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Stevia Extract I US 20110091637A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2011/0091637 A1 Abelyan et al. (43) Pub. Date: Apr. 21, 2011 (54) HIGH-PURITY REBAUDIOSIDE D AND Publication Classi?cation LOW-CALORIE CHOCOLATE CONTAINING THE SAME (51) Int. Cl. A23G 1/40 (2006.01) (75) Inventors: Varuzhan Abelyan, Kuala Lumpur (MY); Avetik Markosyan, Kuala Lumpur (MY); Lidia Abelyan, (52) US. Cl. ...................................................... .. 426/631 Kuala Lumpur (MY) (73) Assignee: PureCircle Sdn Bhd, Negeri Semb?an (MY) (57) ABSTRACT 21 A 1. N .._ 12/785 507 The invention P rovides methods of P urifyin g RebaudiosideD ( ) pp 0 ’ from the Slevia rebaudiana Bertoni plant extract along With (22) Filed: May 24, 2010 Rebaudioside A. The methods are useful for producing high purity Rebaudioside D and Rebaudioside A. The invention Related US. Application Data further provides a loW-calorie chocolate containing the puri (63) Continuation-in-part of application No, 12/580,233, ?ed Rebaudioside D and a process for making the low-calorie ?led on Oct 15, 2009 chocolate containing the puri?ed Rebaudioside D. Stevia Extract I - Absolute ethanol; - Water; ~ Heating; - Complete dissolving; - Cooling; - Starter of Rebaudioside A; - Aging; - Heating; - Cooling; - Aging. Suspension of Glycosides - centri?lgation; - Washing wth ethanol. or or R?baudloslde A Remaining Solution - Ethanoi/ t ' ' ' ' _ suspensi‘gz. e1 Soiuilon, - Evaporation of ethanol; “ Heating. , - Concentration; - Washmg- _ a with_ agitation;. I ~ Spray drying. - Cooling; . “ Washing with agitation. Mixture of Stevio] Glycosides » Cennifugation; - Washing wth ethanol; ~ Drying. Highly Puri?ed Rebaudioside A Patent Application Publication Apr. 21, 2011 Sheet 2 0f 11 US 2011/0091637 A1 Stevioside FIGZ Patent Application Publication Apr. 21, 2011 Sheet 3 0f 11 US 2011/0091637 A1 Rebaudioside B Patent Application Publication Apr. 21, 2011 Sheet 4 0f 11 US 2011/0091637 A1 Rebaudioside D FIG 2 (Cont’d) Patent Application Publication Apr. 21, 2011 Sheet 5 0f 11 US 2011/0091637 A1 Rebaudioside E m; 2 (Cunt’d) Patent Application Publication Apr. 21, 2011 Sheet 6 0f 11 US 2011/0091637 A1 Dulcoside A FIG 2 (Cont’d) Patent Application Publication Apr. 21, 2011 Sheet 7 0f 11 US 2011/0091637 A1 cHzoH ‘¢=o 0H Steviolbioside HOE-2 Rubugoside 2 (contid) Patent Application Publication Apr. 21, 2011 Sheet 8 of 11 US 2011/0091637 A1 Stevia Extract - Absolute ethanol; - Water; ~ Heating; - Complete dissolving; - Cooling; - Starter of Rebaudioside A; - Aging; ~ Heating; ' Cooling; - Aging. Suspension of Glycosides - Centri?igation; - Washing wth ethanol. or or Rebaudioside A ‘ Remaining Solution - Ethanol/water solution; _ Evaporation 9f ethanol; -:I11Spf1mi0n; - Concentmtion; “ eaung; ~ Spraydryin - - Washing with agitation; g ~ Cooling; . r . m Washing with agitation. Mixture of Steviol G13 cosides - Centrifugation; - Washing wth ethanol; - Drying. Highly Pun'?ed Rebaudioside A FIG 3 Patent Application Publication Apr. 21, 2011 Sheet 9 0f 11 US 2011/0091637 A1 (A) (B) RebA / 95.6% RebA / 52.7% RebD / 43.9% /3.5% (C) RebD 95.0% FIG 4 Patent Application Publication Apr. 21, 2011 Sheet 10 of 11 US 2011/0091637 A1 Stevia Extract i Precipitation of Rebaudioside A i Separation + i’ i Rebaudiioside A (~95-96%) Remaining solution Alcohol‘I tratment Evaporation Separation i Concentration i i High purity High Rebaudioside D Drying Rebaudioside A (>99%) Fraction Stevio! Glycosides Mixture Evaporation i Drying RebD Concentrate FIG 5 Patent Application Publication Apr. 21, 2011 Sheet 11 0f 11 US 2011/0091637 A1 16 -3. sobo 2000 i000 Wavenumbers (cm-1) FIG6 US 2011/0091637 A1 Apr. 21, 2011 HIGH-PURITY REBAUDIOSIDE D AND hydroxyphenyl)propyl]-L-0t-aspartyl]-phenylalanine LOW-CALORIE CHOCOLATE CONTAINING 1-methyl ester, salts thereof, and the like, and combination THE SAME thereof. [0009] Non-limiting examples of natural high intensity RELATED APPLICATIONS sweeteners include Stevioside, Rebaudioside A, Rebaudio side B, Rebaudioside C, Rebaudioside E, Rebaudioside F, [0001] This application is a continuation-in-part applica Steviolbioside, Dulcoside A, Rubusoside, mogrosides, tion of Us. patent application Ser. No. 12/580,233, ?led Oct. braZZein, neohesperidin dihydrochalcone (NHDC), glycyr 15, 2009. rhiZic acid and its salts, thaumatin, perillartine, pemandulcin, mukuroZiosides, baiyunoside, phlomisoside-I, dimethyl FIELD OF THE INVENTION hexahydro?uorene-dicarboxylic acid, abrusosides, perian [0002] The invention relates to a process for isolation and drin, camosi?osides, cyclocarioside, pterocaryosides, poly puri?cation of individual sweet glycosides from Slevia podoside A, braZilin, hemandulcin, phillodulcin, rebaudiana Bertoni plant extract, and more particularly to glycyphyllin, phloriZin, trilobatin, dihydro?avonol, dihydro isolation and puri?cation of Rebaudioside D from Slevia quercetin-3-acetate, neoastilibin, trans-cinnamaldehyde, rebaudiana Bertoni plant extract and further to low-calorie monatin and its salts, selligueain A, hematoxylin, monellin, chocolate sweetened with high intensity sweetener. osladin, pterocaryoside A, pterocaryoside B, mabinlin, pen tadin, miraculin, curculin, neoculin, chlorogenic acid, DESCRIPTION OF THE RELATED ART cynarin, siamenoside and others. [0010] High intensity sweeteners can be derived from the [0003] Sweeteners are critical ingredients in food supply. The demand of healthy low calorie beverages and food prod modi?cation of natural high intensity sweeteners, for ucts results in the increasing consumption of sweeteners; thus example, by fermentation, enZymatic treatment, or derivati Zation. there is a need to reduce the calories contributed by sweeten [0011] At present about eleven high intensity sweeteners ers. This goal can be achieved by using high intensity sweet are used worldwide. These are acesulfame-K, alitame, aspar eners. [0004] High intensity sweeteners possess sweetness level tame, cyclamate, glycyrrhiZin, NHDC, saccharin, Stevioside, many times exceeding that of sucrose. They are essentially sucralose, thaumatin, neotame, and Rebaudioside A. non-caloric and used widely in manufacturing of diet and [0012] The high intensity sweeteners can be grouped into reduced calorie food. Although natural caloric sweetener three generations. The ?rst generation represented by cycla mate, glycyrrhiZin and saccharin has a long history of use in such as sucrose, fructose, and glucose provide the most desir able taste to consumers, they are caloric. High intensity food. The second generation includes acesulfame-K, aspar sweeteners do not affect the blood glucose level and provide tame, NHDC and thaumatin. Alitame, neotame, sucralose, Stevioside, and Rebaudioside A belong to the third genera little or no nutritive value. [0005] However, high intensity sweeteners that generally tion. are used as sucrose substitutes possess taste characteristics [0013] The standard sweetening power associated with different than that of sugar, such as sweet taste with different each high intensity sweetener is given in TABLE 1. However, temporal pro?le, maximal response, ?avor pro?le, mouth when they are used in blends, the sweetening power can feel, and/or adaptation behavior than that of sugar. For change signi?cantly. example, the sweet taste of some high-potency sweeteners is slower in onset and longer in duration than that of sugar and TABLE 1 thus changes the taste balance of a food composition. Because Sweetener Sweetness power of these differences, usage of high-potency sweetener in replacing such a bulk sweetener as sugar in a food or beverage Saccharose 1 causes an unbalanced temporal and/or ?avor pro?le. If the AcesulfaIne-K 200 Alitalne 2000 taste pro?le of high-potency sweeteners could be modi?ed to Aspartame 200 impart desired taste characteristics, it can provide low calorie Cyclamate 30 beverages and food products with taste characteristics more Glycyrrhizin 50 desirable for consumers. NHDC 1000 saccharine 300 [0006] On the other hand, high-potency sweeteners may Stevioside 200 have some cost and functional advantages compared to sugar. Rebaudioside A 450 The competition among sugar and non-sugar high-potency Thaurnatin 3000 sweeteners is tough in soft drinks industry, in countries where Sucralose 600 their use and production is permitted and also in countries with overvalued sugar prices. [0014] On the other hand, ‘natural’ and ‘organic’ foods and [0007] At present high intensity sweeteners are used world beverages have become the “hottest area” in the food indus wide. They can be of both synthetic and natural origin. try. The combination of consumers’ desire, advances in food [0008] Non-limiting examples of synthetic sweeteners technology, new studies linking diet to disease and disease include sucralose, potassium acesulfame, aspartame, alitame, prevention has created an unprecedented opportunity to saccharin, neohesperidin dihydrochalcone synthetic deriva address public health through diet and lifestyle. tives, cyclamate, neotame, dulcin, suosan, N-[N-[3-(3 -hy [0015] A growing number of consumers perceive the abil droxy-4-methoxyphenyl)propyl]-L-(x-aspartyl]-L-phenyla ity to control their health by enhancing their current health lanine 1-methyl ester, N-[N- [3 -(3 -hydroxy-4 and/or hedging against future diseases. This creates a demand methoxyphenyl) -3 -methylbutyl] -L-0t-aspartyl] -L for food products with enhanced characteristics and associ phenylalanine 1-methyl ester, N-[N-[3-(3-methoxy-4 ated health bene?ts, speci?cally a food and consumer
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