An antioxidant, its preparation method and application

CN111040875BActive Publication Date: 2026-08-14WUHAN POLYTECHNIC UNIVERSITY
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2020-01-06
Publication Date
2026-08-14

AI Technical Summary

Technical Problem

然而,油脂中所含的双键在光、热及酶等因素的作用下易与空气中的氧气发生的链式反应,导致油脂氧化酸败,从而大大降低油脂的营养价值、货架期以及安全性

Benefits of technology

[0021]天然抗氧化剂生育酚具有优良的抗氧化能力,无毒无害,并且有益于人体健康,是理想的抗氧化剂。甘二酯是油脂含有的内源性成分,无毒害作用,并且特殊结构的甘二酯对于预防人体肥胖具有一定的促进作用。本发明中,在一定的水分含量下,甘二酯可以与水结合可形成反相胶束,在反相胶束形成的部位,生育酚与过氧化物自由基能够发生聚集,从而增加生育酚与过氧化物自由基接触的机会,增加生育酚清除自由基的能力,从而有效抑制油脂的氧化。

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Abstract

This invention discloses an antioxidant, its preparation method, and its application. The antioxidant is composed of diglyceride and tocopherol, wherein the diglyceride is sn-1,3-palmitoyl glycolide. The antioxidant prepared by this invention not only fully utilizes the antioxidant and other physiological benefits of tocopherol, but also possesses the fat-reducing properties of diglyceride. Most importantly, the antioxidant prepared by combining tocopherol and diglyceride has a superior antioxidant effect compared to tocopherol alone. Combining these three components gives oils the following advantages: 1. Increased nutritional value; 2. Avoidance of safety issues associated with synthetic antioxidants; 3. Extended shelf life.
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Description

Technical Field

[0001] This invention belongs to the field of oil processing, and more specifically, relates to an antioxidant, its preparation method, and its application. Background Technology

[0002] Oils and fats are essential raw materials in daily consumption and food processing, widely used to improve product properties and impart good flavor and texture to food. Furthermore, as one of the three major nutrients for humans, oils and fats are extremely high in energy and play important physiological functions in the human body. However, the double bonds in oils and fats are prone to chain reactions with oxygen in the air under the influence of light, heat, and enzymes, leading to oxidative rancidity and significantly reducing their nutritional value, shelf life, and safety. Therefore, technologies that effectively prevent or prolong fat oxidation are of significant importance and economic value.

[0003] Antioxidants can effectively prolong the induction time and shelf life of oils. Depending on their source, antioxidants are divided into synthetic antioxidants and natural antioxidants. Common synthetic antioxidants include tert-butylhydroquinone (TBHQ), 2,6-di-tert-butyl-4-methylphenol (BHT), and butylated hydroxyanisole (BHA). Due to widespread concerns about the safety of synthetic antioxidants widely added to edible oils, natural antioxidants have gained attention in the edible oil industry. Common natural antioxidants include vitamin C. E Natural antioxidants contain ascorbic acid, apple polyphenols, sesamol, sterols, etc. Compared with synthetic antioxidants, natural antioxidants are safe and non-toxic, have strong antioxidant capabilities, and are beneficial to human health.

[0004] As people's living standards improve, more and more people are shifting from simply eating enough to eating well and healthily. Under the overarching theme of healthy eating, natural and non-toxic antioxidants will gradually replace synthetic antioxidants and be widely used in the oil and fat industry. Summary of the Invention

[0005] The purpose of this invention is to solve the above-mentioned problems, delay the oxidation of oils during storage, and provide a method for enhancing vitamin C through diglycerides. E Antioxidant capacity and methods to improve the oxidative stability of lipids are different from simply using vitamin C. E In comparison, this method has higher antioxidant activity and nutritional value.

[0006] To achieve the above objectives, a first aspect of the present invention provides an antioxidant composed of a glycolide and tocopherol, wherein the glycolide is sn-1,3-palmitoyl glycolide.

[0007] As a preferred option, the mass ratio of diglyceride to tocopherol is 100:1.2-6.

[0008] As a preferred embodiment, the tocopherol is α-tocopherol and / or γ-tocopherol.

[0009] A second aspect of the present invention provides a method for preparing the above-described antioxidant, the method comprising:

[0010] Diglyceride and tocopherol were dissolved in an organic solvent, heated and stirred, and then the organic solvent was evaporated by vacuum distillation to obtain the antioxidant.

[0011] As a preferred embodiment, the preparation method includes:

[0012] Diglyceride and tocopherol were dissolved in n-hexane and heated and stirred at 35-45°C for 1.5-2.5 h at a stirring speed of 300-500 r / min. Then, the n-hexane was evaporated by vacuum distillation at 35-45°C to obtain the antioxidant.

[0013] According to a specific embodiment of the present invention, the preparation method is as follows: dissolve diglyceride and tocopherol in n-hexane, heat and stir at 40°C for 2 hours at a stirring speed of 400 r / min, and then evaporate n-hexane at 40°C by vacuum distillation to obtain the antioxidant.

[0014] A third aspect of the present invention provides the application of the above-mentioned antioxidant in the anti-oxidation of oils and fats, wherein the antioxidant is added to the oil and fats and mixed and stirred evenly;

[0015] The amount of antioxidant added relative to the oil is 1-5 wt%;

[0016] The moisture content of the oil is 60-200 ppm.

[0017] As a preferred option, mixing is carried out at 35-45℃ for 4-6 hours at a speed of 300-500 r / min.

[0018] As a preferred option, the oil is also treated to reduce its moisture content to 60-200 ppm.

[0019] As a preferred embodiment, the oil is selected from at least one of rapeseed oil, soybean oil, rice bran oil, and DHA algal oil.

[0020] The beneficial effects of this invention are:

[0021] Tocopherol, a natural antioxidant, possesses excellent antioxidant capabilities, is non-toxic and harmless, and beneficial to human health, making it an ideal antioxidant. Diglycerides are endogenous components found in oils and fats, have no toxic effects, and their unique structure can promote the prevention of obesity. In this invention, under certain moisture content, diglycerides can combine with water to form reverse micelles. At the sites of reverse micelle formation, tocopherol and peroxide free radicals can aggregate, thereby increasing the contact opportunity between tocopherol and peroxide free radicals, enhancing tocopherol's ability to scavenge free radicals, and thus effectively inhibiting the oxidation of oils and fats.

[0022] The antioxidant prepared by this invention not only fully utilizes the antioxidant and other physiological benefits of tocopherol, but also combines the characteristics of diglycerides in reducing fat absorption. Most importantly, the antioxidant prepared by combining tocopherol with diglycerides has a better antioxidant effect than tocopherol alone. Combining the three gives the oils the following advantages: 1. The oils are more nutritious; 2. Safety issues associated with synthetic antioxidants are avoided; 3. The storage time of the oils is extended.

[0023] Other features and advantages of the present invention will be described in detail in the following detailed description section. Attached Figure Description

[0024] Figure 1 A simplified flowchart illustrating one application method of the antioxidant of the present invention is shown. Detailed Implementation

[0025] Preferred embodiments of the invention will now be described in more detail. While preferred embodiments of the invention are described below, it should be understood that the invention can be implemented in various forms and should not be limited to the embodiments set forth herein. Rather, these embodiments are provided so that the invention will be thorough and complete, and will fully convey the scope of the invention to those skilled in the art.

[0026] Figure 1 A simplified flowchart illustrating one application method of the antioxidant of the present invention is shown. Figure 1 As shown, firstly, diglycerides and tocopherols are dissolved in hexane, and after stirring and desolventizing, an antioxidant is obtained. Then, the antioxidant is stirred with oil for further processing to obtain the finished oil.

[0027] In this embodiment of the invention, the antioxidant capacity of the antioxidant was determined by oven drying and storage experiments. The oil was accelerated to oxidation in a 60°C oven to determine the induction time; a longer induction time resulted in better stability. The oil was then stored at room temperature, and the peroxide value was measured after 30 days (after which the oil had already oxidized).

[0028] In the embodiments of this invention, the proportions refer to weight ratios, and the % refers to weight percentages.

[0029] Example 1

[0030] A certain amount of sn-1,3-palmitoyl glycolide and α-tocopherol (100:6) were dissolved in n-hexane, heated and stirred at 40°C for 2 hours at a stirring speed of 400 r / min, and then the solvent was evaporated by vacuum distillation to obtain the antioxidant.

[0031] Take an appropriate amount of rapeseed oil, adjust the moisture content to 200ppm, add 1% antioxidant, stir at 40℃ for 5h at a stirring speed of 400r / min, and then accelerate oxidation in an oven and store at room temperature.

[0032] Under these conditions, oven experiments showed that the induction time for rapeseed oil was 15 days, and the peroxide value in the oil was 2.62 mmol / kg after 30 days of storage at room temperature.

[0033] Example 2

[0034] A certain amount of sn-1,3-palmitoyl glycolide and α-tocopherol (100:2) were dissolved in n-hexane, heated and stirred at 40°C for 2 hours at a stirring speed of 400 r / min, and then the solvent was evaporated by vacuum distillation to obtain the antioxidant.

[0035] Take an appropriate amount of rapeseed oil, adjust the moisture content to 150ppm, add 3% antioxidant, stir at 40℃ for 5h at a stirring speed of 400r / min, and then accelerate oxidation in an oven and store at room temperature.

[0036] Under these conditions, oven experiments showed that the induction time for rapeseed oil was 16 days, and the peroxide value in the oil was 2.05 mmol / kg after 30 days of storage at room temperature.

[0037] Example 3

[0038] A certain amount of sn-1,3-palmitoyl glycolide and α-tocopherol (100:1.2) were dissolved in n-hexane, heated and stirred at 40°C for 2 hours at a stirring speed of 400 r / min, and then the solvent was evaporated by vacuum distillation to obtain the antioxidant.

[0039] Take an appropriate amount of rapeseed oil, adjust the moisture content to 60ppm, add 5% antioxidant, stir at 40℃ for 5h at a stirring speed of 400r / min, and then accelerate oxidation in an oven and store at room temperature.

[0040] Under these conditions, oven experiments showed that the induction time for rapeseed oil was 20 days, and the peroxide value in the oil was 1.55 mmol / kg after 30 days of storage at room temperature.

[0041] Example 4

[0042] The difference from Example 1 is that rapeseed oil was replaced with soybean oil, the moisture content was adjusted to 200 ppm, the preparation method and amount of antioxidant remained the same, and the mixture was stirred at 40°C for 5 hours at a stirring speed of 400 r / min. Then, the mixture was accelerated to oxidation in an oven and stored at room temperature.

[0043] Under these conditions, oven experiments showed that the induction time for rapeseed oil was 15 days, and after 30 days of storage at room temperature, the peroxide value in the oil was 2.58 mmol / kg.

[0044] Example 5

[0045] A certain amount of sn-1,3-palmitoyl glycolide and α-tocopherol (100:6) were dissolved in n-hexane, heated and stirred at 40°C for 2 hours at a stirring speed of 400 r / min, and then the solvent was evaporated by vacuum distillation to obtain the antioxidant.

[0046] Take an appropriate amount of rapeseed oil, adjust the moisture content to 200ppm, add 2% antioxidant, stir at 40℃ for 5h at a stirring speed of 400r / min, and then accelerate oxidation in an oven and store at room temperature.

[0047] Under these conditions, oven experiments showed that the induction time for rapeseed oil was 22 days, and the peroxide value in the oil was 1.51 mmol / kg after 30 days of storage at room temperature.

[0048] Example 6

[0049] A certain amount of sn-1,3-palmitoyl glycolide and γ-tocopherol (100:6) were dissolved in n-hexane, heated and stirred at 40°C for 2 hours at a stirring speed of 400 r / min, and then the solvent was evaporated by vacuum distillation to obtain the antioxidant.

[0050] Take an appropriate amount of rapeseed oil, adjust the moisture content to 60ppm, add 1% antioxidant, stir at 40℃ for 5h at a stirring speed of 400r / min, and then accelerate oxidation in an oven and store at room temperature.

[0051] Under these conditions, oven experiments showed that the induction time for rapeseed oil was 16 days, and the peroxide value in the oil was 2.11 mmol / kg after 30 days of storage at room temperature.

[0052] Comparative Example 1

[0053] The difference from Example 1 is that only tocopherol is added, in an amount equal to the tocopherol content in 1% of the antioxidant.

[0054] Under these conditions, oven experiments showed that the induction time for rapeseed oil was 8 days, and the peroxide value in the oil was 5.52 mmol / kg after 30 days of storage at room temperature.

[0055] Comparative Example 2

[0056] The difference from Example 1 is that only diglyceride is added, in an amount equal to the diglyceride contained in 1% of the antioxidant.

[0057] Under these conditions, oven experiments showed that the induction time for rapeseed oil was 5 days, and the peroxide value in the oil was 6.54 mmol / kg after 30 days of storage at room temperature.

[0058] Comparative Example 3

[0059] The difference from Example 1 is that only 1% tocopherol was added.

[0060] Under these conditions, oven experiments showed that the induction time for rapeseed oil was 11 days, and the peroxide value in the oil was 5.04 mmol / kg after 30 days of storage at room temperature.

[0061] Comparative Example 4

[0062] The difference from Example 1 is that only 1% diglyceride was added.

[0063] Under these conditions, oven experiments showed that the induction time for rapeseed oil was 3 days, and the peroxide value in the oil was 7.15 mmol / kg after 30 days of storage at room temperature.

[0064] Comparative Example 5

[0065] The difference from Example 1 is that 6% antioxidant is added.

[0066] Under these conditions, oven experiments showed that the induction time for rapeseed oil was 12 days, and solid precipitation occurred when stored at room temperature.

[0067] Comparative Example 6

[0068] The difference from Example 1 is that the water content of the oil is controlled at 50 ppm.

[0069] Under these conditions, oven experiments showed that the induction time for rapeseed oil was 6 days, and the peroxide value in the oil was 6.04 mmol / kg after 30 days of storage at room temperature.

[0070] Comparative Example 7

[0071] The difference from Example 1 is that the water content of the oil is controlled at 250 ppm.

[0072] Under these conditions, oven experiments showed that the induction time for rapeseed oil was 7 days, and the peroxide value in the oil was 5.56 mmol / kg after 30 days of storage at room temperature.

[0073] Comparative Example 8

[0074] The difference from Example 1 is that sn-1,3-palmitoyl glycolide in the antioxidant is replaced with sn-1,3-myristoyl glycolide.

[0075] Under these conditions, oven experiments showed that the induction time for rapeseed oil was 8 days, and the peroxide value in the oil was 5.88 mmol / kg after 30 days of storage at room temperature.

[0076] Test results are as follows Figure 1 As shown:

[0077] Table 1

[0078]

[0079] The various embodiments of the present invention have been described above. These descriptions are exemplary and not exhaustive, nor are they limited to the disclosed embodiments. Many modifications and variations will be apparent to those skilled in the art without departing from the scope and spirit of the described embodiments.

Claims

1. The application of antioxidants in the anti-oxidation of oils and fats, characterized in that, The antioxidant is composed of diglyceride and tocopherol, wherein the diglyceride is sn-1,3-palmitoyl diglyceride; Add the antioxidants to the oil and mix thoroughly. The amount of antioxidant added relative to the oil is 1-5 wt%; The moisture content of the oil is 60-200 ppm.

2. The application according to claim 1, characterized in that, The mass ratio of diglyceride to tocopherol is 100:1.2-6.

3. The application according to claim 1, characterized in that, The tocopherol is α-tocopherol and / or γ-tocopherol.

4. The application according to any one of claims 1-3, characterized in that, Methods for preparing antioxidants include: The antioxidant is obtained by dissolving diglyceride and tocopherol in an organic solvent, heating and stirring, and then evaporating the organic solvent by vacuum distillation.

5. The application according to claim 4, characterized in that, The preparation method includes: Diglyceride and tocopherol were dissolved in n-hexane and heated and stirred at 35-45°C for 1.5-2.5 h at a stirring speed of 300-500 r / min. Then, the n-hexane was evaporated by vacuum distillation at 35-45°C to obtain the antioxidant.

6. The application according to claim 1, characterized in that, Mixing and stirring are carried out at 35-45℃ for 4-6 hours at a speed of 300-500 r / min.

7. The application according to claim 1, characterized in that, It also includes processing the oils to reduce their moisture content to 60-200 ppm.

8. The application according to claim 1, characterized in that, The oil is selected from at least one of rapeseed oil, soybean oil, rice bran oil, and DHA algal oil.

Citation Information

Patent Citations

  • Fat or oil composition

    CN101505609A