巴西专利BR112013014589B1 METHOD FOR PREPARING A HIGHLY SOLUBLE REBAUDIOSIDE COMPOSITION

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专利摘要:
The invention relates to a process for producing highly soluble compositions containing purified steviol glycosides from bertoni rebaudian stevia plant extract, more particularly rebaudioside d. The highly soluble compositions obtained are useful as non-caloric sweeteners or in combination with sugar or high intensity sweeteners in edible and chewable compositions such as in beverages, confectionery, bakery products, chewing gums and the like.
公开号:BR112013014589B1
申请号:R112013014589-7
申请日:2011-12-12
公开日:2019-04-02
发明作者:Avetik Markosyan；Siddhartha PURKAYASTHA
申请人:Purecircle Usa Inc.；
IPC主号:

专利说明:

“METHOD FOR PREPARING A HIGHLY SOLUBLE REBAUDIOSIDE COMPOSITION”
Information on previous patent applications [001] This patent application is entitled to previous filing dates from, and claims priority benefit from, US Provisional Patent Application No. 61 / 422,403, filed on December 13, 2010, and US Provisional Patent Application No. 61 / 424,798, filed on December 20, 2010, its content being incorporated here in its entirety by reference.
Field of the Invention [002] The invention relates to the production of highly soluble compositions containing purified Esteviol glycosides from plant extract Stevia rebaudiana Bertoni, more particularly Rebaudioside D.
Fundamentals of the Invention [003] High intensity sweeteners have a degree of sweetness several times higher than that of sucrose. They are essentially non-caloric and widely used in diet manufacturing and reducing the calorie content of foods. Although natural caloric sweeteners; such as sucrose, fructose and glucose provide consumers with a more desirable taste, they have high calorie values. High-intensity sweeteners do not affect the blood glucose level and provide little or no nutritional value.
[004] Stevia rebaudiana Bertoni is a perennial shrub of the Asteraceae family (Compositae) family native to certain regions of South America. The leaves of the plant contain 10 to 20% of diterpene glycosides, which are about 150-450 times more sweets than sugar. The leaves have been traditionally used for hundreds of years in Paraguay and Brazil to sweeten local teas and medicines.
[005] Currently, there are more than 230 species of Stevia with significant sweetening properties. The plant has been successfully cultivated in a wide range of conditions from its native subtropical condition to the cold northern latitudes.
[006] The extract of the plant Stevia rebaudiana contains a mixture of different sweet diterpene glycosides, which have a single base - Steviol - and differ in the presence of carbohydrate residues in positions C13 and C19. These
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2/16 glycosides accumulate on the leaves of Stevia and make up about 10% - 20% of the total dry weight. Typically, on a dry weight basis, the four main glycosides found in Stevia leaves are Dulcoside A (0.3%), Rebaudioside C (0.6-1.0%), Rebaudioside A (3.8%) and Stevioside (9.1%). Other glycosides identified in the Stevia extract include Rebaudioside B, C, D, E, and F, Steviolbioside and Rubusoside. Among the steviol glycosides only stevioside and rebaudioside A are available on a commercial scale.
[007] Steviol glycosides have zero calories and can be used whenever sugar is used. They are ideal for diabetics and low calorie diets. In addition, sweet Steviol glycosides have functional and sensory properties superior to those of many high potency or high intensity sweeteners.
[008] Rebaudiosídeo D (CAS: 63279-13-0), as shown in Figure 1, is one of the sweet glycosides found in Stevia rebaudiana. Studies show that the highly purified forms of Rebaudioside D have a very desirable taste profile, almost without bitterness and persistent licorice flavor typical of other Steviol glycosides.
[009] These properties multiply the significance of Rebaudioside D and attract great interest in the preparation methods of Rebaudioside D forms. However, highly purified Steviol glycosides have relatively low water solubility. For example, the solubility in thermodynamic equilibrium of Reubaudioside A at room temperature is only 0.8%.
[010] On the other hand, it is well known that Rebaudioside A presents the so-called polymorphism (Zell TM, Padden BE. Grant DJW, Schroeder SA, Wachholder KL, Prakash I, Munsona EJ (2000) Investigation of Polymorphism in Aspartame and Neotami Using Solid -State NMR Spectroscopy, Tetrahedron, 56, 6603-6616). The amorphous, anhydrous and solvate forms of Rebaudioside A differ significantly from each other in terms of solubility; which is one of the main criteria for the commercial viability of a sweetener. In this regard, as shown in Table 1, the hydrate form of Rebaudioside A exhibits the lowest solubility (Prakash I, DuBois GE, Clos JF, Wilkens KL, Fosdick LE (2008) Development of rebiana, a natural, non-caloric sweetener , Food Chem. Toxicol, 46, S75-S82). It has been shown that Rebaudioside
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A can change from one polymorph to another under certain conditions (U.S. Patent. Appl. 11/556, 049).
Table 1
Properties of Rebaudioside A forms (U.S. Patent Application No.
11 / 556,049)
Polymorphic formsForm 1 hydrate Anhydrous Form 2 Form 3 solvate Amorphous shape 4 Dissolution rate in H2O at 25 ° C Very low (<0.2% in 60 minutes) Intermediate(<30% in 5 minutes) High (> 30% in5 minutes) High (<35% in5 minutes) Alcohol content <0.5% <1% 1 -3% <0.05% Moisture content > 5% <1% <3% 6.74% [011] The Rebaudiosídeo D has even lower water solubility in
compared to Rebaudioside A. At room temperature it can be dissolved only at 0.05%. When heat is applied, up to 0.5% solution can be made, but when cooling to room temperature, Rebaudioside D will quickly separate from the solution by crystallization. Considering the high sweetness intensity of Rebaudioside D, even 0.05% solubility can be sufficient for many applications.
[012] Many food production processes use highly concentrated mixtures of ingredients before producing the final formations of food products. In this case, higher concentrations of Rebaudioside D will be necessary. It should be noted that the use of heat to dissolve Rebaudioside D may not be possible in many compositions that contain heat sensitive components. Also, maintaining the mixture at high temperatures for an extended period of time to avoid premature crystallization of Rebaudioside D can cause thermal degradation of the components of the mixture or undesirable changes in organoleptic properties.
[013] Therefore, there is a need for the development of highly soluble forms or compositions of Rebaudioside D that can provide stable solutions with treatment with minimal or no heat treatment.
[014] Furthermore, considering the similar chemical structures of Rebaudioside D and the other glycosides Steviol, as well as other glycosides
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4/16 terpene, the developed approaches can be used in the case of other glycosides as well.
Summary of the Invention [015] The invention relates to a process for the production of highly soluble compositions containing purified Esteviol glycosides from plant extract Estevia rebaudiana Bertoni, more particularly Rebaudioside D.
[016] Hereinafter the term “steviol glycoside (s)” means Rebaudioside A, Rebaudioside B, Rebaudioside C, Rebaudioside D, Rebaudioside E, Rebaudioside F, stevioside, Steviolbioside, dulcoside A, Rubusoside or other Steviol glycoside and combinations thereof.
[017] Hereinafter, unless otherwise specified, the solubility of the material is determined in water in OR (reverse osmosis) at room temperature. When the solubility is expressed as "%" it is to be understood as the number of grams of material soluble in 100 grams of solvent.
[018] Hereinafter, the term “highly purified” means a purity level of at least 95% (w / w) on an anhydrous basis.
[019] Hereinafter the term "low purity" means a degree of purity of less than 95% (w / w) in relation to the anhydrous product.
[020] Hereinafter, the term “GET content” means Total Steviol Glycoside content, and will be calculated as the sum of total Steviol glycoside contents including Rebaudioside A, Rebaudioside B, Rebaudioside C, Rebaudioside D, Rebaudioside E, Rebaudioside F, Stevioside, Steviolbioside, Dulcoside A and Rubusoside.
[021] Hereinafter the terms “Reb A, B, C, D, E, F” refer to Rebaudioside A, B, C, D, E, F, respectively.
[022] Hereinafter the term "Reb D" refers to Rebaudioside D (CAS No. 63279-13-0).
[023] Hereinafter the term "crystalline Rebaudioside D" refers to any form of highly purified Rebaudioside D obtained by crystallization from an aqueous or alcoholic aqueous solution containing Rebaudioside D and subsequent separation of the Rebaudioside D crystals and drying them by any means known in the art.
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5/16 [024] Hereinafter the term "amorphous Rebaudioside D" will refer to any highly purified form of Rebaudioside D obtained by spray drying or freeze drying the aqueous solution or aqueous alcoholic solution containing Rebaudioside D.
[025] Hereinafter, the terms "non-steviol glycoside fraction" or "non-glycoside fraction" mean materials comprising predominantly compounds, other than steviol glycosides, which are present in the aqueous extracts of stevia rebaudiana leaves or commercially available stevia extracts more than 0.0001% (w / w), on a dry basis. Non-limiting examples of such compounds include typical plant materials; such as pigments and saccharides, phenolic compounds, volatile oily components, sterols, triterpenes, flavonoids, coumarins, non-glycosidic diterpenes (sterebins), spatulenol, decanoic acid, 8,11,14-ecosatrienoic acid, 2-methyloctadecane, pentacosane, octacosane, stigmasterol, bsitosterol, a- and b-amyrin, lupeol, b-amyrin acetate, and pentacyclic triterpene or combinations thereof. Materials designated as "non-steviol glycoside fraction" or "non-glycoside fraction" and prepared in some embodiments of the present invention, may also contain small residual amounts of steviol glycosides.
[026] Hereinafter, the term "polyol" refers to a compound that contains more than one hydroxyl group. A polyol can contain 2-7 hydroxyl groups. Non-limiting examples of polyols include erythritol, maltitol, mannitol, sorbitol, lactitol, xylitol, inositol, isomalt, propylene glycol, glycerol (glycerin), treitol, galactitol, reduced isomalto-oligosaccharides, reduced xyl-oligosaccharides, reduced oligosaccharides, reduced reduced maltose syrup, reduced glucose syrup, or combinations of those mentioned.
[027] Hereinafter the term “molasses” refers to sugar cane molasses, such as first molasses, second molasses, US grade “A”, “B”, “C”, and final non-standard molasses (substandard blackstrap molasses), as well as beet molasses, molasses molasses, high-yield molasses, refineries molasses, sweet sorghum syrup. Non-limiting examples of typical constituents of molasses are sucrose, glucose, fructose, starch, gums, pentosans, hexitols, myoinositols, maintol, amino acids, wax, sterols, phosphatides, aconitic acid, citric acid, malic acid,
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6/16 oxalic acid, glycolic acid, succinic acid, fumaric acid, melanoidins or mixtures thereof.
[028] Hereinafter the term “caramel” refers to the colors caramel class I (INS No: 150a), Class II (INS No: 150b), class III (INS No: 150c) and class IV (INS No: 150d) or their mixtures.
[029] In one embodiment of the invention, crystalline Reb D was dissolved in a water-ethanol mixture and spray-dried to obtain the amorphous form of Reb D with improved solubility.
[030] In another embodiment, crystalline or amorphous Reb D is combined with a polyol in a ratio of 1: 100 to 100: 1 (w / w) to obtain a composition with improved Reb D solubility.
[031] In yet another embodiment, the combination of amorphous Reb D and polyol in a ratio of 1: 100 to 100: 1 (w / w) is dissolved in water or aqueous alcohol and spray dried to provide a Reb D composition with better solubility.
[032] In another embodiment, the combination of amorphous Reb D and polyol in a ratio of 1: 100 to 100: 1 (w / w) is granulated by means of a roller compaction granulator. The granulated material made according to the present invention advantageously provides a product with favorable characteristics such as solution of Reb D and particle size distribution.
[033] In another embodiment, the Steviol glycosides are separated from the aqueous extract of Stevia rebaudian leaves to obtain the non-glycoside fraction of Stevia. Any separation technique known in the art, such as chromatographic separation, crystallization from water or aqueous alcohol, adsorption on specific resins, membrane separation, or extraction by supercritical fluid, can be employed.
[034] In another embodiment, crystalline or amorphous Reb D is combined with a stevia glycoside fraction in a ratio of 1: 100 to 100: 1 (w / w) to obtain a Reb D composition with improved solubility.
[035] In yet another embodiment the combination of crystalline Reb D and non-glycoside stevia fraction in a ratio of 1: 100 to 100: 1 (w / w) is dissolved in water or aqueous alcohol and spray dried to provide a composition
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7/16 with improved Reb D solubility.
[036] In another embodiment, amorphous or crystalline Reb D is combined with molasses or caramel in a ratio of 1: 100 to 100: 1 // w / w) to obtain a composition with improved Reb D solubility.
[037] In another embodiment, the combination of amorphous or crystalline Reb D and molasses or caramel in a ratio of 1: 100 to 100: 1 (w / w) is dissolved in water or aqueous alcohol and dried to obtain an improved composition Reb D solubility
[038] It is to be understood that both the previous general description and the following detailed description are exemplary and explanatory and are intended to provide a further explanation of the invention as claimed.
Brief Description of Drawings
Figure 1 shows the chemical structure of Rebaudioside D (CAS: 63279-130).
Detailed Description of the Invention [039] The invention aims to provide forms of Rebaudioside D or compositions containing Rebaudioside D with better solubility in water.
[040] In one embodiment, highly purified crystalline Rebaudioside D, which has a solubility of 0.05%, was dissolved in aqueous alcohol at a concentration of 0.5 to 50%, preferably 5-25%, more preferably 10-20% . The alcohol content used in the aqueous alcohol is 0.1-100% (v / v), preferably 20-70% (v / v), more preferably 30-50% (v / v). The alcohol is selected from the group consisting of alkanols, more particularly methanol, ethanol, n-propanol, 2-propanol, 1-butanol, 2-butanol or combinations thereof. To dissolve Reb D, the solution is heated to 30-100 ° C, preferably to 50-100 ° C, more preferably to 60-100 ° C. To avoid premature crystallization, the solution is kept at 20-80 ° C, preferably at 30-70 ° C, more preferably at 50-60 ° C. The solution is fed to a spray dryer, in order to obtain a highly purified amorphous Reb D powder, with a solubility of 0.2%.
[041] In another modality, highly purified amorphous or crystalline Rebaudioside D is combined with a polyol in a ratio of 1: 1 to 1: 100 (weight / weight), preferably 1: 1 to 1:30 (w / w), more preferably 1: 1 to 1:10. The polyol is
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8/16 selected from the group consisting of erythritol, maltitol, mannitol, sorbitol, lactitol, xylitol, inositol, isomalt, propylene glycol, glycerol (glycerin), treitol, galactitol, reduced isomalto-oligosaccharides, reduced xylo-oligosaccharides, reduced oligosaccharides , reduced maltose syrup, reduced glucose syrup or combinations thereof. Preferably, the polyol is selected from the group consisting of erythritol, maltitol, mannitol, sorbitol, lactitol, xylitol, inositol, and isomalt, and more preferably, erythritol, maltitol, sorbitol and isomalt. When prepared compositions containing crystalline Reb D are dissolved in water at room temperature, the solubility of Reb D is 0.1-2.0%. For compositions with amorphous Reb D the solubility under the same conditions is 0.3-2.0%.
[042] In another embodiment, the combination of amorphous Reb D and polyol in a ratio of 1: 1 to 1: 100 (w / w), preferably 1: 1 to 1:30 (w / w), more preferably 1: 1 to 1:10, is granulated by any equipment known in the art suitable for granulating the fine powder as granules, preferably by means of a roller compaction granulator. The speed of the roll was about 5-20 rpm, preferably between about 7-10 rpm, and most preferably about 9 rpm. The pressure of the roller was between about 20-80 bar, preferably between about 40-50 bar, and more preferably about 45 bar. The granulator rotors were rotating at a speed of between about 50-2000 rpm, preferably between about 100-200 rpm, and more preferably at about 150 rpm. The granulators were equipped with screens of sizes that were between about 0.5-6.0 mm, preferably between about 1-4 mm, and more preferably about 3.1 mm for the pre-granulator and about 1, 6 mm for the fine granulator. When the prepared compositions are dissolved in water, the solubility of Reb D is 0.1-2.5%.
[043] In another embodiment, the non-glycosidic fraction of stevia is combined with crystalline Rebaudioside D, in a ratio of 1: 1 to 1: 100 (weight / weight), preferably from 1: 2 to 1:20 (w / p), more preferably from 1: 3 to 1:10. The mixture is dissolved in aqueous alcohol at a concentration of 0.5 to 50%, preferably 525%, more preferably 10-20%. The alcohol content in the aqueous alcohol used is 0.1-100% (v / v), preferably 20-70% (v / v), more preferably 30-50% (v / v). The alcohol is selected from the group consisting of alkanols, more particularly methanol, ethanol, n-propanol, 2-propanol, 1-butanol and 2-butanol. For
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9/16 dissolve Reb D, the solution is heated to 30-100 ° C, preferably to 50-100 ° C, more preferably to 60-100 ° C. To avoid premature crystallization, the solution is kept at 20-80 ° C, preferably at 30-70 ° C, more preferably at 50-60 ° C. The solution is fed to a spray dryer to obtain a highly soluble Reb D composition powder. When the prepared compositions are dissolved in water at room temperature the solubility of Reb D is 0.3-5.0%, or 0.1-2.5%.
[044] In another embodiment, molasses are combined with crystalline Rebaudioside D, in a ratio of 1: 1 to 1: 100 (w / w), preferably from 1: 2 to 1:20 (w / w), more preferably 1 : 3-1: 10. The mixture is dissolved in aqueous alcohol at a concentration of 0.5 to 50%, preferably 5-25%, more preferably 10-20%. The alcohol content in the aqueous alcohol used is 0.1-100% (v / v), preferably 20-70% (v / v), more preferably 30-50% (v / v). The alcohol is selected from the group consisting of alkanols, more particularly methanol, ethanol, n-propanol, 2propanol, 1-butanol, 2-butanol. Molasses are selected from the group consisting of US grade “A”, “B” and “C” molasses, as well as non-standard molasses, preferably grade “A” molasses. To dissolve Reb D the solution is heated to 30-100 ° C, preferably to 50-100 ° C, more preferably to 60-100 ° C. To avoid premature crystallization, the solution is kept at 20-80 ° C, preferably at 30-70 ° C, more preferably at 50-60 ° C. The solution is fed to a spray dryer to obtain a highly soluble Reb D composition powder. When the prepared compositions are dissolved in water, the solubility of Reb D is 0.1-3.5%.
[045] In another embodiment, caramel is combined with crystalline Rebaudioside D, in a ratio of 1: 1 to 1: 100 (w / w), preferably from 1: 2 to 1:20 (w / w), more preferably from 1 : 3-1: 10. The mixture is dissolved in aqueous alcohol at a concentration of 0.5 to 50%, preferably 5-25%, more preferably 1020%. The alcohol content in the aqueous alcohol used is 0.1-100% (v / v), preferably 20-70% (v / v), more preferably 30-50% (v / v). The alcohol is selected from the group consisting of alkanols, more particularly methanol, ethanol, n-propanol, 2-propanol, 1-butanol, 2-butanol. The caramel is selected from the group comprising caramel colors of class I, class II, class III and class IV caramel colors, preferably caramel class I. To dissolve the Reb D the solution is heated to 30-100 ° C, preferably 50-100 ° C, more preferably 60
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100 ° C. To avoid premature crystallization of the solution it is kept at 20-80 ° C, preferably at 30-70 ° C, more preferably at 50-60 ° C. The solution is fed to a spray dryer to obtain a highly soluble Reb D composition powder. When the prepared compositions are dissolved in water, the solubility of Reb D is 0.3-3.5%.
[046] The following examples illustrate preferred embodiments of the invention. It will be understood that the invention is not limited to the materials, proportions, conditions and procedures set out in the examples, which are illustrative only.
Example 1: Preparation of amorphous Rebaudioside D
100 g of crystalline Rebaudioside D, produced by PureCircle Sdn Bhd, with 98.1% purity (on anhydrous basis) was dissolved in 500 ml of aqueous ethanol, containing 50% (vol) of ethanol The solution was maintained at 50 ° C and dried using a laboratory spray dryer YC-015 (Shanghai Pilotech Instrument & Equipment Co. Ltd., China), operating at inlet temperatures of 175 ° C and outlet of 100 ° C. The amorphous powder obtained was compared with the crystalline material for solubility.
Table 2
Rebaudioside D solubility
Temperature Solubility in water) Crystalline Amorphous 20 ° C 0.05 0.1 50 ° C * 0.2 0.5 100 ° C * 0.5 1.1
* Solutions obtained at 50 ° C and 100 ° C crystallized after cooling to room temperature (20 ° C).
Example 2: Preparation of Non-Glycosidic Fraction
500 g of commercial stevia extract, containing Rebaudioside A 41.2%, Stevioside 30.6%, Rebaudioside C 9.9%, Rebaudioside F 2.3%, Dulcoside A 0.5%, Rubusoside 0.6%, Rebaudioside D 1.5%, Etheviolbioside 0.2% and Rebaudioside B 0.1%, were dissolved in 9.5 liters of reverse osmosis (OR) water and passed through a column loaded with 10 liters of Amberlite XAD7HP resin. The column was washed with 10 volumes of OR water. The collected water fractions were evaporated in vacuo at 55 ° C and spray dried to obtain 45g of powder with 9.8% GET including Rebaudioside D 7.8%, Rebaudioside A 2.0% and undetectable amounts of other glycosides steviol.
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Example 3: Preparation of soluble composition of Rebaudioside D g of crystalline Rebaudioside D, produced by PureCircle Sdn Bhd, with 98.1% purity (relative to the anhydrous product) were mixed with different amounts of erythritol (Prima Inter-Chem Sdn Bhd , Malaysia). The obtained mixtures were tested for stability, and the stability of the solution for crystallization, during storage, at room temperature.
Table 3
Mixing solubility of Rebaudioside D
Mixing ratio, p / p Reb D / Erythritol Solubility *, (Reb D in water) 20 ° C 100 ° C ** 2: 1 0.06 0.09 1: 1 0.08 0.2 1: 5 0.20 0.5 1:10 0.40 1.0 1:15 0.80 1.3 1:20 1.50 2.0 * Solubility is ca calculated for the content of Reb D% in solution
** The material was dissolved at 100 ° C and cooled to room temperature (20 ° C). The reported concentrations are stable (do not crystallize) for 24 hours at room temperature.
Example 4: Preparation of the composition of soluble Rebaudioside D g of amorphous Rebaudioside D prepared according to Example 1 were mixed with different amounts of erythritol (Prima Inter-Chem Sdn Bhd, Malaysia). The obtained mixtures were tested for stability, and solution stability for crystallization, during storage at room temperature.
Table 4
Mixing solubility of Rebaudioside D
Mixing ratio, p / p Reb D / Erythritol Solubility *, (Reb D in water) 20 ° C 100 ° C ** 2: 1 0.08 0.09 1: 1 0.16 0.2 1: 5 0.40 0.5 1:10 0.90 1.0 1:15 1.00 1.3 1:20 1.10 2.0 * Solubility is ca calculated for the content of Reb D% in solution
** The material was dissolved at 100 ° C and cooled to room temperature
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12/16 (20 ° C). The reported concentrations are stable (do not crystallize) for 24 hours at room temperature.
Example 5: Preparation of composition of soluble Rebaudioside D g of crystalline Rebaudioside D, produced by PureCircle Sdn Bhd, with 98.1% purity (in relation to the anhydrous product) were mixed with different amounts of erythritol (Prima Inter-Chem Sdn Bhd , Malaysia). The obtained mixtures were dissolved in 5 volumes of aqueous ethanol containing 50% (vol) ethanol. The solution was maintained at 50 ° C and dried using a YC-015 laboratory spray dryer (Shanghai Pilotech Instrument & Equipment Co. Ltd., China), operating at inlet temperatures at 175 ° C and outlet at 100 ° C . The amorphous powder obtained was tested for solubility and stability of the solution for crystallization during storage at room temperature.
Table 5
Mixing solubility of Rebaudioside D
Mixing ratio, p / p Reb D / Erythritol Solubility *, (Reb D in water) 20 ° C 100 ° C ** 2: 1 0.16 0.2 1: 1 0.30 0.4 1: 5 0.60 0.7 1:10 1.20 1.4 1:15 1.50 1.8 1:20 1.80 2.5 * Solubility is ca calculated for the content of Reb D% in solution
** The material was dissolved at 100 ° C and cooled to room temperature (20 ° C). The reported concentrations are stable (do not crystallize) for 24 hours at room temperature.
Example 6: Preparation of Composition of Soluble Rebaudioside D g of crystalline Rebaudioside D, produced by PureCircle Sdn Bhd, with 98.1% purity (in relation to the anhydrous product) were mixed with different amounts of non-glycosidic fraction of stevia prepared according to with Example 2. The mixtures obtained were tested for stability and solubility of the solution with respect to crystallization, during storage at room temperature.
Table 6
Solubility of Rebaudioside D mixtures
Mixing ratio, p / p Solubility *, (Reb D in water)
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Reb D / non-glycosidic fraction 20 ° C 100 ° C ** 1: 2 0.07 2.1 1: 1 0.06 1.5 2: 1 0.06 1.3 3: 1 0.06 0.8 4: 1 0.06 0.3 5: 1 0.05 0.15 * Solubility is ca calculated for the content of Reb D% in solution
** The material was dissolved at 100 ° C and cooled to room temperature (20 ° C). The reported concentrations are stable (do not crystallize) for 24 hours at room temperature.
EXAMPLE 7: Preparation of Composition of Soluble Rebaudioside D Amorphous Rebaudioside D, prepared according to Example 1, were mixed with different amounts of non-glycosidic stevia fraction, prepared according to Example 2. The obtained mixtures were tested for solubility, and stability of the solution with respect to crystallization, during storage at room temperature.
Table 7
Solubility of Rebaudioside D mixtures
Mixing ratio, p / p Reb D / non-glycosidic fraction Solubility *, (Reb D in water) 20 ° C 100 ° C ** 1: 2 0.10 2.1 1: 1 0.09 1.5 2: 1 0.08 1.3 3: 1 0.06 0.8 4: 1 0.06 0.3 5: 1 0.05 0.15 * Solubility is ca calculated for the content of Reb D% in solution
** The material was dissolved at 100 ° C and cooled to room temperature (20 ° C). The reported concentrations are stable (do not crystallize) for 24 hours at room temperature.
Example 8: Preparation of composition of soluble Rebaudioside D g of crystalline Rebaudioside D were mixed with different amounts of non-glycosidic stevia fraction, prepared according to Example 2. The obtained mixtures were dissolved in 5 volumes of 50% aqueous ethanol ( v) ethanol. The solution was maintained at 50 ° C and dried using a
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14/16 laboratory spray YC-015 (Shanghai Pilotech Instrument & Equipment Co. Ltd., China), operating at inlet temperatures at 175 ° C and outlet at 100 ° C. The amorphous powder obtained was tested for solubility and stability of the solution for crystallization during storage at room temperature.
Table 8
Solubility of Rebaudioside D mixtures
Mixing ratio, p / p Reb D / non-glycosidic fraction Solubility *, (Reb D in water) 20 ° C 100 ° C ** 1: 2 0.40 2.5 1: 1 0.30 2.1 2: 1 0.20 1.8 3: 1 0.10 1.4 4: 1 0.08 0.9 5: 1 0.06 0.4 * Solubility is ca calculated for the content of Reb D% in solution
** The material was dissolved at 100 ° C and cooled to room temperature (20 ° C). the reported concentrations are stable (do not crystallize) for 24 hours at room temperature.
Example 9: Preparation of Composition of Soluble Rebaudioside D Crystalline Rebaudioside D, produced by PureCircle Sdn Bhd, were mixed with different amounts of molasses (Chee Lam Trading, Malaysia). The obtained mixtures were dissolved in 5 volumes of aqueous ethanol containing 50% (vol) ethanol. The solution was maintained at 50 ° C and dried using a YC-015 laboratory spray dryer (Shanghai Pilotech Instrument & Equipment Co. Ltd., China), operating at inlet temperatures at 175 ° C and outlet at 100 ° C . The amorphous powder obtained was tested for solubility and stability of the solution for crystallization during storage at room temperature.
Table 9
Solubility of Rebaudioside D mixtures
Mixing ratio, p / p Reb D / non-glycosidic fraction Solubility *, (Reb D in water) 20 ° C 100 ° C ** 1: 2 0.50 3.5 1: 1 0.30 2.6 2: 1 0.20 2.1 3: 1 0.10 1.6
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4: 1 0.09 1.2 5: 1 0.08 0.5 * Solubility is ca responsible for the content of Reb D% in solution
** The material was dissolved at 100 ° C and cooled to room temperature (20 ° C). The reported concentrations are stable (do not crystallize) for 24 hours at room temperature.
Example 10: Preparation of granulated composition of soluble Rebaudioside D kg of amorphous Rebaudioside D prepared according to example 1, was mixed with different amounts of erythritol (Prima Inter-chem Sdn Bhd, Malaysia). The obtained mixtures were transferred to an Alexanderwerk WP 50N / 75 roller compactor. The compactor was operated at 9 rpm and a pressure of 45 bar. The compacted mass was fed to a pre-granulator and to a fine granulator with rotors at a rotation speed of 150 rpm. The screen size for the pre-granulator was 3.1 mm and for the fine granulator it was 1.6 mm. The “above” (particles that were very large, and the “fine” (particles that were very small) were separated by the upper screen having a screen size of US Mesh 10 and a background screen of US Mesh 40. The percentage ratio of “Above”: “product”: “fine” was 0.9%: 78.2%: 20.9%, respectively.The products obtained were tested for solubility and stability of the solution with respect to crystallization during storage in the room temperature.
Table 10
Solubility of Rebaudioside D mixtures
Mixing ratio, p / p Reb D / Erythritol Solubility *, (Reb D in water) 20 ° C 100 ° C ** 2: 1 0.09 0.1 1: 1 0.17 0.2 1: 5 0.40 0.6 1:10 0.90 1.2 1:15 1.00 1.8 1:20 1.50 2.5 * Solubility is ca calculated for the content of Reb D% in solution
** The material was dissolved at 100 ° C and cooled to room temperature (20 ° C). The reported concentrations are stable (do not crystallize) for 24 hours at room temperature.
Petition 870180136090, of September 28, 2018, p. 24/29
16/16 [047] Although one or more modalities of the present invention have been described, it will be understood by those usually skilled in the art that various changes and modifications can be made and equivalents can be substituted as to their elements or compositions, without departing from the true scope of the invention. Therefore, it is intended that the present invention is not limited to a particular embodiment disclosed herein, but that the invention includes all embodiments that fall within the scope of the appended claims.

权利要求:
Claims (8)
[1]
1. Method for preparing a highly soluble Rebaudioside D composition CHARACTERIZED by the fact that it comprises the steps of:
a) providing a first composition comprising Rebaudioside D;
b) providing a second composition comprising at least one component selected from the group consisting of: a non-glycosidic stevia fraction, in a ratio (w / w) of the non-glycosidic stevia fraction to the first 1: 100 composition to 100: 1, preferably from 1: 2 to 1:20, more preferably from 1: 3 to 1:10; molasses, in a molasses (w / w) ratio for the first composition from 1: 100 to 100: 1, preferably from 1: 2 to 1:20 and, more preferably from 1: 3 to 1:10; and caramel color, where the caramel is in a caramel (w / w) ratio for the first composition from 1: 100 to 100: 1, preferably from 1: 2 to 1:20, and more preferably from 1: 3 to 1:10;
c) dissolving the first and second compositions in a solvent selected from the group consisting of water or aqueous alcohol to form a solution; and
d) spray drying the solution in a spray dryer operating at an inlet temperature of 150-200 ° C and an outlet temperature of 80-120 ° C to obtain the highly soluble Rebaudioside D composition.
[2]
2. Method, according to claim 1, CHARACTERIZED by the fact that the non-glycosidic fraction of stevia is prepared by a process comprising the steps of:
supply of a stevia extract;
dissolving the stevia extract in water or aqueous alcohol to form a stevia extract solution;
pass the stevia extract solution through a chromatographic system filled with macroporous adsorbent resin capable of adsorbing steviol glycosides;
collect an effluent from the chromatographic system; and drying the effluent to obtain the non-glycosidic fraction of stevia.
[3]
3. Method according to claim 2, CHARACTERIZED by the fact that the stevia extract contains 10-95%, preferably 30-90%, and more preferably 40-85% total steviol glycosides.
Petition 870180136090, of September 28, 2018, p. 26/29
2/2
[4]
4. Method according to claim 2, CHARACTERIZED by the fact that the ratio of water or aqueous alcohol to the dissolved solids of the stevia extract (volume / weight) is from 1: 1 to 200: 1, preferably 5: 1 to 100: 1, more preferably 10: 1 to 50: 1.
[5]
5. Method according to claim 2, CHARACTERIZED by the fact that the amount of stevia extract exceeds the adsorbent capacity of the adsorbent in the chromatography system by 1-10 times, preferably 1 -5 times, and more preferably 1 -1.5 times.
[6]
6. Method according to claim 2, CHARACTERIZED by the fact that the chromatography system comprises 1-20 columns consecutively connected, preferably 1-10 columns, and more preferably 1-6 columns.
[7]
7. Method, according to claim 1, CHARACTERIZED by the fact that molasses is selected from the group consisting of: sugar cane molasses such as first molasses, second molasses, US grade “A”, “B” , “C”, and non-standard final molasses; beet molasses, re-molasses molasses, high-yield molasses, refinery molasses, sweet sorghum syrup, and mixtures of those mentioned.
[8]
8. Method, according to claim 1, CHARACTERIZED by the fact that the caramel is selected from the group consisting of caramel colors Class I (INS No: 150a), Class II (INS No: 150b), Class III (INS No: 150c) and class IV (INS No: 150d) or mixtures thereof.

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法律状态:
2017-12-12| B06F| Objections, documents and/or translations needed after an examination request according art. 34 industrial property law|

2018-03-27| B15K| Others concerning applications: alteration of classification|Ipc: A23L 27/30 (2016.01), A23L 2/60 (2006.01), A24B 13 |

2018-05-15| B15K| Others concerning applications: alteration of classification|Ipc: C07H 15/24 (2006.01), C07H 1/08 (2006.01), A23L 27 |

2018-07-03| B06A| Notification to applicant to reply to the report for non-patentability or inadequacy of the application according art. 36 industrial patent law|

2019-01-22| B09A| Decision: intention to grant|

2019-04-02| B16A| Patent or certificate of addition of invention granted|Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 12/12/2011, OBSERVADAS AS CONDICOES LEGAIS. (CO) 20 (VINTE) ANOS CONTADOS A PARTIR DE 12/12/2011, OBSERVADAS AS CONDICOES LEGAIS |

优先权:

申请号 | 申请日 | 专利标题

US42240310P| true| 2010-12-13|2010-12-13|

US61/422,403|2010-12-13|

US201061424798P| true| 2010-12-20|2010-12-20|

US61/424,798|2010-12-20|

PCT/US2011/064343|WO2012082587A2|2010-12-13|2011-12-12|Highly soluble rebaudioside d|

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