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WO 2014/000755 Al 3 January 2014 (03.01.2014) P O P C T (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2014/000755 Al 3 January 2014 (03.01.2014) P O P C T (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every A23L 1/236 (2006.01) A23L 1/22 (2006.01) kind of national protection available): AE, AG, AL, AM, A23L 2/60 (2006.01) A23L 2/56 (2006.01) AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, (21) Number: International Application DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, PCT/EP2012/004079 HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, (22) International Filing Date: KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, 28 September 2012 (28.09.2012) ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, (25) Filing Language: English RW, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, (26) Publication Language: English TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (30) Priority Data: 12004804.6 27 June 2012 (27.06.2012) (84) Designated States (unless otherwise indicated, for every 61/664,887 27 June 2012 (27.06.2012) kind of regional protection available): ARIPO (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, (71) Applicant: NUTRINOVA NUTRITION SPECIALTIES UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, & FOOD INGREDIENTS GMBH [DE/DE]; Indus- TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, triepark Hochst, 65929 Frankfurt am Main (DE). EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, (72) Inventors: PUTTER, Clements M.; Vensteeg 13, NL-541 TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, 1AR Zeeland (NL). WONSCHIK, Johann; Riepenbrik ML, MR, NE, SN, TD, TG). 16, 37647 Brevorde (DE). Published: (74) Agent: LAHRTZ, Fritz; Isenbruck Bosl Horschler LLP, Patentanwalte, PrinzregentenstraBe 68, 81675 Munchen — with international search report (Art. 21(3)) (DE). (54) Title: TASTE-MASKING COMPOSITIONS, SWEETENER COMPOSITIONS AND CONSUMABLE PRODUCT COM- POSITIONS CONTAINING THE SAME (57) Abstract: The present invention relates to novel compositions X comprising following substances: (1) L-valine; (2) maltol; (3) naringin; (4) maltodextrine MD 14 (5) arabicgum (spraygum); (6) acetoin; (7) delta dodecalactone; (8) delta decalactone; and (9) massoia lactone; to the use of the compositions X for modifying, masking, reducing and/or suppressing an unpleasant off-taste, after taste or lingering sweetness of at least one sweetener, sweetness enhancer or consumable product; and to a process for the prepara - o tion of the compositions X. Further, the invention relates to sweetener compositions comprising at least one sweetener and the novel compositions X; to a method of providing sweetener or sweetness enhancer compositions; to methods of modifying, masking, redu- cing and/or suppressing an unpleasant off-taste, aftertaste or lingering sweetness of at least one sweetener or sweetness enhancer; and to tabletop sweetener compositions comprising the novel compositions X. The invention also relates to consumable product compositions comprising a consumable product and the novel compositions X; to methods of modifying, masking, reducing and/or suppressing an unpleasant off-taste, aftertaste or lingering sweetness of a consumable product composition; and to methods of im- parting rich taste to a consumable product. Taste-Masking Compositions, Sweetener Compositions and Consumable Product Compositions Containing the Same Field of the Invention The present invention relates to novel compositions X comprising following substances: (1) L-valine; (2) maltol; (3) naringin; (4) maltodextrine MD 14 (5) arabicgum (spraygum); (6) acetoin; (7) delta dodecalactone; (8) delta decalactone; and (9) massoia lactone; to the use of the compositions X for modifying, masking, reducing and/or suppressing an unpleasant off-taste, aftertaste or lingering sweetness of at least one sweetener, sweetness enhancer or consumable product; and to a process for the preparation of the compositions X. Further, the invention relates to sweetener compositions comprising at least one sweetener and the novel compositions X; to a method of providing sweetener or sweetness enhancer compositions; to methods of modifying, masking, reducing and/or suppressing an unpleasant off-taste, aftertaste or lingering sweetness of at least one sweetener or sweetness enhancer; and to tabletop sweetener compositions comprising the novel compositions X. The invention also relates to consumable product compositions comprising a consumable product and the novel compositions X; to methods of modifying, masking, reducing and/or suppressing an unpleasant off-taste, aftertaste or lingering sweetness of a consumable product composition; and to methods of imparting rich taste to a consumable product. Background of the Invention Consumable products with a high content of sugar(s), e.g., sucrose (saccharose), glucose, fructose and/or mixtures thereof, are generally afforded much greater preference by consumers due to their sweetness. However, it is commonly known that a high content of sugar(s) can greatly increase the blood sugar level, lead to the formation of fatty deposits and ultimately result in health problems such as childhood obesity, type II diabetes, and related illnesses. Therefore, it has long been an aim to reduce the sugar content of consumable products to the absolute minimum necessary. One way to reduce sugar content is to replace at least a portion of the sugar(s) with one or more non-caloric high-intensity sweeteners. These non-caloric sweeteners provide sweetnesses significantly higher than those of conventional sweeteners, e.g., sugars such as sucrose or high-fructose corn syrup (HFCS). However, unlike conventional sugars, many of the non-caloric or low-caloric sweeteners have unpleasant taste features, e.g., off-tastes, aftertastes and/or lingering sweetness. These off-tastes, aftertastes and/or lingering sweetnesses negatively affect the overall flavor of the respective consumable product to which they are added. For example, sucralose, stevioside and cyclamate contribute to negative time-intensity profiles. As another example, acesulfame potassium, saccharin and stevioside, produce a bitter and/or astringent aftertaste. As another example, neotame produces a bitter and metallic off-taste. As another example, glycyrrhinzinic acid ammonium salt produces marked additional aroma impression. Also, some sweeteners, e.g., brazzein, monellin, thaumatin, are not particularly stable under heat. Others, e.g., aspartame, are not stable in all applications. As another example, saccharin may have a very long-lasting sweetening effect, e.g., a lingering sweetness. Steviol glycosides occur naturally in Stevia spp. or Rubus spp. Examples of these include dulcoside, rebaudiosides A-H, rubusoside, stevioside, suaviosides A, B and G-J. Steviol glycosides are very good sweeteners, but, when used in concentrations necessary for an adequate sweetening effect, steviol glycosides often exhibit a liquorice-like and/or bitter and/or astringent taste impression. Further unpleasant taste impressions may also be observed, e.g., a long-lasting aftertaste or a sweetener like taste profile. In particular, when used in beverages, e.g., sweet, calorie-free or very low calorie drinks, such sweeteners may exhibit unpleasant secondary taste impressions and/or aftertastes and may lower the sensory acceptance. As such, these negative taste features often require taste masking. Some taste-masking substances are known. Although many conventional taste-masking substances may partially modify, mask, reduce and/or suppress unpleasant taste features of specific sweeteners or sweetness enhancers, many taste-masking substances are severely limited in their application. For example, US 2004/0142084 Al describes alkaline metal hydrogen sulphates as masking agents. One disadvantage of these sulphates is that they considerably increase the acid content in the consumable product. As another example, US 3,924,017 discloses the use of caffeic acid as masking agent. As is known in the art, one disadvantage of using caffeic acid is that caffeic acid itself has a slightly bitter taste and easily suppresses the sweetness, so that more sweetener would have to be used. Further, US 2002/01 77576 Al describes the suppression of a bitter taste by nucleotides, for example cytidine 5'-monophosphates (CMPs). The disadvantage of using CMPs is that the strongly polar compounds can only be used in strongly polar solvents. Therefore, CMPs can be used to only a very limited degree in many fat-containing consumable products. Furthermore, the availability of CMPs is severely limited because of their expensive chemical synthesis. Thus, there is a need for further taste-masking compositions that can modify, mask, reduce and/or suppress unpleasant taste features left by sweeteners or sweetness enhancers without demonstrating the disadvantages of known taste-masking substances. Summary of the Invention The present invention in one aspect, relates to a composition X comprising the following substances: (1) L-valin; (2) maltol; (3) naringin; (4) maltodextrine MD 14 (5) arabicgum (spraygum); (6) acetoin; (7) delta dodecalactone; (8) delta decalactone; and (9) massoia lactone. In one embodiment, the composition X further comprises the following substance: (10) diacetyl. In one embodiment, at least one of the substances (1) to (10) is of natural origin. In one embodiment, all of the substances (1) to (10) are of natural origin. In a further embodiment, all of the substances (1) to (10) apart from substances (4) and (5) are of natural origin. In one embodiment, massoia lactone (9) is (i?)-5,6-dihydro-6-pentyl-2 H-pyran-2-one. In one embodiment, the substance (1) is present in the composition X in an amount ranging from 0.01 wt% to 0.09 wt%.
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