A method for reducing the content of 3-chloropropanol esters in food by radical quenching

Abstract

The present application belongs to the technical field of plant oil processing safety, and particularly relates to a method for reducing the content of 3-chloropropanol ester in food by free radical quenching. The method comprises adding a free radical quenching substance into finished product plant oil after refining, and then further high-temperature treating the oil and fat, taking the addition of synthetic polyphenol tert-butylhydroquinone (TBHQ) and a blank group (without addition) as a control. It is found that the substance can obviously inhibit the increase of the content of 3-chloropropanol ester in the oil and fat during the heat processing process, the content of 3-chloropropanol ester in the obtained edible oil is low, and the edible safety of the edible oil can be effectively ensured. The present application not only provides a new direction for the high-value utilization of natural polyphenols in the food industry, reduces the dependence on synthetic additives, but also provides scientific support for the research and development of functional edible oil (such as antioxidant blend oil rich in polyphenols), and meets the needs of consumers for healthy oil and fat.

Description

Technical Field

[0001] This invention belongs to the field of vegetable oil processing safety technology, specifically relating to a method for reducing and controlling the content of 3-chloropropanol esters in food through free radical quenching. Background Technology

[0002] Chloropropanol esters (MCPDEs) are common trace hazardous substances found in the production and processing of oils and fats, especially 3-MCPD esters. Toxicological studies have shown that 3-MCPD esters can release free 3-MCPD—a Group 2B carcinogen—through hydrolysis in the body. The European Food Safety Authority (EFSA) has set the tolerable daily intake (TDI) of 3-MCPD at 2 μg / kg body weight, and various countries have established limits for this level.

[0003] However, the phenomenon of excessive levels of 3-MCPDEs in food occurs frequently. Liu et al. sampled 145 samples of 6 kinds of edible vegetable oils collected from 11 cities in Hebei Province and found that the 3-MCPDE exposure level (P95) of high-consumption groups exceeded the TDI reference value, posing a health risk (Liu Yinping, Yun Peng, Chen Fuzun, et al. Human exposure assessment of chloropropanol esters in commercially available vegetable oils in Hebei Province [J / OL]. China Oils and Fats, 1-7 [2025-12-22]. https: / / doi.org / 10.19902 / j.cnki.zgyz.1003-7969.250238.). In addition, 3-MCPDEs were commonly detected in infant food products from Beijing, Hangzhou, Canada, the United States, Japan, Germany and other markets, and the levels were seriously exceeded. In a 2025 report, the detection rates of 3-MCPDE and 2-MCPDE in commercially available infant formula in Hangzhou were 100.0% and 82.2%, respectively, seriously affecting the growth and health of infants. Besides vegetable oils, 3-MCPDE was also detected in baked goods and grain products, with higher levels of 3-MCPDE contamination in food compared to 2-MCPDE. Therefore, in-depth research into methods for reducing and controlling 3-MCPDEs in food has become an urgent first step in addressing food safety in the processed food sector.

[0004] MCPD esters are mainly formed in high-temperature heated oil and fat systems. Their formation mechanisms have been extensively studied in recent years, and the four widely discussed and accepted mechanisms are: direct nucleophilic substitution of chloride ions, ionic intermediate mechanism, free radical intermediate mechanism, and glycidyl ester intermediate mechanism. Currently, the control of 3-MCPDEs mainly focuses on three key aspects: oil processing and oil preparation, refining process optimization, and finished oil processing. Current research primarily concentrates on controlling precursors (monoglycerides, diglycerides, triglycerides, and chloride-containing compounds) and processing conditions during oil refining, lacking mechanistic mitigation methods.

[0005] This invention aims to verify the mechanism by which 3-MCPDE is formed through free radicals under low humidity and high temperature conditions. Common free radical quenching substances were selected for detection. The results of this invention can be used to reduce the content of 3-MCPDE in edible oils and other oily foods. Summary of the Invention

[0006] Given the potential health hazards of MCPDEs and their prevalence in heat-processed foods, and considering that optimizing raw materials and processing techniques cannot reduce their content while ensuring food quality, and given that commonly used reduction measures such as adsorption and molecular distillation are difficult to apply to heat-processed foods, and considering the necessity of using their precursor substances in heat-processed foods, the purpose of this invention is to provide a method for reducing 3-chloropropanol esters in foods using free radical quenching. This method can effectively reduce the 3-chloropropanol ester content in oils and fats, thereby improving the safety and quality of edible oils and related foods, and is suitable for application in heat-processed oil and fat foods. Furthermore, the substances selected in this invention are green and safe, the raw materials are readily available, the operation is simple, and it is practical.

[0007] Secondly, while current research also explores the inhibition of 3-chloropropanol esters by adding antioxidants, most studies utilize synthetic substances such as ascorbyl palmitate (AP), tert-butylhydroquinone (TBHQ), propyl gallate (PG), and butylated hydroxyanisole (BHT), or specifically oil saponifications or endogenous components. This study will select multiple substances from the perspective of free radical quenching mechanisms, making it more applicable. Furthermore, while there are numerous studies on the control of high-risk oils (such as palm oil), and separate studies on bulk oils such as soybean oil, this invention selects two of the most commonly used oils, palm oil and soybean oil, for joint research, thus expanding the scope of application.

[0008] This invention is achieved through the following technical solution: A method for reducing and controlling the content of 3-chloropropanol esters in food by free radical quenching includes the following steps: (1) Addition and mixing of free radical quenching substances: Take the refined finished vegetable oil into a heat-resistant glass bottle, add the pre-dissolved free radical quenching substance into the vegetable oil, and mix evenly to obtain a mixed oil. (2) High-temperature treatment: The mixed oils were placed in an oven for high-temperature treatment to accelerate oxidation, simulating the formation and reduction of 3-chloropropanol esters.

[0009] Furthermore, the finished vegetable oil is one or a mixture of two of the following: soybean oil, palm oil, peanut oil, corn oil, and sunflower seed oil.

[0010] Furthermore, the amount of the free radical quenching substance added is 0.01% to 0.10% of the mass of the finished vegetable oil.

[0011] Furthermore, the free radical quenching substance is selected from one or more of natural polyphenols, amino acids and small molecule peptides, and endogenous components of plant oils.

[0012] Furthermore, the natural polyphenol is at least one of quercetin, chlorogenic acid, and gallocatechin gallate (EGCG); The amino acid and small molecule peptide are at least one of L-cysteine ​​and glutathione; The endogenous components of the plant oil are at least one of stigmasterol and tocopherol.

[0013] Furthermore, the pre-dissolution is performed using anhydrous ethanol. Specifically, the free radical quenching substance is pre-dissolved with anhydrous ethanol. The amount of anhydrous ethanol added is based on the ability to fully dissolve the free radical quenching substance. The volume of pre-dissolved anhydrous ethanol corresponding to each 350 mL of finished vegetable oil is 2.0 mL.

[0014] Furthermore, the process of achieving uniform mixing specifically involves: stirring for 5-15 minutes, followed by ultrasonic treatment at 80-120 W for 8-12 minutes.

[0015] Furthermore, the high-temperature treatment is performed at a temperature of 170~190℃ for a duration of 0.5~8 hours.

[0016] The present invention has the following advantages over the prior art: 1. The method for reducing and controlling oxidation provided by this invention involves adding a free radical quencher to refined vegetable oil and subjecting it to high-temperature treatment, thereby simulating the thermal processing of oils. The selected substance is abundant, readily available, and possesses strong antioxidant activity, enabling it to inhibit oil oxidation during food thermal processing by scavenging free radicals and interrupting chain reactions. Experiments have demonstrated that adding a free radical quencher to vegetable oil effectively reduces the generation of primary and secondary oxidation products during oil thermal processing, effectively controlling the formation of 3-chloropropanol esters in edible vegetable oils, and thus significantly reducing the 3-chloropropanol ester content in oils.

[0017] 2. The reduction and control technology provided by this invention is simple to operate, can be industrialized, and has the characteristics of low investment cost and easy industrial promotion and application. Meanwhile, currently reported blocking methods mainly rely on synthetic antioxidants, which may raise consumer concerns about safety and limit their potential industrial application. This invention, however, starts with the free radical generation mechanism of 3-chloropropanol esters to achieve highly efficient inhibition during the process. It utilizes natural products to replace artificially synthesized polyphenols, breaking through traditional screening models. Developing safe and efficient natural inhibitors of MCPDE formation through mechanism research and scientific guidance is an important direction for future research.

[0018] 3. In simulating high-temperature processes, this invention designs different high-temperature treatment times. Compared to common vegetable oil heating systems, which often simply involve heating different treatments to the same time to observe the inhibitory effect, this invention selects different stages of high-temperature treatment, corresponding to different stages of oil oxidation. This approach better reveals the correlation between oil oxidation and the reduction of 3-chloropropanol esters, aiming to establish a dynamic monitoring mechanism during the heating process.

[0019] 4. The key protection of this invention lies in the addition of different types of free radical quenchers. By controlling the epoxy onion ion free radical intermediate, the generation of 3-MCPDE during thermal processing is inhibited, thereby effectively blocking its formation pathway. Different substances in the oil system exhibit different antioxidant effects, enhancing the overall inhibitory effect, and there are no toxic side effects, which is in line with the trend of food safety development. The free radical quenchers of this invention can be derived from different natural products, such as EGCG contained in tea leaves, and can also be utilized from tea residue waste, greatly expanding the scope of application of the patent; and it is not limited to vegetable oils and edible oils, but can also be used in various baked and fried foods containing vegetable oils to reduce and control the generation of 3-chloropropanol esters. Attached Figure Description

[0020] Figure 1 It is the main fatty acid composition of soybean oil and palm oil; Figure 2 Total ion chromatogram and mass spectrum of 3-chloropropanol esters detected by GCMS; Figure 3 The results of the determination of 3-MCPDE content in vegetable oils of Examples 1-3 and Comparative Examples 1 and 3 of the present invention; Figure 4 The results of the 3-MCPDE reduction rate determination in vegetable oils of Examples 1-3 and Comparative Example 3 of this invention; Figure 5 The results of the determination of 3-MCPDE content in the vegetable oils of Examples 4-6 and Comparative Examples 2 and 4 of this invention; Figure 6The results are the determination results of the 3-MCPDE reduction rate in the vegetable oils of Examples 4-6 and Comparative Example 4 of this invention. Detailed Implementation

[0021] To further explain the present invention, the following specific embodiments are described.

[0022] Quercetin extraction: Take 2 kg of fresh red onion sample, chop it, and blend it thoroughly using a high-speed blender. Weigh 1.0 g of the sample (accurate to 0.001 g) into a 50 mL stoppered centrifuge tube, accurately add 40 mL of 95% ethanol, vortex for 5 min, sonicate at 60℃ for 120 min, and then blend at 8000 r·min. -1 Centrifuge at a speed of 5 min, collect the supernatant and filter to obtain quercetin extract for later use.

[0023] Extraction of stigmasterol: Using ethyl acetate as the extractant and soybean oil as the raw material, stigmasterol in soybean oil was extracted by ultrasound-assisted extraction at an ultrasound temperature of 50℃, an ultrasound time of 40 min, and a liquid-to-solid ratio of 1:20. After extraction, stigmasterol extract was prepared for use.

[0024] L-cysteine ​​pretreatment: Take commercially available food-grade L-cysteine ​​directly, without extraction, and set aside.

[0025] The method for reducing and controlling 3-chloropropanol esters in food includes the following steps: (1) Addition and mixing of free radical quenching substances: Take the refined finished vegetable oil into a heat-resistant glass bottle, weigh the free radical quenching substances at 0.01~0.10% of the weight of the vegetable oil, pre-dissolve the free radical quenching substances in anhydrous ethanol (2.0 mL of anhydrous ethanol for every 350 mL of vegetable oil), add the pre-dissolved quenching substances to the vegetable oil, stir for 5 min, and then sonicate at 100W for 10 min to obtain a mixed oil. (2) High temperature treatment: The mixed oil is placed in an oven for accelerated oxidation at high temperature. The oven temperature is controlled at 170~190℃ and the treatment time is 0.5~8 h. During the hot processing, samples can be taken at different time points as needed to complete the reduction and control of 3-chloropropanol ester.

[0026] I. Determination of Basic Properties of Vegetable Oils To clarify the basic characteristics of the experimental vegetable oils, the main fatty acid composition and initial oxidation index of soybean oil and palm oil were measured, providing basic data for the subsequent analysis of the 3-chloropropanol ester reduction and control effect.

[0027] 1. Determination of the main fatty acid composition in soybean oil and palm oil The fatty acid composition of soybean oil and palm oil was analyzed, and the results are shown in Table 1 below. Figure 1 As shown.

[0028] Table 1. Composition of major fatty acids in soybean oil and palm oil ; From Table 1 and Figure 1 It can be seen that eight fatty acids were identified in palm oil, of which 45.19% were saturated fatty acids and 54.81% were unsaturated fatty acids. Seven fatty acids were identified in soybean oil, of which 19.12% were saturated fatty acids and 80.88% were unsaturated fatty acids.

[0029] 2. Determination of initial oxidation index of soybean oil and palm oil The peroxide value (POV), anisidine value (PAV), acid value (AV), thiobarbituric acid value (TBA), and initial 3-chloropropanol ester (3-MCPDE) content of soybean oil and palm oil were determined respectively, and the results are shown in Table 2.

[0030] Table 2 Initial oxidation indices of soybean oil and palm oil ; The test results showed that the acid value of each group of samples was ≤ 0.35mg NaOH / g and the peroxide value was ≤ 5 mmol / kg, all of which met the national standard quality requirements.

[0031] II. GCMS Method for Determination of 3-Chloropropanol Ester Content First, the HFBI derivatives of the target compound and their corresponding internal standard derivatives were analyzed using full scan mode, such as... Figure 2 As shown, they are well separated and do not overlap. The selected qualitative ions, 3-MCPD derivatives (m / z 253, 289, 453) and d5-3-MCPD derivatives (m / z 257, 294, 453), conform to AOCS Cd 29a-13 (AOCS, Stadler R H. Monochloropropane-1,2-diol esters (MCPDEs) and glycidyl esters (GEs): an update[J]. Current Opinion in Food Science, 2015, The detection standards published in the studies (6(1):2-8.) and other studies (Sheng Qu, Zhang Han, Wan Yue, et al. Validation study on the method of determination of chloropropanol esters in edible vegetable oils and fatty foods by solid phase extraction coupled with gas chromatography-mass spectrometry [J]. Progress in Biotechnology, 2023, 13(01):22-29. DOI:10.19586 / j.2095-2341.2022.0077.) are accurate and reliable.

[0032] III. Specific Examples of 3-Chloropropanol Ester Reduction Control In the following examples, the amount of free radical quenching substance added was 0.03% of the volume of vegetable oil. An oven-accelerated oxidation experiment was used to simulate the thermal processing of oils. The high-temperature treatment temperature was 180°C, and the total treatment time was 8 h. Samples were taken at 0.5 h, 4 h, and 8 h of heating, respectively. The 3-MCPDE content was detected by the above-mentioned GCMS method, and the reduction rate was calculated. At the same time, a blank control group (without added quenching substance) and a synthetic polyphenol control group (with added TBHQ) were set up for comparison.

[0033] Example 1: A method for reducing and controlling 3-chloropropanol esters in food by free radical quenching, comprising the following steps: Take 350 mL of finished soybean oil in a heat-resistant glass bottle, add 0.03% quercetin by volume of soybean oil, wherein the quercetin is first pre-dissolved in 2.0 mL of anhydrous ethanol, and then add the pre-dissolved polyphenols and stir for 5 min. Sonicate at 100 W for 10 min to mix thoroughly to obtain mixed oil. The mixed oil is subjected to high-temperature treatment using an oven accelerated oxidation experiment at 180℃ for 8 h. Samples are taken at 0.5 h, 4 h and 8 h to obtain soybean oil after simulated heat processing.

[0034] Example 2: A method for reducing and controlling 3-chloropropanol esters in food by free radical quenching, comprising the following steps: Take 350 mL of finished soybean oil in a heat-resistant glass bottle, add L-cysteine ​​at 0.03% of the soybean oil volume, wherein the L-cysteine ​​is first pre-dissolved in 2.0 mL of anhydrous ethanol, then add the pre-dissolved polyphenols and stir for 5 min, and then sonicate at 100 W for 10 min to mix thoroughly to obtain mixed oil; use an oven accelerated oxidation experiment to subject the above mixed oil to high temperature treatment at 180℃ for 8 h, and take samples at 0.5 h, 4 h and 8 h respectively to obtain soybean oil after simulated heat processing.

[0035] Example 3: A method for reducing and controlling 3-chloropropanol esters in food by free radical quenching, comprising the following steps: Take 350 mL of finished soybean oil into a heat-resistant glass bottle, add 0.03% stigmasterol by volume of soybean oil, wherein the stigmasterol is first pre-dissolved in 2.0 mL of anhydrous ethanol, and then add the pre-dissolved polyphenols and stir for 5 min. Sonicate at 100 W for 10 min to mix thoroughly to obtain mixed oil. The mixed oil is subjected to high-temperature treatment using an oven accelerated oxidation experiment at 180℃ for 8 h. Samples are taken at 0.5 h, 4 h and 8 h to obtain soybean oil after simulated heat processing.

[0036] Example 4: A method for reducing and controlling 3-chloropropanol esters in food by free radical quenching, comprising the following steps: Take 350 mL of finished palm oil into a heat-resistant glass bottle, add 0.03% quercetin by volume of palm oil, wherein the quercetin is first pre-dissolved in 2.0 mL of anhydrous ethanol, and then add the pre-dissolved polyphenols and stir for 5 min. Sonicate at 100 W for 10 min to mix thoroughly to obtain a mixed oil. The mixed oil is subjected to high-temperature treatment using an oven accelerated oxidation experiment at 180℃ for 8 h. Samples are taken at 0.5 h, 4 h and 8 h to obtain simulated heat-processed palm oil.

[0037] Example 5: A method for reducing and controlling 3-chloropropanol esters in food by free radical quenching, comprising the following steps: Take 350 mL of finished palm oil in a heat-resistant glass bottle, add L-cysteine ​​at 0.03% of the palm oil volume, wherein the L-cysteine ​​is first pre-dissolved in 2.0 mL of anhydrous ethanol, then add the pre-dissolved polyphenols and stir for 5 min, and sonicate at 100 W for 10 min to mix thoroughly to obtain a mixed oil; use an oven accelerated oxidation experiment to subject the above mixed oil to high-temperature treatment at 180℃ for 8 h, and take samples at 0.5 h, 4 h and 8 h respectively to obtain simulated heat-processed palm oil.

[0038] Example 6: A method for reducing and controlling 3-chloropropanol esters in food by free radical quenching, comprising the following steps: Take 350 mL of finished palm oil into a heat-resistant glass bottle, add 0.03% stigmasterol by volume of palm oil, wherein the stigmasterol is first pre-dissolved in 2.0 mL of anhydrous ethanol, and then add the pre-dissolved polyphenols and stir for 5 min. Sonicate at 100 W for 10 min to mix thoroughly to obtain a mixed oil. The mixed oil is subjected to high-temperature treatment using an oven accelerated oxidation experiment. The heating temperature is 180℃ and the time is 8 h. Samples are taken at 0.5 h, 4 h and 8 h to obtain simulated heat-processed palm oil.

[0039] Comparative Example 1 A method for heat processing edible oils includes the following steps: Take 350 mL of finished soybean oil in a heat-resistant glass bottle and use an oven to accelerate oxidation. The oil is subjected to high-temperature treatment at 180℃ for 8 hours. Samples are taken at 0.5 h, 4 h and 8 h to obtain the simulated heat-processed soybean oil.

[0040] Comparative Example 2 A method for heat processing edible oils includes the following steps: Take 350 mL of finished palm oil in a heat-resistant glass bottle and use an oven to accelerate oxidation. The oil is subjected to high-temperature treatment at 180℃ for 8 hours. Samples are taken at 0.5 h, 4 h and 8 h to obtain simulated heat-processed palm oil.

[0041] Comparative Example 3 A method for reducing 3-chloropropanol esters in soybean oil using synthetic polyphenols includes the following steps: Take 350 mL of finished soybean oil in a heat-resistant glass bottle, add 0.03% of tert-butylhydroquinone (TBHQ) by volume of soybean oil, wherein TBHQ is first pre-dissolved in 2.0 mL of anhydrous ethanol, then add the pre-dissolved polyphenol and stir for 5 min, and sonicate at 100 W for 10 min to mix thoroughly to obtain mixed oil; use an oven accelerated oxidation experiment to subject the above mixed oil to high temperature treatment at 180℃ for 8 h, and take samples at 0.5 h, 4 h and 8 h respectively to obtain soybean oil after simulated heat processing.

[0042] Comparative Example 4 A method for reducing 3-chloropropanol esters in palm oil using synthetic polyphenols includes the following steps: Take 350 mL of finished palm oil into a heat-resistant glass bottle, add 0.03% of tert-butylhydroquinone (TBHQ) by volume of palm oil, wherein TBHQ is first pre-dissolved in 2.0 mL of anhydrous ethanol, then add the pre-dissolved polyphenol and stir for 5 min, and sonicate at 100 W for 10 min to mix thoroughly to obtain a mixed oil; use an oven accelerated oxidation experiment to subject the above mixed oil to high-temperature treatment at 180℃ for 8 h, and take samples at 0.5 h, 4 h and 8 h respectively to obtain simulated heat-processed palm oil.

[0043] IV. Experimental Results and Analysis The 3-MCPDE content and reduction rate of Examples 1-6 and Comparative Examples 1-4 were summarized, and the results are as follows: Figures 3-6 And as shown in Table 3-5 below.

[0044] Table 3. Changes and reduction rates of 3-chloropropanol ester content after heating at 180℃ for 0.5 h after adding free radical inhibitors. ; Table 4. Changes and reduction rates of 3-chloropropanol ester content after heating at 180℃ for 4 h after adding free radical inhibitors. ; Table 5. Changes and reduction rates of 3-chloropropanol ester content after heating at 180℃ for 8 h after adding free radical inhibitors. ; Depend on Figures 3-6 As shown in Table 3-5, adding 0.03 (w / v) of free radical quencher to the finished vegetable oil followed by high-temperature treatment effectively improved the inhibition effect of 3-chloropropanol esters compared to Comparative Examples 1 and 2, which did not contain the quencher. Examples 1-3, 4-6, and Comparative Examples 1-2 demonstrate that for different types of finished vegetable oils (soybean oil and palm oil), the addition of free radical quencher to soybean oil had a better inhibitory effect on 3-chloropropanol esters, with the inhibition rate being soybean oil > palm oil. For different types of quenchers, considering different heating times, the inhibition effect in soybean oil was: tert-butylhydroquinone (TBHQ) > quercetin > stigmasterol > L-cysteine; while in palm oil, the inhibition effect was: quercetin > tert-butylhydroquinone (TBHQ) > stigmasterol > L-cysteine.

[0045] V. Alternative Implementation Methods Alternatives of free radical quenching substances: Quercetin, L-cysteine, and stigmasterol selected in this invention can be replaced with other free radical quenching substances, such as fat-soluble tea polyphenols, modified polyphenols, tocopherols, glutathione, and other endogenous components or natural extracts of plant oils. Multiple quenching substances can also be used in combination. After combination, the reduction and control effect of 3-chloropropanol ester can be further improved. The addition amount of each quenching substance is controlled within the range of 0.01% to 0.10% of the finished edible oil mass. Alternatives for vegetable oils: The method of the present invention is not only applicable to soybean oil and palm oil, but also to all refined vegetable oil systems such as rapeseed oil, peanut oil, corn oil, and sunflower oil. The operation steps are the same as those in the above embodiments, and all can achieve effective reduction and control of 3-chloropropanol esters. Alternative application scenarios: The method of this invention is not only applicable to the thermal processing of vegetable oil itself, but can also be extended to all food processing processes containing vegetable oil, such as baked goods (biscuits, bread), fried foods (French fries, fried chicken), grain products, etc. By adding free radical quenching substances to the oil system of the food before the food is thermally processed, and then processing it according to the above mixing and processing method, the reduction and control of 3-chloropropanol esters in the food processing process can be achieved.

[0046] Substances for reducing and controlling 3-chloropropanol esters: Free radical quenchers can not only reduce and control 3-chloropropanol esters, but also inhibit 2-chloropropanol esters, glycidyl esters, and even one or more of other food heat processing hazards such as acrylamide, polycyclic aromatic hydrocarbons, and trans fatty acids. By following the above extraction and addition methods, simultaneous reduction and control can be achieved, thereby improving overall safety.

[0047] The specific embodiments described above further illustrate the purpose, technical solution, and beneficial effects of the present invention. It should be understood that the above description is only a specific embodiment of the present invention and is not intended to limit the scope of protection of the present invention. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the scope of protection of the present invention.

Claims

1. A method for reducing and controlling the content of 3-chloropropanol esters in food by free radical quenching, characterized in that, Includes the following steps: (1) Addition and mixing of free radical quenching substances: Take the refined finished vegetable oil into a heat-resistant glass bottle, add the pre-dissolved free radical quenching substance into the vegetable oil, and mix evenly to obtain a mixed oil. (2) High-temperature treatment: The mixed oils were placed in an oven for high-temperature treatment to accelerate oxidation, simulating the formation and reduction of 3-chloropropanol esters.

2. The method for reducing and controlling the content of 3-chloropropanol esters in food by free radical quenching according to claim 1, characterized in that, The finished vegetable oil is one or a mixture of two of soybean oil and palm oil.

3. The method for reducing and controlling the content of 3-chloropropanol esters in food by free radical quenching according to claim 1, characterized in that, The amount of the free radical quenching substance added is 0.01% to 0.10% of the mass of the finished vegetable oil.

4. The method for reducing and controlling the content of 3-chloropropanol esters in food by free radical quenching according to claim 1, characterized in that, The free radical quenching substance is selected from one or more of the following: natural polyphenols, amino acids and small molecule peptides, and endogenous components of plant oils.

5. The method for reducing and controlling the content of 3-chloropropanol esters in food by free radical quenching according to claim 4, characterized in that, The natural polyphenol is at least one of quercetin, chlorogenic acid, and gallic catechin gallate (EGCG); The amino acid and small molecule peptide are at least one of L-cysteine ​​and glutathione; The endogenous components of the plant oil are at least one of stigmasterol and tocopherol.

6. The method for reducing and controlling the content of 3-chloropropanol esters in food by free radical quenching according to claim 1, characterized in that, The pre-dissolution process uses anhydrous ethanol. Specifically, the free radical quenching substance is pre-dissolved in anhydrous ethanol. The amount of anhydrous ethanol added is based on the ability to fully dissolve the free radical quenching substance. The volume of pre-dissolved anhydrous ethanol corresponding to every 350 mL of finished vegetable oil is 2.0 mL.

7. The method for reducing and controlling the content of 3-chloropropanol esters in food by free radical quenching according to claim 1, characterized in that, The process of achieving uniform mixing involves stirring for 5-15 minutes, followed by ultrasonic treatment at 80-120 W for 8-12 minutes.

8. The method for reducing and controlling the content of 3-chloropropanol esters in food by free radical quenching according to claim 1, characterized in that, The high-temperature treatment is performed at a temperature of 170~190℃ for a duration of 0.5~8 hours.

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