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Rebaudioside X to Provide Sweetness Enhancement Rebaudiosid X Für Intensivere Süsse Rébaudioside X Pour Accentuer La Sucrosité

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Rebaudioside X to Provide Sweetness Enhancement Rebaudiosid X Für Intensivere Süsse Rébaudioside X Pour Accentuer La Sucrosité (19) TZZ¥Z___T (11) EP 3 019 197 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: A61K 47/36 (2006.01) C07H 15/24 (2006.01) 28.08.2019 Bulletin 2019/35 A23L 2/60 (2006.01) A23L 27/30 (2016.01) (21) Application number: 14822472.8 (86) International application number: PCT/US2014/046499 (22) Date of filing: 14.07.2014 (87) International publication number: WO 2015/006763 (15.01.2015 Gazette 2015/02) (54) REBAUDIOSIDE X TO PROVIDE SWEETNESS ENHANCEMENT REBAUDIOSID X FÜR INTENSIVERE SÜSSE RÉBAUDIOSIDE X POUR ACCENTUER LA SUCROSITÉ (84) Designated Contracting States: (74) Representative: Dehns AL AT BE BG CH CY CZ DE DK EE ES FI FR GB St. Bride’s House GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO 10 Salisbury Square PL PT RO RS SE SI SK SM TR London EC4Y 8JD (GB) (30) Priority: 12.07.2013 US 201361845812 P (56) References cited: 25.09.2013 US 201314036654 WO-A1-2013/092657 WO-A1-2013/096420 WO-A1-2013/096420 WO-A2-2013/022989 (43) Date of publication of application: US-A1- 2008 102 162 US-A1- 2009 004 360 18.05.2016 Bulletin 2016/20 US-A1- 2010 092 638 US-A1- 2011 160 311 US-A1- 2011 160 311 US-A1- 2013 064 955 (73) Proprietor: The Coca-Cola Company US-A1- 2013 136 839 Atlanta, GA 30313 (US) • MASAYA OHTA: "Characterization of Novel (72) Inventors: Steviol Glycosides from Leaves of Stevia • PRAKASH, Indra rebaudiana Morita", J. APPL. GLYCOSCI., vol. 57, Alpharetta, GA 30022 (US) 17 August 2010 (2010-08-17), pages 199-209, • CAMPBELL, Mary XP055121080, DOI: 10.5458/jag.57.199 Acworth, GA 30101 (US) • HIGIRO, Juvenal Atlanta, GA 30345 (US) Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 3 019 197 B1 Printed by Jouve, 75001 PARIS (FR) EP 3 019 197 B1 Description CROSS REFERENCE TO RELATED APPLICATIONS 5 [0001] This application claims priority to U.S.S.N. 14/036654, filed September 25, 2013, and U.S.S.N. 61/845,812, filed July 12, 2013. FIELD OF THE INVENTION 10 [0002] The present invention relates to beverages comprising at least one sweetener and rebaudioside X. The present invention also relates to methods for enhancing the sweetness of beverages using rebaudioside X. BACKGROUND OF THE INVENTION 15 [0003] Natural caloric sugars, such as sucrose, fructose and glucose, are utilized to provide a pleasant taste to bev- erages, foods, pharmaceuticals, oral hygienic and cosmetic products. Sucrose, in particular, imparts a taste preferred by consumers. Although sucrose provides superior sweetness characteristics, it is caloric. Non-caloric or low caloric sweeteners have been introduced to satisfy consumer demand. However, sweeteners within this class differ from natural caloric sugars in ways that consumers do not perceive the same taste quality. On a taste basis, non-caloric or low caloric 20 sweeteners exhibit a temporal profile, maximal response, flavor profile, mouth feel, and/or adaptation behavior that differ fromsugar. Specifically,non-caloric or low caloricsweeteners exhibit delayed sweetness onset,lingering sweet aftertaste, bitter taste, metallic taste, astringent taste, cooling taste and/or licorice-like taste. On a source basis, many non-caloric or low caloric sweeteners are synthetic chemicals. The desire for a natural non-caloric or low caloric sweetener that tastes like sucrose remains high. 25 [0004] Stevia rebaudiana Bertoni is a perennial shrub of the Asteraceae (Compositae) family native to certain regions of South America. Its leaves have been traditionally used for hundreds of years in Paraguay and Brazil to sweeten local teas and medicines. The plant is commercially cultivated in Japan, Singapore, Taiwan, Malaysia, South Korea, China, Israel, India, Brazil, Australia and Paraguay. [0005] The leaves of the plant contain diterpene glycosides in an amount ranging from about 10 to 20% of the total 30 dry weight. These diterpene glycosides are about 150 to 450 times sweeter than sugar. Structurally, the diterpene glycosides are characterized by a single base, steviol, and differ with respect to the presence of carbohydrate residues at positions C13 and C19. Typically, on a dry weight basis, the four major steviol glycosides are Dulcoside A (0.3%), Rebaudioside C (0.6-1.0%), Rebaudioside A (3.8%) and Stevioside (9.1%). Other steviol glycosides identified in Stevia extract include Rebaudioside B, D, E, and F, Steviolbioside and Rubusoside. Among these, only Stevioside and Rebau- 35 dioside A are available on a commercial scale. [0006] US 2011/0130311 discloses sweetener compositions comprising at least one sweetener and at least one sweetness enhancer chosen from terpenes, flavonoids, amino acids, proteins, polyols, other known natural sweeteners, secodammarane glycosides, and analogues thereof, wherein the at least one sweetness enhancer is present in the composition in an amount at or below the sweetness threshold level of the sweetness enhancer. 40 [0007] Ohta et al, J.Glycosci., 57, 199-209 (2010) discloses compounds resulting from the extraction with hot water from leaves of Stevia Rebaudiana Morita. [0008] US 2010/0092638 discloses sweetened consumables that comprise certain sweeteners and at least one sweet- ness enhancer in a concentration near its sweetness detection threshold. [0009] To date, the use of steviol glycosides has been limited by certain undesirable taste properties which become 45 even more prominent at increased concentration, including licorice taste, bitterness, astringency, sweet aftertaste, bitter aftertaste and licorice aftertaste. These undesirable taste attributes are exaggerated in carbonated beverages, where full replacement of sugar requires particular high concentrations of steviol glycosides, e.g., exceeding 500 mg/L. Overall use of steviol glycosides at such high concentrations results in significant deterioration in taste of the final product. [0010] Accordingly, there remains a need to address the taste issues of natural sweeteners and reduce caloric content 50 of compositions containing traditional sweeteners. SUMMARY OF THE INVENTION [0011] The present invention is directed to a beverage comprising at least one sweetener and rebaudioside X, wherein 55 the at least one sweetener is selected from the group consisting of sucrose and high fructose corn syrup, and the at least one sweetener is present in a concentration above its sweetness recognition threshold, rebaudioside X is present in a concentration from about 20 ppm to about 30 ppm, and rebaudioside X enhances the sweetness of the beverage by an amount more than the detectable sweetness of a solution containing the same concentration or rebaudioside X 2 EP 3 019 197 B1 in the absence of the at least one sweetener. [0012] In one embodiment rebaudioside X enhances the sweetness by about 1.0% (w/v) sucrose equivalence or greater, such as, for example, about 1.5% (w/v) or greater. In another embodiment, rebaudioside X enhances the sweetness of the beverage from about 1.0% to about 3.0% (w/v) sucrose equivalence. 5 [0013] The present invention also provides a method for enhancing the sweetness of beverages comprising at least one sweetener selected from the group consisting of sucrose and high fructose corn syrup in a concentration above its sweetness recognition threshold, comprising adding rebaudioside X to the beverage in a concentration from about 20 ppm to about 30 ppm, wherein the rebaudioside X enhances the sweetness of the beverage by an amount more than the detectable sweetness of a solution containing the same concentration of rebaudioside X. 10 [0014] In one embodiment, rebaudioside X enhances the sweetness by about 1.0% (w/v) sucrose equivalence or greater. [0015] In preferred embodiments, the rebaudioside X has a purity greater than about 80% by weight in a Stevia extract or mixture of steviol glycosides. In a preferred embodiment, the rebaudioside X has a purity greater than about 95%. [0016] The beverage of the present invention may further comprise one or more additional functional ingredients and/or 15 additives. [0017] In some embodiments, the beverage is a reduced-calorie beverage, such as a mid- or low-calorie beverage. BRIEF DESCRIPTION OF THE FIGURES 20 [0018] 13 FIG. 1: illustrates the C NMR spectrum of Reb X (150 MHz, C 5D5N). 1 FIG. 2: illustrates the H NMR spectrum of Reb X (600 MHz, C 5D5N). 1 1 FIG. 3: illustrates the H- H COSY spectrum of Reb X (600 MHz, C5D5N). 25 FIG. 4: illustrates the HMBC spectrum of Reb X (600 MHz, C5D5N). DETAILED DESCRIPTION OF THE INVENTION [0019] Recently, rebaudioside X, 13-[(2-O-β-D-glucopyranosyl-3-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy] ent 30 kaur-16-en-19-oic acid-[(2-O-β-D-glucopyranosyl-3-O-β-D-glucopyranosyl-β-D-glucopyranosyl) ester], was isolated from Stevia rebaudiana and characterized: 35 40 45 50 55 [0020] Rebaudioside X is present in minute quantities in Stevia rebaudiana, about 0.05-0.5% by weight. Methods of isolating rebaudioside X are disclosed in WO2013/096420. [0021] Rebaudioside X (also referred to as rebaudioside M) is also commercially available from Chromadex. 3 EP 3 019 197 B1 [0022] The present invention is based on the discovery that rebaudioside X acts as a sweetness enhancer when used in certain concentrations in compositions, e.g. beverages, containing traditional caloric sweeteners. Advantageously, the present invention allows for the reduction of the amount of caloric sweetener(s) used in said compositions.
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