• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
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    • 专利摘要:
    stevia composition. stevia compositions are prepared from steviol glycosides from stevia rehaudiana bertoni. the compositions are capable of providing a superior flavor profile and can be used as sweetness enhancers, flavor enhancers and as sweeteners in foods, beverages, cosmetics and pharmaceuticals.
    公开号:BR112013030701B1
    申请号:R112013030701-3
    申请日:2011-08-11
    公开日:2021-07-20
    发明作者:Avetik Markosyan
    申请人:Purecircle Usa Inc；
    IPC主号:
    专利说明:

    Field of Invention
    [001] The invention relates to a process for producing a highly purified food ingredient from the plant extract Stevia rebaudiana Bertoni and its use in various food and beverage products. Description of Related Art
    [002] Sugar alternatives are receiving increasing attention due to awareness of the many illnesses associated with the consumption of high sugar foods and beverages. However, many artificial sweeteners, such as dulcine, sodium cyclamate and saccharin, have been banned or restricted in some countries due to concerns about their safety. As a result, non-caloric sweeteners of natural origin are becoming increasingly popular. Stevia rebaudiana Bertoni fennel produces several diterpene glycosides that feature high-intensity sweetness and sensory properties superior to those of many other high-potency sweeteners.
    [003] The aforementioned sweet glycosides have a common aglycone, steviol, and differ by the number and type of carbohydrate residues at positions C13 and C19. Stevia leaves can accumulate up to 10-20% (based on dry weight) of steviol glycosides. The main glycosides found in Stevia leaves are rebaudioside A (2-10%), stevioside (2-10%), and rebaudioside C (1-2%). Other glycosides such as rebaudioside B, D, E and F, steviolbioside and rubusoside are found at much lower levels (approximately 0-0.2%).
    [004]Two major glycosides - stevioside and rebaudioside A (reb A) - have been studied extensively and characterized in terms of their suitability as high intensity commercial sweeteners. Stability studies with carbonated beverages have confirmed their stability to heat and pH (Chang S.S., Cook, J.M. (1983) Stability studies of stevioside and rebaudioside A in carbonated beverges. J. Agric. Food Chem. 31: 409-412).
    [005] Steviol glycosides differ from others not only by molecular structures, but also by their flavor properties. Typically, stevioside is considered to be 110-270 times sweeter than sucrose, rebaudioside A between 150 and 320 times sweeter than sucrose, and rebaudioside C between 40-60 times sweeter than sucrose. Dulcoside A is 30 times sweeter than sucrose. Rebaudioside A has the least astringent, less bitter, and less persistent aftertaste, thus, it has the most favorable sensory attributes of the major steviol glycosides (Tanaka O. (1987) Improvement of taste of natural sweetners. Pure Appl. Chem. 69: 675-683; Phillips KC (1989) Stevia: steps in developing a new sweetener. In: Grenby TH ed. Developments in sweeteners, vol. 3. Elsevier Applied Science, London. 1-43). The chemical structure of rebaudioside A is shown in Fig. 1.
    [006] Methods for extracting and purifying sweet glycosides from the Stevia rebaudiana plant using water or organic solvents are described in, for example, U.S. Patent No. 4,361,697; 4,082,858; 4,892,938; 5,972,120; 5,962,678; 7,838,044 and 7,862,845.
    [007] However, even in a highly purified state, steviol glycosides still have undesirable flavor attributes such as bitterness, sweet aftertaste, licorice flavor, etc. One of the main obstacles to the successful marketing of stevia sweeteners is these undesirable flavor attributes. These flavor tones have been shown to become more prominent when the concentration of steviol glycosides increases (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).
    [008] Rebaudioside B (CAS No: 58543-17-2), or reb B, likewise known as stevioside A4 (Kennelly EJ (2002) Constituents of Stevia rebaudiana In Stevia: The genus Stevia, Kinghorn AD (Ed ), Taylor & Francis, London, p.71), is one of the sweet glycosides found in Stevia rebaudiana. Sensory evaluations show that reb B is approximately 300-350 times sweeter than sucrose, whereas for reb A this value was approximately 350-450 times (Crammer, B. and Ikan, R. (1986) Sweet glycosides from the Stevia plant Chemistry in Britain 22, 915-916, and 918). The chemical structure of rebaudioside B is shown in Fig. 2.
    [009] It is believed that reb B is formed from the partial hydrolysis of rebaudioside A during the extraction process (Kobayashi, M., Horikawa, S., Degrandi, IH, Ueno, J. and Mitsuhashi, H. ( 1977) Dulcosides A and B, new diterpene glycosides from Stevia rebaudiana. Phytochemistry 16, 1405 - 1408). However, other research has shown that reb B occurs naturally in Stevia rebaudiana leaves and is currently one of nine steviol glycosides recognized by FAO/JECFA (United Nations Food and Agriculture Organization/Joint Expert Committee on Food Additives) in calculating total content of steviol glycosides in commercial steviol glycoside preparations (FAO JECFA (2010) Steviol Glycosides, Compendium of Food Additive Specifications, FAO JECFA Monographs 10, 17-21).
    [0010] Only a few methods are described in the literature to prepare reb B.
    [0011] Kohda et al., (1976) prepared reb B by hydrolysis of reb A with hesperidinase. Reb B was similarly prepared by alkaline saponification of reb A. Said saponification was conducted in 10% potassium hydroxide-ethanol. The solution was acidified with acetic acid and extracted with n-butanol. The butanol layer was washed with water and concentrated at low temperature in vacuo. The residue was crystallized from methanol to produce reb B. (Kohda, H., Kasai, R., Yamasaki, K., Murakami, K. and Tanaka, O. (1976) New sweet diterpene glucosides from Stevia rebau - Diana. Phytochemistry 15, 981-983). The processes described may be suitable for laboratory-scale preparation of reb B, however, they are not suitable for any large-scale or commercial-scale preparation of reb B.
    [0012] Ahmed et al. used mild alkaline hydrolysis of reb A to prepare reb B. According to the procedure described, reb A was hydrolyzed to reb B by refluxing with 10% aqueous KOH at 100°C for 1 hour. After neutralization with glacial acetic acid, the precipitated substance was recrystallized twice from methanol (Ahmed MS, Dobberstein RH, and Farnsworth NR (1980) Stevia rebaudiana: I. Use of p-bromophenacyl bromide to enhance ultraviolet detection of water- soluble organic acids (steviolbioside and rebaudioside B) in high-performance liquid chromatographic analysis, J. Chromatogr., 192, 387-393).
    [0013] The use of methanol as the recrystallization medium as described in the literature will require its subsequent removal from the product. It is noted that the handling of toxic substances, such as methanol, requires specialized industrial facilities and, when applied to the food process, sophisticated food safety measures.
    [0014] It is likewise noted that no significant work has been conducted to determine the potential of reb B as a sweetener or food ingredient. Furthermore, reb B is often seen as a process artifact and unnecessary impurity in commercial steviol glycoside preparations. No significant assessment of the influence of reb B on the total flavor profile of steviol glycoside preparations was conducted.
    [0015] The water solubility of reb B is reported to be about 0.1% (Kinghorn DC (2002) Constituents of Stevia rebaudiana In Stevia: The genus Stevia, Kinghorn AD (Ed), Taylor & Francis, London, p.8). In many food processes where highly concentrated ingredients are used, a highly soluble form of reb B will be required.
    [0016] Considering the facts mentioned above, there is a need to evaluate reb B as a sweetener and food ingredient and to develop a simple and efficient process for food grade reb B preparations suitable for food and other applications.
    [0017] It is also noted that, having a carboxyl group in the molecule, it becomes possible for reb B to exist in the forms of various carboxylate salts. Prior to this invention, it was not believed that a carboxylate salt form other than reb B had been prepared or evaluated for its impact on flavor profiles.
    [0018] Within the description of this invention we will show that, when specifically applied, carboxylate salts of reb B can impact the flavor profile and offer significant advantages for the use of stevia sweeteners in various applications. SUMMARY OF THE INVENTION
    [0019] The present invention aims to overcome the disadvantages of existing Stevia sweeteners. The invention describes a process for producing a high purity food ingredient from the extract of the plant Stevia rebaudiana Bertoni and using it in various food and beverage products as a sweetness and flavor modifier.
    [0020] The invention, in part, belongs to an ingredient comprising steviol glycosides from the plant Stevia rebaudiana Bertoni. Steviol glycosides are selected from the group consisting of stevioside, rebaudioside A (FIG. 1), rebaudioside B (FIG. 2), rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, dulcoside A, steviolbioside, rubusoside, as well as other steviol glycosides found in the plant Stevia rebaudiana Bertoni and mixtures thereof.
    [0021] The invention, in part, belongs to a process for producing an ingredient that contains rebaudioside B, and stevioside, rebaudioside A, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, dulcoside A, steviol-bioside, rubusoside, well as other steviol glycosides found in the plant Stevia rebaudiana Bertoni and mixtures thereof.
    [0022] In the invention, rebaudioside A marketed by PureCircle Sdn. Bhd (Malaysia) containing rebaudioside A (about 95-100%), stevioside (about 01%), rebaudioside C (about 0-1%), rebaudioside F (about 0-1%), rebaudioside B (about 0-1%) 0.1-0.8%), rebaudioside D (about 0-1%) and other glycosides that reach total steviol glycoside content of at least 95%, can be used as a starting material. Alternatively, stevia extracts with different ratios of steviol glycosides can be used as starting materials.
    [0023] In one embodiment, the starting material is subjected to partial or total conversion to reb B using an alkaline conversion process. The obtained reb B is then transformed into a carboxylate salt form which interacts with its base. These salt forms are used similarly as the "original" reb B with a carboxyl group.
    [0024] The obtained reb B or its carboxylate salt forms and mixtures thereof can be subjected to additional heat treatment to increase the solubility.
    [0025] The obtained products have been applied in various foods and beverages as sweeteners, sweetener enhancers and flavor modifiers, including soft drinks, ice cream, cookies, bread, fruit juices, dairy products, baked goods and confectionery products.
    [0026] It is to be understood that both the preceding general description and the following detailed description are exemplary and explanatory and are intended to provide another explanation of the invention as claimed. BRIEF DESCRIPTION OF THE DRAWINGS
    [0027] The accompanying drawings are included to provide further understanding of the invention. The drawings illustrate embodiments of the invention and, together with the description, serve to explain the principles of embodiments of the invention. FIG. 1 shows the chemical structure of rebaudioside A. FIG. 2 shows the chemical structure of rebaudioside B. FIG. 3 shows an HPLC chromatography of a stevia composition comprising rebaudioside A and rebaudioside B. DETAILED DESCRIPTION OF THE INVENTION
    [0028] Advantages of the present invention will become more evident from the detailed description produced below. However, it is to be understood that the detailed description and specific examples, while indicating preferred embodiments of the invention, are given by way of illustration only, as various changes and modifications within the spirit and scope of the invention will be evident to those skilled in the art a from this detailed description.
    [0029] Rebaudioside A marketed by PureCircle Sdn. Bhd (Malaysia) containing rebaudioside A (about 95-100%), stevioside (about 0-1%), rebaudioside C (about 0-1 %), rebaudioside D (about 0-1 %), rebaudioside F ( about 0-1%), rebaudioside B (about 0.1-0.8%) and other glycosides that reach the total steviol glycoside content of 95%, can be used as a starting material. Alternatively, stevia extracts with different ratios of steviol glycosides can be used as starting materials.
    [0030] The HPLC analysis of raw materials and products can be performed on an Agilent Technologies 1200 Series (USA) liquid chromatograph, equipped with Phenomenex Prodigy ODS3, 5 μm column (4.6X250mm) at 40°C. The mobile phase was composed of 32:68 acetonitrile and 10 mmol/L sodium phosphate buffer (about pH 2.6) at 1 mL/min. A 210 nm diode array detector can be used as the detector. An example of HPLC chromatography thus obtained is shown in FIG. 3.
    [0031] As used herein, unless otherwise specified, "reb B" and "composition of reb B" will be used interchangeably to refer to purified rebaudioside B or rebaudioside B in combination with any other chemical entity. Preparation of Reb B1. Alkaline Conversion
    [0032] One way to obtain reb B starting from reb A is described as follows. Reb A is dispersed in an aqueous alkaline solution. The concentration of reb A is about 0-50% (w/v) preferably about 10-25%. Preferred alkaline agents include potassium hydroxide and sodium hydroxide, however, other agents capable of raising the pH of the above media to about pH 7 can be used equally or alternatively. The concentration of alkaline agents is about 0.05-2.0M, preferably about 0.1-1.0M. The mixture is incubated at about 10-150°C, preferably about 30-100°C, for a period of about 0.5-48 hours, preferably about 1-24 hours. As a result, reb A is hydrolyzed to reb B. The molar yield of the conversion of reb B is about 5-100%, preferably about 10-90%.
    [0033] After the reaction, the alkaline agent is neutralized by an acid, preferably by sulfuric acid or ortho-phosphoric acid, until a pH of about 3.0-5.0 is reached, preferably to a pH of about 3 .0-4.0 be achieved. On neutralization, a precipitate is formed. The precipitate is separated by any method known in the art, such as filtration or centrifugation, and washed with water until the water reaches a pH of about 4.0-5.0. The crystalline material obtained is dried under vacuum at about 60-105°C to produce a mixture of reb A and reb B which has a ratio of about 5%:95% to about 95%:5% (w/w ), preferably from about 50%:50% to about 90%:10% (w/w). 2. Optional Post-Conversion Purification
    [0034] To obtain purified reb B, in one embodiment, the separated precipitate described above is suspended in water and the mixture is subjected to continuous stirring for about 0.5-24 hours, preferably about 1-3 hours, at about 50-100°C, preferably about 60-80°C. The ratio of precipitate to water (w/v) is from about 1:5 to about 1:20, preferably about 1:10 to about 1:15. The washed crystals are separated and dried under vacuum at about 60-105°C to produce reb B with about 99% purity. Optional Post-Conversion Solubility Enhancement
    [0035] The following procedure can be used to increase the water solubility of reb B or any composition of reb B. The compositions obtained generally have a water solubility of less than about 0.2% (w/v). To increase the solubility of these compositions, the composition of reb B is combined with water in a ratio of about 1:1 (w/w) and the mixture obtained is subjected to a thermal gradient treatment that results in a high stability solution. and high concentration. A gradient of about 1°C per minute is used to heat the mixture. The mixture is heated to a temperature of about 110-140°C, preferably about 118-125°C, and is held at maximum temperature for about 0-120 min, preferably about 50-70 min. After heat treatment, the solution is cooled to room temperature in a gradient of about 1°C per minute. The solution is spray dried by a laboratory spray drier operating at inlet temperatures of about 175°C and outlet temperatures of about 100°C. An amorphous form of the composition is obtained with greater than 20% solubility in water at room temperature. Reb B Salt Preparation
    [0036]Reb B obtained using the processes described above, or any other process, can be completely or partially converted into a carboxylate salt form. Reb B, or a composition containing reb B, preferably reb B with a purity greater than 90% (w/w), is dispersed in water to prepare an aqueous dispersion with 5-50% (w/v), preferably 5-15 % of solids content. Excess base is added to achieve a pH level of 6.5-14.0, preferably 8.511.0. The mixture obtained is incubated for 0.1-24 hours, preferably 1-3 hours. Then, the suspended solids are separated by filtration and washed with water until neutral pH of the wash water is obtained. Alternatively, other reactions capable of converting reb B into a carboxylate salt form can be used. Preferred cations are K+ and Na+, and the respective bases - KOH and NaOH - are used. However, other carboxylate salts of reb B can be prepared in a similar manner using the base corresponding to the desired carboxylate salt.
    The obtained carboxylate salt of reb B can also be purified and its solubility enhanced as described above.
    [0038] While not intended to be bound by theory, it is believed that any steviol glycoside having a carboxyl group can be converted to its carboxylate salt form to improve the flavor and/or sweetness profile of the molecule. Another example of a steviol glycoside containing a carboxyl group is steviol-bioside. Use of Reb B Carboxylate Salt
    [0039] The carboxylate salt of reb B described above can be used as a sweetness enhancer, a flavor enhancer and/or sweetener in various beverage and food products. Non-limiting examples of beverage and food products include carbonated soft drinks, ready-to-drink beverages, energy drinks, sports drinks, low-calorie beverages, zero-calorie beverages, sports drinks, teas, fruit and vegetable juices, juice drinks , dairy beverages, yogurt drinks, alcoholic beverages, powdered beverages, bakery products, cookies, cookies, baking mixes, cereals, confections, sweets, milk candies, chewing gum, dairy products, flavored milk, yogurts, flavored yogurts, fermented milk, soy sauce and other soy products, salad dressings, mayonnaise, vinegar, frozen desserts, meat products, fish meat products, bottled and canned foods, tabletop sweeteners, fruits and vegetables .
    [0040] Additionally, the carboxylate salt compositions of reb B can be used in pharmaceutical or pharmaceutical and cosmetic preparations, including, but not limited to: toothpastes, mouthwashes, cough syrup, chewable tablets, lozenges, preparations of vitamin and the like.
    [0041] The compositions can be used "as is" or in combination with other sweeteners, flavors and food ingredients.
    [0042] Non-limiting examples of sweeteners include glycosides of steviol, stevioside, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, dulcoside A, steviolbioside, rubusoside, as well as other stevia glycosides rebaudiana Bertoni and mixtures thereof, stevia extract, Luo Han Guo extract, mogrosides, high fructose corn syrup, corn syrup, invert sugar, fructooligosaccharides, inulin, inulooligosaccharides, coupling sugar, malt -oligosaccharides, maltodextins, corn syrup solids, glucose, maltose, sucrose, lactose, aspartame, saccharin, sucralose, sugar alcohols.
    [0043] Non-limiting examples of flavors include lemon, orange, fruit, banana, grape, pear, pineapple, bitter almond, cola, cinnamon, sugar, cotton candy, vanilla flavors.
    [0044] Non-limiting examples of other food ingredients include flavors, acidulants, organic acids and amino acids, coloring agents, bulking agents, modified starches, gums, texturizers, preservatives, antioxidants, emulsifiers, stabilizers, thickeners, gelling agents.
    [0045] The following examples illustrate various embodiments of the invention. It will be understood that the invention is not limited to the materials, proportions, conditions and procedures mentioned in the examples, which are illustrative only. EXAMPLE 1 Preparation of stevia composition
    [0046]100 g of rebaudioside A produced by PureCircle Sdn. Bhd (Malaysia) containing 98.1% rebaudioside A, 0.3% stevioside, 0.2% rebaudioside C, 0.2% rebaudioside F, 0.4% rebaudioside B and 0.6% rebaudioside D were dispersed in 1000 ml of aqueous KOH (1M) and incubated at 50°C for 2 hours. The temperature of the mixture was lowered to 20°C and the pH was adjusted to pH 4.0 with sulfuric acid. The solution was kept under conditions of moderate agitation for 4 hours and a precipitate formed. The precipitate was filtered off and washed on the filter with 2000 ml of water. The washed crystals were dried under vacuum to yield 86g of material containing about 84% reb A and 16% reb B. The water solubility (at 25°C) of the material obtained was about 0.2% (w/w). /v). EXAMPLE 2 Preparation of stevia composition
    [0047]100 g of rebaudioside A produced by PureCircle Sdn. Bhd (Malaysia) containing 98.1% rebaudioside A, 0.3% stevioside, 0.2% rebaudioside C, 0.2% rebaudioside F, 0.4% rebaudioside B and 0.6% rebaudioside D were dispersed in 1000 ml aqueous KOH (1M) and incubated at 80°C for 5 hours. The temperature of the mixture was lowered to 20°C and the pH was adjusted to about pH 4.0 with sulfuric acid. The solution was kept under conditions of moderate agitation for 4 hours and a precipitate formed. The precipitate was filtered off and washed on the filter with 2000 ml of water. The washed crystals were dried under vacuum to yield about 75g of material containing about 9% reb A and about 91% reb B. The water solubility (at 25°C) of the material obtained was about 0. 1% (w/v). EXAMPLE 3 Preparation of stevia composition
    [0048]100 g of rebaudioside A produced by PureCircle Sdn. Bhd (Malaysia) containing 98.1% rebaudioside A, 0.3% stevioside, 0.2% rebaudioside C, 0.2% rebaudioside F, 0.4% rebaudioside B and 0.6% rebaudioside D were dispersed in 1000 ml aqueous KOH (1M) and incubated at 80°C for 7 hours. The temperature of the mixture was lowered to 20°C and the pH was adjusted to about pH 4.0 with sulfuric acid. The solution was kept under conditions of moderate agitation for 3-4 hours and a precipitate formed. The precipitate was filtered off and washed on the filter with 2000 ml of water. The washed crystals were dried under vacuum to yield about 71g of material containing about 99.1% of reb B. The water solubility (at 25°C) of the material obtained was about 0.1% (w/w). /v). EXAMPLE 4 Preparation of reb B
    75g of material prepared according to EXAMPLE 2 were suspended in 1000 ml of water. The temperature of the mixture was raised to 70°C. The suspension was kept under conditions of moderate agitation for 4 hours. The crystals were filtered and dried under vacuum to produce about 65g of material containing about 99.0% of reb B. The solubility in water (at 25°C) of the material obtained was about 0.1% ( p/v).EXAMPLE 5 Preparation of carboxylate salt of reb B
    100 g of reb B prepared according to EXAMPLE 4 were suspended in 1000 ml of water. The suspension was kept under moderately agitated conditions at room temperature for 1 hour. The pH of the mixture was adjusted to pH 11.0 with 1M KOH solution. The obtained mixture was stirred for 3 hours. The crystals were filtered and washed with water on the filter until the wash water reached a neutral pH. The crystalline material obtained was dried under vacuum to yield about 95g of material. The water solubility (at 25°C) of the material obtained was about 0.1% (w/v). EXAMPLE 6 Preparation of Soluble Stevia Composition
    50 g of the material prepared according to EXAMPLE 1 were mixed with 50 g of water and incubated in an oil bath with thermostat. The temperature was increased from 1°C per minute to 121°C. The mixture was kept at 121°C for 1 hour and then the temperature was lowered to room temperature (25°C) at 1°C per minute. The solution was dried using the YC-015 laboratory spray drier (Shanghai Pilotech Instrument & Equipment Co. Ltd., China) operating at an inlet temperature of 175°C and an outlet temperature of 100°C. About 47g of an amorphous powder was obtained with about 25% (w/v) solubility in water (at 25°C). EXAMPLE 7 Preparation of Soluble Stevia Composition
    42 g of reb A produced by PureCircle Sdn. Bhd (Malaysia) with purity of 99.2% (dry basis) and 8 g of reb B prepared according to EXAMPLE 4 were mixed with 50 g of water and incubated in an oil bath with thermostat. The temperature was increased from 1 °C per minute to 121 °C. The mixture was kept at 121°C for 1 hour and then the temperature was lowered to room temperature (25°C) at 1°C per minute. The solution was dried using the YC-015 laboratory spray drier (Shanghai Pilotech Instrument & Equipment Co. Ltd., China) operating at an inlet temperature of 175°C and an outlet temperature of 100°C. About 48g of an amorphous powder were obtained with about 1.5% (w/v) solubility in water (at 25°C). EXAMPLE 8 Preparation of Soluble Stevia Composition
    42 g of reb A produced by PureCircle Sdn. Bhd (Malaysia) with purity of 99.2% (dry basis) and 8 g of potassium salt of reb B prepared according to EXAMPLE 5 were mixed with 50 g of water and incubated in an oil bath with thermostat. The temperature was increased from 1°C per minute to 121°C. The mixture was kept at 121°C for 1 hour and then the temperature was lowered to room temperature (25°C) at 1°C per minute. The solution was dried using the YC-015 laboratory spray drier (Shanghai Pilotech Instrument & Equipment Co. Ltd., China) operating at an inlet temperature of 175°C and an outlet temperature of 100°C. About 49g of an amorphous powder were obtained with about 2.5% (w/v) solubility in water (at 25°C). EXAMPLE 9 Low Calorie Orange Juice Drink
    [0054] Orange concentrate (35%), citric acid (0.35%), ascorbic acid (0.05%), orange red color (0.01%), orange flavor (0.20%) and 0, 05% stevia composition, was mixed and completely dissolved in water (up to 100%) and pasteurized. The stevia composition was selected from a commercial stevia extract (containing 26% stevioside, 55% rebaudioside A and 16% other glycosides), a commercial rebaudioside A (containing 98.2% reb A) or material obtained from according to EXAMPLE 7 and EXAMPLE 8.
    [0055] The sensory evaluations of the samples are summarized in Table 1. The data show that the best results can be obtained using the composition obtained according to EXAMPLE 8. Particularly, drinks prepared with said composition exhibited a mouthfeel and profile. of perfect and complete flavor. Table 1 Evaluation of the orange juice drink samples


    [0056]The same method can be used to prepare juices and juice drinks from other fruits such as apples, lemons, apricots, cherries, pineapples, mangoes, etc. EXAMPLE 10 Zero Calorie Carbonated Drink
    [0057] Carbonated beverages made according to the formulas shown in Table 2 were prepared.

    [0058] The sensory properties were evaluated by 20 members. The results are summarized in Table 3.Table 3
    [0059] Evaluation of zero calorie carbonated beverage samples

    [0060] The above results show that beverages prepared using the composition obtained according to EXAMPLE 8 have the best organoleptic characteristics. EXAMPLE 11 Diet Cookies
    [0061] Flour (50.0%), margarine (30.0%), fructose (10.0%), maltitol (8.0%), whole milk (1.0%), salt (0.2% ), yeast (0.15%), vanilla (0.1%) and different stevia compositions (0.03%) were well mixed in a dough mixing machine. The obtained dough was molded and baked in an oven at 200°C for 15 minutes. Stevia compositions were selected from a commercial stevia extract (containing 26% stevioside, 55% rebaudioside A and 16% other glycosides), a commercial rebaudioside A (containing 98.2% reb A) and material obtained according to EXAMPLE 7 and EXAMPLE 8.
    [0062] The sensory properties were evaluated by 20 members. The best results were obtained in samples containing the composition obtained according to EXAMPLE 8. The members noted a perfect mouthfeel and complete flavor profile. EXAMPLE 12 Yogurt
    [0063]Different stevia (0.03%) and sucrose (4%) compositions were dissolved in low-fat milk. The stevia compositions were selected from a commercial stevia extract (containing 26% stevioside, 55% rebaudioside A and 16% other glycosides), a commercial rebaudioside A (containing 98.2% reb A) and the material obtained according to EXAMPLE 7 and EXAMPLE 8. After pasteurizing at 82°C for 20 minutes, the milk was cooled to 37°C. A starter culture (3%) was added and the mixture was then incubated at 37°C for 6 hours and then at 5°C for 12 hours.
    [0064] The sensory properties were evaluated by 20 members. The best results were obtained in samples containing the composition obtained according to EXAMPLE 8. The members noted a perfect mouthfeel and complete flavor profile.
    [0065] It is to be understood that the foregoing descriptions and specific embodiments shown herein are merely illustrative of the best mode of the invention and the principles thereof, and that modifications and additions can easily be made by those skilled in the art without departing from the spirit and scope of the invention which is therefore understood to be limited only by the scope of the appended claims.
    权利要求:
    Claims (4)
    [0001]
    1. A process for making a stevia composition comprising rebaudioside B, which can be used as a sweetener enhancer, a flavor enhancer and/or a sweetener, comprising the steps of: providing a stevia sweetener, wherein the stevia sweetener comprises rebaudioside A; provide an aqueous alkaline solution; disperse the stevia sweetener in the alkaline solution and incubate for 12 to 48 hours at 55 to 75°C to form a mixture; CHARACTERIZED by the fact that it comprises the additional steps of: cool the mixture to 10 to 30 °C and adjust the pH with acid to pH 3.0 to 4.0; incubate the mixture at low temperature to obtain a precipitate; separate the precipitate and wash it with water; drying the washed precipitate to obtain the stevia composition; the method further comprising the steps of: dispersing the stevia composition in water to prepare an aqueous dispersion of 5 to 50% (w/v) solids content; adding a base to the dispersion; incubate the mixture for 0.1 to 24 hours to facilitate partial or complete conversion of rebaudioside B carboxyl groups to a carboxylate salt to prepare a rebaudioside B carboxylate salt; and separate the suspended solids by filtration, wash these with water until a neutral pH of the wash water is obtained and dry the stevia composition comprising the carboxylate salt of rebaudioside B.
    [0002]
    2. Process according to claim 1, CHARACTERIZED by the fact that excess base is added to the dispersion to reach a pH of 6.5 to 14.
    [0003]
    3. Process according to claim 1, CHARACTERIZED by the fact that it comprises, before the steps of preparing the carboxylate salt of rebaudioside B, the additional steps of: suspending the stevia composition in water and incubating at a temperature of 50 to 100 °C for 1 to 3 hours; separating the stevia composition from the water and drying the stevia composition to obtain a purified stevia composition; wherein the purified stevia composition comprises rebaudioside B with greater than 99% purity.
    [0004]
    4. Process according to claim 1, CHARACTERIZED by the fact that it comprises, before the steps of preparing the carboxylate salt of rebaudioside B, the additional steps of: suspending the stevia composition in water at a ratio of 1:1 (p /p) to form a suspension; increase the temperature of the suspension by a gradient heating method of 1 °C per minute; keep the suspension at a temperature of 110 to 140 °C; decrease the temperature of the suspension to an ambient temperature by a cooling gradient of 1 °C per minute; spray dry the suspension to provide a stevia composition with greater than 20% solubility in water at room temperature.
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    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US3723410A|1970-12-01|1973-03-27|Amazon Natural Drug Co|Method of producing stevioside|
    JPS5227226B2|1975-06-04|1977-07-19|
    JPS525800A|1975-06-27|1977-01-17|Sanyo Kokusaku Pulp Co Ltd|Method of purifying stevioside|
    JPS5283731A|1976-01-01|1977-07-12|Ajinomoto Co Inc|Rebaudiosides|
    JPS52100500A|1976-02-18|1977-08-23|Japan Organo Co Ltd|Purification and concentration of aqueous stevioside extract|
    JPS52136200A|1976-05-12|1977-11-14|Daicel Chem Ind Ltd|Extraction purification of stevioside|
    JPS5338669A|1976-09-16|1978-04-08|Toyo Soda Mfg Co Ltd|Separation of natural sweetening agent|
    JPS5547871B2|1977-08-08|1980-12-02|
    JPS62157B2|1978-04-04|1987-01-06|Sanyo Kokusaku Pulp Co|
    US4219571A|1978-06-15|1980-08-26|Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo|Process for producing a sweetener|
    JPS561061B2|1978-09-11|1981-01-10|
    JPS5581567A|1978-12-13|1980-06-19|Res Inst For Prod Dev|Extraction and purification of stevioside|
    JPS5592400A|1978-12-29|1980-07-12|Daikin Ind Ltd|Purification of stevioside|
    JPS55120770A|1979-03-14|1980-09-17|Chisso Corp|Purification of stevioside solution|
    JPS55138372A|1979-04-13|1980-10-29|Chisso Corp|Purification of stevioside solution|
    JPS55162953A|1979-06-04|1980-12-18|Yamada Masami|Preparation of stevioside|
    JPS5742299B2|1980-01-09|1982-09-08|
    JPS56109568A|1980-02-01|1981-08-31|Maruzen Kasei Kk|Purification of stevia sweetening substance|
    JPS56121455A|1980-02-27|1981-09-24|Ajinomoto Co Inc|Separation of stevioside and rebaudioside a by crystallization|
    JPS56121454A|1980-02-27|1981-09-24|Ajinomoto Co Inc|Separation of stevioside and rebaudioside a by crystallization|
    JPS56121453A|1980-02-27|1981-09-24|Ajinomoto Co Inc|Separation of stevioside and rebaudioside a|
    JPS56160962A|1980-05-14|1981-12-11|Dick Fine Chem Kk|Purification of solution containing stevioside-type sweetening substance|
    JPS55159770A|1980-05-26|1980-12-12|Res Inst For Prod Dev|Extraction and purification of stevioside|
    JPS5742300B2|1980-06-05|1982-09-08|
    JPS575663A|1980-06-13|1982-01-12|Res Inst For Prod Dev|Purification of stevioside through extraction|
    JPS5746998A|1980-09-04|1982-03-17|Fuji Food:Kk|Preparation of stevioside|
    US4454290A|1980-09-22|1984-06-12|Dynapol|Stevioside analogs|
    JPH0245637B2|1980-10-30|1990-10-11|Tama Biochemical Co Ltd|
    JPS5846310B2|1980-11-19|1983-10-15|Maruzen Kasei Co Ltd|
    JPS632439B2|1981-02-12|1988-01-19|Hayashibara Seibutsu Kagaku Kenkyusho Kk|
    US4361697A|1981-05-21|1982-11-30|F. K. Suzuki International, Inc.|Extraction, separation and recovery of diterpene glycosides from Stevia rebaudiana plants|
    US4353889A|1981-06-11|1982-10-12|Dynapol|Rebaudioside analogs|
    JPS5820170A|1981-07-24|1983-02-05|Toshizo Fukushima|Preparation of sweetener|
    JPS5828247A|1981-08-10|1983-02-19|Mitsubishi Acetate Co Ltd|Purifying method of stevioside solution|
    JPS5828246A|1981-08-10|1983-02-19|Mitsubishi Acetate Co Ltd|Preparation of stevioside|
    JPS6337637B2|1982-02-27|1988-07-26|Dainippon Ink & Chemicals|
    JPS6257296B2|1982-06-04|1987-11-30|Sekisui Chemical Co Ltd|
    JPS6260057B2|1982-06-04|1987-12-14|Sekisui Chemical Co Ltd|
    JPH0375140B2|1982-09-09|1991-11-29|
    US4612942A|1984-03-08|1986-09-23|Stevia Company, Inc.|Flavor enhancing and modifying materials|
    US4657638A|1985-07-29|1987-04-14|University Of Florida|Distillation column|
    US4599403A|1985-10-07|1986-07-08|Harold Levy|Method for recovery of stevioside|
    JPS62166861A|1986-01-20|1987-07-23|Sanpack:Kk|Extraction and purification of sweetener component from dry leaf of stevia|
    EP0302948B1|1987-07-21|1993-12-01|Roger H. Giovanetto|Process for obtaining steviosides from plants|
    JP3111203B2|1987-12-26|2000-11-20|中里隆憲|Plants belonging to new Stevia varieties|
    DE3810681C2|1988-03-29|1993-06-03|Udo 7000 Stuttgart De Kienle|
    JP2898688B2|1990-03-14|1999-06-02|日本製紙株式会社|Highly sweetened sugar-added stevia sweetener and process for producing the same|
    CN1024348C|1990-05-23|1994-04-27|孟凡彬|Process for extraction of sweet stevia by ordinary resin|
    US5576042A|1991-10-25|1996-11-19|Fuisz Technologies Ltd.|High intensity particulate polysaccharide based liquids|
    JPH067108A|1992-06-23|1994-01-18|P C C Technol:Kk|Method for extracting and separating sweet substance of stevia rebaudiana bertoni|
    TW293036B|1992-11-27|1996-12-11|Takeda Pharm Industry Co Ltd|
    JPH06192283A|1992-12-17|1994-07-12|Ikeda Pan:Kk|Method for production pure rebaudioside a|
    CN1032651C|1993-09-21|1996-08-28|袁斯鸣|Method for purifying stevioside|
    JP3436317B2|1993-11-24|2003-08-11|大日本インキ化学工業株式会社|Method for producing stevia sweetener|
    JPH07177862A|1993-12-24|1995-07-18|Morita Kagaku Kogyo Kk|Slightly water-soluble sweetener|
    US5549757A|1994-06-10|1996-08-27|Ingredient Technology Corporation|Process for recrystallizing sugar and product thereof|
    JPH08214A|1994-06-17|1996-01-09|Ikeda Pan:Kk|Rebaudioside a-based sweetener and its production|
    JP3262458B2|1994-07-29|2002-03-04|キヤノン株式会社|Recording device|
    CN1112565A|1995-03-06|1995-11-29|北京市环境保护科学研究院|Technology for extracting stevioside by membrane method combined technique|
    JP3352860B2|1995-10-19|2002-12-03|守田化学工業株式会社|α-Glucosylated Stevia sweetener|
    RU2111969C1|1995-11-08|1998-05-27|Республиканская научно-исследовательская лаборатория по биологически активным веществам|Method of stevioside preparing|
    US5962678A|1996-09-13|1999-10-05|Alberta Research Council|Method of extracting selected sweet glycosides from the Stevia rebaudiana plant|
    TW557327B|1996-11-08|2003-10-11|Hayashibara Biochem Lab|Kojibiose phosphorylase, its preparation and uses|
    JP2002262822A|1997-01-30|2002-09-17|Morita Kagaku Kogyo Kk|Sweetener obtained from plant body of variety of stevia rebaudiana cultivatable from seed|
    JPH10271928A|1997-01-30|1998-10-13|Morita Kagaku Kogyo Kk|New plant belonging to stevia rabaudiana berton.|
    RU2123267C1|1997-06-24|1998-12-20|Дмитриенко Николай Васильевич|Method of preparing concentrate of extract from powder of stevia herb|
    RU2156083C2|1997-06-24|2000-09-20|Дмитриенко Николай Васильевич|Method of obtaining extract from stevia grass|
    US5972120A|1997-07-19|1999-10-26|National Research Council Of Canada|Extraction of sweet compounds from Stevia rebaudiana Bertoni|
    JP3646497B2|1997-12-22|2005-05-11|味の素株式会社|Granular sweetener|
    CN1078217C|1998-02-18|2002-01-23|南开大学|Adsorption resin method for conectrating and separating vegetable baudy glucoside from stevioside|
    CN1098860C|1998-06-08|2003-01-15|江苏省中国科学院植物研究所|Process for separating and concentrating high-quality stevioside|
    JP2000236842A|1998-12-24|2000-09-05|Nippon Paper Industries Co Ltd|Stevia sweetener|
    US6228996B1|1999-02-24|2001-05-08|James H. Zhou|Process for extracting sweet diterpene glycosides|
    RU2167544C2|1999-03-09|2001-05-27|Краснодарский научно-исследовательский институт хранения и переработки сельскохозяйственной продукции|Method of preparing extract from plant stevia rebaudiana bertoni for winemaking|
    US20020132320A1|2001-01-10|2002-09-19|Wang Peng George|Glycoconjugate synthesis using a pathway-engineered organism|
    RU2198548C1|2001-06-01|2003-02-20|Общество с ограниченной ответственностью Научно-производственное холдинговое объединение "СТЕВИЯ-АГРОМЕДФАРМ"|Method of producing extract from plants stevia rebaudiana bertoni|
    CN1132840C|2001-10-24|2003-12-31|青岛创升生物科技有限公司|Stevioside glycoside refining process|
    CA2474082A1|2002-02-14|2003-08-21|Novozymes A/S|Process for producing starch hydrolysate|
    SE0200539D0|2002-02-25|2002-02-25|Metcon Medicin Ab|Granulation process and starch granulate|
    CN1237182C|2002-06-25|2006-01-18|山东华仙甜菊股份有限公司|Process for improving taste of ribaudiose|
    WO2004081022A2|2003-03-10|2004-09-23|Genencor International Inc.|Grain compositions containing pre-biotic isomalto-oligosaccharides and methods of making and using same|
    AU2005223688A1|2004-03-17|2005-09-29|Cargill, Incorporated|Low glycemic sweeteners and products made using the same|
    US7476248B2|2004-04-06|2009-01-13|Alcon, Inc.|Method of calculating the required lens power for an opthalmic implant|
    US7923552B2|2004-10-18|2011-04-12|SGF Holdings, LLC|High yield method of producing pure rebaudioside A|
    US7838044B2|2004-12-21|2010-11-23|Purecircle Sdn Bhd|Extraction, separation and modification of sweet glycosides from the Stevia rebaudiana plant|
    US20060142555A1|2004-12-23|2006-06-29|Council Of Scientific And Industrial Research|Process for production of steviosides from stevia rebaudiana bertoni|
    WO2006072878A1|2005-01-07|2006-07-13|Ranbaxy Laboratories Limited|Oral dosage forms of sertraline having controlled particle size and processes for their preparation|
    WO2006072879A1|2005-01-07|2006-07-13|Ranbaxy Laboratories Limited|Preparation of sweetener tablets of stevia extract by dry granulation methods|
    US7838011B2|2005-02-14|2010-11-23|Pankaj Modi|Stabilized protein compositions for topical administration and methods of making same|
    US8334006B2|2005-10-11|2012-12-18|Purecircle Sdn Bhd|Process for manufacturing a sweetener and use thereof|
    MX353094B|2009-11-12|2017-12-19|Purecircle Usa Inc|Granulation of a stevia sweetener.|
    US7862845B2|2005-10-11|2011-01-04|Purecircle Sdn Bhd|Process for manufacturing a sweetener and use thereof|
    US7807206B2|2005-10-11|2010-10-05|Purecircle Sdn Bhd|Sweetner and use|
    US8790730B2|2005-10-11|2014-07-29|Purecircle Usa|Process for manufacturing a sweetener and use thereof|
    US8337927B2|2005-10-11|2012-12-25|Purecircle Sdn Bhd|Process for manufacturing a sweetener and use thereof|
    US8318232B2|2005-10-11|2012-11-27|Purecircle Sdn Bhd|Sweetner and use|
    US20070116822A1|2005-11-23|2007-05-24|The Coca-Cola Company|High-potency sweetener composition with saponin and compositions sweetened therewith|
    US20070116829A1|2005-11-23|2007-05-24|The Coca-Cola Company|Pharmaceutical Composition with High-Potency Sweetener|
    US20070116800A1|2005-11-23|2007-05-24|The Coca-Cola Company|Chewing Gum with High-Potency Sweetener|
    US8956677B2|2005-11-23|2015-02-17|The Coca-Cola Company|High-potency sweetener composition with glucosamine and compositions sweetened therewith|
    US20070116823A1|2005-11-23|2007-05-24|The Coca-Cola Company|High-potency sweetener for hydration and sweetened hydration composition|
    US9144251B2|2005-11-23|2015-09-29|The Coca-Cola Company|High-potency sweetener composition with mineral and compositions sweetened therewith|
    US8377491B2|2005-11-23|2013-02-19|The Coca-Cola Company|High-potency sweetener composition with vitamin and compositions sweetened therewith|
    US8962058B2|2005-11-23|2015-02-24|The Coca-Cola Company|High-potency sweetener composition with antioxidant and compositions sweetened therewith|
    US8524303B2|2005-11-23|2013-09-03|The Coca-Cola Company|High-potency sweetener composition with phytosterol and compositions sweetened therewith|
    US8367138B2|2005-11-23|2013-02-05|The Coca-Cola Company|Dairy composition with high-potency sweetener|
    US8367137B2|2005-11-23|2013-02-05|The Coca-Cola Company|High-potency sweetener composition with fatty acid and compositions sweetened therewith|
    US20070116833A1|2005-11-23|2007-05-24|The Coca-Cola Company|High-Potency Sweetener Composition with Calcium and Compositions Sweetened Therewith|
    US8945652B2|2005-11-23|2015-02-03|The Coca-Cola Company|High-potency sweetener for weight management and compositions sweetened therewith|
    US8512789B2|2005-11-23|2013-08-20|The Coca-Cola Company|High-potency sweetener composition with dietary fiber and compositions sweetened therewith|
    US8940351B2|2005-11-23|2015-01-27|The Coca-Cola Company|Baked goods comprising high-potency sweetener|
    US8993027B2|2005-11-23|2015-03-31|The Coca-Cola Company|Natural high-potency tabletop sweetener compositions with improved temporal and/or flavor profile, methods for their formulation, and uses|
    US8524304B2|2005-11-23|2013-09-03|The Coca-Cola Company|High-potency sweetener composition with probiotics/prebiotics and compositions sweetened therewith|
    US9101160B2|2005-11-23|2015-08-11|The Coca-Cola Company|Condiments with high-potency sweetener|
    ES2611887T3|2005-11-23|2017-05-11|The Coca-Cola Company|Natural high potency sweetener compositions with improved temporal profile and / or aroma profile|
    US20070116820A1|2005-11-23|2007-05-24|The Coca-Cola Company|Edible gel compositions comprising high-potency sweeteners|
    US20070116836A1|2005-11-23|2007-05-24|The Coca-Cola Company|High-Potency Sweetener Composition for Treatment and/or Prevention of Osteoporosis and Compositions Sweetened Therewith|
    US8435588B2|2005-11-23|2013-05-07|The Coca-Cola Company|High-potency sweetener composition with an anti-inflammatory agent and compositions sweetened therewith|
    US8435587B2|2005-11-23|2013-05-07|The Coca-Cola Company|High-potency sweetener composition with long-chain primary aliphatic saturated alcohol and compositions sweetened therewith|
    US20070116839A1|2005-11-23|2007-05-24|The Coca-Cola Company|High-Potency Sweetener Composition With C-Reactive Protein Reducing Substance and Compositions Sweetened Therewith|
    US8956678B2|2005-11-23|2015-02-17|The Coca-Cola Company|High-potency sweetener composition with preservative and compositions sweetened therewith|
    US20070116831A1|2005-11-23|2007-05-24|The Coca-Cola Company|Dental Composition with High-Potency Sweetener|
    US20070134391A1|2005-11-23|2007-06-14|The Coca-Cola Company|High-Potency Sweetener Composition for Treatment and/or Prevention of Autoimmune Disorders and Compositions Sweetened Therewith|
    US20070116825A1|2005-11-23|2007-05-24|The Coca-Cola Company|Confection with High-Potency Sweetener|
    US8940350B2|2005-11-23|2015-01-27|The Coca-Cola Company|Cereal compositions comprising high-potency sweeteners|
    US7927851B2|2006-03-21|2011-04-19|Vineland Research And Innovation Centre|Compositions having ent-kaurenoic acid 13-hydroxylase activity and methods for producing same|
    US8791253B2|2006-06-19|2014-07-29|The Coca-Cola Company|Rebaudioside A composition and method for purifying rebaudioside A|
    EP2049673B1|2006-08-11|2011-04-13|Danisco US Inc.|Native grain amylases in enzyme combinations for granular starch hydrolysis|
    EP2070504A4|2006-09-20|2010-10-27|Yuyama Mfg Co Ltd|Medicine packaging apparatus|
    FR2906712A1|2006-10-09|2008-04-11|France Chirurgie Instr|MEASURE PLUG WITH SIMPLIFIED INSTALLATION.|
    FR2906973B1|2006-10-17|2009-01-16|Roquette Freres|GRANULATED EDULCORING COMPOSITION|
    US20080102497A1|2006-10-31|2008-05-01|Dominic Wong|Enzymatic hydrolysis of starch|
    US20080107787A1|2006-11-02|2008-05-08|The Coca-Cola Company|Anti-Diabetic Composition with High-Potency Sweetener|
    US9101161B2|2006-11-02|2015-08-11|The Coca-Cola Company|High-potency sweetener composition with phytoestrogen and compositions sweetened therewith|
    US8017168B2|2006-11-02|2011-09-13|The Coca-Cola Company|High-potency sweetener composition with rubisco protein, rubiscolin, rubiscolin derivatives, ace inhibitory peptides, and combinations thereof, and compositions sweetened therewith|
    FI20070521A|2006-11-10|2008-05-11|Atacama Labs Oy|Grains, tablets and granulation process|
    CN101200480B|2006-12-15|2011-03-30|成都华高药业有限公司|Rebaudioside A extraction method|
    EP2124633B1|2007-01-22|2012-03-07|Cargill, Incorporated|Method of producing purified rebaudioside a compositions using solvent/antisolvent crystallization|
    US9877500B2|2007-03-14|2018-01-30|Concentrate Manufacturing Company Of Ireland|Natural beverage products|
    BRPI0701736A|2007-04-05|2008-07-15|Stevia Natus Produtos Naturais|physical-chemical industrial process of obtaining natural sweeteners and pure active principles of stevioside and rebaudioside a from stevia leaf without the use of organic solvents for the manufacture of sweeteners|
    CN101932719B|2007-04-26|2014-04-02|株式会社林原|Branched -glucan, -glucosyltransferase producing the same, method for producing the same and use thereof|
    US8030481B2|2007-05-21|2011-10-04|The Coca-Cola Company|Stevioside polymorphic and amorphous forms, methods for their formulation, and uses|
    US8709521B2|2007-05-22|2014-04-29|The Coca-Cola Company|Sweetener compositions having enhanced sweetness and improved temporal and/or flavor profiles|
    US20080292775A1|2007-05-22|2008-11-27|The Coca-Cola Company|Delivery Systems for Natural High-Potency Sweetener Compositions, Methods for Their Formulation, and Uses|
    US20080292765A1|2007-05-22|2008-11-27|The Coca-Cola Company|Sweetness Enhancers,Sweetness Enhanced Sweetener Compositions, Methods for Their Formulation, and Uses|
    WO2009006208A2|2007-06-29|2009-01-08|Mcneil Nutritionals, Llc|Stevia-containing tabletop sweeteners and methods of producing same|
    US7964232B2|2007-09-17|2011-06-21|Pepsico, Inc.|Steviol glycoside isomers|
    TWI475963B|2008-02-25|2015-03-11|Coca Cola Co|Rebaudioside a derivative products and methods for making|
    FR2929533B1|2008-04-03|2010-04-30|Novasep|MULTICOLOUR GRADIENT SEPARATION PROCESS.|
    US20110033525A1|2008-04-11|2011-02-10|Zhijun Liu|Diterpene Glycosides as Natural Solubilizers|
    US8321670B2|2008-07-11|2012-11-27|Bridgewater Systems Corp.|Securing dynamic authorization messages|
    KR101345172B1|2008-07-18|2013-12-27|엘지디스플레이 주식회사|Electrophoretic display deivce|
    EP2416670A4|2009-04-09|2014-05-21|Cargill Inc|Sweetener composition comprising high solubility form of rebaudioside a and method of making|
    KR20120027363A|2009-06-16|2012-03-21|이피씨 내추럴 프로덕츠 컴퍼니, 리미티드|Composition comprising rebaudioside d for reducing or eliminating aftertaste and preparation method thereof|
    US8299224B2|2009-10-15|2012-10-30|Purecircle Sdn Bhd|High-purity Rebaudioside D|
    US8703224B2|2009-11-04|2014-04-22|Pepsico, Inc.|Method to improve water solubility of Rebaudioside D|
    US20110111115A1|2009-11-06|2011-05-12|Jingang Shi|Rebaudioside a polymorphs and methods to prepare them|
    US9284570B2|2010-11-30|2016-03-15|Massachusetts Institute Of Technology|Microbial production of natural sweeteners, diterpenoid steviol glycosides|
    RU2719036C2|2009-12-28|2020-04-16|Дзе Кока-Кола Компани|Sweetness enhancers, compositions and methods thereof|
    US20110189360A1|2010-02-04|2011-08-04|Pepsico, Inc.|Method to Increase Solubility Limit of Rebaudioside D in an Aqueous Solution|
    NZ604915A|2010-06-02|2014-10-31|Evolva Nutrition Inc|Recombinant production of steviol glycosides|
    US9090647B2|2010-12-13|2015-07-28|Cargill, Incorporated|Crystalline forms of rebaudioside B|
    JP6290624B2|2010-12-13|2018-03-07|カーギル・インコーポレイテッド|Glycoside mixture|
    MX338850B|2010-12-24|2016-05-02|Daicel Corp|Acetic acid production method.|
    EP3395184A1|2011-01-28|2018-10-31|Tate & Lyle Ingredients Americas LLC|Stevia blends containing rebaudioside b|
    MX360826B|2011-02-10|2018-11-16|Purecircle Usa|Stevia composition.|
    PL2486806T3|2011-02-10|2019-07-31|Purecircle Usa|Stevia composition|
    US8257948B1|2011-02-17|2012-09-04|Purecircle Usa|Method of preparing alpha-glucosyl Stevia composition|
    US8318459B2|2011-02-17|2012-11-27|Purecircle Usa|Glucosyl stevia composition|
    US9795156B2|2011-03-17|2017-10-24|E.P.C Plant Pharmaceutical Technology Co., Ltd|Rebaudioside B and derivatives|
    SG10201606563PA|2011-08-08|2016-10-28|Evolva Sa|Recombinant production of steviol glycosides|
    JP6192283B2|2012-10-11|2017-09-06|スリーエム イノベイティブ プロパティズ カンパニー|Fastener parts|KR20120027363A|2009-06-16|2012-03-21|이피씨내추럴 프로덕츠 컴퍼니, 리미티드|Composition comprising rebaudioside d for reducing or eliminating aftertaste and preparation method thereof|
    US10696706B2|2010-03-12|2020-06-30|Purecircle Usa Inc.|Methods of preparing steviol glycosides and uses of the same|
    US9578895B2|2010-08-23|2017-02-28|EpcNatural Products Co., Ltd.|Rebaudioside A and stevioside compositions|
    EP3395184A1|2011-01-28|2018-10-31|Tate & Lyle Ingredients Americas LLC|Stevia blends containing rebaudioside b|
    US8962698B2|2011-01-28|2015-02-24|Tate & Lyle Ingredients Americas Llc|Rebaudioside-mogroside V blends|
    WO2013036366A1|2011-09-07|2013-03-14|Purecircle Usa Inc.|Highly soluble stevia sweetener|
    US9107436B2|2011-02-17|2015-08-18|Purecircle Sdn Bhd|Glucosylated steviol glycoside as a flavor modifier|
    US9795156B2|2011-03-17|2017-10-24|E.P.CPlant Pharmaceutical Technology Co., Ltd|Rebaudioside B and derivatives|
    US9877501B2|2011-06-03|2018-01-30|Purecircle Sdn Bhd|Stevia composition|
    US9771434B2|2011-06-23|2017-09-26|Purecircle Sdn Bhd|Products from stevia rebaudiana|
    GB201217700D0|2012-08-01|2012-11-14|Tate & Lyle Ingredients|Sweetener compositions containing rebaudioside B|
    BR112015014876B1|2012-12-19|2020-11-03|Purecircle Sdn Bhd|rebaudioside x amorphous, sweetening composition comprising said rebaudioside x, method for preparing rebaudioside x amorphous and method for preparing a drink|
    US10952458B2|2013-06-07|2021-03-23|Purecircle Usa Inc|Stevia extract containing selected steviol glycosides as flavor, salty and sweetness profile modifier|
    BR112015030650B1|2013-06-07|2021-02-23|Purecircle Usa Inc|flavor and aroma modifying composition comprising steviol glycosides, their food or drink product and their method for increasing the flavor and aroma intensity or improving salt perception and reducing the sodium content of a food or drink product|
    US10905146B2|2013-07-12|2021-02-02|The Coca-Cola Company|Compositions for improving rebaudioside M solubility|
    JP2017500863A|2013-12-16|2017-01-12|カーギル・インコーポレイテッド|Stabilized steviol glycosides in concentrated syrup|
    EP3099185A4|2014-01-29|2017-11-01|Cargill, Incorporated|Stable suspension of a steviol glycoside in concentrated syrup|
    US20150223505A1|2014-02-12|2015-08-13|Purecircle Usa Inc.|Stevia composition, production method and uses|
    US10264811B2|2014-05-19|2019-04-23|Epc Natural Products Co., Ltd.|Stevia sweetener with improved solubility|
    US10357052B2|2014-06-16|2019-07-23|Sweet Green Fields USA LLC|Rebaudioside A and stevioside with improved solubilities|
    US10485256B2|2014-06-20|2019-11-26|Sweet Green Fields International Co., Limited|Stevia sweetener with improved solubility with a cyclodextrin|
    CN107105686B|2014-09-02|2021-12-24|谱赛科美国股份有限公司|Stevia extract rich in rebaudioside D, E, N and/or O and preparation method thereof|
    CN108601382A|2015-08-18|2018-09-28|谱赛科美国股份有限公司|steviol glycoside solution|
    AU2018374866A1|2017-11-28|2020-06-18|The Coca-Cola Company|Process for preparing concentrated solutions of steviol glycosides and mogrosides, and uses|
    WO2019183493A1|2018-03-23|2019-09-26|Sweet Green Fields Usa, Llc|Steviol glycosides with improved solubilities, taste profiles and flavoring effects|
    法律状态:
    2020-08-18| B06F| Objections, documents and/or translations needed after an examination request according [chapter 6.6 patent gazette]|
    2020-08-25| B06U| Preliminary requirement: requests with searches performed by other patent offices: procedure suspended [chapter 6.21 patent gazette]|
    2021-02-02| B06A| Patent application procedure suspended [chapter 6.1 patent gazette]|
    2021-05-11| B09A| Decision: intention to grant [chapter 9.1 patent gazette]|
    2021-07-20| B16A| Patent or certificate of addition of invention granted [chapter 16.1 patent gazette]|Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 11/08/2011, OBSERVADAS AS CONDICOES LEGAIS. |
    优先权:
    申请号 | 申请日 | 专利标题
    US201161491441P| true| 2011-05-31|2011-05-31|
    US61/491.441|2011-05-31|
    PCT/US2011/047498|WO2012166163A1|2011-05-31|2011-08-11|Stevia composition|
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