Method for improving content of meaty substance in thiamine degradation product and application of degradation product
By using food-grade additives and edible oil extraction technology during the thiamine degradation process, the generation of meat flavor compounds was increased, solving the problem of insufficient generation of meat flavor compounds during thiamine degradation, thus achieving cost reduction and improved meat flavor effect.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- BEIJING HONGXI ESSENCE SPICES CO LTD
- Filing Date
- 2019-09-10
- Publication Date
- 2026-05-01
AI Technical Summary
In the existing technology, the production of two meat flavor compounds, 2-methyl-3-mercaptofuran and bis(2-methyl-3-furanyl)disulfide, has not been effectively increased during the degradation of thiamine, resulting in a high cost of meat flavoring.
Food-grade phosphates or lactates are used as additives, mixed with thiamine hydrochloride and solvent in a closed reaction vessel, and the reaction is carried out by controlling the temperature and time. Then, edible oil or caprylic/capric triglyceride is used for extraction, separation and drying to obtain a high-concentration meat flavoring oil.
It significantly increased the amount of meat flavor compounds generated in thiamine degradation products, reduced production costs, and removed bitter substances through extraction and separation, thereby enhancing the meat flavor effect.
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Abstract
Description
Technical Field
[0001] This invention relates to a method for increasing the content of meat flavor substances in thiamine degradation products and the application of the degradation products, belonging to the field of food processing technology. Background Technology
[0002] Thiamine (vitamin B1) provides a meaty flavor and is therefore often used in the preparation of savory reactive flavorings. Thiamine is mainly available in the market as thiamine hydrochloride, priced between 300-500 Nm / kg. Because thiamine and its derivatives are primarily derived from chemical synthesis, their prices fluctuate significantly due to raw material and environmental requirements. As it is a crucial raw material in meat flavorings, it is often considered a significant factor influencing the cost of meat flavorings.
[0003] The degradation mechanism of thiamine is shown in Formula I. Pathway 1 involves the cleavage of the CN atom connected to the methylene bridge in the quaternary ammonium salt of thiamine, generating thiothiazole and pyrimidine compounds [Journal of Food Science, 1972, 37]. Pathway 2 involves ring-opening of the CN atom at position 2 of the thiazole in thiamine, removing the functional group attached to the sulfur atom, generating pyrimidine compounds and 5-hydroxy-3-mercapto-2-pentanone [Annals of the New York Academy of Sciences. 2008, 1126(1): 66-71; Journal of Agricultural and Food Chemistry. 1990, 38(3): 777-791]. The 5-mercaptopentanone compounds are highly reactive and can continue to react, forming the meat aroma compound 2-methyl-3-mercaptofuran, which can be further oxidized to bis(2-methyl-3-furanyl)disulfide. These two compounds are important meat aroma compounds and play a major role in the meat aroma effect of thiamine. The main compound produced by the degradation of thiamine is thiothiazole, with very little meat flavoring compounds generated. Although 2-methyl-3-mercaptofuran and bis(2-methyl-3-furanyl)disulfide are used in meat flavorings at the ppm level, even minute differences can alter the meat flavor. These two compounds are relatively expensive monomers, typically costing 3000-5000 yuan / kg. Therefore, if thiamine can be efficiently degraded to produce these two meat flavoring compounds, the value of thiamine can be significantly increased.
[0004]
[0005] In 1969, R.G. Arnold separated the products of thiamine hydrochloride heated at 100°C for 15 min in a phosphate buffer solution (pH = 6.7), obtaining the formation rules of hydrogen sulfide, 2-methylthiophene, 2-methylfuran, and 2-methyl-4,5-dihydrothiophene (J. Agr. Food Chem, 1969, 17, 390). In 1972, B.K. Dwivedi and R.G. Arnold further adjusted the pH of the thiamine hydrochloride solution to 5.0, 6.0, and 7.0 using NaOH or phosphate buffer solution, and carried out thiamine degradation under three reaction conditions: 1. heating at 100°C for 30 min in a sealed water bath; 2. heating at 100°C for 30 min in an air-water bath; 3. heating at 121°C for 30 min in an autoclave. Subsequently, they identified the degradation product, thiothiazole, and studied its formation rules (Journal of Food Science, 1972, 37, 689). In 1973, researchers studied the ratio of thiothiazole degradation products to total thiamine degradation products at different time points (15 min, 30 min, 120 min) by adjusting the pH of thiamine hydrochloride solution to 3.5, 5.0, 6.0, 7.0, and 8.0 using phosphate buffer solution (Journal of Food Science, 1973, 37, 866). In the same year, BKDwivedi and RGARnold further investigated the formation of thiothiazole by adjusting the pH to 5.0, 6.0, 7.0, and 8.4 using NaOH, allowing the solution to stand for 2 hours, and then heating it at 120°C for 1 hour. They also analyzed the 2-acetyltetrahydrothiophene compound generated from thiamine degradation and summarized the thiophene compounds (Journal of Food Science, 1973, 38, 450). T.D. Morfee and B.J. Liska adjusted the pH of thiamine hydrochloride solutions to 5.9 and 7.4 using phosphate-buffered saline, followed by heating at 121°C for 40 min, and observed the formation of elemental sulfur (Journal of Dairy Science, 1972, 55, 123). In 1979, Joseph W. Bell et al. adjusted the pH of thiamine solutions to 6.60 using phosphate-citrate buffer and studied the effects of different reaction temperatures (70-90°C) and reactor materials on thiamine degradation. Their results showed that thiamine degradation mainly occurred in a homogeneous phase, with little effect from the reactor wall material (J. Agr. Food Chem., 1979, 27, 384).In 2018, Adrienne Voelker et al. studied the changes in thiamine hydrochloride and thiamine nitrate after 6 months of storage at 25, 40, 60, 70, and 80°C, explaining the results through the solubility, pH value, and corresponding activation energy of the two solutions (Food Research International, 2018, 112, 443). Additionally, in 2004, Xie Jianchun et al. identified 26 sulfur-containing compounds by heating a 1,2-propanediol solution of thiamine in a microwave oven on medium and high heat for 5 minutes. These included thiophene, thiazole, sulfur-substituted furans, aliphatic sulfur-containing compounds, and sulfur-containing carbonyl compounds. Among them, 2-methyl-3-furanthiol and 2-acetylthiophene compounds possessed characteristic structural units of meat-flavor compounds (Food Science, 2004, 25, 241).
[0006] Although scholars have studied the above reaction patterns, the reported methods for degrading thiamine by heating or adjusting pH (using NaOH solution or phosphate buffer solution) have only investigated the effects of specific pH values on the main byproducts such as thiazoles and thiophenes. The effects on the formation of 2-methyl-3-mercaptofuran and bis(2-methyl-3-furanyl)disulfide have not been reported. Because the degradation process of thiamine involves competitive reactions, only by increasing the formation of these two meat flavor compounds—2-methyl-3-mercaptofuran and bis(2-methyl-3-furanyl)disulfide—can they play a more significant role in flavor production, reduce the cost of reactive flavors, and simultaneously improve the meaty texture of reactive flavors. Summary of the Invention
[0007] In view of this, one objective of the present invention is to provide a method for increasing the content of meat flavor compounds in thiamine degradation products, which has low production cost, high yield of meat flavor compounds, stable process, simple operation, and is suitable for large-scale preparation. A second objective of the present invention is to provide an application of thiamine degradation products. These products can be directly added as semi-finished raw materials to the reaction to prepare flavorings and enhance the meat flavor of the product. Alternatively, they can be extracted and separated by edible oil or caprylic / capric triglycerides to obtain a high-concentration meat flavoring oil. This flavoring oil avoids the influence of water-soluble bitter substances produced by thiamine degradation on the taste and can enhance the meat flavor when used in the reaction or flavoring products.
[0008] To achieve the above objectives, the technical solution of the present invention is as follows.
[0009] A method for increasing the content of meat flavor compounds in thiamine degradation products, the method comprising the following steps:
[0010] Thiamine hydrochloride, food additives and solvents are added to a sealed reaction vessel and stirred at 80-140℃ for 10-180 min. After the reaction is completed, the mixture is cooled to obtain thiamine degradation products.
[0011] The food additive is a food-grade phosphate or a food-grade lactate.
[0012] The solvent is one or more of deionized water, glycerol, and propylene glycol;
[0013] The mass ratio of the thiamine hydrochloride to the solvent is 1:1 to 1:10;
[0014] The mass of the food-grade additive is 0.5%-4.0% of the total mass of thiamine hydrochloride and solvent.
[0015] Preferably, the food-grade phosphate is one or more of disodium hydrogen phosphate, sodium phosphate, sodium dihydrogen phosphate, dipotassium hydrogen phosphate, potassium phosphate, potassium dihydrogen phosphate, sodium pyrophosphate, and sodium tripolyphosphate.
[0016] Preferably, the food-grade lactate is sodium lactate or calcium lactate.
[0017] Preferably, the mass ratio of the thiamine hydrochloride to the solvent is 1:1 to 1:2.
[0018] Preferably, the mass of the food-grade additive is 1%-2% of the total mass of thiamine hydrochloride and solvent.
[0019] Preferably, the reaction temperature is 100-120℃ and the reaction time is 60-150 min.
[0020] An application of a thiamine degradation product, wherein the thiamine degradation product is used as a raw material for preparing meat flavoring.
[0021] An application of a thiamine degradation product, wherein the thiamine degradation product is extracted with an extractant, separated, and dried to obtain a meat-flavored seasoning oil; wherein the extractant is an edible oil or caprylic / capric triglyceride; and the mass ratio of the extractant to the thiamine degradation product is 0.5:1-10:1. The edible oil includes sunflower oil, rapeseed oil, rice bran oil, corn oil, flaxseed oil, peanut oil, and soybean oil, etc.
[0022] Preferably, the mass ratio of the extractant to the thiamine degradation product is 1:1 to 3:1.
[0023] An application of a meat-flavored seasoning oil, wherein the meat-flavored seasoning oil is used as a raw material for preparing meat flavoring.
[0024] Beneficial effects:
[0025] The method described in this invention can significantly increase the amount of meat flavor compounds generated during the degradation of thiamine. The phosphate or lactate raw materials used are inexpensive, the reaction process and operation are simple, and it is suitable for mass production. The thiamine degradation products can be directly used in the preparation of flavorings to enhance meat flavor and reduce costs. Furthermore, by extracting, separating, and drying the thiamine degradation products with edible oil or caprylic / capric triglycerides, meat flavoring oil can be obtained, removing bitter substances from the taste. This oil can also be used in meat flavoring reactions or flavoring products to enhance the meat flavor and reduce costs, showing broad application prospects. Attached Figure Description
[0026] Figure 1 The gas chromatogram of the thiamine degradation products in Comparative Example 1 is shown.
[0027] Figure 2 The gas chromatogram of the thiamine degradation products in Comparative Example 2 is shown.
[0028] Figure 3 The gas chromatogram of the thiamine degradation products in Comparative Example 3 is shown.
[0029] Figure 4 The gas chromatogram of the thiamine degradation products in Comparative Example 4 is shown.
[0030] Figure 5 This is a gas chromatogram of the thiamine degradation products in Example 1;
[0031] Figure 6 This is a gas chromatogram of the thiamine degradation products in Example 2;
[0032] Figure 7 This is a gas chromatogram of the thiamine degradation products in Example 3;
[0033] Figure 8 This is a gas chromatogram of the thiamine degradation products in Example 4;
[0034] Figure 9 This is a gas chromatogram of the thiamine degradation products in Example 5;
[0035] Figure 10 This is a gas chromatogram of the thiamine degradation products in Example 6;
[0036] Figure 11 This is a gas chromatogram of the thiamine degradation products in Example 7;
[0037] Figure 12 This is a gas chromatogram of the thiamine degradation products in Example 8;
[0038] Figure 13 This is a gas chromatogram of the thiamine degradation products in Example 9;
[0039] Figure 14 This is a gas chromatogram of the thiamine degradation products in Example 10;
[0040] Figure 15 This is a gas chromatogram of the thiamine degradation products in Example 11;
[0041] Figure 16 This is a gas chromatogram of the thiamine degradation products in Example 12;
[0042] Figure 17 This is a gas chromatogram of the thiamine degradation products in Example 13;
[0043] Figure 18 This is a gas chromatogram of the thiamine degradation products in Example 14;
[0044] Figure 19 This is a gas chromatogram of the thiamine degradation products in Example 15;
[0045] Figure 20 This is a gas chromatogram of the thiamine degradation products in Example 16;
[0046] Figure 21 This is a gas chromatogram of the thiamine degradation products in Example 17;
[0047] Figure 22 This is a gas chromatogram of the thiamine degradation products in Example 18;
[0048] Figure 23 This is a gas chromatogram of the thiamine degradation products in Example 19;
[0049] Figure 24 Here is a gas chromatogram of the thiamine degradation products in Example 20;
[0050] Figure 25 This is a gas chromatogram of the thiamine degradation products in Example 21. Detailed Implementation
[0051] To better understand the content of this invention, the invention will be further described below with reference to specific embodiments, but the scope of protection of this invention is not limited thereto.
[0052] The thiamine degradation products prepared in the comparative examples and embodiments were analyzed by headspace-solid phase microextraction combined with gas chromatography-mass spectrometry (HS-SPME-GC-MS). After the aroma was adsorbed by the adsorption needle of the solid phase microextraction, it was desorbed at the injection port of the gas chromatograph, separated by the gas chromatograph column, and then entered the mass spectrometer. Specific procedures: Accurately weigh 0.500 g of sample into a 20 ml injection bottle; maintain the pretreatment temperature at 60 °C for 20 min, and allow adsorption for 20 min. After headspace-solid phase microextraction adsorption, insert the adsorption needle into the injection port of the gas chromatograph-mass spectrometer using an autosampler, and allow desorption for 5 min. DB-WAX capillary column (60 m × 0.25 mm, 0.25 μm); temperature program: initial temperature 40 °C, hold for 3 min, increase to 230 °C at 3 °C / min, hold for 10 min. The carrier gas was He, the constant flow rate was 1 mL / min, the injection port temperature was 250℃, the pressure was 16.087 psi, the split ratio was 5:1, and the septum purge flow rate was 5 mL / min. An electron impact ionization (EI) source was used, with an electron energy of 70 eV, a transfer line temperature of 250℃, an ion source temperature of 230℃, a quadrupole temperature of 150℃, and a mass scan range of 30-550 m / z. In the analytical results, the peak area represents the relative content of each substance in the reaction products; compared with the substance itself, the larger the peak area, the higher its concentration.
[0053] Comparative Example 1:
[0054] Thiamine hydrochloride and deionized water were added sequentially to a reactor equipped with a magnetic rotor, with a mass ratio of 1:1. The reaction mixture was reacted at 80°C for 1 hour, then cooled to obtain thiamine degradation products. The degradation products were extracted with sunflower seed oil, with a mass ratio of 1:1 to the thiamine degradation products. After further separation and drying, meat-flavored seasoning oil was obtained.
[0055] The thiamine degradation products were analyzed by HS-SPME-GC-MS: (e.g.) Figure 1 As shown in the analysis results, the total peak area of 2-methyl-3-mercaptofuran and bis(2-methyl-3-furanyl)disulfide is 1.25 × 10⁻⁶. 6 .
[0056] Comparative Example 2:
[0057] Following the method reported in Journal of Food Science, 1972, 37, 689: Thiamine hydrochloride and phosphate buffer solution (prepared from potassium dihydrogen phosphate and dipotassium hydrogen phosphate) were added sequentially to a reaction vessel equipped with a magnetic rotor. The pH was adjusted to 5.0, and the reaction was carried out at 121°C for 30 minutes. After cooling, thiamine degradation products were obtained.
[0058] The thiamine degradation products were analyzed by HS-SPME-GC-MS: (e.g.) Figure 2 As shown in the analysis results, the total peak area of 2-methyl-3-mercaptofuran and bis(2-methyl-3-furanyl)disulfide is 4.08 × 10⁻⁶. 6 .
[0059] Comparative Example 3:
[0060] Following the method reported in Journal of Food Science, 1972, 37, 689: Thiamine hydrochloride and phosphate buffer solution (prepared from potassium dihydrogen phosphate and dipotassium hydrogen phosphate) were added sequentially to a reaction vessel equipped with a magnetic rotor. The pH was adjusted to 6.0, and the reaction was carried out at 121°C for 30 minutes. After cooling, thiamine degradation products were obtained.
[0061] The thiamine degradation products were analyzed by HS-SPME-GC-MS: (e.g.) Figure 3 As shown in the analysis results, the total peak area of 2-methyl-3-mercaptofuran and bis(2-methyl-3-furanyl)disulfide is 1.10 × 10⁻⁶. 6 .
[0062] Comparative Example 4:
[0063] Following the method reported in Journal of Food Science, 1972, 37, 689: Thiamine hydrochloride and phosphate buffer solution (prepared from potassium dihydrogen phosphate and dipotassium hydrogen phosphate) were added sequentially to a reaction vessel equipped with a magnetic rotor. The pH was adjusted to 7.0, and the reaction was carried out at 120°C for 30 minutes. After cooling, thiamine degradation products were obtained.
[0064] The thiamine degradation products were analyzed by HS-SPME-GC-MS: (e.g.) Figure 4 As shown, the analysis results did not detect the formation of 2-methyl-3-mercaptofuran and bis(2-methyl-3-furanyl)disulfide, two meat flavor compounds.
[0065] Example 1:
[0066] Thiamine hydrochloride, sodium dihydrogen phosphate, and deionized water were added sequentially to a reaction vessel equipped with a magnetic rotor. The mass ratio of thiamine sulfate, sodium dihydrogen phosphate, and deionized water was 100:4:100. The reaction was carried out at 120°C for 2 hours, and then cooled to obtain the thiamine degradation product.
[0067] The thiamine degradation products were extracted with sunflower seed oil at a mass ratio of 1:1, and then further separated and dried to obtain meat-flavored seasoning oil.
[0068] The thiamine degradation products were analyzed by HS-SPME-GC-MS: (e.g.) Figure 5 As shown in the analysis results, the total peak area of 2-methyl-3-mercaptofuran and bis(2-methyl-3-furanyl)disulfide is 2.01 × 10⁻⁶. 8 The total content of the two meat aroma substances was 160.80 times that of the peak area of the meat aroma substances in Example 1.
[0069] Example 2:
[0070] Thiamine hydrochloride, disodium hydrogen phosphate, and deionized water were added sequentially to a reaction vessel equipped with a magnetic rotor. The mass ratio of thiamine sulfate, disodium hydrogen phosphate, and deionized water was 100:4:300. The reaction was carried out at 80°C for 1 hour, and then cooled to obtain the thiamine degradation product.
[0071] The thiamine degradation products were extracted with sunflower seed oil at a mass ratio of 1:1, and then further separated and dried to obtain meat-flavored seasoning oil.
[0072] The thiamine degradation products were analyzed by HS-SPME-GC-MS: (e.g.) Figure 6 As shown in the analysis results, the total peak area of 2-methyl-3-mercaptofuran and bis(2-methyl-3-furanyl)disulfide is 2.26 × 10⁻⁶. 7 The total content of the two meat aroma substances was 18.08 times that of the peak area of the meat aroma substances in Example 1.
[0073] Example 3:
[0074] Thiamine hydrochloride, disodium hydrogen phosphate, and deionized water were added sequentially to a reaction vessel equipped with a magnetic rotor. The mass ratio of thiamine hydrochloride, disodium hydrogen phosphate, and deionized water was 100:2:100. The reaction was carried out at 80°C for 1 hour, and then cooled to obtain the thiamine degradation product.
[0075] The thiamine degradation products were extracted with rapeseed oil at a mass ratio of 1:2. After further separation and drying, meat-flavored seasoning oil was obtained.
[0076] The thiamine degradation products were analyzed by HS-SPME-GC-MS: (e.g.) Figure 7 As shown in the analysis results, the total peak area of 2-methyl-3-mercaptofuran and bis(2-methyl-3-furanyl)disulfide is 2.56 × 10⁻⁶. 7 The total content of the two meat aroma substances was 20.48 times that of the peak area of the meat aroma substances in the control ratio.
[0077] Example 4:
[0078] Thiamine hydrochloride, potassium dihydrogen phosphate, and deionized water were added sequentially to a reaction vessel equipped with a magnetic rotor. The mass ratio of thiamine nitrate, potassium dihydrogen phosphate, and deionized water was 100:4:100. The reaction was carried out at 80°C for 1 hour, and then cooled to obtain the thiamine degradation product.
[0079] The thiamine degradation products were extracted with rice bran oil at a mass ratio of 5:2 to rice bran oil and thiamine degradation products. The mixture was then further separated and dried to obtain meat-flavored seasoning oil.
[0080] The thiamine degradation products were analyzed by HS-SPME-GC-MS: (e.g.) Figure 8 As shown in the analysis results, the total peak area of 2-methyl-3-mercaptofuran and bis(2-methyl-3-furanyl)disulfide is 4.79 × 10⁻⁶. 7 The total content of the two meat aroma substances was 38.32 times that of the peak area of the meat aroma substances in the control ratio.
[0081] Example 5:
[0082] Thiamine hydrochloride, potassium phosphate, and deionized water were added sequentially to a reaction vessel equipped with a magnetic rotor. The mass ratio of thiamine hydrochloride, potassium phosphate, and deionized water was 100:1:100. The reaction was carried out at 80°C for 1 hour, and then cooled to obtain the thiamine degradation product.
[0083] The thiamine degradation products were extracted with corn oil at a mass ratio of 10:1, and then further separated and dried to obtain meat-flavored seasoning oil.
[0084] The thiamine degradation products were analyzed by HS-SPME-GC-MS: (e.g.) Figure 9 As shown in the analysis results, the total peak area of 2-methyl-3-mercaptofuran and bis(2-methyl-3-furanyl)disulfide is 1.47 × 10⁻⁶. 7 The total content of the two meat aroma substances was 11.76 times that of the peak area of the meat aroma substances in the control ratio.
[0085] Example 6:
[0086] Thiamine hydrochloride, disodium hydrogen phosphate, and deionized water were added sequentially to a reaction vessel equipped with a magnetic rotor. The mass ratio of thiamine hydrochloride, disodium hydrogen phosphate, and deionized water was 100:4:100. The reaction was carried out at 100°C for 10 minutes, and then cooled to obtain the thiamine degradation product.
[0087] The thiamine degradation products were extracted with flaxseed oil at a mass ratio of 1:1 to the thiamine degradation products. The products were then further separated and dried to obtain meat-flavored seasoning oil.
[0088] The thiamine degradation products were analyzed by HS-SPME-GC-MS: (e.g.) Figure 10As shown in the analysis results, the total peak area of 2-methyl-3-mercaptofuran and bis(2-methyl-3-furanyl)disulfide is 2.01 × 10⁻⁶. 7 The total content of the two meat aroma compounds was 16.08 times that of the peak area of the meat aroma compounds in the control sample.
[0089] Example 7:
[0090] Thiamine hydrochloride, disodium hydrogen phosphate, and deionized water were added sequentially to a reaction vessel equipped with a magnetic rotor. The mass ratio of thiamine hydrochloride, disodium hydrogen phosphate, and deionized water was 100:6:100. The reaction was carried out at 100°C for 1 hour, and then cooled to obtain the thiamine degradation product.
[0091] The thiamine degradation products were extracted with peanut oil at a mass ratio of 3:1. After further separation and drying, meat-flavored seasoning oil was obtained.
[0092] The thiamine degradation products were analyzed by HS-SPME-GC-MS: (e.g.) Figure 11 As shown in the analysis results, the total peak area of 2-methyl-3-mercaptofuran and bis(2-methyl-3-furanyl)disulfide is 1.23 × 10⁻⁶. 7 The total content of the two meat aroma substances was 9.84 times that of the peak area of the meat aroma substances in the control ratio.
[0093] Example 8:
[0094] Thiamine hydrochloride, sodium dihydrogen phosphate, and deionized water were added sequentially to a reaction vessel equipped with a magnetic rotor. The mass ratio of thiamine hydrochloride, sodium dihydrogen phosphate, and deionized water was 100:2:100. The reaction was carried out at 100°C for 1 hour, and then cooled to obtain the thiamine degradation product.
[0095] The thiamine degradation products were extracted with soybean oil at a mass ratio of 1:1. After further separation and drying, meat-flavored seasoning oil was obtained.
[0096] The thiamine degradation products were analyzed by HS-SPME-GC-MS: (e.g.) Figure 12 As shown in the analysis results, the total peak area of 2-methyl-3-mercaptofuran and bis(2-methyl-3-furanyl)disulfide is 2.35 × 10⁻⁶. 7 The total content of the two meat aroma substances was 18.80 times that of the peak area of the meat aroma substances in the control ratio.
[0097] Example 9:
[0098] Thiamine hydrochloride, sodium dihydrogen phosphate, and deionized water were added sequentially to a reaction vessel equipped with a magnetic rotor. The mass ratio of thiamine hydrochloride, sodium dihydrogen phosphate, and deionized water was 100:4:100. The reaction was carried out at 100°C for 2 hours, and then cooled to obtain the thiamine degradation product.
[0099] The thiamine degradation product was extracted with caprylic / capric triglyceride at a mass ratio of 1:1 to the thiamine degradation product. The product was then further separated and dried to obtain meat-flavored seasoning oil.
[0100] The thiamine degradation products were analyzed by HS-SPME-GC-MS: (e.g.) Figure 13 As shown in the analysis results, the total peak area of 2-methyl-3-mercaptofuran and bis(2-methyl-3-furanyl)disulfide is 4.70 × 10⁻⁶. 7 The total content of the two meat aroma compounds was 37.60 times that of the peak area of the meat aroma compounds in the control sample.
[0101] Example 10:
[0102] Thiamine hydrochloride, potassium dihydrogen phosphate, and deionized water were added sequentially to a reactor equipped with a magnetic rotor. The mass ratio of thiamine hydrochloride, potassium dihydrogen phosphate, and deionized water was 100:4:100. The reaction was carried out at 100°C for 2.5 hours, and then cooled to obtain the thiamine degradation product.
[0103] The thiamine degradation products were extracted with sunflower seed oil at a mass ratio of 1:1, and then further separated and dried to obtain meat-flavored seasoning oil.
[0104] The thiamine degradation products were analyzed by HS-SPME-GC-MS: (e.g.) Figure 14 As shown in the analysis results, the total peak area of 2-methyl-3-mercaptofuran and bis(2-methyl-3-furanyl)disulfide is 8.85 × 10⁻⁶. 7 The total content of the two meat aroma substances was 70.80 times that of the peak area of the meat aroma substances in the control ratio.
[0105] Example 11:
[0106] Thiamine hydrochloride, potassium phosphate, and deionized water were added sequentially to a reactor equipped with a magnetic rotor. The mass ratio of thiamine hydrochloride, potassium phosphate, and deionized water was 100:4:100. The reaction was carried out at 100°C for 3 hours, and then cooled to obtain the thiamine degradation product.
[0107] The thiamine degradation products were extracted with sunflower seed oil at a mass ratio of 1:1, and then further separated and dried to obtain meat-flavored seasoning oil.
[0108] The thiamine degradation products were analyzed by HS-SPME-GC-MS: (e.g.) Figure 15 As shown in the analysis results, the total peak area of 2-methyl-3-mercaptofuran and bis(2-methyl-3-furanyl)disulfide is 1.14 × 10⁻⁶. 7 The total content of the two meat aroma substances was 9.12 times that of the peak area of the meat aroma substances in the control ratio.
[0109] Example 12:
[0110] Thiamine hydrochloride, sodium phosphate, and deionized water were added sequentially to a reaction vessel equipped with a magnetic rotor. The mass ratio of thiamine hydrochloride, sodium phosphate, and deionized water was 100:2:100. The reaction was carried out at 100°C for 1 hour, and then cooled to obtain the thiamine degradation product.
[0111] The thiamine degradation products were extracted with sunflower seed oil at a mass ratio of 2:1. After further separation and drying, meat-flavored seasoning oil was obtained.
[0112] The thiamine degradation products were analyzed by HS-SPME-GC-MS: (e.g.) Figure 16 As shown in the analysis results, the total peak area of 2-methyl-3-mercaptofuran and bis(2-methyl-3-furanyl)disulfide is 1.33 × 10⁻⁶. 7 The total content of the two meat aroma substances was 10.64 times that of the peak area of the meat aroma substances in the control ratio.
[0113] Example 13:
[0114] Thiamine hydrochloride, sodium phosphate, and deionized water were added sequentially to a reaction vessel equipped with a magnetic rotor. The mass ratio of thiamine hydrochloride, sodium phosphate, and deionized water was 100:4:100. The reaction was carried out at 100°C for 1 hour, and then cooled to obtain the thiamine degradation product.
[0115] The thiamine degradation products were extracted with sunflower seed oil at a mass ratio of 3:1. After further separation and drying, meat-flavored seasoning oil was obtained.
[0116] The thiamine degradation products were analyzed by HS-SPME-GC-MS: (e.g.) Figure 17 As shown in the analysis results, the total peak area of 2-methyl-3-mercaptofuran and bis(2-methyl-3-furanyl)disulfide is 1.31 × 10⁻⁶. 7 The total content of the two meat aroma substances was 10.48 times that of the peak area of the meat aroma substances in the control ratio.
[0117] Example 14:
[0118] Thiamine hydrochloride, disodium hydrogen phosphate, and deionized water were added sequentially to a reactor equipped with a magnetic rotor. The mass ratio of thiamine hydrochloride, disodium hydrogen phosphate, and deionized water was 100:6:200. The reaction was carried out at 120°C for 1 hour, and then cooled to obtain the thiamine degradation product.
[0119] The thiamine degradation products were extracted with sunflower seed oil at a mass ratio of 3:1. After further separation and drying, meat-flavored seasoning oil was obtained.
[0120] The thiamine degradation products were analyzed by HS-SPME-GC-MS: (e.g.) Figure 18 As shown in the analysis results, the total peak area of 2-methyl-3-mercaptofuran and bis(2-methyl-3-furanyl)disulfide is 6.95 × 10⁻⁶. 7 The total content of the two meat aroma compounds was 55.60 times that of the peak area of the meat aroma compounds in the control ratio.
[0121] Example 15:
[0122] Thiamine hydrochloride, dipotassium hydrogen phosphate, and deionized water were added sequentially to a reaction vessel equipped with a magnetic rotor. The mass ratio of thiamine hydrochloride, dipotassium hydrogen phosphate, and deionized water was 100:2:100. The reaction was carried out at 120°C for 1 hour, and then cooled to obtain the thiamine degradation product.
[0123] The thiamine degradation products were extracted with sunflower seed oil at a mass ratio of 1:1, and then further separated and dried to obtain meat-flavored seasoning oil.
[0124] The thiamine degradation products were analyzed by HS-SPME-GC-MS: (e.g.) Figure 19 As shown in the analysis results, the total peak area of 2-methyl-3-mercaptofuran and bis(2-methyl-3-furanyl)disulfide is 1.41 × 10⁻⁶. 7 The total content of the two meat aroma compounds was 11.28 times that of the peak area of the meat aroma compounds in the control sample.
[0125] Example 16:
[0126] Thiamine hydrochloride, sodium pyrophosphate, and deionized water were added sequentially to a reaction vessel equipped with a magnetic rotor. The mass ratio of thiamine hydrochloride, sodium pyrophosphate, and deionized water was 100:4:100. The reaction was carried out at 120°C for 1 hour, and then cooled to obtain the thiamine degradation product.
[0127] The thiamine degradation products were extracted with sunflower seed oil at a mass ratio of 1:1, and then further separated and dried to obtain meat-flavored seasoning oil.
[0128] The thiamine degradation products were analyzed by HS-SPME-GC-MS: (e.g.) Figure 20 As shown in the analysis results, the total peak area of 2-methyl-3-mercaptofuran and bis(2-methyl-3-furanyl)disulfide is 1.34 × 10⁻⁶. 7 The total content of the two meat aroma compounds was 10.72 times that of the peak area of the meat aroma compounds in the control sample.
[0129] Example 17:
[0130] Thiamine hydrochloride, sodium tripolyphosphate, and deionized water were added sequentially to a reaction vessel equipped with a magnetic rotor. The mass ratio of thiamine hydrochloride, sodium tripolyphosphate, and deionized water was 100:4:100. The reaction was carried out at 120°C for 1 hour, and then cooled to obtain the thiamine degradation product.
[0131] The thiamine degradation products were extracted with sunflower seed oil at a mass ratio of 1:1, and then further separated and dried to obtain meat-flavored seasoning oil.
[0132] The thiamine degradation products were analyzed by HS-SPME-GC-MS: (e.g.) Figure 21 As shown in the analysis results, the total peak area of 2-methyl-3-mercaptofuran and bis(2-methyl-3-furanyl)disulfide is 1.52 × 10⁻⁶. 7 The total content of the two meat aroma compounds was 12.16 times that of the peak area of the meat aroma compounds in the control sample.
[0133] Example 18:
[0134] Thiamine hydrochloride, sodium lactate, and deionized water were added sequentially to a reaction vessel equipped with a magnetic rotor. The mass ratio of thiamine hydrochloride, sodium lactate, and deionized water was 100:8:100. The reaction was carried out at 100°C for 1 hour, and then cooled to obtain the thiamine degradation product.
[0135] The thiamine degradation products were extracted from sunflower seed oil at a mass ratio of 1:1. After further separation and drying, meat-flavored seasoning oil was obtained.
[0136] The thiamine degradation products were analyzed by HS-SPME-GC-MS: (e.g.) Figure 22 As shown in the analysis results, the total peak area of 2-methyl-3-mercaptofuran and bis(2-methyl-3-furanyl)disulfide is 1.51 × 10⁻⁶. 7 The total content of the two meat aroma substances was 12.08 times that of the peak area of the meat aroma substances in the control ratio.
[0137] Example 19:
[0138] Thiamine hydrochloride, calcium lactate, and deionized water were added sequentially to a reaction vessel equipped with a magnetic rotor. The mass ratio of thiamine hydrochloride, calcium lactate, and deionized water was 100:4:100. The reaction was carried out at 100°C for 3 hours, and then cooled to obtain the thiamine degradation product.
[0139] The thiamine degradation products were extracted with sunflower seed oil at a mass ratio of 1:1, and then further separated and dried to obtain meat-flavored seasoning oil.
[0140] The thiamine degradation products were analyzed by HS-SPME-GC-MS: (e.g.) Figure 23 As shown in the analysis results, the total peak area of 2-methyl-3-mercaptofuran and bis(2-methyl-3-furanyl)disulfide is 4.04 × 10⁻⁶. 7 The total content of the two meat aroma substances was 32.32 times that of the peak area of the meat aroma substances in the control ratio.
[0141] Example 20:
[0142] Thiamine hydrochloride, disodium hydrogen phosphate, and glycerol were added sequentially to a reaction vessel equipped with a magnetic rotor. The mass ratio of thiamine hydrochloride, disodium hydrogen phosphate, and glycerol was 100:11:1000. The reaction was carried out at 140°C for 1 hour, and then cooled to obtain the thiamine degradation product.
[0143] The thiamine degradation products were analyzed by HS-SPME-GC-MS: (e.g.) Figure 24 As shown in the analysis results, the total peak area of 2-methyl-3-mercaptofuran and bis(2-methyl-3-furanyl)disulfide is 1.16 × 10⁻⁶. 7 The total content of the two meat aroma compounds was 9.28 times that of the peak area of the meat aroma compounds in the control ratio.
[0144] Example 21:
[0145] Thiamine hydrochloride, potassium dihydrogen phosphate, and propylene glycol were added sequentially to a reaction vessel equipped with a magnetic rotor in a mass ratio of 100:5:400. The reaction was carried out at 140°C for 1 hour, and then cooled to obtain the thiamine degradation product.
[0146] The thiamine degradation products were analyzed by HS-SPME-GC-MS: (e.g.) Figure 25 As shown in the analysis results, the total peak area of 2-methyl-3-mercaptofuran and bis(2-methyl-3-furanyl)disulfide is 1.85 × 10⁻⁶. 6 The total content of the two meat aroma compounds was 1.48 times that of the peak area of the meat aroma compounds in the control sample.
[0147] Comparative Example 5:
[0148] A meat flavoring, based on a total mass of 100% of raw materials, comprises the following components and their mass fractions: 10% hydrolyzed vegetable protein, 16% yeast powder, 3% Haitian brewed soy sauce, 30% salt, 1% xylose, 1% glucose, 3% white sugar, 20% monosodium glutamate, 1% disodium nucleotide (I+G), 0.6% ginger powder, 2% ethyl malt, 1% high-gluten wheat, 1% modified starch, 0.1% gum arabic, 1% thiamine hydrochloride, 0.04% potassium dihydrogen phosphate, 7.22% water, and 2.04% sunflower seed oil. 100g of the above raw material mixture is placed in a pressure cooker and reacted at 120℃ for 1 hour to obtain the meat flavoring.
[0149] Example 22:
[0150] A meat flavoring, based on the total mass of raw materials (100%), comprises the following components and their mass fractions: 10% hydrolyzed vegetable protein, 16% yeast powder, 3% Haitian brewed soy sauce, 30% salt, 1% xylose, 1% glucose, 3% white sugar, 20% monosodium glutamate, 1% disodium nucleotide (I+G), 0.6% ginger, 2% gluten, 1% high-gluten wheat, 1% modified starch, 0.1% gum arabic, 2.04% thiamine degradation products as described in Example 10, 2.04% sunflower seed oil, and 6.22% deionized water. 100g of the above raw material mixture is placed in a pressure cooker and reacted at 120°C for 1 hour to obtain the meat flavoring.
[0151] Example 23:
[0152] A meat flavoring, based on the total mass of raw materials (100%), comprises the following components and their mass fractions: 10% hydrolyzed vegetable protein, 16% yeast powder, 3% Haitian brewed soy sauce, 30% salt, 1% xylose, 1% glucose, 3% white sugar, 20% monosodium glutamate, 1% disodium nucleotide (I+G), 0.6% ginger powder, 2% maltose, 1% high-gluten wheat, 1% modified starch, 0.1% gum arabic, 2.04% meat flavoring oil as described in Example 10, and 8.26% water. 100g of the above raw material mixture is placed in a pressure cooker and reacted at 120°C for 1 hour to obtain the meat flavoring.
[0153] Sensory evaluation was used to assess the three flavorings obtained in Comparative Example 5, Example 22, and Example 23. Specifically, five professional evaluators evaluated and scored the sensory quality of the three flavorings on a scale of 0 to 10. The sensory evaluation score was the average of the scores from the five evaluators. The standard was the flavoring described in Comparative Example 5, with each index set to 5. If the aroma index was higher than that of the standard, the score was greater than 5; otherwise, it was less than 5. Sample preparation: 1g of the sample obtained in the comparative example or example was added to 99g of deionized water at 60°C for flavor evaluation. The specific results are shown in Table 1.
[0154] Table 1
[0155]
[0156] Note: Off-odors include the smell of hydrolyzed vegetable protein and yeast. Body and smoothness refer to the overall performance of the fragrance.
[0157] The sensory evaluation results in Table 1 show that in Comparative Example 5, the main aroma is a weak meaty aroma and a strong roasted aroma. The taste is characterized by prominent hydrolyzed vegetable protein and yeast notes, with a relatively strong bitterness. Overall, the aroma lacks richness and smoothness. In Example 22, the meaty aroma is prominent, the roasted aroma is weak, and the sweetness is stronger than in Comparative Example 5. The taste includes bitterness and yeast notes, and the overall aroma is relatively rich and smooth. In Example 23, the meaty aroma is strong, the roasted aroma is weak, and the sweetness is prominent. There is virtually no bitterness in the taste, a noticeable impact in the mouth, and slight yeast and hydrolyzed vegetable protein notes. The product is generally very rich and smooth. The comparison shows that in the three flavor preparation reactions, the equivalent amount of thiamine added is the same. Using thiamine-degraded meat flavor products or meat flavor seasoning oils can significantly enhance the meaty and sweet aromas in the reaction, reduce roasted aromas, off-flavors, and bitterness, and improve the overall richness and smoothness of the flavor.
[0158] Comparative Example 6:
[0159] A meat flavoring, based on the total mass of raw materials (100%), comprises the following components and their mass fractions: furanone 0.1%, methylcyclopentenolone (MCP) 1%, 2-methyl-3-mercaptofuran 3%, bis(2-methyl-3-mercaptofuran) disulfide 3%, 4-methyl-5-hydroxyethylthiazole 10%, anise oil 1%, 1,6-hexanedithiol 1%, and soybean oil 80.9%. The above raw materials are mixed to obtain a meat flavoring.
[0160] Example 24:
[0161] A meat flavoring, based on the total mass of raw materials (100%), comprises the following components and their mass fractions: 10% meat flavoring oil as described in Example 10, 0.1% furanone, 0.1% ethyl maltol, 1% methylcyclopentenolone (MCP), 0.5% 2-methyl-3-mercaptofuran, 0.5% bis(2-methyl-3-mercaptofuran) disulfide, 1% 4-methyl-5-hydroxyethylthiazole, 1% anise oil, 1% 1,6-hexanedithiol, and 84.8% soybean oil. The above raw materials are mixed to obtain a meat flavoring.
[0162] Sensory evaluation was used to assess the two flavorings obtained in Comparative Example 6 and Example 24. Specifically, five professional evaluators evaluated and scored the sensory quality of the three flavorings on a scale of 0 to 10. The sensory evaluation score was the average of the scores from the five evaluators. The standard was the flavoring described in Comparative Example 6, with each index set to 5. If the aroma index was higher than the standard, the score was greater than 5; otherwise, it was less than 5. Sample preparation: 0.1g of the sample was added to 100g of 60℃ deionized water for flavor evaluation. The specific results are shown in Table 2.
[0163] Table 2
[0164]
[0165] Note: Naturalness and fullness refer to the overall performance of the fragrance.
[0166] The sensory evaluation results in Table 2 show that the intensity of the meat and roasting aromas in Comparative Example 6 and Example 24 is not significantly different. However, Example 24 is relatively more mellow, full-bodied, and natural, with a sweetness. Furthermore, the amounts of 2-methyl-3-mercaptofuran and bis(2-methyl-3-mercaptofuran) disulfide in Example 24 are 16% of those in Comparative Example 6, and the amount of 4-methyl-5-hydroxyethylthiazole is only 10% of that in Comparative Example 6. This reduces the overall cost and results in a better meat flavor.
[0167] In summary, this invention provides a highly efficient method for promoting the degradation of thiamine into meat flavor compounds, and the simple extraction and separation process yields a richly flavored meat-flavored seasoning oil, which plays a significant role in reducing product costs and improving product quality, and also shows broad market prospects. The thiamine degradation products or high-concentration meat flavoring oil obtained by this invention can be directly used in the preparation of meat flavorings. Additionally, the meat flavoring oil can also be used directly as a flavoring base to enhance meat aroma and reduce costs.
[0168] In summary, the invention includes, but is not limited to, the above embodiments. Any equivalent substitutions or partial improvements made under the spirit and principles of this invention shall be considered to be within the protection scope of this invention.
Claims
1. A method for increasing the content of meat flavor compounds in thiamine degradation products, characterized in that: The method steps are as follows: Thiamine hydrochloride, sodium dihydrogen phosphate and deionized water were added sequentially to a reaction vessel with a magnetic rotor. The mass ratio of thiamine sulfate, sodium dihydrogen phosphate and deionized water was 100:4:
100. The reaction was carried out at 120°C for 2 hours and then cooled to obtain thiamine degradation products. The meat-flavoring substances are 2-methyl-3-mercaptofuran and bis(2-methyl-3-furanyl)disulfide.
2. An application of the thiamine degradation product as described in claim 1, characterized in that: The thiamine degradation product is used as a raw material for preparing meat flavoring or extracted with sunflower seed oil. The mass ratio of sunflower seed oil to thiamine degradation product is 1:
1. After separation and drying, meat flavoring oil is obtained.
Citation Information
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