Highly soluble steviol glycoside solution, method of making and use thereof

Abstract

The application discloses a high-solubility steviol glycoside solution and a preparation method and application thereof. The high-solubility steviol glycoside solution comprises steviol glycoside and a water-soluble solubilizing substance solution; the mass molar concentration of the solubilizing substance in the water-soluble solubilizing substance solution is greater than 0 to solubility; the mass percentage concentration of the steviol glycoside in the high-solubility steviol glycoside solution is solubility in pure water to solubility in the water-soluble solubilizing substance solution; and the solubilizing substance comprises at least one of lactic acid, malic acid, citric acid and tartaric acid. The steviol glycoside is added into the water-soluble solubilizing substance solution, and after simple mixing and dissolving, the corresponding high-solubility steviol glycoside solution can be obtained. The steviol glycoside complex has the advantages of high solubility, high stability, low cost, simple preparation process and the like, is easy to produce on a large scale, and is suitable for liquid concentrate systems such as table sweeteners or beverage syrups.

Description

Technical Field

[0001] This invention relates to the field of food additives, specifically to a highly soluble steviol glycoside solution, its preparation method, and its application. Background Technology

[0002] Low-sugar and reduced-sugar 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.

[0003] Steviosides, as the world's third-generation sugar source, are natural non-nutritive sweeteners characterized by high sweetness (250-450 times that of sucrose) and low calorie value (1 / 300 that of sucrose). They also possess effects such as lowering blood pressure, lowering blood sugar, preventing tooth decay, and anti-tumor properties, and have been widely used in food and beverages. From a molecular structural perspective, steviol glycosides are enantio-kaurene diterpenoid glycosides, composed of a hydrophobic steviol backbone and hydrophilic sugar groups. Currently known sweet components include steviol glycosides, rebaudioside A (RA, Formula 1), rebaudioside B, rebaudioside C, rebaudioside D (RD, Formula 2), rebaudioside E, rebaudioside F, rebaudioside M (RM, Formula 3), stevia glycosides, durcuryl glycosides, and steviol disaccharides. The differences in their molecular structures lie in the number and distribution of hydrophilic sugar groups, which further leads to differences in their taste and physicochemical properties.

[0004]

[0005] Formula 1. Molecular structural formula of Rebaudioside A

[0006]

[0007] Formula 2. Molecular structural formula of Rebaudioside D

[0008]

[0009] Formula 3. Molecular structural formula of Rebaudioside M

[0010] The application of high-purity steviol glycosides in food and beverages is challenging because of their poor solubility in water. For example, the solubility of riboside A is about 0.8%, riboside B is 0.01% to 0.02%, riboside D is about 0.04%, and riboside M is about 0.1%. This greatly limits their application in liquid formulations, especially in liquid concentration systems such as beverage syrups, flavor concentrates, and tabletop sweeteners.

[0011] To improve the solubility of steviol glycosides in water, existing methods are as follows:

[0012] 1) Chinese invention patent application (publication number CN104530448A) discloses a method for preparing a highly soluble steviol glycoside complex. This method uses hydroxypropyl-β-cyclodextrin to coat steviol glycosides to obtain a highly soluble steviol glycoside complex. However, this method uses solvents such as methanol, ethanol, and isopropanol, which require further removal of non-edible substances, and its safety still needs to be evaluated.

[0013] 2) Chinese invention patent application (publication number CN111315233B) discloses a steviol glycoside solubilizer. The system uses gallic acid, mandelic acid, and pyromellitic acid as the main components, and adds corn starch fiber or gellan gum to form a steviol glycoside solubilizer. However, the solubilizing 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 steviol glycoside solution with high solubility, high stability, low cost and simple preparation process. Summary of the Invention

[0015] In view of the shortcomings of the existing technology, the purpose of this invention is to provide a highly soluble steviol glycoside solution, its preparation method and application.

[0016] The technical solution adopted in this invention is:

[0017] A highly soluble steviol glycoside solution includes steviol glycoside and an aqueous solution of a solubilizing agent; the molality of the solubilizing agent in the aqueous solution is greater than 0 to the solubility (saturation concentration); the mass percentage concentration of steviol glycoside in the highly soluble steviol glycoside solution is from the solubility in pure water to the solubility in the aqueous solution of the solubilizing agent; the solubilizing agent includes at least one of lactic acid, malic acid, citric acid, and tartaric acid.

[0018] The highly soluble steviol glycoside solution of the present invention has good fluidity and a clear, 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 includes at least one of lactate, malate, citrate, and tartrate;

[0028] More 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 molality of the solubilizing substance in the aqueous solution is 1 × 10⁻⁶. -5 ~5×10 - 2 mol / g;

[0030] More preferably, the molality of the solubilizing substance in the aqueous solution is 2.5 × 10⁻⁶. -3 ~1.5×10 -2 mol / g.

[0031] Preferably, the mass percentage concentration of steviol glycosides in the highly soluble steviol glycoside solution is 0.10% to 15%.

[0032] More preferably, the mass percentage concentration of steviol glycosides in the highly soluble steviol glycoside solution is 0.10% to 10%.

[0033] Preferably, the steviol glycosides include at least one of ribobadiol A, ribobadiol D, ribobadiol M, steviol glycoside, ribobadiol B, ribobadiol C, ribobadiol E, ribobadiol F, stevioside, dulcitol, and steviol disaccharide.

[0034] More preferably, the steviol glycosides include at least one of ribobadiol A, ribobadiol D, and ribobadiol M.

[0035] More preferably, when the steviol glycoside is ribobadiol A, the mass percentage concentration of ribobadiol A is 0.9% to 12%;

[0036] More preferably, when the steviol glycoside is ribobadiol D, the mass percentage concentration of ribobadiol D is 0.12% to 0.31%;

[0037] More preferably, when the steviol glycoside is ribobadiol M, the mass percentage concentration of ribobadiol M is 0.48% to 0.63%.

[0038] The above-mentioned method for preparing highly soluble steviol glycoside solution includes the following steps:

[0039] The solubilizing agent is dissolved in water to obtain an aqueous solution of the solubilizing agent. Then, a certain amount of steviol glycosides is added to the aqueous solution of the solubilizing agent, and the mixture is stirred and mixed at 10℃~60℃. After standing, a highly soluble steviol glycoside solution is obtained.

[0040] Preferably, the time for the disturbance mixing is 30s to 300s.

[0041] Preferably, the disturbance is a mechanical disturbance;

[0042] More preferably, the mechanical disturbance is one of electromagnetic stirring, vortex oscillation, shear homogenization, ultrasonic homogenization, and grinding homogenization.

[0043] Preferably, the settling time is 12 to 36 hours.

[0044] The application of the above-described highly soluble steviol glycoside solution or the highly soluble steviol glycoside solution obtained by the above preparation method in the preparation of food or beverage products, wherein the solution is used directly or after dilution. The highly soluble steviol glycoside 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 highly soluble steviol glycoside complex is obtained by freeze-drying or spray-drying a highly soluble steviol glycoside solution obtained by the above-described preparation method. The resulting highly soluble steviol glycoside complex is a steviol glycoside product in solid powder form.

[0046] Preferably, the freeze-drying temperature is -30℃ to -50℃, and the time is 12 to 36 hours.

[0047] The application of the above-mentioned highly soluble steviol glycoside complex in the preparation of food or beverage products. The highly soluble steviol glycoside complex of the present invention can be used directly or after dissolution.

[0048] The highly soluble steviol glycoside complex solid powder of the present invention exhibits a surface morphology under a scanning electron microscope that facilitates full contact or water penetration, and has good resolution stability.

[0049] The beneficial effects of the present invention are as follows: The steviol glycoside complex of the present invention has the advantages of high content, high stability, low cost and simple preparation process, 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 the solubilization effect is obvious.

[0052] 2) The steviol glycoside solution of the present invention remains relatively clear, transparent and homogeneous after being placed at room temperature for 30 days, without the formation of obvious flocculent matter or precipitation, and has good storage stability; it remains clear, transparent and homogeneous after being diluted according to actual application scenarios, and has good dilution stability; the solution remains clear, transparent and homogeneous after being reconstituted from lyophilized samples, and has good lyophilized reconstitution stability.

[0053] 3) The method for preparing the steviol glycoside solution of the present invention is simpler and milder than existing solubilization methods (e.g., no heating step is required), which greatly reduces production costs and is suitable for large-scale production applications. Attached Figure Description

[0054] Figure 1 The images show the appearance of solution samples 1, 2, 4, and 6 in Example 3 before dilution.

[0055] Figure 2 The image shows the appearance of freeze-dried sample 2 in Example 4 and its SEM image.

[0056] Figure 3 The image shows the appearance of freeze-dried sample 3 in Example 4 and its SEM image.

[0057] Figure 4 The image shows the appearance of freeze-dried sample 4 in Example 4 and its SEM image.

[0058] Figure 5 The image shows the appearance of freeze-dried sample 5 from Example 4 and its SEM image.

[0059] Figure 6 The image shows the appearance of freeze-dried sample 6 in Example 4 and its SEM image. Detailed Implementation

[0060] The present invention will now be described in detail with reference to embodiments. The purpose of this description is only to better illustrate the content of the present invention, but it does not limit the present invention in any way.

[0061] Example 1:

[0062] Experiments on the solubilizing effects of different solubilizing substances on steviol glycosides:

[0063] According to Table 1, different solubilizing substances were weighed and dissolved in water to prepare aqueous solutions of a certain concentration. Excess steviol glycosides were added directly to the solutions, and the mixture was vortexed at 1000 rpm for 180 s at 25°C to ensure thorough mixing. After standing for 24 hours, the solution was centrifuged, and the supernatant was collected. The solubility of steviol glycosides was determined by HPLC (refer to GB 1886.355). The experimental results of the solubilizing effect of different solubilizing substances on steviol glycosides (National Food Safety Standard for Food Additives, 2022) are shown in Table 1 below:

[0064] Table 1. Experimental results of the solubilizing effect of different solubilizing substances on steviol glycosides.

[0065]

[0066] As shown in Table 1:

[0067] 1) The different solubilizing substances mentioned above all have significant solubilizing effects on different types of steviol glycosides;

[0068] 2) The solubility of steviol glycosides increases with the increase of the content of solubilizing substances;

[0069] 3) The same solubilizing substance has different solubilizing effects on different types of steviol glycosides, which may be attributed to the differences in molecular structure of different types of steviol glycosides.

[0070] Comparative Example 1:

[0071] Weigh out different other substances according to Table 2 and prepare aqueous solutions of a certain concentration in water. Add excess steviol glycosides directly to the solution and vortex at 1000 rpm for 180 s at 25°C to ensure thorough mixing. After the solution has stood for 24 h, centrifuge and collect the supernatant. Determine the solubility of steviol glycosides by HPLC (refer to GB 1886.355). The following table shows the experimental results of the solubilizing effect of different other substances on steviol glycosides (as per the 2022 National Food Safety Standard for Food Additives).

[0072] Table 2. Experimental results of the solubilizing effect of different other substances on steviol glycosides.

[0073]

[0074] As shown in Table 2, although the other substances mentioned above have similar structures or properties to the solubilizing substances of this invention, their solubilizing effect on steviol glycosides at the same concentration is minimal, and they may even reduce the solubility of steviol glycosides. Furthermore, the concentration of some other substances is limited due to their own low solubility; for example, alanine, succinic acid, and aspartic acid have inherent solubility limitations. Therefore, steviol glycoside solubilizing substances need to have specific structures and properties.

[0075] Example 2:

[0076] Storage stability test of highly soluble steviol glycoside solution:

[0077] Weigh different solubilizing substances according to Table 3 and prepare aqueous solutions of solubilizing substances of a certain concentration in water. Add an appropriate amount of ribobadiol A to the solution and stir at 500 rpm for 60 seconds at 25°C to fully dissolve ribobadiol A. Then let the solution stand and observe the state of the solution.

[0078] Table 3. Results of storage stability test of highly soluble steviol glycoside solution

[0079]

[0080] As shown in Table 3, the steviol glycoside solution with a concentration below saturation prepared using the method of the present invention can maintain relatively good storage stability.

[0081] Example 3:

[0082] Dilution stability test of highly soluble steviol glycoside solution:

[0083] To simulate real-world application scenarios, samples 1, 2, 4, and 6 from Example 2 were diluted by different factors, and the solution state of the diluted system was observed over a short period of time. 1 mL of sample was added to 50, 100, and 200 mL of water, respectively, stirred to ensure thorough mixing, and allowed to stand for 60 seconds to observe the solution state.

[0084] Table 4. Results of dilution stability test of highly soluble steviol glycoside solutions

[0085]

[0086] From Table 4 and Figure 1 It can be seen that the steviol glycoside solution with a concentration below saturation prepared by this method can maintain good stability after being diluted by different factors.

[0087] Example 4:

[0088] Lyophilized-reconstituted stability test of highly soluble steviol glycoside solutions:

[0089] Samples 2-6 from Example 2 were weighed and freeze-dried (-40℃, 24h), and the state of the freeze-dried samples was observed. The surface morphology of the freeze-dried samples was observed using a scanning electron microscope. The freeze-dried samples were reconstituted at the same concentration, and stirred at 500 rpm for 180s at 25℃ to ensure that the freeze-dried samples and water were fully mixed. The mixture was then allowed to stand, and the solution state was observed within 60s.

[0090] Table 5 Results of freeze-drying and reconstitution stability tests of highly soluble steviol glycoside solutions

[0091]

[0092] From Table 5 and Figures 2-6It can be seen that the lyophilized samples of steviol glycoside solutions with subsaturated concentrations prepared using this method exhibit structures that facilitate sufficient contact or water penetration under SEM. Samples 2, 3, 4, 5, and 6 all maintained a clear and transparent state for a short time after reconstitution, demonstrating good reconstitution stability.

Claims

1. A highly soluble steviol glycoside solution, characterized in that, The solution comprises steviol glycosides and an aqueous solution of a solubilizing agent; the solubilizing agent is composed of at least one of lactic acid, malic acid, citric acid, and tartaric acid, and the mass content of lactic acid, malic acid, citric acid, and tartaric acid in the solubilizing agent is not less than 0.5%; the molality of the solubilizing agent in the aqueous solution is 1 × 10⁻⁶. -5 ~5×10 -2 The mol / g concentration of steviol glycosides in the highly soluble steviol glycoside solution is 0.10% to 15% by mass, and the solution remains clear, transparent, and homogeneous after being stored at room temperature for 30 days. The steviol glycosides include at least one of ribobadiol A, ribobadiol D, and ribobadiol M.

2. The highly soluble steviol glycoside solution according to claim 1, characterized in that, When the steviol glycoside is ribobadiol A, the mass percentage concentration of ribobadiol A is 0.9% to 12%; when the steviol glycoside is ribobadiol D, the mass percentage concentration of ribobadiol D is 0.12% to 0.31%; when the steviol glycoside is ribobadiol M, the mass percentage concentration of ribobadiol M is 0.48% to 0.63%.

3. A method for preparing a highly soluble steviol glycoside solution according to claim 1 or 2, characterized in that, Includes the following steps: The solubilizing agent is dissolved in water to obtain an aqueous solution of the solubilizing agent. Then, steviol glycosides are added to the aqueous solution of the solubilizing agent, and the mixture is stirred and mixed at 10℃~60℃. After standing, a highly soluble steviol glycoside solution is obtained.

4. The preparation method according to claim 3, characterized in that, The time for the disturbance mixing is 30s to 300s.

5. The preparation method according to claim 4, 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.

6. The application of the highly soluble steviol glycoside solution according to claim 1 or 2, or the highly soluble steviol glycoside solution obtained by the preparation method according to any one of claims 3 to 5, in the preparation of food, characterized in that, The solution can be used directly or after dilution.

7. A highly soluble steviol glycoside complex, characterized in that, The highly soluble steviol glycoside solution obtained by the preparation method according to any one of claims 1 or 2 or claims 3 to 5 is obtained by freeze drying or spray drying.

8. The highly soluble steviol glycoside complex according to claim 7, characterized in that, The freeze-drying temperature is -30℃ to -50℃, and the time is 12 to 36 hours.

9. The use of the highly soluble steviol glycoside complex according to claim 7 or 8 in the preparation of food.

Images