KR100540875B1 - Fat composition of high degree of purity diglyceride comprising conjugated linoleic acid and preparation method of the same - Google Patents

Abstract

The present invention relates to a high-purity diglyceride fat and oil composition comprising a conjugated linoleic acid and a method for preparing the same, and more specifically, (a) 85 to 99.9 weight percent diglyceride comprising 0.1 to 80 wt% of conjugated linoleic acid; And (b) monoglycerides, triglycerides, or mixture residues thereof, and a preparation method of the same.

The high-purity diglyceride fat and oil composition comprising the conjugated linoleic acid of the present invention can be utilized as a food additive due to the effects of anti-cancer, reduced body fat, immune enhancer, or diabetes prevention and treatment of conjugated linoleic acid, and also a method of preparing the same. This is simple and productivity is excellent.

Fats and oils, diglycerides, linoleic acid, conjugated linoleic acid, lipase, fatty acids

Description

FACT COMPOSITION OF HIGH DEGREE OF PURITY DIGLYCERIDE COMPRISING CONJUGATED LINOLEIC ACID AND PREPARATION METHOD OF THE SAME

The present invention relates to a high-purity diglyceride fat and oil composition comprising a conjugated linoleic acid and a method for preparing the same, more particularly, the manufacturing method is simple and excellent in productivity, and at the same time, anti-cancer, body fat reduction, immune enhancement, Or it relates to a method for producing a high-purity diglyceride fat and oil composition comprising conjugated linoleic acid or conjugated linoleic acid that can impart functionality by combining conjugated linoleic acid or an isomer thereof having the effect of preventing and treating diabetes.

Lipase is an enzyme that hydrolyzes oils and fatty acid esters. However, it is known to synthesize glycerin or esters from fatty acids and glycerin or fatty acids and alcohols by causing transesterification under certain conditions (J. Gen. Appl. Microbiol., 10, 13-22,1964; Proc. IV. IFS: Ferment.Technol.Today, 315-320, 1972, Society of Fermetation Technolgy Japan; Bichim. Biophys.Acta, 489, 415-422, 1977, etc.).

Glycerides synthesized by the transesterification reaction are monoglyceride (MG), diglyceride (1,2-DG, 1,3-DG, 2,3DG), and depending on the degree of substitution of the hydroxy group of glycerin, and Triglyceride (TG).

Diglyceride is an oil-fat composition in which fatty acid is bound to glycerin in the first, second, or first and third positions by transesterification of fatty acid and glycerin, and is treated separately from general oils and fats called triglycerides. .

In recent years, diglycerides have the same process of digesting and absorbing the effects of the body compared to normal neutral oils, but since they are hardly resynthesized into triglycerides, the physiological effect does not increase the amount of triglycerides in the blood and does not accumulate body fat even if ingested. It is found that there is, and the research on this is ongoing.

As a study on the method for preparing such diglycerides, JP-A-6-343481 discloses a diglyceride content of 85% by reacting solid fats with lipases originating from glycerin, Pseudomonas microorganisms, etc. Genie discloses a manufacturing method. However, the above method has disadvantages of forming solid fats and oils at room temperature and difficulty in preparing diglycerides having a purity of 85% or more when using liquid fats.

In addition, Japanese Laid-Open Patent Publication No. 64-71495 and Japanese Patent Laid-Open No. H11-123097 are two-step reactions of hydrolyzing fats and oils with 1,3-position specific lipase, and then resynthesizing the degraded fatty acid and glycerin. It discloses a method for producing a fat and oil composition containing a diglyceride of purity 80% through. However, this method has a problem in that it has a complicated route to be synthesized with fatty acids by dehydrating glycerin after the hydrolysis reaction.

In order to overcome the above problems, Korean Patent Application No. 2001-0002974 relates to a method for preparing a fat composition of 60% or more of diglyceride using water and 1,3 specific lipase or nonspecific lipase based on 100 parts by weight of fat or oil. It is starting. However, the above method has a problem in that the free fatty acid content is increased due to the side effect of hydrolysis of fatty acids when water is present upon completion of the diglyceride reaction having a purity of 60% or more, and the free fatty acid is removed. There is a problem that 40% by-products must be separated and processed again.

Therefore, there is a need for further research on a method of preparing a high-purity diglyceride fat and oil composition having a simple manufacturing method and excellent productivity.

Meanwhile, conjugated linoleic acid (CLA) is a conjugated isomer of essential fatty acid linoleic acid (LA), which is found in trace amounts in ruminant milk or muscle. It is a natural fatty acid component. CLA means a generic name for the positional and geometric isomers of linoleic acid with conjugated double bonds in the cis or trans configuration. Cis- 9, trans- 11 octadecadienoic acid and trans- 10, cis- 12 octadecadienoic acid, which exhibit functionality, are referred to as CLA. In addition, CLA is associated with decreased incidence of atherosclerosis (Artery. 1997. 22: 266-277), improved immune function (J. Nut. 1999. 129: 32-38), and anticancer activity (1997. 17: 969-973). ), Growth promotion (J. Nut. 2000. 130: 2981-2989) and excellent treatment effect for diseases such as diabetes, obesity through body fat reduction (Am. J. Physiol. 1998. 275: R667-R672) It is also known to suppress. Due to these characteristics, CLA can be usefully used as an active ingredient in functional foods and pharmaceuticals.

In order to solve the problems of the prior art as described above, the present invention provides a high-purity diglyceride fat and oil composition comprising conjugated linoleic acid that can impart anti-cancer, reduce body fat, enhance immune, or prevent and treat diabetes. It aims to do it.

Another object of the present invention is to provide a high-purity diglyceride fat and oil composition comprising conjugated linoleic acid, which is imparted with anticancer properties, reduced body fat, enhances immunity, or prevents and treats diabetes, and which is simple in production and has high productivity. It is to provide a manufacturing method.

It is another object of the present invention to provide a food additive excellent in anticancer properties, body fat reduction, immune enhancement, or diabetes prevention and treatment effect.

In order to achieve the above object, the present invention (a) 85 to 99.9% by weight of a diglyceride containing 0.1 to 80% by weight of conjugated linoleic acid; And (b) residues of monoglycerides, triglycerides or mixtures thereof.

The invention also relates to (a) monoglycerides; Conjugated linoleic acid; And mixing the fats and oils, fatty acids or mixtures thereof and stirring at 10 to 200 rpm; And (b) exchanging the stirred mixture of step (a) for 1 to 10 hours at 200 to 250 ° C. under a reduced pressure of 0.001 to 0.5 torr, to prepare a high purity diglyceride fat and oil composition comprising conjugated linoleic acid. Provide a method.

The invention also comprises the steps of (a) mixing monoglycerides, conjugated linoleic acid, lipase and stirring at 10 to 200 rpm; And (b) exchanging the stirred mixture of step a) at a stirring speed of 10 to 200 rpm, at a temperature of 30 to 60 ° C., at a pressure of 0.001 to 0.5 torr for 1 to 10 hours, and including high-conjugated linoleic acid. Provided is a method for preparing a diglyceride fat or oil composition.

The present invention also provides a food additive comprising the high purity diglyceride fat and oil composition.

Hereinafter, the present invention will be described in detail.

The inventors noted that the anti-cancer, reduced body fat, immune enhancement, or diabetes prevention and treatment of conjugated linoleic acid may be useful as a food additive as a high-purity diglyceride fat and oil composition comprising such conjugated linoleic acid. The present invention has been completed by focusing on the present invention.

In addition, the present inventors while studying a method for producing a high-purity diglyceride fat and oil composition having a simple production method and excellent productivity, monoglycerides; Conjugated linoleic acid; And mixing the fats and oils, fatty acids or mixtures thereof and stirring at 10 to 200 rpm and exchanging the stirred mixtures at 200 to 250 ° C. under a reduced pressure of 0.001 to 0.5 torr for 1 to 10 hours or monoglycerides, conjugated linoleic acid. After mixing lipase and stirring at 10 to 200 rpm, the stirred mixture was exchanged for 10 to 200 rpm at a stirring speed of 10 to 200 ° C. for 1 to 10 hours under a reduced pressure of 0.001 to 0.5 torr. It was confirmed that the high-purity diglyceride fat and oil composition provided with anti-cancer properties, reduced body fat, immune enhancement, or diabetes prevention and treatment, and completed the present invention based on this.

In the high purity diglyceride fat and oil composition comprising the conjugated linoleic acid of the present invention, the content of the conjugated linoleic acid in the diglyceride is preferably 0.1 to 80% by weight. The reason for the specific limitation of the content of conjugated linoleic acid in the present invention is that if the content of linoleic acid is less than 0.1% by weight, the oil or fat composition prepared by the low content of conjugated linoleic acid is anticancer, reduced body fat, immune enhancer, or diabetes prevention and treatment. There is a problem that no effect can be imparted to the effect, and if it exceeds 80% by weight due to the high cost of conjugated linoleic acid there is a problem that the cost of manufacturing high-purity diglyceride composition is not economical.

The present inventors have invented two methods of preparing a diglyceride fat and oil composition comprising the conjugated linoleic acid of the present invention described above.

The first method is monoglycerides; Conjugated linoleic acid; And a fat or oil, a fatty acid or a mixture thereof, followed by stirring, followed by exchange reaction of the stirred mixture.

(a) monoglycerides; Conjugated linoleic acid; And fat, mixing and stirring fatty acids or mixtures thereof

In more detail, the reaction conditions are first monoglycerides; Conjugated linoleic acid; And fats and oils, fatty acids or mixtures thereof. Monoglyceride in this stirring step; Conjugated linoleic acid; And 35 to 65 parts by weight and 20 to 80 parts by weight of the conjugated linoleic acid and the fats and oils or the mixture thereof in order of 100 parts by weight of the fats and oils, fatty acids or mixtures thereof, respectively.

 In addition, the molar ratio of monoglyceride and fats and oils, fatty acids or mixtures thereof is preferably 6: 4 to 8: 2.

In the reaction conditions, the mixed monoglycerides; Conjugated linoleic acid; And it is preferable to stir the fats and oils, fatty acids or mixtures thereof at 10 to 200 rpm, if the stirring speed is less than 10rpm there is a problem that the reaction speed is slow due to a weak stirring power, there is a problem that the product color is poor when it exceeds 200rpm Not desirable

(b) exchange reaction step of the stirred mixture

In addition, the exchange of the stirred mixture is preferably carried out for 1 to 10 hours at 200 to 250 ℃, 0.001 to 0.5torr reduced pressure. As for the exchange reaction temperature, 200-230 degreeC is more preferable. If the exchange reaction temperature is less than 200 ℃, there is a problem that the reaction rate is slow, and if it exceeds 250 ℃, the reaction rate is too fast to control the content is not preferable, and if the decompression condition is less than 0.001torr monoglycerol during distillation There is a problem in that dilide and diglyceride are distilled together, and when it exceeds 0.5torr, there is a problem that monoglyceride distillation is difficult, which is not preferable.

As the fats and oils used in the preparation of the high-purity diglyceride fat and oil composition containing the conjugated linoleic acid, soybean oil, rapeseed oil, cottonseed oil, jade oil, olive oil, palm oil, palm kernel oil, palm oil, safflower oil, and mixtures thereof are preferable. As saturated or unsaturated fatty acids of 24 to 24, oleic acid, soybean fatty acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, linolenic acid, Docosahexaenoic Acid (DHA) and mixtures thereof are preferred, alone. It may be used or a mixture of two or more and the type is not particularly limited.

The second method is a method of mixing and stirring monoglyceride, conjugated linoleic acid and lipase, and then exchanging the stirred mixture.

The second method is described in detail as follows.

(a) mixing and stirring monoglycerides, conjugated linoleic acid, lipase

This step involves mixing and stirring monoglycerides, conjugated linoleic acid, and lipases.

The conjugated linoleic acid may be prepared by isomerizing a monoglyceride containing 1 to 80 parts by weight of linoleic acid based on 100 parts by weight of monoglyceride.

The conjugated linoleic acid is preferably included 1 to 80 parts by weight based on 100 parts by weight of monoglycerides. If the content is less than 1 part by weight, there is a problem that the functionality is lowered. If the content exceeds 80 parts by weight, there is a problem that the economic efficiency is lowered.

The lipase is not particularly limited, but lipozymes, 1,3-position specific lipases, non-position specific lipases, lycopus having 1,3-position specificity, and the like, and more preferably 1,3 Position specific or non-position specific lipase.

The lipase is preferably included in 0.1 to 20 parts by weight based on 100 parts by weight of monoglycerides. If the content is less than 0.1 parts by weight, the reaction conversion rate is significantly lowered, and if it exceeds 20 parts by weight, there is a problem that the economic efficiency is lowered.

After uniformly mixing the above monoglyceride, conjugated linoleic acid, and lipase, it is preferable to stir at 10 to 200 rpm, particularly preferably at 150 rpm.

(b) exchange reaction step

This step is a step of exchanging the stirred mixture of step a) at a stirring speed of 10 to 200 rpm and a temperature of 40 to 80 ° C. for 1 to 10 hours.

The exchange reaction is preferably carried out at a stirring speed of 10 to 200 rpm, in particular at 150 rpm, and preferably at a temperature of 30 to 60 ° C, in particular at 50 ° C. If the stirring speed is less than 10rpm there is a problem that the reaction speed is slow due to the weak agitation force, if the reaction speed is faster than 200rpm, it is difficult to control the reaction. In addition, if the reaction temperature is less than 40 ℃ there is a problem that the reaction is slow, if it exceeds 80 ℃ the reaction is fast but there is a problem that the enzyme and the like may be affected by heat. In addition, when the reaction time is less than 1 hour, the conversion rate is not good when the reaction time is short.

After the method for preparing a high purity diglyceride fat or oil composition comprising conjugated linoleic acid according to the two methods described above, the monoglyceride, triglyceride, or fatty acid is removed from the fat or oil composition by molecular distillation, thereby diglyceride is at least 80 The fat or oil composition containing the weight% can be obtained.

The oil-fat composition of the present invention prepared according to the above preferably comprises 80 to 99.9% by weight of diglycerides containing 0.1 to 80% by weight of conjugated linoleic acid. Although very small amounts of triglycerides or monoglycerides may be included, it is more desirable to increase the purity of the diglycerides through a molecular distillation step.

As described above, the manufacturing method according to the present invention is not only a simple manufacturing process and excellent productivity, but also conjugated linoleic acid having a strong effect of anti-cancer, body fat reduction, immune enhancement, or diabetes prevention and treatment, and functional Is given.

In another aspect, the present invention provides a food additive comprising a high-purity diglyceride fat and oil composition prepared as an active ingredient, the food additive (particularly, food additives for diet) is anti-cancer, body fat reduction, immune enhancing , Or diabetes prevention and treatment effect is excellent.

Hereinafter, preferred examples are provided to help understanding of the present invention, but the following examples are merely to illustrate the present invention, and the scope of the present invention is not limited to the following examples.

(Example)

(Example 1)

1300 g of monoglyceride, 20 g of conjugated linoleic acid, and 5 g of lipase were mixed in a 3 L round flask equipped with a stirrer, and stirred and stirred at a stirring speed of 150 rpm, followed by reaction at a stirring speed of 150 rpm at 60 ° C. for 10 hours. To prepare a diglyceride fat and oil composition comprising conjugated linoleic acid.

 (Example 2)

After mixing monoglyceride 1200 g, conjugated linoleic acid 40 g, and lipase 5 g in a 3 l round flask equipped with a stirrer, stirring and stirring at 150 rpm stirring speed, the reaction was carried out for 10 hours at a stirring speed of 150 rpm at 60 ℃. To prepare a diglyceride fat and oil composition comprising conjugated linoleic acid.

(Example 3)

1000 g of monoglyceride, 80 g of conjugated linoleic acid, and 5 g of lipase were mixed in a 3 l round flask equipped with a stirrer, and stirred and stirred at a stirring speed of 150 rpm, followed by reaction at a stirring speed of 150 rpm at 60 ° C. for 2 hours. To prepare a diglyceride fat and oil composition comprising conjugated linoleic acid.

(Example 4)

30 g of monoglyceride, 3 g of soybean fatty acid, 2 g of oleic acid, and 65 g of conjugated linoleic acid were added to a 3 L flask and stirred slowly for 1 hour when reaching 250 ° C. under reduced pressure, followed by distillation by molecular distillation at 250 ° C. under reduced pressure of 0.04torr. To prepare a diglyceride fat and oil composition. The content of monoglyceride, diglyceride, triglyceride and conjugated linoleic acid bound to diglyceride of the diglyceride fat and oil composition prepared in Example 4 was measured and shown in Table 1 below.

division Content (% by weight) Monoglycerides 0.5%  60% of conjugated linoleic acid 1,2-diglyceride 30% 1,3-diglyceride 54.6% Triglycerides 14.9%

(Example 5)

The oil-fat compositions prepared in Examples 1 to 3 were molecularly distilled until monoglycerides and triglycerides were all distilled using a process for producing diglycerides in ilshin emulsification, and then diglycerides (1,2- Diglycerides, 1,3-diglycerides) and the content of conjugated linoleic acid bound to diglycerides were measured and the results are shown in Table 2 below.

division Example 1 Example 2 Example 3 Monoglycerides One% Conjugated linoleic acid 14.5% 0.5% Conjugated linoleic acid 34% 0.3% Conjugated linoleic acid 75.9% 1,2-diglyceride 29% 30% 27% 1,3-diglyceride 55.6% 54.6% 58% Triglycerides 14.4% 14.9% 14.7%

 (Unit: weight%)

According to the present invention, not only the manufacturing method is simple and excellent in productivity, but also high purity that can impart functionality by combining conjugated linoleic acid which has anti-cancer properties, body fat reduction, immune enhancement, or a powerful effect of preventing and treating diabetes. Diglyceride fat and oil composition can be prepared, the high-purity diglyceride fat and oil composition prepared as described above is the body fat of our body as a food additive having the effect of anti-cancer, body fat reduction, or immuno-enhancing, diabetes prevention and treatment As it is not digested and absorbed, it can be used as a food additive for diet.

Claims (10)

(a) 85 to 99.9 weight percent diglycerides comprising 0.1 to 80 weight percent conjugated linoleic acid; And (b) residues of monoglycerides, triglycerides or mixtures thereof High purity diglyceride fat and oil composition comprising a. (a) monoglycerides; Conjugated linoleic acid; And mixing the fats and oils, fatty acids or mixtures thereof and stirring at 10 to 200 rpm; And (b) exchanging the stirred mixture of step (a) for 1 to 10 hours at 200 to 250 ° C. under a reduced pressure of 0.001 to 0.5 torr; Method for producing a high purity diglyceride fat and oil composition comprising a conjugated linoleic acid comprising a. The method of claim 2, The molar ratio of the monoglycerides and fats and oils, fatty acids or mixtures thereof is 6: 4 to 8: 2 method of producing a high purity diglyceride fat and oil composition comprising conjugated linoleic acid. The method of claim 2, The temperature of the (b) exchange reaction is a method for producing a high purity diglyceride fat and oil composition comprising conjugated linoleic acid, characterized in that 200 to 230 ℃. The method of claim 2, The fats and oils, soybean oil, rapeseed oil, cottonseed oil, jade oil, olive oil, palm oil, palm kernel oil, palm oil, safflower oil and a mixture thereof, a method for producing a high-purity diglyceride fat and oil composition comprising linoleic acid. The method of claim 2, The fatty acid is a saturated or unsaturated fatty acid having 2 to 24 carbon atoms, oleic acid, soy fatty acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, linolenic acid, Docosahexaenoic Acid (DHA) and mixtures thereof A method for producing a high purity diglyceride fat and oil composition comprising conjugated linoleic acid, characterized in that selected from the group consisting of. (a) mixing monoglycerides, conjugated linoleic acid, lipase and stirring at 10 to 200 rpm; And (b) a high purity comprising conjugated linoleic acid comprising the step of exchanging the stirred mixture of step (a) for 1 to 10 hours at a stirring speed of 10 to 200 rpm, a temperature of 30 to 60 ° C, and a pressure of 0.001 to 0.5 torr Process for the preparation of diglyceride fats and oils composition. The method of claim 7, wherein (a) mixing 1 to 80 parts by weight of conjugated linoleic acid and 0.1 to 20 parts by weight of lipase with respect to 100 parts by weight of monoglyceride and stirring at 10 to 200 rpm; (b) exchanging the stirred mixture of step (a) for 1 to 10 hours at a stirring speed of 10 to 200 rpm, a temperature of 30 to 60 ° C, and a pressure of 0.001 to 0.5 torr; And (c) molecular distillation of the reaction mixture of step (b) Method for producing a high purity diglyceride fat and oil composition comprising a conjugated linoleic acid, characterized in that it comprises a. The method of claim 7, wherein Wherein the lipase of step (a) is selected from the group consisting of lipozymes, 1,3-position specific lipases, non-position specific lipases, lysopus with 1,3-position specificity, and geotriose with unsaturated fatty acid specificity A process for producing a high purity diglyceride fat and oil composition comprising conjugated linoleic acid, characterized in that. A food additive comprising the high purity diglyceride fat or oil composition of claim 1 as an active ingredient.