Flavoring compound as well as preparation method and application thereof

Abstract

The invention belongs to the technical field of food processing, and relates to a flavoring compound and a preparation method and application thereof.The glycolic acid and sodium glutamate react to generate glycolic acid glutamate, glycolic acid glutamate has higher taste irritation and can provide higher salty taste at low concentration, and therefore the purpose of reducing the salt dosage is achieved; the novel low-salt salt substitute product is obtained by mixing the low-salt salt substitute product with table salt, starch and edible mushroom polypeptide, the development of the low-salt salt substitute product embodies the innovation ability of modern food science and technology in the aspect of meeting the dual requirements of health and delicious taste, the sodium content in food can be effectively reduced, and public health is promoted.

Description

Technical Field

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

[0002] As a flavor-enhancing substance, monosodium glutamate can significantly enhance the taste and flavor of food, making dishes more delicious. Although monosodium glutamate adds a lot to the taste of food, it still contains sodium ions and cannot meet the "sodium salt reduction" requirement, especially for people with common diseases and chronic diseases in the elderly, such as hypertension, hyperlipidemia, and atherosclerosis, who need to strictly control their salt intake. Even for normal people, long-term intake of exogenous monosodium glutamate will cause an increase in the concentration of glutamate in the human body, and then a series of abnormal reactions will occur. Even if the daily intake is as low as 0.3-1.0g, the risk of abnormal reactions in the human body will increase after 5 years of continuous intake.

[0003] With the public's pursuit of healthy living, the development of "salt reduction and salt replacement" products is imperative. Currently, common low-salt salt substitutes include: modified sodium glutamate, potassium chloride, magnesium salt, seaweed extract, yeast extract, etc. Compared with ordinary low-salt salt substitutes, the modified sodium glutamate method allows food manufacturers to customize the sodium content according to specific application requirements, which is highly flexible; secondly, the modified sodium glutamate often has a stronger umami taste, reducing salt while maintaining the taste of food; thirdly, sodium glutamate itself is a common food additive, and its modified products are generally considered to be more acceptable to consumers than emerging alternatives in terms of safety; compared with other low-salt substitutes, modified sodium glutamate may be more cost-effective in the production process.

[0004] The 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 and phosphate 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-replacing 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 view of the problems existing in the prior art, the present invention provides a flavor compound and a preparation method and application thereof. A new compound, hydroxyacetic acid glutamate, is generated through the esterification reaction of hydroxyacetic acid and sodium glutamate. 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 scheme to achieve it: a flavor compound, specifically glycolic acid glutamate, with the following structural formula:

[0007]

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

[0009] Furthermore, in terms of mass fraction, the raw materials include 2% to 10% hydroxyacetic glutamate, 40% to 70% salt, 20% to 35% starch, and 1% to 5% 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, Pleurotus eryngii peptide, Auricularia auricula peptide, Hericium erinaceus peptide, and seafood mushroom peptide.

[0012] The present invention provides a method for preparing a flavor compound, the specific steps of which are as follows:

[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 to obtain 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 specifically comprises:

[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 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:

[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:

[0023] The concentrated liquid is spray-dried at 140-150° C. and passed through a 20-30 mesh sieve to obtain a 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 type of 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. The low-salt salt substitute product can significantly reduce the sodium content in food while maintaining the food flavor by adding glycolic acid glutamate, which helps to prevent health problems such as hypertension.

[0029] The present invention provides a low-salt salt substitute product, which achieves a balance between taste and health by precisely controlling the ratio of each raw material. Hydroxyacetic acid glutamate provides saltiness, salt assists in flavor enhancement, and starch and edible fungus polypeptides increase the taste and nutritional value of food. The taste threshold is measured using edible salt as the evaluation standard, and the results show that the saltiness can be further enhanced. The preparation method is relatively simple and low in cost, and is therefore suitable for promotion and application.

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

[0031] The present invention utilizes sodium glutamate and glycolic acid to undergo an esterification reaction, and simultaneously utilizes dimethyl sulfoxide to improve the reaction efficiency and product stability; concentrated sulfuric acid is used as a catalyst for the esterification reaction, which not only accelerates the reaction process, but also can be used as a water absorbent to promote the reaction in the direction of generating esters, thereby increasing the yield of esters and generating glycolic acid glutamate. In general, through a novel method for chemically modifying sodium glutamate, the chemical equation is:

[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 without affecting 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. Taking edible salt as the evaluation standard, the taste threshold was measured, 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 threshold of the synthetic glycolic acid glutamate of Examples 1 to 6.

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

[0037] The present invention is further described below in conjunction with the accompanying drawings and specific embodiments. The following embodiments are only used to more clearly illustrate the technical solution of the present invention, and cannot be used to limit the protection scope 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, the generated glycolic acid glutamate (COOH-CH2-COO-CH-NH2-(CH2)2-COONa);

[0044] (3) The reaction solution is 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 by 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 the 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, by mass fraction, 2% to 10% of glutamate glycolate, 40% to 70% of salt, 20% to 35% of starch, and 1% to 5% of edible fungus polypeptide are included.

[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 peptides, enoki mushroom peptides, Agaricus blazei peptides, Ganoderma lucidum peptides, Pleurotus eryngii peptides, Auricularia auricula peptides, Hericium erinaceus peptides, and seafood mushroom peptides.

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

[0051] Embodiment 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 by a spray dryer at 150° C. and passed through a 20-mesh sieve to obtain glycolic acid glutamate powder.

[0058] Embodiment 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 by a spray dryer at 140° C. and passed through a 30-mesh sieve to obtain glycolic acid glutamate powder.

[0065] Embodiment three:

[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 its original volume using a rotary evaporator.

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

[0072] Embodiment 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 by a spray dryer at 150° C. and passed through a 30-mesh sieve to obtain glycolic acid glutamate powder.

[0079] Embodiment five:

[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% 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.

[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 by a spray dryer at 150° C. and passed through a 30-mesh sieve to obtain glycolic acid glutamate powder.

[0086] Embodiment six:

[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 by 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 thereof were as follows:

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

[0096] Embodiment eight:

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

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

[0099] Embodiment nine:

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

[0103] The glycolic acid glutamate powder obtained in Example 6 was compounded with salt, starch and edible fungus polypeptide. The contents thereof 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. The natural sodium glutamate and glycolic acid undergo esterification reaction to generate glycolic acid glutamate. The molecular structure of the product glycolic acid glutamate is as follows: Figure 1 , glycolic acid glutamate can be used as a precursor of umami or salty compounds; in addition, since glycolic acid and glutamic acid are both naturally occurring compounds, their synthetic products will also be less toxic; the ester bond in glycolic acid glutamate can be hydrolyzed in the digestive tract to produce glycolic acid and glutamic acid, both of which are substances naturally metabolized by the human body. In short, glycolic acid glutamate is a potential compound in food seasoning with good safety.

[0107] 2. Taking the edible salt sold in the market as the benchmark, the taste thresholds of Examples 1 to 6 were measured by the minimum change method. Based on the evaluation of the taste thresholds of all Examples by 10 tasters, the taste threshold results of all Examples are as follows: Figure 2 As shown, among them: Example 6> Example 5> Example 4> Example 3> Example 2> Example 1, so the best condition for modifying sodium glutamate is 1.52% glycolic acid and 10% dimethyl sulfoxide (DMSO) in the sodium glutamate solution. The taste threshold of glycolic acid glutamate generated under this condition is the largest (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 used to compound 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. Based on the evaluation of the taste threshold values ​​of all examples by 10 tasters, the taste threshold values ​​of all examples were obtained as follows: 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 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 the amount of salt used.

[0110] The present invention provides a novel method for chemically modifying sodium glutamate, wherein glycolic acid (C2H4O3) reacts with sodium glutamate (C5H7NO4Na) to generate glycolic acid glutamate (C2H3O2-CO-C5H7NO4Na) and water (H2O), wherein glycolic acid glutamate has a stronger taste irritation and can provide a stronger salty taste at a low concentration, thereby achieving the purpose of reducing the amount of salt used, and then mixed with salt, starch, and edible fungus polypeptide to obtain a novel low-salt salt substitute product. Among them, DMSO improves the reaction efficiency and product stability, and spray drying ensures the uniformity of the complex. The method prepares a new, edible and safe salt substitute product, which has a simple preparation method and low cost, and provides more choices for consumers who need to control sodium intake. It also means that the sodium content in food can be effectively reduced without sacrificing flavor, 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 the structural formula is as follows:

2. A low-salt salt substitute product, characterized in that: The invention comprises 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 fraction, 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, Pleurotus eryngii 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 to obtain 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, characterized in that: The step of mixing the sodium glutamate solution with glycolic acid and dimethyl sulfoxide to obtain a mixed solution specifically comprises: 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, characterized in that: 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, 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 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° C. and passed through a 20-30 mesh sieve to obtain a flavor compound.

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