JPWO2016113922A1 - Oil and fat composition for use in infant formula - Google Patents
Oil and fat composition for use in infant formula Download PDFInfo
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
- A23C9/00—Milk preparations; Milk powder or milk powder preparations
- A23C9/152—Milk preparations; Milk powder or milk powder preparations containing additives
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
- A23C9/00—Milk preparations; Milk powder or milk powder preparations
- A23C9/18—Milk in dried and compressed or semi-solid form
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
Abstract
３−ＭＣＰＤ及びグリシドール及びそれらの脂肪酸エステルの濃度が充分に低く、更に保存安定性に優れた、栄養学的に一定の基準を満たす育児用調製粉乳に用いられる油脂組成物を提供することを課題とする。リノール酸及びα−リノレン酸を含む育児用調製粉乳に用いるための油脂組成物であって、３５℃における固体油脂含有率が０．５％以下であり、３−モノクロロプロパン−１,２−ジオール（３−ＭＣＰＤ）濃度が０．３３ｐｐｍ以下でかつグリシドール濃度が０．０７ｐｐｍ以下である油脂組成物により上記課題が解決される。An object of the present invention is to provide an oil and fat composition for use in infant formulas satisfying a certain nutritionally constant standard, in which the concentrations of 3-MCPD and glycidol and their fatty acid esters are sufficiently low and excellent in storage stability. And Oil composition for use in infant formula containing linoleic acid and α-linolenic acid, solid oil content at 35 ° C. is 0.5% or less, 3-monochloropropane-1,2-diol The above problem is solved by an oil and fat composition having a (3-MCPD) concentration of 0.33 ppm or less and a glycidol concentration of 0.07 ppm or less.
Description
本発明は育児用調製粉乳に用いられる油脂組成物に関する。より詳しくは、育児用調製粉乳として適した栄養バランスを満たし、かつ育児用調製粉乳に用いられる油脂組成物として３−ＭＣＰＤ及びグリシドール及びそれらの脂肪酸エステルを充分に低下させた油脂組成物に関する。 The present invention relates to an oil and fat composition used for infant formula. More specifically, the present invention relates to an oil / fat composition that satisfies a nutritional balance suitable as a formula for infants and that has sufficiently reduced 3-MCPD, glycidol, and their fatty acid esters as an oil / fat composition used in formulas for infants.
食用油脂に含まれる３−ＭＣＰＤ（３−モノクロロプロパン−１,２−ジオール）脂肪酸エステルは、体内で代謝されて３−ＭＣＰＤが生成した場合は、その発がん性や毒性が疑われている。
一方、高濃度にＤＡＧ（ジアシルグリセロール）を含む油脂にはグリシドール脂肪酸エステルが含まれていることが報告されており、グリシドール脂肪酸エステルが体内で代謝されてグリシドールが生成した場合は、その発がん性や毒性が懸念されている。従って、食用油脂から３−ＭＣＰＤ、グリシドール及びそれらの脂肪酸エステルを低減することが望まれている。
特許文献１では、油脂をエステル交換してから酸性活性白土処理し、低い温度で脱臭することにより、３−ＭＣＰＤ及びグリシドール及びそれらの脂肪酸エステルを低減できることが記載されている。また特許文献１には、ＷＨＯ／ＦＡＯの発表では、３−ＭＣＰＤの一日許容摂取量（ＴＤＩ）は２μｇ／ｋｇ（体重）とされ、体重６０ｋｇの成人では、一日平均油脂摂取量を１２．５ｇとすると油脂中の３−ＭＣＰＤの許容濃度は９．６ｐｐｍとなることが記載されている。同様に、ドイツ連邦リスク評価研究所（ＢｆＲ）のデータでは、グリシドールの仮想的ベンチマーク用量下限値（ＢＭＤＬ１０）は４．０６ｍｇ／ｋｇ（体重）とされ、食品安全委員会が指標とする暴露マージンを１００００以上として計算すると、体重６０ｋｇの成人では、一日平均油脂摂取量を１２．５ｇとすると、油脂中のグリシドールの許容濃度は２．０ｐｐｍとなることが記載されている。When 3-MCPD (3-monochloropropane-1,2-diol) fatty acid ester contained in edible fat is metabolized in the body to produce 3-MCPD, its carcinogenicity and toxicity are suspected.
On the other hand, fats and oils containing DAG (diacylglycerol) at a high concentration have been reported to contain glycidol fatty acid esters. When glycidol fatty acid esters are metabolized in the body to produce glycidol, its carcinogenicity and There are concerns 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 oil and fat, then treating with acid activated clay, and deodorizing at a low temperature. Patent Document 1 discloses that the daily allowable intake (TDI) of 3-MCPD is 2 μg / kg (body weight) in the announcement of WHO / FAO, and the average daily fat intake is 12 for an adult with a body weight of 60 kg. It is described that the allowable concentration of 3-MCPD in fats and oils is 9.6 ppm when it is 0.5 g. Similarly, in the Federal Risk Assessment Institute (BfR) data, the hypothetical benchmark dose limit (BMDL10) for glycidol is 4.06 mg / kg (body weight), and the exposure margin as an index by the Food Safety Commission When calculated as 10,000 or more, it is described that in an adult with a body weight of 60 kg, the allowable concentration of glycidol in fat is 2.0 ppm when the daily average fat intake is 12.5 g.
一方、母乳代替食品である育児用あるいは乳児用調製粉乳は、栄養学的に一定の基準を満たすことが日本国内においても国際的にも要求されている。ヒトの乳汁脂肪には、乳児の発育に必要なリノール酸、α−リノレン酸、アラキドン酸、ドコサヘキサエン酸等の必須脂肪酸が一定量含まれていることから、消費者庁（日本）による指導要領（消食表第２７７号（平成２３年６月２３日））には、乳児用調製粉乳たる表示の許可基準では、１００ｋｃａｌ当たりの組成として、脂質が４．４〜６．０ｇ、リノール酸が０．３〜１．４ｇであり、α−リノレン酸が０．０５ｇ以上であることが示されている。
特許文献２には、人乳類似油脂組成物として、特定の脂肪酸組成を有する油脂組成物を作成したことが開示されている。
また、特許文献３では、ランダム化パーム油またはランダム化パームオレイン油と他の油脂を組み合わせた油脂組成物が開示されており、乳児栄養食用の油脂組成物として用いることができることが記載されている。On the other hand, infant formulas or infant formulas that are substitutes for breast milk are required to satisfy certain nutritional standards both in Japan and internationally. Human milk fat contains a certain amount of essential fatty acids such as linoleic acid, α-linolenic acid, arachidonic acid, and docosahexaenoic acid that are necessary for infant growth. According to the standard of permission for labeling infant formulas, 4.4 to 6.0 g of lipids and 0.08 g of linoleic acid are used as the composition per 100 kcal. 3 to 1.4 g, and α-linolenic acid is 0.05 g or more.
Patent Document 2 discloses that an oil and fat composition having a specific fatty acid composition was prepared as a human milk-like oil and fat composition.
Moreover, in patent document 3, the fat and oil composition which combined the randomized palm oil or the randomized palm olein oil and other fats and oils is disclosed, and it is described that it can be used as the fat and oil composition for infant nutrition food. .
特許文献１に記載されているとおり、体重６０ｋｇの成人では、一日平均油脂摂取量を１２．５ｇとすると油脂由来の３−ＭＣＰＤの許容濃度は９．６ｐｐｍであり、グリシドールの許容濃度は２．０ｐｐｍになる。一方、乳幼児においては一日平均油脂摂取量及び体重が異なる。例えば、体重６ｋｇの乳幼児の一日平均油脂摂取量を３６．０ｇとすると、油脂組成物中の３−ＭＣＰＤの許容濃度は０．３３ｐｐｍであり、グリシドールの許容濃度は０．０７ｐｐｍである。よって、これらの許容濃度以下に３−ＭＣＰＤ及びグリシドールを低減することが望まれる。
特許文献１に記載されるようなエステル交換、酸性活性白土処理及び低温脱臭処理を行えば、３−ＭＣＰＤ、グリシドール及びそれらの脂肪酸エステルを低減することはできるが、パーム油をエステル交換することによって油脂組成物の融点が上昇し、低温で結晶が発生してしまうため、高温での流通を要する。
育児用調製粉乳に用いられる油脂組成物は、上述のとおりリノール酸やα−リノレン酸に一定の基準が定められており、又、母乳代替食品として、特許文献２に記載されるような特定の脂肪酸組成を有する必要がある。リノール酸やα−リノレン酸等の高度不飽和脂肪酸は一般的に酸化安定性が悪く、高温での流通により経時的に風味が劣化してしまう。このため、これらの油脂組成物は流通工程(タンク保存、ローリー車運搬)を低温で行っているが、この低温流通時に結晶が発生してしまうと、油脂組成物転送時(ローリー車⇔タンク)にストレーナーが詰まってしまい、転送ができないとの問題がある。育児用調製粉乳に用いられる油脂組成物は、低温での流通時に結晶が発生しない、保存安定性を有する必要がある。
ここで言う保存安定性とは、低温での流通時に結晶が発生せず、良好な風味を有することを意味する。
従って、本発明の課題は、３−ＭＣＰＤ及びグリシドール及びそれらの脂肪酸エステルの濃度が充分に低く、更に保存安定性に優れた、栄養学的に一定の基準を満たす育児用調製粉乳に用いられる油脂組成物を提供することである。As described in Patent Document 1, in an adult with a weight of 60 kg, when the daily average fat intake is 12.5 g, the allowable concentration of 3-MCPD derived from fat is 9.6 ppm, and the allowable concentration of glycidol is 2 0.0 ppm. On the other hand, daily average fat and oil intake and body weight differ among infants. For example, if the daily average fat intake of an infant with a body weight of 6 kg is 36.0 g, the allowable concentration of 3-MCPD in the oil and fat composition is 0.33 ppm, and the allowable concentration of glycidol is 0.07 ppm. Therefore, it is desirable to reduce 3-MCPD and glycidol below these allowable concentrations.
By performing transesterification, acidic activated clay treatment and low-temperature deodorization treatment as described in Patent Document 1, 3-MCPD, glycidol and their fatty acid esters can be reduced, but by transesterifying palm oil Since melting | fusing point of an oil-fat composition raises and a crystal | crystallization will generate | occur | produce at low temperature, distribution | circulation at high temperature is required.
As described above, the oil and fat composition used in the infant formula has specific standards for linoleic acid and α-linolenic acid. Must have a fatty acid composition. Polyunsaturated fatty acids such as linoleic acid and α-linolenic acid generally have poor oxidation stability, and the flavor deteriorates over time due to circulation at high temperatures. For this reason, these oil and fat compositions perform the distribution process (tank storage, lorry vehicle transportation) at low temperatures, but if crystals are generated during this low temperature distribution, the oil and fat composition transfer (Lorry vehicle tank) There is a problem that the strainer is clogged and cannot be transferred. The oil and fat composition used for infant formula is required to have storage stability that does not generate crystals when distributed at low temperatures.
The storage stability referred to here means that crystals are not generated during circulation at low temperature and have a good flavor.
Accordingly, an object of the present invention is to provide fats and oils used in formulas for childcare that satisfy a certain nutritionally constant standard that has a sufficiently low concentration of 3-MCPD, glycidol, and their fatty acid esters, and that is excellent in storage stability. It is to provide a composition.
本発明の上記課題は、リノール酸及びα−リノレン酸を含み、３５℃における固体油脂含有率が０．５％以下であり、３−ＭＣＰＤ濃度が０．３３ｐｐｍ以下でかつグリシドール濃度が０．０７ｐｐｍ以下である油脂組成物により達成され、栄養、安全性及び保存安定性に優れた育児用調製粉乳に用いられる油脂組成物を提供する。 The above-mentioned problems of the present invention include linoleic acid and α-linolenic acid, the solid fat content at 35 ° C. is 0.5% or less, the 3-MCPD concentration is 0.33 ppm or less, and the glycidol concentration is 0.07 ppm. Provided is an oil / fat composition that is achieved by the following oil / fat composition and is used for infant formula milk powder that is excellent in nutrition, safety, and storage stability.
本発明の他の態様は以下のとおりであってもよい。
〔１〕育児用調製粉乳に用いるための、リノール酸及びα−リノレン酸を含む油脂組成物であって、３５℃における固体油脂含有率が０．５％以下であり、３−モノクロロプロパン−１,２−ジオール（３−ＭＣＰＤ）濃度が０．３３ｐｐｍ以下でかつグリシドール濃度が０．０７ｐｐｍ以下である上記油脂組成物。
〔２〕パーム油およびその分別油から選択される第１油脂、及びパーム核油およびその分別油から選択される第２油脂を含む混合油脂のエステル交換油脂を含む、前記〔１〕記載の油脂組成物。
〔３〕前記エステル交換油脂を製造するための混合油脂中の第１油脂の量が、油脂組成物全質量に対して５０質量％未満の量である、前記〔１〕または〔２〕に記載の油脂組成物。
〔４〕油脂組成物全質量に対し、リノール酸を５．０〜３２．０質量％の量で含み、かつα−リノレン酸を０．８質量％以上の量で含む、前記〔１〕〜〔３〕のいずれか一項に記載の油脂組成物。
〔５〕前記エステル交換油脂を製造するための混合油脂が、第１油脂及び第２油脂以外の一または複数の油脂を含む、前記〔１〕〜〔４〕のいずれか一項に記載の油脂組成物。
〔６〕前記エステル交換油脂以外の一または複数の他の油脂を含む、前記〔１〕〜〔５〕のいずれか一項に記載の油脂組成物。
〔７〕２００℃以上２３０℃以下で脱臭処理されている、前記〔１〕〜〔６〕のいずれか一項に記載の油脂組成物。
〔８〕前記〔１〕〜〔７〕のいずれか一項に記載の油脂組成物を含む、育児用調製粉乳。
〔９〕前記〔１〕〜〔７〕のいずれか一項に記載の油脂組成物の製造方法であって、下記工程を含む方法：
(i)パーム油およびその分別油から選択される第１油脂、パーム核油およびその分別油から選択される第２油脂、及び任意に含まれる第１油脂及び第２油脂以外の第３油脂を混合して混合油脂を作成し、前記混合油脂をエステル交換してエステル交換油脂を作成する工程、及び
(ii)前記エステル交換油脂、あるいは前記エステル交換油脂と他の任意の油脂を含む混合油脂を作成し、前記油脂を脱色処理する工程、及び
(iii)前記油脂を２００℃以上２３０℃以下で脱臭処理する工程。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, having a solid fat content at 35 ° C. of 0.5% or less, and 3-monochloropropane-1 , 2-diol (3-MCPD) concentration is 0.33 ppm or less and glycidol concentration is 0.07 ppm or less.
[2] The fat according to the above [1], comprising a transesterified fat of a mixed fat containing a first fat selected from palm oil and its fractionated oil and a second fat selected from palm kernel oil and its fractionated oil. Composition.
[3] The above [1] or [2], wherein the amount of the first fat in the mixed fat for producing the transesterified fat is less than 50% by mass relative to the total mass of the fat composition. Oil composition.
[4] The above-mentioned [1], which contains linoleic acid in an amount of 5.0 to 32.0% by mass and α-linolenic acid in an amount of 0.8% by mass or more based on the total mass of the oil and fat composition [3] The oil and fat composition according to any one of [3].
[5] The fats and oils according to any one of [1] to [4], wherein the mixed fats and oils for producing the transesterified fats and oils include one or more fats and oils other than the first and second fats and oils. Composition.
[6] The oil and fat composition according to any one of [1] to [5], including one or more other oils and fats other than the transesterified oil and fat.
[7] The oil and fat composition according to any one of [1] to [6], which is deodorized at 200 ° C. or higher and 230 ° C. or lower.
[8] An infant formula containing the oil and fat composition according to any one of [1] to [7].
[9] A method for producing an oil or fat composition according to any one of [1] to [7], comprising the following steps:
(i) a first fat selected from palm oil and its fractionated oil, a second fat selected from palm kernel oil and its fractionated oil, and a third fat other than the first fat and second fat optionally contained Mixing to make a mixed fat, transesterifying the mixed fat to make a transesterified fat, and
(ii) making the transesterified oil or fat, or mixed fats and oils containing the transesterified fat and other optional fats and oils, and decolorizing the fats and oils; and
(iii) The process of deodorizing the said fats and oils at 200 to 230 degreeC.
本発明の油脂組成物により、育児用調製粉乳として適した栄養バランス、特に一定量のリノール酸及びα−リノレン酸を有し、かつ安全性の観点から摂取を低減したい３−ＭＣＰＤ及びグリシドール及びそれらの脂肪酸エステル濃度が充分に低下した育児用調製粉乳を製造することができる。
更に、混合油脂によるエステル交換油脂の使用により、育児用調製粉乳のための油脂組成物として保存安定性に優れている。With the oil and fat composition of the present invention, 3-MCPD and glycidol, which have a nutritional balance suitable as a formula for childcare, in particular having a certain amount of linoleic acid and α-linolenic acid, and want to reduce intake from the viewpoint of safety, and those The infant formula can be produced with a sufficiently reduced fatty acid ester concentration.
Furthermore, the use of transesterified fats and oils with mixed fats and oils is excellent in storage stability as a fat and oil composition for infant formula milk powder.
＜育児用調製粉乳に用いられる油脂組成物＞
本発明の油脂組成物は育児用調製粉乳に用いられる。
育児用調製粉乳とは、母乳の代替品として用いられる粉乳であり、出来る限り母乳の成分に近似させることが多い。ヒトの乳汁の主な成分としては、蛋白質、脂肪、糖質などがあり、脂肪には、乳児の発育に必要なリノール酸、α−リノレン酸、アラキドン酸、ドコサヘキサエン酸等の必須脂肪酸が一定量含まれている。
消費者庁では、乳児用調製粉乳たる表示の許可基準では、１００ｋｃａｌ当たりの組成として、脂質が４．４〜６．０ｇ、リノール酸が０．３〜１．４ｇであり、α−リノレン酸が０．０５ｇ以上であることを示している。本発明における「育児用調製粉乳に用いられる油脂組成物」とは、このような栄養基準を満たすための油脂組成物を意味している。<Oil composition used for infant formula>
The oil and fat composition of the present invention is used in infant formula.
The infant formula is a 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 ingredients of human milk are protein, fat, sugar, etc. Fat contains a certain amount of essential fatty acids such as linoleic acid, α-linolenic acid, arachidonic acid, docosahexaenoic acid necessary for infant growth include.
In the Consumer Affairs Agency, the permissible standards for labeling infant formulas are 4.4 to 6.0 g of lipid, 0.3 to 1.4 g of linoleic acid, and α-linolenic acid as the composition per 100 kcal. It shows that it is 0.05 g or more. The “fat composition used in infant formula milk powder” in the present invention means an oil composition for satisfying such nutritional standards.
本発明の油脂組成物を用いた育児用調製粉乳は、リノール酸及びα−リノレン酸を含み、より好ましくは、１００ｋｃａｌ当たりの組成として、脂質４．４〜６．０ｇ、リノール酸を０．３〜１．４ｇの量で含み、かつα−リノレン酸を０．０５ｇ以上の量で含む。すなわち、油脂としてリノール酸を５．０〜３２．０質量％、α−リノレン酸を０．８質量％以上含むことが好ましい。
油脂中のリノール酸及びα−リノレン酸の量は様々な測定方法があるが、本明細書では、基準油脂分析法（２．４．２．２−２０１３ 脂肪酸組成 ＦＩＤ昇温ガスクロマトグラフ法）により測定した値を用いる。
油脂組成物中のリノール酸及びα−リノレン酸の比（リノール酸／α−リノレン酸）は、栄養学的な観点から、５〜１５の範囲であることが好ましい。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 lipid, 0.3% linoleic acid. It is contained in an amount of ˜1.4 g, and α-linolenic acid is contained in an amount of 0.05 g or more. That is, it is preferable to contain 5.0 to 32.0 mass% of linoleic acid and 0.8 mass% or more of α-linolenic acid as fats and oils.
There are various measurement methods for the amounts of linoleic acid and α-linolenic acid in fats and oils, but in this specification, by the standard fat analysis method (2.4.2.2-2013 fatty acid composition FID temperature rising gas chromatographic method). Use the measured value.
The ratio of linoleic acid and α-linolenic acid (linoleic acid / α-linolenic acid) in the oil / fat composition is preferably in the range of 5 to 15 from a nutritional viewpoint.
本発明の育児用調製粉乳に用いられる油脂組成物の３５℃における固体油脂含有率は０．５％以下であるため、３５℃で３週間結晶が発生しない。かかる特性により、３５℃における油脂組成物の保存安定性が優れている。より好ましくは、本発明の油脂組成物の３５℃における固体油脂含有率は０．０％である。 Since the solid fat content at 35 ° C. of the fat composition used in the infant formula of the present invention is 0.5% or less, no crystals are generated at 35 ° C. for 3 weeks. Due to such characteristics, the storage stability of the oil and fat composition at 35 ° C. is excellent. More preferably, the solid fat content at 35 ° C. of the fat composition of the present invention is 0.0%.
本発明の育児用調製粉乳に用いられる油脂組成物は、３−ＭＣＰＤ濃度が０．３３ｐｐｍ以下でかつグリシドール濃度が０．０７ｐｐｍ以下である。より好ましくは、３−ＭＣＰＤ濃度が０．２５ｐｐｍ以下、グリシドール濃度が０．０６ｐｐｍ以下である。 The oil and fat 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.
本発明の油脂組成物の原料油脂としては、製造した油脂組成物が上述した特性を満たすように選択して用いることができる。特に、リノール酸及びα−リノレン酸を上述の許可基準において含むように様々な油脂を組み合わせて用いることが好ましい。例えば、パーム油、パームオレイン、パームダブルオレイン、パームステアリン、パームミッドフラクション等のパーム油の分別油、パーム核油、パーム核オレイン、パーム核ステアリン等のパーム核油の分別油、ヤシ油、大豆油、菜種油、コーン油、ヒマワリ油、サフラワー油、エゴマ油、アマニ油、ハイオレイックヒマワリ油、ハイオレイック菜種油、綿実油、米糠油、ゴマ油、オリーブ油、落花生油、カカオ油等の植物油や、魚油、牛脂、豚脂等の動物油等が挙げられ、又、これら油脂の分別油も使用することができる。
好ましい組み合わせとしては、例えば、パーム油またはその分別油及びパーム核油またはその分別油を組み合わせて、更に他の油脂を組み合わせてもよい。As the raw oil and fat of the oil and fat composition of the present invention, it can be selected and used so that the manufactured oil and fat composition satisfies the above-described characteristics. In particular, it is preferable to use a combination of various fats and oils so that linoleic acid and α-linolenic acid are included in the above-mentioned permission criteria. For example, fractionated oil of palm oil such as palm oil, palm olein, palm double olein, palm stearin and palm mid fraction, fractionated oil of palm kernel oil such as palm kernel oil, palm kernel olein and palm kernel stearin, palm oil, large Vegetable oil such as bean oil, rapeseed oil, corn oil, sunflower oil, safflower oil, egoma oil, linseed oil, high oleic sunflower oil, high oleic rapeseed oil, cottonseed oil, rice bran oil, sesame oil, olive oil, peanut oil, cacao oil, fish oil, Examples include animal oils such as beef tallow and pork tallow, and fractionated oils of these 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 another oil or fat may be further combined.
本発明の油脂組成物は、好ましくは、パーム油およびその分別油から選択される第１油脂、及びパーム核油およびその分別油から選択される第２油脂を含む混合油脂のエステル交換油脂を含む。
パーム油の分別油とは、パームオレイン、パームダブルオレイン、パームステアリン、パームミッドフラクション等のパーム油の分別により得られる油脂を意味する。好ましくは、パームオレイン、パームダブルオレインが挙げられる。
パーム核油の分別油とは、パーム核オレイン、パーム核ステアリン等のパーム核油の分別により得られる油脂を意味する。好ましくは、パーム核オレインが挙げられる。
本発明において、パーム油およびその分別油から選択される油脂のみのエステル交換油脂を含む油脂組成物を用いた場合には３−ＭＣＰＤ濃度を充分に低下することはできるが、保存安定性が悪くなる。このため、パーム油およびその分別油から選択される油脂とパーム核油およびその分別油から選択される油脂の混合油脂のエステル交換油脂とすることにより、３−ＭＣＰＤ濃度を育児用調製粉乳として充分に安全なレベルに低下することができ、保存安定性も優れた油脂を得ることができる。The oil / fat composition of the present invention preferably comprises a transesterified oil / fat of a mixed oil / fat containing a first oil / fat selected from palm oil and its fractionated oil, and a second oil / fat selected from palm kernel oil and its fractionated oil. .
The 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. Preferably, palm olein and palm double olein are used.
The fractionated oil of palm kernel oil means fats and oils obtained by fractionation of palm kernel oil such as palm kernel olein and palm kernel stearin. Preferably, palm kernel olein is used.
In the present invention, when an oil / fat composition containing a transesterified fat / oil selected from palm oil and its fractionated oil is used, the 3-MCPD concentration can be sufficiently reduced, but the storage stability is poor. Become. For this reason, the 3-MCPD concentration is sufficient as a formula milk powder for childcare by using a transesterified fat of a fat selected from palm oil and its fractionated oil and a fat selected from palm kernel oil and its fractionated oil. Can be reduced to a safe level, and oils and fats having excellent storage stability can be obtained.
本発明の油脂組成物が上記エステル交換油脂を含む場合、前記エステル交換油脂を製造するための混合油脂中の第１油脂（パーム油およびその分別油から選択される油脂）の量は、油脂組成物全質量に対して５０質量％未満の量であることが好ましい。かかる範囲であることにより優れた保存安定性を有するからである。第１油脂の量は、油脂組成物全質量に対して４０質量％以下であることが更に好ましい。第１油脂は、油脂組成物全質量に対して２０質量％以上含まれることが好ましい。
第１油脂と第２油脂の比は、２０／８０〜８０／２０であることが好ましく、３０／７０〜７０／３０であることが更に好ましく、４０／６０〜６０／４０であることがより更に好ましい。When the oil / fat composition of the present invention contains the transesterified oil / fat, the amount of the first oil / fat (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 object. It is because it has the outstanding storage stability by being in this range. The amount of the first oil / fat is more preferably 40% by mass or less based on the total mass of the oil / fat composition. It is preferable that 20 mass% or more of 1st fats and oils are contained with respect to fats and oils composition total mass.
The ratio of the first fat / oil to the second fat / oil is preferably 20/80 to 80/20, more preferably 30/70 to 70/30, and more preferably 40/60 to 60/40. Further preferred.
前記エステル交換油脂を製造するための混合油脂は、第１油脂及び第２油脂以外の一または複数の第３油脂を含んでいてもよい。
第３油脂としては、リノール酸及びα−リノレン酸が許可基準の範囲に入れば制限はなく、例えば、大豆油、菜種油、コーン油、ヒマワリ油、サフラワー油、エゴマ油、アマニ油、ハイオレイックヒマワリ油、ハイオレイック菜種油等の液油が挙げられる。好ましくは、大豆油、菜種油である。The mixed fat / oil for producing the transesterified fat / oil may contain one or a plurality of third fat / oil other than the first fat / oil and the second fat / oil.
The third fat is not limited as long as linoleic acid and α-linolenic acid are within the permitted standards. For example, soybean oil, rapeseed oil, corn oil, sunflower oil, safflower oil, egoma oil, linseed oil, hyoleum Liquid oils such as ic sunflower oil and high oleic rapeseed oil are listed. Preferably, they are soybean oil and rapeseed oil.
本発明の油脂組成物は上記エステル交換油脂を含む場合には、エステル交換油脂以外に一または複数の他の油脂を含んでいてもよい。そのような油脂としては、リノール酸及びα−リノレン酸が目的の範囲に入れば制限はなく、例えば、大豆油、菜種油、コーン油、ヒマワリ油、サフラワー油、エゴマ油、アマニ油、ハイオレイックヒマワリ油、ハイオレイック菜種油等の液油が挙げられる。好ましくは、大豆油、菜種油である。
本発明の油脂組成物の全質量に対し、上記エステル交換油脂は、５０〜１００質量％含まれることが好ましく、６０〜１００質量％含まれることが更に好ましい。When the oil-and-fat composition of the present invention contains the above-described transesterified oil and fat, it may contain one or more other fats and oils in addition to the transesterified oil and fat. Such fats and oils are not limited as long as linoleic acid and α-linolenic acid fall within the intended range. For example, soybean oil, rapeseed oil, corn oil, sunflower oil, safflower oil, egoma oil, linseed oil, hyoleum Liquid oils such as ic sunflower oil and high oleic rapeseed oil are listed. Preferably, they are soybean oil and rapeseed oil.
The transesterified oil / fat 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 oil / fat composition of the present invention.
＜油脂組成物の製造方法＞
本発明の油脂組成物が上述したエステル交換油脂を含む態様において、油脂組成物の製造方法は、下記工程を含む方法である。
(i) パーム油およびその分別油から選択される第１油脂、パーム核油およびその分別油から選択される第２油脂、及び任意に含まれる第３の油脂を混合して混合油脂を作成し、前記混合油脂をエステル交換してエステル交換油脂を作成する工程、及び
(ii) 前記エステル交換油脂、あるいは前記エステル交換油脂と他の任意の油脂を含む混合油脂を作成し、前記油脂を脱色処理する工程、及び
(iii) 前記脱色処理油脂を２００℃以上２３０℃以下で脱臭処理する工程。
本発明の製造方法におけるエステル交換方法としては、当業者に公知のいずれの方法により行ってもよいが、金属触媒による化学的エステル交換反応法で行うことが好ましい。<The manufacturing method of fats and oils composition>
In the aspect in which the oil / fat composition of the present invention includes the above-described transesterified oil / fat, the method for producing the oil / fat composition includes the following steps.
(i) A mixed fat is prepared by mixing a first fat selected from palm oil and its fractionated oil, a second fat selected from palm kernel oil and its fractionated oil, and an optional third fat. A step of transesterifying the mixed fat and oil to produce a transesterified fat and oil, and
(ii) creating a mixed fat containing the transesterified fat or oil or the transesterified fat and other optional fats and oils, and decolorizing the fat;
(iii) A step of deodorizing the decolorized oil and fat at 200 ° C. or higher and 230 ° C. or lower.
The transesterification method in the production method of the present invention may be carried out by any method known to those skilled in the art, but is preferably carried out by a chemical transesterification reaction method using a metal catalyst.
本発明の製造方法のより好ましい態様としては、少なくとも以下の工程（１）〜工程（３）を経ることを特徴とする。各工程は、金属触媒によるエステル交換反応工程（１）、脱色処理工程（２）、脱臭工程（３）である。 A more preferred embodiment of the production method of the present invention is characterized by passing through at least the following steps (1) to (3). Each step is a transesterification step (1) using a metal catalyst, a decoloring step (2), and a deodorizing step (3).
＜金属触媒によるエステル交換反応工程（１）＞
まずは、常法に従って金属触媒存在下、好ましくはナトリウムメチラートの存在下で、エステル交換反応率が９０％以上となるよう化学的エステル交換反応を行う。エステル交換反応は、減圧下で５０〜１２０℃程度の温度での加熱下攪拌することにより行われる。また、通常、エステル交換反応の反応時間は１０分〜６０分であるが、本発明では、エステル交換反応率が９０％以上となるようエステル交換反応を１０分以上行う必要があり、好ましくは２０〜６０分間程度である。その後反応を停止させるために水を加えるが、更にクエン酸水溶液を添加してもよい。
触媒は、例えばエステル交換を行う原料油脂質量に対して０．１〜２質量％程度の範囲において使用してもよい。<Transesterification step with metal catalyst (1)>
First, a chemical transesterification reaction is carried out according to a conventional method in the presence of a metal catalyst, preferably in the presence of sodium methylate so that the transesterification rate is 90% or more. The transesterification reaction is performed by stirring under heating at a temperature of about 50 to 120 ° C. under reduced pressure. Further, the reaction time of the transesterification reaction is usually 10 minutes to 60 minutes, but in the present invention, the transesterification reaction needs to be performed for 10 minutes or more so that the transesterification rate is 90% or more, preferably 20 ~ About 60 minutes. Thereafter, water is added to stop the reaction, but an aqueous citric acid solution may be further added.
You may use a catalyst in the range of about 0.1-2 mass% with respect to the amount of raw material oil lipids which transesterify, for example.
＜脱色処理工程（２）＞
工程（１）で得られたエステル交換油脂を常法に従って脱色処理する。脱色処理に用いる吸着剤としては、好ましくは酸性活性白土を使用し、より好ましくは活性炭を併用する。効率よく、短時間で脱色処理を行うために、９０〜１２０℃程度の温度に加熱し且つ減圧下（一般に６．７ｋＰａ以下）で混合攪拌を行うことが好適であり、処理量などによって異なるが、一般に３０分間程度、混合攪拌を行えばよい。<Decolorization process (2)>
The transesterified oil obtained in the step (1) is decolorized according to a conventional method. As the adsorbent used for the decolorization treatment, preferably activated acid clay is used, more preferably activated carbon is used in combination. In order to perform the decoloring treatment efficiently and in a short time, it is preferable to heat to a temperature of about 90 to 120 ° C. and perform mixing and stirring under reduced pressure (generally 6.7 kPa or less), although it varies depending on the amount of treatment. Generally, mixing and stirring may be performed for about 30 minutes.
＜脱臭工程（３）＞
該脱臭工程は、温度条件（２００〜２３０℃）以外に特に制限はなく、食用油脂の脱臭に通常用いられている減圧水蒸気蒸留脱臭法でよい。<Deodorization process (3)>
There is no restriction | limiting in particular in this deodorizing process except temperature conditions (200-230 degreeC), The vacuum steam distillation deodorizing method normally used for the deodorizing of edible fats and oils may be sufficient.
本発明においては、通常の油脂精製時の温度よりは低温、即ち好ましくは２００℃以上２３０℃以下、より好ましくは２１０℃以上２２０℃以下で脱臭工程を通すことでグリシドール濃度が０．０７ｐｐｍ以下の油脂組成物を得ることができる。脱臭温度は、２００℃未満であれば更にグリシドールを低減できるが、油脂から十分に有臭成分を除去できず、商品性がなくなるので２００℃未満にするのは好ましくない。
一方、脱臭温度が２３０℃を超えると、グリシドールが増加するので好ましくない。特に、２６０℃以上にするとこれらの成分が著しく増加するので極めて好ましくない。
上記の製造方法により得られる油脂組成物は、脱臭工程の後においても３−ＭＣＰＤ及びグリシドール及びそれらの脂肪酸エステル濃度が低く、３−ＭＣＰＤ濃度を０．３３ｐｐｍ以下、グリシドール濃度を０．０７ｐｐｍ以下まで低減され、かつ風味も良好である。
なお、油脂組成物中には、３−ＭＣＰＤ及びグリシドールはそれぞれ３−ＭＣＰＤ脂肪酸エステル及びグリシドール脂肪酸エステルの形態で存在しているが、本明細書では、これらを３−ＭＣＰＤ及びグリシドールとして測定した値を用いて、油脂組成物中の「３−ＭＣＰＤ濃度」、「グリシドール濃度」と表現している。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 during normal oil 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 and fat composition can be obtained. If the deodorization temperature is less than 200 ° C., glycidol can be further reduced, but it is not preferable to make it less than 200 ° C. because the odorous component cannot be sufficiently removed from the fat and oil and the commercial property is lost.
On the other hand, when the deodorization temperature exceeds 230 ° C., glycidol increases, which is not preferable. In particular, when the temperature is 260 ° C. or higher, these components are remarkably increased, which is extremely undesirable.
The oil and fat composition obtained by the above production method has a low 3-MCPD and glycidol and fatty acid ester concentration even after the deodorization step, the 3-MCPD concentration is 0.33 ppm or less, and the glycidol concentration is 0.07 ppm or less. Reduced and good flavor.
In the oil and fat composition, 3-MCPD and glycidol are present in the form of 3-MCPD fatty acid ester and glycidol fatty acid ester, respectively, but in this specification, values obtained by measuring these as 3-MCPD and glycidol. Are used to express “3-MCPD concentration” and “glycidol concentration” in the oil and fat composition.
＜育児用調製粉乳＞
本発明の育児用調製粉乳は、上述した本発明の油脂組成物を含み、その他、育児用調製粉乳に含まれる任意の成分を含む。
任意の成分としては、例えば、たんぱく源、炭水化物源、ビタミン、ミネラル及びその他滋養要素等が挙げられる。
本発明の油脂組成物は、育児用調製粉乳中に、例えば１０〜３０質量％含有させることができるがこれに限定されるものではない。<Prepared infant formula>
The infant formula of the present invention includes the above-described oil and fat composition of the present invention, and additionally includes any components included in the infant formula.
Examples of optional components include a protein source, a carbohydrate source, vitamins, minerals, and other nourishing elements.
Although the oil-fat composition of this invention can be contained, for example in 10-30 mass% in the infant formula milk, it is not limited to this.
（製造例１）
パームオレイン２０ｋｇを、４ｋＰａ、９０℃の減圧下で３０分脱水後、パームオレイン１００質量部に対してナトリウムメチラート（商品名：ソジウムメチラート、日本曹達社製）を０．１２質量部添加し、４ｋＰａ、９０℃の減圧下で３０分間、化学的エステル交換反応を行った。パームオレイン１００質量部に５０質量部の水を加えて軽く混合し、化学的エステル交換反応を停止した。７０℃で３０分間静置し、セッケン分を除去した。その後４ｋＰａ、９０℃の減圧下で３０分脱水した。以上のようにして、製造例１のエステル交換油脂を作成した。(Production Example 1)
After dehydrating 20 kg of palm olein under reduced pressure of 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, chemical transesterification was performed 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 gently to stop the chemical transesterification reaction. The mixture was allowed to stand at 70 ° C. for 30 minutes to remove soap. Thereafter, dehydration was performed 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.
（製造例２）
表１の記載に従った組成の油脂を製造例１と同様の条件でエステル交換を行って、製造例２のエステル交換油脂を作成した。(Production Example 2)
The transesterification of fats and oils having the composition according to the description in Table 1 was carried out under the same conditions as in Production Example 1 to produce transesterified fats and oils of Production Example 2.
（製造例３）
表１の記載に従った組成の油脂を製造例１と同様の条件でエステル交換を行って、製造例３のエステル交換油脂を作成した。(Production Example 3)
Transesterification was performed on the fats and oils having the composition according to the description in Table 1 under the same conditions as in Production Example 1 to produce transesterified fats and oils of Production Example 3.
（製造例４）
表１の記載に従った組成の油脂を製造例１と同様の条件でエステル交換を行って、製造例４のエステル交換油脂を作成した。(Production Example 4)
The transesterification of the fats and oils having the composition according to the description in Table 1 was carried out under the same conditions as in Production Example 1 to produce the transesterified fats and oils of Production Example 4.
（実施例１）
製造例２のエステル交換油脂６７質量部、大豆油２１質量部及び菜種油１２質量部を混合し、油脂１００部に酸性活性白土（商品名：ガレオンアースＶ２、水澤化学工業製）を２．０質量部添加し、常圧下で、９０℃、６０分間脱色処理を行った。酸性活性白土は、ろ紙（商品名：東洋ろ紙Ｎｏ．２、アドバンテック製）及びろ過助剤（商品名：シリカ＃６００Ｈ、中央シリカ株式会社製）を用いて減圧ろ過により取り除き脱色油を得た。この脱色油１５ｋｇを２１０℃、７５分、真空度０．４ｋＰａ以下、吹込み水蒸気量３．０％（対油重量％）の条件で脱臭処理を行い、脱臭油を得た。Example 1
67 parts by mass of transesterified oil and fat of Production Example 2, 21 parts by mass of soybean oil and 12 parts by mass of rapeseed oil were mixed, and 2.0 parts by mass of acidic activated clay (trade name: Galeon Earth V2, manufactured by Mizusawa Chemical Co., Ltd.) in 100 parts of oil and fat. Part was added, and decolorization treatment was performed at 90 ° C. for 60 minutes under normal pressure. The acid activated clay was removed by filtration under reduced pressure using a filter paper (trade name: Toyo filter paper No. 2, manufactured by Advantech) and a filter aid (trade name: silica # 600H, manufactured by Chuo Silica Co., Ltd.) to obtain a decolorized oil. Deodorized oil was obtained by deodorizing 15 kg of this decolorized oil under the conditions of 210 ° C., 75 minutes, vacuum degree of 0.4 kPa or less, and blowing water vapor amount of 3.0% (weight% of oil).
（実施例２、３、４、５、６及び比較例１、２）
表２の記載に従った組成の油脂を実施例１と同様の条件で脱色、脱臭を行って、各油脂組成物を製造した。(Examples 2, 3, 4, 5, 6 and Comparative Examples 1 and 2)
The fats and oils having the composition according to the description in Table 2 were decolorized and deodorized under the same conditions as in Example 1 to produce each fat and oil composition.
製造例、実施例及び比較例で得られた各油脂について、３-ＭＣＰＤ及びグリシドール含有量を後述する分析方法で測定した。また、風味、融点、保存試験、固体油脂含有率、脂肪酸組成分析も行った。分析結果を表３に示す。 About each fats and oils obtained by the manufacture example, the Example, and the comparative example, 3-MCPD and glycidol content were measured with the analysis method mentioned 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.
（３−ＭＣＰＤ等の分析法）
「ＤＦＧ Ｓｔａｎｄａｒｄ Ｍｅｔｈｏｄｓ Ｓｅｃｔｉｏｎ Ｃ−Ｆａｔｓ Ｃ−ＩＶ １８（１０）」に従って測定した。
１．標準溶液
下記標準原液及び溶液は全て溶媒としてトルエンを用いた。
１）３−ＭＣＰＤ−１，２−パルミトイルエステル（和光純薬製、≧９８％）
３−ＭＣＰＤ−１，２−パルミトイルエステル標準原液（約１０００ｐｐｍ）
３−ＭＣＰＤ−１，２−パルミトイルエステル標準溶液（約４０ｐｐｍ）
２）ｄ５−３−ＭＣＰＤ−１，２−パルミトイルエステル（和光純薬製、≧９８％）
＊サロゲートとして使用
ｄ５−３−ＭＣＰＤ−１，２−パルミトイルエステル標準原液（約１０００ｐｐｍ）
ｄ５−３−ＭＣＰＤ−１，２−パルミトイルエステル標準溶液（約４０ｐｐｍ）
３）グリシジルステアレート（ＴＣＩ製、９６％≧）
グリシジルステアレート標準原液（約１０００ｐｐｍ）
グリシジルステアレート標準溶液（約４０ｐｐｍ）(3-MCPD analysis method)
It measured according to "DFG Standard Methods Section C-Fats C-IV 18 (10)."
1. Standard Solution Toluene was used as a solvent for all of the following standard stock solutions and solutions.
1) 3-MCPD-1,2-palmitoyl ester (Wako Pure Chemical Industries, ≧ 98%)
3-MCPD-1,2-palmitoyl ester standard stock solution (approximately 1000 ppm)
3-MCPD-1,2-palmitoyl ester standard solution (about 40 ppm)
2) d5-3-MCPD-1,2-palmitoyl ester (Wako Pure Chemical Industries, ≧ 98%)
* Used as surrogate d5-3-MCPD-1,2-palmitoyl ester standard stock solution (about 1000ppm)
d5-3-MCPD-1,2-palmitoyl ester standard solution (about 40 ppm)
3) Glycidyl stearate (manufactured by TCI, 96% ≧)
Glycidyl stearate standard stock solution (about 1000ppm)
Glycidyl stearate standard solution (about 40ppm)
２．試薬
１）超純水
２）トルエン（関東化学製、残農用、５０００倍濃縮）
３）ｔ-ブチルメチルエーテル(t-BME) （関東化学製、残農用、５０００倍濃縮）
４）メタノール（関東化学製、残農用、５０００倍濃縮）
５）ヘキサン（関東化学製、残農用、５０００倍濃縮）
６）酢酸エチル（関東化学製、残農用、５０００倍濃縮）
７）ジエチルエーテル（関東化学製、残農用、５０００倍濃縮）
８）イソオクタン
９）ナトリウムメトキシド
１０）ナトリウムメトキシド-メタノール溶液（２５ｇ／Ｌ）：０．２５ｇをメタノールで１０ｍＬに定溶〈＊用事調製（水分により分解しやすいので長期保存は不可）〉
１１）塩化ナトリウム（関東化学製、特級）
１２）塩化ナトリウム溶液（ＮａＣｌ ２００ｇ／Ｌ溶液）：塩化ナトリウム ５０ｇを超純水で溶解し２５０ｍＬとする
１３）臭化ナトリウム（関東化学製、特級）
１４）臭化ナトリウム水溶液（ＮａＢｒ ６００ｇ／Ｌ溶液）
１５）硫酸（２５％、６Ｎ）：硫酸（９６％、３６Ｎ）を６倍に希釈
ｅｘ）超純水５０ｍＬに硫酸（９６％、３６Ｎ）を１０ｍＬ加えた後６０ｍＬに定容
１６）酸性塩化ナトリウム水溶液（２００ｇ／Ｌ）：塩化ナトリウム水溶液１Ｌに硫酸（２５％）３５ｍＬを加える
ｅｘ）塩化ナトリウム水溶液２０ｍＬ＋硫酸（２５％）７００μＬ
１７）酸性臭化ナトリウム水溶液（塩化物を含まない食塩水）：臭化ナトリウム水溶液（６００ｇ／Ｌ）１Ｌに硫酸（２５％）３５ｍＬを加える
ｅｘ）臭化ナトリウム水溶液２０ｍＬ＋硫酸（２５％）７００μＬ
１８）フェニルボロン酸（ＰＢＡ，フェニルほう酸）
１９）誘導体化試薬：フェニルボロン酸をジエチルエーテルに溶解し、沈殿のある飽和状態〈＊用事調製〉2. Reagent 1) Ultrapure water 2) Toluene (manufactured by Kanto Chemical Co., Ltd.
3) t-Butyl methyl ether (t-BME) (Kanto Chemical Co., Ltd.
4) Methanol (manufactured by Kanto Chemical Co., Ltd.
5) Hexane (manufactured by Kanto Chemical Co., Ltd.
6) Ethyl acetate (manufactured by Kanto Chemical Co., Ltd.
7) Diethyl ether (manufactured by Kanto Chemical Co., Ltd.
8) Isooctane 9) Sodium methoxide 10) Sodium methoxide-methanol solution (25 g / L): Dissolve 0.25 g in 10 mL with methanol (* Essential preparation (can not be stored for a long time because it is easily decomposed by moisture))
11) Sodium chloride (manufactured by Kanto Chemical, special grade)
12) Sodium chloride solution (NaCl 200 g / L solution): 50 g of sodium chloride dissolved in ultrapure water to make 250 mL 13) Sodium bromide (manufactured by Kanto Chemical Co., Ltd., special grade)
14) Sodium bromide aqueous solution (NaBr 600 g / L solution)
15) Sulfuric acid (25%, 6N): 6-fold dilution of sulfuric acid (96%, 36N) ex) 10 mL of sulfuric acid (96%, 36N) was added to 50 mL of ultrapure water and then the volume was adjusted to 60 mL 16) Acidic sodium chloride Aqueous solution (200 g / L): Add 35 mL of sulfuric acid (25%) to 1 L of aqueous sodium chloride solution ex) 20 mL of aqueous sodium chloride solution + 700 μL of sulfuric acid (25%)
17) Acidic sodium bromide aqueous solution (saline containing no chloride): 35 mL of sulfuric acid (25%) is added to 1 L of aqueous sodium bromide solution (600 g / L). Ex) 20 mL of aqueous sodium bromide solution + 700 μL of sulfuric acid (25%)
18) Phenylboronic acid (PBA, phenylboric acid)
19) derivatizing reagents: phenylboronic acid was dissolved in diethyl ether, saturated <* errands Preparation> with precipitation
３．器具
１）パスツールピペット
２）メスシリンダー ２５ｍＬ、５０ｍＬ、１００ｍＬ
３）メスフラスコ ５ｍＬ、１０ｍＬ
４）ピペットマン Ｐ−５０００、Ｐ−１０００、Ｐ−２００
５）スクリューバイアル（ガラス製、１．５ｍＬ容）
６）シリンジ
７）フィルター（疎水性）3. Instrument 1) Pasteur pipette 2) Measuring cylinder 25mL, 50mL, 100mL
3) Volumetric flask 5mL, 10mL
4) Pipetteman P-5000, P-1000, P-200
5) Screw vial (made of glass, 1.5 mL capacity)
6) Syringe 7) Filter (hydrophobic)
４．分析方法
１）試料１００ ｍｇ（±０．５ｍｇ）を１．５ｍＬスクリューバイアルに採取した。
２）サロゲートとしてｄ５−３−ＭＣＰＤ−１，２−パルミトイルエステル標準溶液（約５０ｐｐｍ）を１００μＬ、ｔ-ブチルメチルエーテルを１００μＬ添加し攪拌した。
※コンタミ確認のため、３−ＭＣＰＤ等が検出しない試料（ｅｘ．エクストラバージンオリーブ油）を分析した。また、スパイク試料にはサロゲートとともに３−ＭＣＰＤ−１，２−パルミトイルエステル標準溶液（約４０ｐｐｍ）を１００μＬ添加し回収率を確認した。
３）ナトリウムメトキシド−メタノール溶液を２００μＬ加え、攪拌した後、常温で３．５〜５．５分反応させた。
４）反応を止めるため、分析［Ａ］には酸性塩化ナトリウム水溶液を６００μＬ、分析［Ｂ］には酸性臭化ナトリウム水溶液を６００μＬ加えた。
５）ヘキサン６００μＬを加え攪拌した後、５分以上静置し、ヘキサン層を除去する。再びへキサン６００μＬを加え、同操作を繰り返した。
６）ジエチルエーテル／酢酸エチル（６：４）混液を６００μＬ加え、攪拌した後、硫酸ナトリウム（無水）入りのバイアルに溶媒層を回収した。同操作を更に２回繰り返した。
７）ＰＢＡ溶液を１００μＬ添加し誘導体化した後、窒素ガスを吹き付け乾固させた。
８）イソオクタン１ｍＬで再溶解し、フィルターろ過した後、ＧＣ／ＭＳにて測定を行った。4). Analysis Method 1) 100 mg (± 0.5 mg) of a sample was taken 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.
* A sample (ex. Extra virgin olive oil) that was not detected by 3-MCPD or the like was analyzed for contamination confirmation. Further, 100 μL of 3-MCPD-1,2-palmitoyl ester standard solution (about 40 ppm) was added to the spiked sample together with the surrogate, and the recovery rate was confirmed.
3) 200 μL of sodium methoxide-methanol solution was added and stirred, and then reacted at room temperature for 3.5 to 5.5 minutes.
4) To stop the reaction, 600 μL of an acidic sodium chloride aqueous solution was added to Analysis [A], and 600 μL of an acidic sodium bromide aqueous solution was added to Analysis [B].
5) After adding 600 μL of hexane and stirring, the mixture is left to stand for 5 minutes or more to remove the hexane layer. Hexane 600 μL was added again, and the same operation was repeated.
6) 600 μL of diethyl ether / ethyl acetate (6: 4) mixed solution was added and stirred, and then the solvent layer was recovered in a vial containing sodium sulfate (anhydrous). The same operation was repeated twice more.
7) After derivatization by adding 100 μL of PBA solution, nitrogen gas was blown to dry.
8) Redissolved with 1 mL of isooctane, filtered, and measured by GC / MS.
５．装置・分析条件
装置：ＧＣ／ＭＳ（Ａｇｉｌｅｎｔ製５９７５Ｃ／７８９０Ａ）
カラム：ＤＢ−１７ＭＳ，内径０．２５ｍｍ×３０ｍ，膜厚 ０．２５μｍ
注入量：２μＬ
注入口温度：２４０℃
スプリットレス時間：１．５分
スプリット流量：２０ｍＬ／ｍｉｎ
キャリアガス：ヘリウム，１．２ｍＬ／ｍｉｎ，定流量
オーブン温度：８５℃（０．５ｍｉｎ）→６℃／ｍｉｎ→１５０℃→１２℃／ｍｉｎ→１８０℃→２５℃／ｍｉｎ→２８０℃（７ｍｉｎ）
イオン化：ＥＩ（ｐｏｓｉｔｉｖｅ）
測定イオン：３−ＭＣＰＤ ｍ／ｚ＝１４７（定量用）、１４６・１９６・１９８（確認用）
３−ＭＣＰＤ−ｄ５ ｍ／ｚ＝１５０（サロゲート）、１４９・２０１・２０３（確認用）
イオン源温度：２５０℃
四重極：１５０℃5. Apparatus / analysis condition apparatus: GC / MS (manufactured by Agilent, 5975C / 7890A)
Column: DB-17MS, inner diameter 0.25 mm × 30 m, film thickness 0.25 μm
Injection volume: 2 μL
Inlet 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 (positive)
Measurement ions: 3-MCPD m / z = 147 (for quantitative determination), 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．定量方法
[内部標準法]
サロゲートとして添加したｄ５−３−ＭＣＰＤ−１，２−パルミトイルエステルをｄ５−３−ＭＣＰＤ濃度に換算し、３−ＭＣＰＤの面積値をサロゲートの面積値で割った面積比にサロゲート濃度を乗じて３−ＭＣＰＤ濃度を算出した。
定量値＝サロゲート濃度×３−ＭＣＰＤ面積値／サロゲート面積値
上記で得られた定量値を試料採取量で除して、試料中濃度を求めた。
３−ＭＣＰＤ量［ｐｐｍ］＝定量値[μｇ／Ｌ]／試料採取量[ｍｇ]
※分析［Ａ］では３−ＭＣＰＤ―ＦＳ量、分析［Ｂ］ではグリシドールを除去した３−ＭＣＰＤ量が求められる。
分析［Ａ］・分析［Ｂ］それぞれの測定結果より、３−ＭＣＰＤ―ＦＳ量より３−ＭＣＰＤ量を減じ、グリシドール変換係数を乗じてグリシドール量を算出した。
グリシドール量［ppm］＝（３−ＭＣＰＤ―ＦＳ量［Ａ］ − ３−ＭＣＰＤ量［Ｂ］）×グリシドール変換係数ｔ 6). Quantitation method
[Internal standard method]
The d5-3-MCPD-1,2-palmitoyl ester added as a surrogate is converted to a d5-3-MCPD concentration, and the area ratio obtained by dividing the area value of 3-MCPD by the area value of the surrogate is multiplied by the surrogate concentration. -MCPD concentration was calculated.
Quantitative value = surrogate concentration × 3-MCPD area value / surrogate area value The quantified value obtained above was divided by the sampled amount to obtain the concentration in the sample.
3-MCPD amount [ppm] = quantitative value [μg / L] / sampled amount [mg]
* In analysis [A], the amount of 3-MCPD-FS is obtained, and in analysis [B], the amount of 3-MCPD from which glycidol has been removed is obtained.
From each measurement result of analysis [A] and analysis [B], the amount of 3-MCPD was subtracted from the amount of 3-MCPD-FS, and the glycidol conversion coefficient was multiplied to calculate the amount of glycidol.
Glycidol amount [ppm] = (3-MCPD-FS amount [A] −3-MCPD amount [B]) × glycidol conversion coefficient t
〈グリシドール変換係数の算出〉
グリシドールから３−ＭＣＰＤへの変換係数は塩化物存在下［Ａ］で検量線を作成して算出される。コンタミしていない油脂試料にグリシドール（グリシドールエステルとして）を複数濃度添加し、分析［Ａ］に従って処理した。結果として得られる検量線ｙ＝ｍｘ＋ｎの傾きの逆数はグリシドール変換係数ｔと等しい。
グリシドール変換係数ｔ＝１／ｍ<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]. Multiple concentrations of glycidol (as glycidol ester) were added to a non-contaminated oil sample and processed according to analysis [A]. The reciprocal of the slope of the resulting calibration curve y = mx + n is equal to the glycidol conversion coefficient t.
Glycidol conversion coefficient t = 1 / m
（保存試験（結晶・風味）方法）
１．５００ｍＬのガラスビーカーに油脂組成物４５０ｇを投入し、密閉（ラップ）をした。
２．５００ｍＬガラスビーカーに入れた油脂組成物を、各温度帯（３０℃、３５℃）に設定された恒温槽に保存した。
３．保存開始から３日、１週間、２週間、３週間での結晶の有無を目視にて確認した。
表２において、「○」は全く結晶が見えないことを意味する。「×」は結晶が目視で認められたことを意味する。
４．保存開始から３日、１週間、２週間、３週間での風味を確認した。
表２において、「○」は初期風味から変化がないことを意味する。「×」は初期風味から変化があることを意味する。(Preservation test (crystal / flavor) method)
1. 450 g of the oil / fat composition was put into a 500 mL glass beaker and sealed (wrapped).
2. The oil and fat composition placed in a 500 mL glass beaker was stored in a thermostat set in each temperature zone (30 ° C., 35 ° C.).
3. The presence or absence of crystals was visually confirmed 3 days, 1 week, 2 weeks and 3 weeks after the start of storage.
In Table 2, “◯” means that no crystals are visible. “X” means that the crystal was visually recognized.
4). The flavor at 3 days, 1 week, 2 weeks and 3 weeks from the start of storage was confirmed.
In Table 2, “◯” means that there is no change from the initial flavor. “X” means that there is a change from the initial flavor.
（脂肪酸組成の分析方法）
脂肪酸組成を基準油脂分析法（２．４．２．２−２０１３ 脂肪酸組成 ＦＩＤ昇温ガスクロマトグラフ法）により分析した。(Analytical method of fatty acid composition)
The fatty acid composition was analyzed by a standard oil analysis method (2.4.2.2-2013 fatty acid composition FID temperature rising gas chromatograph method).
（融点の分析方法）
融点を基準油脂分析法（３．２．２．２−２０１３ 融点（上昇融点））により分析した。(Measuring method of melting point)
The melting point was analyzed by a standard oil analysis method (3.2.2.2-2013 melting point (rising melting point)).
（固体油脂含有率の分析方法）
固体油脂含有率を基準油脂分析法（２．２．９−２０１３ 固体脂含量（ＮＭＲ法））により分析した。(Analytical method of solid fat content)
The solid fat content was analyzed by a standard fat analysis method (2.2.9-2013 solid fat content (NMR method)).
（結果）
実施例１〜６の油脂はいずれも３５℃における固体油脂含有率が０．５％以下でありかつ３−ＭＣＰＤ及びグリシドール濃度がそれぞれ０．３３ｐｐｍ以下及び０．０７ｐｐｍ以下であった。これらの油脂組成物は、３０℃で３日間、３５℃で３週間以上結晶が発生せず、保存安定性に優れたものであった。
これに対し、実施例１と同じ原料油脂組成であるがエステル交換を行っていない比較例２の油脂組成物は３５℃における固体含有率が０．５％以下であり、３０℃及び３５℃において３週間結晶が発生しておらず、保存安定性は優れていたが、３−ＭＣＰＤが許容濃度を大きく上回るものであった。また、実施例１と同じ原料油脂組成であるが、パームオレイン油のみエステル交換を行った比較例１の油脂組成物は、３−ＭＣＰＤ及びグリシドール濃度がそれぞれ０．３３ｐｐｍ以下及び０．０７ｐｐｍ以下であった。この油脂組成物の３５℃における固体油脂含有率は０．６％であり、３５℃において１週間で結晶が発生しており、保存安定性に優れていないものであった。(result)
The fats and oils of Examples 1 to 6 each had a solid fat 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 generated at 30 ° C. for 3 days and at 35 ° C. for 3 weeks or more.
On the other hand, the fat composition of Comparative Example 2 which has the same raw material fat composition as Example 1 but has not been transesterified has a solid content of not more than 0.5% at 35 ° C., and at 30 ° C. and 35 ° C. Crystals did not occur for 3 weeks and the storage stability was excellent, but 3-MCPD greatly exceeded the allowable concentration. Moreover, although it is the same raw material fat composition as Example 1, the fat composition of the comparative example 1 which transesterified only palm olein oil has 3-MCPD and a glycidol density | concentration of 0.33 ppm or less and 0.07 ppm or less, respectively. there were. The oil / fat composition had a solid oil / fat content of 35% at 35 ° C., crystals were generated in one week at 35 ° C., and the storage stability was not excellent.
Claims (9)
(i)パーム油およびその分別油から選択される第１油脂、パーム核油およびその分別油から選択される第２油脂、及び任意に含まれる第１油脂及び第２油脂以外の第３油脂を混合して混合油脂を作成し、前記混合油脂をエステル交換してエステル交換油脂を作成する工程、及び
(ii)前記エステル交換油脂、あるいは前記エステル交換油脂と他の任意の油脂を含む混合油脂を作成し、前記油脂を脱色処理する工程、及び
(iii)前記油脂を２００℃以上２３０℃以下で脱臭処理する工程。It is a manufacturing method of the oil-fat composition as described in any one of Claims 1-7, Comprising: The method including the following process:
(i) a first fat selected from palm oil and its fractionated oil, a second fat selected from palm kernel oil and its fractionated oil, and a third fat other than the first fat and second fat optionally contained Mixing to make a mixed fat, transesterifying the mixed fat to make a transesterified fat, and
(ii) making the transesterified oil or fat, or mixed fats and oils containing the transesterified fat and other optional fats and oils, and decolorizing the fats and oils; and
(iii) The process of deodorizing the said fats and oils at 200 to 230 degreeC.
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| MY192324A (en) * | 2016-09-02 | 2022-08-17 | Taiyo Yushi Corp | Fat and/or oil composition for use in infant formula |
| JP7283176B2 (en) * | 2019-03-28 | 2023-05-30 | 日油株式会社 | Oil and fat for infant formula, oil and fat composition for infant formula, and infant formula |
| JP7279467B2 (en) * | 2019-03-28 | 2023-05-23 | 日油株式会社 | Oil composition for powdered oil, powdered oil |
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|---|---|---|---|---|
| JPS61209544A (en) * | 1985-03-14 | 1986-09-17 | Ueda Seiyu Kk | Oil and fat resembling fat of human milk |
| JPH02163198A (en) * | 1988-12-15 | 1990-06-22 | Fuji Oil Co Ltd | Production of fats and oils |
| JP2011147436A (en) * | 2010-01-19 | 2011-08-04 | Cj Cheiljedang Corp | Method for producing edible oil-and-fat reduced in 3-mcpd-fs |
| JP2012136655A (en) * | 2010-12-27 | 2012-07-19 | Kaneka Corp | Manufacturing method of modified oil and fat composition |
| WO2013147138A1 (en) * | 2012-03-29 | 2013-10-03 | 株式会社カネカ | Oil and fat composition |
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| JP2911526B2 (en) * | 1990-02-23 | 1999-06-23 | 森永乳業株式会社 | Oil composition for infant food |
| ES2683348T5 (en) * | 2011-02-10 | 2023-02-09 | Cargill Inc | Process for the production of a refined oil |
| WO2016113922A1 (en) * | 2015-01-16 | 2016-07-21 | 太陽油脂株式会社 | Fat composition for use in infant formula |
-
2015
- 2015-05-18 WO PCT/JP2015/064157 patent/WO2016113922A1/en active Application Filing
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Patent Citations (5)
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|---|---|---|---|---|
| JPS61209544A (en) * | 1985-03-14 | 1986-09-17 | Ueda Seiyu Kk | Oil and fat resembling fat of human milk |
| JPH02163198A (en) * | 1988-12-15 | 1990-06-22 | Fuji Oil Co Ltd | Production of fats and oils |
| JP2011147436A (en) * | 2010-01-19 | 2011-08-04 | Cj Cheiljedang Corp | Method for producing edible oil-and-fat reduced in 3-mcpd-fs |
| JP2012136655A (en) * | 2010-12-27 | 2012-07-19 | Kaneka Corp | Manufacturing method of modified oil and fat composition |
| WO2013147138A1 (en) * | 2012-03-29 | 2013-10-03 | 株式会社カネカ | Oil and fat composition |
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| 農林水産省消費・安全局，食品中の３−ＭＣＰＤ脂肪酸エステル及びグリシドール脂肪酸エステルの含有実態調, vol. p.1-31, JPN6019020416, 17 December 2014 (2014-12-17), ISSN: 0004184110 * |
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| WO2016113922A1 (en) | 2016-07-21 |
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