CN113768047A - Slow-release butyric acid lauric acid mixed structure ester and preparation method and application thereof - Google Patents
Slow-release butyric acid lauric acid mixed structure ester and preparation method and application thereof Download PDFInfo
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- YMNGVCRNVMYEFS-UHFFFAOYSA-N butanoic acid;dodecanoic acid Chemical compound CCCC(O)=O.CCCCCCCCCCCC(O)=O YMNGVCRNVMYEFS-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 238000002360 preparation method Methods 0.000 title claims abstract description 24
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- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/158—Fatty acids; Fats; Products containing oils or fats
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/02—Preparation of carboxylic acid esters by interreacting ester groups, i.e. transesterification
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Medicinal Preparation (AREA)
Abstract
The invention discloses a slow-release type butyric acid lauric acid mixed structure ester and a preparation method and application thereof, and relates to the technical field of oil synthesis, in particular to a novel butyric acid lauric acid mixed structure ester which mainly comprises glycerol monobutyrate dilaurate and glycerol dibutyrate monolaurate, wherein after the mixed structure ester is contacted with lipase in intestinal tracts, butyric acid and glycerol monolaurate can be slowly released, and intestinal microorganisms can be induced to generate active change within 24 hours. Compared with the existing feed additive, the mixed structure ester can improve the intestinal function of animals more effectively.
Description
Technical Field
The invention relates to the technical field of oil synthesis, in particular to a slow-release type butyric acid lauric acid mixed structure ester and a preparation method and application thereof.
Background
In modern farming, short and medium chain fatty acids and their glycerides are widely used in feed additives for the purpose of improving animal health and growth rate, but their rapid digestion and absorption in the body reduces their functional value.
Butyric acid is a short-chain fatty acid, can be directly absorbed by intestinal tract cells, and is an important energy source of the intestinal tract epithelial cells. Butyric acid has been widely used as a feed additive in the breeding of commercial animals such as pigs, cattle, chickens and shrimps. However, butyric acid or butyrin ester taken orally is easily digested and absorbed in the stomach environment, so that the butyric acid is difficult to reach the intestinal tract part where microorganisms gather, and the transmission effect and the exertion of the effect of the butyric acid are greatly limited.
The monolaurin is an esterified form of the lauric acid glycerides with the best antibacterial and antiviral ability, and its biological activity is also superior to that of the lauric acid in the free state. Currently, glycerol monolaurate has been widely used in animal farming, for example:
the patent application publication No. CN110506864A discloses a pig feed replacement anti-additive and application thereof in pig feed, wherein the lauric acid monoglyceride and formic acid in the additive are used in combination to remarkably improve the height of the villus in the jejunum of piglets, so that the intestinal health is improved, and the feed utilization rate of the piglets is improved.
The invention patent application document with the publication number of CN201610247228 discloses a chicken feed additive which is formed by mixing 10-45% of glycerol monolaurate, 10-30% of glycerol dilaurate, 30-50% of glycerol monostearate and 0-20% of carrier. The additive can remarkably improve the egg laying performance and the egg quality of the laying hens.
However, the existing feed additive cannot completely meet the requirement of cultivation, and how to improve the use efficiency of the feed additive and further effectively improve the intestinal health of animals is one of the problems to be solved urgently.
In view of this, the invention is particularly proposed.
Disclosure of Invention
The invention aims to provide a slow-release butyric acid lauric acid mixed structure ester and a preparation method and application thereof.
The invention is realized by the following steps:
in a first aspect, an embodiment of the present invention provides a butyric acid lauric acid mixed structural ester, which includes the following components: glycerol monobutyrate dilaurate and glycerol monobutyrate monolaurate.
In a second aspect, embodiments of the present invention provide a method for preparing a mixed structure ester of butyric acid and lauric acid as described in the previous embodiments, comprising: mixing tributyrin and trilaurin to perform ester exchange reaction.
In a third aspect, embodiments of the present invention provide a use of a mixed structural ester of butyric acid and lauric acid as described in the previous embodiments or a mixed structural ester of butyric acid and lauric acid prepared by the preparation method described in the previous embodiments in the preparation of a feed additive for promoting intestinal health.
In a fourth aspect, the present invention provides the use of a mixed structural ester of butyric acid and lauric acid as described in the previous examples or the mixed structural ester of butyric acid and lauric acid prepared by the preparation method as described in the previous examples in the preparation of a feed additive for regulating the environment of intestinal microorganisms.
In a fifth aspect, embodiments of the present invention provide a feed additive comprising a mixed structural ester of butyric acid and lauric acid as described in the previous embodiments or prepared by the preparation method described in the previous embodiments.
In a sixth aspect, embodiments of the present invention provide a feed comprising a mixed structural ester of butyric acid and lauric acid as described in the previous embodiments or prepared by the preparation method described in the previous embodiments.
The invention has the following beneficial effects:
the invention provides a novel butyric acid lauric acid mixed structure ester, which comprises glycerol monobutyrate dilaurate and glycerol dibutyrate monolaurate, wherein the mixed structure ester has the effect of slowly releasing butyric acid and glycerol monolaurate after contacting lipase in animal intestinal tracts, can more effectively improve the transmission effect of functional factors compared with the existing feed additive, can induce intestinal microorganisms to actively change within 24 hours, and can more effectively improve the animal intestinal tract function.
Drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings needed to be used in the embodiments will be briefly described below, it should be understood that the following drawings only illustrate some embodiments of the present invention and therefore should not be considered as limiting the scope, and for those skilled in the art, other related drawings can be obtained according to the drawings without inventive efforts.
FIG. 1 is a graph showing the change in butyric acid content in the static digestion of example 2; wherein A, the content change of butyric acid in gastric digestion is simulated. Simulating the change of butyric acid content in intestinal digestion; mBLDenotes a physical mixture of tributyrin and trilaurin, SBLRepresents butyric acid lauric acid mixed structure ester; the number of replicate samples per time is 3, and the results are expressed as mean ± standard deviation;
FIG. 2 is the change in GML content in the static digestion of example 2; wherein, A is the change of GML content in simulated gastric digestion; simulating the change of GML content in intestinal digestion; mBLIs represented by the formulaBLPhysical mixture of glyceryl tributyrate and glyceryl trilaurate with the same fatty acid composition, SBLRepresents butyric acid lauric acid mixed structure ester; the number of replicate samples per time is 3, and the results are expressed as mean ± standard deviation;
FIG. 3 is a graph showing the change in butyric acid content in the mouse model of example 2; wherein A is the content change of butyric acid in intestinal contents at different intestinal parts and different sampling time points; capital letters show the difference of butyric acid content in contents of different intestinal tracts at a certain sampling time point, different letters show that the difference is obvious (P is less than 0.05), lower case letters show the difference of butyric acid content in contents of intestinal tracts at different gavage time points of a certain intestinal tract, different letters show that the difference is obvious (P is less than 0.05), and structural esters and physical mixtures are separately compared. B, the content of butyric acid in colon contents after 8h of intragastric administration indicates that P is less than 0.0001; mBLDenotes a physical mixture of tributyrin and trilaurin, SBLMeans DMixed structure ester of lauric acid; the numerical subscripts '-1, -2, -4, -8' indicate samples at 1,2,4,8 hours after gavage, respectively; the number of replicate samples per time is 6, and the results are expressed as mean ± sd;
FIG. 4 is the change in GML content in the mouse model of example 2; wherein A is the change of GML content in intestinal contents at different intestinal positions and different sampling time points; capital letters show the difference of butyric acid content in contents of different intestinal tracts at a certain sampling time point, different letters show that the difference is obvious (P is less than 0.05), lower case letters show the difference of butyric acid content in contents of intestinal tracts at different gavage time points of a certain intestinal tract, different letters show that the difference is obvious (P is less than 0.05), and structural esters and physical mixtures are separately compared. B, GML content in jejunum content after gastric lavage for 1h, wherein P is less than 0.0001; c, GML content in jejunum content after 2h of intragastric administration, wherein P is less than 0.05; d, GML content in jejunum content after 8h of gastric lavage indicates that P is less than 0.05; e, GML content in colon contents after 8h of intragastric administration, wherein P is less than 0.001; mBLDenotes a physical mixture of tributyrin and trilaurin, SBLRepresents butyric acid lauric acid mixed structure ester; p < 0.05 is considered to be a significant difference, and P < 0.1 is considered to be a significant trend; the numerical subscripts '-1, -2, -4, -8' indicate samples at 1,2,4,8 hours after gavage, respectively; the number of replicate samples per time is 6, and the results are expressed as mean ± sd;
FIG. 5 is the change of microbes in the cecal intestinal tract of the mice 24h after the gavage of example 3; wherein, A: (ii) bifidobacterium abundance; b: abundance of Allobaculum bacteria; c: unidentified F16 genus abundance; d: CC-115 genus abundance; p < 0.05 was considered to be significantly different, and P < 0.1 was considered to be significantly trending.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.
The embodiment of the invention provides butyric acid lauric acid mixed structure ester, which comprises the following components: glycerol monobutyrate dilaurate and glycerol monobutyrate monolaurate.
The inventor provides the butyric acid-lauric acid mixed structure ester through a series of creative works, has the characteristic of slowly releasing butyric acid and glycerol monolaurate, and can more effectively improve the intestinal function of animals and maintain the intestinal environment stable state to be beneficial to the growth of the animals compared with the existing feed additive.
In some embodiments, the weight ratio of glycerol monobutyrate dilaurate to glycerol dibutyrate monolaurate is not limited. Preferably, the weight ratio of the glycerol monobutyrate dilaurate to the glycerol dibutyrate monolaurate is (1-5): 1, the weight ratio can be specifically 1:1. 2: 1. 3: 1. 4: 1 or 5: 1.
preferably, the glycerol monobutyrate dilaurate comprises: 1.2-dilauric-3-butyric acid glycerol ester and 1.3-dilauric-2-butyric acid glycerol ester.
Preferably, the glycerol monobutyrate monolaurate comprises: 1.2-dibutyric acid-3-lauric acid glyceride and 1.3-dibutyric acid-2-lauric acid glyceride.
Preferably, the butyric acid lauric acid mixed structure ester further comprises at least one of the following components: lauric acid, glycerol monobutyrate, glycerol tributyrate, glycerol monobutyrate monolaurate and glycerol dilaurate. Within the limited range, the effect of the butyric acid-lauric acid mixed structure ester is better.
Preferably, the glycerol monobutyrate monolaurate is selected from: at least one of 1-butyric acid-3-lauric acid glyceride, 3-butyric acid-1-lauric acid glyceride, 2-butyric acid-3-lauric acid glyceride, 2-lauric acid-1-butyric acid glyceride, and 2-lauric acid-3-butyric acid glyceride. More preferably, the butyric acid lauric acid mixed structure ester comprises the following components in parts by weight: 5-20 parts of lauric acid, 1-10 parts of glycerol monobutyrate, 1-10 parts of glycerol tributyrate, 10-30 parts of glycerol monobutyrate monolaurate, 15-40 parts of glycerol dibutyrate monolaurate, 5-20 parts of glycerol dilaurate and 20-50 parts of glycerol monobutyrate dilaurate.
Preferably, the butyric acid lauric acid mixed structure ester comprises the following components in parts by weight: 5-20 parts of lauric acid, 1-10 parts of glycerol monobutyrate, 1-10 parts of glycerol tributyrate, 3-10 parts of 1-butyric acid-3-lauric acid glyceride, 7-20 parts of 2-butyric acid-1-lauric acid glyceride, 6-15 parts of 1, 2-dibutyric acid-3-lauric acid glyceride, 9-25 parts of 1, 3-dibutyric acid-2-lauric acid glyceride, 1-7 parts of 1, 2-dilauric acid glyceride, 4-13 parts of 1, 3-dilauric acid glyceride, 12-30 parts of 1, 2-dilauric acid-3-butyric acid glyceride and 8-20 parts of 1, 3-dilauric acid-2-butyric acid glyceride. Under the limited range of the specific components and the proportion thereof, the butyric acid lauric acid mixed structure ester can better exert the action effect. Specifically, the weight parts of lauric acid may be selected from 5 parts, 6 parts, 8 parts, 10 parts, 12 parts, 14 parts, 16 parts, 18 parts, or 20 parts; the weight portion of the glycerol monobutyrate can be selected from 1 portion, 2 portions, 4 portions, 6 portions, 8 portions or 10 portions; the weight part of the tributyrin can be selected from 1 part, 2 parts, 4 parts, 6 parts, 8 parts or 10 parts; the weight part of the 1-butyric acid-3-lauric glyceride can be selected from 3 parts, 4 parts, 6 parts, 8 parts or 10 parts; the weight parts of the 1.2-dibutyrate-3-lauric glyceride can be selected from 6 parts, 9 parts, 10 parts, 12 parts, 14 parts, 16 parts, 18 parts, 20 parts or 22 parts; the weight portion of the 1.3-dibutyrate-2-lauric glyceride can be selected from 9 portions, 10 portions, 12 portions, 14 portions, 16 portions, 18 portions, 20 portions, 22 portions or 24 portions; 1.2-Glycerol dilaurate in a weight fraction selected from 1 part, 2 parts, 4 parts, 6 parts, or 7 parts; 1.3-Glycerol dilaurate in a weight fraction selected from 4 parts, 6 parts, 8 parts, 10 parts, 12 parts, or 13 parts; the weight parts of the 1.2-dilaurate-3-butyrin can be selected from 12 parts, 14 parts, 16 parts, 18 parts, 20 parts, 22 parts, 24 parts, 26 parts, 28 parts or 30 parts; the weight parts of 1, 3-dilaurate-2-butyrin may be selected from 8 parts, 10 parts, 12 parts, 14 parts, 16 parts, 18 parts, or 20 parts.
The embodiment of the present invention further provides a method for preparing a butyric acid lauric acid mixed structure ester according to any of the foregoing embodiments, which includes: mixing tributyrin and trilaurin to perform ester exchange reaction. "transesterification" as used herein refers to a transesterification reaction in which an ester reacts with an ester (different ester) to form a new ester and a new alcohol/acid/ester, catalyzed by an acid, base or enzyme.
Preferably, when the ester exchange reaction occurs, the mixing molar ratio of the tributyrin and the trilaurin is (0.5-5): (0.5 to 5);
preferably, the mixing molar ratio is (0.5-1.5): (0.5 to 1.5). More preferably, the mixing molar ratio is 1:1. under the limitation, the generated butyric acid lauric acid mixed structure ester has better sustained-release effect of butyric acid and glycerol monolaurate, and can better exert the effect of the butyric acid lauric acid mixed structure ester on the intestinal tracts of animals.
Preferably, the transesterification reaction is carried out as follows: mixing tributyrin and trilaurin at 60-70 ℃ in a nitrogen atmosphere, adding immobilized lipase after the tributyrin and the trilaurin are uniformly mixed and are in a liquid state, preserving the temperature for 2-6 h, and removing the immobilized lipase to obtain the butyric-lauric acid mixed structure ester;
preferably, the addition amount of the immobilized lipase is 5-15% of the total weight of the mixture.
Preferably, the immobilized lipase is selected from the group consisting of: any one of immobilized Aspergillus oryzae lipase, immobilized Rhizopus oryzae lipase and immobilized Rhizomucor miehei lipase.
The embodiment of the invention also provides application of the butyric acid lauric acid mixed structure ester prepared by the preparation method of any embodiment in preparation of a feed additive for promoting intestinal health.
In some embodiments, promoting gut health can be achieved by: maintaining the steady state of the intestinal microbial flora and improving at least one function of the microbial flora structure.
The embodiment of the invention also provides application of the butyric acid lauric acid mixed structure ester prepared by the preparation method of any embodiment in the preparation of a feed additive for regulating the environment of intestinal microorganisms.
Preferably, said modulating the gut microbial environment means increasing the abundance of gut microbes;
preferably, the regulation of the gut microbial environment means increasing the abundance of at least one of the genera bifidobacterium, Allobaculum, F16 and CC-115.
The embodiment of the invention also provides a feed additive, which comprises the butyric acid lauric acid mixed structure ester prepared by the preparation method of any embodiment.
In some embodiments, the feed may also include existing feed additive carriers and/or components for farm animals, available from existing sources, and will not be described in detail.
The embodiment of the invention also provides a feed which comprises the butyric acid lauric acid mixed structure ester prepared by the preparation method of any embodiment.
In some embodiments, the feed may also include existing feed carriers and/or components for the farmed animals, which are available from existing sources and will not be described in detail.
The features and properties of the present invention are described in further detail below with reference to examples.
Example 1 preparation and composition determination of Slow Release lauric acid butyrate Mixed structural ester
Adding a certain amount of tributyrin and trilaurin into a 100mL round-bottom flask (the molar ratio is 1:1), filling nitrogen, covering a turning plug, placing the flask in a constant-temperature water bath oscillator at the temperature of 65 ℃, adding immobilized lipase (10%, w/w) after reaction substrates are uniformly mixed and are in a liquid state, filling nitrogen again for protection, covering the turning plug, and preserving the temperature for reaction for 4 hours under the condition of 200 rmp. And after the reaction is finished, filtering to remove the immobilized enzyme, and collecting to obtain the butyric acid-lauric acid mixed structure ester.
Accurately weighing 10.0mg of structural ester, placing the structural ester in a 10mL volumetric flask, performing constant volume to a scale by using methanol, performing ultrasonic complete dissolution, and transferring the structural ester to a 2mL sampling flask for GC-MS analysis. The instrument model is 7890A-5975C gas chromatography-mass spectrometer (GC-MS), Agilent technologies, Inc. of America. Chromatographic conditions are as follows: the chromatographic column is HP-5MS (30.0m is multiplied by 250 μm,0.25 μm); maintaining the initial temperature of chromatographic column at 50 deg.C for 2min, and maintaining at 15 deg.C/min to 280 deg.C for 20 min; the temperature of the gasification chamber is 280 ℃; the transmission line temperature is 280 ℃; carrier gas He; the carrier gas flow is 1.0 mL/min; the split ratio is 10: 1; the amount of the sample was 0.5. mu.L. Mass spectrum conditions: an EI source; electron energy 70 eV; the ion source temperature is 300 ℃; a quadrupole rod is 150 ℃; the scanning mode is Scan; the scanning mass range is 20-800 u.
The composition of the butyric lauric acid mixed structure ester is identified as shown in table 1.
TABLE 1 ingredient Table of mixed structure butyrate-laurate esters
Example 2 in vivo and in vitro digestion Properties of Slow Release Butyric acid lauric acid Mixed Structure ester
The digestion characteristics of butyrate-laurate mixed-structure esters were studied in an in vitro digestion model and in an in vivo mouse model. Specifically, in this example, using tributyrin and trilaurin as raw materials in a molar ratio of 1:1.5, 7% (w/w) of enzyme was added, and reacted at 62 ℃ for 6 hours to prepare a lauric acid butyrate structural ester (S) obtained substantially in the same manner as in example 1 as an experimental groupLBL) Glycerol tributyrate and glycerol trilaurate (M) in equal molar amountsLBL) As a control group, experiments were performed in an in vitro digestion model and an in vivo mouse model. In an in vitro digestion model, digestion samples are taken 0min, 30min, 60min, 90min, 120min, 150min, 180min, 210min and 240min after digestion, wherein the first 120min is in vitro simulated gastric digestion, and the second 120min to 240min is simulated intestinal digestion. In the in vivo mouse model, intestinal content samples (jejunum, ileum, caecum and colon) were taken at 0min, 60min, 120min, 240min, 320min after gavage). The samples taken were subjected to GC-FID analysis and monitored with emphasis on butyric acid and Glycerol Monolaurate (GML). The results are shown in FIGS. 1 to 4.
From the results, in the in vitro digestion model, SBLThe slow release of butyric acid is shown to be more gradual, and the slow release effect is significant, but the slow release effect on butyric acid is not significantly shown in the simulation of intestinal digestion. For GML, S is present during the complete simulated digestionBLNone of them shows the effect of sustained release. In the in vivo mouse model, S was obtained at each sampling point, except for the colon contents digested for 8hBLAnd MBLThere was no significant difference in the release of butyric acid.
In the in vivo mouse model, SBLHas obvious effect of delaying GML release: after 1h of digestion in vivo, SBLAnd MBLThe GML content of the treated group is obviously higher than that of the blank group, and after 2 hours of digestion, S is addedBLThe treatment group had a significantly higher jejunal GML content than MBLTrend in treatment groups, S after 8h of continued digestionBLThe treatment group had significantly higher jejunal GML than MBLAnd (4) grouping. Relative to the physical mixture, SBLThe sustained release effect of butyric acid embodied in gastric digestion and the sustained high-level release of GML in intestinal tracts in vivo can be beneficial to improving the functional value of the gastric juice and maintaining the intestinal tract environment steady state. In the in vivo model, S is added to the colon contents after 8h of digestionBLProcess group and MBLThe difference in butyric acid content between the treatment groups was not significant.
Example 3 transient modification of Slow-Release Butyriac Mixed Structure ester on intestinal microorganisms
The intestinal microorganisms are easily affected by environmental factors such as dietary components and the like, and the disturbance to the intestinal microorganisms can be reflected within a short time (24-48 h). In this example, using tributyrin and trilaurin at a molar ratio of 1:2 as starting materials, 12% (w/w) of enzyme addition, and reacting at 67 ℃ for 4 hours, lauric butyrate obtained (approximately the same as in example 1) was prepared as an experimental group (S)LBL) At the same molar content of tributanoic acidGlycerides and trilaurin (M)LBL) As a control group, experiments were performed in an in vitro digestion model and an in vivo mouse model. S was analyzed by 16S RNA sequencing by collecting cecal samples 24h after gavageBLAnd MBLThe perturbation effect on mouse intestinal microorganisms (as in the previous examples) is shown in FIG. 5.
Bifidobacteria are well-established probiotics. The analysis result shows that SBLThe abundance of Bifidobacterium in the treated group was significantly higher than that in the control group and MBLTrend of the group.
In addition, Allobaculum is also a potential intestinal microorganism with health benefits, which is found in SBLThe abundance in the treatment group had a significantly increased trend relative to the blank group, which also demonstrates SBLRelative to MBLWith better potential health benefits.
The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention, and various modifications and changes may be made by those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. A butyric lauric acid mixed structure ester is characterized by comprising the following components: glycerol monobutyrate dilaurate and glycerol monobutyrate monolaurate.
2. The mixed structural butyrate-lauric acid ester according to claim 1, wherein the weight ratio of glycerol monobutyrate dilaurate to glycerol dibutyrate monolaurate is (1-5): 1;
preferably, the glycerol monobutyrate dilaurate comprises: 1, 2-dilaurate-3-butyrin and 1, 3-dilaurate-2-butyrin;
the glycerol monobutyrate laurate comprises: 1.2-dibutyric acid-3-lauric acid glyceride and 1.3-dibutyric acid-2-lauric acid glyceride.
3. The mixed butyrate-lauric acid structural ester according to claim 2, characterized in that it further comprises at least one of the following components: lauric acid, monobutyric acid glycerol ester, tributyrin, monobutyric acid glycerol ester monolaurate and glycerol dilaurate;
preferably, the glycerol monobutyrate monolaurate is selected from: at least one of 1-butyric acid-3-lauric acid glyceride, 3-butyric acid-1-lauric acid glyceride, 2-butyric acid-3-lauric acid glyceride, 2-lauric acid-1-butyric acid glyceride, and 2-lauric acid-3-butyric acid glyceride.
4. The mixed structural butyrate-lauric acid ester according to claim 3, characterized in that it comprises the following components in parts by weight: 5-20 parts of lauric acid, 1-10 parts of glycerol monobutyrate, 1-10 parts of glycerol tributyrate, 10-30 parts of glycerol monobutyrate monolaurate, 15-40 parts of glycerol dibutyrate monolaurate, 5-20 parts of glycerol dilaurate and 20-50 parts of glycerol monobutyrate dilaurate;
preferably, the butyric acid lauric acid mixed structure ester comprises the following components in parts by weight: 5-20 parts of lauric acid, 1-10 parts of glycerol monobutyrate, 1-10 parts of glycerol tributyrate, 3-10 parts of 1-butyric acid-3-lauric acid glyceride, 7-20 parts of 2-butyric acid-1 lauric acid glyceride, 6-15 parts of 1, 2-dibutyric acid-3-lauric acid glyceride, 9-25 parts of 1, 3-dibutyric acid-2-lauric acid glyceride, 1-7 parts of 1, 2-dilauric acid glyceride, 4-13 parts of 1, 3-dilauric acid glyceride, 12-30 parts of 1, 2-dilauric acid-3-butyric acid glyceride and 8-20 parts of 1, 3-dilauric acid-2-butyric acid glyceride.
5. The method for producing a mixed structural ester of butyric and lauric acids according to any one of claims 1 to 4, comprising: mixing tributyrin and trilaurin to perform enzyme-catalyzed transesterification.
6. The production method according to claim 5, wherein the molar ratio of glycerol tributyrate to glycerol trilaurate is (0.5 to 5): (0.5 to 5);
preferably, the mixing molar ratio is (0.5-1.5): (0.5 to 1.5);
preferably, the transesterification reaction is carried out as follows: mixing tributyrin and trilaurin at 60-70 ℃ in a nitrogen atmosphere, adding immobilized lipase after the tributyrin and the trilaurin are uniformly mixed and are in a liquid state, preserving the temperature for 2-6 h, and removing the immobilized lipase to obtain the butyric-lauric acid mixed structure ester;
preferably, the addition amount of the immobilized lipase is 5-15% of the total weight of the mixture;
preferably, the immobilized lipase is selected from the group consisting of: any one of immobilized Aspergillus oryzae lipase, immobilized Rhizopus oryzae lipase and immobilized Rhizomucor miehei lipase.
7. Use of a mixed structural ester of butyric acid and lauric acid according to any of claims 1 to 4 or prepared by the preparation method according to claim 5 or 6, for the preparation of a feed additive for promoting intestinal health.
8. Use of a mixed structural ester of butyric acid and lauric acid according to any one of claims 1 to 4 or prepared by the preparation method according to claim 5 or 6 for the preparation of a feed additive for regulating the environment of intestinal microorganisms;
preferably, said modulating the gut microbial environment means increasing the abundance of gut microbes;
preferably, the regulation of the gut microbial environment means increasing the abundance of at least one of the genera bifidobacterium, Allobaculum, F16 and CC-115.
9. A feed additive comprising the mixed structural ester of butyric acid and lauric acid according to any one of claims 1 to 4 or the mixed structural ester of butyric acid and lauric acid prepared by the preparation method according to any one of claims 5 or 6.
10. A feed comprising a mixed structural ester of butyric acid and lauric acid according to any one of claims 1 to 4 or a mixed structural ester of butyric acid and lauric acid prepared by the preparation method according to claim 5 or 6.
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| CN106858065A (en) * | 2017-02-28 | 2017-06-20 | 齐鲁工业大学 | Heterozygosis glyceride and production method and application |
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