KR101342110B1 - Process for Preparing Edible Oil Containing Ajoene from Garlic - Google Patents

Abstract

The present invention comprises the steps of preparing any one or more allicin (allicin) containing garlic material selected from garlic ground, garlic juice, garlic dry powder and garlic extract; Mixing the allicin-containing garlic material with milk fat; And a step of heating the mixture of the allicin-containing garlic material and the milk fat and reacting the same. It is possible to produce azoene at a content of more than two times higher.

Description

Process for Preparing Edible Oil Containing Ajoene from Garlic}

The present invention relates to a method for producing garlic oil products containing azoene from garlic using animal lipids, in particular milk fat, and to a health functional food using the same as an active ingredient.

Garlic ( Allium sativum L.) is a bulbous crop belonging to the genus Liliumaceae ( Allium ), and many researchers have recently reported that it has various pharmacological physiological activities such as cancer prevention, blood circulation disorder prevention and antioxidant activity. . The main component that shows the pharmacological physiological activity of garlic is S-alyl, also known as allin, which is one of S-alk (en) yl-L-cysteine sulfoxides. S-allyl-L-cysteine sulfoxide is produced by the polymerization and decomposition of allicin and allicin produced by the action of the enzyme alinase, which is an enzyme in garlic. and various sulfur compounds such as ajoene) and vinyl dithiins (Lawson et al. Planta . Med . 57: 363-370 (1991)). Azoene (E, Z-4,5,9-trithiadodeca-1,6,11-triene-9-oxide) is produced from pure allicin and has the advantage of greater chemical stability than allicin. Azoene has two isomers, in which Chemical Formula 1 is Z-Azoene ( cis form), and Chemical Formula 2 is E-Azoene ( tran s form).

Formula 1

(2)

Azoene is produced by grinding garlic and reacting it with an organic solvent or cooking oil, which was first reported by Block et al. ( J. Am . Chem . Soc . 106: 8295-8296 (1984)). According to Block's study, azoene has the effect of inhibiting all factors related to platelet coagulation and its effect is the same as that of aspirin inhibiting platelet aggregation ( Sci . Am . 252: 94-99 (1985). )).

The biological activity of azoene prevents thrombosis, includes antimicrobial activity (Stenier M. et al. J. Nutr . 131: 980S-984S (2001)), 3-hydroxy-3-methyl-glutaryl-CoA (HMG-CoA) reduces cholesterol biosynthesis through inhibition of reductase (Rolf et al. Biochimica et Biophysica Acta 1213: 57-62 (1994). Garlic affects lipid metabolism in the body and has been reported to reduce blood lipid levels as well as inhibit blood circulation disorders caused by atherosclerosis, thrombosis, and vascular contraction, which are direct causes of hypertension, heart disease, and stroke.

Apitz-Castro et al. ( Biochim . Biophys . Acta . 1094: 269-280 (1991)) reported the mechanism of inhibition of platelet coagulation of azoene as a therapeutic agent for circulatory diseases such as pulmonary disease, atherosclerosis and hyperlipidemia. Showed the possibility. Azoene also inhibits the action of carcinogen Aflatoxin B and DNA (Tadi et al. Cancer Letters 59: 89-94 (1991)) and cytotoxic activity against tumor cells (Scharfenberg et al. Cancer Letters 53: 103-108 (1990)).

In addition, antifungal / antifungal action of azoene (Yoshida et al. Appl . Environ . Microbiol . 53: 615-617 (1987)), antiviral effect (Werber et al. Planta Med . 58: 417-423 (1992)), and have been reported to be effective against AIDS (Tatarintsev et al. Int . Conf . AIDS 8: 19-24). Azoene has an effect similar to that of 5-fluorocytosine, an antibacterial / antibacterial agent.

Azoene does not exist in general processed products such as raw garlic, garlic stalk and dried garlic and is generally produced when mixed with low polar organic solvents or fats and oils. And time).

Lawson obtained 60 to 148 ㎍ / g of azoene from garlic juice obtained by adding garlic to vegetable oils, and E- azoene is always produced more than Z-azoene, and E type is generally more than twice as high as Z type. Reported.

In Japanese Patent Laid-Open No. 62-129224, a process of extracting azoene by mixing garlic with an organic solvent of pH 2-6 such as ethyl alcohol and methyl alcohol and heating to 40-90 ° C. is disclosed. In this process, only about 900 μg of azoene per kilogram of garlic is extracted, and a large amount of garlic is required to obtain a large amount of azoene. This low efficiency azoene production process is insufficient for use in food and medicine.

Japanese Patent Application Laid-Open Nos. 8-84570 and 11-318377 are crushed by adding water to garlic and adjusting the pH to 6 to 8, then mixing the edible oils and maintaining the temperature at 0 to 50 DEG C. 417 mg to 503 g of azoene was obtained per 404 mg or 1 g of fats and oils, but vegetable fats such as neutral medium-chain fatty oil (MCT oil), jade oil, and salad oil were used. It was only.

The present invention relates to a method for producing a garlic oil product containing azoene from garlic using animal lipids, in particular milk fat, and to a health functional food using the same as an active ingredient.

The present inventors endeavored to develop a process for optimizing a method for maximizing the production of azoene, which is a functional or medicinal active ingredient in garlic. As a result, the present inventors have developed a process for producing azoene using animal lipids, in particular, milk fat, and have completed the present invention by establishing a process capable of producing azoene at a yield more than twice that of conventional techniques.

Accordingly, it is an object of the present invention to provide a method for producing garlic oil containing azoene and azoene-containing garlic oil prepared therefrom.

Another object of the present invention to provide a health functional food containing the azoene-containing garlic oil as an active ingredient.

Other objects and advantages of the present invention will become more apparent from the following detailed description of the invention, claims and drawings.

The present invention comprises the steps of preparing any one or more allicin (allicin) containing garlic material selected from garlic puree, garlic juice, dried garlic powder and garlic extract; Mixing the allicin-containing garlic material with milk fat; And heating the mixture of allicin-containing garlic material and milk fat.

In the present invention, "garlic oil" is a milk product in the form of a semi-finished or finished product containing a garlic-derived component or a substance derived from a garlic-derived component, means a milk-containing product other than butter prepared by moving and pressing milk fat, and "garlic "Pure" means a garlic pulverized by crushing the raw garlic by a method such as pressing or physical crushing, "Garlic juice" means a juice obtained from the garlic crushed, or by filtering or centrifuging the garlic juice Refers to the liquid portion produced when the solid-liquid separation, "garlic juice residue" refers to the residue or solid phase remaining after producing the juice, "garlic extract" is the garlic puree, garlic juice juice, garlic juice residue or dried Garlic is extracted with water, a lower alcohol having 1 to 4 carbon atoms or a mixed solvent thereof. Lower alcohols having 1 to 4 carbon atoms include methanol, ethanol, butanol, propanol, and the like, preferably methanol or ethanol, and more preferably ethanol. Garlic extract is a garlic enzymatic extract obtained by reacting garlic ingredients, especially garlic juice residues, with water containing any one or more enzymes selected from pectin and cellulose degrading enzymes to make the best use of allicin contained in garlic ingredients. It includes.

When the garlic puree is mixed with fat or oil directly to produce azoene, the particle size of the garlic puree is preferably manufactured to 20 mesh or less. Also, when the garlic dry powder is mixed with edible oil and fat to produce azoene, the powder particles The size of is preferably 60 mesh or less.

Garlic puree, garlic juice, dried garlic powder of the present invention and any one or more allicin (allicin) containing garlic material selected from garlic extract is preferably 2 to 10 mg / g, more preferably on a dry weight basis 4-10 mg / g of allicin.

In the present invention, the milk fat which is reacted with the allicin-containing garlic material is a concentrated fat component in the milk of an animal, and is a living body including fat, sterol, monoglyceride, diglyceride, triglyceride, phospholipid and fatty acid comprehensively. It means a molecule and does not need to be 100% pure milk fat, but contains 30 to 99% by weight, more preferably 32 to 90% by weight fat, even more preferably 80 to 90% by weight. The milk fat used in the present invention may be fresh cream or butter, preferably butter, and may be derived from milk of cow, goat, sheep, horse, camel, donkey, deer, buffalo or yak.

The fatty acid composition of milk fat used in the present invention includes saturated fatty acids and unsaturated fatty acids as follows (National Research Council, 1976, Fat Content and Composition of Animal Products, Printing and Publishing Office, National Academy of Science, ISBN 0). -309-02440-4; p. 203): saturated fatty acids (2-5% lauric acid, 5-20% myristic acid, 20-40% palmitic acid, and 5-20% stearic acid), unsaturated fatty acids (15-30% oleic acid, 1-8% palmitoleic acid, 1-6% linoleic acid and 0.5-3% linolenic acid). More preferably, the fatty acid composition of the milk fat used in the present invention is saturated fatty acid (2.5-4% lauric acid, 10-15% myristic acid, 28-35% palmitic acid, and 8-13% stearic acid), Unsaturated fatty acids (20-27% oleic acid, 2-6% palmitoleic acid, 2-5% linoleic acid and 0.8-2% linolenic acid).

In the present invention, the mixing ratio of the allicin-containing garlic material and the milk fat is 40 to 400 parts by weight, more preferably 70 to 380, based on the milk fat having a fat content of 80% by weight, based on 100 parts by weight of the allicin-containing garlic material. Parts by weight, even more preferably 60 to 150 parts by weight. If it is out of the above range it is not possible to obtain a fat and oil azoen-enhanced fat in the desired content, it is possible to obtain azoene-containing fats of 400 μg / g or more in the 60 to 400 parts by weight, 700 to 2000 in the 60 to 150 parts by weight range Azoene-containing garlic oils of µg / g or more can be obtained.

 In particular, in the present invention, in the step of mixing the allicin-containing garlic material with the milk fat, it is preferable to grind the size of the fat particles through one or more processes of sonication, homogenization and stirring. As the size of fat particles is reduced, the production of azoene increases due to the increase in the reaction surface area of garlic and milk fat.

In the present invention, the step of heating the mixture with milk fat containing the allicin-containing garlic material is preferably performed at 40 to 80 ° C, more preferably 50 to 70 ° C, even more preferably 60 to 70 ° C. Below the lower limit, the reaction time increases, and even if the reaction time is increased, the amount of azoene produced does not increase proportionally. When the upper limit is exceeded, the stability of the azoene is lowered and the Z / E ratio decreases. In addition, if the out of the range of 60 to 70 ℃ does not change the total production of azoene per fat or oil, the Z / E ratio is significantly reduced to less than 6, Z / E ratio of 6 or more, for example, 8 to 12, or No more can be achieved. This means that the ratio of Z-type azoene with high physiological activity is reduced.

In the present invention, the step of heating the mixture with milk fat containing the allicin-containing garlic material is preferably 1 to 6 hours, more preferably 1.5 to 4 hours, even more preferably 2 to 3 hours.

The azoene fortified fat prepared by the above method has a ratio of Z-azoene to E-azoene of 8 or more, an azoene content of 600 µg / g or more, and more preferably Z to E-azoene. -The ratio of azoene is 10-12, and the azoene content is 1000-2000 µg / g.

delete

delete

delete

delete

delete

delete

It provides the optimum conditions for producing azoene from the garlic and oil and fat mixture of the present invention, by the method of the present invention can be produced in a yield more than twice the conventional method, the Z / E ratio is high physiological Azoene-containing garlic oil, azoene-enriched dietary supplement, which is advantageous in terms of activity, can be prepared and has a suitable process protocol for mass production.

1 is a chromatogram of high performance liquid chromatography (HPLC) showing the results of the analytical method of the azoene compound established by the inventors. (A) Azoene isomer standard, (B) reaction product using milk fat and garlic juice, and (C) blank.
Figure 2 is a manufacturing process diagram of azoene fortified health functional food according to an embodiment of the present invention, the first step to prepare a garlic juice residue, garlic juice and garlic extract from garlic and the second step by mixing garlic and milk fat Maximize the production of azoene and the third step is to extract and purify the azoene.
Figure 3 is a reaction surface diagram showing the optimization of azoene production from garlic juice. (A) is the reaction surface diagram of reaction temperature (X1) and holding capacity (X3), (B) is the reaction surface diagram of reaction time (X2) and reaction temperature (X1), (C) is the holding surface (X3) and It is a reaction surface diagram of reaction time (X2).

Hereinafter, the present invention will be described in more detail with reference to Examples. It is to be understood by those skilled in the art that these embodiments are only for describing the present invention in more detail and that the scope of the present invention is not limited by these embodiments in accordance with the gist of the present invention .

Experimental Example  1: present in garlic-maintenance mixture Azoen ( ajoene Analysis method of compound

The sample used for the experiment was purchased from 2010 Nanji type garlic. The purchased garlic was crushed with a crusher (OSCAR, Kimhae Korea) and divided into garlic juice residue and juice, and then only the garlic juice was packaged using a vacuum film wrapping paper and used as a sample while storing at -80 ℃.

In 5 g of garlic juice, butter with a milk fat content of 80% or more is taken at a ratio of 1 to 5 times the weight of garlic juice, followed by vortexing for 1 minute, and then using an ultrasonic generator at 40 ° C. for 20 minutes. Sonication was performed. In the drying oven fixed at a constant temperature for the production of azoene, the oil and garlic juice were reacted for a certain time, centrifuged at 4000 rpm for 5 minutes, and then the supernatant was taken and used for each oil 2-4 times using ethyl acetate. After dilution, the azoene content was measured. The azoene content was determined using HPLC (JSACO, pump; 2089 plus, injector; 2057 plus, column oven; 2067 plus) equipped with an ultraviolet detector (JASCO, 2075 plus) and a silica gel column (Agilent, 4.6 × 250 mm, 5 μm). Used. The mobile phase composition for HPLC separation was 85:15 ratio of hexane and 2-propanol, the flow rate was 0.8 ml / min, the injection volume was 5 μl, and the UV wavelength was set to 240 nm for analysis (FIG. 1).

Manufacturing example  1: according to the type of edible oils and fats Azoen  Preparation of Containing Garlic Oil

10 kg of garlic was crushed with a crusher (OSCAR, Kimhae Korea) to obtain a pulverized product, which was compressed and filtered through a filter cloth to obtain 6 kg and 4 kg of garlic juice (primary) and juice residue, respectively.

To 5 g of the garlic juice, 15 g of milk fat (fat content of 80% by weight or more), edible oils and fats (7 kinds), and neutral medium-chain fatty acid (MCT oil) were added and mixed well, respectively, in a 40 ° C. ultrasonic bath. Sonication was performed for 20 minutes.

Reaction conditions for comparing the azoene content according to the edible oil and fat as a reaction temperature 65 ℃, the reaction time 2 hours and the oil content was three times the weight of the juice solution to prepare azoene-containing garlic oil, respectively.

Experimental Example  2: according to the type of edible oils and fats Azoen  Content comparison

The azoene content (total of Z-azoene and E-azoene) of the azoene-containing garlic oils prepared by different edible oils prepared in Preparation Example 1 was calculated and shown in Table 1 below.

division Azoene content (Μg / g, garlic juice) (Μg / g, maintenance) butterfat 1301 ^{a *} 434 ^{a *} Corn oil 633 ^b 212 ^b olive oil 656 ^b 219 ^b Grapeseed oil 604 ^b 202 ^b Soybean oil 672 ^b 225 ^b Perilla oil 553 ^b 185 ^b Sesame oil 608 ^b 203 ^b MCT Oil 692 ^b 232 ^b

*: Significance between milk fat ^a and edible oil ^{b according} to Duncan's multiple comparison test (P <0.05)

When the mixture was reacted by mixing 300 parts by weight of fat or oil with 100 parts of garlic juice, the azoene content per gram of garlic juice was 553 to 1301 µg, and the azoene content per gram of oil was 185 to 434 µg. In particular, when milk fat was used, it was confirmed that about 2 times higher azoene was produced than other vegetable oil or MCT oil.

Experimental Example  3: according to the type of edible oils and fats Azoen  Z / E ratio

The ratio of azoene-containing Z-azoene and E-azoene prepared by changing the edible oil prepared in Preparation Example 1, that is, Z / E ratio is calculated and shown in Table 2.

division Z / E ratio butterfat 10.1 Corn oil 8.2 olive oil 11.5 Grapeseed oil 6.2 Soybean oil 6.9 Perilla oil 9.5 Sesame oil 9.0 MCT Oil 9.2

Buttermilk had a lower Z / E ratio than olive oil, but a higher Z / E ratio than the rest of grape seed oil, soybean oil, perilla oil, sesame oil, corn oil and MCT oil.

Manufacturing example  2: using milk fat according to reaction temperature Azoen  Preparation of Containing Garlic Oil

Azoene-containing fat or oil was prepared in the same manner as in Preparation Example 1 using the garlic juice and milk fat of Preparation Example 1, but the reaction temperature was changed to 40, 60, 80, and 100 ° C., respectively, to azoene-containing garlic oil. Was prepared.

Experimental Example  3: according to the type of edible oils and fats Azoen  Z / E ratio

The ratio of azoene-containing Z-azoene and E-azoene prepared by varying the reaction temperature prepared in Preparation Example 2, that is, Z / E ratio is calculated and shown in Table 3.

division Z / E ratio 40 ℃ 4.7 50 ℃ 5.6 60 ° C 10.4 70 ℃ 8.5 80 ℃ 4.6 100 ℃ 1.2

It was confirmed that the Z / E ratio was markedly higher than 8 in the reaction temperature range of 60 to 70 ° C. compared with other temperatures.

Experimental Example  4: from garlic by response surface analysis Azoen  Generation condition optimization

In Experimental Example 2, the maximum production conditions of azoene were explored using milk fat (fat content of 80% by weight or more), which is the animal fat in which azoene is most produced. For this purpose, Response Surface Methodology was used, and the experimental design was based on the Central Composite of Design (CCD). The three independent variables included reaction temperature (X1), reaction time (X2) and oil content (X3) at five levels (-2, -1, 0, 1, 2) (Table 1). The dependent variable was set to the amount of azoene production (Y) in the garlic-fatty fat mixture, and the experiment was performed under 17 conditions.

Table 4 shows the conditions for producing azoene from garlic by the central synthetic scheme.

sign Independent variable level -2 -One 0 One 2 X ₁ Reaction temperature (℃) 20 40 60 80 100 X ₂ Reaction time (hr) One 2 4 6 8 X ₃ Oil volume
(times by weight) One 2 3 4 5

Statistical processing of data was performed by SAS package ver. 8.2 (SAS Institute Inc., Cary, NC, USA) was used. The relationship between the independent variable and the dependent variable was expressed by polynomial regression, and a three-dimensional response surface graph was shown using maple 7 (Waterloo maple Inc. Canada) based on the polynomial regression (FIG. 3).

The experimental results according to reaction temperature (20-100 ℃), reaction time (1-8 hr) and oil content (1-5 times), which are the main independent variables of azoene production in garlic-fat mixtures, are shown in Table 5. , Azoene content was 85.5-848.2 ㎍ / g (garlic juice) value, analysis of response surface regression analysis (Table 6), R² is 0.9189, close to 1, the significance is 0.0045 within 1% Significance was recognized at the significance level.

Table 5 shows the test values for azoene production conditions according to the central synthesis plan, and the polynomials for the generation of azoene compounds by reaction surface analysis are shown in Table 6.

Run No. Azoene production condition Azoene content
(Μg / g, garlic juice) Reaction temperature
(℃) Reaction time
(hr) Oil content
(times by weight) One 40 (-1) 2 (-1) 2 (-1) 469.8 2 40 (-1) 2 (-1) 4 (1) 728.7 3 40 (-1) 6 (1) 2 (-1) 437.4 4 40 (-1) 6 (1) 4 (1) 633.6 5 80 (1) 2 (-1) 2 (-1) 611.4 6 80 (1) 2 (-1) 4 (1) 814.5 7 80 (1) 6 (1) 2 (-1) 96.0 8 80 (1) 6 (1) 4 (1) 620.3 9 60 (0) 4 (0) 3 (0) 846.8 10 60 (0) 4 (0) 3 (0) 848.2 11 60 (0) 4 (0) 3 (0) 861.5 12 100 (2) 4 (0) 3 (0) 85.5 13 20 (-2) 4 (0) 3 (0) 494.7 14 60 (0) 8 (2) 3 (0) 592.1 15 60 (0) 1 (-2) 3 (0) 786.8 16 60 (0) 4 (0) 5 (2) 726.6 17 60 (0) 4 (0) 1 (-2) 312.2

Response Polynomial regression R² valence Azoen
content
(mg / g, garlic juice) Y = 809.902496-154.602047X ₁ -165.722972X ₂ + 267.585826X ₃ 0.9189 0.0045 -558.375375X ₁₂ -254.676991X ₁ X ₂ -123.575677X ₂₂ + 136.162237X ₁ X ₃ + 113.122560X ₂ X ₃ -329.021 106X ₃₂

As a result of analyzing the change of azoene content by the three-dimensional reaction surface under the experimental conditions designed by the central synthesis plan, the maximum point shape is shown in FIG.

In the above results, the optimum conditions for producing azoene using garlic-fatty fat mixture were 61.05 ° C, reaction time 2.56 hr, and oil content 3.63 (Table 7). In other words, by using the garlic-fat mixture to react at the optimum production conditions, azoene was produced at a concentration that is more than two times higher than the existing patent method.

Response Temperature time Oil content Maximum value shape ℃ hr (times by weight) Azoene content
(ug / g, garlic juice) 61.05 2.56 3.63 896.08 Maximum value

 In addition, the results of analysis of variance (significance analysis) of the azoene content regression model of garlic-fat mixtures are shown in Table 8.

Response F-value Temperature time Oil content (° C) (hour) (times by weight) Azoen 11.10 ^** 3.95 ^* 9.10 ^**

^* Significance at 10%, ^** significance at 1%

As shown in Table 8, the effect of reaction conditions on the amount of azoene produced was found to affect the reaction temperature and oil content more than the reaction time.

Experimental Example  5: butterfat and garlic Juice  According to the mixing ratio Azoen  Generation amount comparison

Milk cream (32.5% milk fat content) purchased commercially was able to prepare a milk fat product having a fat content of 94.5% by centrifugation. Azoene production was compared by varying the mixing ratio of the milk fat and garlic juice prepared in this way.

Garlic juice was added to 10 to 70% by weight of the total weight of the milk fat and garlic juice prepared above, and then mixed by vortex and then subjected to sonication (sonication) for 20 minutes at 40 ℃, This was reacted for 3 hours in a water bath fixed at 65 ℃ to produce azoene.

Table 9 shows the results of analyzing the content of azoene produced according to the mixing ratio of milk fat and garlic juice.

Mixing ratio of garlic juice and milk fat (weight ratio) Ajoene content (Μg / g, milk fat) 10: 90 53.2 ± 1.8 20: 80 223.1 ± 4.0 30: 70 466.5 ± 20.1 40: 60 784.8 ± 24.8 50: 50 1747.4 ± 64.6 60: 40 2001.7 ± 80.4 70: 30 870.4 ± 85.9

The azoene content was prepared by mixing 10% by weight of the garlic juice was 53.2 ㎍ / fat g, the azoene content was increased as the content of the garlic juice to 60% by weight. However, when the content of garlic juice was increased to 70% by weight, the azoene content was rather decreased.

In addition, in order to measure the fat content of the prepared azoene-containing garlic oil, 1-1.5 g of the test sample was precisely taken, taken in a beaker of 50 mL, washed in a separatory funnel with ether, and dehydrated by adding anhydrous sodium sulfate. Filtration was carried out in a 250 mL Erlenmeyer flask, ether was blown off, and dried at 105 ° C. until yielded to yield an amount of fat. The fat content of the azoene-containing garlic oil was 94.33% by weight.

Manufacturing example  3: Azoen  Soft-shell capsule manufacture with fortified oils and fats

Centrifugation of azoene-containing garlic oil (2000 ㎍ / g milk fat) prepared by mixing garlic juice and milk fat of Experimental Example 3 in a 5: 5 weight ratio to take a supernatant and gelatin to contain 500 mg of supernatant per capsule Soft-shell capsules were prepared.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the same is by way of illustration and example only and is not to be construed as limiting the scope of the present invention. Therefore, the substantial scope of the present invention will be defined by the appended claims and equivalents thereof.

Claims (17)

Preparing at least one allicin containing garlic material selected from garlic grind, garlic juice, garlic dry powder and garlic extract;
Mixing the allicin-containing garlic material with milk fat; And
A method of producing azoene-containing garlic oil using a milk fat comprising a; reacting by heating the mixture of allicin-containing garlic material and milk fat. The method of claim 1, wherein the garlic extract is any one garlic material selected from garlic crushed, garlic juice, garlic juice residue and garlic dry powder extracted with water, a lower alcohol having 1 to 4 carbon atoms or a mixed solvent thereof A method of producing azoene-containing garlic oil using a milk fat characterized in that. The garlic extract containing garlic oil according to claim 2, wherein the garlic extract is a garlic enzymatic extract obtained by reacting water with one or more enzymes selected from pectin and cellulose degrading enzyme with garlic material. Manufacturing method. The method of claim 1, wherein the allicin-containing garlic material is obtained by pulverizing and juice garlic to obtain a garlic juice extract and garlic juice residues, obtain a garlic extract from the garlic juice residues, and then mixing the garlic juice and garlic extract A method of producing azoene-containing garlic oil using a milk fat characterized in that. The method of claim 1, wherein the allicin content of the allicin-containing garlic material is 2 to 10 mg / g based on dry weight. The method of claim 1, wherein the fat content of the milk fat is 30 to 99% by weight. 7. The method of claim 6, wherein the milk fat is fresh cream or butter. 7. The method of claim 6, wherein the milk fat is derived from milk of cow, goat, sheep, horse, camel, donkey, deer, buffalo or yak. The method for producing azoene-containing garlic oil using milk fat according to claim 1, wherein 40 to 400 parts by weight of milk fat having a fat content of 80% by weight is mixed with 100 parts by weight of the allicin-containing garlic material. 10. The method for producing azoene-containing garlic oil using milk fat according to claim 9, wherein 60 to 150 parts by weight of the milk fat with a fat content of 80% by weight is mixed with 100 parts by weight of the allicin-containing garlic material. [Claim 2] The azoene-containing garlic oil of claim 1, wherein the mixing of the allicin-containing garlic material with the milk fat is performed by at least one method selected from ultrasonic treatment, homogenization and stirring. Manufacturing method. The method of claim 1, wherein the heating of the allicin-containing garlic material and the milk fat and the mixture is carried out at 30 to 80 ° C. The method of claim 12, wherein the heating of the allicin-containing garlic material and the milk fat and the mixture is carried out at 55 to 70 ° C. The method of claim 12, wherein the heating of the mixture with the milk fat and the allicin-containing garlic material is performed for 1 to 6 hours. Azoene-containing garlic oil prepared by the method of claim 1, wherein the ratio of Z-azoene to E-azoene is 6 or more and 12 or less, and the azoene content is 600 µg / g or more and 1200 µg / g or less. . delete delete

Images