CN100999698B - Greasy of containing glycerin ester type conjugate linolic acid and production process thereof - Google Patents
Greasy of containing glycerin ester type conjugate linolic acid and production process thereof Download PDFInfo
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Abstract
The present invention relates to one kind of grease containing glyceride type conjugated linoleic acid and its production process. The grease includes glyceride type conjugated linoleic acid in 1-15 wt%, and over 88 % of the conjugated linoleic acid is located in the 1st and 3rd position. The production process includes the following steps: 1. mixing conjugated linoleic acid donor and triglyceride type grease in the weight ratio of 1-20 to 60; 2. lipase catalyzed reaction of the mixture at 35-90 deg.c; and 3. distilling the reaction product for separating and collecting the glyceride product with combined conjugated linoleic acid. The obtained product may be used to replace common edible oil for replenishing conjugated linoleic acid possessing the health functions of antagonizing atherosclerosiss, resisting cancer, slimming, etc.
Description
Technical field
The present invention relates to a kind of grease and production method thereof, particularly a kind of grease and production method thereof that contains glyceryl ester type conjugated linolic acid.
Background technology
Conjugated linolic acid (conjugated linoleic acid is abbreviated as CLA) is the general name of linoleic solid and position different structure mixture.Its conjugated double bond is usually located at C9 and C11 position or C10 and C12 position, and each two key can exist with cis or transconfiguration, 9c wherein, and 11t and 10t, 12c are the topmost existence forms of CLA.Studies show that conjugated linolic acid is a kind of very strong cancer-resisting substance, have atheroma and form that physiological functions such as bone formation are grown, reduce body fat and increased cutability and influence in anti-diabetic, antianaphylaxis, adjusting immunity, promotion.
The CLA of natural origin mainly is present in the butterfat and meat product of ruminating animal, and CLA comes by the unsaturated fatty acidss such as linoleic acid plus linolenic acid that rumen bacteria transforms in the meals in meat of ruminating animal and the butterfat.But, still remain at low levels at the conjugated linolic acid that butterfat and meat product comprised, in recent years, people have been developed the method for chemical method synthesis of conjugated linoleic acid again, and become a kind of important method that conjugated linolic acid is provided for people.At present, the conjugated linolic acid product mainly occurs with the ethyl ester type, and the supply of a small amount of glyceride form conjugated linolic acid is also arranged, and these products are processed to the soft capsule form usually, is used as healthcare products or functional foodstuff and sells.Conjugated linoleic acid ethyl ester directly added to can provide a kind of method of replenishing conjugated linolic acid easily in the edible oil, but low, the weak flavor of this oil and fat smoke point, is difficult to reach the purpose with the versatility of oil with common edible.At present, can not occur as yet, do not see the correlative study report yet as the conjugated linolic acid product of universal edible oil.
Summary of the invention
The objective of the invention is at the deficiencies in the prior art, a kind of edible grease that contains glyceryl ester type conjugated linolic acid is provided.
The present invention also aims to provide described greasy production method.
The grease that contains glyceryl ester type conjugated linolic acid of the present invention, its elementary cell are that a glycerine connects several lipid acid, are characterized in comprising in the lipid acid conjugated linolic acid that exists with the glyceryl ester type of 1～15% weight; Described conjugated linolic acid is positioned at 1,3 of glyceryl ester more than 88%.
Greasy local flavor and physical properties determine greasy acceptable degree and processing characteristics, are considered to two kinds of the most basic attributes of edible oil.Usually, 2 of natural edible oil mostly are unsaturated fatty acids.
The contriver finds through investigative test, when edible oil is carried out transesterify at random and 1, compare after 3 selectivity transesterification reactions, the change of the physical properties of ester interchanged prod and sense organ is bigger at random, so 2 lipid acid have significant contribution for greasy character, nutrition and local flavor, therefore, introduce conjugated linolic acid in edible oil, the ideal way is that conjugated linolic acid is incorporated into 1,3 of glyceryl ester as far as possible.
The contriver finds to have good local flavor for making the edible oil that comprises conjugated linolic acid through investigative test, must make conjugated linolic acid more than 88% be positioned at 1,3 of glyceryl ester, and preferably the conjugated linolic acid more than 90% is positioned at 1,3 of glyceryl ester.Generally contain the total hope of conjugated linolic acid Products Development person and improve the product cla levels as far as possible, the contriver finds through investigative test, the content of conjugated linolic acid also has influence for greasy local flavor and processing characteristics in the grease, when conjugated linolic acid is higher than 15%, slight bad flavor appears in grease, and greasy physical properties, also be affected as congealing point.In addition, because the restriction of picked-up dosage is not need very high-load conjugated linolic acid yet.So, have the characteristics of versatility for making the grease that contains glyceryl ester type conjugated linolic acid, wherein the content of conjugated linolic acid is 1～15%, preferably the content of conjugated linolic acid is 3～8%.
Greasy smoke point is to influence the important factor that grease is used, and for guaranteeing greasy versatility, the present invention limits the greasy smoke point that contains glyceryl ester type conjugated linolic acid should be not less than 190 ℃, and preferably, smoke point is not less than 210 ℃.
The above-mentioned greasy production method that contains glyceryl ester type conjugated linolic acid, the method includes the steps of:
(1) conjugated linolic acid donor and triglyceride type grease are 1～20: 60 mixing by weight;
(2) rich mixture that obtains of step (1) is through lipase-catalyzed reaction, and temperature of reaction is 35～90 ℃;
(3) reactant that obtains of step (2) is collected the glyceride product that is combined with conjugated linolic acid through fractionation by distillation.
The mixture of one or more in the preferred conjugated linoleic acid of described conjugated linolic acid donor, conjugated linolic acid methyl esters, conjugated linoleic acid ethyl ester, the conjugated linolic acid propyl ester.
The mixture of one or more in the preferred soybean oil of described triglyceride type grease, rapeseed oil, peanut oil, sunflower seed oil, Rice pollard oil, Semen Maydis oil, the plam oil.
As preferably, in the step (1), described conjugated linolic acid donor and triglyceride type grease mix in molar ratio at 2～8: 60.
In the step (2), described lipase is 1,3 specific lipase of immobilization.
The notable feature of this production method is to adopt 1,3 specific lipases are catalyzer, different with chemical catalyst, 1,3 specific lipases optionally 1,3 lipid acid of catalyzing glycerol ester react, thereby make conjugated linolic acid optionally be incorporated into 1 of glyceryl ester, 3, big variation does not take place in the composition that keeps 2 lipid acid.
Lipase during catalysis, has wide temperature applicable range in organic phase, top temperature can tolerate the high temperature more than 100 ℃, at high temperature, the catalysis activity of enzyme generally strengthens, but the stability decreases of enzyme, the present invention is from the angle of practicality, and the temperature of reaction that limits enzyme is 35～90 ℃.For reaching better economy, consider the recycling of lipase, lipase is preferably immobilized lipase, the lipase immobilization method has multiple, can adopt immobilization ways such as inorganic carrier absorption, resin absorption, at present, the selectable immobilized lipase of existing multiple commerce is for choosing.
Preferably, the mol ratio of described conjugated linolic acid donor and triglyceride level is 2～8: 60.
When adopting the free-fat enzyme to react, lipase is present in the grease reactant with the state that suspends, through after the certain reaction time reaches the intended conversion effect, enzyme is removed by filter, the removal of resolvase generally need be added flocculating aids and filter, filter the known unit operation of genus, the present invention does not do qualification to concrete filter method.When adopting immobilized enzyme to react, reaction formation can adopt batch operation, also can adopt the continous way operation, from industrialization angle easily, general preferred continuous operation.During continuous operation, immobilized lipase is loaded the filling bed type reactor, and reactant is passed through from reactor continuously, can finish reaction.For reaching the more operation of stabilization, generally do not adopt a filling bed type reactor, but adopt the mode of two above reactors in series, the inactivation of immobilized enzyme is from first reactor inactivation progressively, when the vigor of first reactor enzyme is reduced to certain level, first reactor can be removed and be used to fill new enzyme, second reactor becomes first reactor, and former first reactor is filled behind the new enzyme as last reactor.Reactant determines to be subjected to influence of various factors residence time of enzyme reactor, factors such as mass transfer coefficient as temperature, enzyme activity, immobilized enzyme, the residence time can be 0.5～20 hour, the present invention does not do qualification to reaction time, and with reach predetermined cla levels serve as control purpose.
The mixture of conjugated linolic acid donor and triglyceride level is after reaction, and conjugated linolic acid is incorporated into 1,3 of triglyceride level, and this place is incorporated into 1,3 and is meant and is incorporated into 1 or 3 or is incorporated into 1,3 simultaneously.Mixture is through after reacting, also to just can be used for edible purpose through further operation, further operation must comprise distillation, distillation can be molecular distillation, also can be physics deodorization mode general in the oil and fat refining, through distillation, the derivative of the low-molecular-weight fatty acid that contains in the reactant is removed, greasy smoke point improves greatly, and local flavor is improved simultaneously.Before entering distillation, according to demand, can carry out or not decolour to color, grease decoloring method commonly used is adopted in decolouring, generally adds carclazyte, gac etc. and decolours, and qualification is not done in the decolouring operation in the present invention.
Embodiment
Introduce enforcement of the present invention by the following examples in more detail.In described embodiment, unless specified otherwise, all per-cents all by weight.
Embodiment 1
Get the fatty-acid ethyl ester and the soybean oil blend 10kg that comprise 70% conjugated linolic acid and place reactor, the weight ratio of control conjugated linoleic acid ethyl ester (in pure substance) and soybean oil is 1: 60, the immobilized lipase Lipozyme TLIM (Novozymes company product) of adding 5% in the two mixture, reaction is 3 hours under 35 ℃ of conditions of 200 rev/mins of stirrings.Reactant is removed fatty-acid ethyl ester and free fatty acids gets grease 1 through 150 ℃ of molecular distillations.
Embodiment 2
Get the fatty-acid ethyl ester and the soybean oil blend 10kg that comprise 70% conjugated linolic acid and place reactor, the weight ratio of control conjugated linoleic acid ethyl ester (in pure substance) and soybean oil is 20: 60, with the two mixture by the filling bed type reactor of immobilized lipase Lipozyme TLIM is housed, temperature of reaction is 70 ℃, and the residence time of oil in reactor is 0.5 hour.Reactant is removed fatty-acid ethyl ester and free fatty acids etc. through 150 ℃ of molecular distillations and is got grease 2.
Embodiment 3
Get the fatty-acid ethyl ester and the rapeseed oil mixture 10kg that comprise 70% conjugated linolic acid and place reactor, the weight ratio of control conjugated linoleic acid ethyl ester (in pure substance) and soybean oil is 6: 60, with the two mixture by the filling bed type reactor of immobilized lipase Lipozyme TLIM is housed, temperature of reaction is 70 ℃, and the residence time of oil in reactor is 1 hour.Reactant is through 230 ℃ of underpressure distillation, and still-process constantly blasts high purity nitrogen, removes fatty-acid ethyl ester and free fatty acids etc. and gets grease 3.
Embodiment 4
Get the fatty acid methyl ester and the rapeseed oil mixture 10kg that comprise 70% conjugated linolic acid and place reactor, the weight ratio of control conjugated linolic acid methyl esters (in pure substance) and soybean oil is 6: 60, with the two mixture by the filling bed type reactor of immobilized lipase Lipozyme TLIM is housed, temperature of reaction is 70 ℃, and the residence time of oil in reactor is 1 hour.Reactant is through 230 ℃ of underpressure distillation, and still-process constantly blasts high purity nitrogen, removes fatty acid methyl ester and free fatty acids etc. and gets grease 4.
Embodiment 5
Get the fatty acid methyl ester and the soybean oil blend 10kg that comprise 70% conjugated linolic acid and place reactor, the weight ratio of control conjugated linoleic acid ethyl ester (in pure substance) and soybean oil is 6: 60, with the two mixture by the filling bed type reactor of immobilized lipase Lipozyme TLIM is housed, temperature of reaction is 90 ℃, and the residence time of oil in reactor is 1 hour.Reactant is through 230 ℃ of underpressure distillation, and still-process constantly blasts high purity nitrogen, removes fatty acid methyl ester and free fatty acids etc. and gets grease 5.
Embodiment 6
In soybean oil, add conjugated linoleic acid ethyl ester, make that cla levels is 3.0%, get grease 6.
Embodiment 7
Get the fatty-acid ethyl ester and the soybean oil blend 10kg that comprise 70% conjugated linolic acid and place reactor, the weight ratio of control conjugated linoleic acid ethyl ester (in pure substance) and soybean oil is 10: 60, and the NaOH that adds 0.3% in the mixture of the two is carried out chemical transesterify.After 230 ℃ of underpressure distillation, still-process constantly blasts high purity nitrogen to reactant through citric acid solution washing, remove fatty-acid ethyl ester and free fatty acids etc. grease 7.
Embodiment 8
Get the fatty-acid ethyl ester and the rapeseed oil mixture 10kg that comprise 70% conjugated linolic acid and place reactor, the weight ratio of control conjugated linoleic acid ethyl ester (in pure substance) and soybean oil is 30: 60, with the two mixture by the filling bed type reactor of immobilized lipase Novozym435 (Novozymes company product) is housed, temperature of reaction is 70 ℃, and the residence time of oil in reactor is 1 hour.Reactant is through 230 ℃ of underpressure distillation, and still-process constantly blasts high purity nitrogen, removes fatty-acid ethyl ester and free fatty acids etc. and gets grease 8.
Embodiment 9
1) conjugated linolic acid is positioned at the Determination on content of 1,3 of glyceryl ester
The analysis of conjugated linolic acid binding site in the grease, at first, adopt 1,3 specific lipases, as porcine pancreatic lipase grease is hydrolyzed, degree of hydrolysis is controlled to be about 20%, 30 ℃ of hydrolysis temperatures, hydrolysate is through the silica gel thin sheet chromatography, developping solution is normal hexane, ether, acetate (70: 30: 1), launches the dried solvent of back volatilization, comprises triglyceride level, lipid acid, diacylglycerol and mono-glycerides in the grease, the qualitative employing standard control method of each composition adopts the iodine vapor development process during Rf pH-value determination pH.The silica gel of lipid acid and mono-glycerides correspondence carries out esterification and handles, through gas chromatographic analysis behind the n-hexane extraction respectively, fatty acid part is represented the content A of 1,3 conjugated linolic acid of glyceryl ester, and mono-glycerides is partly represented the content B of 2 conjugated linolic acids of glyceryl ester, calculation formula is as follows, the results are shown in Table 1.
2) assay of conjugated linolic acid in the grease
The assay of conjugated linolic acid in the grease is got grease and is carried out the esterification gas chromatography determination, the results are shown in Table 1.
3) flavor evaluation
★ ★ ★ ★ excellent flavor does not have any bad flavor
★ ★ ★ excellent flavor has extremely slight non-grease typical flavor
★ ★ local flavor can be accepted
The ★ weak flavor
The grease 1～7 that application test is obtained carries out the French fries test, and flavor evaluation is passed judgment on by 8 judges, and synthesis result is as shown in table 1.
Table 1 oil property
| Smoke point (℃) | Local flavor | Conjugated linolic acid is positioned at 1,3 content (%) | Cla levels in the grease (%) | |
| Grease 1 | 218 | ★★★★ | 96.3 | 1.1 |
| Grease 2 | 192 | ★★★ | 88.3 | 15.1 |
| Grease 3 | 215 | ★★★★ | 93.2 | 6.1 |
| Grease 4 | 218 | ★★★★ | 92.6 | 6.3 |
| Grease 5 | 217 | ★★★★ | 92.9 | 6.8 |
| Grease 6 | ＜160 | ★ | - | 3.0 |
| Grease 7 | 209 | ★★ | 69.8 | 7.5 |
| Grease 8 | 211 | ★★ | 75.2 | 21.2 |
Grease 1～5 is the product that the enzyme process transesterify obtains, and conjugated linolic acid is incorporated into 1,3 of glyceryl ester, and product has shown good flavor characteristics, and the higher and oil with common edible of smoke point has good versatility.Grease 6 is the greases that contain conjugated linolic acid that adopt conjugated linoleic acid ethyl ester to be deployed into, and this formulation product weak flavor, smoke point are lower than 160 ℃, are difficult to normal use basically.Grease 7 is the products that adopt non-specific chemical transesterify to obtain, and conjugated linolic acid is branch at random basically, and product special flavour is under some influence.Grease 8 is the products that adopt the strong lipase reaction of specificity to obtain, and this product includes more conjugated linolic acid, and conjugated linolic acid has suitable major part not to be positioned at 1,3, and this product special flavour is affected.Illustrate, limit cla levels in the product and be 1～15% and limit conjugated linolic acid 88% or more to be positioned at 1,3 of glyceryl ester be the key character of guarantee grease local flavor.
Claims (4)
1. grease that contains glyceryl ester type conjugated linolic acid, its elementary cell is that a glycerine connects several lipid acid, it is characterized in that comprising in the lipid acid conjugated linolic acid that exists with the glyceryl ester type of 1～15% weight; Glyceryl ester be the mixture of conjugated linolic acid donor and triglyceride level after reaction, conjugated linolic acid is incorporated into 1 of triglyceride level or 3 or is incorporated into 1,3 simultaneously; Wherein be incorporated into 1 and 3 and be incorporated into 1,3 conjugated linolic acid simultaneously and account for more than 88% of conjugated linolic acid in the grease.
2. grease according to claim 1 is characterized in that comprising in the lipid acid conjugated linolic acid that exists with the glyceryl ester type of 3～8% weight; Glyceryl ester be the mixture of conjugated linolic acid donor and triglyceride level after reaction, conjugated linolic acid is incorporated into 1 of triglyceride level or 3 or is incorporated into 1,3 simultaneously; Wherein be incorporated into 1 and 3 and be incorporated into 1,3 conjugated linolic acid simultaneously and account for more than 90% of conjugated linolic acid in the grease.
3. grease according to claim 1 and 2 is characterized in that its smoke point is greater than 190 ℃.
4. grease according to claim 3 is characterized in that its smoke point is greater than 210 ℃.
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Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101185465B (en) * | 2007-12-14 | 2010-05-19 | 华南理工大学 | Fat compositions and uses thereof |
| CN102796776B (en) * | 2012-07-13 | 2014-12-03 | 许浮萍 | Method for preparing functional organic acid triglyceride through utilizing lipese |
| CN103710400B (en) * | 2013-12-27 | 2016-02-24 | 南昌大学 | The method of tg cla is rich in a kind of sn-2 of preparation position |
| CN103849660B (en) * | 2014-03-28 | 2016-01-06 | 大连医诺生物有限公司 | A kind of with immobilized lipase be catalyzer be coupled the method for legal system for conjugated linolic acid |
| CN105331648B (en) * | 2015-10-08 | 2018-12-18 | 中科田园(北京)农业科技有限公司 | A kind of alpha-linolenic acid monoglyceride and preparation method thereof |
| CN109090613A (en) * | 2018-07-13 | 2018-12-28 | 大连医诺生物股份有限公司 | A kind of conjugated linoleic acid glyceride microcapsule powder and preparation method thereof |
| CN109169969B (en) * | 2018-10-31 | 2021-02-12 | 华中农业大学 | Preparation method of high-smoke-point mixed edible oil containing polyunsaturated fatty acid |
| CN110338222B (en) * | 2019-08-23 | 2023-03-14 | 李跃东 | High-purity conjugated linoleic acid yak yoghourt and preparation method thereof |
| CN110438175A (en) * | 2019-09-16 | 2019-11-12 | 东北农业大学 | A kind of method that light phase rice bran oil and conjugated linoleic acid transesterification after freezing separation prepare functional grease |
| CN110541005A (en) * | 2019-09-16 | 2019-12-06 | 东北农业大学 | Method for preparing functional grease by exchanging frozen and separated heavy-phase rice bran oil with conjugated linoleate |
| CN112662644B (en) * | 2021-01-19 | 2022-04-22 | 华南理工大学 | Diglycerol phosphate phosphodiesterase mutant and application thereof |
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| WO2005052102A1 (en) * | 2003-11-28 | 2005-06-09 | Onbio Corporation | A composition enriched in diglyceride with conjugated linoleic acid |
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| WO2003043972A2 (en) * | 2001-11-20 | 2003-05-30 | Natural As | Functional acylglycerides |
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