CN111057617A - Method for inhibiting GEs production in vegetable oil refining and deodorizing process - Google Patents
Method for inhibiting GEs production in vegetable oil refining and deodorizing process Download PDFInfo
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Abstract
The invention discloses a method for inhibiting GEs generation in the process of refining and deodorizing vegetable oil. The inhibition of sesamol on GEs in vegetable oil is examined by measuring the content of GEs under the condition of simulating high-temperature deodorization by adding sesamol with different contents into the vegetable oil. The results show that the inhibition of sesamol to GEs increases with the addition amount, and the inhibition rate is 17.48-28.99%. The method provided by the invention has the advantages of simple flow, easily controlled process conditions, environmental friendliness, economy, safety and no toxicity, and can solve the safety problem caused by high content of GEs in the vegetable oil.
Description
Technical Field
The invention belongs to the field of vegetable oil and fat, and particularly relates to a method for inhibiting GEs generation in the process of refining and deodorizing vegetable oil.
Background
Glycidyl Ester (GEs) is an esterification product of glycidyl oil and fatty acid, GEs is a potential carcinogen, and can be hydrolyzed into gene carcinogenic glycidyl under the action of lipase in vivo after food enters a human body, and GEs is mainly formed in the refining process of edible oil and fat, especially in the high-temperature deodorization link. GEs is known to be generated mainly in oil refining process and mainly subjected to precursor substances of monoglyceride and glycerolThe content of the diglyceride, the temperature and time for deodorization and the like, so that the generation and the final content of the glycidyl ester can be reduced by reducing the content of precursor substances, optimizing refining conditions, adsorbing and removing and the like. Currently, Cheng et al found that the addition of antioxidants inhibited the formation of GEs not only by indirectly modulating lipid radical oxidation, but also by directly inhibiting the formation of cyclooxonium radical intermediates (Cheng W, Liu G, Liu X. effects of Fe)3+and Antioxidants on Glycidyl EsterFormation in Plant Oil at High Temperature and Their Influencing Mechanisms[J]Journal of Agricultural and Food Chemistry,2017,65(20). Therefore, it can be shown that the addition of the antioxidant can effectively inhibit the generation of GEs in the oil and fat refining process.
Sesamol is used as a naturally occurring oil-soluble antioxidant, the main types include sesamol, sesamolin, sesamol and sesamol, and the like, which not only has strong antioxidant effect, but also is safer and has the potential to replace artificially synthesized antioxidants (Weian pond, Yanling, the antioxidant research of sesamol lignan [ J ]. the research of Henan university Committee industry, 2011,32(5) Chenfeng incense, the research progress of sesamol lignan [ J ]. grains and grease, v.25; No.194(06):1-6.Dar AA, Arumugam N.Lignans of sesame: purifcation methods, biological activity and handbook [ J ]. Bioorganic Chemistry,2013, 50.). Wherein the sesamol is sesamol with strong antioxidation, and can greatly improve the oxidation stability of the grease. Dachtler et al determined the oxidation induction time of Sesamol-added sunflower seed oil by accelerated oxidation experiments to confirm that Sesamol can improve the oxidation stability of oils and fats (Dachtler M, Frans P, Frans S, et al on-line LC-NMR-MS chromatography of Sesame oil extracts and assessment of the anti-oxidative activity [ J ]. European journal led Science and Technology,2003,105(9): 488-496.). Hwang et al compared the antioxidant Effect of lignans and synthetic antioxidants on Soybean Oil heated at 180 ℃ and found that Sesamol has a better anti-Polymerization ability than TBHQ (Hwang H, Winkler-Moser JK, Liu SX. structural efficiency of Lignansand Sesamol Polymerization of Soybean Oil at condensing Temperature [ J ]. journal of the American Oil Chemists Society,2012,89(6): 1067-1076.). The antioxidant effect of sesamol with different concentrations on oil and fat is researched by Dongxingrong et al by using tea oil as a substrate, and the result shows that the oxidation stability of the oil and fat is better with the increase of the concentration of the sesamol (Dongxingrong, Liuyuguang, Li Benxiang, research and development of antioxidant activity of sesamol on tea oil [ J ] research and development of food, 2008,29(7): 19-21.). With the development and the detection of an inhibition mechanism of GEs, the addition of the antioxidant can effectively inhibit the production of GEs in the process of refining and deodorizing oil and fat, and sesamol serving as a natural antioxidant has strong antioxidant effect and is safer. Therefore, the research on the inhibition of the sesamol applied to GEs has very important guiding significance for expanding the application of sesamol and solving the safety problem caused by the high content of GEs in the grease.
Disclosure of Invention
In order to overcome the defects in the prior art, the invention aims to provide a method for inhibiting GEs generation in the process of refining and deodorizing vegetable oil.
The invention provides a method for safely inhibiting GEs generation in the refining and deodorizing process of vegetable oil, along with the gradual prohibition of the traditional artificially synthesized antioxidants BHT, Butylated Hydroxytoluene (BHA), TBHQ and the like due to safety problems.
The purpose of the invention is realized by at least one of the following technical solutions.
The invention provides a method for inhibiting GEs generation in the process of refining and deodorizing vegetable oil, which comprises the following steps: adding sesamol into vegetable oil, mixing well (ultrasonic-assisted dissolving) to obtain mixed solution, transferring the mixed solution into ampoule bottle, sealing the ampoule bottle with alcohol burner, heating for refining and deodorizing, and cooling to room temperature to obtain vegetable oil with GEs inhibition rate of 17.48-28.99%.
The vegetable oil with GEs inhibition rate of 5.11-28.99% can be preserved at 3-5 deg.C.
Further, in the mixed liquid, the content of the sesamol is 0.01-0.05wt% (w/w) by mass percent.
Further, the vegetable oil is one of palm oil, rice bran oil, corn oil, rapeseed oil, linseed oil, sunflower seed oil, perilla oil, sesame oil, soybean oil, peony seed oil, peanut oil, cottonseed oil and radish seed oil.
Preferably, the vegetable oil is one of palm oil, rice oil, corn oil, canola oil, linseed oil, sunflower oil, perilla oil, sesame oil, soybean oil, peony seed oil, peanut oil, cottonseed oil and radish seed oil.
Further, the temperature of the refining deodorization treatment is 215-235 ℃.
Further, the time of the refining deodorization treatment is 1.5-2.5 h.
Further, the vegetable oil is obtained by degumming, deacidification, decoloration and refining.
The method for inhibiting the generation of GEs in the refining and deodorizing process of the vegetable oil provided by the invention can be tested whether the method has effect by adding sesamol with different contents into the vegetable oil and testing the inhibition effect of the sesamol on GEs in the vegetable oil by measuring the GEs content under the condition of simulating high-temperature deodorization.
The detection method comprises the following steps:
(1) accurately weighing 0.500g of oil sample to be detected, dissolving the oil sample in a mixed solution of methyl tert-butyl ether and ethyl acetate (the volume ratio of the methyl tert-butyl ether to the ethyl acetate is 3:1), and uniformly mixing to obtain a liquid to be detected, wherein the concentration of the oil sample to be detected in the liquid to be detected is 240 mg/mL; then sucking 100 mu L of liquid to be detected by a liquid transfer gun, passing through a C18 solid phase extraction column, eluting by 2mL of methanol for 3 times to obtain an eluent, blowing the eluent to dry by nitrogen, then adding 2mL of mixed solution of normal hexane and ethyl acetate (the volume ratio of the normal hexane to the ethyl acetate is 95:4), fully whirling, vibrating and redissolving to obtain a composite solution A; passing the complex solution A through a Silica solid phase extraction column, eluting twice by using 2mL of mixed solution of normal hexane and ethyl acetate (the volume ratio of the normal hexane to the ethyl acetate is 95:4) to obtain eluent, drying by blowing nitrogen, adding 0.25mL of methanol, fully whirling, shaking and redissolving to obtain a complex solution B, transferring the complex solution B into a liquid phase bottle, and waiting for detection;
(2) the chromatographic column is ACQUITY UPLC HSS T3 ultra high performance liquid chromatographic column (1.8 μm,2.1mm × 100 mm); the mobile phase takes methanol and ultrapure water as a mobile phase A and a mobile phase B, and adopts a gradient mobile phase elution program, wherein the ratio is as follows: 0-8.20min, methanol: 90:10 of ultrapure water; 8.20-12.20min, methanol: ultra-pure water is 100: 0; 12.20-15.20min, methanol: 90:10 of ultrapure water; the column temperature is 25 ℃; the sample size was 5. mu.L. Mass spectrometry was quantified using a multiple reaction monitoring mode (MRM); an atmospheric pressure chemical ionization ion source (APCI), a positive ion monitoring mode, a probe temperature of 490 ℃, an ion source temperature of 140 ℃, a desolventizing air flow rate of 900L/h, a collision air flow rate of 0.14mL/min, a corona current of 1.4 muA, and a corona voltage of 3.4 KV;
(3) the inhibition of sesamol to GEs in palm oil was calculated as follows:
the inhibition rate of the sesamol to GEs is 5.11-28.99%.
Compared with the prior art, the invention has the following advantages and beneficial effects:
(1) according to the method provided by the invention, the generation of GEs can be inhibited by adding the natural antioxidant sesamol, and the inhibition rate of GEs is gradually improved along with the increase of the addition amount of sesamol.
(2) The method provided by the invention has the advantages of simple process and easily controlled process conditions, provides a new choice for inhibiting GEs, is green and economic, has no toxic or side effect on human, and can solve the safety problem caused by high GEs content in vegetable oil.
Drawings
FIG. 1 is a line graph showing the effect of the amount of sesamol added on the inhibition rate of GEs in a simulated oil in examples 1, 2 and 3;
FIG. 2 is a bar graph showing the effect of sesamol addition on GEs formation in MPO in example 1;
FIG. 3 is a bar graph of the effect of sesamol addition on the formation of GEs in MCO in example 2;
FIG. 4 is a bar graph of the effect of sesamol addition in example 3 on GEs formation in MRO.
Detailed Description
The following examples are presented to further illustrate the practice of the invention, but the practice and protection of the invention is not limited thereto. It is noted that the processes described below, if not specifically described in detail, are all realizable or understandable by those skilled in the art with reference to the prior art. The reagents or apparatus used are not indicated to the manufacturer, and are considered to be conventional products available by commercial purchase.
Example 1
A method for inhibiting GEs production in vegetable oil refining and deodorizing process comprises the following steps:
(1) adding sesamol: adding 1mg, 2mg, 3mg, 4mg and 5mg of sesamol into 5 parts of decolorized palm oil (MPO) respectively by using decolorized palm oil as Model oil (MPO); uniformly dispersing by ultrasonic to obtain 5 parts of model oil; in the 5 parts of model oil, the mass percent concentration of sesamol is respectively 0.01%, 0.02%, 0.03%, 0.04% and 0.05% (w/w);
(2) 3g of each of the 5 parts of model oil is placed in 5 ampoule bottles, the ampoule bottles are sealed by an alcohol blast burner, then the 5 ampoule bottles are heated at the same time for refining deodorization treatment, the temperature of the refining deodorization treatment is 215 ℃, the time of the refining deodorization treatment is 1.5h, the model oil is cooled to room temperature, 5 parts of the refined deodorization model oil is obtained, and the model oil is stored at the temperature of 3 ℃ and is to be detected; taking 3g of decolorized palm oil (MPO) without sesamol as a blank group, refining and deodorizing the blank group to obtain decolorized palm oil after blank treatment, storing at 3 deg.C, and testing.
Effect verification:
the oil samples to be tested are 5 parts of refined and deodorized model oil and blank-treated decolorized palm oil.
(1) Accurately weighing 0.500g of oil sample to be detected, dissolving the oil sample in a mixed solution of methyl tert-butyl ether and ethyl acetate (the volume ratio of the methyl tert-butyl ether to the ethyl acetate is 3:1), and uniformly mixing to obtain a liquid to be detected, wherein the concentration of the oil sample to be detected in the liquid to be detected is 240 mg/mL; then sucking 100 mu L of liquid to be detected by a liquid transfer gun, passing through a C18 solid phase extraction column, eluting by 2mL of methanol for 3 times to obtain an eluent, blowing the eluent to dry by nitrogen, then adding 2mL of mixed solution of normal hexane and ethyl acetate (the volume ratio of the normal hexane to the ethyl acetate is 95:4), fully whirling, vibrating and redissolving to obtain a composite solution A; passing the complex solution A through a Silica solid phase extraction column, eluting twice by using 2mL of mixed solution of normal hexane and ethyl acetate (the volume ratio of the normal hexane to the ethyl acetate is 95:4) to obtain eluent, drying by blowing nitrogen, adding 0.25mL of methanol, fully whirling, shaking and redissolving to obtain a complex solution B, transferring the complex solution B into a liquid phase bottle, and waiting for detection;
(2) the chromatographic column is ACQUITY UPLC HSS T3 ultra high performance liquid chromatographic column (1.8 μm,2.1mm × 100 mm); the mobile phase takes methanol and ultrapure water as a mobile phase A and a mobile phase B, and adopts a gradient mobile phase elution program, wherein the ratio is as follows: 0-8.20min, methanol: 90:10 of ultrapure water; 8.20-12.20min, methanol: ultra-pure water is 100: 0; 12.20-15.20min, methanol: 90:10 of ultrapure water; the column temperature is 25 ℃; the sample size was 5. mu.L. Mass spectrometry was quantified using a multiple reaction monitoring mode (MRM); an atmospheric pressure chemical ionization ion source (APCI), a positive ion monitoring mode, a probe temperature of 490 ℃, an ion source temperature of 140 ℃, a desolventizing air flow rate of 900L/h, a collision air flow rate of 0.14mL/min, a corona current of 1.4 muA, and a corona voltage of 3.4 KV;
(3) the inhibition of sesamol to GEs in palm oil was calculated as follows:
and (4) analyzing results:
FIG. 2 is a bar graph of the effect of sesamol addition on GEs formation in MPO in example 1. As shown in FIG. 2, the GEs content generated by the MPO simulated refining deodorization process is gradually reduced with the increase of the addition amount of sesamol, which shows that the addition of sesamol can inhibit the generation of GEs during the MPO refining deodorization process;
FIG. 1 is a line graph showing the effect of the amount of sesamol added on the inhibition rate of GEs in a simulated oil in examples 1, 2 and 3; as can be seen from FIG. 1, the inhibition rate of the addition of sesamol to GEs production in MPO gradually increased, and when the addition of sesamol was 0.05%, the inhibition rate of GEs production after simulated refining and deodorization of MPO was 28.99%;
example 2
A method for inhibiting GEs production in vegetable oil refining and deodorizing process comprises the following steps:
(1) adding sesamol: adding 1mg, 2mg, 3mg, 4mg and 5mg of sesamol into 5 parts of decolorized corn oil (MCO) respectively by using the decolorized corn oil as Model oil (MCO); uniformly dispersing by ultrasonic to obtain 5 parts of model oil; in the 5 parts of model oil, the mass percent concentration of sesamol is respectively 0.01%, 0.02%, 0.03%, 0.04% and 0.05% (w/w);
(2) respectively placing 4g of the 5 parts of model oil into 5 ampoule bottles, sealing the ampoule bottles by using an alcohol blast burner, simultaneously heating the 5 ampoule bottles for refining deodorization treatment at 220 ℃ for 2h, cooling to room temperature to obtain 5 parts of refined deodorization model oil, storing at 4 ℃ to be detected; taking 4g of decolorized corn oil (MCO) without sesamol as blank group, refining and deodorizing the blank group to obtain decolorized corn oil after blank treatment, storing at 4 deg.C, and testing.
Effect verification:
the oil samples to be tested are 5 parts of refined and deodorized model oil and blank-treated decolorized corn oil respectively.
(1) Accurately weighing 1.000g of oil sample to be detected, dissolving the oil sample in a mixed solution of methyl tert-butyl ether and ethyl acetate (the volume ratio of the methyl tert-butyl ether to the ethyl acetate is 3:1), and uniformly mixing to obtain a liquid to be detected, wherein the concentration of the oil sample to be detected in the liquid to be detected is 250 mg/mL; then sucking 100 mu L of liquid to be detected by a liquid transfer gun, passing through a C18 solid phase extraction column, eluting by 2mL of methanol for 3 times to obtain an eluent, blowing the eluent to dry by nitrogen, then adding 2mL of mixed solution of normal hexane and ethyl acetate (the volume ratio of the normal hexane to the ethyl acetate is 95:5), fully whirling, shaking and redissolving to obtain a complex solution A; passing the complex solution A through a Silica solid phase extraction column, eluting twice by using 2mL of mixed solution of normal hexane and ethyl acetate (the volume ratio of the normal hexane to the ethyl acetate is 95:5) to obtain eluent, drying by blowing nitrogen, adding 0.5mL of methanol, fully whirling, shaking and redissolving to obtain a complex solution B, transferring the complex solution B into a liquid phase bottle, and waiting for detection;
(2) GEs content determination: the chromatographic column is ACQUITY UPLC HSS T3 ultra high performance liquid chromatographic column (1.8 μm,2.1mm × 100 mm); the mobile phase takes methanol and ultrapure water as a mobile phase A and a mobile phase B, and adopts a gradient mobile phase elution program, wherein the ratio is as follows: 0-8.20min, methanol: 90:10 of ultrapure water; 8.20-12.20min, methanol: ultra-pure water is 100: 0; 12.20-15.20min, methanol: 90:10 of ultrapure water; the column temperature is 30 ℃; the amount of the sample was 10. mu.L. Mass spectrometry was quantified using a multiple reaction monitoring mode (MRM); an atmospheric pressure chemical ionization ion source (APCI), a positive ion monitoring mode, a probe temperature of 500 ℃, an ion source temperature of 150 ℃, a desolventizing air flow rate of 1000L/h, a collision air flow rate of 0.15mL/min, a corona current of 1.5 muA and a corona voltage of 3.5 KV;
(3) the inhibition of sesamol to GEs in the decolorized corn oil was calculated as follows:
and (4) analyzing results:
FIG. 3 is a bar graph of the effect of sesamol addition on the formation of GEs in MCO in example 2;
as can be seen from fig. 3, as the addition amount of sesamol increases, the GEs content generated in the MCO simulated refining deodorization process gradually decreases, which indicates that the addition of sesamol can inhibit the generation of GEs in the MCO refined deodorization process;
FIG. 1 is a line graph showing the effect of the amount of sesamol added on the inhibition rate of GEs in a simulated oil in examples 1, 2 and 3; as shown in fig. 1, the suppression rate of GEs formation in MCO gradually increased with the increase of the added amount of sesamol, and the suppression rate of GEs formation after MCO was subjected to simulated refining and deodorization was 17.48% at the added amount of sesamol of 0.05%.
Example 3
A method for inhibiting GEs production in vegetable oil refining and deodorizing process comprises the following steps:
(1) adding sesamol: adding 1mg, 2mg, 3mg, 4mg and 5mg of sesamol into 5 parts of decolorized rice bran oil (MRO) respectively by using decolorized rice bran oil as Model rice bran oil (MRO); uniformly dispersing by ultrasonic to obtain 5 parts of model oil; in the 5 parts of model oil, the mass percent concentration of sesamol is respectively 0.01%, 0.02%, 0.03%, 0.04% and 0.05% (w/w);
(2) respectively placing 4g of the 5 parts of model oil into 5 ampoule bottles, sealing the ampoule bottles by using an alcohol blast burner, simultaneously heating the 5 ampoule bottles for refining deodorization treatment at 235 ℃, cooling to room temperature to obtain 5 parts of refined deodorization-treated model oil, storing at 5 ℃ to be detected; taking 4g of decolorized rice bran oil (MRO) without sesamol as blank group, refining and deodorizing the blank group to obtain decolorized rice bran oil, storing at 5 deg.C, and testing.
Effect verification:
the oil samples to be tested are 5 parts of refined and deodorized model oil and blank-treated decolorized rice bran oil respectively.
(1) Accurately weighing 1.500g of an oil sample to be detected, dissolving the oil sample in a mixed solution of methyl tert-butyl ether and ethyl acetate (the volume ratio of the methyl tert-butyl ether to the ethyl acetate is 5:1), and uniformly mixing to obtain a liquid to be detected, wherein the concentration of the oil sample to be detected in the liquid to be detected is 260 mg/mL; then absorbing 200 mu L of liquid to be detected by using a liquid transfer gun, passing through a C18 solid phase extraction column, eluting by using 4mL of methanol for 3 times to obtain an eluent, drying by using nitrogen, then adding 3mL of mixed solution of normal hexane and ethyl acetate (the volume ratio of the normal hexane to the ethyl acetate is 95:6), fully whirling, vibrating and redissolving to obtain a complex solution A; passing the complex solution A through a Silica solid phase extraction column, eluting twice by using 4mL of mixed solution of normal hexane and ethyl acetate (the volume ratio of the normal hexane to the ethyl acetate is 95:6) to obtain eluent, drying by blowing nitrogen, adding 0.5mL of methanol, fully whirling, shaking and redissolving to obtain a complex solution B, transferring the complex solution B into a liquid phase bottle, and waiting for detection;
(2) GEs content determination: the chromatographic column is ACQUITY UPLC HSS T3 ultra high performance liquid chromatographic column (1.8 μm,2.1mm × 100 mm); the mobile phase takes methanol and ultrapure water as a mobile phase A and a mobile phase B, and adopts a gradient mobile phase elution program, wherein the ratio is as follows: 0-8.20min, methanol: 90:10 of ultrapure water; 8.20-12.20min, methanol: ultra-pure water is 100: 0; 12.20-15.20min, methanol: 90:10 of ultrapure water; the column temperature is 35 ℃; the sample size was 15. mu.L. Mass spectrometry was quantified using a multiple reaction monitoring mode (MRM); an atmospheric pressure chemical ionization ion source (APCI), a positive ion monitoring mode, a probe temperature of 510 ℃, an ion source temperature of 160 ℃, a desolventizing air flow rate of 1100L/h, a collision air flow rate of 0.16mL/min, a corona current of 1.6 muA and a corona voltage of 3.6 KV;
(3) the inhibition rate of sesamol to GEs in the decolorized rice bran oil was calculated as follows:
and (4) analyzing results:
FIG. 4 is a bar graph of the effect of sesamol addition in example 3 on GEs formation in MRO.
As can be seen from fig. 4, as the addition amount of sesamol increased, the GEs content generated by the MRO simulated refining deodorization process gradually decreased, which indicates that the addition of sesamol can inhibit the generation of GEs during the MRO simulated refining deodorization process;
FIG. 1 is a line graph showing the effect of the amount of sesamol added on the inhibition rate of GEs in a simulated oil in examples 1, 2 and 3; as can be seen from FIG. 1, the inhibition rate of the additive of sesamol to GEs formation in MRO gradually increased with the increase of the additive amount of sesamol, and when the additive amount of sesamol is 0.05%, the inhibition rate of GEs formation after MRO is subjected to simulated refining deodorization can reach 19.00%;
the embodiments described above are presented to enable a person having ordinary skill in the art to make and use the invention. It will be readily apparent to those skilled in the art that various modifications can be made to these embodiments and that the method described herein can be applied to other embodiments without the necessity of inventive effort, such as the use of this method to suppress GEs produced in other oil refining deodorants. Therefore, the present invention is not limited to the above embodiments, and any equivalent changes, modifications, or evolutions made by those skilled in the art using the technical solution of the present invention are still within the scope of the technical solution of the present invention.
Claims (6)
1. A method for inhibiting GEs generation in vegetable oil refining and deodorizing process is characterized by comprising the following steps: adding sesamol into vegetable oil, mixing well to obtain mixed solution, heating, refining, and deodorizing to obtain vegetable oil with inhibition rate of GEs of 17.48-28.99%.
2. The method of claim 1, wherein the sesamol is present in an amount of 0.01 to 0.05wt% in the mixed solution.
3. The method of suppressing GEs production during refining and deodorizing of vegetable oils as claimed in claim 1, wherein the vegetable oil is one of palm oil, rice bran oil, corn oil, rapeseed oil, linseed oil, sunflower seed oil, perilla oil, sesame oil, soybean oil, peony seed oil, peanut oil, cotton seed oil and radish seed oil.
4. The method of suppressing GEs production during refining and deodorizing vegetable oil as claimed in claim 1, wherein the temperature of said refining and deodorizing treatment is 215- & 235-°C。
5. The method for suppressing GEs production during refining and deodorizing vegetable oil according to claim 1, wherein the refining and deodorizing treatment is carried out for 1.5-2.5 h.
6. The method for suppressing GEs production during refining and deodorizing of vegetable oil as claimed in claim 1, wherein the vegetable oil is obtained by degumming, deacidification, decolorization and refining.
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| CN114921287A (en) * | 2022-05-31 | 2022-08-19 | 深圳大学 | Refined oil and fat and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106929148A (en) * | 2015-12-29 | 2017-07-07 | 丰益(上海)生物技术研发中心有限公司 | The method of oil and fat refining |
| CN110358625A (en) * | 2019-08-07 | 2019-10-22 | 广州大学 | A kind of method that sesamol inhibits ethylene oxidic ester to generate during grease deodorization |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106929148A (en) * | 2015-12-29 | 2017-07-07 | 丰益(上海)生物技术研发中心有限公司 | The method of oil and fat refining |
| CN110358625A (en) * | 2019-08-07 | 2019-10-22 | 广州大学 | A kind of method that sesamol inhibits ethylene oxidic ester to generate during grease deodorization |
Cited By (1)
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| CN114921287A (en) * | 2022-05-31 | 2022-08-19 | 深圳大学 | Refined oil and fat and preparation method thereof |
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