New use and method of preparation of sodium hyaluronate and condiments

Abstract

The application belongs to the field of new materials, and discloses a use of glutamic acid sodium hyaluronate in preparation of a condiment, wherein the glutamic acid sodium hyaluronate is sodium hyaluronate connected with L-sodium glutamate or L-glutamic acid through a chemical bond. The glutamic acid sodium hyaluronate of the application is not easy to form pyroglutamic acid sodium at high temperature, and can improve the stability of sodium glutamate, so that the use of the glutamic acid sodium hyaluronate in preparation of the condiment can be suitable for a high-temperature cooking environment, and the glutamic acid sodium hyaluronate can be used as a seasoning to replace glutamic acid / sodium. Meanwhile, the application further provides a preparation method of the glutamic acid sodium hyaluronate and the condiment.

Description

Technical Field

[0001] This invention relates to the field of new materials, specifically to new uses and preparation methods of sodium glutamate hyaluronic acid, as well as to seasonings. Background Technology

[0002] Glutamic acid-grafted sodium hyaluronate is widely used in cosmetics and pharmaceuticals.

[0003] For example, CN116769066A proposes the use of glutamic acid-grafted sodium hyaluronate in the prevention and / or relief of skin discomfort caused by inflammation.

[0004] CN112194738A proposes the use of glutamic acid-grafted sodium hyaluronate as an immune enhancer.

[0005] The technical problem this solution aims to address is: how to develop new applications for glutamic acid-grafted sodium hyaluronate. Summary of the Invention

[0006] The purpose of this invention is to provide a new use for preparing seasonings with sodium glutamate hyaluronic acid. We have found that sodium glutamate hyaluronic acid does not easily form sodium pyroglutamate at high temperatures, which can improve the stability of sodium glutamate. Therefore, seasonings prepared with sodium glutamate hyaluronic acid are suitable for high-temperature cooking environments and can be used as a substitute for glutamate / sodium.

[0007] In addition, the present invention also provides a method for preparing sodium glutamate hyaluronic acid and a seasoning.

[0008] To achieve the above objectives, the present invention provides the following technical solution: the use of sodium glutamate hyaluronic acid in the preparation of seasonings, wherein the sodium glutamate hyaluronic acid is sodium hyaluronic acid with L-sodium glutamate or L-glutamic acid linked by chemical bonds.

[0009] Preferably, the sodium glutamate hyaluronic acid is sodium hyaluronic acid with L-sodium glutamate or L-glutamic acid linked by ionic bonds; more specifically, the chemical bond is an ionic bond formed by the carboxyl group in the sodium glutamate hyaluronic acid molecule and the ammonium group in the L-sodium glutamate molecule or L-glutamic acid molecule.

[0010] The structural formula of the sodium glutamate hyaluronic acid of the present invention is as follows:

[0011]

[0012] Where M is either Na or H.

[0013] The sodium glutamate hyaluronic acid contains x D-glucuronide sodium-N-acetylglucosamine disaccharide units and y L-glutamate / sodium D-glucuronide-N-acetylglucosamine disaccharide units. Simultaneously, y ≥ 1, meaning that each hyaluronic acid molecule of the sodium glutamate hyaluronic acid should have at least one carboxyl group bound to glutamate / sodium.

[0014] x corresponds to the number of D-glucuronide sodium-N-acetylglucosamine disaccharide units in hyaluronic acid with a molecular weight of 1000 Da to 2000 kDa.

[0015] Generally, x can be chosen to be between 3 and 6000;

[0016] In this invention, ionic bonds are preferred for connection. The connecting force of ionic bonds is far less than that of covalent bonds. Ionic bonds can slowly release glutamic acid and its salts during the flavoring process. At the same time, at high temperatures, based on the protection of hyaluronic acid macromolecules and the insolubility of ionic compounds in oil, the complete or rapid release of glutamic acid and its salts to form sodium pyroglutamate is avoided.

[0017] Another advantage of using ionic bonds is that:

[0018] The long-chain structure of sodium hyaluronate can bind a large amount of monosodium glutamate (MSG), increasing the number of MSGs that bind to glutamate receptors at the same MSG concentration, thus enhancing the umami flavor of MSG.

[0019] Sodium hyaluronate provides ample sodium ions to monosodium glutamate (MSG), preventing sodium ion loss into food and resulting in flavor degradation that can occur with MSG alone. Sodium hyaluronate also provides an appropriate pH buffer and a large amount of sodium ions to MSG, maintaining the sodium ion count at an optimal level and enhancing the umami flavor of MSG.

[0020] In the above-mentioned applications, each sodium glutamate hyaluronic acid molecule is grafted with at least one sodium L-glutamate molecule or an L-glutamate molecule.

[0021] In the above-mentioned applications, the weight-average molecular weight of sodium hyaluronate in the sodium glutamate hyaluronate is 1 kDa to 2000 kDa, preferably 300 kDa to 1200 kDa.

[0022] In some preferred embodiments of the present invention, the weight-average molecular weight of sodium hyaluronate is 1 kDa, 2 kDa, 5 kDa, 10 kDa, 20 kDa, 50 kDa, 100 kDa, 200 kDa, 500 kDa, 1000 kDa, 1500 kDa or 2000 kDa.

[0023] In the above-mentioned applications, the sodium hyaluronate containing glutamic acid is a sodium hyaluronate with a fully distributed molecular weight; the weight-average molecular weight of the fully distributed sodium hyaluronate is 2 kDa to 1500 kDa. Within this molecular weight range, x can be selected from 6 to 4500; preferably, the weight-average molecular weight of the fully distributed sodium hyaluronate is 300 kDa to 1500 kDa.

[0024] In some preferred embodiments of the present invention, the weight-average molecular weight of sodium hyaluronate with full molecular weight distribution is 2kDa, 5kDa, 10kDa, 20kDa, 50kDa, 100kDa, 200kDa, 500kDa, 1000kDa, 1200kDa or 1500kDa.

[0025] Sodium hyaluronate with different weight-average molecular weights and full molecular weight distributions can be prepared using the process described in the applicant's earlier application CN113512134B.

[0026] In the above-mentioned applications, the sodium hyaluronate with full molecular weight distribution is sodium hyaluronate HA60 with full molecular weight distribution.

[0027] Compared to sodium hyaluronate with a single molecular weight, the advantages of using sodium hyaluronate with a full molecular weight distribution are: a richer flavor profile; and the use of sodium hyaluronate with different molecular weights allows for a lower degradation rate of monosodium glutamate (MSG) at high temperatures and a higher sustained-release concentration of MSG. This is likely because the weight-average molecular weight distribution of full molecular weight sodium hyaluronate ranges from 2kDa to 1500kDa, inevitably leading to different glutamate / sodium grafting densities on different molecular weights, thus resulting in a richer flavor profile.

[0028] In the above-mentioned uses, 1% to 100% of the carboxyl groups of the sodium hyaluronate in the sodium glutamate are bound to sodium L-glutamate or L-glutamic acid, preferably 20% to 80% of the carboxyl groups are bound to sodium L-glutamate or L-glutamic acid, and more preferably 40% to 60% of the carboxyl groups are bound to sodium L-glutamate or L-glutamic acid.

[0029] Meanwhile, the present invention also discloses a seasoning containing sodium glutamate hyaluronic acid for any of the uses described above.

[0030] The above-mentioned seasonings contain 0.0001 wt% to 99.9999 wt% sodium glutamate hyaluronic acid.

[0031] Among the aforementioned seasonings, the seasonings are monosodium glutamate, soy sauce, soy sauce, vinegar, or hot pot base.

[0032] Finally, the present invention also discloses a method for preparing sodium glutamate hyaluronic acid for any of the above-described uses, comprising the following steps:

[0033] (1) Preparation of solution 1: Dissolve sodium hyaluronate to obtain solution.

[0034] (2) Preparation of solution 2: Dissolve L-glutamate sodium or L-glutamate and add hydrochloric acid to form glutamate hydrochloride solution;

[0035] (3) Preparation of sodium glutamate hyaluronic acid: Add solution 2 to solution 1 according to the required binding ratio of glutamate on sodium hyaluronic acid, stir and react. After the reaction is completed, remove the unreacted glutamate and the sodium chloride produced by the reaction to obtain the sodium glutamate hyaluronic acid.

[0036] In some embodiments of the present invention, 1g of sodium hyaluronate can react with at least 0.01g of sodium L-glutamate or L-glutamic acid; more preferably, 1g of sodium hyaluronate can react with 0.1 to 0.5g of sodium L-glutamate or L-glutamic acid; more preferably, 1g of sodium hyaluronate can react with 0.12 to 0.45g of sodium L-glutamate or L-glutamic acid.

[0037] As can be seen from the above preparation method, the present invention can prepare products based on ionic bonding using a relatively simple blending process. Compared with the method described in CN116769066A, which requires the use of catalysts and activators to promote the formation of covalent bonds, it can be further confirmed that the compounds of the present invention are formed based on ionic bonding.

[0038] Compared with the prior art, the beneficial effects of the present invention are:

[0039] (1). Experiments have shown that sodium glutamate forms a stable sodium glutamate salt. The amino group of sodium glutamate forms a salt with the carboxyl group of hyaluronic acid. It is not easy to form sodium pyroglutamate at high temperature, which can improve the stability of sodium glutamate.

[0040] (2) Experiments have shown that using sodium hyaluronate can enhance the flavor of dishes and enrich their flavor profile. This is because sodium glutamate stimulates specific taste receptors on the tongue, such as amino acid receptors T1R1 / T1R3 and metabolic glutamate receptors (mGluR4 and mGluR1), to produce taste sensations. The long-chain structure of sodium hyaluronate can bind a large amount of sodium glutamate, increasing the number of sodium glutamate receptors bound to them at the same sodium glutamate concentration, thus enhancing the umami flavor of sodium glutamate.

[0041] Meanwhile, the umami flavor of monosodium glutamate (MSG) is inextricably linked to its sodium ion content. MSG containing only one sodium ion has umami flavor, while glutamic acid without sodium ions and disodium glutamate formed under alkaline conditions do not. Therefore, in daily cooking, MSG may interact with certain foods and lose its umami flavor. Sodium hyaluronate contains a large number of carboxyl groups that form salts with sodium ions. Therefore, when sodium hyaluronate combines with MSG, it provides an appropriate pH buffer and a large number of sodium ions, maintaining the sodium ion count in MSG at an optimal level and enhancing its umami flavor.

[0042] (3). Sodium glutamate prepared from full molecular weight sodium hyaluronate and non-full molecular weight sodium hyaluronate can both improve the stability of glutamate / sodium at high temperature.

[0043] (4) Compared to sodium glutamate prepared from sodium hyaluronate with a non-full molecular weight, sodium glutamate prepared from sodium hyaluronate with a full molecular weight has a richer flavor when used in dishes. In particular, a sodium hyaluronate with a full molecular weight distribution, as described in patent CN113512134B, has no flavor on its own, but enhances the umami flavor of monosodium glutamate when used with it. The possible reason is that since the weight-average molecular weight distribution of sodium hyaluronate with a full molecular weight ranges from 2kDa to 1500kDa, the glutamate / sodium grafting density on sodium hyaluronate with different molecular weights will inevitably be different, resulting in a richer flavor profile. Attached Figure Description

[0044] Figure 1 The present invention relates to sodium glutamate hyaluronic acid, sodium hyaluronate, and monosodium glutamate. 1 H NMR spectrum. Detailed Implementation

[0045] The technical solutions of the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of the present invention.

[0046] Example 1

[0047] (1) Preparation of solution 1: Weigh 1g of sodium hyaluronate HA60 with full molecular weight distribution (provided by Shandong Guantianxia Biotechnology Co., Ltd., product patent: CN113512134A A sodium hyaluronate with full molecular weight distribution and its preparation method and application, weight average molecular weight 600kDa), dissolve it in 100mL of water to obtain a solution with a hyaluronic acid concentration of 1% (w / v).

[0048] (2) Preparation of solution 2: Weigh 0.45g of sodium glutamate and dissolve it in 10mL of water. Add 2mL of 1mol / L HCl solution to form glutamate hydrochloride solution.

[0049] (3) Preparation of sodium glutamate hyaluronic acid: Add solution 2 to solution 1 and stir thoroughly for 30 minutes to ensure complete reaction.

[0050] (4) Dialysis removes unreacted glutamic acid and sodium chloride produced by the reaction, ethanol precipitation, and drying to obtain the glutamic acid sodium hyaluronate raw material. The proportion of sodium glutamate bound to sodium hyaluronate in the glutamic acid sodium hyaluronate can reach 80%.

[0051] (5) The obtained sodium hyaluronate, HA60, and monosodium glutamate were subjected to... 1 H NMR results are attached. Figure 1 .

[0052] Example 2

[0053] (1) Preparation of solution 1: Weigh 1g of sodium hyaluronate HA60 with full molecular weight distribution (same as in Example 1), dissolve it in 100mL of water to obtain a solution with a hyaluronic acid concentration of 1% (w / v).

[0054] (2) Preparation of solution 2: Weigh 0.34g of sodium glutamate and dissolve it in 10mL of water. Add 0.75mL of 1mol / L HCl solution to form glutamate hydrochloride solution.

[0055] (3) Preparation of sodium glutamate hyaluronic acid: Add solution 2 to solution 1 and stir thoroughly for 30 minutes to ensure complete reaction.

[0056] (4) Dialysis removes unreacted glutamic acid and sodium chloride produced by the reaction, ethanol precipitation, and drying to obtain the glutamic acid sodium hyaluronate raw material. The proportion of sodium glutamate bound to sodium hyaluronate in the glutamic acid sodium hyaluronate can reach 60%.

[0057] Example 3

[0058] (1) Preparation of solution 1: Weigh 1g of sodium hyaluronate HA60 with full molecular weight distribution (same as in Example 1), dissolve it in 100mL of water to obtain a solution with a hyaluronic acid concentration of 1% (w / v).

[0059] (2) Preparation of solution 2: Weigh 0.23g of sodium glutamate and dissolve it in 10mL of water. Add 1mL of 1mol / L HCl solution to form a glutamate hydrochloride solution.

[0060] (3) Preparation of sodium glutamate hyaluronic acid: Add solution 2 to solution 1 and stir thoroughly for 30 minutes to ensure complete reaction.

[0061] (4) Dialysis removes unreacted glutamic acid and sodium chloride produced by the reaction, ethanol precipitation, and drying to obtain the glutamic acid sodium hyaluronate raw material. The proportion of sodium glutamate bound to sodium hyaluronate in the glutamic acid sodium hyaluronate can reach 40%.

[0062] Example 4

[0063] (1) Preparation of solution 1: Weigh 1g of sodium hyaluronate HA60 with full molecular weight distribution (same as in Example 1), dissolve it in 100mL of water to obtain a solution with a hyaluronic acid concentration of 1% (w / v).

[0064] (2) Preparation of solution 2: Weigh 0.12g of sodium glutamate and dissolve it in 10mL of water. Add 0.5mL of 1mol / L HCl solution to form glutamate hydrochloride solution.

[0065] (3) Preparation of sodium glutamate hyaluronic acid: Add solution 2 to solution 1 and stir thoroughly for 30 minutes to ensure complete reaction.

[0066] (4) Dialysis removes unreacted glutamic acid and sodium chloride produced by the reaction, ethanol precipitation, and drying to obtain the glutamic acid sodium hyaluronate raw material. The proportion of sodium glutamate bound to sodium hyaluronate in the glutamic acid sodium hyaluronate can reach 20%.

[0067] Example 5

[0068] Sodium glutamate hyaluronic acid was prepared according to the steps described in Example 2, except that the sodium hyaluronic acid with a full molecular weight distribution had a weight average molecular weight of 300 kDa.

[0069] Example 6

[0070] Sodium glutamate hyaluronic acid was prepared according to the steps described in Example 2, except that the weight-average molecular weight of the sodium hyaluronic acid with full molecular weight distribution used was 1200 kDa.

[0071] Example 7

[0072] Sodium glutamate hyaluronic acid was prepared according to the steps described in Example 2, except that the weight-average molecular weight of the sodium hyaluronic acid with full molecular weight distribution used was 1500 kDa.

[0073] Example 8

[0074] Sodium glutamate hyaluronic acid was prepared according to the steps described in Example 2, except that the sodium hyaluronic acid used was a common commercially available sodium hyaluronic acid with a weight average molecular weight of 300 kDa, which is not a sodium hyaluronic acid with a full molecular weight distribution.

[0075] Example 9

[0076] Sodium glutamate hyaluronic acid was prepared according to the steps described in Example 2, except that the sodium hyaluronic acid used was a common commercially available sodium hyaluronic acid with a weight average molecular weight of 600 kDa, which is not a sodium hyaluronic acid with a full molecular weight distribution.

[0077] Example 10

[0078] Sodium glutamate hyaluronic acid was prepared according to the steps described in Example 2, except that the sodium hyaluronic acid used was a common commercially available sodium hyaluronic acid with a weight average molecular weight of 1200 kDa, and not a sodium hyaluronic acid with a full molecular weight distribution.

[0079] Performance Test Item 1

[0080] This project is used to verify that the sodium glutamate hyaluronic acid prepared according to the present invention can improve the thermal stability of sodium glutamate.

[0081] Preparation of solution A: Take 40 mg of sodium glutamate hyaluronic acid prepared according to the method of Example 1, dissolve it in 100 mL of water to prepare a sodium glutamate hyaluronic acid solution of 400 μg / mL. Based on the calculation that the proportion of sodium glutamate bound to the carboxyl group of sodium glutamate in sodium glutamate hyaluronic acid is 80%, the amount of sodium glutamate in the solution is about 100 μg / mL.

[0082] Preparation of solution B: Dissolve 10 mg of sodium glutamate in 100 mL of water to prepare a sodium glutamate solution with a concentration of 100 μg / mL.

[0083] Preparation of solution C: Take 40 mg of sodium glutamate hyaluronic acid prepared according to the method of Example 9, dissolve it in 100 mL of water to prepare a sodium glutamate hyaluronic acid solution of 400 μg / mL. Based on the calculation that the proportion of sodium glutamate bound to the carboxyl group of sodium glutamate in sodium glutamate hyaluronic acid is 80%, the amount of sodium glutamate in the solution is about 100 μg / mL.

[0084] Preparation of solution D: Prepare a mixed aqueous solution of sodium hyaluronate HA60 (same as sodium hyaluronate in Example 1) with a concentration of 300 μg / mL and sodium glutamate with a concentration of 100 μg / mL;

[0085] Plotting the standard curve: Prepare solutions of sodium glutamate at concentrations of 60, 80, 100, 120, and 140 μg / mL. Take 5 mL of each concentration standard solution, add 1 mL of ninhydrin solution, and incubate in a 90℃ water bath for 25 min for color development.

[0086] Table 1. OD569 of Glutamic Acid Standard Solution

[0087]

[0088] The standard curve is calculated to be OD569 = 0.0279c - 2.0474, where OD569 is the optical density of the sample at 569 nm as measured by the microplate reader, c is the glutamate concentration, and R0 is the optical density of the sample. 2 =0.999.

[0089] Thermal stability evaluation: Take 5 mL each of solutions A, B, C, and D above, and incubate in an oil bath at 120℃ for 30 minutes. Separately, take 5 mL each of solutions A, B, C, and D as blank controls, add 1 mL of ninhydrin solution to each, and incubate in a water bath at 90℃ for 25 minutes for color development. Calculate the glutamic acid concentration based on the standard curve, and then convert this to the proportion of glutamic acid degradation or pyroglutamic acid formation. The experiment was repeated three times, and the average value was taken. The results are shown in Table 2.

[0090] Table 2. Sodium glutamate and hyaluronic acid improve the stability of monosodium glutamate.

[0091]

[0092]

[0093] It can be seen that, compared with free monosodium glutamate, the sodium glutamate hyaluronic acid prepared by this invention can improve the stability of monosodium glutamate and prevent monosodium glutamate from degrading or generating pyroglutamic acid at high temperatures.

[0094] Example 11

[0095] Take a sodium glutamate hyaluronic acid raw material prepared according to the method of Example 2, and take an appropriate amount of soybean oil, monosodium glutamate, edible salt, chili, scallion, ginger, garlic, white sugar, Sichuan pepper, and chili. Mix them thoroughly. The sodium glutamate hyaluronic acid raw material accounts for 5% (w / w) in the mixture to obtain a hot pot base raw material containing sodium glutamate hyaluronic acid, which can be used for the production of hot pot base.

[0096] Example 12

[0097] Take a sodium glutamate hyaluronic acid obtained according to the method of Example 3, and take a conventional commercially available soy sauce. Add the sodium glutamate hyaluronic acid to the soy sauce at a ratio of 1% (w / v) to obtain soy sauce with added sodium glutamate hyaluronic acid.

[0098] Example 13

[0099] Take 100g of seafood soup with umami characteristics and add 20mg of sodium glutamate hyaluronic acid seasoning prepared in Example 2.

[0100] Example 14

[0101] Take 100g of pickled fish, a dish with a sour taste, and add 20mg of sodium glutamate hyaluronic acid seasoning prepared in Example 2.

[0102] Example 15

[0103] Take 100g of eggplant with a sweet flavor and add 20mg of sodium glutamate hyaluronic acid seasoning prepared in Example 2.

[0104] Example 16

[0105] Take 100g of pickled cucumber, a dish with a salty flavor, and add 20mg of sodium glutamate hyaluronic acid seasoning prepared in Example 2.

[0106] Example 17

[0107] Take 100g of seafood soup with umami characteristics and add 20mg of sodium glutamate hyaluronic acid seasoning prepared in Example 5.

[0108] Example 18

[0109] Take 100g of seafood soup with umami characteristics and add 20mg of sodium glutamate hyaluronic acid seasoning prepared in Example 6.

[0110] Example 19

[0111] Take 100g of seafood soup with umami characteristics and add 20mg of sodium glutamate hyaluronic acid seasoning prepared in Example 7.

[0112] Example 20

[0113] Take 100g of seafood soup with umami characteristics and add 20mg of sodium glutamate hyaluronic acid seasoning prepared in Example 8.

[0114] Example 21

[0115] Take 100g of seafood soup with umami characteristics and add 20mg of sodium glutamate hyaluronic acid seasoning prepared in Example 9.

[0116] Example 22

[0117] Take 100g of seafood soup with umami characteristics and add 20mg of sodium glutamate hyaluronic acid seasoning prepared in Example 10.

[0118] Example 23

[0119] Take 100g of seafood soup with umami characteristics and add 1mL of sodium glutamate hyaluronic acid soy sauce prepared in Example 11.

[0120] Comparative Example 1

[0121] Take 100g of seafood soup, a dish known for its umami flavor, and add 20mg of monosodium glutamate.

[0122] Comparative Example 2

[0123] Take 100g of pickled fish, a dish with a sour taste, and add 20mg of monosodium glutamate.

[0124] Comparative Example 3

[0125] Take 100g of eggplant with a sweet flavor and add 20mg of monosodium glutamate.

[0126] Comparative Example 4

[0127] Take 100g of pickled cucumber, a vegetable with a salty flavor, and add 20mg of monosodium glutamate.

[0128] Comparative Example 5

[0129] Take 100g of seafood soup, a dish known for its umami flavor, and add 15mg of sodium hyaluronate (HA60) and 5mg of sodium glutamate, which have a full molecular weight distribution, to the dish after a simple mixture.

[0130] Comparative Example 6

[0131] Take 100g of seafood broth, a dish known for its umami flavor, and add 1mL of regular soy sauce.

[0132] Performance Test Item 2

[0133] This project aims to verify that the sodium glutamate hyaluronic acid prepared according to this invention can improve the flavor of dishes.

[0134] The flavor and richness of Examples 13-23 and Comparative Examples 1-6 were detected using an electronic tongue, and the specific implementation methods are as follows:

[0135] (1) Preparation of positive electrode cleaning solution: Accurately weigh 3.73g KCl, dissolve it with 250mL distilled water by stirring, then accurately add 150mL anhydrous ethanol, and add 0.28g KOH while stirring. After dissolving, transfer it to a 500mL volumetric flask and dilute with distilled water to obtain the positive electrode cleaning solution.

[0136] (2) Preparation of negative electrode cleaning solution: Measure 150 mL of anhydrous ethanol and 250 mL of distilled water and shake to mix well. Then add 4.5 mL of concentrated hydrochloric acid, stir and mix, transfer to a 500 mL volumetric flask, and dilute to volume with distilled water to obtain negative electrode cleaning solution.

[0137] (3) Preparation of reference solution: Accurately weigh 1.12g KCl and 0.023g tartaric acid, dissolve them in 300mL distilled water, transfer them to a 500mL volumetric flask, and distill the water to obtain the reference solution;

[0138] (4) Preparation of the test sample:

[0139] ① Put the finished vegetables into a blender and blend until they are crushed;

[0140] ② Accurately weigh 20.00g of the sample using a balance and place it in a beaker;

[0141] ③ Add 300ml of distilled water, cover with a glass lid, and boil on an electric stove;

[0142] ④ Filter the sample solution;

[0143] ⑤ Collect the filtrate. Prepare two replicates of each sample as test samples;

[0144] (5) Electronic tongue test: Pour the test sample obtained in step (4) into a special plastic cup for electronic tongue test, two cups for each test sample, 20ml in each cup; First, clean the sensor in the positive electrode cleaning solution obtained in step (1) and the negative electrode cleaning solution obtained in step (2) for 90s respectively. Then, clean it twice with the reference solution obtained in step (3). After that, zero the sensor at the equilibrium position for 30s. After reaching the equilibrium condition, start the test. The test time is 30s. After the test is completed, clean the sensor in the two sets of reference solutions for 5s respectively. Then, insert the sensor into the newly prepared reference solution for 30s to test the aftertaste. Record the response value of the sensor, which is the test result; For each sample, collect 6 parallel data and take the 3 experimental data after stabilization.

[0145] Table 2. Results of Electronic Tongue Detection

[0146] Example 13 7.52±0.03 1.52±0.03 3.23±0.02 1.34±0.03 7.63±0.02 Example 14 4.63±0.04 1.55±0.03 3.73±0.01 7.57±0.05 6.53±0.06 Example 15 5.67±0.03 6.21±0.05 4.21±0.04 1.73±0.04 8.13±0.04 Example 16 3.33±0.02 1.53±0.07 7.78±0.04 1.75±0.03 7.59±0.03 Example 17 5.43±0.03 1.41±0.04 3.16±0.03 1.20±0.04 4.54±0.03 Example 18 6.20±0.04 1.06±0.03 3.20±0.03 1.51±0.05 5.18±0.04 Example 19 5.20±0.03 1.27±0.01 2.23±0.05 1.11±0.04 4.92±0.02 Example 20 3.35±0.03 0.64±0.03 2.37±0.02 0.83±0.03 3.27±0.01 Example 21 3.72±0.05 0.77±0.08 2.65±0.03 0.92±0.04 3.40±0.02 Example 22 3.03±0.05 0.57±0.01 2.23±0.04 0.89±0.05 3.12±0.03 Example 23 7.28±0.03 1.33±0.02 7.43±0.04 1.23±0.05 8.37±0.03 Comparative Example 1 3.64±0.04 0.47±0.04 2.89±0.05 0.88±0.03 1.87±0.03 Comparative Example 2 2.56±0.03 0.45±0.05 2.78±0.05 3.23±0.03 2.89±0.02 Comparative Example 3 2.53±0.02 1.78±0.07 2.08±0.03 0.98±0.03 2.12±0.06 Comparative Example 4 1.24±0.06 0.32±0.02 4.85±0.04 0.74±0.03 1.29±0.04 Comparative Example 5 4.09±0.03 0.64±0.04 2.36±0.05 1.07±0.05 3.01±0.02 Comparative Example 6 4.53±0.04 0.46±0.04 4.63±0.03 0.83±0.03 3.87±0.05

[0147] Richness refers to the aftertaste of a sample's flavor, reflecting its persistence, also known as persistence. Test results show that, compared to Comparative Examples 1-4, Examples 13-16, with the addition of sodium glutamate hyaluronic acid seasoning, not only provide a certain umami flavor to dishes but also harmonize the overall taste, significantly enhancing the umami, sweetness, saltiness, sourness, and richness of the food, exhibiting a clear aroma-enhancing and flavor-enhancing effect. Compared to Examples 17-19, the glutamate hyaluronic acid seasoning prepared from sodium hyaluronic acid HA60 with a weight-average molecular weight of 600 kDa and a full molecular weight distribution, added in Example 13, has a better umami-enhancing and flavor-enhancing effect.

[0148] Compared to Examples 20-22, the dishes in Examples 13 and 17-19 exhibit a richer flavor profile, indicating that sodium glutamate-based sodium hyaluronate prepared from sodium hyaluronate with a full molecular weight distribution has a better flavor-enhancing effect than ordinary sodium hyaluronate. Compared to Comparative Example 5, the dishes in Example 13 exhibit a richer flavor profile, indicating that the stable combination of sodium glutamate and sodium hyaluronate provided by this invention has a better flavor-enhancing effect than a simple mixture of monosodium glutamate and sodium hyaluronate.

[0149] Compared to Comparative Example 6, the dishes in Example 23 with added sodium glutamate hyaluronic acid were significantly more varied, meaning that the soy sauce with added sodium glutamate hyaluronic acid showed a more pronounced flavor-enhancing and umami-enhancing effect than ordinary soy sauce.

[0150] It will be apparent to those skilled in the art that the present invention is not limited to the details of the exemplary embodiments described above, and that the invention can be implemented in other specific forms without departing from its spirit or essential characteristics. Therefore, the embodiments should be considered in all respects as exemplary and non-limiting, and the scope of the invention is defined by the appended claims rather than the foregoing description. Thus, all variations falling within the meaning and scope of equivalents of the claims are intended to be included within the present invention. No reference numerals in the claims should be construed as limiting the scope of the claims.

Claims

1. The use of sodium glutamate hyaluronic acid in the preparation of seasonings, wherein the sodium glutamate hyaluronic acid is sodium hyaluronic acid with L-sodium glutamate or L-glutamic acid linked by chemical bonds, wherein the sodium glutamate hyaluronic acid is full molecular weight sodium hyaluronic acid; the weight average molecular weight of the full molecular weight sodium hyaluronic acid is 300 kDa ~ 1500 kDa; the chemical bonds are ionic bonds formed by the carboxyl group in the sodium hyaluronic acid molecule and the ammonium group in the L-sodium glutamate molecule or the L-glutamic acid molecule.

2. The use according to claim 1, characterized in that, Each sodium glutamate hyaluronic acid molecule contains at least one L-sodium glutamate molecule or an L-glutamate molecule.

3. The use according to claim 1, characterized in that, The sodium hyaluronate containing glutamic acid contains 1% to 100% of the carboxyl groups of sodium hyaluronate bound to sodium L-glutamate or L-glutamic acid.

4. The use according to claim 3, characterized in that, In the sodium hyaluronate containing glutamic acid, 20% to 80% of the carboxyl groups are bound to sodium L-glutamate or L-glutamic acid.

5. The use according to claim 4, characterized in that, In the sodium hyaluronate containing glutamic acid, 40% to 60% of the carboxyl groups are bound to sodium L-glutamate or L-glutamic acid.

6. A condiment, characterized in that, Sodium glutamate hyaluronic acid is contained in the use as described in any one of claims 1-5.

7. The seasoning according to claim 6, characterized in that, It contains 0.0001wt% to 99.9999wt% sodium glutamate hyaluronic acid.

8. The seasoning according to claim 6, characterized in that, The seasonings mentioned are monosodium glutamate, soy sauce, soy sauce, vinegar, or hot pot base.

9. A method for preparing sodium glutamate hyaluronic acid for any of the uses described in claims 1-5, characterized in that, Includes the following steps: (1) Preparation of solution 1: Dissolve sodium hyaluronate to obtain a solution; (2) Preparation of solution 2: Dissolve L-glutamate sodium or L-glutamic acid and add hydrochloric acid to form glutamate hydrochloride solution; (3) Preparation of sodium glutamate hyaluronic acid: Add solution 2 to solution 1 according to the required binding ratio of glutamate on sodium hyaluronic acid, stir and react. After the reaction is completed, remove the unreacted glutamate and the sodium chloride produced by the reaction to obtain the sodium glutamate hyaluronic acid.

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