BR112020001641B1 - SWEETENER COMPOSITION, USE OF THE COMPOSITION, AND INGERABLE PRODUCT - Google Patents

Abstract

The present invention relates to a sweetener composition comprising neohesperidin dihydrochalcone (NHDC) and gamma-cyclodextrin, to the use of the sweetener composition to sweeten ingestible products, namely food and pharmaceutical products, and to an ingestible product comprising the sweetener composition. Furthermore, the present invention also relates to the use of a composition comprising neohesperidin dihydrochalcone and a cyclodextrin selected from beta-cyclodextrin and gamma-cyclodextrin as a taste masking agent, to a process for masking unpleasant flavors in ingestible products, mainly in products food and pharmaceutical products and ingestible products comprising substances with an unpleasant taste and the composition to mask the taste.

Description

[001] This application claims the benefit of European Patent Application EP 17382503.5 filed on July 27, 2017.

TECHNICAL FIELD

[002] The present invention relates to the field of sweetening and flavor masking, in particular, it relates to sweetening and flavor manufacturing compositions comprising neohesperidin dihydrochalcone.

FUNDAMENTALS OF THE TECHNIQUE

[003] The consumption of foods and drinks sweetened with sugar has been associated with an increased risk of obesity, diabetes and heart disease, in addition to being harmful to oral health. Therefore, nowadays it is generally accepted that the consumption of sucrose, as well as other caloric sweeteners such as glucose, fructose or high fructose corn syrups, should be reduced.

[004] This need to reduce sugar consumption has increased the use of low-calorie sweeteners, such as stevia extract, monk fruit, saccharin, aspartame, acesulfame K, cyclamate, sucralose or neohesperidin dihydrochalcone, among others.

[005] In particular, neohesperidin dihydrochalcone (also known as neohesperidin DC or NHDC) is a well-known low-calorie sweetener that is a derivative of the natural product neohesperidin, a flavanone found in citrus fruits. It is a high-intensity sweetener, being about 1500 times sweeter than sucrose, and is useful for sweetening foods, beverages and pharmaceuticals.

[006] However, the use of high-intensity, low-calorie sweeteners as sugar substitutes involves several challenges, because not only the intensity of sweetness is important, but other organoleptic properties are also required. Thus, it is generally accepted that an ideal sweetener should have a pleasant taste, with an immediate onset and no lingering aftertaste. In fact, the more a sweetener tastes and functions like sucrose, the greater consumer acceptance. On the other hand, it is also desirable, for economic reasons, to achieve the desired sweetness level using the minimum amount of sweetener.

[007] Therefore, for example, although neohesperidin dihydrochalcone is intensely sweet, it has the disadvantage of having a relatively sweet onset of sweetness and a persistent licorice-like flavor, which makes wider use as a sugar substitute difficult.

[008] Several solutions have been proposed to date in the prior art, in order to overcome these disadvantages and improve the flavor profile of low-calorie sweeteners, in particular neohesperidin dihydrochalcone.

[009] A first strategy combines low-calorie sweeteners with caloric sweeteners. Low-calorie sweeteners allow you to reduce caloric sweeteners to a certain extent. On the other hand, the amount of low-calorie sweetener is low enough so that it does not significantly affect the sweetener profile of the resulting sweetener mixture. In this context, neohesperidin dihydrochalcone is a very interesting low-calorie sweetener candidate, as it has very strong synergies with caloric sweeteners. These synergies allow for greater-than-expected caloric sweetener reductions, without compromising the sweetening profile. Naturally, there is an interest and need to further enhance these synergies to further reduce caloric sweeteners.

[0010] A second strategy is to use mixtures of two or more low-calorie sweeteners, since many of these mixtures result in a synergistic effect, so that the desired level of sweetness can be achieved using smaller amounts of sweeteners, resulting in energy savings. costs. Furthermore, some of these mixtures also provide a qualitative synergy, i.e. the taste quality of the mixtures is generally better than that of the individual components, e.g. undesirable flavors can be reduced.

[0011] For example, US patent US4158068 discloses that the use of a mixture of acesulfame-K with other sweeteners, for example with neohesperidin DC, provides a sweet taste more similar to sucrose than when the sweeteners are used individually.

[0012] Furthermore, the European patent application EP0507598-A1 reveals that the combination of neohesperidin DC and sucralose provides synergy and also an improvement in the quality of sweetness.

[0013] In the article Chung HJ, The effect of β-cyclodextrin on the flavor quality of neohesperidin dihydrochalcone, J. Food Sci. Nutr., 1996, 1 (2), 186-189, the effect of beta-cyclodextrin on sweetness and NHDC aftertaste was investigated, and it was concluded that the addition of beta-cyclodextrin reduced the sweetness intensity and NHDC aftertaste. It was found that the intensity of sweetness decreased more quickly than the aftertaste. The author therefore concluded that it was not possible to suppress the aftertaste of NHDC while maintaining the sweet taste using beta-cyclodextrin. In other words, the sweet quality of the resulting mixture was inferior to that of NHDC alone.

[0014] Therefore, there is a need in the art for new high-intensity sweetener compositions with improved characteristics, that is, that are capable of providing the desired sweet taste with the minimum amount of sweetener and with an improved taste quality, free from powders. - flavors and more similar to the taste of sucrose.

[0015] On the other hand, another related problem arises due to the unpleasant taste of various substances frequently found in foods, beverages and pharmaceutical products.

[0016] The main flavors or taste sensations that are normally unpleasant are bitterness, astringency and metallic flavors.

[0017] Only rarely do consumers accept the bitter/astringent taste of foods and drinks, for example in black coffee, black or green tea, beer, red wine, grapefruit products or bitter lemon. In most other cases, these flavors are not desirable and must be eliminated or masked.

[0018] For example, many substances considered healthy and purposefully added to healthy food preparations are, however, adversely perceived in terms of taste by consumers. This may be the case with the bitter taste of certain vitamins, minerals, peptides or protein hydrolysates or the bitter or astringent taste of certain plant-based phenols, flavonoids, isoflavones, terpenes and glucosinolates, which are reported to have positive antioxidant and anticarcinogenic properties. .

[0019] Another example is the bitter taste associated with potassium chloride, which is increasingly being used to provide saltiness to food products, as a healthier substitute for sodium chloride.

[0020] A particularly problematic group of consumables in terms of taste are pharmaceutical products, which often contain active ingredients with a bitter, astringent or metallic taste. This adverse perception may even adversely affect patient compliance, especially in population groups that are particularly sensitive to bad taste, especially children.

[0021] Consequently, since the taste of the consumable product plays an important role in its acceptance by the consumer, efforts have been made to suppress or reduce these unpleasant flavors in consumables, namely in foods, beverages and pharmaceuticals.

[0022] Depending on each particular substance and each particular consumable product, different solutions can be used to mask the taste, as has been widely reported in the prior art, for example, some possible strategies are to partially remove the bitter substances, coat them or microencapsulate them, adding flavors and/or sweeteners or adding specific substances to mask the flavor.

[0023] the use of flavor-masking substances, capable of modulating, reducing or suppressing unpleasant flavors, particularly bitterness, astringency or metallic flavors, has proven to be useful for many particular requests.

[0024] A good number of substances have been reported in the art for use as flavor-masking agents in foods and pharmaceuticals, as reviewed, for example, by Ley JP in the article Masking bitter taste by molecules, Chem. Percept., 2008, 1, 58-77. Among the many flavor-masking substances mentioned are some sweeteners, such as thaumatin and neohesperidin dihydrochalcone; polymers and complexing agents, such as cyclodextrins, poly-Y-glutamic acid and chitosan; neodiosmin; L-ornithine and derivatives such as L-ornityl-β-alanine or L-ornithynyltaurine; various aspartic acid-containing dipeptides, such as L-aspartyl-L-phenylalanine-potassium salt; sodium salts of saturated fatty acids, such as sodium stearate, palmitate and laurate; organic phosphates, phosphonates, vanadates, thiophosphates and bisphosphates; flavanones such as eriodictyol and homoeriodictyol; among many others.

[0025] In particular, neohesperidin dihydrochalcone has been reported as an effective taste-masking substance, for example, it has been used to mask the bitter taste of substances such as paracetamol, dextromethorphan and other pharmaceutical products, as well as in specialty foods, as disclosed in Borrego et. al., Neohesperidin Dihydrochalcone, in: L O’Brien Nabors, eds. Alternative Sweeteners, fourth edition, CRC Press, 2012, 94-95.

[0026] However, achieving an acceptable level of taste masking generally requires the use of considerable amounts of the taste-masking substance, which is unsatisfactory in terms of costs and additional notes.

[0027] Therefore, there is a need in the art for new flavor masking compositions capable of effectively modulating, reducing or suppressing unpleasant flavors and requiring the use of reduced amounts of the flavor masking composition.

BRIEF DESCRIPTION OF FIGURES

[0028] Figure 1 represents the concentrations of neohesperidin dihydrochalcone (NHDC) that are equivalent to 1% and 3% sucrose solutions in water. The abscissa represents the two sweetness levels evaluated, that is, 1% and 3% sucrose solutions, and the ordinate represents the NHDC concentrations necessary to reach these sweetness levels. In successive tests, neohesperidin dihydrochalcone was used alone (NHDC, black circles), in combination with gamma-cyclodextrin (black squares, diamonds, triangles, crosses and straight lines - Ex. A - E) and in combination with beta-cyclodextrin ( gray squares and diamonds). A partial overlap is observed between the lines corresponding to Examples D (NHDC: gCD 1:6) and (NHDC: gCD 1:10).

[0029] Figure 2 is an enlarged section of the graph shown in Figure 1, which further represents the concentrations of neohesperidin dihydrochalcone (NHDC) in combination with gamma-cyclodextrin that are equivalent to 1% and 3% sucrose solutions in water, in a molar ratio NHDC:gamma-cyclodextrin 1:1 (example A, squares), 1:3 (example B, diamonds), 1.5:1 (example C, triangles), 1:6 (example D, crosses) and 1:10 (Example E, straight line, partial overlap with the line corresponding to Example D).

[0030] Figure 3 represents the relative sweetener potency to sucrose of the tested compositions, at different sweetness levels. The ordinate represents the relative sweetener potency and the abscissa represents the sweetness levels, that is, equivalent to 1% and 3% sucrose solutions. The substances tested were: neohesperidin dihydrochalcone alone (NHDC, black circles) and in combination with gamma-cyclodextrin in a molar ratio NHDC:gamma-cyclodextrin 1:1 (example A, squares), 1:3 (example B, diamonds), 1.5:1 (Example C, triangles) and 1:6 (Example D, crosses).

[0031] Figure 4 is a spider diagram representing the organoleptic profile of sucrose (triangles), neohesperidin dihydrochalcone (NHDC, circles) and two compositions comprising NHDC and gamma-cyclodextrin in a molar ratio NHDC:gamma-cyclodextrin 1:1 ( example A, squares) and 1:3 (Example B, diamonds). The sensory descriptors evaluated were total sweetness, time to detect the first sweetness, time to maximum sweetness, menthol/licorice flavor and mouthfeel, on a scale of 0 to 5 points.

[0032] Figure 5 represents the 1H-NMR spectrum in D2O at 400 MHz of the complex from Example A, with a molar ratio of 1:1 NHDC: gamma-cyclodextrin.

[0033] Figure 6 represents the 1H-NMR spectrum in D2O at 400 MHz of gamma-cyclodextrin.

[0034] Figure 7 represents the 1H-NMR spectrum in deuterated DMSO at 400 MHz of NHDC.

[0035] Figure 8 schematically represents a glucopyranose ring that is part of the gamma-cyclodextrin structure, in which the protons as described in the 1H NMR spectrum are identified.

[0036] Figure 9 schematically represents the aglycone part of the neohesperidin dihydrochalcone structure, in which the protons as described in the 1H NMR spectrum are identified.

OBJECT OF THE INVENTION

[0037] In a first aspect, the present invention relates to a sweetener composition comprising neohesperidin dihydrochalcone and gamma-cyclodextrin.

[0038] A second aspect of the invention relates to the use of a composition comprising neohesperidin dihydrochalcone and a cyclodextrin selected from beta-cyclodextrin and gamma-cyclodextrin as a taste masking agent.

[0039] Another aspect of the invention relates to the use of the sweetener composition to sweeten ingestible products.

[0040] Another aspect of the invention relates to an ingestible product comprising the sweetener composition.

[0041] A further aspect of the invention relates to an ingestible product comprising an unpleasant-tasting substance and a taste-masking composition comprising neohesperidin dihydrochalcone and a cyclodextrin selected from beta- and gamma-cyclodextrin.

DETAILED DESCRIPTION OF THE INVENTION

[0042] In a first aspect, the present invention relates to a sweetener composition comprising neohesperidin dihydrochalcone and gamma-cyclodextrin.

[0043] In a second aspect, the invention relates to the use of a composition comprising neohesperidin dihydrochalcone and a cyclodextrin selected from beta-cyclodextrin and gamma-cyclodextrin as a taste-masking agent.

[0044] The authors of the present invention have developed a new sweetener composition comprising the combination of neohesperidin dihydrochalcone (NHDC) and gamma-cyclodextrin which, surprisingly, provides an excellent synergistic effect, thus achieving the desired level of sweetness using less amount of NHDC. Furthermore, not only is the sweetness intensity synergistically increased, but also the sweetness quality of the combination is notably superior to using NHDC alone, for example, the lingering aftertaste is greatly reduced and the onset time is also shortened, providing thus a better overall flavor profile, more similar to that provided with sucrose.

[0045] Furthermore, it has also been surprisingly discovered that compositions comprising the combination of NHDC with beta-cyclodextrin or gamma-cyclodextrin show strong taste-masking synergy, that is, the taste-masking effect obtained with the combination, typically to mask bitter or astringent flavors, is greater than the sum of the effects of each individual substance.

[0046] Throughout this description, as well as in the claims, singular forms, generally preceded by "a", "an" or "the(s)", should be interpreted to also include the plural, unless the context clearly indicates otherwise.

[0047] As used herein, the term "about" used before a quantitative value should be interpreted as including the specific quantitative value and also a variation of no more than ± 10% of the given value, preferably no more than ± 5 % of value given value.

Neohesperidin dihydrochalcone

[0048] Neohesperidin dihydrochalcone (CAS number 20702-77-6) is a well-known synthetic intense sweetener, sometimes abbreviated as neohesperidin DC or NHDC. It is also known by its chemical name 1-[4-[[2-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2,6-dihydroxyphenyl]-3- (3-hydroxy-4-methoxyphenyl)propan-1-one.

[0049] Structurally, it is an analogue of neohesperidin, a bitter flavanone that occurs in citrus fruits. NHDC can be synthesized from naringin, obtained from grapes (Citrus paradisi) or from neohesperidin, which can be extracted from bitter orange (Citrus aurantium), as reviewed, for example, in Borrego et al., Neohesperidin Dihydrochalcone , in: L O'Brien Nabors, eds. Alternative Sweeteners, fourth edition, CRC Press, 2012, 117-131.

[0050] Furthermore, NHDC is widely available commercially, for example, from the company Interquim SA, or Ferrer HealthTech.

Cyclodextrin

[0051] Cyclodextrins are cyclic oligosaccharides derived from starch. The cyclic structure of cyclodextrins is generally described as having a conical or torus-shaped shape, in which the primary and secondary hydroxyl groups are oriented outward, while the nonpolar hydrogens and ether-like oxygens are on the interior of the molecule. thus forming a hydrophilic external surface and a non-polar and hydrophobic internal cavity.

[0052] As a result of this three-dimensional structure, cyclodextrins are capable of acting as hosts to form inclusion complexes with a wide variety of guest molecules, generally hydrophobic molecules or molecules comprising a hydrophobic part. In these inclusion complexes, the guest molecule is held, at least in part, within the hydrophobic cavity of the cyclodextrin host molecule.

[0053] In particular, gamma-cyclodextrin (y-cyclodextrin, CAS number 17465-86-0), also known as cyclo-malto-octaose or cyclo-octa-amylose, is a cyclodextrin containing 8 α-D-glucopyranosyl units linked to (1 ^ 4).

[0054] Gamma-cyclodextrin can be obtained from starch by the action of the enzyme cyclodextrin glycosyltransferase (CDTGase; ED 2.4.1.19), for example, as disclosed in Hedges A, Cyclodextrins: Properties and Applications, In: Starch. Chemistry and Technology, BeMiller J and Whistler R., eds., Food Science and Technology International Series, Third Edition, Elsevier, 2009, 833-851.

[0055] Gamma-cyclodextrin is readily available from several commercial sources, for example, from the companies Wacker Chemie and Roquette.

[0056] Beta-cyclodextrin (β-cyclodextrin, CAS number 7585-399), also known as beta-cyclo-amylose, beta-dextrin, betadexum, cyclohepta-amylose, cyclohepta-glucan or cyclo-malto- heptose, is a cyclodextrin containing 7 α-D-glucopyranosyl units linked to (1^4).

[0057] Beta-cyclodextrin can be obtained from starch by the action of the enzyme cyclodextrin glycosyltransferase (CDTGase; ED 2.4.1.19), for example, as disclosed in Hedges A, Cyclodextrins: Properties and Applications, In: Starch. Chemistry and Technology, BeMiller J and Whistler R., eds., Food Science and Technology International Series, Third Edition, Elsevier, 2009, 833-851.

[0058] Beta-cyclodextrin is readily available from several commercial sources, for example, from the companies Wacker Chemie and Roquette.

Sweetener composition

[0059] The sweetener composition of the present invention comprises neohesperidin dihydrochalcone and gamma-cyclodextrin.

[0060] This sweetener composition is intended to include a simple mixture of neohesperidin dihydrochalcone and gamma-cyclodextrin, as well as when both components are in the form of a complex.

[0061] In one embodiment, the sweetener composition is a mixture of both components.

[0062] The composition according to this embodiment can be prepared by simply dry mixing NHDC and gamma-cyclodextrin using any suitable mixing means, for example, using a rotary mixer or agitator mixer.

[0063] In another embodiment of the invention, NHDC and gamma-cyclodextrin are in the form of a complex.

[0064] In this complex, the NHDC is presumably inserted, at least partially, into the gamma-cyclodextrin cavity, forming an inclusion complex. However, the term "complex", within the meaning of the present invention, is intended to include other possible variations, involving other non-stoichiometric interactions between NHDC and gamma-CD to form the supramolecular complex.

[0065] This complex is typically prepared by dissolving gamma-cyclodextrin in a suitable solvent, preferably in water, and subsequently adding NHDC to the solution and isolating the complex from the solution.

[0066] The concentration of gamma-cyclodextrin in the solution is generally between 1-20% w/v, preferably between 5-10% w/v. NHDC is added to this solution in an amount according to the desired NHDC:gamma-cyclodextrin molar ratio in the complex.

[0067] The mixture is generally stirred until complete dissolution, typically for a period of time comprised between 10 minutes and 3 hours, at a temperature generally comprised between 20°C and 60°C, preferably comprised between 20°C and 25° W.

[0068] To isolate the solid complex, the solvent is removed by any suitable method, for example, by freeze-drying, or it can be evaporated under reduced pressure.

[0069] The NHDC:gamma-cyclodextrin molar ratio in the sweetener composition of the present invention is generally between 1.5:1 and 1:10, preferably between 1.5:1 and 1:6, more preferably between 1. 2:1 and 1:4, even more preferably between 1.1:1 and 1:3.5 and even more preferably between 1:1 and 1:3.

[0070] In a preferred embodiment of the present invention, the NHDC:gamma-cyclodextrin molar ratio is about 1:1.

[0071] In another preferred embodiment, the NHDC:gamma-cyclodextrin molar ratio is about 1:3.

[0072] The compositions of the present invention provide an exceptional synergistic effect, so that, surprisingly, gamma-cyclodextrin strongly increases the sweetness of NHDC. Thus, for example, as disclosed in Example 3 (Table 3), in a sensory test carried out with a calibrated panel, it was observed that 5 ppm of NHDC are needed to achieve a level of sweetness equivalent to a 1% sucrose solution. in water when NHDC is used alone. On the other hand, when used in combination with gamma-cyclodextrin, significantly smaller amounts of NHDC are needed to achieve the same effect (only 3.5-3.9 ppm in Ex. A-E). Similarly, 24 ppm of NHDC is required to achieve a level of sweetness equivalent to a 3% sucrose solution in water when NHDC is used alone, whereas when used in combination with gamma-cyclodextrin again, significantly smaller amounts are required. of NHDC (only 12.2-13.5 ppm in Ex. A-E).

[0073] Furthermore, surprisingly, for compositions comprising beta-cyclodextrin rather than gamma-cyclodextrin, exactly the opposite effect is observed (see Comparative Examples A and B in Table 3), i.e., larger amounts of NHDC are required , in relation to the use of NHDC alone, for achieving the same level of sweetness (for example, 6.1 ppm and 7.7 ppm of NHDC in the composition vs. 5 ppm of NHDC alone, to obtain 1% sucrose sweetness; and 28.8 ppm and 28.3 ppm of NHDC in the composition versus 24 ppm of NHDC alone, to achieve 3% sucrose sweetness level.

[0074] The strong sweetness synergy obtained with the sweetener composition of the present invention, comprising gamma-cyclodextrin and NHDC, can also be observed in the graphs of Figures 1 and 2.

[0075] Furthermore, a quantitative calculation of this synergistic effect is also provided (Example 3, Tables 5 and 6). It can be seen that the compositions of the present invention show remarkable synergy in sweetness, i.e. greater than 15% for a 1% sucrose sweetness level, preferably in the range of 18% to 40% for a sucrose sweetness level. at 1%, particularly 29.9% and 38.9% for the sweetness level of 1% sucrose for a 1:1 and 1:3 molar ratio composition of NHDC to gamma-cyclodextrin, respectively; and a sweetness synergy greater than 60% for the 3% sucrose sweetness level, preferably in the range of 60% to 95%, particularly 76.5% and 92.3% sweetness synergy for the 3% sucrose sweetness level. 3% sucrose, for a composition with a 1:1 and 1:3 molar ratio of NHDC to gamma-cyclodextrin, respectively. On the other hand, the compositions of the comparative examples, containing beta-cyclodextrin, show negative synergies, that is, the combination shows a suppressive sweetness effect.

[0076] This suppressive effect of beta-cyclodextrin on the sweetness of NHDC is in accordance with the prior art, as disclosed, for example, in the article Chung H.J., The effect of β-cyclodextrin on the taste quality of neohesperidin dihydrochalcone, J. Food Sci. Nutr., 1996, 1 (2), 186-189.

[0077] Another quality of the sweetening compositions of the present invention is that their relative sweetening potency decreases less markedly with increasing sweetness levels, compared to NHDC alone.

[0078] The relative sweetener potency of a given compound, at a given sweetness level, indicates how many times sweeter that compound is than sucrose and can be calculated as the ratio between the sucrose concentration and the equisweet concentration of the compound .

[0079] A test was carried out to evaluate the evolution of the relative potency of the sweetener of the compositions of the present invention (Example 4). The results show (Table 7) that, while with NHDC alone the sweetener potency relative to sucrose decreases rapidly with the sweetness level, the sweetener potency of the sweetener compositions of the present invention shows a notably slower decrease. This effect can be better appreciated in Figure 3.

[0080] Another advantage of the sweetener composition of the present invention is that it provides an overall flavor profile that is closer to sucrose than the flavor profile of NHDC alone. The flavor profiles of sucrose, NHDC and two compositions according to the present invention were tested (Example 5) using each sample at concentrations equal to 3% sucrose. The following sensory parameters were evaluated on a 0 to 5 point scale by a calibrated taste panel: time to first sweetness (or onset period, i.e. the period preceding the onset of sweetness), time to maximum sweetness (i.e., the period preceding the maximum perception of sweetness), prolonged time (i.e., the period of disappearance of sweetness), menthol/licorice flavor (i.e., the perception of any flavor other than sweetness, i.e. flavors of menthol and/or licorice) and mouthfeel (described as density, i.e. the viscosity perceived in the mouth).

[0081] The results obtained, as listed in Table 8 of Example 5, show that the flavor profile of NHDC is notably different from the target sucrose profile, having longer times for the first detection of sweetness and to reach maximum sweetness, the persistence is also longer, is associated with notable off flavors and mouthfeel is lower.

[0082] Conversely, the sweetening agent of the present invention has a flavor profile closer to the flavor profile of sucrose. Thus, compared to NHDC, times to initial and maximum sweetness are reduced, lingering and off-flavors are also reduced, while mouthfeel is improved.

[0083] Figure 4 shows the results of this comparative taste test in the form of a spider chart. This graph clearly illustrates how gamma-cyclodextrin approximates the flavor profile of NHDC to that of sucrose. The best results in terms of flavor profile are obtained with Example B, which contains a 1:3 NHDC:gamma-cyclodextrin molar ratio.

Use as a sweetening agent

[0084] Due to the observed sweetening synergy and the improved overall flavor profile provided, the sweetener composition of the present invention is particularly suitable for sweetening all types of ingestible products.

[0085] Therefore, in an additional aspect, the present invention relates to the use of the above-defined composition to sweeten an ingestible product.

[0086] In a further aspect, the present invention relates to a method of sweetening an ingestible product comprising the step of adding the sweetener composition defined above to the ingestible product. Typically, an effective amount of the sweetening composition is added.

[0087] The term "ingestible product", within the meaning of the present invention, refers broadly to any sweetening substance intended to be ingested orally, by a human or by an animal, and includes substances that are drunk, eaten , swallowed or otherwise ingested, namely food and pharmaceutical products. Furthermore, the term "ingestible product" should also include substances that should not be ingested but are first ingested into the mouth and subsequently expelled, for example, chewing gum and oral hygiene compositions such as mouthwashes, toothpastes or gels. tooth, for example.

[0088] In one embodiment of the present invention, the ingestible product is selected from the group consisting of food products, pharmaceutical products and oral hygiene compositions; preferably selected from food and pharmaceutical products.

[0089] In another embodiment of the present invention, the ingestible product is a food product.

[0090] In another embodiment of the present invention, the ingestible product is a pharmaceutical product.

[0091] The expression "food product", as used in this document, means any edible product intended for human or animal nutrition and includes solids, semisolids and liquids, also including beverages. The term "food product" also includes products that are intended to be partially ingested and subsequently expelled from the oral cavity, particularly chewing gum.

[0092] Beverages suitable for being sweetened with the composition of the present invention may be, without limitation, any type of sweetener beverage, with or without gas, with or without alcohol, alcoholic or non-alcoholic, and include, among others, soft drinks with fruit flavored soft drinks, soft drinks, sports drinks and, in general, any drink containing and/or flavored with fruits, vegetables, aromatic plants, tea, coffee or cocoa, for example; also includes drinks that contain wine or beer, for example. The beverage category includes ready-to-drink beverages as well as other forms such as powders, granules, tablets or liquid concentrates, which must be reconstituted with water.

[0093] Other food products are, for example, bakery products, such as bread, cakes, cookies, cakes (muffins) and, in general, any type of baked food; also dairy products such as yogurt, drinking yogurt, frozen yogurt, milk, milk-based drinks, condensed milk, cream, cheese or ice cream; soy-based products such as soy milk or soy lecithin; confectionery products such as chocolate, caramels, sweets, marzipan or chewing gum; cereal-type products, such as breakfast cereals, cereal bars, energy/nutrition bars or flakes; fruit products such as jelly, fruit puree, preserved fruit or sauces; vegetable-derived products such as sauces, dried, preserved or frozen vegetables; oil-based products and emulsions, such as mayonnaise and various dressings; among many others.

[0094] The category of food products also includes, in particular, nutritional or dietary supplements, that is, food products enriched in some nutritional ingredients, for example, vitamins, minerals, amino acids, proteins, vegetables, enzymes or other substances intended to supplement the human diet and which can be in any suitable food form, typically as drinks or bars, for example.

[0095] Also included in the term food products are all types of dry products, such as dessert mixes or dry ready meals.

[0096] Food products also include, in particular, any food intended for animal nutrition.

[0097] Pharmaceutical products suitable for sweetening with the composition according to the present invention include formulations containing any medicament for oral administration, for human or veterinary therapy, and include any type of health supplement, as well as, for example, vitamins , minerals and their mixtures. Pharmaceutical products may be in any form suitable for oral administration as are well known to those skilled in the art, for example solid forms such as tablets, chewable tablets, orally disintegrating tablets (ODT), sublingual tablets, orally disintegrating films (films). flash), lozenges, gums or chewable powders; or liquid forms, such as drops, syrups or suspensions; or alternatively, in the form of powders, granules or tablets intended to be dissolved in a liquid to be administered, for example effervescent tablets.

[0098] It is understood that the above examples are non-limiting and any ingestible product that is suitable for being sweetened may be suitable for being sweetened using the composition of the present invention.

[0099] The term "sweetener", as used herein, refers to the common meaning of this term, that is, providing sweet flavor to an edible product. This sweetening effect is understood to encompass modalities in which the sweetening composition is the only source of sweetness present in the product, as well as other alternative modalities in which it is used in combination with other sweeteners.

[00100] Therefore, in one embodiment, the sweetening composition of the present invention is used in combination with other sweetening agents, for example, with other high-intensity sweeteners (low-calorie sweeteners), such as extracts of stevia, monk fruit, acesulfame -K, aspartame, cyclamate, neotame, saccharin, sucralose, thaumatin or mixtures thereof; and/or with carbohydrate sweeteners (caloric sweeteners), such as sucrose, glucose, fructose and mixtures thereof.

[00101] When the sweetened edible product is a food product, particularly for human consumption, the sweetener composition is generally used in combination with a carbohydrate sweetener. In this particular embodiment, the composition is used as a sugar substitute or reducing agent and aims to reduce as much as possible the amount of sugar contained in the food product, without altering the taste of the sugar-like product. In fact, the sweet taste provided by carbohydrate sweeteners is generally the most accepted by consumers, while, in general, the flavor profile of high-intensity sweeteners cannot completely imitate the taste of sugar, namely due to its onset, duration, different mouthfeel and/or flavor.

[00102] Surprisingly, it was found that the use of the composition of the present invention makes it possible to reduce the amount of NHDC necessary to replace a certain proportion of sugar in an ingestible product, namely, in a food product. Thus, for example, as disclosed in Example 6, the present composition was used to sweeten an orange soft drink, to replace part of the content of high fructose corn syrup (HFCS) originally used as a sweetener. It was found that, using NHDC alone, the maximum sugar reduction achieved, without any change in taste being perceived by a calibrated panel, was a 10% reduction from HFCS, using 10 ppm NHDC as a substitute. However, when a composition comprising NHDC and gamma-cyclodextrin according to the present invention was used, the same percentage of sugar substitution was achieved with just 4.5 ppm of NHDC, also without any change in the overall flavor profile.

[00103] Furthermore, the present composition is also effective for increasing the proportion of sugar that can be replaced in a sweetened edible product, without any noticeable change in the flavor profile. Thus, for example, as disclosed in Example 7, using NHDC alone as a sugar substitute, a 15% sucrose reduction in an orange juice-based soft drink was possible, while, using the combination of NHDC and gamma-cyclodextrin, it was possible to reduce the sugar content by up to 25%. Similarly, as disclosed in Example 8, using NHDC alone as a sugar substitute, a 10% reduction in sugar content in a dark chocolate product was possible; however, when the composition of the invention was used as a sugar substitute, it was possible to reduce the sugar content of the chocolate product by up to 28%.

[00104] Therefore, the composition of the present invention, comprising NHDC and gamma-cyclodextrin, improves the sugar substitution efficiency of NHDC, that is, for a given proportion of sugar to be replaced, it allows the use of a smaller amount of NHDC and Furthermore, it also allows substituting larger proportions of sugar in an edible product without noticeable variation in taste than when using NHDC alone.

[00105] In one embodiment of the invention, the sweetener composition is used as a sugar replacement agent. As used herein, sugar is intended to encompass any suitable carbohydrate sweetener, for example, sucrose, glucose, fructose and mixtures thereof.

[00106] The percentage of sugar that is replaced by the sweetener varies depending on the specific food product. For example, the percentage of substituted carbohydrate sweetener is typically in the range of 5-60%, preferably in the range of 10-30%, where the percentage refers to the weight of the substituted carbohydrate sweetener relative to the original total carbohydrate content. .

[00107] Typically, using the composition to sweeten an ingestible product involves adding the composition to the ingestible product.

[00108] The sweetening composition of the invention can be added to the ingestible product in a conventional manner, analogously to usual sweetening agents. For example, it can be added to a pharmaceutical product together with other pharmaceutical excipients, or it can be added to food products by incorporating it at some stage of the manufacturing process, as is well known to those skilled in pharmaceutical technology or food technology.

[00109] In an alternative embodiment, the sweetener composition can be generated in situ, so that both components, i.e., NHDC and gamma-cyclodextrin, can be added separately, preferably consecutively, during the manufacture of the ingestible product, typically followed by a complete mixture.

[00110] In a further aspect, the present invention relates to a process of sweetening an ingestible product comprising adding the sweetener composition defined above to the ingestible product.

[00111] In a further aspect, the present invention also relates to a sweetened ingestible product comprising the sweetener composition defined above.

[00112] The amount of the sweetening composition used to sweeten the ingestible product or included in the sweetened ingestible product must be an "effective amount" to sweeten it, that is, to provide sweet flavor to the ingestible product. This "effective amount" varies greatly depending on the specific product as well as the degree of sweetness desired. Those skilled in the art can easily establish the appropriate amount of the composition to be added to the ingestible product depending on the particular case.

[00113] For example, the amount of the sweetening composition used to sweeten the ingestible product, or contained in the sweetened ingestible product, may be in the range of 1-5000 ppm, preferably in the range of 1-500 ppm, more preferably in the range of 1 -200 ppm, in relation to the total weight of the ingestible product. The total weight of the ingestible product must also include the weight of the added sweetening composition.

[00114] Aspects of the present invention related to the sweetener composition comprising NHDC and gamma-cyclodextrin can be defined according to the following modalities: 1. Sweetener composition comprising neohesperidin dihydrochalcone and gamma-cyclodextrin. 2. Sweetener composition, according to modality 1, characterized by being a mixture of neohesperidin dihydrochalcone and gamma-cyclodextrin. 3. Sweetener composition, according to embodiment 1, characterized in that neohesperidin dihydrochalcone and gamma-cyclodextrin are in the form of a complex. 4. Sweetener composition, according to any one of embodiments 1 to 3, characterized in that the molar ratio neohesperidin dihydrochalcone: gamma-cyclodextrin is between 1.5:1 and 1:10. 5. Composition, according to any of modalities 1 to 4, characterized in that the molar ratio neohesperidin dihydrochalcone: gamma-cyclodextrin is between 1.5:1 and 1:6. 6. Composition, according to modality 5, characterized by the molar ratio neohesperidin dihydrochalcone: gamma-cyclodextrin being between 1.2:1 and 1:4. 7. Composition, according to embodiment 6, characterized by the molar ratio neohesperidin dihydrochalcone: gamma-cyclodextrin being between 1.1:1 and 1:3.5. 8. Composition, according to modality 7, characterized by the molar ratio neohesperidin dihydrochalcone: gamma-cyclodextrin being between 1:1 and 1:3. 9. Composition, according to any one of embodiments 1 to 8, characterized in that the molar ratio neohesperidin dihydrochalcone: gamma-cyclodextrin is about 1:1. 10. Composition, according to any one of embodiments 1 to 8, characterized by the molar ratio neohesperidin dihydrochalcone: gamma-cyclodextrin being 1 ± 0.1:1 ± 0.1. 11. Composition, according to modality 10, characterized by the molar ratio neohesperidin dihydrochalcone: gamma-cyclodextrin being 1 ± 0.05:1 ± 0.05. 12. Composition, according to any one of embodiments 1 to 11, characterized by the molar ratio neohesperidin dihydrochalcone: gamma-cyclodextrin being 1:1. 13. Composition, according to any one of embodiments 1 to 8, characterized in that the molar ratio neohesperidin dihydrochalcone: gamma-cyclodextrin is about 1:3. 14. Composition, according to any one of embodiments 1 to 8, characterized by the molar ratio neohesperidin dihydrochalcone: gamma-cyclodextrin being 1 ± 0.1:3 ± 0.3. 15. Composition, according to modality 14, characterized by the molar ratio neohesperidin dihydrochalcone: gamma-cyclodextrin being 1 ± 0.05:3 ± 0.15. 16. Composition, according to any one of embodiments 1 to 15, characterized by the molar ratio neohesperidin dihydrochalcone: gamma-cyclodextrin being 1:3. 17. Use of the composition, according to any one of embodiments 1 to 16, to sweeten an ingestible product. 18. Use, according to embodiment 17, characterized in that the ingestible product is selected between a food product and a pharmaceutical product. 19. Use, according to modality 17 or 18, characterized by the ingestible product being a food product. 20. Use, according to modality 19, characterized by the food product being for human nutrition. 21. Use, according to modality 19, characterized by the food product being for animal nutrition. 22. Use, according to modality 19, characterized in that the food product is a drink. 23. Use, according to embodiment 19, characterized in that the composition is used as a sugar replacement agent. 24. Use, according to any one of embodiments 17 to 23, characterized in that the composition is administered in combination with at least one additional sweetening agent. 25. Use, according to embodiment 24, characterized in that at least one other sweetener is selected from the group consisting of extracts of stevia, monk fruit, acesulfame-K, aspartame, cyclamate, neotame, saccharin, sucralose, thaumatin, sucrose, glucose, fructose and their mixtures. 26. Process for sweetening an ingestible product comprising adding the sweetener composition, according to any one of embodiments 1 to 16, to the ingestible product. 27. Process, according to modality 26, characterized in that the sweetener composition is generated in situ. 28. Process, according to embodiment 27, in which each component of the sweetener composition is added separately during the manufacture of the ingestible product, preferably each component of the sweetener composition is added consecutively during the manufacture of the ingestible product. 29. Process, according to any one of embodiments 26 to 28, characterized in that the sweetener composition is added in an amount comprised between 1 and 5000 ppm, preferably comprised between 1 and 500 ppm, and more preferably comprised between 1 and 200 ppm, in in relation to the total weight of the ingestible product. 30. Process, according to any one of embodiments 26 to 29, characterized in that the ingestible product is selected from a food product and a pharmaceutical product. 31. Process, according to modality 30, characterized by the ingestible product being a food product. 32. Process, according to modality 31, characterized by the food product being for human nutrition. 33. Process, according to modality 31, characterized by the food product being for animal nutrition. 34. Process, according to embodiment 31, characterized in that the food product is a beverage. 35. Ingestible product comprising the sweetener composition, according to any one of embodiments 1 to 16. 36. Ingestible product, according to embodiment 35, characterized in that the sweetening composition is in an amount comprised between 1 and 5000 ppm, preferably comprised between 1 and 500 ppm and more preferably between 1 and 200 ppm, in relation to the total weight of the ingestible product. 37. Ingestible product, according to modality 35 or 36, characterized in that the ingestible product is selected between a food product and a pharmaceutical product. 38. Ingestible product, according to modality 37, characterized by the ingestible product being a food product. 39. Ingestible product, according to modality 38, characterized by the food product being for human nutrition. 40. Ingestible product, according to modality 38, characterized by the food product being for animal nutrition. 41. Ingestible product, according to modality 38, characterized by the food product being a drink.

Flavor masking agent

[00115] Another aspect of the invention is the use of a composition comprising neohesperidin dihydrochalcone and a cyclodextrin selected from beta-cyclodextrin and gamma-cyclodextrin as an agent for masking the taste.

[00116] In one embodiment of the invention, the taste masking composition is a mixture of NHDC and beta- or gamma-cyclodextrin and can be prepared by simply dry mixing both components, using any suitable mixing medium, e.g. , using a rotary mixer or shaker mixer.

[00117] In another embodiment of the invention, the flavor masking composition is in the form of a complex.

[00118] In this complex, the NHDC is presumably inserted, at least partially, into the beta- or gamma-cyclodextrin cavity, forming an inclusion complex. However, the term "complex", within the meaning of the present invention, is intended to include other possible variations, involving other non-stoichiometric interactions between the NHDC and the cyclodextrin to form the supramolecular complex.

[00119] This complex is typically prepared by dissolving the cyclodextrin in a suitable solvent, preferably in water, and subsequently adding NHDC to the solution and isolating the complex from the solution.

[00120] To prepare the complex with gamma-cyclodextrin, the concentration of gamma-cyclodextrin in the solution is generally between 1-20% w/v, preferably between 5-10% w/v. To prepare the complex with beta-cyclodextrin, the concentration of beta-cyclodextrin in the solution is generally between 0.5-5% w/v, preferably between 1-2% w/v.

[00121] NHDC is added to the cyclodextrin solution in an amount according to the desired NHDC:cyclodextrin molar ratio in the complex.

[00122] The mixture obtained is generally stirred until complete dissolution, typically for a period of time between 10 minutes and 3 hours, at a temperature generally between 20°C and 60°C.

[00123] To isolate the solid complex, the solvent is removed by any suitable method, for example, by freeze-drying, or it can be evaporated under reduced pressure.

[00124] As used herein, flavor masking agent, or flavor masker, means any substance or composition that provides a flavor masking effect. A taste masking effect, as is well known in the art, means the perceived reduction, modulation or elimination of an unpleasant taste or unpleasant impression of a substance.

[00125] Typically, to exert the taste-masking effect, the taste-masking composition is mixed with the unpleasant-tasting substance, generally both contained in an edible product.

[00126] In a further aspect, the present invention relates to a method for masking the unpleasant taste of a substance comprising the step of adding a composition comprising neohesperidin dihydrochalcone and a cyclodextrin selected from beta-cyclodextrin and gamma-cyclodextrin to the unpleasant substance. Typically, the composition comprising neohesperidin dihydrochalcone and cyclodextrin is added to the unpleasant-tasting substance in an amount effective to mask the taste.

[00127] Alternatively, the taste-masking composition can be prepared in situ, so that both components, i.e., NHDC and the beta- or gamma-cyclodextrin, can be added separately, preferably consecutively, to an unpleasant-tasting substance. or to an ingestible product comprising an unpleasant tasting substance, usually followed by thorough mixing.

[00128] As shown in Examples 10-12, it was surprisingly discovered that compositions comprising the composition comprising NHDC and beta-cyclodextrin or gamma-cyclodextrin show strong taste-masking synergy, that is, the taste-masking effect obtained with the components of the combination is greater than the sum of the effects of each individual substance.

[00129] This synergistic effect results in considerable cost savings, as it allows the use of fewer substances to mask unpleasant flavors in ingestible products, namely, in food and pharmaceutical products.

[00130] Substances with an unpleasant taste for the purposes of the invention are: a) substances with a bitter, astringent, cardboard, dusty, floury, rancid and/or metallic taste and b) substances that have a bitter, astringent, cardboard, dusty, floury, dry, floury, rancid or metallic taste.

[00131] Among the unpleasant flavors or unpleasant impressions that can be masked according to the use of the present invention are, for example, bitterness, astringency and metallic flavors, preferably bitterness and/or astringency.

[00132] In one embodiment, the taste masking agent according to the present invention is used to mask an unpleasant taste that is selected from bitterness and astringency, or a mixture of bitterness and astringency.

[00133] When used specifically to mask bitterness, the flavor masking agent or flavor masker may be referred to as an antibitifying agent or masking agent.

[00134] When used specifically to mask astringency, the flavor masking or masking agent may be referred to as an anti-astringency agent or astringency masking agent.

[00135] The NHDC:gamma-cyclodextrin molar ratio in the sweetener composition of the present invention is generally between 1.5:1 and 1:6, preferably between 1.2:1 and 1:4, and more preferably between 1 1:1 and 1:3.5 and even more preferably comprised between 1:1 and 1:3.

[00136] In a preferred embodiment, the NHDC:cyclodextrin molar ratio is about 1:1.

[00137] In another preferred embodiment, the NHDC:cyclodextrin molar ratio is about 1:3.

[00138] In one embodiment of the invention, the cyclodextrin is gamma-cyclodextrin.

[00139] In another embodiment of the invention, the cyclodextrin is beta-cyclodextrin.

[00140] Bitter taste or bitterness is believed to be produced by certain substances that bind to special bitter taste receptors located on the apical membrane of taste receptor cells located in the taste buds of the tongue. Bitter receptors are believed to be members of the G protein-coupled receptor (GPCR) superfamily and are referred to as T2Rs. These bitter receptors are capable of interacting with chemically very diverse ligands, so that there are a large number of substances described as bitter, whose chemical structures can belong to many different chemical classes.

[00141] In general, the taste of any substance known to impart a bitter taste can be masked using the composition according to the present invention, that is, using the combination of NHDC and beta- or gamma-cyclodextrin.

[00142] A non-limiting list of bitter substances includes, for example, flavanones, such as naringin, neohesperidin or hesperidin; flavones such as tangeritin or nobiletin; flavonols, such as avicularin, quercetin, quercitrin, isoquercetin, myricetin or rutin; flavonols such as taxifolin, catechins (catechin, epicatechin, epicatechin gallate, epigallocatechin or epigallocatechin gallate) or theaflavins (theaflavin, isoteaflavin, neotheaflavin, theaflavin-3-gallate, theaflavin-3'-gallate, theaflavin-3,3-digallate , isotheaflavin-3-gallate or theaflavic acid); isoflavones, such as genistein or daidzein; chalcones, such as chloridzine; triterpenes, such as limonin, nomilin or limonin glucoside; hydroxycinnamic acids such as caffeic acid or its esters; olive polyphenols such as oleuropein; glucosinolates such as sinigrin, progoitrin or glucobrassicin; alkaloids, such as nicotine, theobromine, theophylline, quinine or caffeine; phenolic glycosides, such as salicin or arbutin; bitter alpha acids found in hop resin, such as humulone, adhumulone, cohumulone, posthumulone or prehumulone; metallic salts, in particular potassium, magnesium and bismuth salts, such as potassium chloride, potassium gluconate, potassium carbonate, potassium succinate, potassium lactate, potassium malate; bismuth subcitrate, bismuth citrate, bismuth subgallate, bismuth salicylate or magnesium sulfate; some active pharmaceutical ingredients such as fluoro-quinolone antibiotics, aspirin, ibuprofen, paracetamol, dextromethorphan, phenylephrine, loperamide, tramadol, ranitidine hydrochloride, acetylcysteine, glucosamine sulfate, erythromycin, levosulpiride, chlorhexidine, diosmin, e-lactam antibiotics, ambroxol or guaifenesin; unsaturated fatty acids; vitamins; bitter-tasting amino acids (e.g., leucine, isoleucine, valine, tryptophan, proline, histidine, tyrosine, lysine, or phenylalanine) and some bitter-tasting peptides, particularly those containing the hydrophobic amino acids phenylalanine, tyrosine, tryptophan, leucine, isoleucine, and valine.

[00143] Astringency is defined by the American Society for Testing and Materials (ASTM, 2004) as the complex of sensations due to evasion, extraction or wrinkling of the epithelium as a result of exposure to substances such as alums and tannins. Astringent molecules are believed to react with salivary proteins, especially proline-rich proteins, causing them to precipitate, and the resulting loss of lubrication leads to the tactile sensation associated with astringency in the mouth.

[00144] Astringent molecules are commonly plant-based products, tannins, present in fruits and leaves or bark.

[00145] Some substances normally perceived as astringents are, for example, tea, red wine, rhubarb and green persimmons and bananas.

[00146] A typical example of a substance that provides an astringent impression is green tea, which contains several polyphenols, known as catechins, which are known to be astringent, namely, catechin, epigallocatechin gallate, epigallocatechin, epicatechin gallate, epicatechin and their respective stereoisomers. Other examples of substances that cause astringency are proteins, such as pea protein, whey protein, and soy protein.

[00147] Another example of astringent taste substances are the theaflavins from black tea, namely: theaflavin, theaflavin-3-gallate, theaflavin-3'-gallate, theaflavin-3,3'-digallate and theaflavic acid.

[00148] The taste of some substances can be perceived as a mixture of bitterness and astringency. So, for example, the astringent taste of green tea and black tea is sometimes perceived as a mixture of bitterness/astringency.

[00149] Other substances may have a primary flavor or flavor that is not unpleasant, but have an additional unpleasant taste, such as bitterness, astringency, or metallic notes. Without limitation, these substances may belong to the group comprising aspartame, neotame, superaspartame, saccharin, sucralose, tagatose, monellin, monk fruit, stevia extracts, individual steviol glycosides or combinations thereof, hernandulcin, thaumatin, miraculin, glycyrrhizin, acid glycyrrhetin and cyclamate.

[00150] In one embodiment, the composition comprising NHDC and gamma or beta-cyclodextrin, according to the present invention, is used as an antibitizing agent.

[00151] In another embodiment, the composition comprising NHDC and gamma or beta-cyclodextrin, according to the present invention, is used as an anti-astringency agent.

[00152] Preferably, the composition is used to mask the bitterness and/or astringency of a substance selected from the group consisting of: caffeine, ibuprofen, limonin, naringin, paracetamol, aspirin, potassium chloride, quercetin, quinine, theobromine, catechin, epigallocatechin gallate, epigallocatechin, epicatechin gallate, epicatechin, dextromethorphan, phenylephrine, guaifenesin, bismuth subsalicylate, soy protein, whey protein, pea protein, aspartame, sucralose, saccharin, stevia extracts and mixtures thereof .

[00153] More preferably, the composition is used to mask the bitterness and/or astringency of a substance selected from the group consisting of caffeine, naringin, paracetamol, potassium chloride, proteins, catechins, sucralose, stevia extracts and mixtures thereof.

[00154] In a preferred embodiment, the taste masking composition is used to mask the bitterness of the paracetamol. Preferably, a composition comprising NHDC and gamma-cyclodextrin is used. According to this embodiment, the NHDC:gamma-cyclodextrin molar ratio is preferably comprised between 1.5:1 and 1:10, more preferably comprised between 1.5:1 and 1:6, even more preferably comprised between 1.2 :1 and 1:4, even more preferably between 1.1:1 and 1:3.5 and even more preferably between 1:1 and 1:3. In a particularly preferred embodiment, the ratio is about 1:3. In another particularly preferred embodiment, the ratio is about 1:1.

[00155] In another preferred embodiment, the flavor masking composition is used to mask the bitterness of quinine. Preferably, a composition comprising NHDC and beta-cyclodextrin is used. According to this embodiment, the molar ratio NHDC: beta-cyclodextrin is preferably comprised between 1.5:1 and 1:10, more preferably comprised between 1.5:1 and 1:6, even more preferably comprised between 1.2 :1 and 1:4, even more preferably between 1.1:1 and 1:3.5 and even more preferably between 1:1 and 1:3. In a particularly preferred embodiment, the ratio is about 1:3. In another particularly preferred embodiment, the ratio is about 1:1.

[00156] In another preferred embodiment, the flavor masking composition is used to mask the astringent taste of green tea. According to this embodiment, the composition has an astringency masking effect against the astringent components of green tea, typically the catechins epigallocatechin gallate, epigallocatechin, epicatechin gallate and/or epicatechin.

[00157] According to this embodiment, the NHDC:cyclodextrin molar ratio is preferably comprised between 1.5:1 and 1:10, more preferably comprised between 1.5:1 and 1:6, even more preferably comprised between 1. 2:1 and 1:4, even more preferably between 1.1:1 and 1:3.5 and even more preferably between 1:1 and 1:3. In a particularly preferred embodiment, the ratio is about 1:3. In another particularly preferred embodiment, the ratio is about 1:1.

[00158] The taste masking agent according to the present invention is typically added to an ingestible product comprising an unpleasant tasting substance, typically comprising a bitter substance and/or an astringent substance.

[00159] Another aspect of the invention is a process for masking the unpleasant taste of an ingestible product that contains at least one unpleasant-tasting substance comprising adding to the ingestible product a taste-masking composition comprising neohesperidin dihydrochalcone and a cyclodextrin selected from beta-cyclodextrin and gamma-cyclodextrin.

[00160] The step of adding the flavor-masking composition to the ingestible product should include the addition of the pre-mixed composition, as well as the incorporation of both components, i.e., NHDC and the beta- or gamma-cyclodextrin, separately, preferably consecutively, to the ingestible product.

[00161] Another aspect of the invention is an ingestible product comprising at least one unpleasant-tasting substance and a taste-masking composition comprising neohesperidin dihydrochalcone and a cyclodextrin selected from beta-cyclodextrin and gamma-cyclodextrin. Preferably, the unpleasant-tasting substance is a bitter or astringent substance.

[00162] The amount of the unpleasant-tasting substance contained in the ingestible product is sufficient to be perceived as unpleasant when the ingestible product does not comprise the taste-masking agent.

[00163] In one embodiment, the amount of the unpleasant-tasting substance in the ingestible product is in the range of 1-5000 ppm, based on the total weight of the ingestible product, without an agent to mask the taste.

[00164] The taste masking agent is added to the ingestible product in an amount effective to mask the taste. As used herein, an "effective taste-masking amount" is that amount of the taste-masking composition that is sufficient to reduce, modify, or eliminate the unpleasant taste of the unpleasant substance as compared to the ingestible product without the taste-masking agent. flavor. The effective amount of taste masking can vary widely depending on the particular unpleasant-tasting substance, its relative amount in the ingestible product and the specific ingestible product.

[00165] Those skilled in the art will have no difficulty in choosing the appropriate amount to mask the taste in each particular case.

[00166] In one embodiment, the flavor masking composition is added in an amount comprised between 1-2000 ppm, preferably comprised between 1-1000 ppm and more preferably comprised between 1-500 ppm, relative to the total weight of the ingestible product. . The total weight of the ingestible product must also include the weight of the added sweetening composition.

[00167] The term "ingestible product" as used herein broadly refers to any substance intended to be ingested orally by a human or animal, and includes substances that are drunk, eaten, swallowed or ingested in other ways, namely food products and pharmaceutical products. Furthermore, the term "ingestible product" should also include substances that should not be ingested but are first ingested into the mouth and subsequently expelled, for example, chewing gum and oral hygiene compositions such as mouthwashes, toothpastes or gels. tooth, for example.

[00168] In one embodiment of the present invention, the ingestible product is selected from the group consisting of food products, pharmaceutical products and oral hygiene compositions; preferably selected from food and pharmaceutical products.

[00169] In another embodiment of the present invention, the ingestible product is a food product.

[00170] In another embodiment of the present invention, the ingestible product is a pharmaceutical product.

[00171] The expression "food product", as used in this document, means any edible product intended for human or animal nutrition and includes solids, semisolids and liquids, also including beverages. The term "food product" also includes products that are intended to be partially ingested and subsequently expelled from the oral cavity, particularly chewing gum.

[00172] Beverages suitable for adding to the taste-masking agent according to the present invention may be, without limitation, any type of beverage containing an unpleasant-tasting substance, preferably containing a bitter and/or astringent substance, and they can be carbonated or non-carbonated, alcoholic or non-alcoholic, and include, among others, fruit-flavored soft drinks, soft drinks, colas, sports drinks and, in general, any drink containing and/or flavored with fruits, vegetables, aromatic plants , tea, coffee or cocoa, for example; also includes drinks containing wine or beer, for example; also includes energy or health drinks containing, for example, protein hydrolysates, vitamins and/or phytonutrients with a bitter and/or astringent taste.

[00173] The beverage category includes ready-to-drink beverages, as well as other forms, such as powders, granules, tablets or liquid concentrates, which must be reconstituted with water.

[00174] Other food products suitable for adding to the masking agent according to the present invention are, for example, bakery products, such as bread, cakes, biscuits, muffins and, in general, any type of cooked food; also dairy products such as yogurt, drinking yogurt, frozen yogurt, milk, milk-based drinks, condensed milk, cream, cheese or ice cream; soy-based products such as soy milk or soy lecithin; confectionery products such as chocolate, caramels, sweets, marzipan or chewing gum; cereal-type products, such as breakfast cereals, cereal bars, energy/nutrition bars or flakes; fruit products such as jelly, fruit puree, preserved fruit and sauces; vegetable-derived products, such as sauces, dried, preserved or frozen vegetables; Oil-based products and emulsions, such as mayonnaise and various dressings, among many others, as long as they contain a substance with an unpleasant taste, preferably a substance with a bitter and/or astringent taste.

[00175] The category of food products also includes, in particular, nutritional or dietary supplements, that is, food products enriched in some nutritional ingredients, for example, vitamins, minerals, amino acids, proteins, vegetables, enzymes or other substances intended to supplement the human diet and which can be in any suitable food form, typically as drinks or bars, for example.

[00176] Also included in the term food products are all types of dry products, such as desert mixes or dry ready meals.

[00177] Food products also include, in particular, any food intended for animal nutrition.

[00178] Pharmaceutical products suitable for adding to the taste-masking agent according to the present invention are those that comprise an active ingredient with an unpleasant taste, namely, a bitter or astringent ingredient, also including any type of health supplement with unpleasant taste, e.g. vitamins, minerals and mixtures thereof. Preferably, the bitter or astringent active ingredient is selected from fluoro-quinolone antibiotics, ibuprofen, paracetamol, e-lactam antibiotics, ambroxol, guaifenesin and mixtures thereof; preferably the active ingredient is paracetamol.

[00179] Pharmaceutical products may be in any form suitable for oral administration, for human or veterinary therapy. Pharmaceutical products may be in any form suitable for oral administration as are well known to those skilled in the art, for example solid forms such as tablets, chewable tablets, orally disintegrating tablets (ODT), sublingual tablets, orally disintegrating films (films). flash), tablets, gums or chewable powders; or liquid forms, such as drops, syrups and suspensions; or alternatively, in the form of powders, granules or tablets intended to be dissolved in a liquid to be administered, for example effervescent tablets.

[00180] The taste masking composition of the invention can be added to the ingestible product in a conventional manner, as is well known to those skilled in pharmaceutical technology or food technology, for example, it can be added to a pharmaceutical product, together with other excipients of the formulation or to a food product at an appropriate stage in the manufacturing process.

[00181] It is understood that the above examples are non-limiting and any ingestible product that contains a substance with an unpleasant taste, preferably a bitter and/or astringent substance, may be appropriate to add to it the composition to mask the taste in accordance with the present invention.

[00182] Another aspect of the invention relates to a taste masking composition comprising neohesperidin dihydrochalcone and gamma-cyclodextrin.

[00183] In one embodiment, the flavor masking composition is a mixture of both components.

[00184] In another embodiment, NHDC and gamma-cyclodextrin are in the form of a complex.

[00185] The NHDC:gamma-cyclodextrin molar ratio according to this aspect of the invention is generally comprised between 1.5:1 and 1:10, more preferably comprised between 1.5:1 and 1:6, even more preferably comprised between 1.2:1 and 1:4, even more preferably between 1.1:1 and 1:3.5 and even more preferably between 1:1 and 1:3.

[00186] In a preferred embodiment of this aspect of the invention, the NHDC:gamma-cyclodextrin molar ratio is about 1:1.

[00187] In another preferred embodiment, the NHDC:gamma-cyclodextrin molar ratio is about 1:3.

[00188] Aspects of the present invention related to the taste masking composition comprising NHDC and gamma-cyclodextrin or beta-cyclodextrin can be defined according to the following embodiments: 1. Use of a composition comprising neohesperidin dihydrochalcone and a cyclodextrin selected from beta -cyclodextrin and gamma-cyclodextrin as flavor masking agent. 2. Use, according to modality 1, characterized in that the composition is a mixture of neohesperidin dihydrochalcone and cyclodextrin. 3. Use, according to modality 1, characterized in that neohesperidin dihydrochalcone and cyclodextrin are in the form of a complex. 4. Use, according to any of modalities 1 to 3, characterized by the molar ratio neohesperidin dihydrochalcone:cyclodextrin being between 1.5:1 and 1:10. 5. Use, according to any of modalities 1 to 4, characterized by the neohesperidin dihydrochalcone:cyclodextrin molar ratio being between 1.5:1 and 1:6. 6. Use, according to modality 5, characterized by the neohesperidin dihydrochalcone:cyclodextrin molar ratio being between 1.2:1 and 1:4. 7. Use, according to modality 6, characterized by the neohesperidin dihydrochalcone:cyclodextrin molar ratio being between 1.1:1 and 1:3.5. 8. Use, according to modality 7, characterized by the molar ratio neohesperidin dihydrochalcone: gamma-cyclodextrin being between 1:1 and 1:3. 9. Use, according to any of modalities 1 to 8, characterized by the molar ratio neohesperidin dihydrochalcone:cyclodextrin being 1:1. 10. Use, according to any of embodiments 1 to 8, characterized by the neohesperidin dihydrochalcone:cyclodextrin molar ratio being about 1:1. 11. Use, according to any of modalities 1 to 8, characterized by the molar ratio neohesperidin dihydrochalcone:cyclodextrin being 1 ± 0.1:1 ± 0.1. 12. Use, according to modality 11, characterized by the molar ratio neohesperidin dihydrochalcone:cyclodextrin being 1 ± 0.05:1 ± 0.05. 13. Use, according to any of modalities 1 to 8, characterized by the molar ratio neohesperidin dihydrochalcone:cyclodextrin being 1:3. 14. Use, according to any of embodiments 1 to 8, characterized by the neohesperidin dihydrochalcone:cyclodextrin molar ratio being about 1:3. 15. Use, according to any of modalities 1 to 8, characterized by the molar ratio neohesperidin dihydrochalcone:cyclodextrin being 1 ± 0.1:3 ± 0.3. 16. Use, according to modality 15, characterized by the molar ratio neohesperidin dihydrochalcone:cyclodextrin being 1 ± 0.05: 3 ± 0.15. 17. Use, according to any of modalities 1 to 16, characterized in that the cyclodextrin is beta-cyclodextrin. 18. Use, according to any of embodiments 1 to 16, characterized in that the cyclodextrin is gamma-cyclodextrin. 19. Use, according to any of modalities 1 to 18, to mask bitterness. 20. Use, according to any of modalities 1 to 19, to mask astringency. 21. Use, in accordance with any of embodiments 1 to 20, to mask metallic notes. 22. Use, according to any of modalities 1 to 21, to mask bitterness and/or astringency and/or metallic notes. 23. Use, according to any of embodiments 1 to 20, to mask the bitterness and/or astringency of a substance selected from the group consisting of: caffeine, ibuprofen, limonin, naringin, paracetamol, aspirin, potassium chloride, quercetin , quinine, theobromine, catechin, epigallocatechin gallate, epigallocatechin, epicatechin gallate, epicatechin, dextromethorphan, phenylephrine, guaifenesin, bismuth subsalicylate, soy protein, whey protein, pea protein, aspartame, sucralose, saccharin, extracts of stevia. 24. Use, according to modality 23, characterized by the substance being selected from the group consisting of: caffeine, naringin, paracetamol, potassium chloride, proteins, catechins, sucralose, stevia extracts and mixtures thereof. 25. Use, according to any of modalities 1 to 18, characterized by being to mask the bitterness of paracetamol. 26. Use, according to any of modalities 1 to 18, characterized in that it is to mask the bitterness of the quinine. 27. Use, according to any of modalities 1 to 18, characterized by being to mask the astringency of green tea. 28. Process for masking the unpleasant taste of an ingestible product containing at least one unpleasant-tasting substance comprising adding to the ingestible product a taste-masking composition comprising neohesperidin dihydrochalcone and a cyclodextrin selected from beta-cyclodextrin and gamma-cyclodextrin . 29. Process, according to embodiment 28, characterized by the taste masking composition having a neohesperidin dihydrochalcone:cyclodextrin molar ratio that is between 1.5:1 and 1:10. 30. Process, according to embodiment 28 or 29, characterized by the taste masking composition having a neohesperidin dihydrochalcone:cyclodextrin molar ratio that is between 1.5:1 and 1:6. 31. Process, according to embodiment 30, characterized by the taste masking composition having a neohesperidin dihydrochalcone:cyclodextrin molar ratio that is between 1.2:1 and 1:4. 32. Process, according to embodiment 31, characterized by the taste masking composition having a neohesperidin dihydrochalcone:cyclodextrin molar ratio that is between 1.1:1 and 1:3.5. 33. Process, according to embodiment 32, characterized by the taste masking composition having a neohesperidin dihydrochalcone:cyclodextrin molar ratio that is between 1:1 and 1:3. 34. Process, according to any one of embodiments 28 to 33, characterized by the taste masking composition having a neohesperidin dihydrochalcone:cyclodextrin molar ratio that is 1:1. 35. Process, according to any one of embodiments 28 to 33, characterized by the taste masking composition having a neohesperidin dihydrochalcone:cyclodextrin molar ratio that is about 1:1. 36. Process, according to any one of embodiments 28 to 33, characterized by the taste masking composition having a neohesperidin dihydrochalcone:cyclodextrin molar ratio that is 1 ± 0.1:1 ± 0.1. 37. Process, according to embodiment 36, characterized by the taste masking composition having a neohesperidin dihydrochalcone:cyclodextrin molar ratio that is 1 ± 0.05:1 ± 0.05. 38. Process, according to any one of embodiments 28 to 33, characterized by the taste masking composition having a neohesperidin dihydrochalcone:cyclodextrin molar ratio that is 1:3. 39. Process, according to any one of embodiments 28 to 33, characterized by the taste masking composition having a neohesperidin dihydrochalcone:cyclodextrin molar ratio that is about 1:3. 40. Process, according to any one of embodiments 28 to 33, characterized by the taste masking composition having a neohesperidin dihydrochalcone:cyclodextrin molar ratio that is 1 ± 0.1:3 ± 0.3. 41. Process, according to embodiment 40, characterized by the taste masking composition having a neohesperidin dihydrochalcone:cyclodextrin molar ratio that is 1 ± 0.05: 3 ± 0.15. 42. Process, according to any of embodiments 28 to 41, characterized by the unpleasant taste being bitterness and/or astringency. 43. Process, according to any one of embodiments 28 to 42, characterized in that the substance with an unpleasant taste is selected from the group consisting of: caffeine, ibuprofen, limonin, naringin, paracetamol, aspirin, potassium chloride, quercetin, quinine, theobromine , catechin, epigallocatechin gallate, epigallocatechin, epicatechin gallate, epicatechin, dextromethorphan, phenylephrine, guaifenesin, bismuth subsalicylate, soy protein, whey protein, pea protein, aspartame, sucralose, saccharin, stevia extracts and mixtures of the same. 44. Process, according to embodiment 43, characterized in that the unpleasant-tasting substance is selected from the group consisting of: caffeine, naringin, paracetamol, potassium chloride, proteins, catechins, sucralose, stevia extracts and mixtures thereof. 45. Process, according to any one of embodiments 28 to 44, characterized in that the ingestible product is selected between a food product and a pharmaceutical product. 46. Process, according to embodiment 45, characterized in that the ingestible product is a pharmaceutical product that contains a bitter active ingredient selected from paracetamol, ibuprofen, aspirin, dextromethorphan, phenylephrine, guaifenesin and bismuth subsalicylate. 47. Process, according to modality 45, characterized in that the ingestible product is a food product comprising a bitter or astringent substance selected from caffeine, limonin, naringin, potassium chloride, quercetin, quinine, catechins, soy protein, soy protein, whey, pea protein extracts, aspartame, sucralose, saccharin and stevia. 48. Ingestible product that contains at least one unpleasant-tasting substance and a taste-masking composition, wherein the taste-masking composition comprises neohesperidin dihydrochalcone and a cyclodextrin selected from beta-cyclodextrin and gamma-cyclodextrin. 49. Ingestible product, according to modality 48, characterized by the substance with an unpleasant taste being a bitter or astringent substance. 50. Ingestible product, according to modalities 48 or 49, characterized in that the substance with an unpleasant taste is selected from the group consisting of: caffeine, ibuprofen, limonin, naringin, paracetamol, aspirin, potassium chloride, quercetin, quinine, theobromine, catechin, epigallocatechin gallate, epigallocatechin, epicatechin gallate, epicatechin, dextromethorphan, phenylephrine, guaifenesin, bismuth subsalicylate, soy protein, whey protein, pea protein, aspartame, sucralose, saccharin, stevia extracts and mixtures thereof . 51. Ingestible product, according to any of modalities 48 to 50, characterized in that the unpleasant substance is selected from the group consisting of: caffeine, naringin, paracetamol, potassium chloride, proteins, catechins, sucralose, stevia extracts and mixtures thereof . 52. Ingestible product, according to any of embodiments 48 to 51, characterized in that the ingestible product is selected between a food product and a pharmaceutical product. 53. Ingestible product, according to modality 52, characterized by being a pharmaceutical product containing an unpleasant-tasting substance that is a bitter active ingredient selected from paracetamol, ibuprofen, aspirin, dextromethorphan, phenylephrine, guaifenesin and bismuth subsalicylate. 54. Ingestible product, according to modality 52, characterized by being a food product that contains an unpleasant-tasting substance that is a bitter or astringent substance selected from caffeine, limonin, naringin, potassium chloride, quercetin, quinine, catechins, soy protein, whey protein extracts, pea protein, aspartame, sucralose, saccharin and stevia. 55. Ingestible product, according to any one of embodiments 48 to 54, characterized by the taste masking composition having a neohesperidin dihydrochalcone:cyclodextrin molar ratio that is between 1.5:1 and 1:10. 56. Ingestible product, according to any one of embodiments 48 to 55, characterized by the taste masking composition having a neohesperidin dihydrochalcone:cyclodextrin molar ratio that is between 1.5:1 and 1:16. 57. Ingestible product, according to embodiment 56, characterized by the taste masking composition having a neohesperidin dihydrochalcone:cyclodextrin molar ratio that is between 1.2:1 and 1:4. 58. Ingestible product, according to embodiment 57, characterized by the taste masking composition having a neohesperidin dihydrochalcone:cyclodextrin molar ratio that is between 1.1:1 and 1:3.5. 59. Ingestible product, according to embodiment 58, characterized by the taste masking composition having a neohesperidin dihydrochalcone:cyclodextrin molar ratio that is between 1:1 and 1:3. 60. Ingestible product, according to any one of embodiments 48 to 59, characterized by the taste masking composition having a neohesperidin dihydrochalcone:cyclodextrin molar ratio that is 1:1. 61. Ingestible product, according to any one of embodiments 48 to 59, characterized by the taste masking composition having a neohesperidin dihydrochalcone:cyclodextrin molar ratio that is about 1:1. 62. Ingestible product, according to any one of embodiments 48 to 59, characterized by the taste masking composition having a molar ratio of neohesperidin dihydrochalcone:cyclodextrin that is 1 ± 0.1:1 ± 0.1. 63. Ingestible product, according to embodiment 62, characterized by the taste masking composition having a neohesperidin dihydrochalcone:cyclodextrin molar ratio that is 1 ± 0.05:1 ± 0.05. 64. Ingestible product, according to any one of embodiments 48 to 59, characterized by the taste masking composition having a neohesperidin dihydrochalcone:cyclodextrin molar ratio that is 1:3. 65. Ingestible product, according to any one of embodiments 48 to 59, characterized by the taste masking composition having a neohesperidin dihydrochalcone:cyclodextrin molar ratio that is about 1:3. 66. Ingestible product, according to any one of embodiments 48 to 59, characterized by the taste masking composition having a molar ratio of neohesperidin dihydrochalcone:cyclodextrin that is 1 ± 0.1:3 ± 0.3. 67. Ingestible product, according to embodiment 66, characterized by the taste masking composition having a neohesperidin dihydrochalcone:cyclodextrin molar ratio that is 1 ± 0.05: 3 ± 0.15. 68. Ingestible product, according to any of embodiments 48 to 67, characterized in that the cyclodextrin is beta-cyclodextrin. 69. Ingestible product, according to any of embodiments 48 to 67, characterized in that the cyclodextrin is gamma-cyclodextrin. 70. Taste masking composition comprising neohesperidin dihydrochalcone and gamma-cyclodextrin. 71. Composition to mask the taste, according to embodiment 70, characterized in that it is a mixture of neohesperidin dihydrochalcone and gamma-cyclodextrin. 72. Composition for masking the taste, according to embodiment 70, characterized in that neohesperidin dihydrochalcone and gamma-cyclodextrin are in the form of a complex. 73. Composition for masking the taste, according to any one of embodiments 70 to 72, characterized in that the molar ratio neohesperidin dihydrochalcone: gamma-cyclodextrin is between 1.5:1 and 1:10. 74. Composition for masking the taste, according to any one of embodiments 70 to 73, characterized in that the molar ratio neohesperidin dihydrochalcone: gamma-cyclodextrin is between 1.5:1 and 1:6. 75. Composition for masking the taste, according to embodiment 74, characterized in that the molar ratio neohesperidin dihydrochalcone: gamma-cyclodextrin is between 1.2:1 and 1:4. 76. Composition for masking the taste, according to embodiment 75, characterized in that the molar ratio neohesperidin dihydrochalcone: gamma-cyclodextrin is between 1.1:1 and 1:3.5. 77. Composition for masking the taste, according to any one of embodiments 70 to 76, characterized in that the molar ratio neohesperidin dihydrochalcone: gamma-cyclodextrin is between 1:1 and 1:3. 78. Composition for masking the taste, according to any one of embodiments 70 to 77, characterized in that the molar ratio neohesperidin dihydrochalcone: gamma-cyclodextrin is 1:1. 79. Composition for masking the taste, according to any one of embodiments 70 to 77, characterized in that the molar ratio neohesperidin dihydrochalcone: gamma-cyclodextrin is about 1:1. 80. Composition for masking the taste, according to any one of embodiments 70 to 77, characterized by the molar ratio neohesperidin dihydrochalcone: gamma-cyclodextrin being 1 ± 0.1:3 ± 0.3. 81. Composition for masking the taste, according to embodiment 80, characterized by the molar ratio neohesperidin dihydrochalcone: gamma-cyclodextrin being 1 ± 0.05: 3 ± 0.15. 82. Composition for masking the taste, according to any one of embodiments 70 to 77, characterized in that the molar ratio neohesperidin dihydrochalcone: gamma-cyclodextrin is 1:3. 83. Composition for masking the taste, according to any one of embodiments 70 to 77, characterized in that the molar ratio neohesperidin dihydrochalcone: gamma-cyclodextrin is about 1:3. 84. Composition for masking the taste, according to any of embodiments 70 to 77, characterized by the molar ratio neohesperidin dihydrochalcone: gamma-cyclodextrin being 1 ± 0.1:3 ± 0.3. 85. Composition for masking the taste, according to embodiment 84, characterized in that the molar ratio neohesperidin dihydrochalcone: gamma-cyclodextrin is 1 ± 0.05: 3 ± 0.15. The following examples further illustrate the invention.

EXAMPLES Example 1: Sweetening compositions

[00189] Various sweetener compositions according to the present invention were prepared, using different molar proportions between neohesperidin dihydrochalcone (NHDC) and gamma-cyclodextrin (gCD), as disclosed in Table 1. NHDC was supplied by Ferrer HealthTech and the range -cyclodextrin was supplied by Wacker.

[00190] From the molar masses of NHDC (613) and gamma-cyclodextrin (1297), the weight percentage of NHDC contained in each composition was calculated. TABLE 1

[00191] The sweetening compositions employed were in the form of a complex.

[00192] To prepare the complex of Example A, NHDC (14.0 g, 20.6 mmol) was added to a stirred solution of gCD (30 g, 20.6 mmol) in deionized water (500 ml). The mixture was stirred for one hour at 20-25°C, until complete dissolution. The solution was clarified through a 0.8 μm filter to remove insoluble particles. The solvent was removed under reduced pressure. An off-white solid (40 g) of the 1:1 complex was obtained.

[00193] To prepare the complex of Example B, NHDC (7.5 g, 11 mmol) was added to a stirred solution of gCD (47.7 g, 33 mmol) in deionized water (500 ml). The mixture was stirred for one hour at 20-25°C, until complete dissolution. The solution was clarified through a 0.8 μm filter to remove insoluble particles. The solvent was removed under reduced pressure. An off-white solid (54 g) of the 1:3 complex was obtained.

[00194] The complexes of Examples C-E were prepared under the same conditions described above for Examples A and B.

Example 2: Comparative sweetener compositions

[00195] For comparative purposes, sweetener compositions equivalent to Examples A and B were prepared, but using beta-cyclodextrin instead of gamma-cyclodextrin, also in the form of a complex. Thus, Comparative Examples A and B were prepared using the molar ratios between NHDC and beta-cyclodextrin (bCD) disclosed in Table 2. Beta-cyclodextrin was supplied by Wacker.

[00196] Analogous to Example 1, using the molar masses of NHDC (613) and beta-cyclodextrin (1138), the weight percentage of NHDC contained in each composition was calculated. TABLE 2

[00197] To prepare the complex of Comparative Example A, NHDC (7.0 g, 10.2 mmol) was added to a stirred solution of bCD (13.4 g, 10.2 mmol) in deionized water (900 ml ) at 50°C. The mixture was stirred for two hours at 50°C, until complete dissolution. The solution was clarified through a 0.8 μm filter to remove insoluble particles. The solvent was removed under reduced pressure. An off-white solid (18.1 g) of the 1:1 complex was obtained.

[00198] To prepare the complex of Comparative Example B, NHDC (4.0 g, 5.8 mmol) was added to a stirred solution of bCD (22.9 g, 17.5 mmol) in deionized water (1500 ml) at 50°C. The mixture was stirred for two hours at 50°C, until complete dissolution. The solution was clarified through a 0.8 μm filter to remove insoluble particles. The solvent was removed under reduced pressure. An off-white solid (23.9 g) of the 1:3 complex was obtained.

Example 3: Sweetening synergy tests

[00199] A sensory test was carried out to evaluate the sweetening synergism achieved with the composition of the invention (Examples A and B), and this effect was also compared to the effect obtained with analogous compositions containing beta-cyclodextrin (Comparative Examples A and B) . Other compositions of the present invention (Examples C, D and E) were also evaluated in this sensory test.

[00200] A group of those skilled in the art in sweet descriptors evaluated the sweetness of the different compositions, as well as that of the ingredients NHDC, beta-cyclodextrin and gamma-cyclodextrin used alone.

[00201] Each sweetener evaluated was dissolved in water in different concentrations, at room temperature. The panel determined, for each product, the concentration equivalent to the reference solutions of 1% and 3% sucrose in water. The results are summarized in Table 3 (Examples A and B are abbreviated as Ex. A and Ex. B, respectively, and Comparative Examples A and B are abbreviated as Comp. A and Comp. B, respectively). TABLE 3

[00202] As beta- and gamma-cyclodextrins are also sweet compounds, equisweet concentrations of both cyclodextrins were also determined by the test panel to evaluate their possible contribution to the sweetness of the composition. The concentration of equisweet beta-cyclodextrin at 1% and 3% sucrose was found to be 12000 and 70000 ppm, respectively, and the equivalent equisweet concentrations for gamma-cyclodextrin were 25000 and 85000 ppm. Therefore, as the equisweet concentrations of both cyclodextrins are at least three orders of magnitude greater than those of NHDC, it was concluded that their contribution to sweetness was negligible.

[00203] The first line of data for each sucrose level in Table 3 shows the equisweet concentrations (in ppm) for each agent evaluated, while in the second line, the amount of pure NHDC (in ppm) present at these equisweet concentrations is calculated. These results are shown graphically in Figures 1 and 2.

[00204] A more quantitative assessment of the synergy of sweetness provided by the compositions of the present invention was carried out by comparing the actual measured sweetness of the compositions comprising gamma-cyclodextrin and NHDC with the theoretical sweetness expected from the sum of the individual contribution of each component in the composition.

[00205] To this end, the relative sweetener potency of each component was first calculated. For comparative purposes, the relative sweetening potency of beta-cyclodextrin was also calculated. The relative sweetening potency of a given compound, at a given sweetness level, indicates how many times sweeter that compound is than sucrose. Therefore, it is calculated as the ratio between the sucrose concentration and the equisweet concentration of each ingredient, for each sweetness level. The relative sweetening potencies of NHDC, beta-cyclodextrin (bCD) and gamma-cyclodextrin (gCD) are shown in Table 4. TABLE 4

[00206] From the relative sweetener potency of each ingredient, it is possible to calculate the expected sweetness (sucrose equivalent) of a mixture of these ingredients, according to Formula I: Expected sweetness (sucrose equivalent) of a mixture C1 + C2 = Concentration of compound C1

[00207] Then, the sweetness synergy of a mixture of components can be calculated according to Formula II:

[00208] Tables 5 and 6 below show the expected (theoretical) sweetness and sweetness synergy for the compositions of the present invention (Examples A and B) and, for comparative purposes, also for Comparative Examples A and B, containing the combination of NHDC and beta-cyclodextrin, for 1% sucrose level (table 5) and 3% sucrose level (table 6). TABLE 5 TABLE 6

[00209] For example, for the 1% sucrose level (Table 5), the expected sweetness of 12 ppm of the composition of Example A (first column) is calculated using Formula I, as follows: 3.85 10- 4 x 2000 + 8.12 10-4 x 0.4, that is, 0.77% sucrose equivalence. As the actual sweetness is equivalent to 1% sucrose, the synergy can be calculated using Formula II, as follows: 1-0.77/0.77, i.e. 29.9% synergy.

[00210] Similarly, for the 3% sucrose level (Table 6), the expected sweetness of 42 ppm of the composition of Example A (first column) is calculated using Formula I, as follows: 13.48 10-4 x 1250 + 28.52 10-4 x 0.3529, that is, 1.70% sucrose equivalence. Then, synergy can be calculated using Formula II, as follows: (3-1.70)/1.70, that is, 76.5% synergy.

[00211] All expected sweetness and sweetness synergy values in Tables 5 and 6 were calculated analogously, using the appropriate values of relative sweetener potency (according to Table 4) and the actual actual sweetness value (1% or 3%).

Example 4: Evolution of sweetening power with sweetness level

[00212] As disclosed above in Example 3, the relative sweetener potency of a given compound, at a given sweetness level, indicates how many times sweeter than sucrose the compound is and the value is calculated as the ratio between the concentration of sucrose and the equisweet concentration of the compound.

[00213] The relative sweetening potency of NHDC at 1% and 3% sucrose levels was calculated in Example 3 and is shown in Table 4.

[00214] The sweetening potency of the compositions of the invention in relation to sucrose can be analogously calculated at a given level of sucrose. Thus, for example, since 12 and 42 ppm of the composition of Example A are equivalent to 1% and 3% sucrose solutions, respectively (see Table 3), it follows that the composition of Example A is 833 and 714 times sweeter than sucrose, at sucrose levels of 1% and 3%, respectively.

[00215] Likewise, since 26 and 90 ppm of the composition of Example B are equivalent to 1% and 3% sucrose solutions, respectively (see Table 3), it follows that the composition of Example B is 385 and 333 times sweeter than sucrose, at 1% and 3% sucrose, respectively.

[00216] The values of the relative sweetener potency of each substance and also those of the compositions of Examples AD are summarized below in Table 7. TABLE 7 The results in Table 7 are represented in the graph in Figure 3.

Example 5: Flavor profile

[00217] The general flavor profile obtained with the sweetener composition of the present invention was evaluated and compared with the target flavor profile of sucrose.

[00218] For this assay, all samples were evaluated at the same sweetness level, so each sample was used at a concentration that was equisweet to 3% sucrose. For each sample, the following parameters were evaluated: - Time to first detection of sweetness - Time to maximum sweetness - Prolonged (time for sweetness to disappear) - Flavor: menthol, licorice (any flavor other than sweetness) - Mouthfeel (density , i.e. the viscosity perceived in the mouth)

[00219] These evaluations were carried out by a calibrated taste panel and conducted at room temperature. Each of these parameters was evaluated on a scale of 0 to 5 points. The sucrose values were the reference and were considered the target to be copied. The results obtained with this test are summarized in the following table: TABLE 8

[00220] The results of Table 8 are shown graphically in Figure 4, in the form of a spider graph. Example 6: Sweetened drink

[00221] An orange reference soft drink sweetened with high fructose corn syrup (HFCS) was prepared using the ingredients listed in Table 9 (Formula 1). All percentages in the table are by weight. TABLE 9 * HFCS-42 = HFCS with 42% fructose content.

[00222] To prepare the drinks, the following process was followed. High fructose corn syrup was weighed into a 1L cup. The remaining minor ingredients (sodium benzoate, potassium sorbate, citric acid, orange soda color, and orange soda flavor) were weighed separately into small cups and water was added to each of the small precipitation cups and mixed until solubilize each ingredient. Once dissolved, all of these minor ingredients were added to the 1 L precipitation beaker with the HFCS. The obtained solution was mixed well and water was gradually added to 1 kg.

[00223] To test the possible replacement of HFCS by NHDC and with the composition of the present invention (Example B), a stock solution of 0.1% NHDC in water was prepared by gradually adding 0.1 g of NHDC at 99, 9 g of water, mixing and heating at 66°C for 15 minutes until obtaining a yellowish solution; the solution was then allowed to cool to room temperature. Similarly, a 1% stock solution of Example B in water was prepared by adding 1 g of Example B to 99 g of water and mixing, thus obtaining a yellowish solution.

[00224] Maximum sugar replacement with NHDC was then determined by substituting increasing amounts of HFCS for NHDC and passing the reference and prototype through a triangular test on a calibrated panel. Therefore, the criteria for determining maximum sugar substitution was not just the equisweetness between the reference and the prototype, but the overall flavor profile.

[00225] The maximum sugar replacement achieved with NHDC without any noticeable difference in a triangular test was 10% (Formula 2 of Table 9). This substitution was achieved with 10 ppm NHDC.

[00226] In a second step, the panel determined the amount of Example B (composition containing an NHDC: bCD molar ratio of 1:3) to obtain the same sugar substitution. The same 10% sugar replacement was achieved with 33 ppm of the Example B composition, which contained 4.5 ppm NHDC (Formula 3 of Table 9).

Example 7: Sweetened drink

[00227] The objective of this example was to maximize sugar replacement in an orange juice-based soft drink while maintaining the same overall flavor profile. A calibrated panel was unable to distinguish the reference from the different prototypes in the triangular test.

[00228] The reference product (Formula 1 of Table 10) contained 10% added sucrose. The maximum sucrose replacement achieved with NHDC was 15% of the initial 10%, using 10 ppm NHDC (Formula 2 of Table 10). With the sweetener composition of the present invention, it was possible to increase sucrose substitution by up to 25% without changing the flavor profile of the drink (Formula 3 of Table 10).

[00229] The composition of each drink is disclosed in Table 10. For the preparation of these drinks, a concentrated orange juice 65° Bx (Dallant) and orange flavor # 2N341/C (Dallant) were used. All percentages in the table are by weight. TABLE 10

Example 8: Sweetened dark chocolate

[00230] Different sweetened dark chocolate formulas were prepared using the ingredients listed in Table 11. The percentages in the table are expressed by weight. TABLE 11

[00231] The reference product (Formula 1 of Table 11) contained a commercial chocolate with 70% cocoa content (Lindt®) and 6% powdered sugar.

[00232] Throughout all the tests carried out, the objective was to maximize the replacement of sucrose, while maintaining the same general flavor profile. A calibrated panel was unable to distinguish the reference from the different prototypes tested.

[00233] In a first test, the maximum substitution of sucrose with only NHDC was evaluated. In this case, NHDC was added in the form of a 1% solution in glycerol, and the maximum sugar replacement in this case was 10% sucrose (from the initial 6% of the formula). This reduction was achieved using 0.03% glycerol solution, equivalent to 3 ppm NHDC (Formula 2 of Table 11).

[00234] Using the same amount of pure NHDC, that is, 3 ppm, but contained in the composition of Example B (equivalent to 22 ppm of Example B), it was found that it was possible to replace a higher percentage of sugar from the reference product , up to 18.17% sugar (Formula 3 of Table 11).

[00235] In another test, the maximum substitution of sucrose was determined with the composition of Example B. Using this composition, it was possible to reduce up to 28% of sugar from the reference product, without changing the flavor profile of the product, using 40 ppm of the Example B (containing 5.45 ppm NHDC) (Formula 4 of Table 11).

[00236] The method used to prepare the dark chocolate products in this test was as follows. Firstly, the 1% solution of NHDC in glycerol was prepared by gradually adding 1 g of NHDC to 99 g of glycerol, mixing and heating at 60°C for 15 minutes, until a clear solution was obtained. The solution was allowed to cool to room temperature. The dark chocolate was weighed and heated to 45°C and, when the chocolate was completely melted, powdered sugar and, optionally, also the 1% NHDC glycerol solution or the composition of Example B were added, and the mixture was then completely mixed. The mixture was heated until it reached 45°C, then allowed to cool to 30°C and then poured into molds (6 g/piece). The molds with the chocolate were placed in the refrigerator for faster hardening.

Example 9: Compositions to mask taste

[00237] Different compositions to mask the taste were prepared, such as complexes of neohesperidin dihydrochalcone with gamma-cyclodextrin (gCD) or beta-cyclodextrin (bCD), using different molar proportions, as described in Table 12. The NHDC was supplied by the company Ferrer HealthTech and cyclodextrins were supplied by Wacker TABLE 12

[00238] The sweetening compositions employed were in the form of a complex.

[00239] To prepare the complex of Example A, NHDC (14.0 g, 20.6 mmol) was added to a stirred solution of gCD (30 g, 20.6 mmol) in deionized water (500 ml). The mixture was stirred for one hour at 20-25°C, until complete dissolution. The solution was clarified through a 0.8 μm filter to remove insoluble particles. The solvent was removed under reduced pressure. An off-white solid (40 g) of the 1:1 complex was obtained.

[00240] To prepare the complex of Example B, NHDC (7.5 g, 11 mmol) was added to a stirred solution of gCD (47.7 g, 33 mmol) in deionized water (500 ml). The mixture was stirred for one hour at 20-25°C, until complete dissolution. The solution was clarified through a 0.8 μm filter to remove insoluble particles. The solvent was removed under reduced pressure. An off-white solid (54 g) of the 1:3 complex was obtained.

[00241] The NHDC-gCD complexes of Examples C, D and E were prepared under the same conditions described above for Examples A and B.

[00242] To prepare the complex of Example F, NHDC (7.0 g, 10.2 mmol) was added to a stirred solution of bCD (13.4 g, 10.2 mmol) in deionized water (900 ml) at 50°C. The mixture was stirred for two hours at 50°C, until complete dissolution. The solution was clarified through a 0.8 μm filter to remove insoluble particles. The solvent was removed under reduced pressure. An off-white solid (18.1 g) of the 1:1 complex was obtained.

[00243] To prepare the complex of Example G, NHDC (4.0 g, 5.8 mmol) was added to a stirred solution of bCD (22.9 g, 17.5 mmol) in deionized water (1500 ml ) at 50°C. The mixture was stirred for two hours at 50°C, until complete dissolution. The solution was clarified through a 0.8 μm filter to remove insoluble particles. The solvent was removed under reduced pressure. An off-white solid (23.9 g) of the 1:3 complex was obtained.

Example 10: Masking the bitterness of paracetamol

[00244] The bitter masking effect against paracetamol was tested. The anti-bitter effect was measured as a dose-response profile versus a paracetamol solution.

[00245] The following substances were tested: NHDC alone, gamma-cyclodextrin alone and compositions comprising NHDC and gamma-cyclodextrin in a molar ratio 1:3 (Example B), 1.5:1 (Example C), 1:6 ( Example D) and 1:10 (Example E).

[00246] To evaluate the masking effect of each substance, several aqueous solutions were prepared, each containing 5000 ppm of paracetamol and different concentrations of the tested substance, i.e., 5, 25, 50, 75 and 100 ppm.

[00247] A calibrated test panel compared each solution with various solutions of paracetamol in water at different concentrations and determined the equibitter paracetamol solution. The equibitter solution was calculated as the average of all panel evaluations.

[00248] The masking effect was then calculated from the reference amount of paracetamol contained in each tested solution (5000 ppm) and the amount of paracetamol in the equibitter solution, using the following formula (Formula III):

[00249] Thus, for example, a solution containing 5000 ppm paracetamol and 100 ppm NHDC was equivalent to a solution containing 3266.7 ppm paracetamol. Therefore, the masking effect was 34.67%.

[00250] In the same way, the masking effect for each substance at each concentration was calculated. The results are shown in Table 13. TABLE 13

[00251] To calculate the masking synergies between gamma-cyclodextrin and NHDC, first, for each amount of the combination (Examples A-E), using the molecular weight of each component, the amounts of gamma-cyclodextrin and NHDC contained therein were calculated. For example, 100 ppm of Example B contains 13.61 ppm NHDC and 86.39 ppm gamma cyclodextrin. Then, the antibacterial contribution of each component of the composition was calculated, based on the data in Table 13. For example, 13.61 ppm of NHDC provides 9.44% masking effect and 86.39 ppm of gamma-cyclodextrin provides 5.46% masking effect (the antibitizing effects of each specific concentration were calculated by interpolation of the data points in Table 13). Therefore, the expected masking effect is calculated as the sum of the contributions of each component. For example, the expected masking effect of 100 ppm from Example B is 14.90% (i.e., 9.44 plus 5.46).

[00252] Finally, the masking synergy is calculated using Formula IV:

[00253] The results corresponding to the composition of NHDC-gCD with a molar ratio of 1:3 are disclosed in Table 14. TABLE 14

[00254] The masking effect of Examples C (NHDC: gCD 1.5:1), D (NHDC: gCD 1:6) and (NHDC: gCD 1:10) was also evaluated. Aqueous solutions were prepared, each containing 5000 ppm of paracetamol and different concentrations of each of the tested Ex. EC formulations, that is, 25 and 50 ppm. The results are disclosed in Tables 15 to 17. TABLE 15 TABLE 16 TABLE 17

Example 11: Masking the bitterness of quinine

[00255] The bitter masking effect against quinine was tested, following a procedure analogous to that used in Example 10 for paracetamol.

[00256] The following substances were tested: NHDC alone, beta-cyclodextrin alone, a composition comprising NHDC and beta-cyclodextrin in a 1:1 molar ratio (Example F) and a composition comprising NHDC and beta-cyclodextrin in a 1 molar ratio :3 (Example G).

[00257] Analogous to Example 10, several aqueous solutions were prepared, each containing 250 ppm of quinine and different concentrations of the tested substance, namely 5, 25, 50, 75 and 100 ppm. For each solution tested, a test panel determined the equibitter quinine solution and the masking effect was calculated using a formula analogous to formula III (replacing 5000 with 259). The masking effects of each substance at each concentration tested are listed in Table 18. TABLE 18

[00258] The masking synergies between beta-cyclodextrin and NHDC in Examples F and G were calculated following a procedure analogous to that described in Example 10. Therefore, using the molecular weight of each component, the amounts of beta-cyclodextrin and NHDC contained in each quantity of the combinations of Examples F and G were calculated, and then the antibitizing contribution of each component was calculated based on the data in table 19. The expected masking effect was calculated as the sum of the contributions of each component, and finally , masking synergy was calculated (using Formula IV).

[00259] The results for Examples F and G are disclosed in Tables 19 and 20, respectively. TABLE 19 TABLE 20

Example 12: Masking the astringency of green tea extract

[00260] The astringency flavor masking capacity was measured using the same methodology disclosed for the bitter masking capacity (Examples 10 and 11).

[00261] The following substances were tested: a composition comprising NHDC and gamma-cyclodextrin in the molar ratio 1:3 (Example B) and a composition comprising NHDC and beta-cyclodextrin in the molar ratio 1:3 (Example G), as well as NHDC alone, gamma-cyclodextrin alone and beta-cyclodextrin alone. The evaluated taste maskers were dissolved in water, together with 5 ppm of green tea extract.

[00262] First, a calibrated taste panel compared a solution prepared with 30 ppm of Example G and 5 ppm of green tea extract to different basic solutions of green tea extract in water and determined the equally astringent base in the aqueous solution. Then, two solutions containing, respectively, the proportional amount of NHDC and beta-cyclodextrin contained in 30 ppm of Example G were prepared, together with 5 ppm of green tea extract, and the flavor panel determined the equally astringent base in the solution. aqueous for both solutions.

[00263] The masking effect for each substance was calculated using a formula analogous to Formula III (replacing 5000 with 5), and the astringency masking synergy between beta-cyclodextrin and NHDC in Example G was calculated using Formula IV.

[00264] The masking effects and astringency masking synergy between gamma-cyclodextrin and NHDC for 30 ppm of Example B were calculated analogously.

[00265] The results are shown in table 21: TABLE 21

Example 13: 1H NMR characterization of the NHDC:gCD complex

[00266] The composition of Example A is in the form of a complex with a molar ratio of 1:1 NHDC:gCD. It was prepared as described in Examples 1 and 9.

[00267] The 1H NMR spectrum of this complex was recorded in D2O at 400 MHz and is shown in Figure 5.

[00268] Furthermore, the 1H NMR of pure gamma-cyclodextrin in D2O at 400 MHz (Figure 6) and the 1H NMR of pure NHDC in deuterated DMSO (DMSO-d6) at 400 MHz (Figure 7) were also recorded and compared with the spectrum of the complex.

[00269] Table 22 below specifically shows the comparison in chemical shifts in the 1H NMR for protons H1 to H6 of pure gamma-cyclodextrin (Figure 6) versus the chemical shifts of the equivalent protons in the complex (Figure 5). Each proton in CD gamma is identified in the schematic formula shown in Figure 8. TABLE 22

[00270] It can be seen that there is a variation in the chemical changes in the complex compared to cyclodextrin alone (last column of the table).

[00271] Similarly, Table 23 below specifically shows the comparison in the chemical shifts in the 1H NMR for the protons of pure NHDC (Figure 7) versus the chemical shifts of the equivalent protons when the NHDC is part of the complex, in Example A (Figure 5). Each proton in NHDC is identified in the schematic formula in Figure 9. TABLE 23

[00272] It can be seen that there is a variation in chemical changes in the complex compared to NHDC alone (last column of the table).

[00273] Furthermore, it can also be seen that the H-6 and H-8 protons, which are chemically equivalent in pure NHDC, are differentiated in the complex of Example A. Furthermore, the protons in the methylene groups (CH2) in the positions 2 and 3, which appear as triplets in the 1H NMR of NHDC, appear as multiplets in the complex.

Claims (11)

1. Sweetener composition, characterized by the fact that it comprises neohesperidin dihydrochalcone and gamma-cyclodextrin, in which the molar ratio neohesperidin dihydrochalcone: gamma-cyclodextrin is between 1.5:1 and 1:10. 2. Composition, according to claim 1, characterized by the fact that the neohesperidin dihydrochalcone:gamma-cyclodextrin molar ratio is between 1.5:1 and 1:6. 3. Composition according to claim 1 or 2, characterized by the fact that the molar ratio neohesperidin dihydrochalcone: gamma-cyclodextrin is 1:1. 4. Composition according to claim 1 or 2, characterized by the fact that the molar ratio neohesperidin dihydrochalcone: gamma-cyclodextrin is 1 ± 0.1:1 ± 0.1. 5. Composition, according to claim 4, characterized by the fact that the molar ratio neohesperidin dihydrochalcone: gamma-cyclodextrin is 1 ± 0.05:1 ± 0.05. 6. Composition according to claim 1 or 2, characterized by the fact that the molar ratio neohesperidin dihydrochalcone: gamma-cyclodextrin is 1:3. 7. Composition according to claim 1 or 2, characterized by the fact that the molar ratio neohesperidin dihydrochalcone: gamma-cyclodextrin is 1 ± 0.1:3 ± 0.3. 8. Composition according to claim 7, characterized by the fact that the molar ratio neohesperidin dihydrochalcone: gamma-cyclodextrin is 1 ± 0.05: 3 ± 0.15. 9. Use of the sweetener composition, as defined in any one of claims 1 to 8, characterized by the fact that it is to sweeten an ingestible product. 10. Use according to claim 9, characterized in that the ingestible product is selected from a food product and a pharmaceutical product. 11. Ingestible product, characterized by the fact that it comprises the sweetener composition, as defined in any one of claims 1 to 8.