Use of 3-(3-Hydroxy-4-Methoxy-Phenyl)-1-(2,4,6-Trihydroxy-Phenyl)-Propan-1-one

Abstract

Aroma composition comprising a compound of formula (I) or a salt of the compound of formula (I) or a mixture comprising or consisting of a plurality of salts of the compound of formula (I), or a mixture comprising the compound of formula (I) and a salt or a plurality of salts of the compound of formula (I).

Description

AREA OF INVENTION

[0001] Disclosed is the use of 3-(3-hydroxy-4-methoxyphenyl)-1-(2,4,6-trihydroxyphenyl)-propan-1-one (compound of formula (I)), hereinafter referred to as hesperetin dihydrochalcone (I), where (I) is understood as referring to formula (I), or of a salt of hesperetin dihydrochalcone (I), or of a mixture comprising or consisting of several salts of hesperetin dihydrochalcone (I), or of a mixture comprising or consisting of hesperetin dihydrochalcone (I) and one or more salts of hesperetin dihydrochalcone (I) for (i) Masking, reducing or suppressing an unpleasant taste sensation, preferably a bitter, sour and / or astringent taste sensation of unpleasant-tasting substances or mixtures of substances, and in particular of bitter-tasting substances or mixtures of substances, and in particular the bitter taste sensation of bitter-tasting substances, and / or (ii) Modulation of taste impressions selected from the group consisting of cooling, sweet, umami, fruity and spicy notes of cooling, sweet, umami, fruity or spicy tasting substances or mixtures of substances.

[0002] The present invention relates to flavor compositions containing hesperetin dihydrochalcone (I) or a salt of hesperetin dihydrochalcone (I) or a mixture comprising or consisting of several salts of hesperetin dihydrochalcone (I), or a mixture comprising or consisting of hesperetin dihydrochalcone (I) and a salt or several salts of hesperetin dihydrochalcone (I).

[0003] The present invention also relates to preparations, in particular preparations that serve for nutrition, as food supplements, for oral care or enjoyment, as cosmetics or medicinal products for oral administration, as well as intermediate products containing such an aroma composition.

[0004] Furthermore, a method for producing such aroma compositions, such preparations or such intermediate products is disclosed herein.

[0005] Furthermore, a method for masking, reducing or suppressing an unpleasant taste impression, preferably a bitter, sour and / or astringent taste impression of unpleasant tasting substances or mixtures of substances, and in particular the bitter taste impression of bitter tasting substances, is disclosed.

[0006] Furthermore, a method for modulating taste impressions selected from the group consisting of cooling, sweet, umami, fruity and spicy notes of cooling, sweet, umami, fruity or spicy tasting substances or mixtures of substances is revealed here.

[0007] Further aspects of the present invention and preferred embodiments will become apparent from the following description and the attached claims. STATE OF THE ART

[0008] Foods and beverages with a high sugar content (especially sucrose (=sugar), lactose, glucose, or fructose, or mixtures thereof) are generally preferred by consumers for their sweetness. On the other hand, it is known that a high content of easily metabolized carbohydrates leads to a sharp rise in blood sugar levels and the formation of fat deposits, ultimately resulting in health problems such as overweight, obesity, insulin resistance, type 2 diabetes, and its associated complications. To make matters worse, many of these carbohydrates can also negatively impact dental health, as they are broken down in the oral cavity by certain types of bacteria into lactic acid, which can attack the enamel of both young and adult teeth (caused by tooth decay).

[0009] It has therefore long been a goal to reduce the sugar content of food and / or beverages to the absolute minimum or below. One such measure is the use of sweeteners. These are substances that have no or very little caloric value in themselves and simultaneously produce a strong sweet taste sensation; these substances are generally not cariogenic (an overview can be found, for example, in the Journal of the American Dietetic Association 2004, 104 (2), 255-275).

[0010] So-called bulk sweeteners such as sorbitol, mannitol or other sugar alcohols are indeed exceptional sweeteners to a certain extent and can also partially replace the other properties of sugar, but if consumed too frequently, they can cause osmotically induced digestive problems in some people.

[0011] While non-nutritive, high-intensity sweeteners are well-suited for sweetening foods due to their low concentrations, they often exhibit taste problems. These include a time-intensity profile that differs from sugar (e.g., sucralose, steviosides, cyclamate), a bitter and / or astringent aftertaste (e.g., acesulfame K, saccharin, stevioside, rebaudioside), and / or pronounced additional flavors (e.g., ammonium glycyrrhizic acid salt). Some of these sweeteners are not particularly heat-stable (e.g., thaumatin, brazzein, monellin), not stable in all applications (e.g., aspartame), and some have a long-lasting sweetening effect (strong sweet aftertaste, e.g., saccharin, sucralose).An alternative – without the use of non-nutrient sweeteners – is to reduce the sugar content of food and / or beverages and to use substances with weak sensory or imperceptible effects that indirectly or directly enhance the sweetness.

[0012] In WO 2007 / 014879 A1, the use of hesperetin and in WO 2007 / 107596 A1, phloretin, are recommended as enhancers of the sweet taste of sugar-reduced food or beverage preparations. Occasionally, however, the comparatively weak enhancement of sweetness in foods and beverages, such as yogurt products, with high protein content, especially denatured proteins or polysaccharides, can be a disadvantage when using hesperetin and phloretin. Hesperetin also has the disadvantage of not being sufficiently effective in highly acidic and carbonated applications such as lemonades and cola drinks.

[0013] Furthermore, food and beverages often contain various unpleasant-tasting substances, such as bitter substances, highly acidic substances, and astringents. These are desirable and characteristic in moderation (e.g., caffeine in tea or coffee, tannins in red wine or green tea, quinine in so-called bitter lemon drinks, saponins or isoflavonoids or their glycosides in soy milk, hop extracts in beer, fruit acids or food acids in sweet fruit juices). However, they can also be highly detrimental (e.g., flavonoid glycosides and limonoids in citrus juices, the bitter and / or astringent aftertaste of many artificial sweeteners such as aspartame or saccharin, hydrophobic amino acids and / or peptides in cheese, fruit acids or food acids without sufficient mitigation by sweet flavorings, e.g., in lactic acid dairy products). Often, the unpleasant taste is further intensified by unpleasant odors. B.Soy milk, which often has a bitter and astringent taste, also has a note generally described as "beany" that is considered unpleasant.

[0014] A bitter taste is regularly caused by certain substances that bind to specific bitter receptors on taste cells (located in the so-called taste buds on the tongue) and send a signal to the brain via neurochemical cascades, triggering a defense reaction and a negative taste impression (cf. Wolfgang Meyerhof, Reviews of Physiology, Biochemistry and Pharmacology 2005, 154, 37-72).

[0015] An astringent taste is usually caused by the precipitation of proline-rich proteins in saliva by astringents, such as metal salts or tannins. The normally homogeneous saliva, which acts as a lubricant, then contains denatured proteins that reduce its lubricity, leaving a rough or dry feeling in the mouth that is also perceived as astringent (Isabelle Lesschaeve, Ann C. Noble, American Journal of Clinical Nutrition 2005, 81, 330S-335S).

[0016] The sour taste is caused by protic acids. The so-called titratable proton concentration is more crucial than the pH value for the perceived sourness: A hydrochloric acid solution with the same pH value as an malic acid solution tastes far less sour. Traditionally, the aversive sour taste is significantly reduced by combining it with sweet flavorings, especially sugar, or with salty-tasting substances, especially sodium chloride, while the sour taste is perceived as much more unpleasant when combined with bitter or astringent substances. However, sweet-tasting substances (e.g., sweeteners) are regularly used in comparatively high concentrations—generally in an amount that, in terms of its sweet taste, would correspond to at least a 2 wt% aqueous sucrose solution—to achieve a significant reduction in the sour taste.

[0017] Some fruit acids, especially citric acid, succinic acid, malic acid and tartaric acid, produce a sensory impression described as astringent in addition to the sour taste.

[0018] In some foods, particularly those made from sweet and sour fruits or vegetables (e.g., fruit juices, fruit preparations, and foods made from them) and in products produced by fermentation with acid-forming microorganisms (e.g., yogurt, ghee, kefir, soy yogurt, sauerkraut, sourdough bread, sausage, sour milk, cheese, mixed pickles, and soft drinks containing lactobionic or glucuronic acid), acidity is necessary to create microbial stability. To a certain extent, this is acceptable from a taste perspective, but in many cases, there is a desire to achieve a reduced sour taste without compromising the pH required for shelf life. Consideration should also be given to foods where the pH is adjusted with fruit acids or food acids to achieve sufficient microbial or antioxidant stability (e.g.,Apple juice with ascorbic acid, soft drinks with citric or phosphoric acid, dressings and ketchup with acetic acid), but the sour taste is regularly perceived as too strong and should therefore be reduced sensorially.

[0019] In summary, it can be stated that there are various foods that produce an excessively high, i.e., higher than desired, acidic sensory impression, caused by the natural concentration of fruit acids, acids formed through fermentation, or acids added for stability reasons, and where the pH value of the foods is adjusted for technological reasons (microbial stability, antioxidant stability, etc.).

[0020] Prior art describes how certain proteins, such as miraculin, can convert the sour taste sensation to a sweet taste sensation in the presence of acids (http: / / de.wikipedia.org / wiki / Miraculin). However, because this conversion to a sweet taste is undesirable in non-sweet applications, this solution is only of limited use and, moreover, lasts too long (2-4 hours), so this effect is only of very limited application.

[0021] Non-nutrient-containing, high-intensity sweeteners often have taste problems. The steviol glycosides naturally occurring in Stevia spp. or Rubus spp. (e.g., stevioside, rebaudioside AZ [A, B, C, D, E, F, G, H, I, O, M, N, V, W, X, Z, KA, etc.], steviolbioside, dulcoside A, dulcoside B, rubusoside, suavioside A, B, and GJ) are indeed very good sweeteners, but at the concentrations required for sufficient sweetness (e.g., 400–600 ppm for rebaudioside A [purity >90%] in soft drinks to achieve a sweetness equivalent to a sucrose concentration of 10% by weight), they already exhibit a pronounced licorice-like and unpleasantly bitter and astringent aftertaste.

[0022] Particularly in sweet, calorie-free or low-calorie beverages produced using such sweeteners, this unpleasant aftertaste often reduces sensory acceptance and should therefore be masked.

[0023] Several options are offered in the literature for this purpose. For example, US 2004 / 0142084 describes alkali metal hydrogen sulfates as masking agents. However, these significantly increase the acidity in applications. US 3,924,017 proposes caffeic acid derivatives for masking. The disadvantage is that caffeic acid itself has a slightly bitter taste and slightly suppresses sweetness, so more sweeteners would have to be used.

[0024] In WO 2006 / 087991, the unpleasant taste is suppressed by alkamides such as spilanthol; however, the tingling effect of this group of substances is often not desired, so they are not widely used.

[0025] An improvement in taste properties, particularly with regard to the problem of the aftertaste of non-nutrient-rich, high-intensity sweeteners, can be achieved through the use of tannic acid, e.g., as described in WO 98 / 20753, or phenolic acids, e.g., as described in US 3,924,017. However, these substances are not particularly stable in applications due to their catechin units and, as typical astringents, intensify a bitter and / or astringent off-flavor and / or aftertaste.

[0026] Not only the aforementioned steviol glycosides, but also other substances that have a bitter taste or aftertaste can significantly reduce the quality of food or beverages (e.g., flavonoid glycosides and limonoids in citrus juices, artificial sweeteners such as aspartame or saccharin, hydrophobic amino acids and / or peptides in cheese), even if substances with such flavors may be desirable in moderation and characteristic of such food or beverages (e.g., caffeine in tea and coffee, quinine in so-called bitter lemon drinks, hop extracts in beer).

[0027] In particular, to reduce the natural content of bitter substances, post-treatment is often necessary, e.g., extractive, as in the decaffeination of tea or coffee, or enzymatic, as in the treatment of orange juice with a glycosidase to break down the bitter substance naringin, or the use of special peptidases in the ripening of cheese. This treatment puts a strain on the product, generates waste products, and also causes, for example, solvent residues and other residues (enzymes) in the products.

[0028] The relationship between structure and sweetness was investigated as early as 1979 (J. Chem. Senses 1979, 4(1), 35-47). It was found that the 3-hydroxy-4-methoxyphenyl group is an important prerequisite for a strong sweetener, and that reversing the substituents is associated with a loss of sweetness. The intensely sweet-tasting dihydrochalcone (2) and the surprisingly tasteless dihydrochalcone (3) are presented in this publication. The hesperetin dihydrochalcone (I) itself, as well as possible masking or sweetening-enhancing properties of these compounds, are not described.

[0029] Compound (I) itself is known from the literature and is described, among other places, in J. Agric. Food Chem. 1977, 25(4), 763-772, as a sweet-tasting substance. However, this publication focuses on sulfonate derivatives of hesperet dihydrochalcone (I) and their sensory evaluation. Further sensory effects of compound (I) are not described.

[0030] Compound (I) is also mentioned in the publication J. Med. Chem. 1981, 24(4), 408-428, which also deals with sweeteners based on a dihydrochalcone structure. Here, too, the importance of the 3-hydroxy-4-methoxyphenyl group for a pronounced sweetness sensation is emphasized, and furthermore, it is assumed that the 2,6-dihydroxy substitution pattern of the other aromatic compounds is particularly important for a strong sweetness sensation. No other sensory effects of compound (I) are described.

[0031] Compound (I) and other ring-substituted hesperetin dihydrochalcones are described in J. Agric. Food. Chem. 1991, 39(1), 44-51, and their sweetness was compared with that of a 6% aqueous sucrose solution, with a similar or weaker sweetness reported for compound (I). No other sensory effects of compound (I) are described.

[0032] J. Chem. Soc., Perkin Trans. 2 1998, 6, 1449-1454 describes a three-dimensional binding site model for the structurally uncharacterized sweet taste receptor using pseudoreceptor modeling. The receptor model was derived from 17 sweetener compounds of the isovanillyl class (4-methoxy-3-hydroxybenzyl), including compound (I), as a training set and consists of nine key amino acid residues embedded in a hydrophobic receptor cavity. Quant. Struct.-Act. Relat. 2001, 20(1), 3-16 describes the results obtained by applying statistical models to develop QSARs for isovanillyl derivatives. Compound (I) is described here; however, it was not included in the sensory evaluation.

[0033] It is important to note that the literature relating to compound (I) focuses on the development of potential sweeteners. There is no evidence of an effect of compound (I) in combination with sweetness-modulating substances or other sweeteners, nor of an effect of compound (I) in combination with other fragrances or flavorings (e.g., bitter-tasting substances).

[0034] In this context, it is only known that the sweetening properties of dihydrochalcone compounds differ from one another.

[0035] Patent application WO2007 / 107596 A1 describes 4-hydroxydihydrochalcones of formula (7) and their salts for intensifying sweet sensory impressions, wherein R1, R2, R3 and R4 independently represent H, OH and O-alkyl (with preferably 1-4 carbon atoms, i.e., preferably C1 to C4 alkoxy), provided that at least one of the R1, R2 or R3 substituents represents OH. However, a 4-hydroxy substitution was necessary for the sweetness-enhancing effects found here.

[0036] For many pharmaceutical agents, it is particularly important to suppress an unpleasant, especially bitter, taste, as this can significantly increase the willingness of patients, especially those sensitive to bitter tastes such as children, to take the medication orally. Many pharmaceutical agents, such as fluoroquinolone antibiotics, beta-lactam antibiotics, ambroxol, propylthiouracil (PROP), aspirin (acetylsalicylic acid), salicin, paracetamol (acetaminophen), ibuprofen, naproxen, guafenesin, omeprazole, pantoprazole, dextromorphine, or quinine, to name just a few, have a pronounced bitter, astringent, and / or metallic taste or aftertaste.

[0037] Therefore, there is a need to provide substances that, in low concentrations, effectively enhance the sweet taste impression of sweeteners, preferably the sweet taste impression of sugar-reduced foods and beverages, especially sugar-reduced foods and beverages with a low pH value, without adversely affecting the taste profile.

[0038] Furthermore, there is a need for substances that are able to mask, reduce or suppress the bitter, sour and / or astringent taste of compounds, also in preparations, especially in food and beverages and pharmaceuticals, preferably without significantly impairing the otherwise desired taste of these preparations.

[0039] It was therefore the primary object of the present invention to provide substances which, in low concentrations, can mask, reduce or suppress an unpleasant, preferably bitter and / or sour and / or astringent taste impression of unpleasant-tasting substances or mixtures of substances, preferably bitter and / or sour and / or astringent-tasting substances or mixtures of substances, in particular the bitter impression of bitter-tasting substances.

[0040] Another objective of the present invention was to provide substances which, in low concentrations, are able to modulate the taste impressions selected from the group consisting of cooling, sweet, umami, fruity and spicy notes of cooling, sweet, umami, fruity or spicy tasting substances or mixtures of substances.

[0041] A further objective of the present invention was to provide substances which, in low concentrations, are able to mask, reduce or suppress an unpleasant taste impression, preferably the bitter and / or sour and / or astringent taste impression of unpleasant-tasting substances or mixtures of substances, in particular the bitter impression of bitter- and / or sour and / or astringent-tasting substances or mixtures of substances, and to modulate the taste impressions selected from the group consisting of cooling, sweet, umami, fruity and spicy notes of cooling, sweet, umami, fruity or spicy-tasting substances or mixtures of substances.

[0042] A further objective of the present invention was to provide substances which, in low concentrations, mask, reduce or suppress an unpleasant taste impression, preferably a bitter and / or sour and / or astringent taste impression of unpleasant-tasting substances or mixtures of substances, and in particular the bitter impression of bitter-tasting substances. and simultaneously - preferably synergistically - intensify the sweet taste impression of sweet-tasting substances or mixtures of substances, or of both sweet and bitter-tasting substances or mixtures of substances.

[0043] Another objective of the present invention was to provide substances which, in low concentrations, are able to modulate the taste impressions from the group of cooling, sweet, umami, fruity and spicy notes of cooling, sweet, umami, fruity or spicy tasting substances or mixtures of substances and at the same time - preferably synergistically - intensify the sweet taste impression of sweet tasting substances or mixtures of substances or mixtures of substances or of substances that taste both sweet and bitter.

[0044] A further objective of the present invention was to provide substances which, in low concentrations, can mask, reduce or suppress an unpleasant taste impression, preferably a bitter and / or sour and / or astringent taste impression of unpleasant-tasting substances or mixtures of substances, preferably of bitter and / or sour and / or astringent-tasting substances or mixtures of substances, in particular the bitter impression of bitter-tasting substances and at the same time - preferably synergistically - intensify the sweet taste impression of sweet-tasting substances or mixtures of substances or mixtures of substances, or of both sweet and bitter-tasting substances or mixtures of substances, and furthermore be able to modulate the taste impressions selected from the group consisting of cooling, sweet, umami, fruity and spicy notes of cooling, sweet, umami, fruity or spicy-tasting substances or mixtures of substances. DESCRIPTION OF THE INVENTION

[0045] The use of 3-(3-hydroxy-4-methoxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one (compound of formula (I)), hereinafter referred to as hesperetin dihydrochalcone (I), is disclosed. or - a salt of hesperet dihydrochalcone (I) or a mixture containing or consisting of several salts of hesperet dihydrochalcone (I) or - a mixture containing or consisting of hesperet dihydrochalcone (I) and a salt or several salts of hesperet dihydrochalcone (I), for (i) Masking, reducing or suppressing an unpleasant taste sensation, preferably a bitter and / or sour and / or astringent taste sensation of unpleasant tasting substances or mixtures of substances, preferably of bitter and / or sour and / or astringent tasting substances or mixtures of substances, and in particular the bitter taste sensation of bitter tasting substances.

[0046] In our own investigations in the field of flavonoids and dihydrochalcones, it was surprisingly found that hesperetin dihydrochalcone (I) has a masking, reducing, or suppressing effect on unpleasant taste sensations selected from the group consisting of bitter, and / or sour, and / or astringent taste sensations, especially bitter taste sensations. Thus, it was surprisingly found that hesperetin dihydrochalcone (I) is able to mask, reduce, or suppress the bitterness of prominent bitter components (see Example 2).

[0047] The use of hesperet dihydrochalcone (I) or is also disclosed. - a salt of hesperetin dihydrochalcone (I) or a mixture containing or consisting of several salts of hesperetin dihydrochalcone (I), or - a mixture containing or consisting of hesperet dihydrochalcone (I) and a salt or several salts of hesperet dihydrochalcone (I), for (ii) Modulating taste sensations selected from the group consisting of cooling, sweet, umami, fruity and spicy notes from cooling, sweet, umami, fruity or spicy tasting substances or mixtures of substances.

[0048] According to the present disclosure, the expression "modulating taste impressions selected from the group consisting of cooling, sweet, umami, fruity, and spicy notes of cooling, sweet, umami, fruity, or spicy tasting substances or mixtures of substances" means the improvement of the taste profile, preferably with regard to a faster and better perception of cooling, umami, fruity, and spicy notes. Accordingly, it is possible to modulate the fruity and spicy aromas and notes so that a more authentic profile can be achieved.

[0049] The use of hesperetin dihydrochalcone (I) or is also disclosed. - a salt of hesperetindihydrochalcone (I) or a mixture comprising or consisting of several salts of hesperetindihydrochalcone (I), or - a mixture containing or consisting of hesperet dihydrochalcone (I) and a salt or several salts of hesperet dihydrochalcone (I), for (i) Masking, reducing or suppressing an unpleasant taste sensation, preferably a bitter and / or sour and / or astringent taste sensation of unpleasant-tasting substances or mixtures of substances, and in particular of bitter and / or sour and / or astringent-tasting substances or mixtures of substances, and (ii) Modulating taste sensations selected from the group consisting of cooling, sweet, umami, fruity and spicy notes from substances or mixtures of substances that taste cooling, sweet, umami, fruity or spicy.

[0050] In our own investigations in the field of flavonoids and dihydrochalcones, we surprisingly found that hesperetin dihydrochalcone (I) has a masking, reducing, or suppressing effect on an unpleasant taste sensation selected from the group consisting of bitter and / or sour and / or astringent taste sensations, especially bitter taste sensations, and furthermore, a positive effect on the taste profile of various compositions, especially flavoring compositions. None of the prior art documents suggest these effects, especially considering that none of these documents teach a modulating effect on taste sensations, particularly bitter, sour, astringent, cooling, umami, fruity, and spicy notes.

[0051] The use of hesperetin dihydrochalcone (I) or is also disclosed. - a salt of hesperet dihydrochalcone (I) or a mixture comprising or consisting of several salts of hesperet dihydrochalcone (I), or - a mixture containing or consisting of hesperet dihydrochalcone (I) and a salt or several salts of hesperet dihydrochalcone (I), for (i) Masking, reducing or suppressing an unpleasant taste sensation, preferably a bitter and / or sour and / or astringent taste sensation of unpleasant-tasting substances or mixtures of substances, and in particular of the bitter taste sensation of bitter-tasting substances, and at the same time (iii) Intensifying - preferably synergistically - the sweet taste impression of sweet-tasting substances or mixtures of substances or of substances that taste both sweet and bitter.

[0052] The use of hesperetin dihydrochalcone (I) or is also disclosed. - a salt of hesperet dihydrochalcone (I) or a mixture containing or consisting of several salts of hesperet dihydrochalcone (I), or - a mixture containing or consisting of hesperet dihydrochalcone (I) and a salt or several salts of hesperet dihydrochalcone (I), for (ii) Modulating taste sensations selected from the group consisting of cooling, sweet, umami, fruity and spicy notes from cooling, sweet, umami, fruity or spicy tasting substances or mixtures of substances, and at the same time (iii) Intensifying - preferably synergistically - the sweet taste impression of sweet-tasting substances or mixtures of substances or of substances that taste both sweet and bitter.

[0053] The use of hesperetin dihydrochalcone (I) or is also disclosed. - a salt of hesperetin dihydrochalcone (I) or a mixture containing or consisting of a variety of salts of hesperetin dihydrochalcone (I), or - a mixture containing or consisting of hesperet dihydrochalcone (I) and a salt or several salts of hesperet dihydrochalcone (I), for (i) Masking, reducing or suppressing an unpleasant taste sensation, preferably a bitter and / or sour and / or astringent taste sensation of unpleasant-tasting substances or mixtures of substances, and in particular of bitter and / or sour and / or astringent-tasting substances or mixtures of substances, and (ii) Modulating the taste sensations selected from the group consisting of cooling, sweet, umami, fruity and spicy notes from substances or mixtures of substances that taste cooling, sweet, umami, fruity or spicy, and at the same time (iii) Intensifying - preferably synergistically - the sweet taste impression of sweet-tasting substances or mixtures of substances or of substances that taste both sweet and bitter.

[0054] Hesperetin dihydrochalcone (I) is advantageously particularly well suited to mask, reduce or suppress an unpleasant taste sensation, especially a bitter taste sensation of a bitter-tasting substance (see application example 2).

[0055] Furthermore, hesperetin dihydrochalcone (I) is advantageously particularly well suited to intensifying the sweet taste of a sweet-tasting substance—preferably synergistically—and is readily accessible synthetically. A particularly advantageous sweetness-enhancing effect of compound (I) results when the sweet-tasting substance, whose sweet taste is to be intensified according to the invention—preferably synergistically—is a sugar, in particular sucrose, glucose, or fructose, or a combination of two or all of these sugars. This particularly advantageous synergistic sweetness-enhancing effect of hesperetin dihydrochalcone (I) is demonstrated below by way of example using the intensification of the sweet taste of sucrose (see Application Example 3).

[0056] Another disclosed use of hesperet dihydrochalcone (I) relates to the - preferably synergistic - enhancement of the sweet taste impression of a substance or mixture of substances that tastes both sweet and unpleasant, in particular bitter, sour and / or astringent, and the simultaneous reduction or masking of the unpleasant, in particular bitter, sour and / or astringent taste impression of the substance or mixture of substances that tastes both sweet and unpleasant, in particular bitter, sour and / or astringent.

[0057] Further disclosed is a use of hesperet dihydrochalcone (I) or a salt of hesperet dihydrochalcone (I) or a mixture comprising or consisting of a plurality of salts of hesperet dihydrochalcone (I), or a mixture comprising or consisting of hesperet dihydrochalcone (I) and a salt or a plurality of salts of hesperet dihydrochalcone (I), wherein the sweet taste impression of a sweet-tasting substance or mixture of substances or of a substance or mixture of substances that is both sweet and unpleasant, preferably bitter, and / or sour, and / or astringent, and in particular the bitter taste impression of bitter-tasting substances, is enhanced, preferably synergistically enhanced.

[0058] Preferably, hesperetin dihydrochalcone (I) or a salt of hesperetin dihydrochalcone (I) or a mixture comprising or consisting of several salts of hesperetin dihydrochalcone (I), or a mixture comprising or consisting of hesperetin dihydrochalcone (I) and one or more salts of hesperetin dihydrochalcone (I), is used in the manner described above in a flavoring composition or in a preparation selected from the group consisting of preparations that serve nutritional purposes as food supplements, for oral care or enjoyment, cosmetic preparations, in particular for use in the head area, pharmaceutical preparations for oral administration, flavoring mixtures and intermediates for use in one of the aforementioned flavoring compositions, preparations or semi-finished products for the manufacture of one of the aforementioned preparations.

[0059] The synthesis of compound (I) is possible, for example, via acidic hydrolysis starting from neohesperidin dihydrochalcone (see Example 1) by cleavage of the sugar residues rhamnose and glucose. J. Agric. Food Chem. 2005, 1782-1790 also describes this degradation of neohesperidin dihydrochalcone by human intestinal bacteria. DE 2148332 A1 also describes the synthesis of compound (I) by conversion of hesperidin into a soluble salt by treatment of hesperidin with a 10% aqueous solution of KOH, subsequent reduction with hydrogen (Pd / C catalyst), and cleavage of the sugar residues under acidic conditions. Other alternatives for the synthesis of compound (I) starting from benzyl-protected precursors by reduction with hydrogen under the addition of a catalyst (e.g. Pd / C) are also conceivable (J. Agric. Food. Chem 1991, 39(1), 44-51).However, the use of different protecting groups, different bases, different reducing agents and the execution of an acid-catalyzed aldol reaction are also possible and obvious to the person skilled in the art.

[0060] In the salts of hesperetin dihydrochalcone (I) to be used according to the present disclosure, one, two, or three hydroxyl groups can be deprotonated, wherein a corresponding number of countercations are present, the latter preferably being selected from the group consisting of: singly positively charged cations of the first main and subgroups, ammonium ions, trialkylammonium ions, doubly positively charged cations of the second main and subgroups, and triply positively charged cations of the third main and subgroups, as well as mixtures thereof. Preferably, these countercations are cations selected from the group consisting of Na + , K + , NH (4) ( +) , Ca 2+ , Mg2+ , Al 3+ and Zn 2+ , especially preferably selected from the group consisting of Na + and K + .

[0061] Consequently, the use of a salt or a mixture of is further disclosed. - two or more different salts of hesperet dihydrochalcone (I) or - Hesperetin dihydrochalcone (I) and one or more different salts of hesperetin dihydrochalcone (I) as described above, wherein the countercation(s) of one, several or all salts of hesperetin dihydrochalcone (I) is from the Na group + , K + , NH (4) ( +) , Ca 2+ , Mg 2+ , Al 3+ and Zn 2+ are selected, especially preferably from the Na group + and K + are selected.

[0062] The above applies accordingly to the salts underlying hesperetin dihydrochalcone (I).

[0063] In our own investigations in connection with the present invention, it was surprisingly found that hesperet dihydrochalcone (I) (advantageously even in very low concentrations) can (ideally completely) mask or (at least) reduce the unpleasant taste sensation, in particular the bitter taste sensation of a number of unpleasant or bitter-tasting substances, especially methylxanthines, such as caffeine, alkaloids, such as quinine, flavonoids, such as catechins, naringin, neohesperidin, phenolic glycosides, such as salicin, arbutin, amygdalin or phenols, such as hydroxytyrosol or oleuropein, inorganic salts, such as potassium chloride or magnesium sulfate, pharmaceutical agents, such asFluoroquino-ion antibiotics, beta-lactam antibiotics, ambroxol, propylthiouracil [PROP], aspirin (acetylsalicylic acid), salicin, paracetamol (acetaminophen), ibuprofen, naproxen, guafenesin, omeprazole, pantoprazole, dextromorphine or quinine, or steviol glycosides, such as stevioside or rebaudioside. The masking or reduction of the bitter taste of the compounds mentioned in this paragraph is also preferred according to the invention.

[0064] It is particularly advantageous if the hesperet dihydrochalcone (I) used according to the invention does not have complex-forming properties. Hesperet dihydrochalcone (I) is therefore advantageously particularly well suited to both synergistically enhancing a pleasant taste impression, especially the sweet taste impression of a sweet-tasting substance, and masking or reducing an unpleasant taste impression, especially the bitter taste impression of a bitter-tasting substance, preferably with both effects occurring simultaneously.

[0065] Furthermore, the use is revealed (a) of hesperetin dihydrochalcone (I), or - a salt of hesperet dihydrochalcone (I) or a mixture containing or consisting of several salts of hesperet dihydrochalcone (I), or - a mixture containing or consisting of hesperet dihydrochalcone (I) and one or more salts of hesperet dihydrochalcone (I), as described above, in a mixture comprising at least one or more of the substances selected from the group consisting of substance(s) (c) and (d) or mixtures thereof, wherein - Substance(s) (c) one or more unpleasant-tasting substances, preferably bitter, sour and / or astringent-tasting substances, in particular bitter-tasting substances, means - Substance(s) (d) one or more substances that taste both sweet and unpleasant, in particular bitter-tasting substances; and / or - one or more sweet-tasting substances (b) (a) to intensify - preferably synergistically intensify - the sweet taste of the substance(s) (b) or (d), and / or (b) to mask or reduce the unpleasant taste of the unpleasant-tasting substance(s) (c) or (d).

[0066] Furthermore, the use is revealed (a) of hesperetin dihydrochalcone (I), or - a salt of hesperet dihydrochalcone (I) or a mixture containing or consisting of several salts of hesperet dihydrochalcone (I), or - a mixture containing or consisting of hesperet dihydrochalcone (I) and one or more salts of hesperet dihydrochalcone (I), as described above, in a mixture comprising at least one or more of the substances selected from the group consisting of substance(s) (c) and (d) or mixtures thereof, wherein - Substance(s) (c) means one or more unpleasant-tasting substances, preferably bitter, sour and / or astringent-tasting substances, in particular bitter-tasting substances. - Substance(s) (d) means one or more substances that taste both sweet and unpleasant, especially bitter; and / or - one or more sweet-tasting substances (b) (a) to intensify - preferably synergistically intensify - the sweet taste of the substance(s) (b) or (d), and (b) to mask or reduce the unpleasant taste of the unpleasant-tasting substance(s) (c) or (d).

[0067] Furthermore, the use is revealed (a) of hesperetin dihydrochalcone (I), or - a salt of hesperet dihydrochalcone (I) or a mixture containing or consisting of several salts of hesperet dihydrochalcone (I), or - a mixture containing or consisting of hesperet dihydrochalcone (I) and one or more salts of hesperet dihydrochalcone (I), as described above, in a mixture comprising at least one or more of the substances selected from the group consisting of substance(s) (c) and (d) or mixtures thereof, wherein - Substance(s) (c) means one or more unpleasant-tasting substances, preferably bitter, sour and / or astringent-tasting substances, in particular bitter-tasting substances. - Substance(s) (d) one or more substances that taste both sweet and unpleasant, in particular bitter-tasting substances; and / or - one or more sweet-tasting substances (b), and / or - one or more substances with a taste sensation selected from the group consisting of cooling, umami, fruity and savory taste sensations or mixtures thereof, (a) to intensify - preferably synergistically intensify - the sweet taste of the substance(s) (b) or (d), and / or (b) to mask or reduce the unpleasant taste of the unpleasant-tasting substance(s) (c) or (d), in particular a bitter taste, and / or (c) for modulating the taste impression, selected from the group consisting of cooling, sweet, umami, fruity and savory taste impressions or mixtures thereof.

[0068] Surprisingly, it was found that the use of hesperetin dihydrochalcone (I) improves the flavor profile in the above-mentioned blends, particularly with regard to a faster and better perception of cooling, sweet, umami, fruity and spicy notes.

[0069] Furthermore, the use is revealed (a) of hesperetin dihydrochalcone (I), or - a salt of hesperet dihydrochalcone (I) or a mixture containing or consisting of several salts of hesperet dihydrochalcone (I) or - a mixture containing or consisting of hesperet dihydrochalcone (I) and one or more salts of hesperet dihydrochalcone (I), as described above, in a mixture comprising at least one or more of the substances selected from the group consisting of substance(s) (c) and (d) or mixtures thereof, wherein - Substance(s) (c) means one or more unpleasant-tasting substances, preferably bitter, sour and / or astringent-tasting substances, in particular bitter-tasting substances. - Substance(s) (d) means one or more substances that taste both sweet and unpleasant, especially bitter; and / or - one or more sweet-tasting substances (b), and - one or more substances with a taste sensation selected from the group consisting of cooling, umami, fruity and savory taste sensations or mixtures thereof, (a) to intensify - preferably synergistically intensify - the sweet taste of the substance(s) (b) or (d), and (b) to mask or reduce the unpleasant taste of the unpleasant-tasting substance(s) (c) or (d), in particular a bitter taste, and (c) for modulating the taste impression, selected from the group consisting of cooling, sweet, umami, fruity and savory taste impressions or mixtures thereof.

[0070] Furthermore, the use is revealed (a) of hesperetin dihydrochalcone (I) or - a salt of hesperet dihydrochalcone (I) or a mixture comprising or consisting of several salts of hesperet dihydrochalcone (I), or - a mixture containing or consisting of hesperet dihydrochalcone (I) and one or more salts of hesperet dihydrochalcone (I), as described above, in a mixture comprising at least one or more of the substances selected from the group consisting of substance(s) (c) and (d) or mixtures thereof, wherein - Substance(s) (c) means one or more unpleasant-tasting substances, preferably bitter, sour and / or astringent-tasting substances, in particular bitter-tasting substances. - Substance(s) (d) means / mean one or more substances that taste both sweet and unpleasant, especially bitter-tasting substances; and - one or more sweet-tasting substances (b), and - one or more substances with a taste sensation selected from the group consisting of cooling, umami, fruity and savory taste sensations or mixtures thereof, (a) to intensify - preferably synergistically intensify - the sweet taste of the substance(s) (b) or (d), and (b) to mask or reduce the unpleasant taste impression of the unpleasant-tasting substance(s) (c) or (d), in particular a bitter-tasting impression, and (c) for modulating the taste impression, selected from the group consisting of cooling, sweet, umami, fruity and savory taste impressions or mixtures thereof.

[0071] The above regarding hesperetindihydrochalcone (I), its salts or mixtures comprising or consisting of several salts of hesperetindihydrochalcone (I), or mixtures comprising or consisting of hesperetindihydrochalcone (I) and one or more salts of hesperetindihydrochalcone (I), applies accordingly here.

[0072] Preferably, the mixture is a flavoring composition or preparation selected from the group of preparations used for nutrition, as a food supplement, for oral care or enjoyment, cosmetic preparations, in particular for use in the head area, pharmaceutical preparations intended for oral administration, flavoring mixtures for use in any of the aforementioned preparations or semi-finished products for the manufacture of any of the aforementioned preparations.

[0073] Sweet-tasting substances within the meaning of the present invention are in particular: - sweet-tasting carbohydrates (e.g. sucrose, trehalose, lactose, maltose, melicitose, 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), - sweet-tasting sugar alcohols (e.g. erythritol, threitol, arabitol, ribitol, xylitol, sorbitol, mannitol, dulcitol, lactitol), - sweet-tasting proteins (e.g., miraculin, pentadin, monellin, thaumatin, curculin, brazzein), - Sweeteners (e.g., Magap, sodium cyclamate, acesulfame K, neohesperidin dihydrochalcone, naringin hydrochalcone, saccharin, saccharin sodium salt, aspartame, superaspartame, neotame, sucralose, lugduname, carrelame, sucrononate, sucrooctate or naturally occurring sweeteners such as miraculin, curculin, monellin, mabinlin, thaumatin, curculin, brazzein, pentadin, D-phenylalanine, D-tryptophan or extracts or fractions obtained from natural sources containing these amino acids and / or proteins, neohesperidin dihydrochalcone, steviol glycosides, steviosides, steviolbioside, rebaudioside, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, Rebaudioside F, Rebaudioside G, Rebaudioside H, Rebaudioside I, Rebaudioside O, Rebaudioside M, Rebaudioside N, Rebaudioside V, Rebaudioside W, Rebaudioside Suavioside G, Suavioside H, Suavioside I, Suavioside J, Baiyunoside 1, Baiyunoside 2, Phlomisoside 1,Phlomisoside 2, Phlomisoside 3, Phlomisoside 4, Abrusoside A, Abrusoside B, Abrusoside C, Abrusoside D, Cyclocaryoside A, Cyclocaryoside I, Oslandin, Polypodoside A, Strogin 1, Strogin 2, Strogin 4, Selligueanine A, Dihydroquercetin-3-acetate, Perillartin, Telosmoside A, 15 , Periandrin IV, Pterocaryoside, Cyclocaryoside, Mukurozioside, trans-Anethole, trans-Cinnamaldehyde, Bryosides, Bryonosides, Bryonodulcosides, Carnosiflosides, Scandenosides, Gypenosides, Trilobtaine, Phloridzin, Dihydroflavanols, Hematoxylin, Cyanine, Chlorogenic acid, Albiziasaponin, Telosmosides, Gaudichaudioside, Mogrosides, Hernandulcine, Monatin, Glycyrrhetinic acid and their derivatives and salts, Phyllodulcin, Balansin A and Balansin B).

[0074] In addition to the sweet primary taste, sweet-tasting substances can have one or more further taste sensations (and / or olfactory sensations), in particular a non-sweet aftertaste. Primary taste, in this context, refers to the taste sensation that arises while the substance is in direct contact with the oral mucosa, especially the tongue (usually from a few seconds to a few minutes). Aftertaste refers to the taste sensation that remains after the oral cavity has been emptied by swallowing and / or spitting and can persist for a few minutes to a few hours due to the adhesion of substance residue.

[0075] As mentioned in the introduction, particularly sweet-tasting substances can also evoke unpleasant, especially bitter, taste sensations. To influence the taste sensations of such substances (d) that taste both sweet and unpleasant, especially bitter, hesperetin dihydrochalcone (I), or a salt of hesperetin dihydrochalcone (I), or a mixture comprising or consisting of several salts of hesperetin dihydrochalcone (I), or a mixture comprising or consisting of hesperetin dihydrochalcone (I) and one or more salts of hesperetin dihydrochalcone (I), are preferably used. The presence of other taste sensations of a substance, as well as the intensity of the primary taste itself, can vary, for example, depending on the concentration of the substance, the temperature, the pH value, and / or other substances present alongside it.

[0076] For example, the sweetness of stevioside or rebaudioside A or another steviol glycoside (as described above) depends on various factors such as temperature, pH, concentration, and the product being sweetened. In particular, depending on the concentration (at high concentrations, especially above 50 ppm, particularly between 50 and 2000 ppm, and especially between 100 and 1000 ppm), a bitter aftertaste occurs, which is generally undesirable. Within the scope of the present invention, stevioside or rebaudioside A are particularly preferably substances that taste both sweet and bitter (d).

[0077] Unpleasant, especially bitter, tasting substances with an additional sweet taste impression are, in the sense of the present invention, classified as both sweet and unpleasant tasting substances.

[0078] Within the scope of the present invention, corresponding taste impressions, characterized by an aftertaste, can also be assigned to the respective unpleasant taste impressions.

[0079] Therefore, unpleasant-tasting substances within the meaning of the present invention are: Substances with a bitter, sour, astringent, sticky, chalky, dusty, dry, mealy, rancid or metallic taste and - Substances with a corresponding (possibly long-lasting) aftertaste.

[0080] The sour, astringent, sticky, chalky, dusty, dry, mealy, rancid and / or metallic taste sensations are often accompanied by a bitter taste sensation.

[0081] Substances (c) that taste unpleasant, i.e. bitter, sour, astringent, sticky, chalky, dusty, dry, mealy, rancid or metallic, include, for example:

[0082] Xanthine alkaloids, xanthines (caffeine, theobromine, theophylline), alkaloids (quinine, quinine hydrochloride, brucine, strychnine, nicotine), phenolic glycosides (e.g., salicin, arbutin), flavonoid glycosides (e.g., hesperidin, naringin), chalcones or chalcone glycosides, hydrolyzable tannins (gallic or ellagic acid esters of carbohydrates, e.g., pentagalloylglucose), non-hydrolyzable tannins (possibly galloylated catechins or epicatechins and their oligomers, e.g., proanthyocyanidins or procyanidins, thearubigin), flavones (e.g., quercertin, taxifolin, myricetin), other polyphenols (gamma-oryzanol, caffeic acid or their esters), terpenoid bitter substances (e.g., sulfur dioxide ... B. Limonoids such as limonin or nomilin from citrus fruits, lupolone and humulone from hops, iridoids, secoiridoids), absinthin from wormwood, amarogentin from gentian, metal salts (potassium chloride, sodium sulfate, magnesium salts, iron salts, aluminum salts, zinc salts), pharmaceutical agents (e.g.Fluoroquino-ion antibiotics, beta-lactam antibiotics, ambroxol, propylthiouracil [PROP], aspirin (acetylsalicylic acid), salicin, paracetamol (acetaminophen), ibuprofen, naproxen, ambroxol, guafenesin, omeprazole, pantoprazole, dextromorphan or quinine), vitamins (e.g., vitamin H, B vitamins such as vitamins B1, B2, B6, B12, niacin, pantothenic acid), denatonium benzoate or other denatonium salts, sucralose octaacetate, urea, unsaturated fatty acids, especially unsaturated fatty acids in emulsions, amino acids (e.g., leucine, isoleucine, valine, tryptophan, proline, histidine, tyrosine, lysine or phenylalanine, especially the respective L-enantiomers of leucine), isoleucine, valine, tryptophan, proline, histidine, tyrosine, lysine or phenylalanine), peptides (especially peptides with an amino acid from the group L-leucine, L-isoleucine, L-valine, L-tryptophan, L-proline or L-phenylalanine at the N- or C-terminus).

[0083] Substances, in particular flavorings or flavorings, often have a bitter, sour, astringent, cardboard-like, chalky, dusty, dry, mealy, rancid, and / or metallic aftertaste, even though they have a non-unpleasant (primary) taste as defined above (i.e., sweet, salty, spicy, sour, etc.) and / or odor. These flavorings or flavorings with an unpleasant (after)taste are unpleasant-tasting substances (c) or, in particular (if they have a sweet (primary) taste), both sweet and unpleasant-tasting substances (d) as defined in the present invention. These flavorings or flavorings are selected, in particular, from the group of sweeteners (as described above) or sugar substitutes; that is, these flavorings or flavorings have a sweet (primary) taste.Specific examples of such flavorings or flavorings are aspartame, neotame, superaspartame, saccharin, sucralose, tagatose, monellin, stevioside, rebaudioside, especially rebaudioside A, mogroside, particularly mogroside V, thaumatin, miraculin, glycyrrhizin, glycyrrhetinic acid or derivatives thereof, cyclamates, or the pharmaceutically acceptable salts of the aforementioned compounds. The flavorings or flavorings are preferably both sweet and unpleasant / bitter tasting substances (d) for the applications according to the invention. The unpleasant taste of these substances, in particular a bitter taste, can be particularly effectively masked or reduced when used according to the invention (as described above).

[0084] Other unpleasant-tasting substances (c) or substances that taste both sweet and unpleasant (d), whose unpleasant (after-)taste can be advantageously masked or reduced according to the invention, are, for example, aromatic substances that have a sweet taste impression and are preferably selected from the group consisting of: vanillin, ethyl vanillin, 2-hydroxy-4-methoxybenzaldehyde, ethyl vanillin isobutyrate (=3-ethoxy-4-isobutyryloxybenzaldehyde), furaneol ®(2,5-Dimethyl-4-hydroxy-3(2H)-furanon) und deren Derivate (z.z. B. Homofuranol, 2-Ethyl-4-hydroxy-5-methyl-3(2H)-furanon), Homofuronol (2-Ethyl-5-methyl-4-hydroxy-3(2H)-furanon und 5-Ethyl-2-methyl-4-hydroxy-3(2H)-furanon), Maltol und dessen Derivate (z. B. Ethylmaltol), Cumarin und seine Derivate, gamma-Lactone (z. B. gamma-Undecalacton, gamma-Nonalacton), delta-Lactone (z. B. 4-Methyl-delta-lacton, Massoilacton, Delta-decalacton, Tuberolacton), Methylsorbat, Divanillin, 4-Hydroxy-2(oder 5)-ethyl-5(oder 2)-methyl-3(2H)furanon, 2-Hydroxy-3-methyl-2-cyclopentenone, 3-Hydroxy-4,5-dimethyl-2(5H)-furanon, Fruchtester und Fruchtlactone (z.g.n-Butylacetat, Isoamylacetat, Ethylpropionat, Ethylbutyrat, n-Butylbutyrat, Isoamylbutyrat, Ethyl-3-methylbutyrat, Ethyl-n-hexanoat, Allyl-n-hexanoat, n-Butyl-n-hexanoat, Ethyl-n-octanoat, Ethyl-3-methyl-3-phenylglycidat, Ethyl-2-trans-4-cis-decadienoat), 4-(p-Hydroxyphenyl)-2-butanon, 1,1-Dimethoxy-2,2,5-trimethyl-4-hexan, 2,6-Dimethyl-5-hepten-1-al und Phenylacetaldehyd.

[0085] A further disclosed use is as described above, wherein the bitter-tasting substance (c) or the sweet-and-bitter-tasting substance (d) is selected from the group consisting of steviol glycosides, in particular stevioside and rebaudiosides. The bitter-tasting substance (c) or the sweet-and-bitter-tasting substance (d) is preferably selected from the group consisting of rebaudioside A, rubusoside, dulcoside, mogroside, phyllodulcin, glycyrrhetinic acid, or extracts of Stevia spp. (in particular Stevia rebaudiana), Luo Han Guo, Rubus suavissimus, Hydrangea dulcis, Mycetia balansae, or Glycyrrhyza glabra.

[0086] By using hesperetin dihydrochalcone (I) or a salt of hesperetin dihydrochalcone (I) or a mixture containing several salts of hesperetin dihydrochalcone (I) or a mixture containing or consisting of hesperetin dihydrochalcone (I) and one or more salts of hesperetin dihydrochalcone (I), the total content of sweet-tasting substances (e.g., in preparations for nutrition or enjoyment) can be advantageously reduced without impairing the overall sweetness. This is important not only for health reasons but also with regard to taste properties. In particular, a sweet-tasting (and, in high concentrations, also bitter) substance such as...Stevioside can advantageously be used in combination with hesperetin dihydrochalcone (I) or a salt of hesperetin dihydrochalcone (I) or a mixture comprising or consisting of several salts of hesperetin dihydrochalcone (I), or a mixture comprising or consisting of hesperetin dihydrochalcone (I) and one or more salts of hesperetin dihydrochalcone (I), in concentrations so low that no or at least only a reduced bitter aftertaste of the both sweet and bitter-tasting substance, such as stevioside, is perceived (while maintaining the sweet taste sensations). Furthermore, the bitter taste sensation (of the both sweet and bitter-tasting substance) can be advantageously masked or at least (further) reduced by a preferred use according to the invention (as described above).

[0087] Several studies with stevia extracts (Yamada A. et al. (1985): Chronic toxicity study of dietary stevia extracts in F344 rats. In: J. Food Hyg. Soc. Japan. Vol. 26, pp. 169-183; Melis, MS (1999): Effects of chronic administration of Stevia rebaudiana on fertility in rats. In: J. Ethnopharmacol. Vol. 67, pp. 157-161) have reported effects on the human reproductive system, such as reduced spermatogenesis, lower seminal vesicle weight, and increased interstitial cell proliferation in the testes. It is also known that the leaves of Stevia rebaudiana were used by Paraguayan Indians in tea as a male contraceptive.

[0088] In addition to the aforementioned benefits, reducing the required amount of stevia extract or steviol glycosides can also lead to cost savings.

[0089] When used in accordance with the disclosure, it may be advantageous if not all unpleasant or bitter taste nuances are (completely) masked, as these may also be desirable under certain circumstances.

[0090] When used as described above, the preparation is preferably intended as an oral drug, cosmetic, for nutritional purposes, as a dietary supplement, for oral care, or for enjoyment. Preparations according to the invention and their preferred embodiments are described further below.

[0091] Therefore, a further object of the present invention was to provide an aroma composition comprising a compound of formula (I) or a salt of the compound of formula (I) or a mixture comprising or consisting of a plurality of salts of the compound of formula (I) or a mixture comprising or consisting of the compound of formula (I) and a salt or a plurality of salts of the compound of formula (I).

[0092] In a particularly preferred embodiment according to the present invention, the aroma composition comprises - two or more different salts of hesperet dihydrochalcone (I) or - Hesperetin dihydrochalcone (I) and one or more different salts of hesperetin dihydrochalcone (I), as described above, wherein the countercation(s) of one, several or all of the salts of hesperetin dihydrochalcone (I) is from the group consisting of Na + , K + NH4+ , Ca 2+ , Mg 2+ , Al 3+ and Zn 2+ selected is or are, especially preferably selected from the group consisting of Na + and K + .

[0093] In a preferred embodiment, the flavor composition according to the present invention comprises a compound of formula (I) or a salt of the compound of formula (I) or a mixture comprising or consisting of a plurality of salts of the compound of formula (I), or a mixture comprising or consisting of the compound of formula (I) and a salt or a plurality of salts of the compound of formula (I), in an amount in the range of 0.001-10%, based on the total weight of the flavor composition, preferably in the range of 0.002-5%, based on the total weight of the flavor composition, more preferably in the range of 0.05-2%, based on the total weight of the flavor composition, and particularly preferably in the range of 0.05-1%, based on the total weight of the flavor composition.

[0094] A further objective of the present invention was to provide an aroma composition with which the sweet taste impression of a sweet-tasting substance is influenced by the intensity of the taste impressions of sweet-tasting and / or unpleasant, in particular bitter-tasting, and / or both sweet and unpleasant, in particular bitter, tasting substances, in particular intensifying the sweet taste impression of a sweet-tasting substance, preferably synergistically intensifying it, and—if the sweet-tasting substance has a bitter pre- and / or aftertaste—preferably additionally masking or reducing the bitter taste impression. It is also preferred that the intensity of an unpleasant (in particular bitter) taste impression of substances or mixtures of substances without a sweet taste is masked or reduced.

[0095] Consequently, according to a further aspect of the present invention, hesperetin dihydrochalcone (I), or a salt of hesperetin dihydrochalcone (I), or a mixture comprising or consisting of several salts of hesperetin dihydrochalcone (I), or a mixture comprising or consisting of hesperetin dihydrochalcone (I) and one or more salts of hesperetin dihydrochalcone (I), is used in a flavor composition to intensify—preferably synergistically—the sweet taste of a sweet-tasting substance and to mask, reduce, or suppress a bitter taste impression of a bitter-tasting substance. Such a flavor composition is advantageously particularly well suited for intensifying—preferably synergistically—a sweet taste and / or for masking or reducing a bitter taste impression of a substance that tastes both sweet and bitter.

[0096] The present invention further relates to an aroma composition comprising or consisting of the following components: (a) a compound of formula (I) or a salt of the compound of formula (I) or a mixture comprising or consisting of a plurality of salts of the compound of formula (I), or a mixture comprising or consisting of the compound of formula (I) and a salt or a plurality of salts of the compound of formula (I); and at least one or more of the substances selected from the group consisting of substance(s) (c) and (d) or mixtures thereof, wherein - Substance(s) (c) means one or more unpleasant-tasting substances, preferably bitter, sour and / or astringent-tasting substances, in particular bitter-tasting substances. - Substance(s) (d) means one or more substances that taste both sweet and unpleasant, especially bitter; and / or (b) one or more sweet-tasting substances; and, where appropriate, includes: (e) one or more substances for masking or reducing an unpleasant taste, in particular a bitter taste, and / or (f) one or more other substances to enhance a sweet taste sensation and / or (g) one or more substances for masking or reducing a metallic, chalky, acidic or astringent taste, and / or (h) one or more substances with a taste sensation selected from the group consisting of cooling, umami, fruity and savory taste sensations or mixtures thereof; wherein components (b)-(h) do not include hesperet dihydrochalkone (I) or a salt of hesperet dihydrochalkone (I).

[0097] The present invention also relates to an aroma composition comprising or consisting of the following components: (a) a compound of formula (I) or a salt of the compound of formula (I) or a mixture comprising or consisting of a plurality of salts of the compound of formula (I) or a mixture comprising or consisting of the compound of formula (I) and a salt or a plurality of salts of the compound of formula (I); and at least one or more of the substances selected from the group consisting of substance(s) (c) and (d) or mixtures thereof, wherein - Substance(s) (c) means one or more unpleasant-tasting substances, preferably bitter, sour and / or astringent-tasting substances, in particular bitter-tasting substances. - Substance(s) (d) means one or more substances that taste both sweet and unpleasant, especially bitter; and / or (b) one or more sweet-tasting substances; and, where appropriate, includes: (e) one or more substances for masking or reducing an unpleasant taste, in particular a bitter taste, and / or (f) one or more other substances to enhance a sweet taste sensation and / or (g) one or more substances for masking or reducing a metallic, chalky, acidic or astringent taste, and / or (h) one or more substances with a taste sensation selected from the group consisting of cooling, umami, fruity and savory taste sensations or mixtures thereof; wherein components (b)-(h) do not include hesperetindihydrochalcone (I) or a salt of hesperetindihydrochalcone (I). wherein the total amount of component (a) is sufficient to enhance, preferably synergistically, the sweet taste of the sweet-tasting substance, compared to an otherwise equivalent composition without hesperet dihydrochalcone (I) and / or salt(s) thereof, and wherein the total amount of hesperetin dihydrochalcone (I) and / or its salt(s) is sufficient to reduce and / or mask the unpleasant taste of the bitter, sour and / or astringent tasting substance(s).

[0098] The present invention also relates to an aroma composition comprising or consisting of the following components: (a) a compound of formula (I) or a salt of the compound of formula (I) or a mixture comprising or consisting of a plurality of salts of the compound of formula (I) or a mixture comprising or consisting of the compound of formula (I) and a salt or a plurality of salts of the compound of formula (I); and at least one or more of the substances selected from the group consisting of substance(s) (c) and (d) or mixtures thereof, wherein - Substance(s) (c) means one or more unpleasant-tasting substances, preferably bitter, sour and / or astringent-tasting substances, in particular bitter-tasting substances. - Substance(s) (d) means one or more substances that taste both sweet and unpleasant, especially bitter; and / or (b) one or more sweet-tasting substances; and, where appropriate, includes: (e) one or more substances for masking or reducing an unpleasant taste, in particular a bitter taste, and / or (f) one or more further substances to intensify a sweet taste sensation and / or (g) one or more substances for masking or reducing a metallic, chalky, acidic or astringent taste, and / or (h) one or more substances with a taste sensation selected from the group consisting of cooling, umami, fruity and savory taste sensations or mixtures thereof; wherein components (b)-(h) do not include hesperetindihydrochalcone (I) or a salt of hesperetindihydrochalcone (I). wherein the total amount of component (a) is sufficient to enhance - preferably synergistically - the sweet taste of the sweet-tasting substance compared to an otherwise equivalent composition without hesperet dihydrochalcone (I) and / or its salt(s), and wherein the total amount of hesperet dihydrochalcone (I) and / or its salt(s) is sufficient to reduce and / or mask the unpleasant taste of the bitter, sour and / or astringent tasting substance(s), and wherein the total amount of hesperet dihydrochalcone (I) and / or its salt(s) is sufficient to modulate the taste impressions of the components (h).

[0099] Furthermore, the present invention also relates to an aroma composition comprising or consisting of the following components: (a) a compound of formula (I) or a salt of the compound of formula (I) or a mixture comprising or consisting of a plurality of salts of the compound of formula (I) or a mixture comprising or consisting of the compound of formula (I) and a salt or a plurality of salts of the compound of formula (I); and at least one or more of the substances selected from the group consisting of substance(s) (c) and (d) or mixtures thereof, wherein - Substance(s) (c) means one or more unpleasant-tasting substances, preferably bitter, sour and / or astringent-tasting substances, in particular bitter-tasting substances. - Substance(s) (d) means one or more substances that taste both sweet and unpleasant, especially bitter-tasting substances; and (e) one or more substances for masking or reducing an unpleasant, especially bitter, taste sensation; and may include: (b) one or more sweet-tasting substances; and / or (f) one or more further substances for intensifying a sweet taste impression, particularly preferably selected from the group consisting of hesperetin, phloretin, rubusoside, fermented rubus extract according to EP 2,954,785-A1, naringenin, balansin A, balansin B and phyllodulcin, and / or (g) one or more substances for masking or reducing a metallic, chalky, acidic or astringent taste, and / or (h) one or more substances with a taste sensation selected from the group consisting of cooling, umami, fruity and savory taste sensations or mixtures thereof; wherein components (b)-(h) do not contain hesperetindihydrochalcone (I) or a salt of hesperetindihydrochalcone (I).

[0100] A flavor composition that includes or consists of the following components is particularly preferred: (a) a compound of formula (I) or a salt of the compound of formula (I) or a mixture comprising or consisting of a plurality of salts of the compound of formula (I) or a mixture comprising or consisting of the compound of formula (I) and a salt or a plurality of salts of the compound of formula (I); and at least one or more of the substances selected from the group consisting of substance(s) (c) and (d) or mixtures thereof, wherein - Substance(s) (c) means one or more unpleasant-tasting substances, preferably bitter, sour and / or astringent-tasting substances, in particular bitter-tasting substances. - Substance(s) (d) means one or more substances that taste both sweet and unpleasant, especially bitter-tasting substances; and (e) at least one of the substances selected from the group consisting of homoeriodictyol or its sodium salts, eriodictyol, matairesinol, lariciresinol, naringenin, phloretin, 5-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-7-methoxychroman-2-one, 5,7-dihydroxy-4-(4-hydroxyphenyl)-chroman-2-one, 5,7-dihydroxy-4-(4-hydroxy-3-methoxyphenyl)-chroman-2-one and 2,4-dihydroxybenzoic acid vanillylamide and optionally further substances for masking or reducing an unpleasant, in particular bitter, taste impression; and optionally comprising: (b) one or more sweet-tasting substances; and / or (f) one or more further substances to enhance a sweet taste sensation, particularly preferably selected from the group consisting of hesperetin, phloretin, rubusoside, fermented rubus extract according to EP 2,954,785-A1, naringenin, balansin A, balansin B and phyllodulcin, and / or (g) one or more substances for masking or reducing a metallic, chalky, acidic or astringent taste, and / or (h) one or more substances with a taste sensation selected from the group consisting of cooling, umami, fruity and savory taste sensations or mixtures thereof; wherein components (b)-(h) do not contain hesperetindihydrochalcone (I) or a salt of hesperetindihydrochalcone (I).

[0101] Furthermore, a flavor composition comprising or consisting of the following components is particularly preferred: (a) a compound of formula (I) or a salt of the compound of formula (I) or a mixture comprising or consisting of a plurality of salts of the compound of formula (I), or a mixture comprising or consisting of the compound of formula (I) and a salt or a plurality of salts of the compound of formula (I); and at least one or a plurality of the substances selected from the group consisting of substance(s) (c) and (d) or mixtures thereof, wherein - Substance(s) (c) means one or more unpleasant-tasting substances, preferably bitter, sour and / or astringent-tasting substances, in particular bitter-tasting substances. - Substance(s) (d) means one or more substances that taste both sweet and unpleasant, especially bitter-tasting substances; and (e) Homoeriodictyol or its sodium salts and optionally at least one of the substances selected from the group consisting of eriodictyol, matairesinol, lariciresinol, naringenin, phloretin, 5-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-7-methoxychroman-2-one, 5,7-dihydroxy-4-(4-hydroxyphenyl)-chroman-2-one, 5,7-dihydroxy-4-(4-hydroxy-3-methoxyphenyl)-chroman-2-one or 2,4-dihydroxybenzoic acid vanillylamide and optionally further substances for masking or reducing an unpleasant taste sensation, in particular a bitter taste sensation; and optionally comprising: (b) one or more sweet-tasting substances; and / or (f) one or more further substances to enhance a sweet taste sensation, particularly preferably selected from the group consisting of hesperetin, phloretin, rubusoside, fermented rubus extract according to EP 2,954,785-A1, naringenin, balansin A, balansin B and phyllodulcin, and / or (g) one or more substances for masking or reducing a metallic, chalky, acidic or astringent taste, and / or (h) one or more substances with a taste sensation selected from the group consisting of cooling, umami, fruity and savory taste sensations or mixtures thereof; wherein components (b)-(h) do not contain hesperet dihydrochalkone (I) or a salt of hesperet dihydrochalkone (I).

[0102] Consequently, this invention also relates to an aroma composition comprising or consisting of the following components: (a) a compound of formula (I) or a salt of the compound of formula (I) or a mixture comprising or consisting of a plurality of salts of the compound of formula (I), or a mixture comprising or consisting of the compound of formula (I) and a salt or a plurality of salts of the compound of formula (I); and at least one or a plurality of substances selected from the group consisting of substance(s) (c) and (d) or mixtures thereof, wherein - Substance(s) (c) means one or more unpleasant-tasting substances, preferably bitter, sour and / or astringent-tasting substances, in particular bitter-tasting substances. - Substance(s) (d) means one or more substances that taste both sweet and unpleasant, especially bitter; and / or (b) one or more sweet-tasting substances; and, where appropriate, includes: (e) one or more substances for masking or reducing an unpleasant taste, in particular a bitter taste, and / or (f) one or more further substances to enhance a sweet taste sensation, particularly preferably selected from the group consisting of hesperetin, phloretin, rubusoside, fermented rubus extract according to EP 2,954,785-A1, naringenin, balansin A, balansin B and phyllodulcin, and / or (g) one or more substances for masking or reducing a metallic, chalky, acidic or astringent taste, and / or (h) one or more substances with a taste sensation selected from the group consisting of cooling, umami, fruity and savory taste sensations or mixtures thereof; wherein components (b)-(h) do not include hesperet dihydrochalcone (I) or a salt of hesperet dihydrochalcone (I) and, wherein the total amount of component (a) is sufficient to enhance - preferably synergistically - the sweet taste of the sweet-tasting substance compared to an otherwise equivalent composition without hesperet dihydrochalcone (I) and / or its salt(s), and wherein the total amount of hesperet dihydrochalcone (I) and / or its salt(s) is sufficient to reduce and / or mask the unpleasant taste of the bitter, sour and / or astringent tasting substance(s), and wherein the total amount of hesperet dihydrochalcone (I) and / or its salt(s) is sufficient to modulate the taste impressions of the components (h).

[0103] Therefore, the present invention also relates to an aroma composition comprising or consisting of the following components: (a) a compound of formula (I) or a salt of the compound of formula (I) or a mixture comprising or consisting of a plurality of salts of the compound of formula (I), or a mixture comprising or consisting of the compound of formula (I) and a salt or a plurality of salts of the compound of formula (I); and at least one or a plurality of substances selected from the group consisting of substance(s) (c) and (d) or mixtures thereof, wherein - Substance(s) (c) means one or more unpleasant-tasting substances, preferably bitter, sour and / or astringent-tasting substances, in particular bitter-tasting substances. - Substance(s) (d) means one or more substances that taste both sweet and unpleasant, especially bitter; and (b) one or more sweet-tasting substances; and further includes: (e) one or more substances for masking or reducing an unpleasant taste, in particular a bitter taste, and / or (f) one or more further substances to enhance a sweet taste sensation, particularly preferably selected from the group consisting of hesperetin, phloretin, rubusoside, fermented rubus extract according to EP 2,954,785-A1, naringenin, balansin A, balansin B and phyllodulcin, and (g) one or more substances for masking or reducing a metallic, chalky, acidic or astringent taste, and (h) one or more substances with a taste sensation selected from the group consisting of cooling, umami, fruity and savory taste sensations or mixtures thereof; wherein components (b)-(h) do not include hesperet dihydrochalcone (I) or a salt of hesperet dihydrochalcone (I) and, wherein the total amount of component (a) is sufficient to enhance - preferably synergistically - the sweet taste of the sweet-tasting substance compared to an otherwise equivalent composition without hesperet dihydrochalcone (I) and / or its salt(s), and wherein the total amount of hesperet dihydrochalcone (I) and / or its salt(s) is sufficient to reduce and / or mask the unpleasant taste of the bitter, sour and / or astringent tasting substance(s), and wherein the total amount of hesperet dihydrochalcone (I) and / or its salt(s) is sufficient to modulate the taste impressions of the components (h).

[0104] Furthermore, the present invention also relates to an aroma composition comprising or consisting of the following components: (a) a compound of formula (I) or a salt of the compound of formula (I) or a mixture comprising or consisting of a plurality of salts of the compound of formula (I), or a mixture comprising or consisting of the compound of formula (I) and a salt or a plurality of salts of the compound of formula (I); and at least one or a plurality of the substances selected from the group consisting of substance(s) (c) and (d) or mixtures thereof, wherein - Substance(s) (c) means one or more unpleasant-tasting substances, preferably bitter, sour and / or astringent-tasting substances, in particular bitter-tasting substances. - Substance(s) (d) means one or more substances that taste both sweet and unpleasant, especially bitter-tasting substances; and (e) one or more substances for masking or reducing an unpleasant, especially bitter, taste sensation; and may include: (b) one or more sweet-tasting substances; and / or (f) one or more further substances for intensifying a sweet taste impression, particularly preferably selected from the group consisting of hesperetin, phloretin, rubusoside, fermented rubus extract according to EP 2,954,785-A1, naringenin, balansin A, balansin B and phyllodulcin, and / or (g) one or more substances for masking or reducing a metallic, chalky, acidic or astringent taste, and / or (h) one or more substances with a taste sensation selected from the group consisting of cooling, umami, fruity and savory taste sensations or mixtures thereof; wherein components (b)-(h) do not contain hesperet dihydrochalcone (I) or a salt of hesperet dihydrochalcone (I) and, wherein the total amount of component (a) is sufficient to enhance - preferably synergistically - the sweet taste of the sweet-tasting substance compared to an otherwise equivalent composition without hesperet dihydrochalcone (I) and / or its salt(s), and wherein the total amount of hesperet dihydrochalcone (I) and / or its salt(s) is sufficient to reduce and / or mask the unpleasant taste of the bitter, sour and / or astringent tasting substance(s), and wherein the total amount of hesperet dihydrochalcone (I) and / or its salt(s) is sufficient to modulate the taste impressions of the components (h).

[0105] A flavor composition that includes or consists of the following components is particularly preferred: (a) a compound of formula (I) or a salt of the compound of formula (I) or a mixture comprising or consisting of a plurality of salts of the compound of formula (I), or a mixture comprising or consisting of the compound of formula (I) and a salt or a plurality of salts of the compound of formula (I); and at least one or a plurality of substances selected from the group consisting of substance(s) (c) and (d) or mixtures thereof, wherein - Substance(s) (c) means one or more unpleasant-tasting substances, preferably bitter, sour and / or astringent-tasting substances, in particular bitter-tasting substances. - Substance(s) (d) means one or more substances that taste both sweet and unpleasant, especially bitter-tasting substances; and (e) at least one of the substances selected from the group consisting of homoeriodictyol or its sodium salts, eriodictyol, matairesinol, lariciresinol, naringenin, phloretin, 5-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-7-methoxychroman-2-one, 5,7-dihydroxy-4-(4-hydroxyphenyl)-chroman-2-one, 5,7-dihydroxy-4-(4-hydroxy-3-methoxyphenyl)-chroman-2-one and 2,4-dihydroxybenzoic acid vanillylamide and optionally further substances for masking or reducing an unpleasant, in particular bitter, taste impression; and optionally comprising: (b) one or more sweet-tasting substances; and / or (f) one or more further substances to enhance a sweet taste sensation, particularly preferably selected from the group consisting of hesperetin, phloretin, rubusoside, fermented rubus extract according to EP 2,954,785-A1, naringenin, balansin A, balansin B and phyllodulcin, and / or (g) one or more substances for masking or reducing a metallic, chalky, acidic or astringent taste, and / or (h) one or more substances with a taste sensation selected from the group consisting of cooling, umami, fruity and savory taste sensations or mixtures thereof; wherein components (b)-(h) do not include hesperet dihydrochalcone (I) or a salt of hesperet dihydrochalcone (I) and, wherein the total amount of component (a) is sufficient to enhance - preferably synergistically - the sweet taste of the sweet-tasting substance compared to an otherwise equivalent composition without hesperet dihydrochalcone (I) and / or its salt(s), and wherein the total amount of hesperet dihydrochalcone (I) and / or its salt(s) is sufficient to reduce and / or mask the unpleasant taste of the bitter, sour and / or astringent tasting substance(s), and wherein the total amount of hesperet dihydrochalcone (I) and / or its salt(s) is sufficient to modulate the taste impressions of the components (h).

[0106] Furthermore, a flavor composition comprising or consisting of the following components is particularly preferred: (a) a compound of formula (I) or a salt of the compound of formula (I) or a mixture comprising or consisting of a plurality of salts of the compound of formula (I), or a mixture comprising or consisting of the compound of formula (I) and a salt or a plurality of salts of the compound of formula (I); and at least one or a plurality of substances selected from the group consisting of substance(s) (c) and (d) or mixtures thereof, wherein - Substance(s) (c) means one or more unpleasant-tasting substances, preferably bitter, sour and / or astringent-tasting substances, in particular bitter-tasting substances. - Substance(s) (d) means one or more substances that taste both sweet and unpleasant, especially bitter-tasting substances; and (e) Homoeriodictyol or its sodium salts and optionally at least one of the substances selected from the group consisting of eriodictyol, matairesinol, lariciresinol, naringenin, phloretin, 5-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-7-methoxychroman-2-one, 5,7-dihydroxy-4-(4-hydroxyphenyl)-chroman-2-one, 5,7-dihydroxy-4-(4-hydroxy-3-methoxyphenyl)-chroman-2-one or 2,4-dihydroxybenzoic acid vanillylamide and optionally further substances for masking or reducing an unpleasant taste sensation, in particular a bitter taste sensation; and optionally comprising: (b) one or more sweet-tasting substances; and / or (f) one or more further substances to enhance a sweet taste sensation, particularly preferably selected from the group consisting of hesperetin, phloretin, rubusoside, fermented rubus extract according to EP 2,954,785-A1, naringenin, balansin A, balansin B and phyllodulcin, and / or (g) one or more substances for masking or reducing a metallic, chalky, acidic or astringent taste, and / or (h) one or more substances with a taste sensation selected from the group consisting of cooling, umami, fruity and savory taste sensations or mixtures thereof; wherein components (b)-(h) do not include hesperet dihydrochalcone (I) or a salt of hesperet dihydrochalcone (I) and, wherein the total amount of component (a) is sufficient to enhance - preferably synergistically - the sweet taste of the sweet-tasting substance compared to an otherwise equivalent composition without hesperet dihydrochalcone (I) and / or its salt(s), and wherein the total amount of hesperet dihydrochalcone (I) and / or its salt(s) is sufficient to reduce and / or mask the unpleasant taste of the bitter, sour and / or astringent tasting substance(s), and wherein the total amount of hesperet dihydrochalcone (I) and / or its salt(s) is sufficient to modulate the taste impressions of the components (h).

[0107] One or the sweet-tasting substance(s) (b) is / are preferably selected from the group consisting of vanillin, ethyl vanillin, ethyl vanillin isobutyrate (=3-ethoxy-4-isobutyryloxybenzaldehyde), furaneol ®(2,5-Dimethyl-4-hydroxy-3(2H)-furanon) und Derivaten davon (z.z. B. Homofuranol, 2-Ethyl-4-hydroxy-5-methyl-3(2H)-furanon), Homofuronol (2-Ethyl-5-methyl-4-hydroxy-3(2H)-furanon und 5-Ethyl-2-methyl-4-hydroxy-3(2H)-furanon), Maltol und dessen Derivate (z.z. B. Ethylmaltol), Cumarin und seine Derivate, gamma-Lactone (z. B. gamma-Undecalacton, gamma-Nonalacton), delta-Lactone (z. B. 4-Methyl-delta-lacton, Massoilacton, Delta-decalacton, Tuberolacton), Methylsorbat, Divanillin, 4-Hydroxy-2(oder 5)-ethyl-5(oder 2)-methyl-3(2H)furanon, 2-Hydroxy-3-methyl-2-cyclopentenone, 3-Hydroxy-4,5-dimethyl-2(5H)-furanon, Fruchtester und Fruchtlactone (z.g.n-Butylacetat, Isoamylacetat, Ethylpropionat, Ethylbutyrat, n-Butylbutyrat, Isoamylbutyrat, Ethyl-3-methylbutyrat, Ethyl-n-hexanoat, Allyl-n-hexanoat, n-Butyl-n-hexanoat, Ethyl-n-octanoat, Ethyl-3-methyl-3-phenylglycidat, Ethyl-2-trans-4-cis-decadienoat), 4-(p-Hydroxyphenyl)-2-butanon, 1,1-Dimethoxy-2,2,5-trimethyl-4-hexan, 2,6-Dimethyl-5-hepten-1-al, Phenylacetaldehyd, Saccharose, Trehalose, Lactose, Maltose, Melizitose, Raffinose, Palatinose, Lactulose, D-Fructose, D-Glucose, D-Galactose, L-Rhamnose, D-Sorbose, D-Mannose, D-Tagatose, D-Arabinose, L-Arabinose, D-Ribose, D-Glyceraldehyd, Erythrit, Threitol, Arabit, Ribit, Xylit, Sorbit, Mannit, Dulcit und Lactit.

[0108] One or the unpleasant, especially bitter, tasting substance(s) (c) is / are preferably selected from the group consisting of xanthine alkaloids, xanthines (caffeine, theobromine, theophylline), alkaloids (quinine, quinine hydrochloride, brucine, strychnine, nicotine), phenolic glycosides (e.g., salicin, arbutin), flavonoid glycosides (e.g., hesperidin, naringin), chalcones or chalcone glycosides, hydrolyzable tannins (gallic or ellagic acid esters of carbohydrates, e.g., pentagalloylglucose), non-hydrolyzable tannins (possibly galloylated catechins or epicatechins and their oligomers, e.g., proanthyocyanidins or procyanidins, thearubigin), flavones (e.g., quercertin, taxifolin, myricetin), other Polyphenols (gamma-oryzanol, caffeic acid or their esters), terpenoid bitter substances (e.g.Limonoids such as limonin or nomilin from citrus fruits, lupolone and humulone from hops, iridoids, secoiridoids), absinthin from wormwood, amarogentin from gentian, metal salts (potassium chloride, sodium sulfate, magnesium salts, iron salts, aluminum salts, zinc salts), pharmaceutical agents (e.g., fluoroquinolone antibiotics, beta-lactam antibiotics, ambroxol, propylthiouracil [PROP], aspirin (acetylsalicylic acid), salicin, paracetamol (acetaminophen), ibuprofen, naproxen, ambroxol, guafenesin, omeprazole, pantoprazole, dextromorphan, or quinine), vitamins (e.g., vitamin H, B vitamins such as vitamins B1, B2, B6, B12, niacin, pantothenic acid), denatonium benzoate, or others Denatonium salts, sucralose octaacetate, urea, unsaturated fatty acids, especially unsaturated fatty acids in emulsions, amino acids (e.g.Leucine, isoleucine, valine, tryptophan, proline, histidine, tyrosine, lysine or phenylalanine, in particular the respective L-enantiomers of leucine, isoleucine, valine, tryptophan, proline, histidine, tyrosine, lysine or phenylalanine), peptides (in particular peptides with an amino acid from the group L-leucine, L-isoleucine, L-valine, L-tryptophan, L-proline or L-phenylalanine at the N- or C-terminus).

[0109] One or the substance(s) (d) that tastes both sweet and unpleasant is / are preferably selected from the group consisting of steviol glycosides (in particular stevioside and rebaudioside A), rubusoside, dulcoside, mogroside, phyllodulcin, glycyrrhetinic acid or extracts of Stevia ssp. (in particular Stevia rebaudiana), Luo Han Guo, Rubus suavissimus, Hydrangea dulcis, Mycetia balansae, Glycyrrhyza glabra, A or the substance(s) (e) for masking or reducing a bitter taste impression is / are preferably selected from the group consisting of sodium salts (e.g.Sodium chloride, sodium lactate, sodium citrate, sodium acetate, sodium gluconoate), homoeriodictyol or its sodium salts, eriodictyol, matairesinol, lariciresinol, naringenin, phloretin, 5-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-7-methoxychroman-2-one, 5,7-dihydroxy-4-(4-hydroxyphenyl)chroman-2-one, 5,7-dihydroxy-4-(4-hydroxy-3-methoxyphenyl)chroman-2-one, or 2,4-dihydroxybenzoic acid vanillylamide, gamma-aminobutyric acid, pellitorin (particularly as described in EP 2008530 A1) and gingerdione, preferably selected from the group consisting of sodium salts (e.g. sodium chloride, sodium chloride, sodium chloride, sodium chloride, sodium chloride, sodium chloride, sodium chloride, sodium chloride, sodium chloride, sodium chloride, sodium chloride). B. sodium chloride, sodium lactate, sodium citrate, sodium acetate, sodium gluconoate).

[0110] One or the substance(s) (f) for enhancing a sweet taste impression is / are preferably selected from the group consisting of hesperetin (in particular as disclosed in WO 2007 / 014879), hydroxyphenylalkanedions (in particular as described in WO 2007 / 003527), deoxybenzoes (in particular as described in WO 2006 / 106023 and German patent application DE10 2009 002 268.6), 4-hydroxychalcones (in particular as described in WO 2007 / 107596), propenylphenyl glycosides (chavicol glycosides) (in particular as described in EP 1 955 601 A1), divanillins (in particular as described in WO 2004 / 078302), hydroxyflavanes according to EP 2,253,226, dihydrochalcones according to EP 2,353,403 B1, Naringin, Phloretin, Rubusoside, fermented Rubus extract according to EP 2,954,785-A1, Naringenin, Balansin A, Balansin B and Phyllodulcin.

[0111] The aforementioned documents are incorporated by reference into this application with regard to the relevant connections disclosed therein.

[0112] An aroma composition according to the invention preferably contains at least one or more further substance(s) (g) for masking or reducing a metallic, chalky, sour, or astringent taste impression and / or one or more further substance(s) (h) for intensifying a salty or umami taste impression. Preferred further substances for masking or reducing an unpleasant taste impression and / or for intensifying a pleasant taste impression are described below.

[0113] Particularly preferred is an aroma composition (as described above) wherein the bitter-tasting substance (c) or the sweet- and bitter-tasting substance (d) is selected from the group consisting of steviol glycosides, in particular stevioside and rebaudiosides, preferably selected from the group consisting of rebaudioside A, rubusoside, dulcoside, mogroside, phyllodulcin, glycyrrhetinic acid or extracts of Stevia ssp. (in particular Stevia rebaudiana), Luo Han Guo, Rubus suavissimus, Mycetia balansae, Hydrangea dulcis or Glycyrrhyza glabra.

[0114] In particular, a use of an aroma composition according to the invention (as described above) for intensifying – preferably synergistically intensifying – the sweet taste of a sweet-tasting substance or mixture of substances (b) and for masking or reducing an unpleasant, preferably bitter, sour and / or astringent, especially bitter taste impression of an unpleasant, especially bitter, tasting substance or mixture of substances (c) and / or for intensifying – preferably synergistically – the sweet taste impressions and / or for reducing or masking the unpleasant, especially bitter, taste impressions of the both sweet and unpleasant, especially bitter, tasting substance or mixture of substances (d) in a preparation intended as an oral medicinal product, as a cosmetic, for nutrition, as a food supplement, for oral care or for enjoyment is disclosed.especially in preparations according to the invention, as described below. A flavor composition according to the invention is particularly preferred for improving the sensory profile of confectionery intended for oral consumption.

[0115] Consequently, the present invention also relates to a preparation containing an aroma composition according to the invention as described above. The preparation according to the invention is preferably a preparation selected from the group consisting of preparations for nutrition, as food supplements, for oral care or enjoyment, cosmetic preparations, in particular for use in the head area, pharmaceutical preparations for oral administration, aroma mixtures for use in one of the aforementioned preparations, or semi-finished products for the manufacture of one of the aforementioned preparations.

[0116] The person skilled in the art will understand that the individual components of the aroma composition according to the invention must be present in the preparation according to the invention. According to the invention, it is irrelevant whether these components are introduced into the preparation together or one after the other.

[0117] A preparation for nutritional purposes, as a food supplement, for oral care or enjoyment, as a cosmetic or as an orally administered medicinal product (as described above) is particularly preferred according to the invention, wherein the preparation contains, based on the total weight of the preparation, 0.00001 wt.% (0.1 ppm) - 0.005 wt.% (50 ppm), preferably 0.00005 wt.% (0.5 ppm) - 0.003 wt.% (30 ppm) and particularly preferably 0.0001 wt.% (1 ppm) - 0.001 wt.% (10 ppm) of hesperet dihydrochalcone (I) and its salts.

[0118] The preparations according to the invention can also be in the form of semi-finished products, in particular for the manufacture of a preparation for nutrition, as a food supplement, for oral care or enjoyment, as a cosmetic or as a medicinal product for oral administration or as an aroma mixture.

[0119] Particularly preferred is a preparation according to the invention (as described above), wherein the preparation is a semi-finished product suitable for the production of a preparation intended for use in nutrition, as a food supplement, as a flavoring mixture, for oral care or enjoyment, or as a cosmetic preparation or as a medicinal product for oral administration, in particular for use in nutrition and as a flavoring mixture.

[0120] Particularly preferred is a semi-finished product or a flavoring mixture (as described above), wherein the semi-finished product contains, based on the total weight of the semi-finished product or flavoring mixture, 0.0001 wt.% to 95 wt.%, in particular 0.001 wt.% to 95 wt.%, preferably 0.001 wt.% to 80 wt.%, particularly preferably 0.01 wt.% to 50 wt.%, of the hesperetin dihydrochalcone (I) and its salts.

[0121] Preparations for nutrition or enjoyment within the meaning of the present invention include, for example, baked goods (e.g., bread, pastries, cakes, other confectionery products), sweets (e.g., pralines, chocolate bar products, other bar products, fruit gums, hard and soft caramels, chewing gum), alcoholic or non-alcoholic beverages (e.g., coffee, tea, wine, wine-based beverages, beer, beer-based beverages, liqueurs, spirits, brandy, fruit-based beverages, isotonic beverages, soft drinks, nectars, fruit and vegetable juices, fruit or vegetable juice preparations), instant beverages (e.g., instant cocoa beverages, instant tea beverages, instant coffee beverages), meat products (e.g., ham, fresh or cured sausage preparations, seasoned or marinated fresh or cured Meat products), eggs or egg products (dried egg, egg white, egg yolk), cereal products (e.g.Breakfast cereals, muesli bars, pre-cooked ready-to-eat rice products), dairy products (e.g., milk drinks, ice cream, yogurt, kefir, quark, soft cheese, hard cheese, dried milk powder, whey, butter, buttermilk, partially or fully hydrolyzed milk protein products), products made from soy protein or other soybean fractions (e.g., soy milk and products made from it, preparations containing soy lecithin, fermented products such as tofu or tempeh or products made from them, soy sauce), fruit preparations (e.g., jams, fruit ice cream, fruit sauces, fruit fillings), vegetable preparations (e.g., ketchup, sauces, dried vegetables, frozen vegetables, pre-cooked vegetables, canned vegetables, preserved vegetables), snack items (e.g., baked or fried potato chips or potato dough products, bread dough products, extrudates made from corn or peanuts), Products based on fat or oil, or their emulsions (e.g.Mayonnaise, remoulade, dressings, flavorings), other ready-made meals and soups (e.g., dry soups, instant soups, ready-made soups), spices, spice mixtures, and especially powdered seasonings used, for example, in snack food applications. The preparations according to the invention can also be used as semi-finished products for the manufacture of further preparations that serve nutritional or recreational purposes. The preparations according to the invention can also be food supplements in the form of capsules, tablets (dragees and coated tablets, e.g., with enteric coatings), coated tablets, granules, pellets, solid mixtures, dispersions in liquid phases, as emulsions, as powders, as solutions, as pastes, or as other swallowable or chewable preparations.

[0122] Pharmaceutical preparations for oral consumption within the meaning of the invention are preparations in the form of, for example, capsules, tablets (dragees and coated tablets, e.g., with gastro-resistant coatings), coated tablets, granules, pellets, mixtures of solids, dispersions in liquid phases, as emulsions, as powders, as solutions, as pastes, or as other swallowable or chewable preparations, and are used as prescription, pharmacy-only, or other medicinal products or as food supplements.

[0123] Oral care preparations within the meaning of the present invention include, in particular, oral and / or dental care products such as toothpastes, dental gels, dental powders, mouthwashes, chewing gums, and other oral care products. Oral care preparations containing an extract or components of an extract of Stevie spp. are particularly preferred. Hesperetin dihydrochalcone (I) is advantageously particularly well suited to masking or reducing the bitter taste of steviol glycosides, especially stevioside and / or rebaudioside A, in oral care preparations containing steviol glycosides.

[0124] Cosmetic preparations, particularly cosmetic preparations for use in the head area, are, within the scope of the present invention, preferably cosmetic preparations containing at least one unpleasant-tasting substance, preferably bitter, sour, and / or astringent, in particular a bitter-tasting substance (c), which can also come into contact with the oral cavity when properly applied to the skin. Such preparations include, for example, cosmetic preparations for use in the head area, such as soaps, other cleansing or care products for the face, face creams, lotions, or ointments, sunscreens, beard cleansing or care products, shaving foams, soaps, or gels, lipsticks, or other cosmetics for the lips or lip care products.

[0125] Particularly preferably, the present invention relates to a preparation according to the invention (as described above) which contains as an ingredient one or more substances (d) that taste both sweet and bitter, wherein the total amount of hesperetin dihydrochalcone (I) or salts of hesperetin dihydrochalcone (I) in the preparation is sufficient to both enhance the sweet taste impression of the substance(s) (d) that taste both sweet and bitter - preferably synergistically - and to mask or reduce the bitter taste impression of the substance(s) (d) that tastes both sweet and bitter.

[0126] Particularly preferred is a preparation according to the invention (as described above), in particular a preparation serving nutrition, enjoyment or oral care, in which one, several or preferably all of the both sweet and bitter tasting substance(s) (d) is / are selected from the group of steviol glycosides, in particular from stevioside and rebaudioside A, preferably selected from the group consisting of rebaudioside A, rubusoside, dulcoside, mogroside, phyllodulcin, glycyrrhetinic acid or extracts of Stevia ssp. (in particular Stevia rebaudiana), Luo Han Guo, Rubus suavissimus, Hydrangea dulcis, Mycetia balansae or Glycyrrhyza glabra.

[0127] A further preferred preparation according to the invention (as described above) is one in which the total amount of bitter-tasting substances (c) and / or both sweet and bitter-tasting substances (d) in the preparation is sufficient to be perceived as a bitter taste, and the total amount of (i) hesperet dihydrochalcone (I) and (ii) its salts (component (a)) in the preparation is sufficient to mask the bitter taste of the bitter-tasting substance(s) (c) or the both sweet and bitter-tasting substance(s) (d), compared with a preparation which, with otherwise identical composition, contains neither (i) hesperet dihydrochalcone (I) nor (ii) its salts.

[0128] A preparation according to the invention preferably also contains at least one further substance for masking or reducing a bitter, metallic, chalky, sour or astringent taste impression and / or for intensifying a sweet, salty or umami taste impression.

[0129] A preparation according to the invention is also preferred, in particular a preparation or a semi-finished product (as described above) that serves for nutrition, oral care or enjoyment or cosmetics or is intended for the oral administration of medicinal products, comprising an aroma composition according to the invention (as described above), wherein the aroma composition according to the invention constitutes a proportion of 0.000001 wt.% to 95 wt.% of the total weight of the preparation according to the invention.

[0130] The production of aroma compositions or preparations according to the invention comprises the following steps: (1) Provide the following components: (a) Hesperet dihydrochalcone (I) or a salt of hesperet dihydrochalcone (I) or a mixture comprising or consisting of a plurality of salts of hesperet dihydrochalcone (I), or a mixture comprising or consisting of hesperet dihydrochalcone (I) and a salt or a plurality of salts of hesperet dihydrochalcone (I), and at least one or more of the substances selected from the group consisting of substance(s) (c) and (d) or mixtures thereof, wherein - Substance(s) (c) means one or more unpleasant-tasting substances, preferably bitter, sour and / or astringent-tasting substances, in particular bitter-tasting substances. - Substance(s) (d) means one or more substances that taste both sweet and unpleasant, especially bitter; and / or (b) one or more sweet-tasting substances and / or (e) one or more substances for masking or reducing an unpleasant taste, in particular a bitter taste, and / or (f) one or more other substances to enhance a sweet taste sensation and / or (g) one or more substances for masking or reducing a metallic, chalky, acidic or astringent taste, and / or (h) one or more substances with a taste sensation selected from the group consisting of cooling, umami, fruity and savory taste sensations or mixtures thereof; wherein components (b)-(h) do not include hesperet dihydrochalcone (I) or a salt of hesperet dihydrochalcone (I) and, (2) Mixing components (a), (b), (c) and / or (d) with the other components.

[0131] The production of aroma compositions or preparations according to the invention comprises the following steps: (1) Provide the following components: (a) Hesperet dihydrochalcone (I) or a salt of hesperet dihydrochalcone (I) or a mixture comprising or consisting of several salts of hesperet dihydrochalcone (I) or a mixture comprising or consisting of hesperet dihydrochalcone (I) and a salt or several salts of hesperet dihydrochalcone (I), and at least one or more of the substances selected from the group consisting of substances (c) and (d) or mixtures thereof, wherein - Substance(s) (c) means one or more unpleasant-tasting substances, preferably bitter, sour and / or astringent-tasting substances, in particular bitter-tasting substances. - Substance(s) (d) means one or more substances that taste both sweet and unpleasant, especially bitter-tasting substances; and (e) one or more substances for masking or reducing an unpleasant, especially bitter, taste sensation; and / or (b) one or more sweet-tasting substances, and / or (f) one or more further substances to enhance a sweet taste sensation, particularly preferably selected from the group consisting of hesperetin, phloretin, rubusoside, fermented rubus extract according to EP 2,954,785-A1, naringenin, balansin A, balansin B and phyllodulcin, and / or (g) one or more substances for masking or reducing a metallic, chalky, acidic or astringent taste, and / or (h) one or more substances with a taste sensation selected from the group consisting of cooling, umami, fruity and savory taste sensations or mixtures thereof; wherein components (b)-(h) do not include hesperet dihydrochalcone (I) or a salt of hesperet dihydrochalcone (I) and, (2) Mixing components (a), (b), (c), (e) and / or (d) with the other components.

[0132] The production of aroma compositions or preparations according to the invention comprises the following steps: (1) Provide the following components: (a) Hesperetin dihydrochalcone (I) or a salt of hesperetin dihydrochalcone (I) or a mixture comprising or consisting of a plurality of salts of hesperetin dihydrochalcone (I), or a mixture comprising or consisting of hesperetin dihydrochalcone (I) and a salt or a plurality of salts of hesperetin dihydrochalcone (I), and at least one or more of the substances selected from the group consisting of substances (c) and (d) or mixtures thereof, wherein - Substance(s) (c) means one or more unpleasant-tasting substances, preferably bitter, sour and / or astringent-tasting substances, in particular bitter-tasting substances. - Substance(s) (d) means one or more substances that taste both sweet and unpleasant, especially bitter-tasting substances; and (e) at least one of the substances selected from the group consisting of homoeriodictyol or its sodium salts, eriodictyol, matairesinol, lariciresinol, naringenin, phloretin, 5-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-7-methoxychroman-2-one, 5,7-dihydroxy-4-(4-hydroxyphenyl)-chroman-2-one, 5,7-dihydroxy-4-(4-hydroxy-3-methoxyphenyl)-chroman-2-one and 2,4-dihydroxybenzoic acid vanillylamide, and optionally other substances to mask or reduce an unpleasant, in particular bitter, taste; and / or (b) one or more sweet-tasting substances, and / or (f) one or more further substances to enhance a sweet taste sensation, particularly preferably selected from the group consisting of hesperetin, phloretin, rubusoside, fermented rubus extract according to EP 2,954,785-A1, naringenin, balansin A, balansin B and phyllodulcin, and / or (g) one or more substances for masking or reducing a metallic, chalky, acidic or astringent taste, and / or (h) one or more substances with a taste sensation selected from the group consisting of cooling, umami, fruity and savory taste sensations or mixtures thereof; wherein components (b)-(h) do not include hesperet dihydrochalcone (I) or a salt of hesperet dihydrochalcone (I) and, (2) Mixing components (a), (b), (c), (e) and / or (d) with the other components.

[0133] The production of aroma compositions or preparations according to the invention comprises the following steps: (1) Provide the following components: (a) Hesperetin dihydrochalcone (I) or a salt of hesperetin dihydrochalcone (I) or a mixture comprising or consisting of several salts of hesperetin dihydrochalcone (I) or a mixture comprising or consisting of hesperetin dihydrochalcone (I) and a salt or several salts of hesperetin dihydrochalcone (I), and at least one or more of the substances selected from the group consisting of substance(s) (c) and (d) or mixtures thereof, wherein - Substance(s) (c) means one or more unpleasant-tasting substances, preferably bitter, sour and / or astringent-tasting substances, in particular bitter-tasting substances. - Substance(s) (d) means one or more substances that taste both sweet and unpleasant, especially bitter, and (e) Homoeriodictyol or its sodium salts and optionally at least one of the substances selected from the group consisting of eriodictyol, matairesinol, lariciresinol, naringenin, phloretin, 5-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-7-methoxychroman-2-one, 5,7-dihydroxy-4-(4-hydroxyphenyl)-chroman-2-one, 5,7-dihydroxy-4-(4-hydroxy-3-methoxyphenyl)-chroman-2-one or 2,4-dihydroxybenzoic acid vanillylamide and optionally further substances for masking or reducing an unpleasant, in particular bitter, taste; and / or (b) one or more sweet-tasting substances, and / or (f) one or more further substances to enhance a sweet taste sensation, particularly preferably selected from the group consisting of hesperetin, phloretin, rubusoside, fermented rubus extract according to EP 2,954,785-A1, naringenin, balansin A, balansin B and phyllodulcin, and / or (g) one or more substances for masking or reducing a metallic, chalky, acidic or astringent taste, and / or (h) one or more substances with a taste sensation selected from the group consisting of cooling, umami, fruity and savory taste sensations or mixtures thereof; wherein components (b)-(h) do not include hesperet dihydrochalcone (I) or a salt of hesperet dihydrochalcone (I) and, (2) Mixing components (a), (b), (c), (e) and / or (d) with the other components.

[0134] The preparations according to the invention, containing hesperetin dihydrochalcone (I) and / or its salts, are preferably produced by incorporating hesperetin dihydrochalcone (I) and / or the salt(s) of hesperetin dihydrochalcone (I) with a solid or liquid excipient in the form of a solution or mixture into a suitable preparation, i.e., in particular, a food supplement, a dietary supplement, an oral care product, a cosmetic product, or a pharmaceutical (base) preparation intended for oral administration. These preparations according to the invention can also advantageously be converted into a solid preparation by spray drying.

[0135] To produce the preparations according to the invention, the hesperetin dihydrochalcone (I) and / or its salts and optionally further components of the preparation according to the invention can first (i.e. before being incorporated into the preparation) be incorporated into emulsions, in liposomes, e.g. in emulsions, in liposomes, e.g. starting from phosphatidylcholine, in microspheres, in nanospheres or also in capsules, granules or extrudates into a matrix suitable for food and beverages, e.g. starch, starch derivatives, cellulose or cellulose derivatives (e.g. hydroxypropylcellulose), other polysaccharides (e.g. alginate), natural fats, natural waxes (e.g. beeswax, carnauba wax) or proteins, e.g. gelatin.

[0136] In a manufacturing process, hesperetin dihydrochalcone (I) and / or its salts are first complexed with a variety of suitable complexing agents, e.g. with cyclodextrins or cyclodextrin derivatives, preferably α- or β-cyclodextrin, and used in this complexed form.

[0137] A preparation according to the invention is particularly preferred in which the matrix is ​​selected such that the hesperetin dihydrochalcone (I) and / or the salt(s) of the hesperetin dihydrochalcone (I) experience a delayed release from the matrix, so that a long-lasting effect is achieved.

[0138] Further ingredients for preparations according to the invention for nutrition or enjoyment may include basic substances, auxiliary substances and additives in a preparation according to the invention (as described above) or be used for the production of such preparations, e.g. B. Water, mixtures of fresh or processed, plant or animal raw materials (e.g., raw, roasted, dried, fermented, smoked and / or cooked meat, bones, cartilage, fish, vegetables, fruits, herbs, nuts, vegetable or fruit juices or pastes or mixtures thereof), digestible or indigestible carbohydrates (e.g., sucrose, maltose, fructose, glucose, dextrins, amylose, amylopectin, inulin, xylans, cellulose, tagatose), sugar alcohols (e.g., sorbitol, erythritol), natural or hydrogenated fats (e.g., tallow, lard, palm oil, coconut oil, hydrogenated vegetable fat), oils (e.g.,Sunflower oil, peanut oil, corn oil, olive oil, fish oil, soybean oil, sesame oil), fatty acids or their salts (e.g. potassium stearate), proteinogenic or non-proteinogenic amino acids and related compounds (e.g. γ-minobutyric acid). B. γ-Minobutyric acid, taurine), peptides (e.g., glutathione), natural or processed proteins (e.g., gelatin), enzymes (e.g., peptidases), nucleic acids, nucleotides, other flavor-correcting agents or flavor modulators for unpleasant or non-unpleasant taste sensations, in particular flavor-modulating substances (e.g., inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate, or other substances such as monosodium glutamate or 2-phenoxypropionic acid), emulsifiers (e.g., lecithins, diacylglycerols, gum arabic), stabilizers (e.g., carrageenan, alginate), preservatives (e.g., benzoic acid, sorbic acid), antioxidants (e.g., tocopherol, ascorbic acid), chelators (e.g.,Citric acid), organic or inorganic acidulants (e.g., malic acid, acetic acid, citric acid, tartaric acid, phosphoric acid), (possibly other) bitter substances (e.g., quinine, caffeine, limonin, amarogentin, humulone, lupolone, catechins, tannins), (possibly other) sweeteners (e.g., saccharin, cyclamate, aspartame, neotame), mineral salts (e.g., sodium chloride, potassium chloride, magnesium chloride, sodium phosphates), substances that prevent enzymatic browning (e.g., sulfite, ascorbic acid), essential oils, plant extracts, natural or synthetic dyes or color pigments (e.g., carotenoids, flavonoids, anthocyanins, chlorophyll and their derivatives), spices, substances with trigeminal activity or plant extracts containing such substances with trigeminal activity, synthetic, natural or nature-identical flavorings or fragrances, and odor correction agents.

[0139] Dental care products (as a basis for oral care preparations according to the invention) generally comprise an abrasive system (grinding or polishing agent), such as silicas, calcium carbonates, calcium phosphates, aluminum oxides and / or hydroxyapatites; surfactants, such as sodium lauryl sulfate, sodium lauryl sarcosinate and / or cocamidopropyl betaine; humectants, such as glycerin and / or sorbitol; thickeners, such as carboxymethylcellulose, polyethylene glycols, carrageenan and / or laponites. ®, (possibly other) sweeteners, such as saccharin, flavor-correcting agents for unpleasant or generally non-unpleasant taste sensations, flavor-modifying substances (e.g., inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate, or other substances such as sodium glutamate or 2-phenoxypropionic acid), cooling active ingredients, such as, for example, menthol, menthol derivatives (e.g., L-menthol, L-menthyllate, L-menthyl alkyl carbonates, menthone ketals, menthane carboxylic acid amides), 2,2,2-trialkylacetic acid amides (e.g., 2,2-diisopropylpropionic acid methylamide), icilin derivatives, stabilizers, and active ingredients, such as...Sodium fluoride, sodium monofluorophosphate, tin difluoride, quaternary ammonium fluorides, zinc citrate, zinc sulfate, tin pyrophosphate, tin dichloride, mixtures of various pyrophosphates, triclosan, cetylpyridinium chloride, aluminum lactate, potassium citrate, potassium nitrate, potassium chloride, strontium chloride, hydrogen peroxide, flavorings and / or sodium bicarbonate or odor correcting agents.

[0140] Chewing gums (as a further example of preparations according to the invention that serve oral care) generally contain a chewing gum base, i.e., a chewable mass that becomes plastic when chewed, sugars of various kinds, sugar substitutes, sweeteners, sugar alcohols, flavor correction agents or flavor modulators for further unpleasant or generally non-unpleasant taste sensations, flavor-modulating substances (e.g., inositol phosphate), nucleotides such as guanosine monophosphate, adenosine monophosphate, or other substances such as sodium glutamate or 2-phenoxypropionic acid, humectants, thickeners, emulsifiers, flavorings, and stabilizers or odor correction agents.

[0141] All commonly used basic, excipient, and additive substances for oral pharmaceutical preparations can be used as ingredients for oral preparations according to the invention. In particular, orally formulated pharmaceutical active ingredients with an unpleasant taste, especially bitter-tasting substances, can also be used as active ingredients, the bitter taste of which can be masked or reduced according to the invention. The active ingredients, basic substances, excipients, and additives can be converted into oral dosage forms in a manner known per se. This is generally done with inert, non-toxic, pharmaceutically suitable excipients. These include, among others, carriers (e.g., microcrystalline cellulose), solvents (e.g., liquid polyethylene glycols), emulsifiers (e.g., sodium dodecyl sulfate), dispersants (e.g., polyvinylpyrrolidone), synthetic and natural biopolymers (e.g., albumin), and stabilizers (e.g.,Antioxidants such as ascorbic acid), colorants (e.g. inorganic pigments such as iron oxides) and odor and taste correction agents, especially those that do not affect the bitter taste.

[0142] Preferably, preparations according to the invention (as described above) may also contain a (non-inventive) flavoring composition to (further) round off and refine the taste and / or smell of the preparation. Suitable flavoring compositions contain, for example, synthetic, natural, or nature-identical flavorings, fragrances, and flavoring agents, as well as suitable excipients and carriers. It is considered particularly advantageous that a bitter or metallic taste impression arising from the flavorings, fragrances, or flavorings contained in the preparations according to the invention can be masked or reduced, thus improving the overall taste profile.

[0143] Preparations according to the invention in the form of semi-finished products can be used to mark or reduce an unpleasant taste impression of finished product preparations that were produced using the semi-finished preparation.

[0144] In a particularly preferred embodiment of the present invention, the hesperetin dihydrochalcone (I) or its salts used according to the invention are combined with at least one further substance in an aroma composition or preparation according to the invention containing an aroma composition (as described above) to modify, mask, or reduce an unpleasant taste sensation and / or to intensify a pleasant taste sensation, wherein the pleasant taste sensation is preferably a sweet and / or umami taste. In this way, a particularly effective masking effect can be achieved.

[0145] Further substances for masking or reducing an unpleasant taste impression and / or for enhancing a pleasant taste impression or taste-correcting agents are – without limiting the present invention thereto – preferably selected from the group consisting of nucleotides (for example, adenosine 5'-monophosphate, cytidine 5'-monophosphate) or their pharmaceutically acceptable salts, lactisols, sodium salts (e.g., sodium chloride, sodium lactate, sodium citrate, sodium acetate, sodium gluconoate), hydroxyflavanones, e.g., eriodictyol, sterubine (eriodictyol-7-methyl ether), homoeriodictyol, and their sodium, potassium, calcium, magnesium, or zinc salts (in particular those such as those in EP 1 258 200, which is incorporated into this application by reference to the corresponding compounds disclosed therein), hydroxybenzoic acid amides, etc. B. 2,4-dihydroxybenzoic acid vanillylamide, 2,4-dihydroxybenzoic acid N-(4-hydroxy-3-methoxybenzyl)amide, 2,4,6-trihydroxybenzoic acid-N-(4-hydroxy-3-methoxybenzyl)amide, 2-hydroxybenzoic acid-N-4-(hydroxy-3-methoxybenzyl)amide, 4-hydroxybenzoic acid-N-(4-hydroxy-3-methoxybenzyl)amide, 2,4-Dihydroxybenzoic acid-N-(4-hydroxy-3-methoxybenzyl)amide mono-sodium salt, 2,4-Dihydroxybenzoic acid-N-2-(4-hydroxy-3-methoxyphenyl)ethylamide, 2,4-Dihydroxybenzoic acid-N-(4-hydroxy-3-ethoxybenzyl)amide, 2,4-Dihydroxybenzoic acid N-(3,4-dihydroxybenzyl)amide and 2-hydroxy-5-methoxy-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]amide; 4-Hydroxybenzoic acid vanillylamide (in particular those described in WO 2006 / 024587, which, with reference to the corresponding compounds disclosed therein, is part of this application); hydroxydeoxybenzoines, for example 2-(4-hydroxy-3-methoxyphenyl)-1-(2,4,6-trihydroxyphenyl)ethanone, 1-(2,4-dihydroxyphenyl)-2-(4-hydroxy-3-methoxyphenyl)ethanone, 1-(2-hydroxy-4-methoxyphenyl)-2-(4-hydroxy-3-methoxyphenyl)ethanone) (in particular those described in WO 2006 / 106023,which is part of this application by reference to the corresponding compounds disclosed therein); hydroxyphenylalkandiones, e.g., gingerdione-[2], gingerdione-[3], gingerdione-[4], dehydrogingerdione-[2], dehydrogingerdione-[3], dehydrogingerdione-[4]) (in particular those as described in WO 2007 / 003527, which is part of this application by reference to the corresponding compounds disclosed therein); diacetyl trimers (in particular those described in WO 2006 / 058893, which is part of this application by reference to the corresponding compounds disclosed therein); gamma-aminobutyric acids (in particular those described in WO 2005 / 096841, which is part of this application by reference to the corresponding compounds disclosed therein); divanillins (in particular those as described in WO 2004 / 078302,which is part of this application by reference to the corresponding compounds disclosed therein) and 4-hydroxydihydrochalcones (preferably as described in US 2008 / 0227867 A1, which is part of this application by reference to the corresponding compounds disclosed therein), in this respect in particular phloretin and vidigenin, amino acids or mixtures of whey proteins with lecithins, hesperetin as disclosed in WO 2007 / 014879, which is part of this application by reference to the corresponding compounds, 4-hydroxychalcones as disclosed in WO 2007 / 107596, which is part of this application by reference to the corresponding compounds, or propylene phenyl glycosides (chavicol glycosides) as described in EP 1 955 601 A1, which is part of this application by reference to the corresponding compounds, pellitorin and flavor compositions derived therefrom, as in US Provisional Application 60 / 944,854 and in the patent applications based thereon, umami compounds as described in WO 2008 / 046895 and EP 1 989 944 A1, which are each incorporated into the present application by reference to the corresponding compounds; Matairesinol and neoflavonoid as described in WO 2012 / 146584 A1, US 2013 078192 A1 and US 2013 084252 A1, neoisoflavonoids as described in EP 2,570,035, EP 2,725,026 or EP 2,570,036, each of which are incorporated into this application by reference to the corresponding compounds, and umami compounds as described in US Provisional Application 60 / 984,023 or US Provisional Application 61 / 061,273 and in the patent applications based thereon, which are incorporated into this application by reference to the corresponding compounds disclosed therein.

[0146] Combinations with homoeriodictyol, eriodictyol and the sodium, potassium, calcium, magnesium or zinc salts of both compounds, matairesinol, neoflavonoids, divanillins, phloretin and / or hesperetin are particularly preferred.

[0147] Furthermore, a method for masking, reducing or suppressing an unpleasant, preferably bitter, sour and / or astringent taste impression of unpleasant-tasting substances or mixtures of substances, in particular the bitter taste impression of bitter-tasting substances or mixtures of substances, and / or is disclosed. Selected for modulating taste impressions from the group of cooling, sweet, umami, fruity and spicy notes of cooling, sweet, umami, fruity or spicy tasting substances or mixtures of substances, and / or simultaneously to intensify - preferably synergistically - the sweet taste impression of sweet-tasting substances or mixtures of substances, or of both sweet and bitter-tasting substances or mixtures of substances with the following step - Mixing the following components (a) Hesperet dihydrochalcone (I) or a salt of hesperet dihydrochalcone (I) or a mixture comprising or consisting of several salts of hesperet dihydrochalcone (I) or a mixture comprising or consisting of hesperet dihydrochalcone (I) and a salt or several salts of hesperet dihydrochalcone (I), and at least one or more of the substances selected from the group consisting of substance(s) (c) and (d) or mixtures thereof, wherein - Substance(s) (c) means one or more unpleasant-tasting substances, preferably bitter, sour and / or astringent-tasting substances, in particular bitter-tasting substances. - Substance8) (d) means one or more substances that taste both sweet and unpleasant, especially bitter; and / or (b) one or more sweet-tasting substances, and possibly other components wherein components (b)-(h) do not contain hesperetindihydrochalcone (I) or a salt of hesperetindihydrochalcone (I), and wherein the total amount of component (a) in the mixture is sufficient to mask, reduce or suppress an unpleasant taste sensation, preferably a bitter, sour and / or astringent taste sensation of unpleasant-tasting substances or mixtures of substances, in particular a bitter taste sensation of bitter-tasting substances, and / or to modulate the taste impressions selected from the group consisting of cooling, umami, fruity and spicy notes from cooling, umami, fruity or spicy tasting substances or mixtures of substances, and at the same time to enhance the sweet taste impression of sweet-tasting substances or mixtures of substances, or of both sweet and bitter-tasting substances or mixtures of substances - preferably synergistically.

[0148] The method for masking, reducing or suppressing an unpleasant, preferably bitter, sour and / or astringent taste impression of unpleasant-tasting substances or mixtures of substances, in particular a bitter taste impression of bitter-tasting substances or mixtures of substances, and / or Selected for modulating taste impressions from the group of cooling, sweet, umami, fruity and spicy notes of cooling, sweet, umami, fruity or spicy tasting substances or mixtures of substances, and / or Simultaneously to intensify - preferably synergistically - the sweet taste impression of sweet-tasting substances or mixtures of substances, or of both sweet and bitter-tasting substances or mixtures of substances, comprising the following step: - Mixing the following components (a) Hesperet dihydrochalcone (I) or a salt of hesperet dihydrochalcone (I) or a mixture comprising or consisting of several salts of hesperet dihydrochalcone (I) or a mixture comprising or consisting of hesperet dihydrochalcone (I) and a salt or several salts of hesperet dihydrochalcone (I), and at least one or more of the substances selected from the group consisting of substances (c) and (d) or mixtures thereof, wherein - Substance(s) (c) means one or more unpleasant-tasting substances, preferably bitter, sour and / or astringent-tasting substances, in particular bitter-tasting substances. - Substance(s) (d) means one or more substances that taste both sweet and unpleasant, especially bitter-tasting substances; and (e) one or more substances for masking or reducing an unpleasant, especially bitter, taste sensation; and / or (b) one or more sweet-tasting substances, and possibly other components wherein components (b)-(h) do not contain hesperetin dihydrochalcone (I) or a salt of hesperetin dihydrochalcone (I), and wherein the total amount of component (a) in the mixture is sufficient to mask, reduce or suppress an unpleasant taste sensation, preferably a bitter, sour and / or astringent taste sensation of unpleasant-tasting substances or mixtures of substances, in particular a bitter taste sensation of bitter-tasting substances, and / or to modulate the taste impressions selected from the group of cooling, umami, fruity and spicy notes of cooling, umami, fruity or spicy tasting substances or mixtures of substances, and at the same time to enhance the sweet taste impression of sweet-tasting substances or mixtures of substances, or of both sweet and bitter-tasting substances or mixtures of substances - preferably synergistically.

[0149] The method described here for masking, reducing or suppressing an unpleasant, preferably bitter, sour and / or astringent taste impression of unpleasant-tasting substances or mixtures of substances, in particular a bitter taste impression of bitter-tasting substances or mixtures of substances, and / or Selected for modulating taste impressions from the group of cooling, sweet, umami, fruity and spicy notes of cooling, sweet, umami, fruity or spicy tasting substances or mixtures of substances, and / or simultaneously to intensify - preferably synergistically - the sweet taste impression of sweet-tasting substances or mixtures of substances, or of both sweet and bitter-tasting substances or mixtures of substances with the following step - Mixing the following components (a) Hesperetin dihydrochalcone (I) or a salt of hesperetin dihydrochalcone (I) or a mixture comprising or consisting of a plurality of salts of hesperetin dihydrochalcone (I), or a mixture comprising or consisting of hesperetin dihydrochalcone (I) and a salt or a plurality of salts of hesperetin dihydrochalcone (I) and at least one or more of the substances selected from the group consisting of substance(s) (c) and (d) or mixtures thereof, wherein - Substance(s) (c) means one or more unpleasant-tasting substances, preferably bitter, sour and / or astringent-tasting substances, in particular bitter-tasting substances. - Substance(s) (d) means one or more substances that taste both sweet and unpleasant, especially bitter-tasting substances; and (e) at least one of the substances selected from the group consisting of homoeriodictyol or its sodium salts, eriodictyol, matairesinol, lariciresinol, naringenin, phloretin, 5-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-7-methoxychroman-2-one, 5,7-dihydroxy-4-(4-hydroxyphenyl)-chroman-2-one, 5,7-dihydroxy-4-(4-hydroxy-3-methoxyphenyl)-chroman-2-one and 2,4-dihydroxybenzoic acid vanillylamide, and optionally other substances to mask or reduce an unpleasant, especially bitter, taste impression; and / or (b) one or more sweet-tasting substances and, if necessary, other components wherein components (b)-(h) do not contain hesperetindihydrochalcone (I) or a salt of hesperetindihydrochalcone (I), and wherein the total amount of component (a) in the mixture is sufficient to mask, reduce or suppress an unpleasant taste sensation, preferably a bitter, sour and / or astringent taste sensation of unpleasant-tasting substances or mixtures of substances, in particular a bitter taste sensation of bitter-tasting substances, and / or to modulate the taste impressions selected from the group of cooling, umami, fruity and spicy notes of cooling, umami, fruity or spicy tasting substances or mixtures of substances, and at the same time to enhance the sweet taste impression of sweet-tasting substances or mixtures of substances, or of both sweet and bitter-tasting substances or mixtures of substances - preferably synergistically.

[0150] The method described here for masking, reducing or suppressing an unpleasant, preferably bitter, sour and / or astringent taste impression of unpleasant-tasting substances or mixtures of substances, in particular a bitter taste impression of bitter-tasting substances or mixtures of substances, and / or selected for modulating taste impressions from the group of cooling, sweet, umami, fruity and spicy notes of cooling, sweet, umami, fruity or spicy tasting substances or mixtures of substances, and / or simultaneously for intensifying - preferably synergistically - the sweet taste impression of sweet-tasting substances or mixtures of substances, or of both sweet and bitter-tasting substances or mixtures of substances, comprising the following step - Mixing the following components (a) Hesperetin dihydrochalcone (I) or a salt of hesperetin dihydrochalcone (I) or a mixture comprising or consisting of a plurality of salts of hesperetin dihydrochalcone (I), or a mixture comprising or consisting of hesperetin dihydrochalcone (I) and a salt or a plurality of salts of hesperetin dihydrochalcone (I) and at least one or more of the substances selected from the group consisting of substance(s) (c) and (d) or mixtures thereof, wherein - Substance(s) (c) means one or more unpleasant-tasting substances, preferably bitter, sour and / or astringent-tasting substances, in particular bitter-tasting substances. - Substance(s) d) one or more substances that taste both sweet and unpleasant, in particular bitter-tasting substances, and (e) Homoeriodictyol or its sodium salts and optionally at least one of the substances selected from the group consisting of eriodictyol, matairesinol, lariciresinol, naringenin, phloretin, 5-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-7-methoxychroman-2-one, 5,7-dihydroxy-4-(4-hydroxyphenyl)-chroman-2-one, 5,7-dihydroxy-4-(4-hydroxy-3-methoxyphenyl)-chroman-2-one or 2,4-dihydroxybenzoic acid vanillylamide and optionally further substances for masking or reducing an unpleasant, in particular bitter, taste impression; and / or (b) one or more sweet-tasting substances and, where appropriate, other components, wherein components (b)-(h) do not contain hesperetindihydrochalcone (I) or a salt of hesperetindihydrochalcone (I), and wherein the total amount of component (a) in the mixture is sufficient to mask, reduce or suppress an unpleasant taste sensation, preferably a bitter, sour and / or astringent taste sensation of unpleasant-tasting substances or mixtures of substances, in particular a bitter taste sensation of bitter-tasting substances, and / or to modulate the taste impressions selected from the group of cooling, umami, fruity and spicy notes of cooling, umami, fruity or spicy tasting substances or mixtures of substances, and at the same time to intensify the sweet taste impression of sweet-tasting substances or mixtures of substances, or of both sweet and bitter-tasting substances or mixtures of substances - preferably synergistically.

[0151] A process according to the disclosure is described here, wherein the total amount of components (a) in the mixture is sufficient to - to mask, reduce or suppress an unpleasant taste sensation, preferably a bitter, sour and / or astringent taste sensation from unpleasant-tasting substances or mixtures of substances, in particular a bitter taste sensation from bitter-tasting substances, and / or - to enhance the sweet taste of the sweet-tasting substance - preferably synergistically - and / or - to enhance the sweet taste impression of a substance or mixture of substances that tastes both sweet and unpleasant, especially bitter, preferably synergistically, and to reduce or modify the unpleasant, especially bitter, taste impression of the substance or mixture of substances that tastes both sweet and unpleasant, especially bitter.

[0152] A process according to the disclosure is described here, wherein the total amount of components (a) in the mixture is sufficient to - to mask, reduce or suppress an unpleasant, preferably bitter, sour and / or astringent taste impression of unpleasant-tasting substances or mixtures of substances, in particular a bitter taste impression of bitter-tasting substances, and - to modulate the taste impressions selected from the group of cooling, umami, fruity and spicy notes of cooling, umami, fruity or spicy tasting substances or mixtures of substances, and - to enhance the sweet taste of the sweet-tasting substance - preferably synergistically - and / or - to enhance the sweet taste impression of a substance or mixture of substances that tastes both sweet and unpleasant, especially bitter, preferably synergistically, and to reduce or modify the unpleasant, especially bitter, taste impression of substances or mixtures of substances that taste both sweet and unpleasant, especially bitter.

[0153] A process according to the disclosure is described here, wherein the total amount of components (a) in the mixture is sufficient to - to mask, reduce or suppress an unpleasant, preferably bitter, sour and / or astringent taste impression of unpleasant-tasting substances or mixtures of substances, in particular a bitter taste impression of bitter-tasting substances, and - to modulate the taste impressions selected from the group of cooling, umami, fruity and spicy notes of cooling, umami, fruity or spicy tasting substances or mixtures of substances, and - to enhance - preferably synergistically - the sweet taste of the sweet-tasting substance, and - to intensify the sweet taste impression of a substance or mixture of substances that tastes both sweet and unpleasant, especially bitter, preferably synergistically, and to reduce or modify the unpleasant, especially bitter, taste impression of the substance or mixture of substances that tastes both sweet and unpleasant, especially bitter.

[0154] This last variant of the procedure is particularly preferred.

[0155] The above applies accordingly to further preferred embodiments of a process according to the disclosure, in particular for hesperet dihydrochalcone (I) and its salts and the preferred choice of substances (b), (c), (d) or (e).

[0156] The invention is described in more detail below using examples. These examples serve to illustrate the invention without limiting the scope of protection of the claims. All numerical data refer to weight unless otherwise stated. EXAMPLE EXAMPLE 1 Synthesis of 3-(3-Hydroxy-4-methoxy-phenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one (Hesperetin dihydrochalcone (I))

[0157] Neohesperidin dihydrochalcone was heated under reflux in a 2 M H₂SO₄ / MeOH mixture (1:1) for 6 hours. After cooling to room temperature, the reaction mixture was neutralized by adding 2 M NaOH and filtered. The resulting solid was washed with water (3x) and dried under vacuum at 40 °C to obtain hesperetin dihydrochalcone (I) as a white solid (yield: 77%).

[0158] 1 H-NMR (400 MHz, DMSO-d 6) : δ = 12.25 (s, 2H), 10.36 (s, 1H), 8.79 (s, 1H), 6.80 (d, J = 8.2 Hz, 1H), 6.66 (d, J = 2.1 Hz, 1H), 6.59 (dd, J = 8.2, 2.2 Hz, 1H), 5.81 (s, 2H), 3.72 (s, 3H), 3.22 (dd, J = 8.5, 6.9 Hz, 2H), 2.74 (dd, J = 8.5, 6.9 Hz, 2H).

[0159] 13 C NMR (101 MHz, DMSO-d 6) : δ = 203.97, 164.51, 164.12 (2C), 146.19, 145.70, 134.13, 118.59, 115.61, 112.24, 103.60, 94.54 (2C), 55.59, 45.11, 29.42. EXAMPLE 2: Bitterness reduction of a bitter substance solution

[0160] To quantify the decrease (i.e., the masking or reduction) of the bitterness impression in a sample, the bitterness of a solution containing various bitter-tasting substances in specific concentrations was compared by a group of experts (n=18) with a sample having an equivalent composition and additionally a specific concentration of hesperet dihydrochalcone (I) (rating: 1 [not bitter] to 100 [extremely bitter]).

[0161] For the evaluation, i.e., the calculation of the reduction (in %) of the bitterness impression, the mean values ​​of the expert group's assessments for the respective bitterness solution and the bitterness solution also containing 10 ppm hesperetin dihydrochalcone (I) were used (*significant lev. α = 0.05). For comparison purposes, the calculation of the reduction (in %) of the bitterness impression for the respective bitterness solution with deoxy-hesperetin dihydrochalcone is also included. Table 1 Performance Study Bitter substance Bitter impression of the bitter substance (average values) Bitter impression of bitter substance + compound (I) (average values) Reduction of bitterness by adding 10 ppm of compound (I) Reduction of bitterness by adding 50 ppm deoxy-hesperetin dihydrochalcone 500 ppm caffeine 43.44 37.46 -13.8% -11.3% 100 ppm Naringin 59.29 46.54 -21.5%* -6.6% 300 ppm theobromine 51.35 45.01 -12.4% n / a 250 ppm salicin 62.35 51.40 -17.6%* -15.2% 5 ppm quinine hydrochloride 38.72 29.05 -25.0% +10.7%

[0162] Surprisingly, it was found that the amount of deoxy-hesperetin dihydrochalcone must be 5 times higher than the corresponding amount of hesperetin dihydrochalcone (I) to achieve a similar effect in reducing the bitterness impression.

[0163] It was also shown that, in the case of naringin, a significantly greater reduction in bitterness was achieved with hesperetin dihydrochalcone(I) compared to deoxy-hesperetin dihydrochalcone. While 50 ppm deoxy-hesperetin dihydrochalcone did not reduce the bitterness of quinine hydrochloride, a remarkable reduction in the bitterness of quinine hydrochloride was achieved with only 10 ppm hesperetin dihydrochalcone(I). EXAMPLE 3: Intensifying the sweet impression of a sugar solution

[0164] To quantify the enhancement of the sweet impression, an expert panel compared the sweetness of a 5% sucrose solution with a sample containing 5% sucrose and 1 ppm, 5 ppm, 7 ppm, or 10 ppm of the hesperetin dihydrochalcone (I) used according to the invention (rating: 1 [not sweet] to 10 [extremely sweet]). For comparison purposes, the enhancement of the sweet impression with a sample containing 5% sucrose and 10 ppm or 25 ppm deoxy-hesperetin dihydrochalcone is also included.

[0165] For the evaluation, i.e. the calculation of the enhancement (in %) of the sweet impression, the mean values ​​of the expert group's evaluations for the sucrose solution and the comparison sample with sucrose and hesperet dihydrochalcone (I) or deoxy-hesperet dihydrochalcone were used. Table 2 Performance Study Test (comparison) substance Sucrose (sweetener) Sweet impression (1-10) Reinforcement of the sweet impression sucrose solution Sample (sucrose + test substance) 1 ppm hesperetin dihydrochalcone (I) 5 % 5.3 6.1 14.1 %(α = 0.05) 5 ppm hesperetin dihydrochalcone (I) 5 % 5.3 7.1 32.6 %(α = 0.05) 7 ppm hesperetin dihydrochalcone (I) 5 % 5.4 7.3 35.7 %(α = 0.05) 10 ppm hesperetin dihydrochalcone (I) 5 % 5.6 7.8 38.6 %(α = 0.05) 10 ppm deoxy-hesperetin dihydrochalcone 5% 5.3 6.4 21.2%(α = 0.05) 25 ppm deoxy-hesperetin dihydrochalcone 5% 4.9 6.9 42%(α = 0.003)

[0166] Surprisingly, it was found that a remarkable intensification of the sweet impression is achieved by using hesperetin dihydrochalcone (I) at an amount of 10 ppm compared to the intensification of the sweet impression achieved by using the same amount (10 ppm) of deoxy-hesperetin dihydrochalcone.

[0167] Furthermore, it was surprisingly found that the intensification of the sweet impression was significantly higher when using hesperetin dihydrochalcone (I) at a concentration of 5 ppm than the intensification of the sweet impression when using deoxy-hesperetin dihydrochalcone at a concentration of 10 ppm. EXAMPLE 4 Intrinsic sweetness of hesperet dihydrochalconone (I)

[0168] A group of 30 experts were asked to select the solution with the stronger sweetness perception from a pair of solutions in a two-alternative forced choice (2AFC) test. The evaluated solution pairs were selected from a group consisting of a solution of hesperetin dihydrochalcone (I) in water (20 ppm, 15 ppm, 12.5 ppm and 10 ppm) and a 1.5 wt% aqueous sucrose solution.

[0169] A solution of 10 ppm hesperetin dihydrochalcone (I) was described as significantly weaker in terms of sweetness compared to the 1.5 wt% aqueous sucrose solution (α = 0.05). EXAMPLE 5: Modification of the sweetness profile

[0170] The taste profile of a 7 wt% aqueous sucrose solution was compared by a group of experts (n= 12) with a sample of the same composition that additionally contained 1.5% sucrose (B), 5 ppm, 7 ppm or 20 ppm hesperet dihydrochalcone (I). Table 3 Performance Study Test solution Onset of the sweet sensation (< 2 seconds) Sweet overall impression Full sugar aroma and taste A 7% sucrose solution 3.55 3.95 3.30 B 7% sucrose solution + 1.5% sucrose (= 8.5% sucrose solution) 5.74 6.36 5.17 C 7% sucrose solution + 5 ppm hesperetin dihydrochalcone (I) 4.63 5.24 4.26 D 7% sucrose solution + 7 ppm hesperet dihydrochalcone (I) 4.78 5.93 4.42 E 7% sucrose solution + 20 ppm hesperetin dihydrochalcone (I) 4.49 4.90 4.11

[0171] As summarized in the table above, hesperetin dihydrochalcone (I) not only increases the overall sweetness impression but also has a particularly positive effect on the onset of the sweetness impression (sweet impact) and the perceived whole sugar odor and taste. Thus, a surprising improvement in sensory properties was achieved. EXAMPLE 6: Improving the flavor profile of chicken flavor

[0172] A group of experts (n=3) assessed the effect of adding 2 ppm hesperetin dihydrochalcone (I) on the flavor profile of a chicken flavor with the typical descriptors chicken meat note, cooked note, bonery, slightly acidic. A significant increase in mouthfeel was achieved without negatively affecting the aforementioned flavor profile. EXAMPLE 7 Modulation of the cooling profile of WS-3

[0173] A group of experts (n=5) evaluated the influence of an aqueous solution containing 5 wt% sucrose and 4 ppm WS-3 on the cooling profile. An otherwise equivalent composition containing an additional 1 ppm hesperetin dihydrochalcone (I) showed a faster perception of the cooling sensation and also a slight improvement in the cooling effect. APPLICATION EXAMPLE APPLICATION EXAMPLE 1 Spray-dried preparation as a semi-finished product for flavoring finished products ingredient Use in wt.% preparation A B C D E Drinking water 60.8 60.8 60.8 60.8 60.8 Maltodextrin from wheat 31.5 29.7 28.8 27.0 27.9 Gum arabic 6.1 6.1 6.1 6.1 6.1 Hesperetin dihydrochalcone (I) 1.6 1.2 1.0 0.6 0.8 Hesperetin - 2.2 - - 1.1 Homoeriodictyol sodium salt - - - 5.5 3.3 Phloretin - - 3.3 - -

[0174] Drinking water is placed in a container, and maltodextrin and gum arabic are dissolved in it. The flavoring is then emulsified in the carrier solution using a Turrax. The temperature of the spray solution should not exceed 30 °C. The mixture is then spray-dried (nominal inlet temperature: 185–195 °C, nominal outlet temperature: 70–75 °C). APPLICATION EXAMPLE 2 Combination with sweeteners

[0175] To 0.5 g of a spray-dried semi-finished product from application example 1 (according to preparation A), 90 g of sucrose and 10 g of tagatose are added and mixed. The product can be used, for example, as a sweetener with a bitter-masking effect for coffee or tea. APPLICATION EXAMPLE 3 Chewing gum Part ingredient wt.% A Chewing gum base from the company "Jagum T" 30.0 B Sorbitol, powdered 39.0 Isomalt (®) ( Palatinit GmbH) 9.5 Xylitol 2.0 Mannitol 3.0 Rebaudioside A 98% 0.2 Emulsification (®) ( Natural Colloids, Inc.) 0.3 C Sorbitol, 70% 14.0 glycerin 1.0 D Aroma containing 0.1% w / w hesperetin dihydrochalcone (I), based on the total weight of the aroma 1.0

[0176] Parts A to D are mixed and kneaded intensively. The raw mixture can then be processed, for example, into thin strips of ready-to-eat chewing gum. APPLICATION EXAMPLE 4 Toothpaste Part ingredient wt.% A Demineralized water 22.00 Sorbitol (70%) 46.00 Solbrol (®) M , sodium salt (Bayer AG, p-hydroxybenzoic acid alkyl ester) 0.15 trisodium phosphate 0.10 Rebaudioside A, 98% 0.10 Sodium monofluorophosphate 1.12 Polyethylene glycol 1500 5.00 B Sident 9 (abrasive silicon dioxide) 10.00 Sident 22 S (thickening silicon dioxide) 8.00 Sodium carboxymethylcellulose 0.90 Titanium dioxide 0.50 C Demineralized water 4.63 Sodium lauryl sulfate 1.50 D Aroma containing 0.1% w / w hesperetin dihydrochalcone (I), based on the total weight of the aroma 1.00

[0177] The ingredients for parts A and B are premixed separately and stirred thoroughly under vacuum at 25-30 °C for 30 minutes. Part C is premixed and added to A and B; part D is added, and the mixture is stirred thoroughly under vacuum at 25-30 °C for 30 minutes. After pressure release, the toothpaste is ready and can be bottled. APPLICATION EXAMPLE 5 Sugar-free hard-boiled candy ingredient Salary (%) A B C D Palatinite, type M 75.00 74.00 75.50 75.00 citric acid - 1.00 0.50 - dye, yellow - 0.01 - - Coloring, red - - 0.01 - Coloration, blue 0.01 - - 0.01 Peppermint flavor 0.1 - - 0.1 Lemon flavor - 0.1 - - Red fruit aroma - - 0.1 - Rebaudioside A 98%. - 0.040 - 0.040 Hesperetin dihydrochalcone (I) 0.001 0.0005 0.001 0.0005 Hesperetin - 0.001 - 0.001 Phloretin - 0.002 - - Water ad 100

[0178] Palatinit was mixed with water, the mixture was melted at 165 °C, and then cooled to 115 °C. The remaining ingredients were added, and after mixing, the mixture was poured into molds, demolded after hardening, and then individually packaged. APPLICATION EXAMPLE 6: Reduced-sugar tomato ketchup A: Comparative preparation with sugar B: Comparison preparation with reduced sugar content (compared to A) CH: Preparations according to the invention with reduced sugar content (compared to A) and hesperet dihydrochalcone (I) ingredient Preparation (amounts in wt.%) A B C D E F G H table salt 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 Strength, Farinex WM 55 1.0 1.0 1.0 1.0 1.0. 1.0 1.0 1.0 sucrose 12.0 9.6 9.2 8.4 9.6 9.6 8.4 8.4 Tomato concentrate x 2 40.0 40.0 40.0 40.0 30.0 30.0 30.0 30.0 Glucose syrup 80 Brix 18.0 18.0 18.0 18.0 18.0 18.0 18.0 18.0 Spirit vinegar 10%. 7.0 7.0 7.0 7.0 3.0 3.0 3.0 3.0 Hesperetin dihydrochalcone (I) 0.5% in 1,2-propylene glycol 0.2 0.1 0.1 0.2 0.1 0.1 Hesperetin 2.5% in 1,2-propylene glycol 0.1 0.2 Phloretin 2.5% in 1,2-propylene glycol 0.2 0.2 0.2 Water ad 100

[0179] The ingredients are mixed in the specified order, and the finished ketchup is homogenized with a mixer, bottled, and sterilized. APPLICATION EXAMPLE 7: Sugar-reduced fruit gummies ingredient A (wt%), Comparative Preparation B ((wt%), preparation according to the present invention Water 23.70 25.80 sucrose 34.50 8.20 Glucose syrup, DE 40 31.89 30.09 Iso-Syrup C* Tru Sweet 01750 (Cerestar GmbH) 1.50 2.10 Gelatine 240 Bloom 8.20 9.40 Polydextrose (Litesse ® Ultra, Danisco Cultor GmbH) - 24.40 Yellow and red dyes 0.01 0.01 citric acid 0.20 Cherry flavoring containing 1% w / w hesperetin dihydrochalcone (I), based on the flavoring. - 0.10

[0180] Note: Polydextrose is itself a non-sweet-tasting polysaccharide with a low calorific value. APPLICATION EXAMPLE 8 Gelatin capsules for direct consumption ingredient A (in percent by weight) B (in percent by weight) C (in percent by weight) Gelatin shell: Glycerin 2.014 2.014 2.014 Gelatine 240 Bloom 7.91 7.91 7.91 Sucralose 0.065 0.065 0.065 Allura Red 0.006 0.006 0.006 Brilliant blue 0.005 0.005 0.005 Core composition: Vegetable oil triglyceride (coconut oil fraction) 79.55 68.70 77.60 Orange flavoring containing 0.005 wt% hesperetin dihydrochalcone (I), based on the total weight of the flavoring 10.00 20.00 10.00 Rebaudioside A 98%. 0.05 0.05 - 2-Hydroxypropylmenthyl carbonate 0.33 0.20 - 2-Hydroxyethylmethylcarbonate - 0.20 1.00 (1R,3R,4S) Menthyl-3-carboxylic acid-N-ethylamide (WS-3) - 0.55 0.50 (-)-Menthone glycerol acetal (Frescolat MGA) - 0.30 0.80 Vanillin 0.07 - 0.10

[0181] The gelatin capsules, suitable for direct consumption, were manufactured according to WO 2004 / 050069 and had a diameter of 5 mm and a weight ratio of core material to shell material of 90:10. The capsules opened in the mouth in less than 10 seconds and dissolved completely in less than 50 seconds. APPLICATION EXAMPLE 9 Carbonated beverage (Flavor: Cola) A: sugary drink (comparison drink) B: low-calorie drink C: low-calorie drink D: low-calorie drink E: low-calorie drink ingredient A (in percent by weight) B (in percent by weight) C (in percent by weight) D (in percent by weight) E (in percent by weight) Phosphoric acid 85 0,635 0,635 0,635 0,635 0,635 Citric acid, anhydrous 0,064 0,064 0,064 0,064 0,064 caffeine 0,064 0,064 0,064 0,064 0,064 sucrose 63,60 - - - 12,9 Sucralose - 0,126 - - - Erythritol - - 6,000 - - Aspartam - - 0,350 - 0,07 Stevioside - - - 0,300 - Acesulfame K - - - - 0,07 Sugar coloring 0,800 0,800 0,800 0,800 0,800 Beverage emulsion, type Cola 1,445 1,445 1,445 1,445 1,445 Sodium benzoate 0,106 0,106 0,106 0,106 0,106 Hesperetin dihydrochalcone (I) 0.5% in 1,2-propylene glycol - 1,0 1,0 1,0 1,0 Water ad 100

[0182] The solid components or ingredients are mixed individually with water, combined, and then topped up to 100 g with water. The resulting concentrate is then left to mature overnight at room temperature. Finally, 1 part concentrate is mixed with 5 parts carbonated water, bottled, and sealed.

[0183] Furthermore, the following points will be disclosed: 1. Use of hesperetin dihydrochalcone (I) (3-(3-Hydroxy-4-methoxy-phenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one) or - a salt of hesperet dihydrochalcone (I) or a mixture containing or consisting of several salts of hesperet dihydrochalcone (I) or - a mixture containing or consisting of hesperet dihydrochalcone (I) and a salt or several salts of hesperet dihydrochalcone (I), for (i) Masking, reducing or suppressing an unpleasant taste sensation, preferably a bitter and / or sour and / or astringent taste sensation of unpleasant-tasting substances or mixtures of substances, and in particular of bitter and / or sour and / or astringent-tasting substances or mixtures of substances, and in particular the bitter taste sensation of bitter-tasting substances and / or (ii) Modulating taste sensations selected from the group consisting of cooling, umami, fruity and spicy notes from cooling, umami, fruity or spicy tasting substances or mixtures of substances. 2. Use as defined in point 1, wherein compound (I) also simultaneously intensifies the sweet taste sensation of sweet-tasting substances or mixtures of substances or of substances that taste both sweet and bitter. 3. Use as defined in point 1 or 2, in an aroma composition or in a preparation selected from the group consisting of (1) Preparations intended for nutrition, dietary supplementation, oral hygiene or enjoyment, (2) cosmetic preparations, (3) pharmaceutical preparations intended for oral administration, (4) Flavouring mixtures for use in any of the preparations referred to in (1) to (3), (5) Semi-finished products for the manufacture of any of the preparations referred to in points 1 to 3. 4. Aroma composition containing a compound of formula (I) or a salt of the compound of formula (I) or a mixture containing or consisting of several salts of the compound of formula (I) or a mixture containing or consisting of the compound of formula (I) and a salt or several salts of the compound of formula (I). 5. The aroma composition of point 4, comprising: (a) a compound of formula (I) or a salt of the compound of formula (I) or a mixture comprising or consisting of a plurality of salts of the compound of formula (I) or a mixture comprising or consisting of the compound of formula (I) and a salt or a plurality of salts of the compound of formula (I); and at least one or more of the substances selected from the group consisting of substance(s) (c) and (d) or mixtures thereof, wherein - Substance(s) (c) means one or more unpleasant-tasting substances, preferably bitter, sour and / or astringent-tasting substances, in particular bitter-tasting substances. - Substance(s) (d) means one or more substances that taste both sweet and unpleasant, especially bitter; and / or (b) one or more sweet-tasting substances and may include: (e) one or more substances for masking or reducing an unpleasant taste, in particular a bitter taste, and / or (f) one or more other substances to enhance a sweet taste his impression, and / or (g) one or more substances for masking or reducing a metallic, chalky, acidic or astringent taste, and / or (h) one or more substances with a taste sensation selected from the group consisting of cooling, umami, fruity and savory taste sensations or mixtures thereof; wherein components (b)-(h) do not include hesperetindihydrochalcone (I) or a salt of hesperetindihydrochalcone (I). 6. The flavor composition according to point 5, wherein the total amount of component (a) is sufficient to enhance - preferably synergistically - the sweet taste of the sweet-tasting substance compared to an otherwise equivalent composition without hesperet dihydrochalcone (I) and / or its salt(s), and wherein the total amount of hesperetin dihydrochalcone (I) and / or salt(s) thereof is sufficient to reduce and / or mask the unpleasant taste of the bitter, sour and / or astringent tasting substance(s). 7. The flavor composition according to point 5 or 6, wherein the total amount of hesperet dihydrochalcone (I) and / or its salt(s) is sufficient to modulate the taste impressions of the components (h). 8. The aroma composition according to one of points 5-7, wherein - the sweet-tasting substance (b) is selected from the group consisting of vanillin, ethyl vanillin, ethyl vanillin isobutyrate (=3-ethoxy-4-isobutyryloxybenzaldehyde), furaneol® (2,5-Dimethyl-4-hydroxy-3(2H)-furanon) und Derivaten davon, Homofuronol (2-Ethyl-5-methyl-4-hydroxy-3(2H)-furanon und 5-Ethyl-2-methyl-4-hydroxy-3(2H)-furanon), Maltol und seine Derivate, Cumarin und seine Derivate, gamma-Lactone, delta-Lactone, Methylsorbat, Divanillin, 4-Hydroxy-2(oder 5)-ethyl-5(oder 2)-methyl-3(2H)-furanon, 2-Hydroxy-3-methyl-2-cyclopentenone, 3-Hydroxy-4,5-dimethyl-2(5H)-furanon, Fruchtsäureester und Fruchtlactone 4-(p-Hydroxyphenyl)-2-butanon, 1,1-Dimethoxy-2,2,5-trimethyl-4-hexan, 2,6-dimethyl-5-hepten-1-al, Phenylacetaldehyd, Saccharose, Trehalose, Lactose, Maltose, Melizitose, Raffinose, Palatinose, Lactulose, D-Fructose, D-Glucose, D-Galactose, L-Rhamnose, D-Sorbose, D-Mannose, D-Tagatose, D-Arabinose, L-Arabinose, D-Ribose, D-Glyceraldehyd, Erythrit, Threitol, Arabitol, Ribitol, Xylitol, Sorbitol, Mannitol, Dulcitol und Lactitol; und / oder - the unpleasant-tasting substance (c) is selected from the group consisting of xanthine alkaloids, xanthines, alkaloids, phenolic glycosides, flavonoid glycosides, chalcones or chalcone glycosides, hydrolyzable tannins, non-hydrolyzable tannins, flavones, other polyphenols, terpenoid bitter substances, absinthin from wormwood, amarogentin from gentian, metal salts, pharmaceutically active ingredients: fluoroquinolone antibiotics, beta-lactam antibiotics, ambroxol, propylthiouracil [PROP], aspirin (acetylsalicylic acid), salicin, paracetamol (acetaminophen), ibuprofen, naproxen, ambroxol, guafenesin, omeprazole, pantoprazole, dextromorphane or quinine, vitamins, denatonium benzoate or other denatonium salts, Sucralose octaacetate, urea, unsaturated fatty acids, amino acids and peptides; and / or - the substance (d), which tastes both sweet and unpleasant, is selected from the group consisting of steviol glycosides, rubusoside, dulcoside, mogroside, phyllodulcin, glycyrrhetinic acid or extracts of Stevia ssp., Luo Han Guo, Rubus suavissimus, Hydrangea dulcis, Mycetia balansae, Glycyrrhyza glabra, Magap, sodium cyclamate, acesulfame K, neohesperidin dihydrochalcone, naringin hydrochalcone, saccharin, saccharin sodium salt, aspartame, superaspartame, neotame, alitame, sucralose, lug-duname, carrelame, sucrononate and sucrooctate; and / or - the substance(s) for masking or reducing a bitter taste impression are selected from the group consisting of sodium salts, homoeriodictyol or its sodium salts, eriodictyol, matairesinol, lariciresinol, naringenin, phloretin, 5-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-7-methoxychroman-2-one, 5,7-dihydroxy-4-(4-hydroxyphenyl)-chroman-2-one, 5,7-dihydroxy-4-(4-hydroxy-3-methoxyphenyl)-chroman-2-one and 2,4-dihydroxybenzoic acid vanillylamide; and / or - the substances (f) to enhance a sweet taste sensation are selected from the group consisting of hesperetin, phloretin, rubusoside, fermented rubus extract according to EP 2,954,785-A1, naringenin, balansin A, balansin B and phyllodulcin. 9. A preparation selected from the group consisting of (1) a preparation for nutrition, a food supplement preparation or a preparation for oral care or enjoyment, (2) a cosmetic preparation, (3) a pharmaceutical preparation intended for oral administration, (4) a flavoring mixture for use in any of the preparations mentioned in (1) to (3) and (5) a semi-finished product for the manufacture of one of the preparations referred to in (1) to (3), the preparation includes the aroma composition defined in points 4 to 8. 10. Preparation according to point 9, selected from the group consisting of (1) a preparation for nutrition, a food supplement preparation or a preparation for oral care or enjoyment, (2) a cosmetic preparation, (3) a pharmaceutical preparation intended for oral administration, wherein the preparation (1), (2) or (3) contains, based on its total weight, 0.00001 wt% (0.1 ppm) - 0.005 wt% (50 ppm) of (i) hesperet dihydrochalcone (I) and (ii) its salts (component (a)). 11. Preparation according to point 9, wherein the preparation (1), (2) or (3) contains, on a weight basis, 0.00005 wt% (0.5 ppm) - 0.003 wt% (30 ppm) of (i) hesperet dihydrochalcone (I) and (ii) its salts (component (a)). 12. The preparation described in point 9, selected from the group consisting of (4) a flavoring mixture for use in any of the preparations referred to in (1) to (3) and (5) Semi-finished products for the manufacture of any of the preparations referred to in point 9, wherein the preparation (5) contains, based on its total weight, 0.0001 wt.% to 95 wt.% (i) hesperetin dihydrochalcone (I) and (ii) its salts (component (a)). 13. Method for producing a flavoring composition according to points 5-8 or a preparation according to points 9-12, comprising the steps (1) Provision of the following components: (a) Hesperetin dihydrochalcone (I) or a salt of hesperetin dihydrochalcone (I) or a mixture comprising or consisting of a plurality of salts of hesperetin dihydrochalcone (I) or a mixture comprising or consisting of hesperetin dihydrochalcone (I) and a salt or a plurality of salts of hesperetin dihydrochalcone (I), and at least one or more of the substances selected from the group consisting of substances (c) and (d) or mixtures thereof, wherein - Substance(s) (c) means one or more unpleasant-tasting substances, preferably bitter, sour and / or astringent-tasting substances, in particular bitter-tasting substances. - Substance(s) (d) means one or more substances that taste both sweet and unpleasant, especially bitter; and / or (b) one or more sweet-tasting substances and / or (e) one or more substances for masking or reducing an unpleasant taste, in particular a bitter taste, and / or (f) one or more additional substances to enhance a sweet taste sensation, and / or (g) one or more substances for masking or reducing a metallic, chalky, acidic or astringent taste, and / or (h) one or more substances with a taste sensation selected from the group consisting of cooling, umami, fruity and savory taste sensations or mixtures thereof; wherein components (b)-(h) do not include hesperet dihydrochalcone (I) or a salt of hesperet dihydrochalcone (I) and, (2) Mixing components (a), (b), (c) and / or (d) with the other components. 14. Method for masking, reducing or suppressing an unpleasant, preferably bitter, sour and / or astringent taste impression of unpleasant-tasting substances or mixtures of substances, in particular a bitter taste impression of bitter-tasting substances or mixtures of substances, and / or Selected for modulating taste impressions from the group of cooling, umami, fruity and spicy notes of cooling, umami, fruity or spicy tasting substances or mixtures of substances, and / or simultaneously to intensify the sweet taste impression of sweet-tasting substances or mixtures of substances, or of both sweet and bitter-tasting substances or mixtures of substances with the following step - Mixing the following components (a) Hesperet dihydrochalcone (I) or a salt of hesperet dihydrochalcone (I) or a mixture comprising or consisting of several salts of hesperet dihydrochalcone (I) or a mixture comprising or consisting of hesperet dihydrochalcone (I) and a salt or several salts of hesperet dihydrochalcone (I), and at least one or more of the substances selected from the group consisting of substance(s) (c) and (d) or mixtures thereof, wherein - Substance(s) (c): one or more unpleasant-tasting substances, preferably bitter, sour and / or astringent substances, in particular bitter-tasting substances, means - Substance(s) (d): one or more substances that taste both sweet and unpleasant, especially bitter-tasting substances, means and / or (b) one or more sweet-tasting substances and, if necessary, further components wherein components (b)-(d) do not contain hesperet dihydrochalcone (I) or a salt of hesperet dihydrochalcone (I) and, wherein the total amount of component (a) in the mixture is sufficient to mask, reduce or suppress an unpleasant taste sensation, preferably a bitter, sour and / or astringent taste sensation of unpleasant tasting substances or mixtures of substances, in particular a bitter taste sensation of bitter tasting substances, and / or for modulating taste impressions, selected from the group of cooling, umami, fruity and spicy notes of cooling, umami, fruity or spicy tasting substances or mixtures of substances. and at the same time to intensify the sweet taste impression of sweet-tasting substances or mixtures of substances, or of both sweet and bitter-tasting substances or mixtures of substances - preferably synergistically. 15. Method according to point 14, wherein the total amount of component (a) in the mixture is sufficient to - to mask, reduce or suppress an unpleasant taste sensation, preferably a bitter, sour and / or astringent taste sensation from unpleasant-tasting substances or mixtures of substances, in particular a bitter taste sensation from bitter-tasting substances, and - for modulating taste impressions, selected from the group of cooling, umami, fruity and spicy notes of cooling, umami, fruity or spicy tasting substances or mixtures of substances. and - to enhance - preferably synergistically - the sweet taste of the sweet-tasting substance, and and - to intensify the sweet taste impression of a substance or mixture of substances that tastes both sweet and unpleasant, especially bitter - preferably synergistically - and to reduce or modify the unpleasant, especially bitter, taste impression of the substance or mixture of substances that tastes both sweet and unpleasant, especially bitter. QUOTES INCLUDED IN THE DESCRIPTION

[0000] This list of documents cited by the applicant was automatically generated and is included solely for the reader's convenience. The list is not part of the German patent or utility model application. The DPMA accepts no liability for any errors or omissions. Cited patent literature

[0000] WO 2007 / 014879 A1

[0012] WO 2007 / 107596 A1 [0012, 0035] US 2004 / 0142084

[0023] US 3,924,017 [0023, 0025] WO 2006 / 087991

[0024] WO 98 / 20753

[0025] DE 2148332 A1

[0059] EP 2,954,785-A1 [0099, 0100, 0101, 0102, 0103, 0104, 0105, 0106, 0110, 0131, 0132, 0133, 0183] EP 2008530 A1

[0109] WO 2007 / 014879 [0110, 0145] WO 2007 / 003527 [0110, 0145] WO 2006 / 106023 [0110, 0145] DE 10 2009 002 268.6

[0110] WO 2007 / 107596 [0110, 0145] EP 1 955 601 A1 [0110, 0145] WO 2004 / 078302 [0110, 0145] EP 2,253,226

[0110] EP 2,353,403 B1

[0110] EP 1 258 200

[0145] WO 2006 / 024587

[0145] WO 2006 / 058893

[0145] WO 2005 / 096841

[0145] US 2008 / 0227867 A1

[0145] US 60 / 944,854

[0145] WO 2008 / 046895

[0145] EP 1 989 944 A1

[0145] WO 2012 / 146584 A1

[0145] US 2013 078192 A1

[0145] US 2013 084252 A1

[0145] EP 2,570,035

[0145] EP 2,725,026

[0145] EP 2,570,036

[0145] US 60 / 984,023

[0145] US 61 / 061,273

[0145] WO 2004 / 050069

[0181] Zitierte Nicht-Patentliteratur

[0000] Journal of the American Dietetic Association 2004, 104 (2), 255-275

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[0015] http: / / de.wikipedia.org / wiki / Miracul

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[0032] Yamada A. et al. (1985): Chronic toxicity study of dietary Stevia extracts in F344 rats. In: J. Food Hyg. Soc. Japan. Vol. 26, pp. 169-183; Melis, MS (1999): Effects of chronic administration of Stevia rebaudiana on fertility in rats. In: J. Ethnopharmacol. Vol. 67, pp. 157-161

[0087]

Claims

[1] Aroma composition comprising a compound of formula (I) or a salt of the compound of formula (I) or a mixture comprising or consisting of a plurality of salts of the compound of formula (I) or a mixture comprising the compound of formula (I) and a salt or a plurality of salts of the compound of formula (I) or consisting of the compound of formula (I). [2] The aroma composition according to claim 1, comprising: (a) a compound of formula (I) or a salt of the compound of formula (I) or a mixture comprising or consisting of a plurality of salts of the compound of formula (I) or a mixture comprising or consisting of the compound of formula (I) and a salt or a plurality of salts of the compound of formula (I); and at least one or more of the substances selected from the group consisting of substance(s) (c) and (d) or mixtures thereof, wherein - Substance(s) (c) means one or more unpleasant-tasting substances, preferably bitter, sour and / or astringent-tasting substances, in particular bitter-tasting substances. - Substance(s) (d) means one or more substances that taste both sweet and unpleasant, especially bitter. and / or (b) one or more sweet-tasting substances. [3] Aroma composition according to claim 2, further comprising: (e) one or more substances for masking or reducing an unpleasant taste, in particular a bitter taste, and / or (f) one or more additional substances to enhance a sweet taste sensation, and / or (g) one or more substances for masking or reducing a metallic, chalky, acidic or astringent taste, and / or (h) one or more substances with a taste sensation selected from the group consisting of cooling, umami, fruity and savory taste sensations or mixtures thereof; wherein components (b)-(h) do not include hesperetindihydrochalcone (I) or a salt of hesperetindihydrochalcone (I). [4] Aroma composition according to claim 2 or 3, wherein the total amount of component (a) is sufficient to enhance - preferably synergistically - the sweet taste of the sweet-tasting substance compared to an otherwise equivalent composition without hesperet dihydrochalcone (I) and / or its salt(s), and wherein the total amount of hesperetin dihydrochalcone (I) and / or salt(s) thereof is sufficient to reduce and / or mask the unpleasant taste of the bitter, sour and / or astringent tasting substance(s). [5] Aroma composition according to claim 3 or 4, wherein the total amount of hesperetin dihydrochalcone (I) and / or its salt(s) is sufficient to modulate the taste impressions of the components (h). [6] The flavor composition according to any one of claims 2 to 5, wherein - the sweet-tasting substance (b) is selected from the group consisting of vanillin, ethyl vanillin, ethyl vanillin isobutyrate (=3-ethoxy-4-isobutyryloxybenzaldehyde), Furaneol® (2,5-dimethyl-4-hydroxy-3(2H)-furanone) and its derivatives, homofuronol (2-ethyl-5-methyl-4-hydroxy-3(2H)-furanone and 5-ethyl-2-methyl-4-hydroxy-3(2H)-furanone), maltol and its derivatives, coumarin and its derivatives, gamma-lactones, delta-lactones, 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, fruit acid esters and fruit lactones 4-(p-hydroxyphenyl)-2-butanone, 1,1-dimethoxy-2,2,5-trimethyl-4-hexane, 2,6-dimethyl-5-hepten-1-al, phenylacetaldehyde, sucrose, trehalose, lactose, Maltose, melicitose, 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, erythritol, threitol, arabitol, ribitol,Xylitol, sorbitol, mannitol, dulcitol and lactitol; and / or - the unpleasant-tasting substance (c) is selected from the group consisting of xanthine alkaloids, xanthines, alkaloids, phenolic glycosides, flavonoid glycosides, chalcones or chalcone glycosides, hydrolyzable tannins, non-hydrolyzable tannins, flavones, other polyphenols, terpenoid bitter substances, absinthin from wormwood, amarogentin from gentian, metal salts, pharmaceutical agents: fluoroquinolone antibiotics, beta-lactam antibiotics, ambroxol, propylthiouracil [PROP], aspirin (acetylsalicylic acid), salicin, paracetamol (acetaminophen), ibuprofen, naproxen, ambroxol, guafenesin, omeprazole, pantoprazole, dextromorphane or quinine, vitamins, denatonium benzoate or other denatonium salts, Sucralose octaacetate, urea, unsaturated fatty acids, amino acids and peptides; and / or - the substance (d) which tastes both sweet and unpleasant is selected from the group consisting of steviol glycosides, rubusoside, dulcoside, mogroside, phyllodulcin, glycyrrhetinic acid or extracts of Stevia ssp, Luo Han Guo, Rubus suavissimus, Hydrangea dulcis, Mycetia balansae, Glycyrrhyza glabra, Magap, sodium cyclamate, acesulfame K, neohesperidin dihydrochalcone, naringin hydrochalcone, saccharin, saccharin sodium salt, aspartame, superaspartame, neotame, alitame, sucralose, lugdunam, carrelam, sucrononate and sucrooctate. [7] The flavor composition according to any one of claims 3 to 6, wherein - the substances (e) for masking or reducing a bitter taste impression are selected from the group consisting of sodium salts, homoeriodictyol or its sodium salts, eriodictyol, matairesinol, lariciresinol, naringenin, phloretin, 5-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-7-methoxychroman-2-one, 5,7-dihydroxy-4-(4-hydroxyphenyl)-chroman-2-one, 5,7-dihydroxy-4-(4-hydroxy-3-methoxyphenyl)-chroman-2-one and 2,4-dihydroxybenzoic acid vanillylamide; and / or - the substances (f) to enhance a sweet taste sensation are selected from the group consisting of hesperetin, phloretin, rubusoside, fermented rubus extract according to EP 2,954,785-A1, naringenin, balansin A, balansin B and phyllodulcin. [8] A preparation selected from the group consisting of (1) a preparation for nutrition, a food supplement preparation or a preparation for oral care or enjoyment, (2) a cosmetic preparation, (3) a pharmaceutical preparation intended for oral administration, (4) a flavoring mixture for use in any of the preparations mentioned in (1) to (3) and (5) a semi-finished product for the manufacture of one of the preparations referred to in (1) to (3), wherein the preparation comprises the flavor composition defined in claims 1 to 7. [9] Preparation according to claim 8, selected from the group consisting of (1) a preparation for nutrition, a food supplement preparation or a preparation for oral care or enjoyment, (2) a cosmetic preparation, (3) a pharmaceutical preparation intended for oral administration, wherein the preparation (1), (2) or (3) contains, based on its total weight, 0.00001 wt% (0.1 ppm) - 0.005 wt% (50 ppm) of (i) hesperet dihydrochalcone (I) and (ii) its salts (component (a)). [10] Preparation according to claim 8, wherein the preparation (1), (2) or (3) contains, based on its total weight, 0.00005 wt% (0.5 ppm) - 0.003 wt% (30 ppm) of (i) hesperet dihydrochalcone (I) and (ii) its salts (component (a)). [11] Preparation according to claim 8, selected from the group consisting of (4) a flavoring mixture for use in any of the preparations referred to in (1) to (3), and (5) Semi-finished products for the manufacture of one of the preparations referred to in claim 8, wherein the preparation (5) comprises, based on its total weight, 0.0001 wt.% to 95 wt.% (i) hesperet dihydrochalcone (I) and (ii) its salts (component (a)).