CN105506013A - Method for preparing duck oil diglyceride - Google Patents

Method for preparing duck oil diglyceride Download PDF

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CN105506013A
CN105506013A CN201610061434.1A CN201610061434A CN105506013A CN 105506013 A CN105506013 A CN 105506013A CN 201610061434 A CN201610061434 A CN 201610061434A CN 105506013 A CN105506013 A CN 105506013A
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duck oil
immobilized lipase
enzyme
fatty acid
lipase
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CN105506013B (en
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王宝维
贺可琳
葛文华
张名爱
岳斌
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Qingdao day food Limited by Share Ltd
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Qingdao Agricultural University
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    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12PFERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00Preparation of oxygen-containing organic compounds
    • C12P7/64Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
    • C12P7/6436Fatty acid esters
    • C12P7/6445Glycerides

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Abstract

The invention relates to a method for preparing duck oil diglyceride through catalysis of immobilized lipase. The method for preparing the duck oil diglyceride through the catalysis of the immobilized lipase comprises the following steps: firstly utilizing an alkali hydrolysis method to prepare fatty acid mixture, mixing the fatty acid mixture with glycerinum, and generating a catalytic reaction by utilizing the immobilized lipase; by utilizing an experiment of four single factors, including enzyme dosage, specific substrate, enzymolysis temperature and enzymolysis time, and response surface analysis method, optimal conditions for preparing the duck oil diglyceride from the immobilized lipase are obtained. When the duck oil diglyceride is prepared from the immobilized lipase, enzyme and product diglyceride can be completely separated, so that no enzyme residue exists in the product, the purity of the product is high, and the safety of foods is guaranteed. Furthermore, the selected immobilized lipase can be recycled and reutilized, so that the production costs are reduced, and environmental pollution is reduced. The method for preparing the duck oil diglyceride, which is provided by the invention, creates a new way for comprehensive utilization of duck oil side-products, the additional value of the duck oil can be largely increased, and the method is a green creative project with the important development value.

Description

A kind of method preparing duck oil diacylglycerol
Technical field
The invention belongs to technical field prepared by triglyceride, be specifically related to a kind of fixed lipase catalyzed method preparing duck oil diacylglycerol.
Background technology:
Polyunsaturated fatty acid (PUFA) content of duck oil is higher, and monounsaturated fatty acids (MUFA) content higher than lard, peanut oil, soya-bean oil, Semen Maydis oil, close to sweet oil.Less for the research of duck oil at present, most of duck oil uses as feed, and economic worth is lower.The present invention intends adopting and prepares triglyceride using duck oil as the catalysis of lipid acid donor, to widen the utilization ways of duck oil, improves the fatty added value produced in the duck course of processing.
Triglyceride is by the product obtained after glycerol (glycerine) and two fatty acid esterifications.It is divided into 1,3-DAG and 1,2-triglyceride, two kinds of isomer.Research shows, triglyceride (DG) has critical function in reducing blood-fat, minimizing interior fat, the increase of suppression body weight etc.This function is mainly passed through to suppress triglyceride level (TG) to be accumulated in vivo and is realized.TG is in enteron aisle, and two ends lipid acid, due to lipase effect, is 2-mono-glycerides (MG) and free fatty acids (FA) by enzymolysis, and is absorbed at intestinal epithelial cell.In intestinal epithelial cell, FA and 2-MG is synthesized rapidly TG (neutral fat) again, and as neutral fat in blood in all-around exercises, those are not just accumulated as body fat by the neutral fat as Energy harvesting.And DG be mostly all broken down into can not the 1-MG of resynthesis fat and lipid acid, because lipid acid is different from the position that glycerine combines in 1-MG and 2-MG, therefore have very big difference as neutral fat synthesis material, it is extremely slow again to synthesize to neutral fat in small intestine.Endocellular liberation fatty acid concentration uprises, and is finally broken down into water and release of carbonate dioxide by β-oxidation approach, and therefore DG improves at small intestine lipolytic and capacity usage ratio.Neutral fat after simultaneously making edible DG in blood is difficult to rise, and like this, if continue edible DG, just can reduce body fat accumulation.Infer thus, triglyceride remains the trophic function that triglyceride level has on the one hand; On the other hand, because triglyceride and triglyceride level are in the difference of human body metabolism, and the steapsase in human body is 1,3 specificity enzymes, and therefore, triglyceride has the physicochemical property and health-care effect that some triglyceride level do not have.In addition, because triglyceride has some unique physics and biochemical characteristic, make it in food, makeup, medicine etc., have wide exploitation prospect.
Up to now, the method preparing triglyceride that domestic and international domain expert explores has following several: 1) chemical method: it is produced triglyceride and has that cost is low, economical operation, easily realizes the advantage of scale production.Early stage people this method multiplex produces triglyceride.But due to reaction lack specificity, products obtained therefrom is the mixture of 1,2-triglyceride, 1,3-DAG, and ratio is generally 7:3 ~ 6:4.Therefore, this method can not predict the binding site of lipid acid in finished product usually.Although by special chemical reaction also can production structure special 1; 3-DG; but need protective material; reactions steps is numerous and diverse tediously long; and need a large amount of chemical reagent or organic solvent; seriously polluted, this is that food, pharmaceutical industries are less desirable, is also unaccommodated from the requirement of cleaner production, environmental protection.2) hydrolysis method: disclosed hydrolysed fat is produced in the method for triglyceride at present, mostly carry out (patent CN101768076A) under the condition of high temperature, high pressure, unsaturated fatty acids is easily made to be oxidized, and energy consumption is many, production cost is higher, and easily evaporation pollutes, and is unfavorable for scale operation.3) enzymolysis process: lipase-catalyzed transesterification reaction, comprises transesterification, glycerol rhizolomy, acidolysis reaction.Utilizing natural lipase as catalyst fat hydrolysis or glycerolysis synthesis DAG, becoming the preparation method of most industrial prospect because have employed efficient biological catalyst; But this enzyme thoroughly can not be separated with product (triglyceride), and product purity is low, cannot ensure food safety; In addition, this technique can not make enzyme recycle and reuse.
Therefore, invent a kind of safety, environmental protection, efficient, economic duck oil diacylglycerol preparation method, finally reach katalaze enzyme to be thoroughly separated with product (triglyceride), product remains without enzyme, the target of recyclable recycling, significant with raising value-added content of product to duck fat ecological use.
Summary of the invention:
The object of this invention is to provide a kind of preparation method of duck oil diacylglycerol, namely adopt fixed lipase catalyzed duck oil to prepare triglyceride.
Applicant determines the optimum preparating condition of enzyme-squash techniqued duck oil diacylglycerol in long-term research, by determining best preparation condition to enzyme concentration, substrate ratio (glycerine: duck oil mixed fatty acid), temperature, the screening of time, and the preparation of immobilized enzyme is optimized, thus facilitates the present invention.
The method preparing duck oil diacylglycerol of the present invention, comprises the steps:
1) preparation of mixed fatty acid:
By duck oil solution 1.5h in 87 DEG C of thermostat water baths, be then transferred to separating funnel except sub-cloud solution, in lower floor's solution, add the NaOH solution of 1mol/L, 87 DEG C of constant temperature hydrolysis, wash deglycerizin with NaCI, then be acidified to pH2 ~ 3 with the HCl of 10%, the lipid acid that release is free;
2) preparation of triglyceride:
By above-mentioned steps 1) in mixed fatty acid mix with glycerine, add immobilized lipase, be placed on constant-temperature table and carry out enzyme digestion reaction, reaction terminate after by centrifugal by enzyme-to-substrate be separated, obtain duck oil diacylglycerol.
Above-mentioned steps 2) in the mass ratio of glycerine and mixed fatty acid be 1:2.02, hydrolysis temperature is 44 DEG C, and enzymolysis time is 9.1h, and under this condition, the most fully, product purity is high, decreases the waste of starting material and the energy, is conducive to realizing green production for enzyme digestion reaction.
Wherein immobilized lipase, its preparation method is as follows:
1) FeC1 is taken in the ratio of 1.5:1 3, FeCl 2, adding concentration is in the starch milk of 40%, puts in 65 DEG C of water-baths and heats up, and being adjusted to pH value is 10, ultrasonic mixing in 65 DEG C of water-baths; Again the liquid after mixing is placed in 60 DEG C of stirred in water bath 2h, then leaves standstill and be cooled to room temperature, adjust pH to neutral, by reacted liquid 95% washing with alcohol 3 times, carry out solid-liquid separation with magnet, incline supernatant liquor, vacuum lyophilization, crosses 100 mesh sieves, obtains magnetic starch microcapsule;
2) take 1 part of magnetic starch carrier, add the genipin solution of 1% of 20 times of volumes, crosslinked 6h, product carries out solid-liquid separation, vacuum lyophilization, obtains the magnetic starch microcapsule activated;
3) by the magnetic starch microcapsule 1 part of activation, the lipase solution 3 parts of 1%, be settled to 25 times of volumes with the damping fluid that pH is 4, in 30 DEG C, under rotating speed 200r/min in shaking table oscillatory reaction 8h, vacuum lyophilization, being i.e. fixed lipase.
The present invention adopts fixed lipase catalyzed duck oil to prepare triglyceride, and thoroughly can be separated with product (triglyceride), product purity is high, and enzyme can realize repeatedly recycling and reusing; Ensure food safety, decreased environmental pollution, reduce production cost.
Accompanying drawing illustrates:
Substrate ratio and enzyme concentration interaction response face figure in Fig. 1 the present invention
Hydrolysis temperature and enzyme concentration interaction response face figure in Fig. 2 the present invention
Enzymolysis time and enzyme concentration interaction response face figure in Fig. 3 the present invention
In Fig. 4 the present invention, hydrolysis temperature and substrate are than interaction response face figure
In Fig. 5 the present invention, enzymolysis time and substrate are than interaction response face figure
Enzymolysis time and hydrolysis temperature interaction response face figure in Fig. 6 the present invention
Embodiment:
The present invention adopts alkali process hydrolysis duck oil preparation duck oil mixed fatty acid, then is mixed according to a certain percentage with mixed fatty acid by glycerine, then adds a certain amount of immobilized lipase and reacts.With the production rate of triglyceride for index, substrate ratio, enzyme concentration, reaction times and temperature of reaction are factor, design response surface experiments, filter out the optimum process condition that triglyceride prepared by enzymolysis duck oil.
In the present invention, triglyceride method prepared by enzymolysis duck oil, includes following step:
1) preparation of mixed fatty acid: beaker 200g duck oil being put into 1000mL, adding distil water, to 440mL, is placed on 1.5h in 87 DEG C of thermostat water baths.Then be transferred to separating funnel except sub-cloud, repeat above operation.Then add the NaOH solution of a certain amount of 1mol/L, 87 DEG C of constant temperature hydrolysis, wash deglycerizin with NaCI, are acidified to pH2 ~ 3 with the HCl of 10%, the lipid acid that release is free.
2) preparation of duck oil diacylglycerol: glycerine and duck oil mixed fatty acid are put in Erlenmeyer flask according to the ratio of 1:0.5 ~ 3, add the immobilized candida antarctica lipase B of 0.5% ~ 3%, then be placed on shaking table, design temperature is 30 DEG C ~ 70 DEG C, arranging the reaction times is 2 ~ 12h, after reaction terminates, by above-mentioned reaction solution centrifugal 20min in the supercentrifuge of 4000r/min, just enzyme can be separated, the supernatant liquor obtained is highly purified diglyceride mixt.Its content of diglyceride mixt high effective liquid chromatography for measuring obtained.
Below in conjunction with specific embodiment, method of the present invention is described in detail.
Embodiment 1: the preparation of duck oil diacylglycerol
Glycerine and duck oil mixed fatty acid are put in Erlenmeyer flask according to the ratio of 1:0.5 ~ 3, add the immobilized candida antarctica lipase B of 0.5% ~ 3%, then be placed on shaking table, design temperature is 30 DEG C ~ 70 DEG C, arranging the reaction times is 2 ~ 12h, after reaction terminates, by above-mentioned reaction solution centrifugal 20min in the supercentrifuge of 4000r/min, just enzyme can be separated, the supernatant liquor obtained is highly purified diglyceride mixt.Its content of diglyceride mixt high effective liquid chromatography for measuring obtained.
The optimization step of above-mentioned reaction conditions is as follows:
(1) screening of enzyme concentration: substrate ratio (glycerine: mixed fatty acid) is set to 1:2, temperature of reaction is 50 DEG C, reaction times is 10h, and enzyme concentration is respectively 0.5%, 1%, 1.5%, 2%, 2.5%, 3%, then test respectively, carried out the preliminary screening of enzyme concentration by the production rate measuring triglyceride.
(2) screening of substrate ratio: arranging enzyme concentration is 2%, temperature of reaction is 50 DEG C, reaction times is 10h, glycerine: mixed fatty acid is respectively 1:0.5,1:1,1:1.5,1:2,1:2.5,1:3, test respectively, carried out the preliminary screening of substrate ratio by the production rate measuring triglyceride.
(3) screening of hydrolysis temperature: arranging enzyme concentration is 2%, and the reaction times is 10h, substrate is than being 1:2, and temperature of reaction is respectively 30 DEG C, 40 DEG C, 50 DEG C, 60 DEG C, 70 DEG C, test respectively, carried out the preliminary screening of hydrolysis temperature by the production rate measuring triglyceride.
(4) screening of enzymolysis time: arranging enzyme concentration is 2%, substrate is than being 1:2, and temperature of reaction is 50 DEG C, and enzymolysis time is respectively 2h, 4h, 6h, 8h, 10h, 12h, tests respectively, is carried out the preliminary screening of enzymolysis time by the production rate measuring triglyceride.
(5) response surface experiments level of factor design
Table 1 response surface experiments level of factor
(6) response surface experiments and result thereof:
Table 2 response surface scheme and result
(7) Establishment and analysis of response surface regression equation: show that its equation of linear regression is as follows after test-results being analyzed by response surface analysis software designexpert8.0.5:
Y=93.27+2.33A-0.15B+2.11C+0.74D-1.07AB+0.97AC-1.48AD+1.88BC-0.52BD+0.12CD-4.38A 2-3.63B 2-3.00C 2-2.56D 2
In formula, Y represents the production rate of triglyceride, and A represents enzyme concentration, and B represents substrate ratio, and C represents hydrolysis temperature, and D represents enzymolysis time.Carry out variance analysis to above-mentioned response surface, result is as table 3
The variance analysis of table 3 response surface
As can be seen from Table 3, regression model presents extremely significantly (P<0.01), model loses and intends item is 0.0643>0.05, without significance impact, illustrate that the fitting degree of equation is better, residual error is caused by random error, model regulation suitably, available regression equation replaces the true point of test to analyze test-results, and it corrects the coefficient of determination is 0.9110, has the variability of the testing data of 91.10% can explain with this regression model.Therefore, regression equation can describe the relation between each factor and response value preferably, and the impact of each concrete test factor on response face amount is not simple linear relationship.A, C, A in each factor 2, B 2, C 2, D 2have test-results and affect (P<0.01) extremely significantly, BC has remarkably influenced (P<0.05) to test-results, and the magnitude relationship of 4 factor impacts is: A>C>D>B.
Use designexpert8.0.5 software data processing and analysis, duck oil diacylglycerol top condition is: enzyme concentration 1.65%, substrate ratio (glycerine: mixed fatty acid) is 1:2.02, hydrolysis temperature is 54 DEG C, enzymolysis time is 9.1h, and the production rate of triglyceride is 94.08% with this understanding.
Embodiment 2: triglyceride optimum process condition screening Orthogonal Rotational Regressive Tests prepared by enzymolysis duck oil
In the ratio of substrate ratio (glycerine: mixed fatty acid) 1:2.02, mixed fatty acid and glycerine are added in Erlenmeyer flask, be placed in constant-temperature table, and to set temperature of reaction be 44 DEG C, and add 1.65% immobilized candida antarctica lipase B, the reaction times is 9.1h, after reaction terminates, by enzymolysis solution centrifugal 10min in supercentrifuge, be separated by enzyme, supernatant liquor is high diglyceride mixt, middle layer is the production rate of immobilized lipase, liquid chromatography for measuring triglyceride.
Found by 5 proof tests, gained triglyceride production rate is followed successively by 93.25%, 94.09%, 93.88%, 94.22%, 94.17% under this condition, and average recoveries is 93.92%, basically identical with the result of case study on implementation 1; The above results shows that technique of the present invention has well repeatability and stability.
Embodiment 3: the preparation of immobilized lipase
(1) pre-treatment of fixation support: by HPD-800 macroporous resin soaked in absolute ethyl alcohol 12h, suction filtration, is washed till neutrality with distilled water, and vacuum-drying is to constant weight.5%HCl pickling 12h, 5%NaOH alkali cleaning 12h, is washed till neutrality, drying for standby.24h is soaked, dried for standby with pH7.5 phosphate buffer solution.
(2) fatty enzyme immobilizatio: take carrier and lipase according to the ratio of 15.3:1, be placed in Erlenmeyer flask, adds the distilled water of 30mL, and in the constant-temperature table of 34 DEG C, (rotating speed 150r/min) adsorbs 3h.The genipin adding 1% after having adsorbed is cross-linked 3.2h, postlyophilization, obtain immobilized lipase.
Adopt the candida antarctica lipase B enzyme activity fixed of this method be fixing before 92.3%, and this immobilized lipase to reuse 4 relative enzyme work be still 80.3%.And use genipin as linking agent, field of food is more suitable for compared with glutaraldehyde.
(3) immobilized lipase Stability Determination
1) thermostability of immobilized enzyme: immobilized lipase and not immobilized lipase are positioned over 1h in the thermostat water bath of 30 DEG C, 35 DEG C, 40 DEG C, 45 DEG C, 50 DEG C, 55 DEG C, 60 DEG C, 65 DEG C, 70 DEG C, 75 DEG C, 80 DEG C, put into the refrigerator and cooled of 4 DEG C immediately but afterwards, measure enzyme and live.Result shows: not immobilized lipase and immobilized lipase are more or less the same 40 DEG C of thermotolerances, after 40 DEG C, not immobilized lipase, enzyme is lived and is started to decline, immobilized lipase is lived at 50 DEG C of enzymes and is just started to decline, and shows that immobilized lipase has good thermostability compared with not immobilized.
2) stability in storage of immobilized enzyme: immobilized and not immobilized lipase is placed in 4 DEG C of refrigerators and stores, measure the enzyme after storing 2d, 4d, 6d, 8d, 10d, 12d, 14d to live, along with the prolongation of time, resolvase vigor obviously declines, but immobilized lipase enzyme after storage 14d is lived and is still kept 87.5%, illustrates that immobilized lipase has good preservation stability.
3) operational stability measures: in order to detect the operational stability of immobilized lipase, after every secondary response, all filtered by enzyme, is used for measuring enzyme again and lives after organic solvent cleaning-drying.Primary enzyme work is 100%, and after this each enzyme is lived compared with enzyme is lived for the first time, obtains relative enzyme and lives; Detected result shows, when immobilized enzyme reuses 6 times, relative enzyme work is 55%, illustrates that immobilized enzyme has good operational stability.
Embodiment 4: not immobilized lipase-catalyzed preparation duck oil diacylglycerol
Not immobilized candida antarctica lipase B catalyzing glycerol and duck oil mixed fatty acid is adopted to carry out direct esterification reaction.With enzyme concentration 1.65%, substrate ratio (glycerine: mixed fatty acid) is 1:2.02, hydrolysis temperature is 54 DEG C, enzymolysis time is 9.1h, and 5 test-results are the yield of triglyceride is 93.28%, 94.05%, 95.02%, 92.81%, 93.33%, the yield difference with insignificance of its reaction result triglyceride compared with immobilized fat; Detected result shows, not immobilized lipase in the product containing 2% ~ 3% residual, and immobilized lipase can reach 100% separation in the product, noresidue.The stability of triglyceride can be affected in product containing a certain amount of lipase, shorten its shelf-lives, and affect Product quality and safety.
Method of the present invention is on the basis of traditional enzymolysis, first alkali process hydrolysis is carried out to duck oil and prepare mixed fatty acid, then glycerine is added and immobilized lipase reacts, not only make reaction more abundant, decrease waste of raw materials, also shorten the reaction times to a certain extent, improve the production rate of production efficiency and triglyceride.Meanwhile, technique avoids the energy dissipation adopting high temperature, high-pressure process to cause, and avoids the pollution of environment that chemical method uses reagent to bring in a large number and food, realizes enzyme and product separation, recycling, belong to energy-conservation, the innovation of reduction of discharging and safe technology.Can directly apply to the further exploitation of duck oil product innovation, the scientific utilization for duck fat provides a new approach, and applying of this technology will have great society generalization value.

Claims (7)

1. prepare a method for duck oil diacylglycerol, it is characterized in that, described method comprises the steps:
1) preparation of mixed fatty acid:
Duck oil solution is processed 1.5h in 87 DEG C of thermostat water baths, then separating funnel is transferred to except sub-cloud solution, the NaOH solution of 1mol/L is added in remaining solution, 87 DEG C of constant temperature hydrolysis, deglycerizin is washed with NaCI, pH2 ~ 3 are acidified to again, the lipid acid that release is free with the HCl of 10%;
2) preparation of triglyceride:
By above-mentioned steps 1) in mixed fatty acid mix with glycerine, add immobilized lipase, be placed on constant-temperature table and carry out enzyme digestion reaction, reaction terminate after by centrifugal by enzyme-to-substrate be separated, obtain duck oil diacylglycerol.
2. the method for claim 1, is characterized in that, described step 2) in the mass ratio of glycerine and mixed fatty acid be 1:2.02.
3. the method for claim 1, is characterized in that, described step 2) in hydrolysis temperature be 44 DEG C.
4. the method for claim 1, is characterized in that, described step 2) in enzymolysis time be 9.1h.
5. the method for claim 1, is characterized in that, described step 2) in immobilized lipase, its preparation method is as follows:
1) pre-treatment of fixation support: by HPD-800 macroporous resin soaked in absolute ethyl alcohol 12h, suction filtration, is washed till neutrality with distilled water, vacuum-drying; Use 5%HCl pickling 12h again, 5%NaOH alkali cleaning 12h, is washed till neutrality, dry; 24h is soaked, dried for standby with pH7.5 phosphate buffer solution;
2) fatty enzyme immobilizatio: take macroporous resin and candida antarctica lipase B according to the ratio of 15.3:1, be placed in Erlenmeyer flask, adds the distilled water of 30mL, in the constant-temperature table of 34 DEG C, adsorb 3h; The genipin adding 1% after having adsorbed is cross-linked, postlyophilization, obtain immobilized lipase.
6. method as claimed in claim 5, is characterized in that, described step 2) in the mass ratio of macroporous resin and candida antarctica lipase B be 15.3:1.
7. method as claimed in claim 5, is characterized in that, described step 2) in 1% genipin crosslinking time be 3.2h.
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CN110151771A (en) * 2019-07-06 2019-08-23 青岛农业大学 A kind of high rheological variation 25-hydroxy-vitamin D for colitis reparation3Preparation
CN110278995A (en) * 2019-07-30 2019-09-27 青岛农业大学 A kind of low fat natural anticorrosion beef paste and preparation method thereof
CN110331139A (en) * 2019-05-24 2019-10-15 浙江工业大学 A kind of process for fixation of candida antarctica lipase B
CN111235190A (en) * 2020-01-22 2020-06-05 新疆农业大学 Horse oil rich in diglyceride and preparation method thereof
CN113826821A (en) * 2021-09-24 2021-12-24 青岛农业大学 High-stretchability low-fat non-fried instant rice noodles and preparation method thereof
CN114480360A (en) * 2021-12-14 2022-05-13 山东省农业科学院 Method for preparing diglyceride by immobilized Sn-2 lipase

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Cited By (11)

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Publication number Priority date Publication date Assignee Title
CN110331139A (en) * 2019-05-24 2019-10-15 浙江工业大学 A kind of process for fixation of candida antarctica lipase B
CN110331139B (en) * 2019-05-24 2021-08-24 浙江工业大学 Immobilization method of candida antarctica lipase B
CN110151771A (en) * 2019-07-06 2019-08-23 青岛农业大学 A kind of high rheological variation 25-hydroxy-vitamin D for colitis reparation3Preparation
CN110151771B (en) * 2019-07-06 2021-05-11 青岛农业大学 High-rheological-property 25-hydroxy vitamin D for repairing colitis3Preparation
CN110278995A (en) * 2019-07-30 2019-09-27 青岛农业大学 A kind of low fat natural anticorrosion beef paste and preparation method thereof
CN111235190A (en) * 2020-01-22 2020-06-05 新疆农业大学 Horse oil rich in diglyceride and preparation method thereof
CN111235190B (en) * 2020-01-22 2023-11-07 新疆农业大学 Horse oil rich in diglyceride and preparation method thereof
CN113826821A (en) * 2021-09-24 2021-12-24 青岛农业大学 High-stretchability low-fat non-fried instant rice noodles and preparation method thereof
CN113826821B (en) * 2021-09-24 2023-04-25 青岛农业大学 High-stretchability low-fat non-fried instant rice noodles and preparation method thereof
CN114480360A (en) * 2021-12-14 2022-05-13 山东省农业科学院 Method for preparing diglyceride by immobilized Sn-2 lipase
CN114480360B (en) * 2021-12-14 2024-03-12 山东省农业科学院 Method for preparing diglyceride by immobilized Sn-2 lipase

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