KR101969467B1 - Improved method for preparing monoacylglycerol by using enzymatic alcoholysis - Google Patents

Abstract

The present invention relates to a method for producing monoacylglycerol using enzymatic alcoholysis, and more particularly, to a method for producing monoacylglycerol by enzymatic alcoholysis, The present invention relates to a method for producing monoacylglycerol which can increase the reaction rate and improve the production yield as compared with the case where such preheating treatment is not carried out.

Description

[0001] The present invention relates to an improved method for preparing monoacylglycerol using enzymatic alcoholysis,

The present invention relates to a method for producing monoacylglycerol using Enzymatic alcoholysis, and more particularly, to a method for producing monoacylglycerol by the enzymatic alcoholysis reaction after heat treatment of the starting material of the enzymatic alcoholysis reaction The present invention relates to a method for producing monoacylglycerol which can increase the reaction rate and improve the production yield as compared with the case where such preheating treatment is not carried out.

Triacylglyceride fats and oils are very widely used in the food industry. Among them, 1,3-dioleoyl-2-palmitoyl glyceride (OPO) Nutritional studies have been carried out as an important component of this study.

Although lipid compositions containing major fatty acids predominantly composed of breast milk are found in many oils and fats of plant origin, almost all plant origin glycerides do not have saturated fatty acids in the 2-position. In contrast, palmitic acid, a significant amount of saturated fatty acid, occupies the 2-position of glycerides in breast milk.

As people's interest in infant health has increased recently, there is an increasing demand for foods that are similar in composition to breast milk.

Innis (Adv. Nutr., 2: 275-283, 2011) describes the structural role of triacylglycerol in relation to infant diets.

However, ordinary powdered milk is a mixture of powdered milk and vegetable oil, and when the oil component of the milk powder is analyzed, palmitic acid is hardly contained in the 2-position.

Accordingly, the application of a high quality breast milk substitute for the addition of 1,3-dioloyl-2-palmitoyl glyceride (OPO) containing 2-position palmitoic acid similar in composition to breast milk Is increasing.

Therefore, techniques for producing OPO at a higher concentration than the conventional method for producing 1,3-dioloyl-2-palmitoyl glyceride (OPO) have become important.

Processes have been known for selectively producing 1,3-dioloyl-2-palmitoyl glyceride (OPO) as a triacylglyceride for replacing breast milk.

Mohamad, et al. (1983, 115, 270-285) reported that 1,3-positions of triacylglycerides were substituted by lipase, 2-palmitoyl glyceride has been mainly studied.

The 1,3-position-specific reaction nature of the triacylglycerides of lipase provides a glyceride backbone containing saturated fatty acids at the 2-position of the triacylglyceride fat, It is important in synthesizing toil glyceride (OPO).

In other words, the higher the content of palmitic acid at the 2-position of the triacylglyceride fat, the higher the quality of 1,3-dioloyl-2-palmitoyl glyceride (OPO) 2-palmitoylglycerol) can be produced with high efficiency.

The present invention relates to a process for preparing monoacylglycerol such as 2-palmitoylglycerol at a high reaction rate and a high production yield in the production of monoacylglycerol using enzymatic alcoholysis The present invention is directed to a method of providing a method for performing the above method.

In order to accomplish the above object, the present invention provides a method for producing monoacylglycerol using an enzymatic alcoholysis, wherein the starting material which has been heat-treated at a temperature higher than the enzymatic alcoholysis reaction temperature is used as an enzyme alcohol Wherein the monoacylglycerol is reacted with a monoacylglycerol monoacylglycerol.

According to one embodiment of the present invention, there is provided a process for preparing a reaction product comprising the steps of (1) providing a pre-reaction mixture comprising a fat component and a solvent comprising triacylglyceride or diacylglyceride, (2) And (3) performing an enzymatic alcoholysis reaction on the pre-reaction mixture heat-treated in the step (2), wherein the step / RTI >

According to another aspect of the present invention, there is provided a process for producing a monoacyl glycerol, which comprises a fat component other than monoacyl glycerol and monoacyl glycerol as a result of an enzymatic alcoholysis reaction of a fat component including triacyl glyceride or diacyl glyceride, : Wherein the molar ratio of the fatty components other than the monoacylglycerol is 1: 1 or more.

According to another aspect of the present invention there is provided a process for the preparation of 2-mono palmitoyl glycerol using (i) enzymatic alcoholysis, wherein the starting material which has been previously heat-treated at a temperature above the enzymatic alcoholysis reaction temperature is used (Ii) introducing an oleoyl group into the 1,3-position of the 2-monopalmitoyl glycerol prepared in the step (i). A process for the preparation of dioloyl-2-palmitoyl glyceride is provided.

According to a further aspect of the present invention there is provided a process for the preparation of 2-monopalmitoyl glycerol prepared by enzymatic alcoholysis of a starting material which has been previously heat-treated at a temperature higher than the enzymatic alcoholysis temperature, Lt; RTI ID = 0.0 > 1, < / RTI > 3-dioleoyl-2-palmitoyl glyceride incorporating the group.

According to the present invention, high-quality monoacylglycerols (for example, glycerol) at a higher yield (for example, at a yield of 20% or more) without affecting the quality of the product compared to the existing method of producing monoacylglycerol using enzymatic alcoholysis , Such as 2-palmitoyl glycerol, can be prepared.

1 is a microphotograph of a pre-reaction mixture (without heat treatment) of an enzymatic alcoholysis used in a comparative example of the present invention.
FIG. 2 is a micrograph of a resultant product obtained by heat-treating the mixture before enzymatic alcoholysis using 50% ethanol for 10 minutes, as used in Example 1 of the present invention. FIG.
FIG. 3 is a micrograph of a resultant product obtained by heat-treating the mixture before enzymatic alcoholysis, which was used in Example 2 of the present invention, at 60 ° C. for 10 minutes.

Hereinafter, the present invention will be described in detail.

The fat component used as a raw material in the method for producing monoacylglycerol of the present invention may be an edible oil containing triacylglyceride, diacylglyceride, or both.

The edible oil may be any oil or fat-containing vegetable oil or animal oil, any oil or ester-exchange oil of the oil, a liquid oil or a solid fat which can be obtained by fractionating the oil, and the like.

Specific examples of the vegetable oil include corn oil, rapeseed oil, soybean oil, cottonseed oil, palm oil, palm oil, rice bran oil, sesame oil, cacao butter, olive oil and combinations thereof. Lard, tallow (crude oil), chicken fat, and combinations thereof. These edible oils may be used singly or in combination of two or more.

In one embodiment of the present invention, palm oil obtained by fractionating palm oil in vegetable oil may be used as the fat component.

Also, in one embodiment, the triacylglyceride and diacylglyceride that may be included in the fat component may be tripalmitoyl glyceride and dipalmitoyl glyceride, respectively.

In one embodiment of the method for producing monoacylglycerol of the present invention, the solvent contained in the pre-reaction mixture of the enzymatic alcoholysis may be one or more of linear aliphatic alcohols. In one embodiment, the number of carbon atoms in the linear aliphatic alcohol can be from 1 to 8, more specifically from 1 to 6, and is selected, for example, from methyl alcohol, ethyl alcohol, propanol, butanol, pentanol, hexanol, And more specifically, ethyl alcohol can be used.

In one embodiment, the fat component used as a raw material in the pre-reaction mixture of the enzymatic alcoholysis may be, for example, 5 parts by weight or more, or 10 parts by weight or more, based on 100 parts by weight of the total mixture before reaction, Not more than 35 parts by weight, not more than 20 parts by weight, or not more than 15 parts by weight. Further, in one embodiment, the amount of the solvent contained in the pre-reaction mixture of the enzymatic alcoholysis may be, for example, 95 parts by weight or less or 90 parts by weight or less based on 100 parts by weight of the total mixture before reaction, Not less than 65 parts by weight, not less than 80 parts by weight, or not less than 85 parts by weight. If the content of the raw fat component in the mixture before the reaction is too small as compared with the content of the solvent, the enzymatic alcoholysis reaction may occur too early or the reaction efficiency may deteriorate. On the contrary, if it is too much, it may not be sufficiently dissolved in the solvent.

In the method for producing monoacylglycerol of the present invention, the starting material of the enzymatic alcoholysis reaction can be obtained by, for example, preheating the reaction mixture containing the raw fat component and the solvent at a temperature higher than the enzymatic alcoholysis reaction temperature, , And an enzymatic alcoholysis reaction is performed on the heat treatment result.

In one embodiment of the present invention, the temperature condition in the pre-reaction heat treatment may be, for example, 45 ° C or higher or 50 ° C or higher, and may be 80 ° C or lower, 70 ° C or 65 ° C or lower. The temperature condition during the heat treatment before the reaction may be most preferably 45 to 65 ° C, and the enzymatic alcoholysis reaction may be usually carried out at 25 to 40 ° C.

In one embodiment of the present invention, the heat treatment time before the reaction may be, for example, 1 minute or longer, 5 minutes or 10 minutes or longer, and 1 hour or shorter, 30 minutes or 20 minutes or shorter.

If the temperature is too low or too short during the pre-reaction heat treatment, if the heat treatment is not sufficiently performed, there is a problem that the heat treatment effect is not generated and the reaction efficiency is lowered. On the contrary, when the temperature is too high or too long, If too much is done, the efficiency of the process may be inferior in using thermal energy.

In one embodiment of the invention, the heat-treated mixture prior to the enzymatic alcoholysis reaction has particles dispersed in a solvent, the average particle size of the particles being from 0.01 to 65 microns, more specifically from 0.1 to 65 microns have.

In one embodiment of the present invention, the result of the heat treatment before the reaction under the above conditions is lowered to the enzymatic alcoholysis reaction temperature, and then the alcoholysis enzyme is added thereto and mixed to proceed the enzyme reaction. As the enzyme, known enzymes known to be useful for alcoholysis reaction can be used without any particular limitation. Specifically, Candida antak urticae (Candida Antarctica B), Thermo My process called leakage No suspension (Thermomyces lanuginose), Perth mieyi separation tank (Rhizomucour miehei , Rhizopus delemar , Mucormiehei , Alcaligenes sp . , Aspergillus niger , Candida cylindraces , Bacolieria sephacia, Burkholderia but are not limited to, lipase derived from microorganisms selected from the group consisting of cepacia , Geotricum candidum and combinations thereof.

In one embodiment of the present invention, the amount of the enzyme used may be, for example, 5 parts by weight or more, 10 parts by weight or 15 parts by weight or more, and 40 parts by weight or less, 30 parts by weight or less, or 25 parts by weight or less. If the amount of the enzyme used is too small as compared with the total amount of the pre-reaction mixture, there may be a problem that the reaction does not occur and the efficiency is inferior. On the other hand, if the amount is too much, the reaction proceeds rapidly and the reaction can not be controlled. There may be a problem that the activity of the enzyme decreases rapidly.

According to the present invention, monoacylglycerol can be produced at an improved yield (for example, a yield higher than 20%) without affecting the reaction time or quality compared to the existing method of producing monoacylglycerol using enzymatic alcoholysis. Can be manufactured.

In one embodiment, the monoacyl glycerol produced in accordance with the present invention may be palmitoyl glycerol, such as 2-palmitoyl glycerol.

According to another aspect of the present invention, there is provided a process for producing a monoacyl glycerol, which comprises a fat component other than monoacyl glycerol and monoacyl glycerol as a result of an enzymatic alcoholysis reaction of a fat component including triacyl glyceride or diacyl glyceride, : Wherein the molar ratio of the fatty components other than the monoacylglycerol is 1: 1 or more.

The fat composition of the present invention can be obtained according to the above-described method for producing monoacylglycerol of the present invention.

In the fat composition of the present invention, the molar ratio of monoacylglycerol to the fatty components other than monoacylglycerol is 1: 1 or higher, more specifically 2: 1 or higher, 3: 1 or higher, 4 : 1 or more, or 5: 1 or more, and more specifically 3: 1 to 10: 1, 4: 1 to 9: 1, or 5: 1 to 8:

In one embodiment, the fat component other than the monoacylglycerol may include triacylglyceride, diacylglyceride, or a combination thereof.

According to another aspect of the present invention there is provided a process for the preparation of 2-mono palmitoyl glycerol using (i) enzymatic alcoholysis, wherein the starting material which has been previously heat-treated at a temperature above the enzymatic alcoholysis reaction temperature is used (Ii) introducing an oleoyl group into the 1,3-position of the 2-monopalmitoyl glycerol prepared in the step (i). A process for the preparation of dioloyl-2-palmitoyl glyceride is provided.

The starting materials, the heat treatment conditions and the enzymatic reactions in the step (i) are as described above.

As the source of the oleoyl group in the step (ii), oleic acid or an oleic acid derivative such as oleic acid C1-C4 alkyl ester (e.g., oleic acid ethyl ester), or a combination thereof may be used.

There is no particular limitation on the method for introducing the oleoyl group into the 1,3-position of the 2-monopalmitoyl glycerol in the step (ii), and for example, a position-specific esterification reaction using an enzyme may be used, It is not.

According to another aspect of the present invention, there is provided a process for preparing a 2-mono-palmitoyl glycerol, which comprises subjecting a starting material which has been previously heat-treated at a temperature higher than an enzymatic alcoholysis reaction temperature to 1,3- There is provided a milk powder composition comprising 1,3-dioleoyl-2-palmitoyl glyceride incorporating an oleoyl group.

Hereinafter, the present invention will be described more specifically with reference to Examples, Comparative Examples and Experimental Examples. However, it should be understood that the present invention is not limited thereto.

[Examples 1 to 2 and Comparative Example 1]

Preparation of monoacylglycerol

Monoacylglycerol was prepared using the ingredients shown in Table 1 below in the respective blending amounts. First, the retentate palm fractionation oil and the solvent were placed in a reaction vessel, the temperature was raised to 40 ° C, and heat treatment was performed for 10 minutes under the temperature conditions shown in Table 1. After the heat treatment, the temperature of the resultant was lowered to 40 ° C, and the enzyme was added to perform enzymatic alcoholysis reaction.

Evaluation of monoacylglycerol content

The products prepared in each of the Examples and Comparative Examples were taken at time intervals and the amount of monoacylglycerol (Ce 5-86) was measured by gas chromatography using the AOCS Official Method. The results are shown in Table 2.

[Description of raw materials used]

Novozyme 435: Immobilized lipase from Candida antartica B

Ethyl alcohol: Solvent

Palm fractionation: Fractional oil fractionation of palm oil in vegetable oil (IV 17)

Evaluation of crystalline state of reactants

In the Comparative Examples and Examples 1 and 2, the state of the solvent in the heat-treated mixture before the enzyme reaction was photographed through a microscope and shown in FIGS. 1 to 3, respectively.

The average particle size of the particles dispersed in the solvent of the heat-treated mixture in Comparative Examples and Examples 1 and 2 was measured with a particle size analyzer and is shown in Table 3.

It can be seen from Figs. 1 to 3 that the reaction material of Example 2 after heat treatment has a smaller surface area due to a smaller particle size as compared with Comparative Example and Example 1. Fig. That is, when heat treatment is performed on the raw material before the enzyme reaction, variation in the production efficiency of monoacylglycerol according to the crystal state of the raw material can be reduced, and the reaction efficiency can be increased.

Claims (13)

(1) providing a pre-reaction mixture comprising a fat component and a solvent comprising triacylglyceride or diacylglyceride,
(2) heat-treating the pre-reaction mixture in advance at a temperature higher than the enzymatic alcoholysis reaction temperature, and
(3) lowering the temperature of the pre-reaction mixture heated in step (2) to an enzymatic alcoholysis reaction temperature, and introducing an alcoholysis enzyme to perform an enzymatic alcoholysis reaction;
Process for producing monoacylglycerol. [Claim 2] The method according to claim 1, wherein the fat component comprising triacylglyceride or diacylglyceride is selected from the group consisting of vegetable fat, animal fat, curing oil or ester exchange oil of the fat, liquid or solid fat obtainable by fractionating the fat, Of the monoacylglycerol. The method according to claim 2, wherein the vegetable oil is selected from corn oil, rapeseed oil, soybean oil, cottonseed oil, palm oil, palm oil, rice bran oil, sesame oil, cacao butter, olive oil and combinations thereof, Fats, and combinations thereof. ≪ Desc / Clms Page number 24 > The process for producing monoacylglycerol according to claim 1, wherein the solvent is a linear aliphatic alcohol. 5. The process according to claim 4, wherein the linear aliphatic alcohol is selected from methyl alcohol, ethyl alcohol, propanol, butanol, pentanol, hexanol and combinations thereof. The process for producing monoacylglycerol according to claim 1, wherein the temperature higher than the enzymatic alcoholysis reaction temperature is 45 ° C or higher. The process for producing monoacylglycerol according to claim 1, wherein the monoacylglycerol is palmitoyl glycerol. The method according to claim 1, wherein the result of the enzymatic alcoholysis reaction comprises fats other than monoacylglycerol and monoacylglycerol, wherein the molar ratio of monoacylglycerol to fats other than monoacylglycerol is 1: 1 or greater , A method for producing monoacylglycerol. 9. The method according to claim 8, wherein the fat other than the monoacylglycerol comprises triacylglyceride, diacylglyceride or a combination thereof. (i) In the preparation of 2-monopalmitoyl glycerol using enzymatic alcoholysis, the temperature of the starting material which had been previously heat-treated at a temperature higher than the enzymatic alcoholysis reaction temperature is lowered to the enzymatic alcoholysis reaction temperature , Introducing an alcoholysis enzyme to proceed an enzymatic alcoholysis reaction, and
(ii) introducing an oleoyl group into the 1,3-position of the 2-mono palmitoyl glycerol prepared in step (i)
A process for preparing 1,3-diolureyl-2-palmitoyl glyceride. 11. The process according to claim 10, wherein the source of the oleoyl group is oleic acid, an oleic acid derivative, or a combination thereof. delete delete

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