such as 2-phenylacetic acid, cinnamic acid, aromatic esters such as benzyl acetate, benzyl salicylate, anisyl acetate, methyl phenylacetate, methyl benzoate, methyl salicylate, methyl cinnamate, aromatic phenols such as phenol, ortho-cresol, para-cresol, 2,3-dimethylphenyl, 2-ethylphenol, 2,3,5-trimethylphenol, 4-vinylphenol, guaiacol, 4-vinylguaiacol, eugenol, thymol, carvacrol, aromatic sulfur compounds such as thiophenol, diphenyl disulfide, aromatic nitrogen compounds such as methyl anthranilate, methyl N-methylanthranilate, aromatic ethers such as vanillin, ethyl vanillin, anethole, aromatic oxides such as heliotropin, diphenyl oxide, aromatic lactones such as coumarin, dihydrocoumarin, heterocyclic compounds such as heterocyclic lactones such as γ-butyrolactone, γ-nonalactone, γ-decalactone, δ-decalactone, jasmine lactone, δ-dodecalactone, ambretride, heterocyclic furans such as furfuryl alcohol, furfural, 2-acetylfuran, theaspirane, 2-methyltetrahydrofuran-3 -one, furfuryl mercaptan, 2-methyl 3-furanthiol, 2-methyl 3-tetrahydrofuranthiol, difurfuryl sulfide, difurfuryl disulfide, heterocyclic pyrans such as maltol, ethyl maltol, rose oxide, maltol isobutyrate, heterocyclic pyrroles such as indole, 2-acetylpyrrole, pyrrolidine, heterocyclic pyrazines such as 2-methylpyrazine, 2,3-dimethylpyrazine, 2-methyl 3-ethylpyrazine, trimethylpyrazine, 2-acetylpyrazine, 2-methoxy 3-methylpyrazine, 2-methoxy 3-ethylpyrazine, 2-methoxy 3-isobutylpyrazine, 2-ethyl 3-methylthiopyrazine, heterocyclic thiazoles such as thiazole, 2-methylthiazole, 4-methyl 5-vinylthiazole, 2-isobutylthiazole, 2-acetylthiazole, Such as citrus (e.g. lemon, lime, mandarin orange, bergamot, grapefruit bitter orange, peel or essential oil), herbs (dill, parsley, cumin, rosemary, sage, clary sage, basil, tarragon, thyme, oregano, savory, marjoram, allspice, mace, nutmeg, clove leaves, clove buds, caraway, cinnamon leaves, cinnamon bark, cassia, cardamom, ginger, almond pulp, Turmeric, coriander seeds, coriander leaves, fenugreek, juniper berries, mugwort, bay leaves, eucalyptus, white pepper, green pepper, white pepper, carrot seeds, celery seeds, lovage leaves, asafoetida, onions, leeks, garlic, mustard, horseradish, chili peppers, paprika, seaweed, valerian oil, fir needles, spearmint, peppermint, wintergreen, beech leaves, Black currant bud, fennel, star anise, jambu, long pepper, davana, orris, mimosa, goldenrod, violet leaf, holy leaf, jasmine, ylang-ylang, cananga, osmanthus, angelica, clary sage, ambrette seed, hops, chamomile, lavender, rose, geranium, citronella, palmarosa, lily of the valley, lemongrass, tagetes, neroli, petitgrain, mate, cognac oil, coffee , cola nut, cocoa, green tea, black tea, white tea, gentian, tolu balsam, benzoin resin, Peru balsam, cascarilla, galbanum, vetiver, labdanum, patchouli, sandalwood, cedarwood, guaiacwood, oakwood, massoi bark, vanilla pods, tonka beans and concentrated fractions thereof, flavoring raw materials and flavoring preparations, e.g. essential oils, concretes, absolutes, extracts or tinctures from raw materials, Juice concentrates, for example orange juice, lemon juice, strawberry, cherry juice or passion fruit juice concentrates, aqueous phases and recoveries from raw materials such as citrus (lemon, lime, orange, mandarin orange, grapefruit), apple, pear, quince, medlar, red fruits (raspberry, strawberry, blueberry, blackberry, amelanchia (June plum), rose hips, cranberry, plum, prune, red currant and black currant, etc.), yellow fruits (peach, apricot, nectarine, banana, etc.), tropical fruits (mango, passion fruit, pineapple, lychee, etc.), vegetables (e.g. cucumber, tomato) and spices (e.g. ginger), Acetophenone, allyl caproate, α-ionone, β-ionone, anisaldehyde, anisyl acetate, anisyl formate, benzaldehyde, benzothiazole, benzyl acetate, benzyl alcohol, benzyl benzoate, β-ionone, butyl butyrate, butyl caproate, butylidenephthalide, carvone, camphene, caryophyllene, cineole, cinnamyl acetate, citral, citronellol, citronellal, citronellyl acetate, cyclohexyl acetate, cymene, damascone, decalactone, dihydrocoumarin, dimethicone anthranilate ethanol, dodecalactone, ethoxyethyl acetate, ethyl butyrate, ethyl butyrate, ethyl caprate, ethyl caproate, ethyl crotonate, ethyl furaneol, ethyl guaiacol, ethyl isobutyrate, ethyl isovalerate, ethyl lactate, ethyl methyl butyrate, ethyl propionate, eucalyptol, eugenol, ethyl heptylate, 4-(p-hydroxyphenyl)-2-butanone, γ-decalactone, geraniol, geranyl acetate, geranyl acetate, grapefruit aldehyde, methyl dihydrojasmonate (e.g., hydrion) (registered trademark), heliotropin, 2-heptanone, 3-heptanone, 4-heptanone, trans-2-heptenal, cis-4-heptenal, trans-2-hexenal, cis-3-hexenol, trans-2-heptenoic acid, trans-3-heptenoic acid, cis-2-hexenyl acetate, cis-3-hexenyl acetate, cis-3-hexenyl caproate, trans-2-hexenyl caproate, cis-3-hexenyl formate, cis-2-hexyl acetate, cis-3-hexyl acetate, trans-2-hexenyl acetate Sil, cis-3-hexyl formate, p-hydroxybenzyl acetone, isoamyl alcohol, isoamyl isovalerate, isobutyl butyrate, isobutyraldehyde, isoeugenol methyl ether, isopropyl methylthiazole, lauric acid, levulinic acid, linalool, linalool oxide, linalyl acetate, menthol, menthofuran, methyl anthranilate, methyl butanol, methyl butyric acid, 2-methylbutyl acetate, methyl caproate, methyl cinnamate, 5-methylfurfural, 3,2,2-methylcyclopentenolone, 6,5,2-Methylheptenone, methyl dihydrojasmonate, methyl jasmonate, 2-methylmethyl butyrate, 2-methyl-2-pentenoic acid, methyl thiobutyrate, 3,1-methylthiohexanol, 3-methylthiohexyl acetate, nerol, nerol acetate, trans, trans-2,4-nonadienal, 2,4-nonadienol, 2,6-nonadienol, 2,4-nonadienol, nootkatone, δ-octalactone, γ-octalactone, 2-octanol, 3-octanol, 1,3-octenol, acetic acid 1 -Octyl, 3-octyl acetate, palmitic acid, paraldehyde, phellandrene, pentanedione, phenylethyl acetate, phenylethyl alcohol, phenylethyl isovalerate, piperonal, propionaldehyde, propyl butyrate, pulegone, pulegol, sinensal, sulfurol, terpinene, terpineol, terpinolene, 8,3-s-thiomenthanone, 4,4,2-thiomethylpentanone, thymol, δ-undecalactone, γ-undecalactone, valencene, valeric acid, vanillin, acetoin, ethyl Vanillin, ethyl vanillin isobutyrate (=3-ethoxy-4-isobutyryloxybenzaldehyde), 2,5-dimethyl-4-hydroxy-3(2H)-furanone and derivatives thereof (preferably homofuraneol (=2-ethyl-4-hydroxy-5-methyl-3(2H)-furanone), homofuranol (=2-ethyl-5-methyl-4-hydroxy-3(2H)-furanone and 5-ethyl-2-methyl-4-hydroxy-3(2H)-furanone), maltol and maltol derivatives (preferably homofuraneol (=2-ethyl-4-hydroxy-5-methyl-3(2H)-furanone) and 5-ethyl-2-methyl-4-hydroxy-3(2H)-furanone), maltol and derivatives thereof (preferably homofuraneol (=2-ethyl-5-methyl-4-hydroxy ... in this specification, preferably ethyl maltol), coumarin and coumarin derivatives, γ-lactones (herein preferably γ-undecalactone, γ-nonalactone, γ-decalactone), δ-lactones (herein preferably 4-methyl δ-decalactone, massolactone, δ-decalactone, tuberolactone), methyl sorbate, divanillin, 4-hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2H)furanone, 2-hydroxy-3-methyl-2-cyclopentenone, 3-hydroxy-4,5-Dimethyl-2(5H)-furanone, acetic acid isoamyl ester, butyric acid ethyl ester, butyric acid-n-butyl ester, butyric acid isoamyl ester, 3-methyl-butyric acid ethyl ester, n-hexanoic acid ethyl ester, n-hexanoic acid allyl ester, n-hexanoic acid-n-butyl ester, n-octanoic acid ethyl ester, ethyl-3-methyl-3-phenylglycidate, ethyl-2-trans-4-cis-decadienoate, 4-(p-hydroxyphenyl)-2-butanone, 1,1-dimethoxy-2, 2,5-trimethyl-4-hexane, 2,6-dimethyl-5-hepten-1-al and phenylacetaldehyde, 2-methyl-3-(methylthio)furan, 2-methyl-3-furanthiol, bis(2-methyl-3-furyl)disulfide, furfuryl mercaptan, methional, 2-acetyl-2-thiazoline, 3-mercapto-2-pentanone, 2,5-dimethyl-3-furanthiol, 2,4,5-trimethylthiazole, 2-acetylthiazole, 2,4-dimethyl-5-ethylthiazole, 2-Acetyl-1-pyrroline, 2-methyl-3-ethylpyrazine, 2-ethyl-3,5-dimethylpyrazine, 2-ethyl-3,6-dimethylpyrazine, 2,3-diethyl-5-methylpyrazine, 3-isopropyl-2-methoxypyrazine, 3-isobutyl-2-methoxypyrazine, 2-acetylpyrazine, 2-pentylpyridine, (E,E)-2,4-decadienal, (E,E)-2,4-nonadienal, (E)-2-octenal, (E)-2-nonenal, 2-undecenal, 12-methyltrideca nal, 1-penten-3-one, 4-hydroxy-2,5-dimethyl-3(2H)-furanone, guaiacol, 3-hydroxy-4,5-dimethyl-2(5H)-furanone, 3-hydroxy-4-methyl-5-ethyl-2(5H)-furanone, cinnamaldehyde, cinnamon alcohol, methyl salicylate, isopulegol and any stereoisomers, enantiomers, positional isomers, diastereomers, cis / trans isomers or epimers of these substances (not explicitly mentioned herein), Preferably, the flavoring agent comprises a flavoring agent selected from the group consisting of:

[0032] Another aspect of the present invention is a composition comprising naringenin in an amount of 10 ppm to 100 ppm, preferably 16 ppm to 80 ppm, and most preferably 20 ppm to 50 ppm, and phloretin in an amount of 10 ppm to 100 ppm, preferably 15 ppm to 80 ppm, and most preferably 20 ppm to 50 ppm, As a prerequisite, If the preparation contains 30 ppm phloretin, naringenin is not contained in the amount of 30 ppm; If the preparation contains 15 ppm phloretin, naringenin is not contained in an amount of 15 ppm. It relates to aroma compositions.

[0033] Surprisingly, it has been found that aroma compositions having the above-described concentrations of naringenin and phloretin exhibit a much more balanced taste profile, particularly in terms of reduced bitterness, improved mouthfeel, reduced astringency and / or increased sweetness, compared to compositions not having the concentrations of naringenin and phloretin according to the present invention.

[0034] Preferably, the aroma composition contains naringenin and phloretin in a weight ratio of 1:5 to 5:1, preferably 1:3 to 3:1, more preferably 1:1.5 to 1.5:1.

[0035] Aroma compositions having these ratios of naringenin to phloretin exhibit a much more balanced taste profile, particularly in terms of reduced bitterness, increased mouthfeel, reduced astringency and / or increased sweetness, compared to compositions lacking naringenin and / or phloretin or having a ratio of naringenin to phloretin outside the ratios according to the present invention.

[0036] In the context of the present invention, the aroma composition further preferably comprises: Plant extracts, such as sweet carbohydrates (sucrose, 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-glyceraldehyde, maltodextrin, etc.), sugar alcohols (erythritol, threitol, arabitol, ribitol, xylitol, sorbitol, maltodextrin, etc.), extracts or fractions obtained from natural sources containing amino acids and / or proteins, as well as physiologically acceptable salts of these amino acids and / or proteins, in particular their sodium, potassium, calcium or ammonium salts;Neohesperidin dihydrochalcone, Naringin dihydrochalcone, Steviol diurcoside, Stevioside, Steviolbioside, Rebaudioside, Rebaudioside A, Rebaudioside B, Rebaudioside C, Rebaudioside D, Rebaudioside E, Rebaudioside F, Rebaudioside G, Rebaudioside H, Rebaudioside M, Rebaudioside N, Rebaudioside Geoside X, dulcoside, rubusoside, suavioside A, suavioside B, suavioside G, suavioside H, suavioside I, suavioside J, bayunoside 1, bayunoside 2, phlomisoside 1, phlomisoside 2, phlomisoside 3, phlomisoside 4, abrusoside A, abrusoside B, abrusoside C, abrusoside D, cyclocarioside A, cyclocarioside oside I, oslandin, polypodoside A, strogin 1, strogin 2, strogin 4, seligueanin A, dihydroquercetin-3-acetate, perillartine, telosmoside A15, periandrins I to V, pterocaryosides, cyclocaryosides, mukuroziosides, trans-anethole, trans-cinnamaldehyde, bryosides, bryonosides, bryonodulcosides, carnosiflosides, scandenosides, gypenosides, hematoxylin, cyanin, chlorogenzoile, albizia saponin, telosmosides, gaudichaudioside, mogrosides such as mogroside V, hernandurcin, monatin, glycyrrhetinic acid and derivatives thereof, in particular glycyrrhizin, preferably glycyrrhizin ammonium salt;natural sweeteners, preferably naturally occurring sweet substances, including extracts or concentrated fractions of such extracts, such as extracts of Thaumatococcus spp. or Stevia spp., in particular Stevia rebaudiana, Swingle extracts, in particular Momordica charantia or Siratio grosvenorii or Monk fruit, extracts of Glyceridia spp., in particular Glyceridia glabra, extracts of Rubus spp., in particular Rubus suavissimus, extracts of Lippia dulcis, extracts of Mycetia balansae, preferably containing balancin A and / or balancin B; Preferably, synthetic sweeteners, preferably synthetic sweeteners, selected from the group consisting of magap, sodium cyclamate or other physiologically acceptable salts of cyclamic acid, acesulfam K; neohesperidin dihydrochalcone, naringin dihydrochalcone, saccharin, saccharin sodium salt, aspartame, superaspartame, neotam, alitam, advantam, perillartine, sucralose, lugudname, carrelame, sucrononate or sucrooctate or mixtures thereof; It is also preferred that the composition contains at least one compound that provides a sweet taste, selected from the group consisting of:

[0037] Preferably, the aroma composition also preferably comprises: Aliphatic flavoring substances, in particular saturated aliphatic alcohols such as ethanol, isopropanol, butanol, isoamyl alcohol, hexanol, 2-heptanol, octanol (1 / 2 / 3), decanol, unsaturated aliphatic alcohols such as cis-2 pentenol, cis-3 hexenol, trans-2 hexenol, trans-3 hexenol, cis-2 octenol, 1-octen-3-ol, cis-6 nonen-1-ol, trans-2,cis-6 nonadienol, aliphatic aldehydes such as saturated aliphatic aldehydes (e.g. acetaldehyde, propionaldehyde, butyraldehyde, isobutyraldehyde, valeraldehyde, isovaleraldehyde, hexanal, 3-methylhexanal, octanal, nonanal), or mono- or polyunsaturated aliphatic aldehydes such as 2-methylbutanol. trans-2-enal, trans-2 hexenal, cis-3 hexenal, cis-4 hexenal, trans-2 octenal, trans-2 nonenal, cis-6 nonenal, trans-2, cis-6 nonadienal, trans-2 decenal, trans-2, trans-decadienal, aliphatic ketones, such as saturated ketones (2-butanone, 2-pentanone, 2-heptanone, 2-octanone, etc.) non-, 2-methylheptan-3-one, 2-decanone, 2-undecanone, etc.), unsaturated ketones (1-penten-3-one, 1-hexen-3-one, 5-methyl-3-hexenone, 3-hepten-2-one, 1-octen-3-one, 2-octen-4-one, 3-octen-2-one, 3-nonen-2-one, etc.), aliphatic diketones and aliphatic diketol, such as diacetyl, acetylmethylcarbinol, 2,3-hexanedione, fatty acids, such as straight-chain saturated acids, e.g., acetic acid, propionic acid, butyric acid, isobutyric acid, valeric acid, heptanoic acid, octanoic acid, decanoic acid, branched-chain saturated acids, e.g., 2-methylheptanoic acid, 4-ethyloctanoic acid, as well as unsaturated acids, e.g., 2-butenoic acid, 2-pentenoic acid, 4-pentenoic acid, 2-methylpentenoic acid, trans-3 hexenoic acid, cis-3 hexenoic acid, 3-octenoic acid, linoleic acid, etc., aliphatic esters, such as saturated esters, e.g., methyl acetate, methyl butyrate , methyl 2-methylbutyrate, methyl hexanoate, ethyl acetate, ethyl butyrate, ethyl 2-methylbutyrate, ethyl 3-methylbutyrate, ethyl hexanoate, ethyl decanoate, isopropyl acetate, isobutyl acetate, isobutyl valerate, isoamyl acetate, isoamyl butyrate, isoamyl isovalerate, hexyl acetate, hexyl hexanoate, 3-octyl acetate and unsaturated esters such as methyl 2-hexenoate, allyl hexanoate, cis-3 hexenyl acetate, cis- 3-hexenyl, aliphatic thiols and dithiols (e.g., propanethiol, allyl mercaptan, 1-methoxy-3-methylbutane-3-thiol, dimethyl sulfide, dimethyl trisulfide, dipropyl sulfide, diallyl trisulfide), other aliphatic sulfur compounds, e.g., 2-mercapto-3-butanol, methylthiopropanal, 3-mercaptopentanone, 4-methoxy-2-methyl-2-mercaptobutanone, methyl thiobutyrate, methyl thiobutyrate, 3-methylthio Methyl propionate, aliphatic nitrogen compounds such as butylamine, trimethylamine, allyl isothiocyanate, isopropyl isothiocyanate, alicyclic compounds such as alicyclic ketones such as cis-jasmone, isophorone, 4-ketoisophorone, alicyclic esters such as methyl jasmonate, hydrion, terpenes such as terpene alcohols such as linalool, citronellol, geraniol, nerol, α-terpineol, menthol, 8-p-menthen-1,2-Diols, fenchol, borneol, nerolidol, hotrienol, terpene aldehydes such as geranial, neral, citronellal, β-sinensal, terpene ketones such as α-ionone, (D)-carvone, (L)-carvone, nootkatone, piperitone, menthone, α-damascone, β-damascene, damascenone, terpene esters such as linalyl acetate, geranyl acetate , citronellyl acetate, carbyl acetate, fenchyl acetate, terpene sulfur compounds, 4-mentha-8-thiol-3-one, thiogeraniol, para-menth-1-ene-8-thiol, mercapto-p-menthan-3-one, terpene hydrocarbons such as D-limonene, L-limonene, α-pinene, β-pinene, ocimene, α-terpinene, γ-terpinene, β-bisabolene, valencene, terpene oxides such as 1,8-cineole, rose oxide, mint lactone, menthofuran, aromatic compounds such as aromatic alcohols such as benzyl alcohol, cinnamyl alcohol, 2-phenyl alcohol, aromatic aldehydes such as benzaldehyde, cinnamaldehyde, 5-methyl-2-phenylhexenal, salicylaldehyde, 4-hydroxybenzaldehyde, cyclamen aldehyde, 2-phenyl-2-butenal, aromatic acids such as 2-phenylacetic acid, cinnamic acid, aromatic esters such as benzyl acetate, benzyl salicylate, anisyl acetate, methyl phenylacetate, methyl benzoate, methyl salicylate, methyl cinnamate, aromatic phenols such as phenol, ortho-cresol, para-cresol, 2,3-dimethylphenyl, 2-ethylphenol, 2,3,5-trimethylphenol, 4-vinylphenol, guaiacol, 4-vinylguaiacol, eugenol, thymol, carvacrol, aromatic sulfur compounds such as thiophenol, diphenyl disulfide, aromatic nitrogen compounds such as methyl anthranilate, methyl N-methylanthranilate, aromatic ethers such as vanillin, ethyl vanillin, anethole, aromatic oxides such as heliotropin, diphenyl oxide, aromatic lactones such as coumarin, dihydrocoumarin, heterocyclic compounds such as heterocyclic lactones such as γ-butyrolactone, γ-nonalactone, γ-decalactone, δ-decalactone, jasmine lactone, δ-dodecalactone, ambretride, heterocyclic furans such as furfuryl alcohol, furfural, 2-acetylfuran, theaspirane, 2-methyltetrahydrofuran-3 -one, furfuryl mercaptan, 2-methyl 3-furanthiol, 2-methyl 3-tetrahydrofuranthiol, difurfuryl sulfide, difurfuryl disulfide, heterocyclic pyrans such as maltol, ethyl maltol, rose oxide, maltol isobutyrate, heterocyclic pyrroles such as indole, 2-acetylpyrrole, pyrrolidine, heterocyclic pyrazines such as 2-methylpyrazine, 2,3-dimethylpyrazine, 2-methyl 3-ethylpyrazine, trimethylpyrazine, 2-acetylpyrazine, 2-methoxy 3-methylpyrazine, 2-methoxy 3-ethylpyrazine, 2-methoxy 3-isobutylpyrazine, 2-ethyl 3-methylthiopyrazine, heterocyclic thiazoles such as thiazole, 2-methylthiazole, 4-methyl 5-vinylthiazole, 2-isobutylthiazole, 2-acetylthiazole, Such as citrus (e.g. lemon, lime, mandarin orange, bergamot, grapefruit bitter orange, peel or essential oil), herbs (dill, parsley, cumin, rosemary, sage, clary sage, basil, tarragon, thyme, oregano, savory, marjoram, allspice, mace, nutmeg, clove leaves, clove buds, caraway, cinnamon leaves, cinnamon bark, cassia, cardamom, ginger, almond pulp, Turmeric, coriander seeds, coriander leaves, fenugreek, juniper berries, mugwort, bay leaves, eucalyptus, white pepper, green pepper, white pepper, carrot seeds, celery seeds, lovage leaves, asafoetida, onions, leeks, garlic, mustard, horseradish, chili peppers, paprika, seaweed, valerian oil, fir needles, spearmint, peppermint, wintergreen, beech leaves, Black currant bud, fennel, star anise, jambu, long pepper, davana, orris, mimosa, goldenrod, violet leaf, holy leaf, jasmine, ylang-ylang, cananga, osmanthus, angelica, clary sage, ambrette seed, hops, chamomile, lavender, rose, geranium, citronella, palmarosa, lily of the valley, lemongrass, tagetes, neroli, petitgrain, mate, cognac oil, coffee , cola nut, cocoa, green tea, black tea, white tea, gentian, tolu balsam, benzoin resin, Peru balsam, cascarilla, galbanum, vetiver, labdanum, patchouli, sandalwood, cedarwood, guaiacwood, oakwood, massoi bark, vanilla pods, tonka beans and concentrated fractions thereof, flavoring raw materials and flavoring preparations, e.g. essential oils, concretes, absolutes, extracts or tinctures from raw materials, Juice concentrates, for example orange juice, lemon juice, strawberry, cherry juice or passion fruit juice concentrates, aqueous phases and recoveries from raw materials such as citrus (lemon, lime, orange, mandarin orange, grapefruit), apple, pear, quince, medlar, red fruits (raspberry, strawberry, blueberry, blackberry, amelanchia (June plum), rose hips, cranberry, plum, prune, red currant and black currant, etc.), yellow fruits (peach, apricot, nectarine, banana, etc.), tropical fruits (mango, passion fruit, pineapple, lychee, etc.), vegetables (e.g. cucumber, tomato) and spices (e.g. ginger), Acetophenone, allyl caproate, α-ionone, β-ionone, anisaldehyde, anisyl acetate, anisyl formate, benzaldehyde, benzothiazole, benzyl acetate, benzyl alcohol, benzyl benzoate, β-ionone, butyl butyrate, butyl caproate, butylidenephthalide, carvone, camphene, caryophyllene, cineole, cinnamyl acetate, citral, citronellol, citronellal, citronellyl acetate, cyclohexyl acetate, cymene, damascone, decalactone, dihydrocoumarin, dimethicone anthranilate ethanol, dodecalactone, ethoxyethyl acetate, ethyl butyrate, ethyl butyrate, ethyl caprate, ethyl caproate, ethyl crotonate, ethyl furaneol, ethyl guaiacol, ethyl isobutyrate, ethyl isovalerate, ethyl lactate, ethyl methyl butyrate, ethyl propionate, eucalyptol, eugenol, ethyl heptylate, 4-(p-hydroxyphenyl)-2-butanone, γ-decalactone, geraniol, geranyl acetate, geranyl acetate, grapefruit aldehyde, methyl dihydrojasmonate (e.g., hydrion) (registered trademark), heliotropin, 2-heptanone, 3-heptanone, 4-heptanone, trans-2-heptenal, cis-4-heptenal, trans-2-hexenal, cis-3-hexenol, trans-2-heptenoic acid, trans-3-heptenoic acid, cis-2-hexenyl acetate, cis-3-hexenyl acetate, cis-3-hexenyl caproate, trans-2-hexenyl caproate, cis-3-hexenyl formate, cis-2-hexyl acetate, cis-3-hexyl acetate, trans-2-hexenyl acetate Sil, cis-3-hexyl formate, p-hydroxybenzyl acetone, isoamyl alcohol, isoamyl isovalerate, isobutyl butyrate, isobutyraldehyde, isoeugenol methyl ether, isopropyl methylthiazole, lauric acid, levulinic acid, linalool, linalool oxide, linalyl acetate, menthol, menthofuran, methyl anthranilate, methyl butanol, methyl butyric acid, 2-methylbutyl acetate, methyl caproate, methyl cinnamate, 5-methylfurfural, 3,2,2-methylcyclopentenolone, 6,5,2-Methylheptenone, methyl dihydrojasmonate, methyl jasmonate, 2-methylmethyl butyrate, 2-methyl-2-pentenoic acid, methyl thiobutyrate, 3,1-methylthiohexanol, 3-methylthiohexyl acetate, nerol, nerol acetate, trans, trans-2,4-nonadienal, 2,4-nonadienol, 2,6-nonadienol, 2,4-nonadienol, nootkatone, δ-octalactone, γ-octalactone, 2-octanol, 3-octanol, 1,3-octenol, acetic acid 1 -Octyl, 3-octyl acetate, palmitic acid, paraldehyde, phellandrene, pentanedione, phenylethyl acetate, phenylethyl alcohol, phenylethyl isovalerate, piperonal, propionaldehyde, propyl butyrate, pulegone, pulegol, sinensal, sulfurol, terpinene, terpineol, terpinolene, 8,3-s-thiomenthanone, 4,4,2-thiomethylpentanone, thymol, δ-undecalactone, γ-undecalactone, valencene, valeric acid, vanillin, acetoin, ethyl Vanillin, ethyl vanillin isobutyrate (=3-ethoxy-4-isobutyryloxybenzaldehyde), 2,5-dimethyl-4-hydroxy-3(2H)-furanone and derivatives thereof (preferably homofuraneol (=2-ethyl-4-hydroxy-5-methyl-3(2H)-furanone), homofuranol (=2-ethyl-5-methyl-4-hydroxy-3(2H)-furanone and 5-ethyl-2-methyl-4-hydroxy-3(2H)-furanone), maltol and maltol derivatives (preferably homofuraneol (=2-ethyl-4-hydroxy-5-methyl-3(2H)-furanone) and 5-ethyl-2-methyl-4-hydroxy-3(2H)-furanone), maltol and derivatives thereof (preferably homofuraneol (=2-ethyl-5-methyl-4-hydroxy ... in this specification, preferably ethyl maltol), coumarin and coumarin derivatives, γ-lactones (herein preferably γ-undecalactone, γ-nonalactone, γ-decalactone), δ-lactones (herein preferably 4-methyl δ-decalactone, massolactone, δ-decalactone, tuberolactone), methyl sorbate, divanillin, 4-hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2H)furanone, 2-hydroxy-3-methyl-2-cyclopentenone, 3-hydroxy-4,5-Dimethyl-2(5H)-furanone, acetic acid isoamyl ester, butyric acid ethyl ester, butyric acid-n-butyl ester, butyric acid isoamyl ester, 3-methyl-butyric acid ethyl ester, n-hexanoic acid ethyl ester, n-hexanoic acid allyl ester, n-hexanoic acid-n-butyl ester, n-octanoic acid ethyl ester, ethyl-3-methyl-3-phenylglycidate, ethyl-2-trans-4-cis-decadienoate, 4-(p-hydroxyphenyl)-2-butanone, 1,1-dimethoxy-2, 2,5-trimethyl-4-hexane, 2,6-dimethyl-5-hepten-1-al and phenylacetaldehyde, 2-methyl-3-(methylthio)furan, 2-methyl-3-furanthiol, bis(2-methyl-3-furyl)disulfide, furfuryl mercaptan, methional, 2-acetyl-2-thiazoline, 3-mercapto-2-pentanone, 2,5-dimethyl-3-furanthiol, 2,4,5-trimethylthiazole, 2-acetylthiazole, 2,4-dimethyl-5-ethylthiazole, 2-Acetyl-1-pyrroline, 2-methyl-3-ethylpyrazine, 2-ethyl-3,5-dimethylpyrazine, 2-ethyl-3,6-dimethylpyrazine, 2,3-diethyl-5-methylpyrazine, 3-isopropyl-2-methoxypyrazine, 3-isobutyl-2-methoxypyrazine, 2-acetylpyrazine, 2-pentylpyridine, (E,E)-2,4-decadienal, (E,E)-2,4-nonadienal, (E)-2-octenal, (E)-2-nonenal, 2-undecenal, 12-methyltrideca nal, 1-penten-3-one, 4-hydroxy-2,5-dimethyl-3(2H)-furanone, guaiacol, 3-hydroxy-4,5-dimethyl-2(5H)-furanone, 3-hydroxy-4-methyl-5-ethyl-2(5H)-furanone, cinnamaldehyde, cinnamon alcohol, methyl salicylate, isopulegol and any stereoisomers, enantiomers, positional isomers, diastereomers, cis / trans isomers or epimers of these substances (not explicitly mentioned herein), The flavoring material is selected from the group consisting of:

[0038] Another aspect of the present invention is a method for reducing bitterness and / or improving mouthfeel and / or reducing astringency and / or improving sweetness intensity of a preparation comprising phloretin, comprising: i. preparing a preparation comprising phloretin; ii. adding naringenin in an amount such that the weight ratio of phloretin to naringenin is 1:5 to 5:1, preferably 1:3 to 3:1, and more preferably 1:1.5 to 1.5:1; iii. Obtaining a preparation that has reduced bitterness and / or improved mouthfeel and / or reduced astringency and / or improved sweetness intensity compared to such a preparation not containing naringenin; Including, As a prerequisite, if the preparation contains 30 ppm phloretin, naringenin is not added in the amount of 30 ppm, and if the preparation contains 15 ppm phloretin, naringenin is not added in the amount of 15 ppm. Regarding the method.

[0039] Preferably, the naringenin added in step ii. is added in an amount of 10 ppm to 100 ppm, preferably 16 ppm to 80 ppm, most preferably 20 ppm to 50 ppm based on the total amount of the preparation.

[0040] The preparations are preferably selected from the group consisting of aroma compositions, preparations intended for nutritional, recreational or cosmetic or pharmaceutical purposes, and semi-finished products for producing such preparations.

[0041] Furthermore, what has been said above (mentioned with respect to other aspects according to the invention as well as in particular with respect to the respective preferred embodiments) applies equally to the method according to the invention.

[0042] Another aspect of the invention relates to a semi-finished product for producing a preparation intended for nutritional, recreational or cosmetic or pharmaceutical purposes, preferably a preparation as described above, which semi-finished product comprises: The aroma composition according to the present invention, or Naringenin in an amount of 10 ppm to 100 ppm, preferably 16 ppm to 80 ppm, and most preferably 20 ppm to 50 ppm, and phloretin in an amount of 10 ppm to 100 ppm, preferably 15 ppm to 80 ppm, and most preferably 20 ppm to 50 ppm, As a prerequisite, If the preparation contains 30 ppm phloretin, then naringenin will not be contained in an amount of 30 ppm, and if the preparation contains 15 ppm phloretin, then naringenin will not be contained in an amount of 15 ppm.

[0043] One aspect of the present invention relates to a product intended for nutritional, recreational, cosmetic or pharmaceutical purposes, comprising an aroma composition according to the present invention or a semi-finished product according to the present invention, or naringenin in an amount of 10 ppm to 100 ppm, preferably 16 ppm to 80 ppm, and most preferably 20 ppm to 50 ppm, and phloretin in an amount of 10 ppm to 100 ppm, preferably 15 ppm to 80 ppm, and most preferably 20 ppm to 50 ppm, provided that if the preparation contains 30 ppm phloretin, naringenin is not contained in an amount of 30 ppm, and if the preparation contains 15 ppm phloretin, naringenin is not contained in an amount of 15 ppm.

[0044] Here too, what has been said above (mentioned in connection with other aspects according to the invention and in particular with the respective preferred embodiments) applies equally to the (semi-finished) product according to the invention. [Brief explanation of the drawings]

[0045] [Figure 1] The bitterness perception of compositions containing different amounts of naringenin is described, with a bitterness perception of 4 meaning the most bitter and 1 being the least bitter. [Figure 2] The bitterness perception of compositions with various ratios of phloretin to naringenin at a phloretin concentration of 15 ppm is described. A bitterness perception of 4 means the most bitter and 1 is the least bitter. [Figure 3]The bitterness perception of compositions with various ratios of phloretin to naringenin at a phloretin concentration of 30 ppm is described. A bitterness perception of 4 means the most bitter and 1 is the least bitter. [Figure 4] The bitterness perception of compositions with various ratios of phloretin to naringenin at a phloretin concentration of 80 ppm is described. A bitterness perception of 4 means the most bitter and 1 is the least bitter. [Example]

[0046] A panel of experienced flavorists were given samples of various concentrations of phloretin and naringenin in water and asked to rank the samples based on bitterness, with the most bitter sample receiving the highest rank and the least bitter sample receiving the lowest rank.

[0047] [Table 1] The data shown in the table above are also shown in Figures 1-4.

[0048] Formulation Example (FE)

[0049] [Table 2]

[0050] [Table 3] Preparation: Mix the ingredients in the specified order and add water until the weight percentage reaches 100%. Then fill the mixture into a glass bottle and blow in carbon dioxide.

[0051] [Table 4]

Claims

1. 1. Use of naringenin for reducing bitterness and / or improving mouthfeel and / or reducing astringency and / or improving sweetness intensity of or in a preparation comprising phloretin, Naringenin is used in an amount of 10 ppm to 100 ppm, preferably 15 ppm to 80 ppm, most preferably 20 ppm to 50 ppm, based on the total amount of the preparation; As a prerequisite, When naringenin is used to reduce the bitterness of or in a preparation containing 30 ppm of phloretin, naringenin is not contained in an amount of 30 ppm, in each case based on the total amount of the preparation; When naringenin is used to improve the mouthfeel of a preparation containing 30 ppm of phloretin, the naringenin is not contained in an amount of 30 ppm, in each case based on the total amount of the preparation. Use of Naringenin.

2. 2. The use according to claim 1, provided that if the preparation contains 30 ppm of phloretin, then naringenin is not contained in an amount of 30 ppm.

3. The use according to claim 1 or claim 2, wherein the weight ratio of naringenin to phloretin in the preparation is in the range of 1:5 to 5:1, preferably 1:3 to 3:1, more preferably 1:1.5 to 1.5:

1.

4. 4. Use according to any one of claims 1 to 3, wherein the preparation is selected from the group consisting of aromatic compositions, preparations intended for nutritional, recreational or cosmetic or medicinal purposes, and semi-finished products for producing such preparations.

5. The preparation further preferably comprises: Plant extracts, for example, sweet carbohydrates (sucrose, 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-glyceraldehyde, maltodextrin, etc.), sugar alcohols (erythritol, threitol, arabitol, ribitol, xylitol, sorbitol, maltodextrin, etc.), extracts or fractions obtained from natural sources containing amino acids and / or proteins, as well as physiologically acceptable salts of these amino acids and / or proteins, in particular their sodium, potassium, calcium or ammonium salts;Neohesperidin dihydrochalcone, Naringin dihydrochalcone, Steviol diurcoside, Stevioside, Steviolbioside, Rebaudioside, Rebaudioside A, Rebaudioside B, Rebaudioside C, Rebaudioside D, Rebaudioside E, Rebaudioside F, Rebaudioside G, Rebaudioside H, Rebaudioside M, Rebaudioside N, Rebaudioside Geoside X, dulcoside, rubusoside, suavioside A, suavioside B, suavioside G, suavioside H, suavioside I, suavioside J, bayunoside 1, bayunoside 2, phlomisoside 1, phlomisoside 2, phlomisoside 3, phlomisoside 4, abrusoside A, abrusoside B, abrusoside C, abrusoside D, cyclocaryoside A, cyclocaryoside oside I, oslandin, polypodoside A, strogin 1, strogin 2, strogin 4, seligueanin A, dihydroquercetin-3-acetate, perillartine, telosmoside A15, periandrins I to V, pterocaryosides, cyclocaryosides, mukuroziosides, trans-anethole, trans-cinnamaldehyde, bryoside, bryonoside, bryonodulcosides, carnosifloside, scandenoside, gypenosides, hematoxylin, cyanin, chlorogenzoile, albiziasaponin, telosmosides, gaudichaudioside, mogrosides such as mogroside V, hernandurcin, monatin, glycyrrhetinic acid and derivatives thereof, in particular glycyrrhizin, preferably glycyrrhizin ammonium salt;Extracts of Thaumatococcus spp. or Stevia spp., in particular Stevia rebaudiana, Swingle extracts, in particular Momordica charantia or Siratio grosvenorii or Monk fruit, Glyceridia spp., in particular Glyceridia glabra, Rubus spp., in particular Rubus suavissimus, extracts of Lippia dulcis, Mycetia balansae, preferably containing balancin A and / or balancin B, natural sweeteners, preferably naturally occurring sweeteners, including extracts such as extracts of Saccharomyces cerevisiae (Saccharomyces cerevisiae) or concentrated fractions of such extracts; Preferably, synthetic sweeteners, preferably synthetic sweeteners, selected from the group consisting of magap, sodium cyclamate or other physiologically acceptable salts of cyclamic acid, acesulfame potassium (acesulfam K); neohesperidin dihydrochalcone, naringin dihydrochalcone, saccharin, saccharin sodium salt, aspartame, superaspartame, neotam, alitam, advantam, perillartine, sucralose, luguduname, carrelame, sucrononate or sucrooctate or mixtures thereof; The use according to any one of claims 1 to 4, comprising at least one compound that provides sweetness selected from the group consisting of:

6. The use according to any one of claims 1 to 5, wherein the preparation further comprises a flavoring material.

7. Naringenin in an amount of 10 ppm to 100 ppm, preferably 16 ppm to 80 ppm, and most preferably 20 ppm to 50 ppm, and phloretin in an amount of 10 ppm to 100 ppm, preferably 15 ppm to 80 ppm, and most preferably 20 ppm to 50 ppm; As a prerequisite, If the preparation contains 30 ppm phloretin, naringenin is not contained in an amount of 30 ppm; If the preparation contains 15 ppm phloretin, naringenin is not contained in an amount of 15 ppm. Aromatic composition.

8. 8. The aroma composition according to claim 7, wherein the aroma composition comprises naringenin and phloretin in a weight ratio of 1:5 to 5:1, preferably 1:3 to 3:1, and more preferably 1:1.5 to 1.5:

1.

9. The aroma composition further preferably comprises: Plant extracts, for example, sweet carbohydrates (sucrose, 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-glyceraldehyde, maltodextrin, etc.), sugar alcohols (erythritol, threitol, arabitol, ribitol, xylitol, sorbitol, maltodextrin, etc.), extracts or fractions obtained from natural sources containing amino acids and / or proteins, as well as physiologically acceptable salts of these amino acids and / or proteins, in particular their sodium, potassium, calcium or ammonium salts;Neohesperidin dihydrochalcone, Naringin dihydrochalcone, Steviol diurcoside, Stevioside, Steviolbioside, Rebaudioside, Rebaudioside A, Rebaudioside B, Rebaudioside C, Rebaudioside D, Rebaudioside E, Rebaudioside F, Rebaudioside G, Rebaudioside H, Rebaudioside M, Rebaudioside N, Rebaudioside Geoside X, dulcoside, rubusoside, suavioside A, suavioside B, suavioside G, suavioside H, suavioside I, suavioside J, bayunoside 1, bayunoside 2, phlomisoside 1, phlomisoside 2, phlomisoside 3, phlomisoside 4, abrusoside A, abrusoside B, abrusoside C, abrusoside D, cyclocaryoside A, cyclocaryoside oside I, oslandin, polypodoside A, strogin 1, strogin 2, strogin 4, seligueanin A, dihydroquercetin-3-acetate, perillartine, telosmoside A15, periandrins I to V, pterocaryosides, cyclocaryosides, mukuroziosides, trans-anethole, trans-cinnamaldehyde, bryoside, bryonoside, bryonodulcosides, carnosifloside, scandenoside, gypenosides, hematoxylin, cyanin, chlorogenzoile, albiziasaponin, telosmosides, gaudichaudioside, mogrosides such as mogroside V, hernandurcin, monatin, glycyrrhetinic acid and derivatives thereof, in particular glycyrrhizin, preferably glycyrrhizin ammonium salt;Extracts of Thaumatococcus spp. or Stevia spp., in particular Stevia rebaudiana, Swingle extracts, in particular Momordica charantia or Siratio grosvenorii or Monk fruit, Glyceridia spp., in particular Glyceridia glabra, Rubus spp., in particular Rubus suavissimus, extracts of Lippia dulcis, Mycetia balansae, preferably containing balancin A and / or balancin B, natural sweeteners, preferably naturally occurring sweeteners, including extracts such as extracts of Saccharomyces cerevisiae (Saccharomyces cerevisiae) or concentrated fractions of such extracts; Preferably, synthetic sweeteners, preferably synthetic sweeteners, selected from the group consisting of magap, sodium cyclamate or other physiologically acceptable salts of cyclamic acid, acesulfame potassium (acesulfam K); neohesperidin dihydrochalcone, naringin dihydrochalcone, saccharin, saccharin sodium salt, aspartame, superaspartame, neotam, alitam, advantam, perillartine, sucralose, luguduname, carrelame, sucrononate or sucrooctate or mixtures thereof; 9. The aroma composition according to claim 7 or claim 8, comprising at least one compound that provides sweetness selected from the group consisting of:

10. The aroma composition according to any one of claims 7 to 9, further comprising a flavor material.

11. 1. A method for reducing bitterness and / or improving mouthfeel and / or reducing astringency and / or improving sweetness intensity of a preparation containing phloretin, comprising: i. Providing a preparation comprising phloretin; ii. adding naringenin in an amount such that the weight ratio of phloretin to naringenin is 1:5 to 5:1, preferably 1:3 to 3:1, more preferably 1:1.5 to 1.5:1; iii. Obtaining a preparation having reduced bitterness and / or improved mouthfeel and / or reduced astringency and / or improved sweetness intensity compared to a similar preparation not containing naringenin; Including, As a prerequisite, If the preparation contains 30 ppm phloretin, naringenin is not added in the amount of 30 ppm; If the preparation contains 15 ppm phloretin, naringenin is not added in an amount of 15 ppm. method.

12. 12. The method according to claim 11, wherein the naringenin added in step ii is added in an amount of 10 ppm to 100 ppm, preferably 16 ppm to 80 ppm, most preferably 20 ppm to 50 ppm, based on the total amount of the preparation.

13. 13. The method according to claim 11 or claim 12, wherein the preparation is selected from the group consisting of aromatic compositions, preparations intended for nutritional, recreational or cosmetic or pharmaceutical purposes, and semi-finished products for producing such preparations.

14. A semi-finished product for producing a preparation intended for nutritional, recreational or cosmetic or pharmaceutical purposes, said semi-finished product comprising: The aroma composition according to any one of claims 7 to 10. or 10 ppm to 100 ppm, preferably 16 ppm to 80 ppm, most preferably 20 naringenin in an amount of 10 ppm to 100 ppm, preferably 15 ppm to 50 ppm; phloretin in an amount of from 20 ppm to 50 ppm, most preferably from 20 ppm to 50 ppm; Including, As a prerequisite, If the preparation contains 30 ppm phloretin, naringenin is not contained in an amount of 30 ppm; If the preparation contains 15 ppm phloretin, naringenin is not contained in an amount of 15 ppm. Semi-finished product.

15. The aroma composition according to any one of claims 7 to 10. or A semi-finished product according to claim 14, or Naringenin in an amount of 10 ppm to 100 ppm, preferably 16 ppm to 80 ppm, and most preferably 20 ppm to 50 ppm, and phloretin in an amount of 10 ppm to 100 ppm, preferably 15 ppm to 80 ppm, and most preferably 20 ppm to 50 ppm; Including, As a prerequisite, If the preparation contains 30 ppm phloretin, naringenin is not contained in an amount of 30 ppm; If the preparation contains 15 ppm phloretin, naringenin is not contained in an amount of 15 ppm. Products intended for nutritional, recreational, cosmetic or medicinal purposes.

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