JP6779789B2 - Oil and fat composition for use in formula milk powder for childcare - Google Patents

Description

The present invention relates to an oil / fat composition used for infant formula. More specifically, the present invention relates to an oil / fat composition which satisfies a nutritional balance suitable for infant formula and is sufficiently reduced in 3-MCPD and glycidol and their fatty acid esters as the oil / fat composition used in the infant formula.

When 3-MCPD (3-monochromelopropane-1,2-diol) fatty acid ester contained in edible fats and oils is metabolized in the body to produce 3-MCPD, its carcinogenicity and toxicity are suspected.
On the other hand, it has been reported that fats and oils containing DAG (diacylglycerol) in high concentration contain glycidol fatty acid ester, and when glycidol fatty acid ester is metabolized in the body to produce glycidol, its carcinogenicity and There is concern about toxicity. Therefore, it is desired to reduce 3-MCPD, glycidol and their fatty acid esters from edible fats and oils.
Patent Document 1 describes that 3-MCPD and glycidol and their fatty acid esters can be reduced by transesterifying fats and oils, treating them with acid activated clay, and deodorizing them at a low temperature. Further, in Patent Document 1, according to the announcement of WHO / FAO, the acceptable daily intake (TDI) of 3-MCPD is 2 μg / kg (body weight), and the average daily intake of fats and oils is 12 for an adult weighing 60 kg. It is stated that the acceptable concentration of 3-MCPD in fats and oils is 9.6 ppm when the amount is 5.5 g. Similarly, according to data from the Federal Institute for Risk Assessment (BfR), the lower limit of the hypothetical benchmark dose (BMDL10) for glycidol is 4.06 mg / kg (body weight), which is an exposure margin indexed by the Food Safety Commission. It is described that the permissible concentration of glycidol in fats and oils is 2.0 ppm when the average daily intake of fats and oils is 12.5 g for an adult weighing 60 kg or more when calculated as 10,000 or more.

On the other hand, milk powders for childcare or infants, which are alternative foods for breast milk, are required to meet certain nutritional standards both in Japan and internationally. Since human milk fat contains a certain amount of essential fatty acids such as linoleic acid, α-linolenic acid, arachidonic acid, and docosahexaenoic acid necessary for infant development, the guidelines by the Consumer Affairs Agency (Japan) (Japan) According to the food consumption table No. 277 (June 23, 2011), the composition per 100 kcal is 4.4 to 6.0 g of lipid and 0. of linoleic acid according to the permission standard for labeling of prepared powdered milk for infants. It is 3 to 1.4 g, and it is shown that α-linolenic acid is 0.05 g or more.
Patent Document 2 discloses that an oil / fat composition having a specific fatty acid composition was prepared as a human milk-like oil / fat composition.
Further, Patent Document 3 discloses an oil / fat composition in which randomized palm oil or randomized palm olein oil is combined with other oils and fats, and describes that it can be used as an oil / fat composition for infant nutritional food. ..

Japanese Unexamined Patent Publication No. 2012-136655 Japanese Unexamined Patent Publication No. 7-107904 Japanese Unexamined Patent Publication No. 2-231037

As described in Patent Document 1, in an adult weighing 60 kg, the permissible concentration of 3-MCPD derived from fats and oils is 9.6 ppm and the permissible concentration of glycidol is 2 when the average daily intake of fats and oils is 12.5 g. It becomes 0.0 ppm. On the other hand, the average daily fat intake and body weight of infants are different. For example, assuming that the average daily intake of fats and oils of an infant weighing 6 kg is 36.0 g, the permissible concentration of 3-MCPD in the fats and oils composition is 0.33 ppm, and the permissible concentration of glycidol is 0.07 ppm. Therefore, it is desired to reduce 3-MCPD and glycidol below these permissible concentrations.
3-MCPD, glycidol and their fatty acid esters can be reduced by performing ester exchange, acidic active white clay treatment and low temperature deodorization treatment as described in Patent Document 1, but by ester exchange of palm oil, Since the melting point of the fat and oil composition rises and crystals are generated at a low temperature, distribution at a high temperature is required.
As described above, the fat and oil composition used for infant formula has certain standards for linoleic acid and α-linolenic acid, and is a specific food substitute for breast milk as described in Patent Document 2. Must have a fatty acid composition. Polyunsaturated fatty acids such as linoleic acid and α-linolenic acid generally have poor oxidative stability, and their flavor deteriorates over time due to distribution at high temperatures. For this reason, these oil and fat compositions are subjected to the distribution process (tank storage, lorry vehicle transportation) at a low temperature, but if crystals are generated during this low temperature distribution, the oil and fat composition is transferred (lorry vehicle ⇔ tank). There is a problem that the strainer is clogged and transfer is not possible. The fat and oil composition used for the infant formula must have storage stability so that crystals do not form during distribution at low temperature.
The storage stability referred to here means that crystals do not occur during distribution at a low temperature and that the product has a good flavor.
Therefore, the subject of the present invention is the fats and oils used in formulas for childcare, which have a sufficiently low concentration of 3-MCPD, glycidol and their fatty acid esters, and have excellent storage stability and meet certain nutritional standards. To provide a composition.

The above object of the present invention contains linoleic acid and α-linolenic acid, has a solid fat content of 0.5% or less at 35 ° C., a 3-MCPD concentration of 0.33 ppm or less, and a glycidol concentration of 0.07 ppm. Provided is an oil / fat composition which is achieved by the following oil / fat composition and is used for a prepared milk powder for childcare, which is excellent in nutrition, safety and storage stability.

Other aspects of the present invention may be as follows.
[1] An oil / fat composition containing linoleic acid and α-linolenic acid for use in infant formula, which has a solid oil / fat content of 0.5% or less at 35 ° C. and 3-monochloropropane-1. , 2-diol (3-MCPD) concentration of 0.33 ppm or less and glycidol concentration of 0.07 ppm or less.
[2] The fat and oil according to the above [1], which comprises a first fat and oil selected from palm oil and its fractionated oil, and a transesterified fat and oil of a mixed fat and oil containing a second fat and oil selected from palm kernel oil and its fractionated oil. Composition.
[3] The above-mentioned [1] or [2], wherein the amount of the first fat and oil in the mixed fat and oil for producing the transesterified fat and oil is less than 50% by mass with respect to the total mass of the fat and oil composition. Ester composition.
[4] Linoleic acid is contained in an amount of 5.0 to 32.0% by mass and α-linolenic acid is contained in an amount of 0.8% by mass or more with respect to the total mass of the fat and oil composition. The oil / fat composition according to any one of [3].
[5] The fat or oil according to any one of [1] to [4] above, wherein the mixed fat and oil for producing the transesterified fat and oil contains one or more fats and oils other than the first fat and oil and the second fat and oil. Composition.
[6] The fat or oil composition according to any one of [1] to [5] above, which comprises one or more other fats and oils other than the transesterified fats and oils.
[7] The oil / fat composition according to any one of [1] to [6] above, which has been deodorized at 200 ° C. or higher and 230 ° C. or lower.
[8] A milk powder prepared for childcare, which comprises the oil / fat composition according to any one of the above [1] to [7].
[9] The method for producing an oil / fat composition according to any one of the above [1] to [7], which comprises the following steps:
(i) The first fat and oil selected from palm oil and its fractionated oil, the second fat and oil selected from palm kernel oil and its fractionated oil, and the third fat and oil other than the first fat and oil and the second fat and oil optionally contained. A step of mixing to prepare a mixed fat and oil, and transesterifying the mixed fat and oil to prepare a transesterified fat and oil, and
(ii) A step of preparing the transesterified fat or oil or a mixed fat or oil containing the transesterified fat or oil and any other fat or oil, and decolorizing the fat or oil.
(iii) A step of deodorizing the fat and oil at 200 ° C. or higher and 230 ° C. or lower.

With the fat and oil composition of the present invention, 3-MCPD and glycidol which have a nutritional balance suitable for infant formula, particularly a certain amount of linoleic acid and α-linolenic acid, and whose intake should be reduced from the viewpoint of safety, and theirs. It is possible to produce infant formula having a sufficiently reduced fatty acid ester concentration.
Furthermore, by using transesterified fats and oils with mixed fats and oils, it is excellent in storage stability as a fat and oil composition for infant formula.

<Fat composition used for formula milk powder for childcare>
The oil and fat composition of the present invention is used for infant formula.
Milk powder prepared for childcare is milk powder used as a substitute for breast milk, and is often approximated to the components of breast milk as much as possible. The main components of human milk are proteins, fats, sugars, etc. Fat contains a certain amount of essential fatty acids such as linoleic acid, α-linolenic acid, arachidonic acid, and docosahexaenoic acid, which are necessary for infant development. include.
According to the Consumer Affairs Agency, according to the permission criteria for labeling infant formula, the composition per 100 kcal is 4.4 to 6.0 g of lipid, 0.3 to 1.4 g of linoleic acid, and α-linolenic acid. It shows that it is 0.05 g or more. The "fat composition used for infant formula" in the present invention means a fat composition for satisfying such nutritional standards.

The infant formula using the oil and fat composition of the present invention contains linoleic acid and α-linolenic acid, and more preferably, the composition per 100 kcal is 4.4 to 6.0 g of lipid and 0.3 of linoleic acid. It is contained in an amount of ~ 1.4 g and contains α-linolenic acid in an amount of 0.05 g or more. That is, it is preferable that the fat and oil contains 5.0 to 32.0% by mass of linoleic acid and 0.8% by mass or more of α-linolenic acid.
There are various measuring methods for the amount of linoleic acid and α-linolenic acid in fats and oils, but in the present specification, the standard fats and oils analysis method (2.4.2.2-2013 fatty acid composition FID temperature rising gas chromatograph method) is used. Use the measured value.
The ratio of linoleic acid to α-linolenic acid (linoleic acid / α-linolenic acid) in the fat and oil composition is preferably in the range of 5 to 15 from the nutritional point of view.

Since the solid fat content at 35 ° C. of the fat and oil composition used in the infant formula of the present invention is 0.5% or less, crystals do not occur at 35 ° C. for 3 weeks. Due to these characteristics, the storage stability of the oil and fat composition at 35 ° C. is excellent. More preferably, the oil / fat composition of the present invention has a solid oil / fat content of 0.0% at 35 ° C.

The fat and oil composition used in the infant formula of the present invention has a 3-MCPD concentration of 0.33 ppm or less and a glycidol concentration of 0.07 ppm or less. More preferably, the 3-MCPD concentration is 0.25 ppm or less, and the glycidol concentration is 0.06 ppm or less.

As the raw material fat and oil of the fat and oil composition of the present invention, the produced fat and oil composition can be selected and used so as to satisfy the above-mentioned characteristics. In particular, it is preferable to use various fats and oils in combination so that linoleic acid and α-linolenic acid are contained in the above-mentioned permission criteria. For example, palm oil fractionated oil such as palm oil, palm olein, palm double olein, palm stear, palm mid fraction, palm kernel oil, palm kernel olein, palm kernel oil fractionated oil such as palm kernel stea, coconut oil, large Soybean oil, rapeseed oil, corn oil, sunflower oil, safflower oil, sesame oil, flaxseed oil, high oleic sunflower oil, high oleic rapeseed oil, cotton seed oil, rice bran oil, sesame oil, olive oil, peanut oil, cacao oil and other vegetable oils, fish oil, Examples include animal oils such as beef fat and coconut oil, and fractionated oils of these fats and oils can also be used.
As a preferable combination, for example, palm oil or a fractionated oil thereof and palm kernel oil or a fractionated oil thereof may be combined, and other fats and oils may be further combined.

The fat and oil composition of the present invention preferably contains an ester-exchanged fat and oil of a mixed fat and oil containing a first fat and oil selected from palm oil and its fractionated oil, and a second fat and oil selected from palm kernel oil and its fractionated oil. ..
Fractionated oil of palm oil means fats and oils obtained by fractionating palm oil such as palm olein, palm double olein, palm stearin, and palm mid fraction. Preferred examples include palm olein and palm double olein.
The fractionated oil of palm kernel oil means the fat and oil obtained by fractionating palm kernel oil such as palm kernel olein and palm kernel stear. Preferably, palm kernel olein is mentioned.
In the present invention, when a fat or oil composition containing a transesterified fat or oil containing only a fat or oil selected from palm oil and its fractionated oil is used, the 3-MCPD concentration can be sufficiently lowered, but the storage stability is poor. Become. Therefore, the transesterified fat and oil of the mixed fat and oil of the fat and oil selected from palm oil and its fractionated oil and the fat and oil selected from palm kernel oil and its fractionated oil is sufficient to make the 3-MCPD concentration a sufficient powdered milk for childcare. It is possible to obtain oils and fats that can be lowered to a safe level and have excellent storage stability.

When the oil / fat composition of the present invention contains the transesterified oil / fat, the amount of the first oil / fat (the oil / fat selected from palm oil and its fractionated oil) in the mixed oil / fat for producing the transesterified oil / fat is the oil / fat composition. The amount is preferably less than 50% by mass with respect to the total mass of the product. This is because it has excellent storage stability within such a range. The amount of the first fat and oil is more preferably 40% by mass or less with respect to the total mass of the fat and oil composition. The first fat and oil is preferably contained in an amount of 20% by mass or more based on the total mass of the fat and oil composition.
The ratio of the first fat and oil to the second fat and oil is preferably 20/80 to 80/20, more preferably 30/70 to 70/30, and more preferably 40/60 to 60/40. More preferred.

The mixed fat and oil for producing the transesterified fat and oil may contain one or more third fats and oils other than the first fat and oil and the second fat and oil.
As the third fat and oil, there is no limitation as long as linolenic acid and α-linolenic acid are within the range of the permission standard. For example, soybean oil, rapeseed oil, corn oil, sunflower oil, safflower oil, egoma oil, flaxseed oil, hyole. Liquid oils such as squid sunflower oil and high oleic rapeseed oil can be mentioned. Soybean oil and rapeseed oil are preferable.

When the oil / fat composition of the present invention contains the transesterified oil / fat, it may contain one or more other oils / fats in addition to the transesterified oil / fat. Such fats and oils are not limited as long as linolenic acid and α-linolenic acid fall within the desired range, for example, soybean oil, rapeseed oil, corn oil, sunflower oil, safflower oil, egoma oil, flaxseed oil, and hyole. Liquid oils such as squid sunflower oil and high oleic rapeseed oil can be mentioned. Soybean oil and rapeseed oil are preferable.
The transesterified fat and oil is preferably contained in an amount of 50 to 100% by mass, more preferably 60 to 100% by mass, based on the total mass of the fat and oil composition of the present invention.

<Manufacturing method of oil and fat composition>
In the embodiment in which the oil / fat composition of the present invention contains the transesterified oil / fat described above, the method for producing the oil / fat composition is a method including the following steps.
(i) A mixed fat and oil is prepared by mixing a first fat and oil selected from palm oil and its fractionated oil, a second fat and oil selected from palm kernel oil and its fractionated oil, and a third fat and oil optionally contained. , A step of transesterifying the mixed oil to prepare a transesterified oil, and
(ii) A step of preparing a transesterified fat or a mixed fat or oil containing the transesterified fat or oil and any other fat or oil, and decolorizing the fat or oil.
(iii) A step of deodorizing the decolorized fat and oil at 200 ° C. or higher and 230 ° C. or lower.
As the transesterification method in the production method of the present invention, any method known to those skilled in the art may be used, but it is preferable to carry out the transesterification reaction method using a metal catalyst.

A more preferable embodiment of the production method of the present invention is characterized in that at least the following steps (1) to (3) are performed. Each step is a transesterification reaction step (1) with a metal catalyst, a decolorization treatment step (2), and a deodorization step (3).

<Transesterification reaction step using a metal catalyst (1)>
First, a chemical transesterification reaction is carried out according to a conventional method in the presence of a metal catalyst, preferably sodium methylate, so that the transesterification reaction rate is 90% or more. The transesterification reaction is carried out by stirring under heating at a temperature of about 50 to 120 ° C. under reduced pressure. The reaction time of the transesterification reaction is usually 10 to 60 minutes, but in the present invention, it is necessary to carry out the transesterification reaction for 10 minutes or more so that the transesterification reaction rate is 90% or more, preferably 20 minutes. It takes about 60 minutes. After that, water is added to stop the reaction, but an aqueous citric acid solution may be further added.
The catalyst may be used, for example, in the range of about 0.1 to 2% by mass with respect to the amount of raw material oil and lipid for transesterification.

<Decolorization process (2)>
The transesterified fats and oils obtained in step (1) are decolorized according to a conventional method. As the adsorbent used for the decolorization treatment, preferably acidic activated clay is used, and more preferably activated carbon is used in combination. In order to perform the decolorization treatment efficiently and in a short time, it is preferable to heat the temperature to about 90 to 120 ° C. and perform mixing and stirring under reduced pressure (generally 6.7 kPa or less), which varies depending on the treatment amount and the like. Generally, mixing and stirring may be performed for about 30 minutes.

<Deodorizing process (3)>
The deodorizing step is not particularly limited except for the temperature condition (200 to 230 ° C.), and may be a reduced pressure steam distillation deodorizing method usually used for deodorizing edible oils and fats.

In the present invention, the glycidol concentration is 0.07 ppm or less by passing through the deodorizing step at a temperature lower than the temperature at the time of normal fat refining, that is, preferably 200 ° C. or higher and 230 ° C. or lower, more preferably 210 ° C. or higher and 220 ° C. or lower. An oil / fat composition can be obtained. If the deodorizing temperature is less than 200 ° C., glycidol can be further reduced, but it is not preferable to set the deodorizing temperature to less than 200 ° C. because odorous components cannot be sufficiently removed from fats and oils and the commercial value is lost.
On the other hand, if the deodorizing temperature exceeds 230 ° C., glycidol increases, which is not preferable. In particular, when the temperature is 260 ° C. or higher, these components increase remarkably, which is extremely unfavorable.
The oil and fat composition obtained by the above production method has a low concentration of 3-MCPD and glycidol and their fatty acid esters even after the deodorizing step, and has a 3-MCPD concentration of 0.33 ppm or less and a glycidol concentration of 0.07 ppm or less. It is reduced and has a good flavor.
In the fat and oil composition, 3-MCPD and glycidol are present in the form of 3-MCPD fatty acid ester and glycidol fatty acid ester, respectively, but in the present specification, these are measured values as 3-MCPD and glycidol. Is expressed as "3-MCPD concentration" and "glycidol concentration" in the fat and oil composition.

<Prepared milk powder for childcare>
The infant formula of the present invention contains the above-mentioned oil and fat composition of the present invention, and also contains any component contained in the formula for child care.
Optional ingredients include, for example, protein sources, carbohydrate sources, vitamins, minerals and other nourishing elements.
The oil and fat composition of the present invention can be contained, for example, 10 to 30% by mass in the infant formula, but is not limited thereto.

(Manufacturing Example 1)
After dehydrating 20 kg of palm olein under reduced pressure at 4 kPa and 90 ° C. for 30 minutes, 0.12 parts by mass of sodium methylate (trade name: Sodium methylate, manufactured by Nippon Soda Co., Ltd.) is added to 100 parts by mass of palm olein. Then, a chemical ester exchange reaction was carried out for 30 minutes under a reduced pressure of 4 kPa and 90 ° C. 50 parts by mass of water was added to 100 parts by mass of palm olein and mixed lightly to stop the chemical transesterification reaction. The soap was allowed to stand at 70 ° C. for 30 minutes to remove soap. Then, it was dehydrated for 30 minutes under a reduced pressure of 4 kPa and 90 ° C. As described above, the transesterified oil and fat of Production Example 1 was prepared.

(Manufacturing Example 2)
The oils and fats having the compositions according to Table 1 were transesterified under the same conditions as in Production Example 1 to prepare transesterified oils and fats in Production Example 2.

(Manufacturing Example 3)
The oils and fats having the compositions according to Table 1 were transesterified under the same conditions as in Production Example 1 to prepare transesterified oils and fats of Production Example 3.

(Manufacturing Example 4)
The oils and fats having the compositions according to Table 1 were transesterified under the same conditions as in Production Example 1 to prepare transesterified oils and fats of Production Example 4.

(Example 1)
67 parts by mass of transesterified fat and oil, 21 parts by mass of soybean oil and 12 parts by mass of rapeseed oil of Production Example 2 are mixed, and 2.0 parts by mass of acid activated clay (trade name: Galeon Earth V2, manufactured by Mizusawa Industrial Chemicals) is added to 100 parts of fat and oil. The mixture was partially added and decolorized at 90 ° C. for 60 minutes under normal pressure. The acid activated clay was removed by vacuum filtration using a filter paper (trade name: Toyo Filter Paper No. 2, manufactured by Advantech) and a filtration aid (trade name: Silica # 600H, manufactured by Chuo Silica Co., Ltd.) to obtain a decolorized oil. Deodorizing oil was obtained by deodorizing 15 kg of this decolorized oil under the conditions of 210 ° C., 75 minutes, a vacuum degree of 0.4 kPa or less, and a water vapor amount of 3.0% (weight% with respect to oil).

(Examples 2, 3, 4, 5, 6 and Comparative Examples 1, 2)
The fats and oils having the compositions according to Table 2 were decolorized and deodorized under the same conditions as in Example 1 to produce each fat and oil composition.

The 3-MCPD and glycidol contents of each of the fats and oils obtained in Production Examples, Examples and Comparative Examples were measured by the analysis method described later. In addition, flavor, melting point, storage test, solid fat content, and fatty acid composition analysis were also performed. The analysis results are shown in Table 3.

(Analytical method such as 3-MCPD)
It was measured according to "DFG Standard Methods Section C-Fats C-IV 18 (10)".
1. 1. Standard solution Toluene was used as the solvent for all of the following standard stock solutions and solutions.
1) 3-MCPD-1,2-palmitoyl ester (manufactured by Wako Pure Chemical Industries, ≧ 98%)
3-MCPD-1,2-palmitoyl ester standard stock solution (about 1000 ppm)
3-MCPD-1,2-palmitoyl ester standard solution (about 40 ppm)
2) d5-3-MCPD-1,2-palmitoyl ester (manufactured by Wako Pure Chemical Industries, ≧ 98%)
* Used as a surrogate d5-3-MCPD-1,2-palmitoyl ester standard stock solution (approx. 1000 ppm)
d5-3-MCPD-1,2-palmitoyl ester standard solution (about 40 ppm)
3) Glycidyl stearate (manufactured by TCI, 96% ≧)
Glycidyl stearate standard stock solution (approx. 1000 ppm)
Glycidyl stearate standard solution (about 40 ppm)

2. Reagent 1) Ultrapure water 2) Toluene (manufactured by Kanto Chemical Co., Inc., for residual farming, 5000 times concentrated)
3) t-Butyl methyl ether (t-BME) (manufactured by Kanto Chemical Co., Inc., for residual farming, 5000 times concentrated)
4) Methanol (manufactured by Kanto Chemical Co., Inc., for residual farming, 5000 times concentrated)
5) Hexane (manufactured by Kanto Chemical Co., Inc., for residual farming, 5000 times concentrated)
6) Ethyl acetate (manufactured by Kanto Chemical Co., Inc., for residual farming, 5000 times concentrated)
7) Diethyl ether (manufactured by Kanto Chemical Co., Inc., for residual farming, 5000 times concentrated)
8) Isooctane 9) Sodium methoxide 10) Sodium methoxide-methanol solution (25 g / L): 0.25 g dissolved in 10 mL with methanol <* Preparation for use (long-term storage is not possible because it is easily decomposed by water)>
11) Sodium chloride (manufactured by Kanto Chemical Co., Inc., special grade)
12) Sodium chloride solution (NaCl 200 g / L solution): Dissolve 50 g of sodium chloride in ultrapure water to make 250 mL 13) Sodium bromide (Kanto Chemical Co., Inc., special grade)
14) Sodium bromide aqueous solution (NaBr 600 g / L solution)
15) Sulfuric acid (25%, 6N): Sulfuric acid (96%, 36N) diluted 6-fold ex) Add 10 mL of sulfuric acid (96%, 36N) to 50 mL of ultrapure water, and then add 10 mL to 60 mL. 16) Acidic sodium chloride Aqueous solution (200 g / L): Add 35 mL of sulfuric acid (25%) to 1 L of sodium chloride aqueous solution ex) 20 mL of sodium chloride aqueous solution + 700 μL of sulfuric acid (25%)
17) Acidic sodium bromide aqueous solution (chloride-free saline solution): Add 35 mL of sulfuric acid (25%) to 1 L of sodium bromide aqueous solution (600 g / L) ex) 20 mL of sodium bromide aqueous solution + 700 μL of sulfuric acid (25%)
18) Phenylboronic acid (PBA, phenylboric acid)
19) Derivatization reagent: Phenylboronic acid is dissolved in diethyl ether and saturated with precipitation <* Preparation for errands >

3. 3. Instrument 1) Pasteur pipette 2) Graduated cylinder 25mL, 50mL, 100mL
3) Volumetric flask 5mL, 10mL
4) Pipetman P-5000, P-1000, P-200
5) Screw vial (made of glass, 1.5 mL volume)
6) Syringe 7) Filter (hydrophobic)

4. Analytical method 1) 100 mg (± 0.5 mg) of the sample was collected in a 1.5 mL screw vial.
2) As a surrogate, 100 μL of d5-3-MCPD-1,2-palmitoyl ester standard solution (about 50 ppm) and 100 μL of t-butyl methyl ether were added and stirred.
* To confirm contamination, a sample (ex. Extra virgin olive oil) not detected by 3-MCPD etc. was analyzed. In addition, 100 μL of 3-MCPD-1,2-palmitoyl ester standard solution (about 40 ppm) was added to the spike sample together with surrogate, and the recovery rate was confirmed.
3) 200 μL of a sodium methoxide-methanol solution was added, and the mixture was stirred and then reacted at room temperature for 3.5 to 5.5 minutes.
4) In order to stop the reaction, 600 μL of an acidic sodium chloride aqueous solution was added to the analysis [A], and 600 μL of an acidic sodium bromide aqueous solution was added to the analysis [B].
5) After adding 600 μL of hexane and stirring, let stand for 5 minutes or more to remove the hexane layer. 600 μL of hexane was added again, and the same operation was repeated.
6) 600 μL of a mixed solution of diethyl ether / ethyl acetate (6: 4) was added, and the mixture was stirred, and then the solvent layer was recovered in a vial containing sodium sulfate (anhydrous). The same operation was repeated twice more.
7) 100 μL of PBA solution was added for derivatization, and then nitrogen gas was sprayed to dry the solution.
8) After redissolving with 1 mL of isooctane and filtering with a filter, measurement was performed by GC / MS.

5. Equipment / Analytical conditions Equipment: GC / MS (Agilent 5975C / 7890A)
Column: DB-17MS, inner diameter 0.25 mm x 30 m, film thickness 0.25 μm
Injection volume: 2 μL
Injection temperature: 240 ° C
Splitless time: 1.5 minutes Split flow rate: 20 mL / min
Carrier gas: helium, 1.2 mL / min, constant flow oven temperature: 85 ° C (0.5 min) → 6 ° C / min → 150 ° C → 12 ° C / min → 180 ° C → 25 ° C / min → 280 ° C (7 min)
Ionization: EI (possive)
Measurement ion: 3-MCPD m / z = 147 (for quantification), 146, 196, 198 (for confirmation)
3-MCPD-d5 m / z = 150 (surrogate), 149, 201, 203 (for confirmation)
Ion source temperature: 250 ° C
Quadrupole: 150 ° C

6. Quantitative method
[Internal standard method]
The d5-3-MCPD-1,2-palmitoyl ester added as a surrogate was converted to the d5-3-MCPD concentration, and the area ratio of 3-MCPD divided by the surrogate area value was multiplied by the surrogate concentration 3 -MCPD concentration was calculated.

Quantitative value = surrogate concentration × 3-MCPD area value / surrogate area value The quantitative value obtained above was divided by the sampling amount to obtain the concentration in the sample.
3-MCPD amount [ppm] = quantitative value [μg / L] / sampling amount [mg]
* Analysis [A] determines the amount of 3-MCPD-FS, and analysis [B] determines the amount of 3-MCPD from which glycidol has been removed.

From the measurement results of Analysis [A] and Analysis [B], the amount of 3-MCPD was subtracted from the amount of 3-MCPD-FS and multiplied by the glycidol conversion coefficient to calculate the amount of glycidol.
Glycidol amount [ppm] = (3-MCPD-FS amount [A] -3-MCPD amount [B]) x glycidol conversion coefficient t

<Calculation of glycidol conversion coefficient>
The conversion coefficient from glycidol to 3-MCPD is calculated by creating a calibration curve in the presence of chloride [A]. Glycidol (as a glycidol ester) at a plurality of concentrations was added to the non-contaminated oil / fat sample and treated according to the analysis [A]. The inverse of the slope of the resulting calibration line y = mx + n is equal to the glycidol conversion coefficient t.
Glycidol conversion coefficient t = 1 / m

(Preservation test (crystal / flavor) method)
450 g of the oil / fat composition was put into a 1.500 mL glass beaker and sealed (wrapped).
The oil and fat composition placed in a 2.500 mL glass beaker was stored in a constant temperature bath set in each temperature range (30 ° C., 35 ° C.).
3. 3. The presence or absence of crystals was visually confirmed within 3 days, 1 week, 2 weeks, and 3 weeks from the start of storage.
In Table 2, "○" means that no crystals can be seen. "X" means that the crystal was visually recognized.
4. The flavor was confirmed within 3 days, 1 week, 2 weeks and 3 weeks from the start of storage.
In Table 2, "○" means that there is no change from the initial flavor. "X" means that there is a change from the initial flavor.

(Analysis method of fatty acid composition)
The fatty acid composition was analyzed by a reference fat analysis method (2.4.2.2-2013 fatty acid composition FID heated gas chromatograph method).

(Melting point analysis method)
The melting point was analyzed by the reference fat analysis method (3.2.2.2-2013 melting point (rising melting point)).

(Analysis method of solid fat content)
The solid fat content was analyzed by the standard fat analysis method (2.2.9-2013 solid fat content (NMR method)).

(result)
The fats and oils of Examples 1 to 6 had a solid fat and oil content of 0.5% or less at 35 ° C. and 3-MCPD and glycidol concentrations of 0.33 ppm or less and 0.07 ppm or less, respectively. These oil and fat compositions were excellent in storage stability, with no crystals forming at 30 ° C. for 3 days and at 35 ° C. for 3 weeks or longer.
On the other hand, the oil and fat composition of Comparative Example 2, which has the same raw material oil and fat composition as that of Example 1 but has not undergone transesterification, has a solid content of 0.5% or less at 35 ° C., and at 30 ° C. and 35 ° C. No crystals were generated for 3 weeks, and the storage stability was excellent, but 3-MCPD was much higher than the permissible concentration. Further, although the raw material oil / fat composition is the same as that of Example 1, the oil / fat composition of Comparative Example 1 in which only palm olein oil was transesterified had 3-MCPD and glycidol concentrations of 0.33 ppm or less and 0.07 ppm or less, respectively. there were. The solid fat / oil content of this fat / oil composition at 35 ° C. was 0.6%, and crystals were formed at 35 ° C. in 1 week, and the storage stability was not excellent.

Claims (8)

An oil / fat composition containing linoleic acid and α-linolenic acid for use in prepared milk powder for childcare, wherein the solid oil / fat content at 35 ° C. is 0.5% or less, and 3-monochromelopropane-1,2- The diol (3-MCPD) concentration is 0.33 ppm or less and the glycidol concentration is 0.07 ppm or less, and it is selected from the first fat and oil selected from palm oil and its fractionated oil, and palm kernel oil and its fractionated oil. Transesterified fats and oils composed of second fats and oils by transesterification, or mixed fats and oils composed of first fats and oils, second fats and oils, and third fats and oils, which are soybean oil, rapeseed oil, corn oil, and the like. The fat composition comprising a chemically transesterified fat and oil of a mixed fat and oil selected from the group consisting of sunflower oil, soybean oil, egoma oil, flaxseed oil, high oleic sunflower oil, and high oleic rapeseed oil. The fat or oil according to claim 1, wherein the amount of the first fat or oil in the mixed fat or oil for producing the chemically transesterified fat or oil is 20% by mass or more and less than 50% by mass with respect to the total mass of the fat or oil composition. Composition. The first or second claim, wherein linoleic acid is contained in an amount of 5.0 to 32.0% by mass and α-linolenic acid is contained in an amount of 0.8% by mass or more based on the total mass of the oil / fat composition. Oil and fat composition. The oil / fat composition according to any one of claims 1 to 3, wherein the chemically ester-exchanged oil / fat is contained in an amount of 50 to 100% by mass based on the total mass of the oil / fat composition. The oil / fat composition according to any one of claims 1 to 4, which comprises one or more other oils / fats other than the chemical transesterified oil / fat. The oil / fat composition according to any one of claims 1 to 5, which has been deodorized at 200 ° C. or higher and 230 ° C. or lower. A milk powder prepared for childcare, which comprises the oil / fat composition according to any one of claims 1 to 6. The method for producing an oil / fat composition according to any one of claims 1 to 6, which comprises the following steps:
(i) The first fat and oil selected from palm oil and its fractionated oil, the second fat and oil selected from palm kernel oil and its fractionated oil, and the third fat and oil other than the first fat and oil and the second fat and oil optionally contained. A step of mixing to prepare a mixed fat and oil, and chemically transesterifying the mixed fat and oil to prepare a chemically transesterified fat and oil, and
(ii) the created chemically interesterified fat, or a mixture oil containing the chemical interesterified fat and any other fat or oil, the step of bleaching processing the oil and,
(iii) A step of deodorizing the fat and oil at 200 ° C. or higher and 230 ° C. or lower.