High-solubility stevioside solution as well as preparation method and application thereof
By mixing solubilizing substances such as lactic acid, malic acid, citric acid or tartaric acid with steviol glycosides, the problem of insufficient solubility of steviol glycosides in water is solved, and the preparation of steviol glycoside solutions with high solubility, stability and low cost is achieved.
Patent Information
- Application Number
- CN202411656803.2
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2024-11-19
- Publication Date
- 2025-01-21
- Estimated Expiration
- 2044-11-19
AI Technical Summary
The poor solubility of high-purity stevioside in water limits its application in liquid formulations, especially in liquid concentration systems.
Mixed soluble substances such as lactic acid, apple acid, citric acid, or citic acid are mixed with chrysanthemum glycoside to improve the solubility of stevia glycoside by disturbing mixing and static placement.
The solubility of steviol glycosides is significantly improved, the solubilization effect is obvious, the solution maintains good stability during storage, dilution and freeze-drying and reconstitution, and the preparation process is simple and the cost is low.
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Figure CN119326109A_ABST
Abstract
Description
Technical Field
[0001] The invention relates to the technical field of food additives, and in particular to a high-soluble stevioside solution and a preparation method and application thereof. Background Art
[0002] Low sugar and sugar reduction are the main trends in food and beverage consumer products. Calorie-free or low-calorie sweeteners have gradually become substitutes for sucrose to meet consumer demand. Artificial sweeteners such as acesulfame potassium, aspartame, neotame, saccharin and sucralose are all high-intensity synthetic compounds, many of which have been proven to be carcinogenic and associated with various other diseases. Therefore, the use of natural sweeteners has been widely praised.
[0003] As the world's third-generation sugar source, stevioside is a natural non-nutritive sweetener with the characteristics of high sweetness (250-450 times that of sucrose) and low caloric value (1 / 300 of sucrose). It also has the effects of lowering blood pressure, lowering blood sugar, preventing dental caries and anti-tumor, and has been widely used in food or beverages. From the molecular structure level, stevioside is an enantio-kaurene diterpenoid glycoside, composed of a hydrophobic steviol skeleton and a hydrophilic sugar group. Currently known sweet ingredients include stevioside, rebaudioside A (RA, Formula 1), rebaudioside B, rebaudioside C, rebaudioside D (RD, Formula 2), rebaudioside E, rebaudioside F, rebaudioside M (RM, Formula 3), rubusoside, dulcoside and steviolbioside, etc. The difference in their molecular structure lies in the difference in the number and distribution of hydrophilic sugar groups, which further leads to differences in their taste and physical and chemical properties.
[0004]
[0005] Formula 1 Molecular structure of rebaudioside A
[0006]
[0007] Formula 2 Molecular structure of rebaudioside D
[0008]
[0009] Formula 3 Molecular structure of rebaudioside M
[0010] The application of high-purity steviosides in food and beverages is challenging because of their poor solubility in water. For example, the solubility of rebaudioside A is about 0.8%, rebaudioside B is 0.01%-0.02%, rebaudioside D is about 0.04%, and rebaudioside M is about 0.1%. This greatly limits their application in liquid formulations, especially in liquid concentrated systems such as beverage syrups, flavor concentrates, and tabletop concentrated sweeteners.
[0011] In order to improve the solubility of stevioside in water, the existing methods are as follows:
[0012] 1) A Chinese invention patent application (publication number CN104530448A) discloses a method for preparing a high-solubility steviol glycoside complex. This method uses hydroxypropyl-β-cyclodextrin to coat steviol glycoside to obtain a high-solubility steviol glycoside complex, but this method uses solvents such as methanol, ethanol and isopropanol, and non-edible substances need to be further removed, and its safety remains to be evaluated.
[0013] 2) A Chinese invention patent application (publication number CN111315233B) discloses a steviol glycoside solubilizer. The system is based on gallic acid, mandelic acid, and pyromellitic acid, and corn starch fiber or gellan gum is added to form a steviol glycoside solubilizer, but the solubilization effect of this method is limited, and the storage stability of the solution needs further investigation.
[0014] Therefore, it is of great significance to develop a stevioside solution with high solubility, high stability, low cost and simple preparation process. Summary of the invention
[0015] In view of the deficiencies in the prior art, the object of the present invention is to provide a high-soluble stevioside solution and a preparation method and application thereof.
[0016] The technical solution adopted by the present invention is:
[0017] A high-solubility stevioside solution comprises stevioside and a solubilizing substance aqueous solution; the mass molar concentration of the solubilizing substance in the solubilizing substance aqueous solution is greater than 0 to the solubility (saturation concentration); the mass percentage concentration of the stevioside in the high-solubility stevioside solution is from the solubility in pure water to the solubility in the solubilizing substance aqueous solution; the solubilizing substance comprises at least one of lactic acid, malic acid, citric acid and tartaric acid.
[0018] The high-solubility stevioside solution of the invention has good fluidity and a clear and transparent appearance.
[0019] Lactic acid has the following structure:
[0020]
[0021] Malic acid has the following structure:
[0022]
[0023] Citric acid has the following structure:
[0024]
[0025] Tartaric acid has the following structure:
[0026]
[0027] Preferably, the solubilizing substance further comprises at least one of lactate, malate, citrate and tartrate;
[0028] Further preferably, the mass content of lactic acid, malic acid, citric acid and tartaric acid in the solubilizing substance is not less than 0.5%;
[0029] Preferably, the mass molar concentration of the solubilizing substance in the aqueous solution of the solubilizing substance is 1×10 -5 ~5×10 - 2 mol / g;
[0030] Further preferably, the mass molar concentration of the solubilizing substance in the aqueous solution of the solubilizing substance is 2.5×10 -3 ~1.5×10 -2 mol / g.
[0031] Preferably, the mass percentage concentration of steviol glycoside in the high-soluble steviol glycoside solution is 0.10% to 15%.
[0032] Further preferably, the mass percentage concentration of steviol glycoside in the high-soluble steviol glycoside solution is 0.10% to 10%.
[0033] Preferably, the steviol glycoside includes at least one of rebaudioside A, rebaudioside D, rebaudioside M, stevioside, rebaudioside B, rebaudioside C, rebaudioside E, rebaudioside F, rubusoside, dulcoside and steviolbioside.
[0034] Further preferably, the steviol glycoside includes at least one of rebaudioside A, rebaudioside D and rebaudioside M.
[0035] More preferably, when the stevioside is rebaudioside A, the mass percentage concentration of rebaudioside A is 0.9% to 12%;
[0036] More preferably, when the steviol glycoside is rebaudioside D, the mass percentage concentration of rebaudioside D is 0.12% to 0.31%;
[0037] More preferably, when the stevioside is rebaudioside M, the mass percentage concentration of rebaudioside M is 0.48% to 0.63%.
[0038] The method for preparing the above-mentioned high-soluble steviol glycoside solution comprises the following steps:
[0039] The solubilizing substance is dissolved in water to obtain an aqueous solution of the solubilizing substance, and then a certain amount of stevioside is added to the aqueous solution of the solubilizing substance, and the mixture is stirred and mixed at 10° C. to 60° C., and allowed to stand to obtain a high-soluble stevioside solution.
[0040] Preferably, the disturbance mixing time is 30s to 300s.
[0041] Preferably, the disturbance is a mechanical disturbance;
[0042] Further preferably, the mechanical disturbance is one of electromagnetic stirring, vortex oscillation, shear homogenization, ultrasonic homogenization, and grinding homogenization.
[0043] Preferably, the standing time is 12 to 36 hours.
[0044] The application of the above-mentioned high-soluble stevioside solution or the high-soluble stevioside solution obtained by the above-mentioned preparation method in the preparation of food or beverage products, wherein the solution is used directly or after dilution. The high-soluble stevioside solution of the present invention is used as a liquid concentrate and is suitable for liquid concentrate systems such as table sweeteners or beverage syrups.
[0045] A high-solubility stevioside complex is obtained by freeze-drying or spray-drying the high-solubility stevioside solution or the high-solubility stevioside solution obtained by the above-mentioned preparation method. The obtained high-solubility stevioside complex is a stevioside product in the form of solid powder.
[0046] Preferably, the freeze-drying temperature is -30°C to -50°C, and the time is 12 to 36 hours.
[0047] Application of the above-mentioned high-solubility stevioside complex in the preparation of food or beverage products: The high-solubility stevioside complex of the present invention is used directly or after being dissolved.
[0048] The high-solubility stevioside complex solid powder of the present invention presents a surface morphology that is conducive to sufficient contact with water or water penetration under a scanning electron microscope, and has good re-dissolution stability.
[0049] Beneficial effects of the present invention: The stevioside complex of the present invention has the advantages of high content, high stability, low cost, simple preparation process, etc., and is suitable for large-scale production and application.
[0050] Specifically:
[0051] 1) The steviol glycoside solution of the present invention increases the solubility of steviol glycoside by 1 to 15 times, and has a significant solubilization effect.
[0052] 2) The stevioside solution of the present invention remains relatively clear, transparent and uniform after being placed at room temperature for 30 days, without obvious flocs or precipitation, and has good storage stability; it remains clear, transparent and uniform after being diluted according to actual application scenarios, and has good dilution stability; the solution remains clear, transparent and uniform after the freeze-dried sample is re-dissolved, and has good freeze-drying and re-dissolution stability.
[0053] 3) Compared with the existing solubilization methods, the preparation method of the stevioside solution of the present invention has a simpler process and milder conditions (such as no heating step), greatly reduces the production cost, and is suitable for large-scale production applications. BRIEF DESCRIPTION OF THE DRAWINGS
[0054] Figure 1 This is the appearance of solution samples 1, 2, 4, and 6 in Example 3 before dilution.
[0055] Figure 2 This is the appearance picture and SEM picture of freeze-dried sample 2 in Example 4.
[0056] Figure 3 This is the appearance picture and SEM picture of freeze-dried sample 3 in Example 4.
[0057] Figure 4 The following are the appearance picture and SEM picture of freeze-dried sample 4 in Example 4.
[0058] Figure 5 : This is the appearance picture and SEM picture of freeze-dried sample 5 in Example 4.
[0059] Figure 6 This is the appearance picture and SEM picture of freeze-dried sample 6 in Example 4. DETAILED DESCRIPTION
[0060] The present invention is described in detail below in conjunction with embodiments, the purpose of which is only to better illustrate the content of the present invention but not to limit the present invention in any way.
[0061] Embodiment 1:
[0062] Experiment on the solubilization effect of different solubilizing substances on stevioside:
[0063] According to Table 1, different solubilizing substances were weighed and mixed in water to prepare a certain concentration of solubilizing substance aqueous solution, and an excess of stevioside was directly added thereto, and the two were fully mixed by vortex oscillation at an oscillation rate of 1000 rpm at 25°C for 180s; the solution was allowed to stand for 24 hours and then centrifuged to obtain the supernatant, and the solubility of stevioside was determined by HPLC (refer to "GB 1886.355-2022 National Food Safety Standard Food Additive Stevioside"). The experimental results of the solubilization effect of different solubilizing substances on stevioside are shown in Table 1 below:
[0064] Table 1 Experimental results of solubilization effect of different solubilizing substances on stevioside
[0065]
[0066]
[0067] From Table 1, we can see that:
[0068] 1) The different solubilizing substances mentioned above have a significant solubilizing effect on different types of steviosides;
[0069] 2) The solubility of stevioside increases with the increase of the content of solubilizing substances;
[0070] 3) The same solubilizing substance has different solubilizing effects on different types of steviosides, which may be attributed to the differences in the molecular structures of different types of steviosides.
[0071] Comparative Example 1:
[0072] According to Table 2, different other substances were weighed and mixed into water to prepare an aqueous solution of a certain concentration, and an excess of stevioside was directly added thereto. The solution was vortexed at an oscillation rate of 1000 rpm for 180 s at 25°C to fully mix the two. The solution was allowed to stand for 24 hours and then centrifuged to obtain the supernatant. The solubility of stevioside was determined by HPLC (refer to "GB 1886.355-2022 National Food Safety Standard Food Additive Stevioside"). The experimental results of the solubilization effect of different other substances on stevioside are shown in the following table:
[0073] Table 2 Experimental results of solubilization effect of different other substances on stevioside
[0074]
[0075] As shown in Table 2, although the above-mentioned other substances have similar structures or properties to the solubilizing substances of the present invention, the other substances at the same concentration have little solubilizing effect on steviol glycosides and may even reduce the solubility of steviol glycosides. Some other substances are limited in their concentration due to their low solubility, such as alanine, succinic acid and aspartic acid, which have solubility limitations. Therefore, the steviol glycoside solubilizing substances need to have specific structures and properties.
[0076] Embodiment 2:
[0077] Storage stability experiment of high solubility stevioside solution:
[0078] According to Table 3, different solubilizing substances were weighed and added to water to prepare an aqueous solution of a certain concentration of the solubilizing substance, to which an appropriate amount of rebaudioside A was added, and the mixture was stirred at 25°C and a stirring rate of 500 rpm for 60 s to fully dissolve rebaudioside A, and then the solution was allowed to stand and the state of the solution was observed.
[0079] Table 3 Storage stability test results of high solubility stevioside solution
[0080]
[0081] It can be seen from Table 3 that the stevioside solution with a concentration lower than the saturation concentration prepared by the method of the present invention can maintain relatively good storage stability.
[0082] Embodiment 3:
[0083] Dilution stability experiment of high solubility stevioside solution:
[0084] To simulate the actual application scenario, samples 1, 2, 4, and 6 in Example 2 were diluted by different multiples, and the solution state of the dilution system was observed in a short time. 1 mL of the sample was added to 50, 100, and 200 mL of water, respectively, stirred to fully mix the two, and then left to stand and observed the solution state within 60 seconds.
[0085] Table 4 Dilution stability test results of high solubility stevioside solution
[0086]
[0087] From Table 4 and Figure 1 It can be seen that the stevioside solution with a concentration lower than the saturation concentration prepared by this method can maintain relatively good stability after being diluted to different multiples.
[0088] Embodiment 4:
[0089] Freeze-dried and reconstituted stability experiment of high-soluble stevioside solution:
[0090] Weigh some samples 2 to 6 in Example 2, freeze-dry them (-40°C, 24h) and observe the state of the freeze-dried samples. Use a scanning electron microscope to observe the surface morphology of the freeze-dried samples. Reconstitute the freeze-dried samples with equal concentrations, stir at 25°C at a stirring rate of 500 rpm for 180s to fully mix the freeze-dried samples with water, and then let them stand and observe their solution state within 60s.
[0091] Table 5 Freeze-dried and reconstituted stability test results of high solubility stevioside solution
[0092]
[0093]
[0094] From Table 5 and Figures 2 to 6 It can be seen that the freeze-dried sample of the stevioside solution with a concentration below saturation prepared by this method shows a structure that is conducive to sufficient contact with water or water penetration under SEM. Samples 2, 3, 4, 5, and 6 can remain clear and transparent in a short time after re-dissolution, showing relatively good re-dissolution stability.
Claims
1. A high-soluble steviol glycoside solution, characterized in that: It includes stevioside and an aqueous solution of a solubilizing substance; the mass molar concentration of the solubilizing substance in the aqueous solution of the solubilizing substance is greater than 0 to the solubility, the mass percentage concentration of stevioside in the high-solubility stevioside solution is from the solubility in pure water to the solubility in the aqueous solution of the solubilizing substance, and the solubilizing substance includes at least one of lactic acid, malic acid, citric acid, and tartaric acid.
2. The high-soluble steviol glycoside solution according to claim 1, characterized in that The solubilizing substance further comprises at least one of lactate, malate, citrate and tartrate, and the mass content of lactic acid, malic acid, citric acid and tartaric acid in the solubilizing substance is not less than 0.5%; The mass molar concentration of the solubilizing substance in the aqueous solution of the solubilizing substance is 1×10 -5 ~5×10 -2 mol / g; The mass percentage concentration of stevioside in the high-soluble stevioside solution is 0.10% to 15%.
3. The high-soluble steviol glycoside solution according to claim 1, characterized in that The steviol glycoside includes at least one of rebaudioside A, rebaudioside D, rebaudioside M, stevioside, rebaudioside B, rebaudioside C, rebaudioside E, rebaudioside F, rubusoside, dulcoside and steviolbioside.
4. The high-soluble steviol glycoside solution according to claim 3, characterized in that When the stevioside is rebaudioside A, the mass percentage concentration of rebaudioside A is 0.9% to 12%; When the stevioside is rebaudioside D, the mass percentage concentration of rebaudioside D is 0.12% to 0.31%; When the stevioside is rebaudioside M, the mass percentage concentration of rebaudioside M is 0.48% to 0.63%.
5. The method for preparing a high-soluble steviol glycoside solution according to any one of claims 1 to 4, characterized in that: The following steps are involved: The solubilizing substance is dissolved in water to obtain an aqueous solution of the solubilizing substance, and then a certain amount of stevioside is added to the aqueous solution of the solubilizing substance, and the mixture is stirred and mixed at 10° C. to 60° C., and allowed to stand to obtain a high-soluble stevioside solution.
6. The preparation method according to claim 5, characterized in that: The disturbance is a mechanical disturbance; the mechanical disturbance is one of electromagnetic stirring, vortex oscillation, shear homogenization, ultrasonic homogenization, and grinding homogenization.
7. Use of the highly soluble steviol glycoside solution according to any one of claims 1 to 4 or the highly soluble steviol glycoside solution obtained by the preparation method according to any one of claims 5 to 6 in the preparation of food or beverage products, characterized in that: The solution can be used directly or after dilution.
8. A high-solubility steviol glycoside complex, characterized in that: The high-soluble steviol glycoside solution according to any one of claims 1 to 4 or the high-soluble steviol glycoside solution obtained by the preparation method according to any one of claims 5 to 6 is obtained by freeze drying or spray drying.
9. The highly soluble steviol glycoside complex according to claim 8, characterized in that: The freeze-drying temperature is -30°C to -50°C, and the time is 12 to 36 hours.
10. Use of the highly soluble steviol glycoside complex according to any one of claims 8 to 9 in the preparation of food or beverage products.
Citation Information
Patent Citations
Method for preparing high-solubility stevioside compound
CN104530448A
Steviol glycoside solubilizer
CN111315233B
Method for enhancing rebaudioside D solubility in water
CN105995373A
Steviol glycoside solubility enhancers
CN111315233A
Readily dissolvable steviol glycoside compositions
CN111315234A