A flavor compound and its preparation method and application

Abstract

The present invention belongs to the field of food processing technology and relates to a flavor compound, a preparation method and an application thereof. Hydroxyacetic acid glutamate is generated by the reaction of glycolic acid and sodium glutamate. Hydroxyacetic acid glutamate has a stronger taste stimulation and can provide a stronger salty taste at a low concentration, thereby achieving the purpose of reducing salt usage. Hydroxyacetic acid glutamate is then combined with salt, starch, and edible fungus polypeptides to obtain a new low-salt salt substitute product. The development of this low-salt salt substitute product reflects the innovative ability of modern food technology in meeting the dual needs of health and deliciousness, can effectively reduce the sodium content in food, and promote public health.

Description

Technical Field

[0001] The invention discloses a flavor compound, a preparation method and application thereof, and belongs to the technical field of food processing. Background Art

[0002] Monosodium glutamate, as a flavor-enhancing substance, can significantly enhance the taste and flavor of food, making dishes more palatable. While it adds a significant flavor boost, it still contains sodium ions, making it insufficient for sodium reduction. This is especially true for those with chronic conditions common in the elderly, such as hypertension, hyperlipidemia, and atherosclerosis, who require strict salt control. Even in healthy individuals, long-term consumption of exogenous monosodium glutamate can cause elevated glutamate concentrations in the body, leading to a series of adverse reactions. Even with daily intake as low as 0.3-1.0g, the risk of adverse reactions increases after five years of continuous intake.

[0003] With the public's pursuit of a healthier lifestyle, the development of "salt reduction and salt replacement" products is imperative. Currently, common low-salt salt substitutes include modified monosodium glutamate, potassium chloride, magnesium salts, seaweed extract, and yeast extract. Compared to ordinary low-salt salt substitutes, modified monosodium glutamate allows food manufacturers to customize the sodium content according to specific application requirements, providing greater flexibility. Secondly, modified monosodium glutamate often has a stronger umami flavor, reducing salt while maintaining the taste of food. Thirdly, monosodium glutamate itself is a common food additive, and its modified products are generally considered to be more acceptable to consumers in terms of safety than emerging alternatives. Compared with other low-salt substitutes, modified monosodium glutamate may be more cost-effective in production.

[0004] Methods for modifying monosodium glutamate mainly include chemical modification and physical modification. Chemical modification mainly changes the properties of monosodium glutamate by adding chemical substances, such as the reaction of phosphate with monosodium glutamate to form monosodium glutamate phosphate. Although this method can increase the umami taste of monosodium glutamate, the nutritional value of monosodium glutamate may be affected during the modification process, and additional purification steps are required to remove by-products, which may increase production costs. The physical modification method is to crystallize monosodium glutamate to change the crystal form of monosodium glutamate, thereby changing its solubility and stability. This method will affect the taste and flavor of monosodium glutamate in an undirected manner. Therefore, it is necessary to develop a salt-reducing and salt-substituting seasoning that provides a stronger salty taste at low salt concentrations, so as to protect people's lives and health while enjoying a delicious life. Summary of the Invention

[0005] In response to the problems existing in the prior art, the present invention provides a flavor compound, a preparation method and application thereof. Through the esterification reaction of glycolic acid and sodium glutamate, a new compound, glycolic acid glutamate, is generated. This ester compound can significantly enhance the salty taste and has better flavor release characteristics.

[0006] In order to achieve the above object, the present invention adopts the following technical solution to achieve it: a flavor compound, specifically glycolic acid glutamate, with the following structural formula:

[0007]

[0008] The present invention provides a low-salt salt substitute product, comprising the glycolic acid glutamate.

[0009] Furthermore, the raw materials include, by mass fraction, 2% to 10% of glutamate glycolate, 40% to 70% of table salt, 20% to 35% of starch, and 1% to 5% of edible fungus polypeptide.

[0010] Furthermore, the starch is corn starch or sweet potato starch.

[0011] Furthermore, the edible fungus polypeptide is one or more of shiitake mushroom peptide, enoki mushroom peptide, Agaricus blazei peptide, Ganoderma lucidum peptide, King oyster mushroom peptide, Auricularia auricula peptide, Hericium erinaceus peptide, and seafood mushroom peptide.

[0012] The present invention provides a method for preparing a flavor compound, which comprises the following steps:

[0013] mixing the sodium glutamate solution, glycolic acid and dimethyl sulfoxide to obtain a mixed solution;

[0014] adding a catalyst to the mixed solution and heating the solution to react, thereby obtaining a reaction solution;

[0015] The catalyst in the reaction solution is removed, concentrated, and dried to obtain a flavor compound, namely glycolic acid glutamate.

[0016] Furthermore, the step of mixing the sodium glutamate solution with glycolic acid and dimethyl sulfoxide to obtain a mixed solution is specifically as follows:

[0017] 0.76% to 1.52% of glycolic acid and 5% to 10% of dimethyl sulfoxide are added to a 10% sodium glutamate solution to obtain a mixed solution.

[0018] Furthermore, the step of adding a catalyst to the mixed solution and heating the mixture to react to obtain a reaction solution is specifically as follows:

[0019] Add concentrated sulfuric acid as a catalyst to the mixed solution and react at 80° C. to 100° C. for 2 to 3 hours to obtain a reaction solution.

[0020] Furthermore, the steps of removing the catalyst from the reaction solution, concentrating, and drying to obtain the flavor compound, i.e., glycolic acid glutamate, are specifically as follows:

[0021] The catalyst in the reaction solution is removed, and the reaction solution is concentrated to 1 / 4 to 1 / 2 of the original volume by rotary evaporation to obtain a concentrated solution.

[0022] Furthermore, the steps of removing the catalyst from the reaction solution, concentrating, and drying to obtain the flavor compound, i.e., glycolic acid glutamate, are specifically as follows:

[0023] The concentrated liquid is spray-dried at 140-150 DEG C and passed through a 20-30 mesh sieve to obtain the flavor compound.

[0024] Compared with the prior art, the present invention has the following beneficial effects:

[0025] The present invention provides a flavor compound, the structural formula of which is as follows:

[0026]

[0027] As a new flavor compound, glycolic acid glutamate has stronger taste stimulation and can provide a stronger salty taste at low concentrations, which helps reduce the amount of salt in food and meet the needs of a healthy diet.

[0028] The present invention provides a low-salt salt substitute product, comprising the above-mentioned glycolic acid glutamate. By adding glycolic acid glutamate, the low-salt salt substitute product can significantly reduce the sodium content in food while maintaining the flavor of the food, thereby helping to prevent health problems such as hypertension.

[0029] The present invention provides a low-salt salt substitute product that achieves a balance between taste and health by precisely controlling the ratios of the various ingredients. Glutamate glycolate provides saltiness, salt enhances flavor, and starch and edible fungus peptides enhance the food's texture and nutritional value. Taste thresholds measured using table salt as the standard for evaluation demonstrate a significantly enhanced saltiness perception. This preparation method is relatively simple and low-cost, making it suitable for widespread adoption and application.

[0030] The present invention provides a method for preparing a flavor compound, comprising mixing a sodium glutamate solution, glycolic acid, and dimethyl sulfoxide (DMSO), adding a catalyst for reaction, removing the catalyst, concentrating, and drying to obtain glycolic acid glutamate. The preparation method is simple and efficient, synthesizing glycolic acid glutamate through an esterification reaction while utilizing DMSO to improve reaction efficiency and product stability.

[0031] The present invention utilizes sodium glutamate and glycolic acid to undergo an esterification reaction, while simultaneously utilizing dimethyl sulfoxide to improve reaction efficiency and product stability. Concentrated sulfuric acid, acting as a catalyst for the esterification reaction, not only accelerates the reaction process but also acts as a water absorbent to promote the reaction toward ester formation, thereby increasing the ester yield and producing glycolic acid glutamate. Overall, the novel method for chemically modifying sodium glutamate yields the chemical equation:

[0032] C2H4O3+C5H7NO4Na→C2H3O3-COO-C4H7NO2Na+H2O

[0033] After the reaction is completed, alkali is added to neutralize the remaining concentrated H2SO4 to generate sulfates, and these salts can be removed by simple water washing and do not affect the synthesis of the final product. Among them, the generated glycolic acid glutamate is used as a precursor of umami or salty compounds for food seasoning. The metabolites of glycolic acid glutamate are similar to glycolic acid and glutamic acid, and these substances are generally regarded as safe (GRAS) within the recommended limits of use. This modification method does not generate any by-products. The generated glycolic acid glutamate forms a complex with sodium chloride. Since the compound after the esterification reaction has a stronger taste irritation, it can provide a stronger salty taste at low concentrations, thereby achieving the purpose of reducing the amount of salt used. The taste threshold was measured using edible salt as the evaluation standard, and the results showed that the salty taste can be significantly improved. BRIEF DESCRIPTION OF THE DRAWINGS

[0034] Figure 1 It is the molecular structure formula of glycolic acid glutamate.

[0035] Figure 2 The taste thresholds of the synthesized glycolic glutamate of Examples 1 to 6.

[0036] Figure 3 is the taste threshold of all examples. DETAILED DESCRIPTION

[0037] The present invention will be further described below in conjunction with the accompanying drawings and specific embodiments. The following examples are only used to more clearly illustrate the technical solutions of the present invention and are not intended to limit the scope of protection of the present invention.

[0038] The present invention provides a flavor compound, and the specific preparation steps are as follows:

[0039] (1) Dissolve sodium glutamate powder in water to prepare a 10% sodium glutamate solution.

[0040] (2) Add 0.76% to 1.52% of glycolic acid, 5% to 10% of dimethyl sulfoxide (DMSO) and concentrated sulfuric acid as a catalyst to the sodium glutamate solution, and react at 80°C to 100°C for 2 to 3 hours to obtain a reaction solution. The reaction principle is as follows:

[0041] COOH-CH2OH+HOOC-CH2-CH2-CH(NH)2-COONa→

[0042] COOH-CH2-COO-CH-NH2-(CH2)2-COONa

[0043] Among them, glycolic acid glutamate (COOH-CH2-COO-CH-NH2-(CH2)2-COONa) is generated;

[0044] (3) The reaction solution was concentrated to 1 / 4 to 1 / 2 of the original volume using a rotary evaporator to obtain a concentrated solution.

[0045] (4) The concentrated liquid is dried in a spray dryer at a temperature of 140-150°C and passed through a 20-30 mesh sieve to obtain a flavor compound, hydroxyacetic acid glutamate powder, which can be used as a salt reduction and salt replacement product. Salt reduction and salt replacement refers to reducing the amount of salt used by enhancing flavor (saltiness).

[0046] A low-salt salt substitute product can be obtained by compounding the above-mentioned glycolic acid glutamate with other salt substitute ingredients, wherein the other salt substitute ingredients include: table salt, starch, and edible fungus polypeptide.

[0047] Preferably, based on mass fraction, the ingredients include 2% to 10% glutamate glycolate, 40% to 70% salt, 20% to 35% starch, and 1% to 5% edible fungus polypeptide.

[0048] Preferably, the starch is corn starch or sweet potato starch.

[0049] Preferably, the edible fungus polypeptide is selected from one or more of shiitake mushroom peptide, enoki mushroom peptide, Agaricus blazei peptide, Ganoderma lucidum peptide, King oyster mushroom peptide, Auricularia auricula peptide, Hericium erinaceus peptide, and seafood mushroom peptide.

[0050] The low-salt salt substitute product of the present invention can be used in the fields of condiments, ready-to-eat foods, functional foods, etc., and provides healthier food choices by reducing sodium intake.

[0051] Example 1:

[0052] Chemical modification and compounding of sodium glutamate:

[0053] (1) Dissolve commercially available sodium glutamate powder in water to prepare a 10% solution.

[0054] (2) 0.76% of glycolic acid and 5% of dimethyl sulfoxide (DMSO) were added to the solution, and concentrated H2SO4 as a catalyst was added, and the mixture was reacted at 80°C for 2 hours to obtain a reaction solution.

[0055] (3) After the reaction is completed, an alkaline substance (sodium carbonate) is added to neutralize the remaining concentrated sulfuric acid in the reaction system. The sulfate (sodium sulfate) generated during the neutralization process is removed by simple water washing.

[0056] (4) The reaction solution was concentrated to 1 / 4 of the original volume using a rotary evaporator.

[0057] (5) The concentrated solution was dried in a spray dryer at 150° C. and passed through a 20-mesh sieve to obtain glycolic acid glutamate powder.

[0058] Example 2:

[0059] Chemical modification and compounding of sodium glutamate:

[0060] (1) Dissolve commercially available sodium glutamate powder in water to prepare a 10% solution.

[0061] (2) 0.76% of glycolic acid and 10% of dimethyl sulfoxide (DMSO) were added to the solution, and concentrated H2SO4 as a catalyst was added, and the mixture was reacted at 90°C for 1.5 hours to obtain a reaction solution.

[0062] (3) After the reaction is completed, an alkaline substance (sodium carbonate) is added to neutralize the remaining concentrated sulfuric acid in the reaction system. The sulfate (sodium sulfate) generated during the neutralization process is removed by simple water washing.

[0063] (4) The reaction solution was concentrated to 1 / 3 of the original volume using a rotary evaporator.

[0064] (5) The concentrated solution was dried in a spray dryer at 140° C. and passed through a 30-mesh sieve to obtain glycolic acid glutamate powder.

[0065] Example 3:

[0066] Chemical modification and compounding of sodium glutamate:

[0067] (1) Dissolve commercially available sodium glutamate powder in water to prepare a 10% solution.

[0068] (2) 1.52% of glycolic acid and 7% of dimethyl sulfoxide (DMSO) were added to the solution, and concentrated H2SO4 as a catalyst was added, and the mixture was reacted at 100°C for 3 hours to obtain a reaction solution.

[0069] (3) After the reaction is completed, an alkaline substance (sodium carbonate) is added to neutralize the remaining concentrated sulfuric acid in the reaction system. The sulfate (sodium sulfate) generated during the neutralization process is removed by simple water washing.

[0070] (4) The reaction solution was concentrated to 1 / 2 of the original volume using a rotary evaporator.

[0071] (5) The concentrated solution was dried in a spray dryer at 145° C. and passed through a 25-mesh sieve to obtain glycolic acid glutamate powder.

[0072] Example 4:

[0073] Chemical modification and compounding of sodium glutamate:

[0074] (1) Dissolve commercially available sodium glutamate powder in water to prepare a 10% solution.

[0075] (2) 0.76% of glycolic acid and 5% of dimethyl sulfoxide (DMSO) were added to the solution, and concentrated H2SO4 as a catalyst was added, and the mixture was reacted at 80°C for 2 hours to obtain a reaction solution.

[0076] (3) After the reaction is completed, an alkaline substance (sodium carbonate) is added to neutralize the remaining concentrated sulfuric acid in the reaction system. The sulfate (sodium sulfate) generated during the neutralization process is removed by simple water washing.

[0077] (4) The reaction solution was concentrated to 1 / 4 of the original volume using a rotary evaporator.

[0078] (5) The concentrated solution was dried in a spray dryer at 150° C. and passed through a 30-mesh sieve to obtain glycolic acid glutamate powder.

[0079] Embodiment 5:

[0080] Chemical modification and compounding of sodium glutamate:

[0081] (1) Dissolve commercially available sodium glutamate powder in water to prepare a 10% solution.

[0082] (2) 1.2% glycolic acid and 10% dimethyl sulfoxide (DMSO) were added to the solution, and concentrated H2SO4 as a catalyst was added, and the mixture was reacted at 80°C for 2 hours to obtain a reaction solution.

[0083] (3) After the reaction is completed, an alkaline substance (sodium carbonate) is added to neutralize the remaining concentrated sulfuric acid in the reaction system. The sulfate (sodium sulfate) generated during the neutralization process is removed by simple water washing.

[0084] (4) The reaction solution was concentrated to 1 / 4 of the original volume using a rotary evaporator.

[0085] (5) The concentrated solution was dried in a spray dryer at 150° C. and passed through a 30-mesh sieve to obtain glycolic acid glutamate powder.

[0086] Example 6:

[0087] Chemical modification and compounding of sodium glutamate:

[0088] (1) Dissolve commercially available sodium glutamate powder in water to prepare a 10% solution.

[0089] (2) 1.52% of glycolic acid and 10% of dimethyl sulfoxide (DMSO) were added to the solution, and concentrated H2SO4 as a catalyst was added, and the mixture was reacted at 80°C for 2 hours to obtain a reaction solution.

[0090] (3) After the reaction is completed, an alkaline substance (sodium carbonate) is added to neutralize the remaining concentrated sulfuric acid in the reaction system. The sulfate (sodium sulfate) generated during the neutralization process is removed by simple water washing.

[0091] (4) The reaction solution was concentrated to 1 / 4 of the original volume using a rotary evaporator.

[0092] (5) The concentrated solution was dried in a spray dryer at 150° C. and passed through a 30-mesh sieve to obtain glycolic acid glutamate powder.

[0093] Embodiment seven:

[0094] The glycolic acid glutamate powder obtained in Example 6 was compounded with salt, starch, and edible fungus polypeptide. The contents were as follows:

[0095] raw material content% Glutamate glycolate 10％ salt 60％ corn starch 25％ Edible fungus peptides (shiitake mushroom peptides) 5％

[0096] Embodiment 8:

[0097] The glycolic acid glutamate powder obtained in Example 6 was compounded with salt, starch, and edible fungus polypeptide. The contents were as follows:

[0098] raw material content% Glutamate glycolate 2％ salt 70％ corn starch 27％ Edible fungus peptides (shiitake mushroom peptides) 1％

[0099] Embodiment 9:

[0100] The glycolic acid glutamate powder obtained in Example 6 was compounded with salt, starch, and edible fungus polypeptide. The contents were as follows:

[0101] raw material content% Glutamate glycolate 4％ salt 60％ sweet potato starch 35％ Edible fungus peptides (shiitake mushroom peptides, seafood mushroom peptides) 0.5% each

[0102] Embodiment 10:

[0103] The glycolic acid glutamate powder obtained in Example 6 was compounded with salt, starch, and edible fungus polypeptide. The contents were as follows:

[0104] raw material content% Glutamate glycolate 5％ salt 70％ corn starch 20％ Edible fungus peptides (shiitake mushroom peptides, seafood mushroom peptides) 2.5% each

[0105] Test Example 1

[0106] 1. Esterification reaction between natural sodium glutamate and glycolic acid to produce glycolic acid glutamate. The molecular structure of the product glycolic acid glutamate is as follows: Figure 1 Glutamate glycolate can serve as a precursor to umami or salty compounds. Furthermore, because both glycolic acid and glutamic acid are naturally occurring compounds, their synthetic products are also less toxic. The ester bond in glutamate glycolate hydrolyzes in the digestive tract, producing glycolic acid and glutamic acid, both of which are naturally metabolized by the human body. In summary, glutamate glycolate is a promising compound for food seasoning, with a good safety profile.

[0107] 2. The taste thresholds of Examples 1 to 6 were measured using the minimum change method with commercially available edible salt as the benchmark. Based on the evaluation of the taste thresholds of all examples by 10 tasters, the taste threshold results of all examples were obtained as follows: Figure 2 As shown, among them: Example 6 > Example 5 > Example 4 > Example 3 > Example 2 > Example 1. Therefore, the optimal conditions for modifying sodium glutamate are 1.52% glycolic acid and 10% dimethyl sulfoxide (DMSO) in the sodium glutamate solution. The glycolic acid glutamate produced under these conditions has the highest taste threshold (Example 6), indicating that glycolic acid glutamate has a stronger taste irritation and can provide a stronger salty taste.

[0108] Test Example 2

[0109] Based on the results of Test Example 1, the glycolic acid glutamate of Example 6 was compounded to obtain a new low-salt salt substitute product. Taking the edible salt sold on the market as the benchmark, the threshold values ​​of all Examples 7 to 10 were measured. The taste threshold values ​​of all Examples were evaluated by 10 tasters. The following results were obtained: Figure 3 As shown, among them: Example 9> Example 8> Example 7> Example 10, so in the process of compounding to obtain a new low-salt salt substitute product, the best formula (Example 9) is 4% hydroxyacetic acid glutamate, 60% salt, 35% corn starch, 0.5% each of shiitake mushroom peptide and seafood mushroom peptide. This product can provide a stronger salty taste at a low salt concentration, thereby achieving the purpose of reducing salt usage.

[0110] The present invention provides a novel method for chemically modifying sodium glutamate, in which glycolic acid (C2H4O3) reacts with sodium glutamate (C5H7NO4Na) to generate glycolic acid glutamate (C2H3O2-CO-C5H7NO4Na) and water (H2O). Hydroxyacetic acid glutamate has a stronger taste irritation and can provide a stronger salty taste at low concentrations, thereby achieving the purpose of reducing salt dosage. It is then mixed with table salt, starch, and edible fungus polypeptides to obtain a novel low-salt salt substitute product. Among them, DMSO improves reaction efficiency and product stability, and spray drying ensures the uniformity of the complex. This method prepares a new, edible and safe salt substitute product with a simple preparation method and low cost, providing more choices for consumers who need to control sodium intake. It also means that without sacrificing flavor, the sodium content in food can be effectively reduced, thereby promoting public health. The development of this low-salt salt substitute product reflects the innovative ability of modern food technology in meeting the dual needs of health and deliciousness.

Claims

1. A flavor compound, characterized in that Specifically, it is glycolic acid glutamate, and its structural formula is as follows:

2. A low-salt salt substitute product, characterized in that: The invention relates to a method for preparing the present invention comprising the glycolic acid glutamate according to claim 1.

3. A low-salt salt substitute product according to claim 2, characterized in that: Calculated by mass, the raw materials include 2% to 10% of hydroxyacetic glutamate, 40% to 70% of salt, 20% to 35% of starch, and 1% to 5% of edible fungus polypeptide.

4. A low-salt salt substitute product according to claim 3, characterized in that: The starch is corn starch or sweet potato starch.

5. A low-salt salt substitute product according to claim 3, characterized in that: The edible fungus polypeptide is one or more of shiitake mushroom peptide, enoki mushroom peptide, Agaricus blazei peptide, Ganoderma lucidum peptide, King oyster mushroom peptide, Auricularia auricula peptide, Hericium erinaceus peptide, and seafood mushroom peptide.

6. A method for preparing a flavor compound, characterized in that: The specific steps are as follows: mixing the sodium glutamate solution, glycolic acid and dimethyl sulfoxide to obtain a mixed solution; adding a catalyst to the mixed solution and heating the solution to react, thereby obtaining a reaction solution; The catalyst in the reaction solution is removed, concentrated, and dried to obtain a flavor compound, namely glycolic acid glutamate.

7. The method for preparing a flavor compound according to claim 6, wherein: The step of mixing the sodium glutamate solution, glycolic acid and dimethyl sulfoxide to obtain a mixed solution is specifically as follows: 0.76% to 1.52% of glycolic acid and 5% to 10% of dimethyl sulfoxide are added to a 10% sodium glutamate solution to obtain a mixed solution.

8. The method for preparing a flavor compound according to claim 6, wherein: The step of adding a catalyst to the mixed solution and heating the solution to obtain a reaction solution is specifically as follows: Add concentrated sulfuric acid as a catalyst to the mixed solution and react at 80° C. to 100° C. for 2 to 3 hours to obtain a reaction solution.

9. The method for preparing a flavor compound according to claim 6, wherein: The steps of removing the catalyst from the reaction solution, concentrating, and drying to obtain the flavor compound, i.e., glycolic acid glutamate, are specifically as follows: The catalyst in the reaction solution is removed, and the reaction solution is concentrated to 1 / 4 to 1 / 2 of the original volume by rotary evaporation to obtain a concentrated solution.

10. The method for preparing a flavor compound according to claim 9, characterized in that: The steps of removing the catalyst from the reaction solution, concentrating, and drying to obtain the flavor compound, i.e., glycolic acid glutamate, are specifically: The concentrated liquid is spray-dried at 140-150 DEG C and passed through a 20-30 mesh sieve to obtain the flavor compound.

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