JP2726217B2 - Method for removing cholesterol from fats and oils - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for removing cholesterol from edible fats and oils and a method for producing low-cholesterol fats and oils.

[0002]

2. Description of the Related Art Due to recent changes in eating habits, the opportunity to ingest fats and oils has increased, and there is a concern that adverse effects such as adult illness due to excessive intake of cholesterol may occur. In order to eliminate such concerns and to make fats and oils that can be taken safely by adults, fats and oils that have been treated to remove cholesterol are known.

[0003] JP-A-4-93399 discloses that an animal fat or oil is mixed with an aqueous solution containing 1 to 4% of cyclodextrin.
A method of removing cholesterol by stirring at about 40 ° C. for 120 to 240 minutes and removing an aqueous phase from a mixed solution is disclosed.

Japanese Patent Application Laid-Open No. 4-168198 discloses an aqueous solution prepared by supersaturating cyclodextrin with water and animal fats and oils, and removing the aqueous phase from the mixture to remove cholesterol. A method for doing so is disclosed.

According to these methods, cholesterol is included in cyclodextrin which is a starch having a cyclic structure in which the surface is hydrophilic and the internal structure is hydrophobic. Therefore, cholesterol is added to the aqueous phase together with cyclodextrin. Once removed, cholesterol in fats and oils can be easily removed.

[0006]

However, Japanese Patent Application Laid-Open No. 4-9 / 1990
In the method for removing cholesterol described in Japanese Patent No. 3399, there is a problem that the removal efficiency is extremely low and the cost is increased because it is necessary to stir the mixture involved in the inclusion reaction for a long time of 120 to 240 minutes.

In the method described in Japanese Patent Application Laid-Open No. 4-168198, a large amount of cyclodextrin is required in order to bring the aqueous solution of cyclodextrin into a supersaturated state.
The processing cost increases, and the efficiency of removing cholesterol is not so good with respect to the amount of cyclodextrin used.

Therefore, the present invention solves the above-mentioned problems, shortens the mixing and stirring time of fats and oils and cyclodextrin as much as possible, and furthermore, uses cyclodextrins efficiently, thereby reducing the amount of fats and oils in fats and oils. It is an object of the present invention to provide a method for efficiently removing cholesterol, or a method for efficiently producing low-cholesterol fats and oils.

[0009]

In order to solve the above-mentioned problems, in the present invention, 1 to 50 parts by weight of a linear saturated hydrocarbon having 5 to 10 carbon atoms is mixed with 100 parts by weight of fats and oils. The aqueous solution of cyclodextrin was added to the oil / fat-saturated hydrocarbon mixture, and the mixture was stirred at a temperature equal to or higher than the melting point of the oil / fat, and then the aqueous phase was removed.

Alternatively, an aqueous cyclodextrin solution is added to a fat / saturated hydrocarbon mixture obtained by mixing 1 to 50 parts by weight of a linear saturated hydrocarbon having 5 to 10 carbon atoms with respect to 100 parts by weight of fat or oil. After stirring at a temperature equal to or higher than the melting point of the fat or oil, a method for producing a low cholesterol fat or oil is obtained by fractionating the oil phase.

[0011]

In the method for removing cholesterol in fats and oils or the method for producing low cholesterol fats and oils according to the present invention, how a linear saturated hydrocarbon having 5 to 10 carbon atoms reacts with cholesterol or cyclodextrin, It is not clear whether cyclodextrin enhances the inclusion ability.

However, the inventors of the present application have found that even when only 1 to 50 parts by weight of a straight-chain saturated hydrocarbon having 5 to 10 carbon atoms is added, the inclusion ability of cyclodextrin can be enhanced. I found it. From this, the linear saturated hydrocarbon is not only the effect of lowering the viscosity by simply diluting the fat and oil, but also because the concentration of cyclodextrin is relatively increased merely by diluting the fat and oil,
It is fully conceivable that the catalyst functions as follows as a catalyst for promoting the inclusion effect of cyclodextrin.

That is, cyclodextrin dissolves in the aqueous phase, although the interior of the cyclic structure of the molecule is hydrophobic. In a state where such a cyclodextrin and a water-insoluble cholesterol-containing fat or oil are mixed, cholesterol is not immediately included, and it takes a considerable amount of time to be included, and a large amount of cyclodextrin that can be said to be excessive is produced. I need.

However, as in the present invention, when a linear saturated hydrocarbon having a predetermined number of carbon atoms is added to the mixed solution, the linear saturated hydrocarbon immediately acts on the hydrophobic group of cyclodextrin, It is thought that cholesterol easily comes into contact with cyclodextrin by using as a mediator, so that it can be efficiently and quickly included.

[0015]

The fats and oils used in the present invention can be used without particular limitation as long as they are fats and oils containing cholesterol. In particular, butter, milk fat, beef tallow, lard, fish oil and palm oil, which are edible fats and oils, respectively, can be used. They may be used alone or as a mixture of two or more thereof. Among them, those solid or semi-solid at room temperature are liquefied by heating or the like at the time of use.

The straight-chain saturated hydrocarbon having 5 to 10 carbon atoms used in the present invention is an alkane which is liquid at room temperature, and specifically, n-pentane, n-hexane, n-heptane, n-heptane, -Octane, n-nonane, n-decane. Of these, the use of n-hexane is preferred in view of the use of the present invention in the food field.

[0017] Such a saturated hydrocarbon is used in an amount of 1 to 50 parts by weight, preferably 5 to 50 parts by weight, based on 100 parts by weight of the above-mentioned fats and oils.
20 parts by weight are blended. Because, when the amount is less than 1 part by weight, the inclusion ability of cyclodextrin is not enhanced.
Even if it is added in a large amount exceeding 50 parts by weight, no further effect can be expected anymore, and it is not practical in terms of production cost.

The cyclodextrin used in the present invention is
It is a type of starch and is an oligosaccharide in which 6 to 8 D-glucoses are α-1,4 linked cyclically, and are called α, β, and γ types in the order of increasing D-glucose numbers. Among them, β-cyclodextrin is preferred because it has the highest cholesterol inclusion ability.

Cyclodextrin is used by dissolving it in water. The concentration of the aqueous solution is 0.5 to 5% by weight, preferably 2 to 3% by weight. The reason is that if the amount is less than 0.5% by weight, the ability to include cholesterol is too weak, so that the desired effect cannot be obtained. If the amount is more than 5% by weight, the solubility will be exceeded and the practicality will be lost. You will lose.

The mixing ratio of the fat or oil mixed with a linear saturated hydrocarbon having 5 to 10 carbon atoms to the aqueous β-cyclodextrin solution is as follows: the fat or oil mixed with the saturated hydrocarbon / β.
The weight ratio of the aqueous solution of cyclodextrin is from 0.2 to 5.0;
And more preferably 0.5 to 2.0
It is. If the weight ratio is less than 0.2, there is no problem with inclusion, but no further improvement in the removal efficiency can be expected, which is not practical. If the weight ratio exceeds 5.0, the reaction involving inclusion does not occur efficiently, and it is difficult to efficiently remove cholesterol in fats and oils.

Here, β relative to the fat / saturated hydrocarbon system
-The mixing ratio (weight ratio) of cyclodextrin itself is preferably from 0.001 to 0.25, more preferably from 0.01 to 0.06, from the relationship between the concentration of the aqueous solution and the weight ratio. is there.

The reaction time of β-cyclodextrin with fats and oils mixed with linear saturated hydrocarbons is 20 to 60.
Minutes and most of the reaction is completed within 30 minutes. This is an extremely short time as compared with the reaction using only β-cyclodextrin.

In the present invention, to remove the aqueous phase,
Further, the aqueous phase and the oil phase may be separated into layers by a method such as adding water and stirring or centrifuging.

[Examples 1 to 6] 100 g of butter oil obtained by heating a commercial butter to separate it into an oil phase and an aqueous phase and then centrifuging to collect the oil (cholesterol content 2. 1 mg / g), and normal hexane was added and mixed at a mixing ratio shown in Table 1 (g, parts by weight based on 100 parts by weight of butter oil) to prepare an oil phase.

On the other hand, 3 g of β-cyclodextrin (manufactured by Saltwater Port Refining Co., Ltd.) was dissolved in 100 ml of warm water at 50 ° C.
An aqueous phase of cyclodextrin was prepared.

To 100 ml of the above aqueous phase, 100 g of the oil phase was charged, and the mixture was kept at 50 ° C. with a stirrer.
After mixing and stirring for 60 minutes, the mixed solution was washed with warm water to separate an oil phase portion and an aqueous phase portion, and normal hexane in the separated oil phase portion was removed by an evaporator to obtain a low cholesterol butter oil.

The cholesterol content of the obtained butter oil was measured by a gas chromatography method (Japanese Society of Food Industry, “Food Analysis”, page 571), and the cholesterol content (mg / g) and the removal rate (%) were measured. Are also shown in Table 1.

[0028]

[Table 1]

As is clear from the results in Table 1, Examples 1 to 6 in which 1 to 50 parts by weight of a normal hexane mixed solution was covered with cyclodextrin with respect to 100 parts by weight of butter oil were used for 30 minutes. 50.0 ~
It showed a cholesterol removal rate of 76.7% and a high removal rate of 57.1 to 87.6% under stirring conditions for 60 minutes.

[Examples 7 to 9] The same procedure as in Examples 1 to 6 was repeated except that the hydrocarbons shown in Table 2 were added to 100 g of butter oil obtained in the same manner as in Examples 1 to 6 in the amounts shown in Table 2. A low cholesterol butter oil was produced in exactly the same manner as in Nos. 1 to 6, and the cholesterol content and its removal rate are also shown in Table 2.

[0031]

[Table 2]

As shown in Table 2, the number of carbon atoms is 5, 8 or 1
Examples 7 to 9 to which 0 alkanes were added exhibited a cholesterol removal rate of 54.8 to 61.4% under stirring conditions for 30 minutes, and 72.4 to 78.1% under stirring conditions of 60 minutes.
High removal rate.

Comparative Examples 1 and 2 Examples 1 to 6
A cholesterol-removing butter oil was produced in exactly the same manner as in Example, except that normal hexane was added to 100 g of the butter oil obtained in the same manner as in Example 3 except that normal hexane was added at a ratio shown in Table 3 (or no addition). .

The cholesterol content and the removal rate of the obtained butter oil were measured in exactly the same manner as in the examples.
The results are shown in Table 3.

[0035]

[Table 3]

As a result, in Comparative Example 1 in which normal hexane was not used, the removal ratio was a low value of 48.1% even when the stirring time was 60 minutes.

In Comparative Example 2 in which normal hexane was added in an amount exceeding a predetermined amount, the cholesterol removal rate was substantially the same as that in Example 6 described above, and was a good result.

However, the mixed solution in this case is in a state of being diluted twice by an excess of normal hexane. Considering the dilution ratio, it can be seen that an excessive addition of normal hexane does not necessarily contribute to efficient cholesterol removal.

Comparative Example 3 In Examples 1 to 6, 100 g of butter oil to which normal hexane was not added was used, and the aqueous phase portion of 3% β-cyclodextrin was added to 40 g of the same.
A butter oil was produced in exactly the same manner except that 0 ml was mixed, and the cholesterol content and the removal rate were also shown in Table 3.

In this case, relatively fats and oils (butter oil)
The cholesterol removal rate was not improved even in the mixing condition where the ratio of cholesterol was low. This indicates that the improvement in the cholesterol removal rate in the examples was not caused by a relative decrease in the fat content due to the addition of normal hexane.

Comparative Examples 4 to 6 Example 1 was repeated except that the compounds shown in Table 3 were added to 100 g of butter oil obtained in exactly the same manner as in Examples 1 to 6 in the amounts shown in Table 3.
The low cholesterol butter oil was produced in exactly the same manner as in No. 6 to 6, and the cholesterol content and the removal rate thereof were also shown in Table 3.

From the results shown in the table, it was found that Comparative Example 4 in which acetone was added, Comparative Example 5 in which alcohol was added, and Comparative Example 6 in which hydrocarbon having a cyclic structure was added, even when the stirring time was 60 minutes. Removal rate is 3.8-3
The value was as low as 7.0%.

[0043]

According to the present invention, as described above, a liquid saturated oil and fat are mixed with a linear saturated hydrocarbon having 5 to 10 carbon atoms, and an aqueous solution of cyclodextrin is added to the mixed oil and fat. Cholesterol is very efficiently included in cyclodextrin, and the mixing and stirring time of fats and oils and cyclodextrin is shortened as much as possible, so that the cyclodextrins in the fats and oils can be efficiently and at high efficiency. There is an advantage that dextrin can be removed.

Continuation of the front page (72) Inventor Komune Takatsu 4-1-1, Nishinakajima, Yodogawa-ku, Osaka, Osaka Inside Nissin Foods Co., Ltd. (72) Inventor Manabu Sato 4-1-1, Nishinakajima, Yodogawa-ku, Osaka, Osaka No. 1 Inside Nissin Foods Co., Ltd. (72) Inventor Hideyuki Tsujino Inside Nissin Foods Co., Ltd. 4-1-1 Nishinakajima, Yodogawa-ku, Osaka-shi, Osaka

Claims (2)

(57) [Claims] 1. A carbon number of 5 to 1 with respect to 100 parts by weight of fats and oils
After adding a cyclodextrin aqueous solution to a fat / saturated hydrocarbon mixture obtained by mixing 1 to 50 parts by weight of a linear saturated hydrocarbon at 0 and stirring the mixture at a temperature equal to or higher than the melting point of the fat, the aqueous phase is removed. A method for removing cholesterol in fats and oils. 2. A composition having 5 to 1 carbon atoms per 100 parts by weight of fats and oils.
After adding a cyclodextrin aqueous solution to a fat / saturated hydrocarbon mixture obtained by mixing 1 to 50 parts by weight of a linear saturated hydrocarbon at 0 and stirring the mixture at a temperature equal to or higher than the melting point of the fat, the oil phase is separated. A method for producing a low-cholesterol fat or oil comprising removing fat.