CN111040875A - Antioxidant and preparation method and application thereof - Google Patents

Antioxidant and preparation method and application thereof Download PDF

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Publication number
CN111040875A
CN111040875A CN202010011153.1A CN202010011153A CN111040875A CN 111040875 A CN111040875 A CN 111040875A CN 202010011153 A CN202010011153 A CN 202010011153A CN 111040875 A CN111040875 A CN 111040875A
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China
Prior art keywords
antioxidant
tocopherol
diglyceride
grease
stirring
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CN202010011153.1A
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Chinese (zh)
Inventor
张维农
薛元强
齐玉堂
贺军波
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Wuhan Polytechnic University
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Wuhan Polytechnic University
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Priority to CN202010011153.1A priority Critical patent/CN111040875A/en
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    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11BPRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B5/00Preserving by using additives, e.g. anti-oxidants
    • C11B5/0021Preserving by using additives, e.g. anti-oxidants containing oxygen

Abstract

The invention discloses an antioxidant, a preparation method and application thereof. The antioxidant consists of diglyceride and tocopherol, wherein the diglyceride is sn-1, 3-palmitic acid diglyceride. The antioxidant prepared by the invention not only fully exerts the antioxidant effect of tocopherol and other beneficial effects in physiological aspects, but also has the characteristic of reducing fat absorption by diglyceride, and most importantly, the antioxidant prepared by combining tocopherol and diglyceride has better antioxidant effect than simple tocopherol, and integrates the tocopherol, the diglyceride and the antioxidant into a whole, so that the grease has the following advantages: 1. the oil is more nutritional; 2. the safety problem caused by the synthetic antioxidant is avoided; 3. the storage time of the grease is prolonged.

Description

Antioxidant and preparation method and application thereof
Technical Field
The invention belongs to the field of grease processing, and particularly relates to an antioxidant and a preparation method and application thereof.
Background
The oil and fat is an important raw material in daily consumption and food processing, is widely used for food processing, and has the effects of improving the properties of products, endowing the foods with good flavor and texture and the like. In addition, the oil itself is one of three major nutrients for human, has extremely high heat energy and has important physiological functions in human body. However, the double bonds contained in the oil and fat are easy to generate chain reaction with oxygen in the air under the action of factors such as light, heat, enzyme and the like, so that the oil and fat are oxidized and rancid, and the nutritional value, shelf life and safety of the oil and fat are greatly reduced. Therefore, techniques that effectively prevent or prolong fat oxidation have important roles and economic value.
The antioxidant can effectively prolong the induction time of the grease and prolong the storage time of the grease. Antioxidants are classified into synthetic antioxidants and natural antioxidants according to their origin. Common synthetic antioxidants include t-butylhydroquinone (TBHQ), 2, 6-di-t-butyl-4-methylphenol (BHT), Butylated Hydroxyanisole (BHA), and the like. Because the safety of the artificially synthesized antioxidant widely added into the edible oil is generally questioned, the natural antioxidant is concerned by the edible oil industry. A common natural antioxidant is VEAscorbic acid, apple polyphenol, sesamol, sterol, etc. Compared with synthetic antioxidants, natural antioxidants are safe, non-toxic, strong in oxidation resistance and beneficial to human health.
Along with the improvement of living standard of people, more and more people slowly change from the original full to good and healthy eating. Under the large theme of healthy diet, natural non-toxic antioxidants are slowly replacing synthetic antioxidants and are widely used in the grease industry.
Disclosure of Invention
The present invention has been made to solve the above problems, to retard the oxidation of fats and oils during storage, and to provide a method for enhancing V by using a diglycerideEMethod for improving oxidation stability of oil and fat by oxidation resistance and pure VECompared with the method, the product has high antioxidant activity and high nutrition.
In order to achieve the above object, a first aspect of the present invention provides an antioxidant consisting of a diglyceride which is sn-1, 3-palmitic acid diglyceride, and a tocopherol.
Preferably, the mass ratio of the diglyceride to the tocopherol is 100: 1.2-6.
Preferably, the tocopherol is α -tocopherol and/or gamma-tocopherol.
A second aspect of the present invention provides a method for preparing the above antioxidant, the method comprising:
dissolving diglyceride and tocopherol in an organic solvent, heating and stirring, and then evaporating the organic solvent through reduced pressure distillation to obtain the antioxidant.
Preferably, the preparation method comprises the following steps:
dissolving diglyceride and tocopherol in n-hexane, heating and stirring for 1.5-2.5h at 35-45 ℃, wherein the stirring speed is 500r/min, and then volatilizing the n-hexane at 35-45 ℃ through reduced pressure distillation to obtain the antioxidant.
According to a specific embodiment of the present invention, the preparation method comprises: dissolving diglyceride and tocopherol in n-hexane, heating and stirring at 40 ℃ for 2h at the stirring speed of 400r/min, and then volatilizing the n-hexane at 40 ℃ through reduced pressure distillation to obtain the antioxidant.
The third aspect of the invention provides the application of the antioxidant in the oxidation resistance of the grease, wherein the antioxidant is added into the grease and is uniformly mixed and stirred;
the addition amount of the antioxidant is 1-5 wt% relative to the grease;
the water content of the grease is 60-200 ppm.
Preferably, the mixing and stirring are carried out at 35-45 ℃, the stirring time is 4-6h, and the stirring speed is 300-500 r/min.
Preferably, the method further comprises treating the fat or oil to have a moisture content of 60 to 200 ppm.
Preferably, the oil and fat is at least one selected from rapeseed oil, soybean oil, rice bran oil and DHA algae oil.
The invention has the beneficial effects that:
the natural antioxidant tocopherol has excellent antioxidant capacity, is non-toxic and harmless, is beneficial to human health, and is an ideal antioxidant. The diglyceride is an endogenous component contained in the grease, has no toxic or harmful effect, and has a certain promotion effect on preventing the obesity of the human body by the diglyceride with a special structure. According to the invention, under a certain moisture content, the diglyceride can be combined with water to form an inverse micelle, and at the position where the inverse micelle is formed, the tocopherol and peroxide free radicals can be aggregated, so that the contact chance of the tocopherol and the peroxide free radicals is increased, the free radical scavenging capacity of the tocopherol is increased, and the oxidation of the grease is effectively inhibited.
The antioxidant prepared by the invention not only fully exerts the antioxidant effect of tocopherol and other beneficial effects in physiological aspects, but also has the characteristic of reducing fat absorption by diglyceride, and most importantly, the antioxidant prepared by combining tocopherol and diglyceride has better antioxidant effect than simple tocopherol, and integrates the tocopherol, the diglyceride and the antioxidant into a whole, so that the grease has the following advantages: 1. the oil is more nutritional; 2. the safety problem caused by the synthetic antioxidant is avoided; 3. the storage time of the grease is prolonged.
Additional features and advantages of the invention will be set forth in the detailed description which follows.
Drawings
FIG. 1 shows a simplified flow diagram of one mode of use of the antioxidant of the present invention.
Detailed Description
Preferred embodiments of the present invention will be described in more detail below. While the following describes preferred embodiments of the present invention, it should be understood that the present invention may be embodied in various forms and should not be limited by the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the scope of the invention to those skilled in the art.
FIG. 1 shows a simplified flow diagram of one mode of use of the antioxidant of the present invention. As shown in figure 1, dissolving the diacylglycerol and the tocopherol in normal hexane, stirring and desolventizing to obtain the antioxidant, and stirring the antioxidant and the oil for treatment to obtain the finished oil.
In the examples of the present invention, the antioxidant capacity of the antioxidant was determined by an oven method and a storage experiment. Accelerating and oxidizing the grease in a 60 ℃ oven, and determining induction time, wherein the longer the induction time is, the better the stability is; and stored at room temperature, and the peroxide value at 30 days (oxidized at 30 days) was measured.
In the examples of the present invention, the proportions are all weight percentages and the percentages are all weight percentages.
Example 1
Dissolving a certain amount of sn-1, 3-palmitic acid diglyceride and α -tocopherol (100:6) in n-hexane, heating and stirring at 40 ℃ for 2h at a stirring speed of 400r/min, and evaporating the solvent by reduced pressure distillation to obtain the antioxidant.
Taking a proper amount of rapeseed oil, adjusting the water content to 200ppm, adding 1% antioxidant, stirring for 5h at 40 ℃, stirring at the speed of 400r/min, and then respectively accelerating oxidation in an oven and storing at normal temperature.
Under the condition, an oven experiment shows that the induction time of the rapeseed oil is 15 days, and the peroxide value in the grease is 2.62mmol/kg when the rapeseed oil is stored for 30 days at normal temperature.
Example 2
Dissolving a certain amount of sn-1, 3-palmitic acid diglyceride and α -tocopherol (100:2) in n-hexane, heating and stirring at 40 ℃ for 2h at a stirring speed of 400r/min, and evaporating the solvent by reduced pressure distillation to obtain the antioxidant.
Taking a proper amount of rapeseed oil, adjusting the water content to 150ppm, adding 3% of antioxidant, stirring for 5 hours at 40 ℃, stirring at the speed of 400r/min, and then respectively accelerating oxidation in an oven and storing at normal temperature.
Under the condition, an oven experiment shows that the induction time of the rapeseed oil is 16 days, and the peroxide value in the grease is 2.05mmol/kg when the rapeseed oil is stored for 30 days at normal temperature.
Example 3
Dissolving a certain amount of sn-1, 3-palmitic acid diglyceride and α -tocopherol (100:1.2) in n-hexane, heating and stirring at 40 ℃ for 2h at a stirring speed of 400r/min, and evaporating the solvent by reduced pressure distillation to obtain the antioxidant.
Taking a proper amount of rapeseed oil, adjusting the water content to 60ppm, adding 5% of antioxidant, stirring for 5 hours at 40 ℃, stirring at the speed of 400r/min, and then respectively accelerating oxidation in an oven and storing at normal temperature.
Under the condition, an oven experiment shows that the induction time of the rapeseed oil is 20 days, and the peroxide value in the grease is 1.55mmol/kg when the rapeseed oil is stored for 30 days at normal temperature.
Example 4
The difference from the example 1 is that the rapeseed oil is replaced by soybean oil, the water content is adjusted to 200ppm, the preparation method and the addition amount of the antioxidant are unchanged, the rapeseed oil is stirred for 5 hours at the temperature of 40 ℃ at the stirring speed of 400r/min, and then the rapeseed oil is respectively subjected to accelerated oxidation in an oven and stored at the normal temperature.
Under the condition, an oven experiment shows that the induction time of the rapeseed oil is 15 days, and after the rapeseed oil is stored for 30 days at normal temperature, the peroxide value in the grease is 2.58 mmol/kg.
Example 5
Dissolving a certain amount of sn-1, 3-palmitic acid diglyceride and α -tocopherol (100:6) in n-hexane, heating and stirring at 40 ℃ for 2h at a stirring speed of 400r/min, and evaporating the solvent by reduced pressure distillation to obtain the antioxidant.
Taking a proper amount of rapeseed oil, adjusting the water content to 200ppm, adding 2% antioxidant, stirring for 5h at 40 ℃, stirring at the speed of 400r/min, and then respectively accelerating oxidation in an oven and storing at normal temperature.
Under the condition, an oven experiment shows that the induction time of the rapeseed oil is 22 days, and the peroxide value in the grease is 1.51mmol/kg when the rapeseed oil is stored for 30 days at normal temperature.
Example 6
Dissolving a certain amount of sn-1, 3-palmitic acid diglyceride and gamma-tocopherol (100:6) in n-hexane, heating and stirring at 40 ℃ for 2h at a stirring speed of 400r/min, and evaporating the solvent by reduced pressure distillation to obtain the antioxidant.
Taking a proper amount of rapeseed oil, adjusting the water content to 60ppm, adding 1% antioxidant, stirring for 5h at 40 ℃, stirring at the speed of 400r/min, and then respectively accelerating oxidation in an oven and storing at normal temperature.
Under the condition, an oven experiment shows that the induction time of the rapeseed oil is 16 days, and the peroxide value in the grease is 2.11mmol/kg when the rapeseed oil is stored for 30 days at normal temperature.
Comparative example 1
The difference from example 1 is that only tocopherol was added in an amount of 1% of the tocopherol contained in the antioxidant.
Under the condition, an oven experiment shows that the induction time of the rapeseed oil is 8 days, and the peroxide value in the grease is 5.52mmol/kg when the rapeseed oil is stored for 30 days at normal temperature.
Comparative example 2
The difference from example 1 is that only diglyceride was added in an amount of 1% of the amount of the diglyceride contained in the antioxidant
Under the condition, an oven experiment shows that the induction time of the rapeseed oil is 5 days, and the peroxide value in the grease is 6.54mmol/kg when the rapeseed oil is stored for 30 days at normal temperature.
Comparative example 3
The difference from example 1 is that only 1% tocopherol is added.
Under the condition, an oven experiment shows that the induction time of the rapeseed oil is 11 days, and the peroxide value in the grease is 5.04mmol/kg when the rapeseed oil is stored for 30 days at normal temperature.
Comparative example 4
The difference from example 1 is that only 1% of diglyceride was added.
Under the condition, an oven experiment shows that the induction time of the rapeseed oil is 3 days, and the peroxide value in the grease is 7.15mmol/kg when the rapeseed oil is stored for 30 days at normal temperature.
Comparative example 5
The difference from example 1 is that 6% of antioxidant is added.
Under the condition, an oven experiment shows that the induction time of the rapeseed oil is 12 days, and solids are separated out when the rapeseed oil is stored at normal temperature.
Comparative example 6
The difference from example 1 is that the water content of the fat and oil was controlled to 50 ppm.
Under the condition, an oven experiment shows that the induction time of the rapeseed oil is 6 days, and the peroxide value in the grease is 6.04mmol/kg when the rapeseed oil is stored for 30 days at normal temperature.
Comparative example 7
The difference from example 1 is that the water content of the fat and oil was controlled to 250 ppm.
Under the condition, an oven experiment shows that the induction time of the rapeseed oil is 7 days, and the peroxide value in the grease is 5.56mmol/kg when the rapeseed oil is stored for 30 days at normal temperature.
Comparative example 8
The difference from example 1 is that sn-1, 3-palmitic acid diglyceride in the antioxidant is replaced with sn-1, 3-myristic acid diglyceride.
Under the condition, an oven experiment shows that the induction time of the rapeseed oil is 8 days, and the peroxide value in the grease is 5.88mmol/kg when the rapeseed oil is stored for 30 days at normal temperature.
The test results are shown in fig. 1:
TABLE 1
Figure BDA0002357197510000081
Having described embodiments of the present invention, the foregoing description is intended to be exemplary, not exhaustive, and not limited to the embodiments disclosed. Many modifications and variations will be apparent to those of ordinary skill in the art without departing from the scope and spirit of the described embodiments.

Claims (9)

1. An antioxidant, characterized in that it consists of a diglyceride and a tocopherol, said diglyceride being sn-1, 3-palmitic acid diglyceride.
2. The antioxidant according to claim 1, wherein the mass ratio of the diglyceride to the tocopherol is 100: 1.2-6.
3. The antioxidant of claim 1, wherein the tocopherol is α -tocopherol and/or gamma-tocopherol.
4. A method for preparing the antioxidant according to any one of claims 1 to 3, characterized in that the method comprises:
dissolving diglyceride and tocopherol in an organic solvent, heating and stirring, and then evaporating the organic solvent through reduced pressure distillation to obtain the antioxidant.
5. The production method according to claim 4, wherein the production method comprises:
dissolving diglyceride and tocopherol in n-hexane, heating and stirring for 1.5-2.5h at 35-45 ℃, wherein the stirring speed is 500r/min, and then volatilizing the n-hexane at 35-45 ℃ through reduced pressure distillation to obtain the antioxidant.
6. The use of the antioxidant according to any one of claims 1 to 3 in the antioxidation of grease, characterized in that the antioxidant is added to grease, mixed and stirred uniformly;
the addition amount of the antioxidant is 1-5 wt% relative to the grease;
the water content of the grease is 60-200 ppm.
7. The use as claimed in claim 6, wherein the mixing and stirring are carried out at 35-45 ℃, the stirring time is 4-6h, and the stirring speed is 300-500 r/min.
8. The use of claim 6, further comprising treating the fat to a moisture content of 60 to 200 ppm.
9. The use according to claim 6, wherein the oil is at least one selected from the group consisting of rapeseed oil, soybean oil, rice bran oil, and DHA algal oil.
CN202010011153.1A 2020-01-06 2020-01-06 Antioxidant and preparation method and application thereof Pending CN111040875A (en)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08173035A (en) * 1994-12-22 1996-07-09 Kao Corp Stabilized tocopherol-containing oil and fat composition
JPH08173036A (en) * 1994-12-22 1996-07-09 Kao Corp Stabilized tocopherol-containing oil and fat composition
CN1582116A (en) * 2001-09-13 2005-02-16 花王株式会社 Oil composition
WO2009013757A1 (en) * 2007-07-26 2009-01-29 Frutarom Ltd. Composition for protecting oils and fat
CN101505609A (en) * 2006-08-11 2009-08-12 花王株式会社 Fat or oil composition

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08173035A (en) * 1994-12-22 1996-07-09 Kao Corp Stabilized tocopherol-containing oil and fat composition
JPH08173036A (en) * 1994-12-22 1996-07-09 Kao Corp Stabilized tocopherol-containing oil and fat composition
CN1582116A (en) * 2001-09-13 2005-02-16 花王株式会社 Oil composition
CN101505609A (en) * 2006-08-11 2009-08-12 花王株式会社 Fat or oil composition
WO2009013757A1 (en) * 2007-07-26 2009-01-29 Frutarom Ltd. Composition for protecting oils and fat

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
易建华等: "不同极性抗氧化剂对油包水乳液氧化稳定性的影响", 《现代食品科技》 *

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