CN104711298A - Method for preparing DAG by enzymolysis of TAG - Google Patents
Method for preparing DAG by enzymolysis of TAG Download PDFInfo
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Abstract
The invention relates to a method for preparing DAG by enzymolysis of TAG, and belongs to the technical field of preparation of DAG. The method comprises the step of adding ethanol or/and metal ions into TAG, water and candida Antarctica lipase A to form a hydrolyzed system. According to the method, through the added metal ions, the activity of the candida Antarctica lipase A can be remarkably improved, and the hydrolysis rate of TAG is increased; ethanol and the metal ions are added at the same time, the 2-site selection tendency of the candida Antarctica lipase A for TAG can be improved, reaction time can be shortened, the hydrolysis rate is increased, and amplitude is further increased; therefore, ethanol plays the effect of promoting the metal ions to increase the hydrolysis rate.
Description
Technical field
The present invention relates to a kind of method of triglyceride enzyme-squash techniqued 1,3-DAG, belong to the preparing technical field of 1,3-DAG.
Background technology
Grease is the important component part of human diet, carries as body provides energy, and improve the functions such as flavour of food products in food processing process.Along with the raising of expanding economy and living standards of the people, China resident grease intake improves day by day.And much research shows, the risk that too much can strengthen body and suffer from the metabolism syndromes such as atherosclerosis, diabetes B, hyperlipidemia, hypertension taken in by grease, serious threat body health.
1,3-DAG (DAG) is the main moiety in natural fats and oils, without significant difference between its color, energy density, smell, stability and the bioavailability in body and traditional triglyceride level (TAG).The experiment of many Dietary frequency shows, the absorption of 1,3-DAG significantly can reduce the indexs such as the blood fat of body and blood sugar, to improving blood fat and metabolism of blood glucose, promoting health and having vital role.
Textural difference between 1,3-DAG and TAG, causes its pathways metabolism to change, and is that it plays the basis of health efficacy.Steapsase in human body is sn-1 position and sn-3 position specific lipase, can only be hydrolyzed the ester bond on TAG molecule 1 position and 3.TAG molecule enters in small intestine, and the ester bond of its 1 and 3, first by steapsase selective hydrolysis, produces the free fatty acid (NEFA) of 2-monoacylglycerol ester (2-MAG) and 2 molecules.These products are combined with cholate and form chylomicron, are rapidly absorbed into intestinal epithelial cell, and are again synthesized TAG rapidly by 2-acylglycerol approach, enter lower blood circulation.Because the speed of 2-MAG approach synthesis TAG is very fast, after therefore body takes in TAG, causes postprandial lipid metabolism concentration to raise, and reach peak value at 4 hours.After 1,3-DAG enters small intestine, under the effect of steapsase, be decomposed into glycerine and NEFA, after both enter intestinal epithelial cell, again synthesize TAG by phosphatidic acid approach.Due to phosphatidic acid approach synthesis TAG speed slowly, allly not easily again synthesize TAG in vivo, therefore just can improve blood lipids metabolism.
1,2-DAG and 2,3-DAG, although be all triglyceride, both lists, in vivo after hydrolysis, all can generate 2-MAG, allly in body, also again can synthesize TAG rapidly by 2-MAG approach, therefore not possess the such health efficacy of 1,3-DAG.
Because the content of 1,3-DAG in natural fats and oils is few, therefore need by transforming existing oil resource, to obtain highly purified 1,3-DAG.Existing 1,3-DAG preparation method mainly contains following several:
1, direct esterification
Direct esterification is with lipid acid or lipid acid donor, is raw material with glycerine or glyceroyl donor, after certain proportion mixing, under the condition of micro-aqueous phase or organic solvent, utilizes 1,3-specific fat Enzyme catalyzed synthesis 1,3-DAG.Its reaction formula is as follows:
There are many patents and paper all to report at present and adopted this method can obtain highly purified 1,3-DAG, as national inventing patent " a kind of preparation method (200410015348.4) of triglyceride, national inventing patent " a kind of preparation method (20131025590.9) etc. of triglyceride.It is simple that direct esterification has reaction, can a step completes, product purity is high, is convenient to purifies and separates, reaction time short, the utilization ratio advantages of higher of relevant enzyme and instrument.
But direct esterification is difficult to realize scale operation, main exist some problem following: one is desired raw material is that free fatty acid or glycerine price are very high; Two is that this reaction is generally carried out in organic solvent environment, there is the problem of organic solvent residual.
2, glycerine solution
From existing data, glycerol rhizolomy seemingly produces the most economical method of 1,3-DAG, is also the topmost method of current industrial production.Glycerine solution reaction formula is as follows:
Also Patents is had to report glycerine solution at present, as national inventing patent " preparation method (201310199809.7) of triglyceride " and national inventing patent " intracellular lipase producing strains and application machine screening method and using method (201310183968.8) " thereof etc.
Glycerine solution has certain restricted equally, is mainly reflected in the following aspects: one is that the price of reaction substrate glycerine is relatively higher; Two is that this speed of response slowly, generally needs the time of 10h or longer could react complete; Three is that in product, 1,3-DAG purity is not high, and purge process is complicated; Four to be that 1,3-DAG prepares rate not high, and the triglyceride level of 1 molecule and the glycerine of 1 molecule, can only generate 1,3-DAG of 1 molecule.
3, direct hydrolysis method
Refer to TAG to be raw material, under the effect with 2 acyl hydrolase proneness lipase, direct part hydrolysis generation 1,3-DAG and NEFA.Antarctic candidia lipase A(CAL-A,
candida Antarcticalipases-A) be enzyme the highest to triglyceride level 2 acyl hydrolase proneness in all lipase; May be used for preparation direct hydrolysis TAG and prepare 1,3-DAG.The purity of prepared 1,3-DAG is about 42%; Preparation time is about 72h; Purity still needs to improve, and the time still needs to shorten.
Summary of the invention
The object of the present invention is to provide a kind of TAG at antarctic candidia lipase A(CAL-A) direct hydrolysis prepares the method for high purity 1,3-DAG under effect.
Technical scheme
A method for triglyceride enzyme-squash techniqued 1,3-DAG, comprises and add ethanol or/and metal ion forms the step of hydrolyzation system in TAG, water and antarctic candidia lipase A;
The mol ratio of TAG and water is 1:2-10;
The consumption of antarctic candidia lipase A is the 0.5-5% of TAG quality;
The add-on of ethanol is the 4-20% of TAG quality;
In hydrolyzation system, the content of metal ion is 5-50mmol/L;
Described metal ion is that ferric ion is or/and mn ion.
According in instant sampling detection reaction system 1, the content of 3-DAG, determine optimum reacting time, reaction system is centrifugal, again oil phase is adopted molecular distillation, separation of glycerin monoesters and NEFA, triglyceride and triglyceride level (to be describedly separated, distillating method is ordinary method, processing parameter used, those skilled in the art can determine according to the performance of material).Wherein, triglyceride mutually in 1,3-DAG ratio can reach more than 80%.
The present invention studies discovery by experiment, ethanol is added in TAG hydrolyzation system, improve the hydrophobicity of TAG hydrolyzation system, antarctic candidia lipase A space can be made fully to stretch, improve 2 selection proneness to TAG, thus can effectively improve the content of in hydrolysate 1,3-DAG (namely, improve the purity of 1,3-DAG).
Metal ion can affect the activity that antarctic candidia lipase A is hydrolyzed TAG; Different metal ion can produce antarctic candidia lipase A activity different affects result; Some metal ion can improve the activity of antarctic candidia lipase A, and some metal ion can suppress antarctic candidia lipase A active; Wherein, the metal ion that the present invention adds can significantly improve the activity of antarctic candidia lipase A, thus improves the hydrolysis rate of triglyceride level.
And add ethanol and metal ion simultaneously; Antarctic candidia lipase A can not only be improved simultaneously and select proneness and Reaction time shorten to 2 of TAG; And hydrolysis rate increase rate increases further; As can be seen here, ethanol serves and promotes that metal ion improves the effect of hydrolysis rate.
The present invention studies discovery by experiment, and to hydrolyzation system, after the rotating speed high speed homogenate 10-30min of 5000-10000rpm, relative to the hydrolyzation system of non-homogenate, hydrolysis rate improves 30%, and hydrolysis time shortens 50h, only needs 22h.So aforesaid method, preferably also comprises: to hydrolyzation system with the step of the rotating speed high-speed homogenization 10-30min of 5000-10000rpm.
The optimum active temperature of antarctic candidia lipase A is 50-70 DEG C, the active pH of optimum is 5.5-7; So in order to give full play to the catalytic activity that antarctic candidia lipase A is hydrolyzed TAG, to improve hydrolysis rate, the temperature of TAG hydrolyzation system is 50-70 DEG C, pH is 5.5-7.0; Preferred temperature is with 70 DEG C, and adjustment pH is 7.0.
Aforesaid method, preferably, the mol ratio of TAG and water is 1:5.
Aforesaid method, preferably, the consumption of antarctic candidia lipase A is 2% of TAG quality.
Aforesaid method, preferably, the add-on of ethanol is 10% of TAG weight.
Aforesaid method, in hydrolyzation system, the content of metal ion is 20mmol/L.
In order to reduce production cost further, described TAG preferably adopts vegetables oil or animal oil, preferred, adopts the soybean oil of low value.
Described water can be tap water, also can be deionized water; In order to improve the promoter action of metal ion to enzymic activity, improving hydrolysis rate, preferentially adopting deionized water.
If 1,3-DAG prepared by method of the present invention, as food or for food, removes metal ion with sequestrant.
Beneficial effect
One is that reaction raw materials is cheap; Only adopt soybean oil, vegetable seed wet goods peanut oil, and lard etc., compared with the glycerine adopted with other preparation method, NEFA etc., cost reduces greatly;
Two is that reaction process is simple, and cost is low; This reaction is to have the higher CAL-A of 2 proneness for lipase, and by single step reaction hydrolyzing triglyceride 2 acyl groups, prepare 1,3-DAG, process is simple, reduces reaction cost, improves efficiency;
Three is the ethanol adding certain volume in reaction process, changes and is clear the hydrophobicity of answering system, selects proneness, improves the purity of 1,3-DAG for 2 that improve hydrolysis reaction;
Four is add a complexing metal ion in reaction system, improves lipase activity, shortens the hydrolysis time of triglyceride level;
Five is abundant homogenate, and water and oil phase fully mix, and increase reaction area, improves speed of reaction;
Six is prepared NEFA, and price is high, significantly improves the added value of production technique.
Embodiment
embodiment 1
1. 1000g soybean oil is mixed with 100g water, add 100g ethanol; With the rotating speed high-speed homogenization 20min of 5000rpm, prepare emulsion;
2. emulsion be heated to 70 DEG C and keep constant temperature, with hydrochloric acid or sodium hydroxide, the pH of emulsion being adjusted to 7.0;
3. add antarctic candidia lipase A 20g;
4., after reacting 22h, reaction terminates;
Reaction system is centrifugal 5., then oil phase is adopted molecular distillation, separation of glycerin monoesters and NEFA, triglyceride and triglyceride level; Wherein triglyceride mutually in 1,3-DAG ratio be 83%.
embodiment 2
1. 1000g soybean oil is mixed with 100g water, add 2.7g Iron(III) chloride hexahydrate and 1.98g tetrahydrate manganese chloride; With the rotating speed high-speed homogenization 20min of 5000rpm, prepare emulsion;
2. emulsion be heated to 70 DEG C and keep constant temperature, with sodium hydroxide or hydrochloric acid, the pH of emulsion being adjusted to 7.0;
3. add antarctic candidia lipase A 20g;
4., after reacting 18h, reaction terminates;
Reaction system is centrifugal 5., then oil phase is adopted molecular distillation, separation of glycerin monoesters and NEFA, triglyceride and triglyceride level; Wherein triglyceride mutually in 1,3-DAG ratio be 78%.
embodiment 3
1. 1000g soybean oil is mixed with 100g water, add 100g ethanol, 2.7g Iron(III) chloride hexahydrate and 1.98g tetrahydrate manganese chloride; With the rotating speed high-speed homogenization 20min of 5000rpm, prepare emulsion;
2. emulsion be heated to 70 DEG C and keep constant temperature, with sodium hydroxide or hydrochloric acid, the pH of emulsion being adjusted to 7.0;
3. add antarctic candidia lipase A 20g;
4., after reacting 16h, reaction terminates;
Reaction system is centrifugal 5., then oil phase is adopted molecular distillation, separation of glycerin monoesters and NEFA, triglyceride and triglyceride level; Wherein triglyceride mutually in 1,3-DAG ratio be 85%.
embodiment 4
1. 1000g soybean oil mixed with 100g water, add 100g ethanol, 2.7g Iron(III) chloride hexahydrate and 1.98g tetrahydrate manganese chloride, mixing, obtains mixed solution;
2. mixed solution be heated to 70 DEG C and keep constant temperature, with sodium hydroxide or hydrochloric acid, the pH of mixed solution being adjusted to 7.0;
3. add antarctic candidia lipase A 20g;
4., after reacting 28 h, reaction terminates;
Reaction system is centrifugal 5., then oil phase is adopted molecular distillation, separation of glycerin monoesters and NEFA, triglyceride and triglyceride level; Wherein triglyceride mutually in 1,3-DAG ratio be 83%
embodiment 5
1. 1000g soybean oil is mixed with 100g water, add 100g ethanol and 13.5g Iron(III) chloride hexahydrate (system is about 1.2L, and now iron concentration is 50mmol/L); With the rotating speed high-speed homogenization 20min of 5000rpm, prepare emulsion;
2. emulsion be heated to 70 DEG C and keep constant temperature, with sodium hydroxide or hydrochloric acid, the pH of emulsion being adjusted to 7.0;
3. add antarctic candidia lipase A 20g;
4., after reacting 18h, reaction terminates;
Reaction system is centrifugal 5., then oil phase is adopted molecular distillation, separation of glycerin monoesters and NEFA, triglyceride and triglyceride level; Wherein triglyceride mutually in 1,3-DAG ratio be 83%.
comparative example 1
1. 1000g soybean oil is mixed with 100g water, with the rotating speed of 500rpm mixing 20min, prepare emulsion;
2. emulsion be heated to 70 DEG C and keep constant temperature, with sodium hydroxide or hydrochloric acid, the pH of emulsion being adjusted to 7.0;
3. add antarctic candidia lipase A 20g;
4., after reacting 57 h, reaction terminates;
Reaction system is centrifugal 5., then oil phase is adopted molecular distillation, separation of glycerin monoesters and NEFA, triglyceride and triglyceride level; Wherein triglyceride mutually in 1,3-DAG ratio be 45%.
embodiment 6-10
Operation steps is with embodiment 3, and concrete technology parameter, reaction times, product purity are as shown in the table:
| Profit mol ratio | Lipase addition | Ethanol addition | Metal ion addition | Homogenate measure | pH | Temperature | Reaction times | 1,3-DAG purity | |
| Embodiment 5 | 1：5 | 2% | 10% | 50mmol/L | 5000rpm/20min | 7.0 | 70℃ | 18 | 83% |
| Embodiment 6 | 1：5 | 0.5% | 10% | 20mmol/L | 5000rpm/20min | 7.0 | 70℃ | 48 | 79% |
| Embodiment 7 | 1：5 | 0.5% | 10% | 20mmol/L | 10000rpm/20min | 7.0 | 70℃ | 15 | 82% |
| Embodiment 8 | 1：5 | 2% | 4% | 20mmol/L | 5000rpm/20min | 7.0 | 70℃ | 25 | 74% |
| Embodiment 9 | 1：5 | 2% | 20% | 20mmol/L | 5000rpm/20min | 7.0 | 70℃ | 20 | 78% |
| Embodiment 10 | 1：5 | 2% | 10% | 5mmol/L | 5000rpm/20min | 7.0 | 70℃ | 39 | 79% |
| Embodiment 11 | 1：5 | 2% | 10% | 50mmol/L | 5000rpm/20min | 7.0 | 70℃ | 19 | 81% |
In addition, adopt separately mn ion or ferric ion not to carry out testing (other conditions are with embodiment 3), be 16-17h between seasonable, product 1,3-DAG purity is 84-85%.
Claims (8)
1. a method for triglyceride enzyme-squash techniqued 1,3-DAG, is characterized in that, comprises and add ethanol or/and metal ion forms the step of hydrolyzation system in TAG, water and antarctic candidia lipase A;
The mol ratio of TAG and water is 1:2-10;
The consumption of antarctic candidia lipase A is the 0.5-5% of TAG quality;
The add-on of ethanol is the 4-20% of TAG quality;
In hydrolyzation system, the content of metal ion is 5-50mmol/L;
Described metal ion is that ferric ion is or/and mn ion.
2. method according to claim 1, is characterized in that, also comprises: to hydrolyzation system with the step of the rotating speed high-speed homogenization 10-30min of 5000-10000rpm.
3. according to the method for claim 1 or 2, it is characterized in that, the temperature of TAG hydrolyzation system is 50-70 DEG C, pH is 5.5-7.0.
4. method according to claim 3, is characterized in that, the mol ratio of TAG and water is 1:5.
5. method according to claim 4, is characterized in that, the consumption of antarctic candidia lipase A is 2% of TAG quality.
6. method according to claim 5, is characterized in that, the add-on of ethanol is 10% of TAG weight.
7. method according to claim 6, is characterized in that, in hydrolyzation system, the content of metal ion is 20mmol/L.
8. method according to claim 7, is characterized in that, described TAG adopts vegetables oil or animal oil.
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Cited By (1)
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| CN114426993A (en) * | 2022-02-18 | 2022-05-03 | 山东省农业科学院 | Method for obtaining 1, 3-diglyceride from high-oleic acid sunflower seed oil |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114426993A (en) * | 2022-02-18 | 2022-05-03 | 山东省农业科学院 | Method for obtaining 1, 3-diglyceride from high-oleic acid sunflower seed oil |
| CN114426993B (en) * | 2022-02-18 | 2024-01-26 | 山东省农业科学院 | Method for obtaining 1, 3-diglyceride from high oleic acid sunflower seed oil |
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