WO2018043701A1 - Fat composition for use in infant formula - Google Patents

Fat composition for use in infant formula Download PDF

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Publication number
WO2018043701A1
WO2018043701A1 PCT/JP2017/031564 JP2017031564W WO2018043701A1 WO 2018043701 A1 WO2018043701 A1 WO 2018043701A1 JP 2017031564 W JP2017031564 W JP 2017031564W WO 2018043701 A1 WO2018043701 A1 WO 2018043701A1
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Prior art keywords
oil
fat
fats
composition
oils
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PCT/JP2017/031564
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French (fr)
Japanese (ja)
Inventor
周 堀
吉田　孝
年宏 中村
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太陽油脂株式会社
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Application filed by 太陽油脂株式会社 filed Critical 太陽油脂株式会社
Priority to SG11201901882WA priority Critical patent/SG11201901882WA/en
Priority to JP2018537434A priority patent/JP6817313B2/en
Priority to MYPI2019001124A priority patent/MY192324A/en
Publication of WO2018043701A1 publication Critical patent/WO2018043701A1/en

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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
    • 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
    • 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

Definitions

  • the present invention relates to an oil / fat composition used in 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.
  • 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 ⁇ g / 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 .5 g is used.
  • 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.
  • 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, ⁇ -linolenic acid, arachidonic acid, and docosahexaenoic acid necessary for infant growth.
  • linoleic acid a certain amount of essential fatty acids such as linoleic acid, ⁇ -linolenic acid, arachidonic acid, and docosahexaenoic acid necessary for infant growth.
  • 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 ⁇ -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. .
  • JP 2012-136655 A JP-A-7-107904 JP-A-2-231037
  • the oil and fat composition used in formulas for childcare has certain standards for linoleic acid and ⁇ -linolenic acid.
  • Polyunsaturated fatty acids such as linoleic acid and ⁇ -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 are distributed in the form of cans and containers and refrigerated (1 to 10 ° C.).
  • the oil and fat composition used in infant formula is not suitable for palm or lauric oils. When it contains, there exists a problem that the degradation odor at well-known low temperature will generate
  • the oil and fat composition used in the infant formula containing milk of palm or lauric oil is less likely to change in flavor even when distributed in refrigeration, and needs to have storage stability.
  • storage stability means that a change in flavor hardly occurs during distribution in refrigeration (1 to 10 ° C.) and has a good flavor even after distribution. Therefore, the problem of the present invention is that the concentration of 3-MCPD and glycidol and their fatty acid esters is sufficiently low, and further changes in flavor are unlikely to occur during distribution in refrigeration, excellent storage stability, and nutritionally constant. It is providing the oil-fat composition used for the infant formula milk powder which satisfy
  • the object of the present invention is achieved by an oil and fat composition comprising linoleic acid and ⁇ -linolenic acid, having a 3-MCPD concentration of 0.33 ppm or less and a glycidol concentration of 0.1 ppm or less, and having excellent storage stability.
  • an oil / fat composition can provide an oil / fat composition used for infant formula milk powder having excellent nutrition, safety and storage stability.
  • the above fat composition for infant formula which has a glycidol concentration of 0.1 ppm or less and hardly changes in flavor when stored refrigerated.
  • step (i) a first fat selected from deoxidized palm oil and its fractionated oil, and a first One or more other fats and oils optionally contained other than fats and oils are each decolorized, and then the decolored fats and oils are deodorized at 200 to 230 ° C., and the deodorized fats and oils are mixed. .
  • the mixed fats and oils of step (i) are not transesterified, and the first fats and oils selected from the deoxidized palm oil and the fractionated oils of step (ii), and any other than the first fats and oils
  • the production method according to [8], wherein none of the one or more other fats and oils contained in is transesterified.
  • the concentration of 3-MCPD and glycidol and their fatty acid esters which have a nutritional balance suitable as a formula for childcare, in particular having a certain amount of linoleic acid and ⁇ -linolenic acid, and wanting to reduce intake from the viewpoint of safety Is sufficiently reduced, and an oil and fat composition having excellent storage stability can be produced as an oil and fat composition 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, and sugar.
  • Fat contains a certain amount of essential fatty acids such as linoleic acid, ⁇ -linolenic acid, arachidonic acid, and docosahexaenoic acid that are necessary for infant growth. include.
  • the permissible standard for labeling infant formulas is 4.4 to 6.0 g of lipid, 0.3 to 1.4 g of linoleic acid, and ⁇ -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.
  • the infant formula using the oil and fat composition of the present invention contains linoleic acid and ⁇ -linolenic acid, more preferably 4.4 to 6.0 g of lipid and 0.3% of linoleic acid as a composition per 100 kcal. In an amount of ⁇ 1.4 g and ⁇ -linolenic acid in an amount of 0.05 g or more. That is, it is preferable that oleoleic acid contains linoleic acid in an amount of 5.0 to 32.0% by mass and ⁇ -linolenic acid in an amount of 0.8% by mass or more. There are various measurement methods for the amount of linoleic acid and ⁇ -linolenic acid in fats and oils.
  • reference oil analysis method (“Reference Oil Analysis Test Method” (2013 edition, published by Japan Oil Science Society), 2 4.4.2.2-2013 Fatty acid composition Value measured by FID temperature rising gas chromatograph method) is used.
  • the ratio of linoleic acid and ⁇ -linolenic acid (linoleic acid / ⁇ -linolenic acid) in the oil / fat composition is preferably in the range of 5 to 15 from a nutritional viewpoint.
  • the oil and fat composition used for the infant formula of the present invention has a 3-MCPD concentration of 0.33 ppm or less and a glycidol concentration of 0.1 ppm or less. More preferably, the 3-MCPD concentration is 0.25 ppm or less and the glycidol concentration is 0.07 ppm or less.
  • the oil and fat composition used in the infant formula for milking of the present invention is less likely to change in flavor when stored refrigerated.
  • the flavor at least one week after the start of storage is less likely to change compared to the initial flavor. More preferably, the flavor does not change easily for at least 2 weeks after refrigerated storage, more preferably the flavor does not change easily for at least 3 weeks after refrigerated storage, and even more preferably the flavor does not change easily for at least 4 weeks after refrigerated storage.
  • the flavor change mainly means a deteriorated odor during low temperature storage.
  • “a flavor change hardly occurs during refrigerated storage” refers to a case where there is almost no change compared to the initial flavor before the start of storage at a refrigerated temperature (about 1 to 10 ° C.).
  • Whether or not “a change in flavor is unlikely to occur during refrigerated storage” can be tested, for example, by the following method. 1. Put 70g of oil composition into a 100mL brown bottle and seal (cap) it. 2. The oil and fat composition placed in a 100 mL brown bottle is stored in a thermostat set at 5 ° C. 3. The flavor is confirmed 1 week, 2 weeks, 3 weeks, 4 weeks, 5 weeks, and 6 weeks from the start of storage. The flavor is evaluated according to the following criteria in five stages compared to the initial flavor. 5 points: no change in flavor 4 points: slight change in flavor 3 points: clear change in flavor 2 points: There is a deteriorated odor 1 point: There is a strong deteriorated odor 4. In the case of 5 points compared to the initial flavor, it is judged that a change in flavor is unlikely to occur.
  • the raw oil and fat of the oil and fat composition of the present invention can be selected and used so that the manufactured oil and fat composition satisfies the above-described characteristics.
  • 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 Bean oil, rapeseed oil, corn oil, sunflower oil, safflower oil, egoma oil, flaxseed oil, high oleic sunflower oil, high oleic rapeseed oil, high oleic safflower oil, cottonseed oil, rice bran oil, sesame oil, olive oil, peanut oil, cacao oil And vegetable oils such as fish oil, beef tallow, pork tallow and the like, and fractionated oils of these fats can also be used.
  • raw material fats and oils for producing the fat and oil composition of the present invention it is preferable to include a first fat and oil selected from deoxidized palm oil and its fractionated oil.
  • a first fat and oil selected from deoxidized palm oil and its fractionated oil In the deoxidation treatment, an alkaline aqueous solution is usually used as will be described later.
  • palm oil and palm kernel oil containing a large amount of acid acid, palm oil containing a large amount of lauric acid, and a large amount of soap are produced.
  • the oil is also removed together with the soap as alkaline foots, there is a problem that the yield is lowered. Therefore, purification by a distillation method or the like is often used, and these fats and oils are not usually deoxidized.
  • deoxidized palm oil when it is referred to as “deoxidized palm oil” with respect to the raw oil and fat, it is sufficient that it is at least deoxidized, and after deoxidizing, decolorization and / or deodorization by a known method. May be further made.
  • the oil is subjected to decolorization and deodorization after deoxidation.
  • the process in order to distinguish the decoloring process and the deodorizing process after the deoxidizing process in the raw material fats and oils from the decoloring process and the deodorizing process performed in the subsequent process, The process may be referred to as “treatment”, and the latter may be referred to as “second decolorization process” and “second deodorization process”.
  • the “deoxidation treatment” can be performed by a method known in the art, for example, by treating the crude oil with an alkaline aqueous solution such as an aqueous sodium hydroxide solution. More specifically, for example, an alkaline aqueous solution having a concentration of about 5% to 30% may be added and treated. The amount of alkali added can be appropriately determined depending on the amount of free fatty acid mixed therein.
  • the treatment time with the aqueous alkali solution is about 10 to 30 minutes, depending on the alkali concentration and treatment temperature.
  • the treatment with the alkaline aqueous solution can be performed at a temperature of about 60 to 80 ° C., but is preferably performed at the lowest possible temperature. For example, stirring can be performed at 70 to 75 ° C. for about 20 minutes. Alternatively, it may be performed at a high temperature of about 80 to 90 ° C. to shorten the processing time.
  • 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.
  • palm olein and palm double olein are used.
  • the 3-MCPD concentration can be sufficiently obtained as a formula powder for childcare. Oils and fats that can be lowered to a safe level and that are less likely to cause flavor changes during refrigerated storage and have excellent storage stability can be obtained.
  • the quantity of the 1st fats and oils (oil and fat selected from the deoxidized palm oil and its fractionation oil) in the raw material fats and oils for manufacturing the fat and oil composition of this invention is fat and oil composition.
  • the amount is preferably less than 50% by mass with respect to the total mass of the object.
  • 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.
  • a palm kernel oil or a fat other than the first fat a fat selected from deoxidized palm oil and its fractionated oil
  • 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.
  • palm kernel olein is used.
  • the mass ratio of the first fat / oil to the palm kernel oil or the fractionated oil thereof in the raw fat / oil for producing the fat / oil composition of the present invention is preferably 20/80 to 80/20, preferably 30/70 to 70 / 30 is more preferable, and 40/60 to 60/40 is even more preferable.
  • the raw oil and fat for producing the oil and fat composition of the present invention further contains other oil and fat in addition to the first oil and fat and palm kernel oil or fractionated oil thereof. Also good.
  • Other oils and fats are not limited as long as linoleic acid and ⁇ -linolenic acid fall within the permitted standards.
  • they are soybean oil and rapeseed oil.
  • the raw oil / fat for producing the oil / fat composition of the present invention contains a first oil / fat selected from deoxidized palm oil and its fractionated oil, A plurality of other fats and oils may optionally be included. Such fats and oils are not limited as long as linoleic acid and ⁇ -linolenic acid fall within the intended range.
  • palm kernel oil that is a lauric fat and its fractionated oil, coconut oil, soybean oil that is liquid oil
  • examples include rapeseed oil, corn oil, sunflower oil, safflower oil, egoma oil, linseed oil, high oleic sunflower oil, high oleic rapeseed oil, and high oleic safflower oil.
  • These fats and oils may be subjected to deoxidation treatment, decolorization treatment (first decolorization treatment) and deodorization treatment (first deodorization treatment), respectively.
  • the masses of the first fats and fats and one or more other fats and oils is preferably 20/80 to 80/20, more preferably 30/70 to 70/30, and still more preferably 40/60 to 60/40.
  • the fat composition of the present invention comprises a mixture of a first fat selected from deacidified palm oil and its fractionated oil, and optionally one or more other fats and oils.
  • a first fat selected from deacidified palm oil and its fractionated oil
  • optionally one or more other fats and oils are subjected to decoloring treatment (second decoloring treatment) and deodorizing treatment (second deodorizing treatment).
  • deodorizing treatment is preferably performed at 200 ° C. or higher and 230 ° C. or lower.
  • the oil and fat composition of the present invention can be used with or without transesterification, but the oil and fat composition of the present invention can sufficiently reduce the amount of 3-MCPD without transesterification. There is no need to process. Further, when the deacidified fat is used as the raw fat, it is more preferable to use it without transesterification because the amount of 3-MCPD may be increased by transesterification. Diesterification and free fatty acid will increase if transesterification of the deoxidized fats and oils. Deodorizing treatment of fats and oils with increased diglycerides increases the amount of 3-MCPD, so that the amount of 3-MCPD in the transesterified oil is higher than the amount of 3-MCPD in the de-acidified transesterified oil.
  • the oil / fat composition of the present invention comprises palm oil that has been subjected to the deoxidation treatment described above and further optionally decolorized (first decoloration), deodorized (first deodorization), and fractionated oil thereof
  • the oil / fat composition This manufacturing method includes the following steps. (i) producing a fat mixed with a first fat selected from deoxidized palm oil and its fractionated oil and one or more other fats and oils optionally included other than the first fat; and the mixed fat Decolorizing treatment (second decoloring treatment), and then deodorizing (second deodorizing treatment) the decolorized oil and fat at 200 ° C. or higher and 230 ° C.
  • the first fat selected from the oil and one or more other fats and oils optionally included other than the first fat are each decolorized (second decolored), and then the degreased fat is 200 ° C. or higher and 230 ° C.
  • a more preferable embodiment of the production method of the present invention is characterized by passing through at least the following steps (1) to (3).
  • Each process is a mixing process (1), a decoloring process (2), and a deodorizing process (3).
  • a mixed fat is prepared by blending the first fat selected from the deoxidized palm oil and its fractionated oil, and one or more other fats and oils optionally included.
  • the 1st fats and oils and other fats and oils contained arbitrarily after the following decoloring process and deodorizing process, you may create mixed fats and oils.
  • ⁇ Decolorization process (2)> The fats and oils obtained in the step (1) are decolorized according to a conventional method.
  • the adsorbent used for the decolorization treatment acid activated clay is preferably used.
  • the deodorization treatment step is not particularly limited except for the temperature condition (200 to 230 ° C.), and may be a vacuum steam distillation deodorization method usually used for deodorizing edible fats and oils.
  • the glycidol concentration is 0.1 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.
  • 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.
  • 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 concentration of 3-MCPD and glycidol and their fatty acid esters even after the deodorizing treatment step, the 3-MCPD concentration is 0.33 ppm or less, and the glycidol concentration is 0.1 ppm or less. And the flavor is also good.
  • 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 were measured as 3-MCPD and glycidol. Are used to express “3-MCPD concentration” and “glycidol concentration” in the oil and fat composition.
  • 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.
  • optional components include a protein source, a carbohydrate source, vitamins, minerals, and other nourishing elements.
  • the oil / fat composition of the present invention can be contained, for example, in an amount of 10 to 30% by mass in the infant formula, but is not limited thereto.
  • Example 1 35 parts by mass of palm olein (NBD palm olein) treated with deoxidizing / decoloring (first decoloring) / deodorizing (first deodorizing), 30 parts by mass of palm kernel olein, 20 parts by mass of soybean oil and 15 parts by mass of rapeseed oil are mixed.
  • NBD palm olein palm olein treated with deoxidizing / decoloring (first decoloring) / deodorizing (first deodorizing)
  • 30 parts by mass of palm kernel olein 20 parts by mass of soybean oil and 15 parts by mass of rapeseed oil are mixed.
  • 1.5 parts by mass of acid activated clay (trade name: Galeon Earth V2, manufactured by Mizusawa Chemical Co., Ltd.) was added to 100 parts of the oil and fat, and decolorization treatment (second decoloration 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
  • Example 2 The fats and oils having the composition according to the description in Table 1 were decolored and deodorized under the same conditions as in Example 1 to produce each fat and oil composition.
  • Example 1 a fat and oil having a composition according to Table 1 was used in Example 1 except that palm olein (RBD palm olein) treated with decoloring (first decoloring) and deodorizing (first deodorizing) was mixed.
  • RBD palm olein palm olein treated with decoloring (first decoloring) and deodorizing (first deodorizing) was mixed.
  • Each oil-fat composition was manufactured by decoloring and deodorizing under the same conditions as above.
  • 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 ⁇ m Injection volume: 2 ⁇ L 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.
  • 3-MCPD amount [ppm] quantitative value [ ⁇ g / 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 the measurement results of analysis [A] and analysis [B], the amount of glycidol was calculated by subtracting the amount of 3-MCPD from the amount of 3-MCPD-FS and multiplying by the glycidol conversion coefficient.
  • Glycidol amount [ppm] (3-MCPD-FS amount [A] ⁇ 3-MCPD amount [B]) ⁇ glycidol conversion coefficient t
  • the fatty acid composition was analyzed by a standard fat analysis method (2.4.2.2-2013 fatty acid composition FID temperature rising gas chromatograph method).

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  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
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Abstract

This invention addresses the problem of providing a fat composition to be used in infant formula that has a sufficiently low concentration of 3-MCPD, glycidol, and the fatty acid esters thereof, that has excellent storage stability, and that satisfies certain nutritional standards. The above problem is solved by a fat composition for use in infant formula containing linoleic acid and α-linolenic acid, wherein the concentration of 3-monochloropropane-1,2-diol (3-MCPD) is no more than 0.33 ppm and the concentration of glycidol is no more than 0.1 ppm, and the flavor of the fat composition does not easily change in refrigerated storage.

Description

育児用調製粉乳に用いるための油脂組成物Oil and fat composition for use in infant formula
　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 / fat composition used in 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 .5 g is used. 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 necessary for infant growth. According to the table 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. .
特開２０１２－１３６６５５号公報JP 2012-136655 A 特開平７－１０７９０４号公報JP-A-7-107904 特開平２－２３１０３７号公報JP-A-2-231037
　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。 As described in Patent Document 1, in an adult with a body 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 average daily fat intake for an infant weighing 6 kg is 36.0 g, the allowable concentration of 3-MCPD in the oil / 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.
　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の流通は缶やコンテナの容器形態で、冷蔵（１～１０℃）で行っているが、育児用調製粉乳に用いられる油脂組成物がパーム系あるいはラウリン系油脂を含む場合、この冷蔵温度での流通でも公知の低温での劣化臭が発生してしまうという問題がある。
　よって、パーム系あるいはラウリン系油脂を含む育児用調製粉乳に用いられる油脂組成物は、冷蔵での流通時においても風味変化が発生しにくく、保存安定性を有する必要がある。
　本明細書では、「保存安定性」は、冷蔵（１～１０℃）での流通時に風味変化が発生しにくく、流通後も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、更に冷蔵での流通時に風味変化が発生しにくい、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 above, the oil and fat composition used in formulas for childcare has certain 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 are distributed in the form of cans and containers and refrigerated (1 to 10 ° C.). However, the oil and fat composition used in infant formula is not suitable for palm or lauric oils. When it contains, there exists a problem that the degradation odor at well-known low temperature will generate | occur | produce even if it distribute | circulates at this refrigeration temperature.
Therefore, the oil and fat composition used in the infant formula containing milk of palm or lauric oil is less likely to change in flavor even when distributed in refrigeration, and needs to have storage stability.
In the present specification, “storage stability” means that a change in flavor hardly occurs during distribution in refrigeration (1 to 10 ° C.) and has a good flavor even after distribution.
Therefore, the problem of the present invention is that the concentration of 3-MCPD and glycidol and their fatty acid esters is sufficiently low, and further changes in flavor are unlikely to occur during distribution in refrigeration, excellent storage stability, and nutritionally constant. It is providing the oil-fat composition used for the infant formula milk powder which satisfy | fills these standards.
　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、３－ＭＣＰＤ濃度が０．３３ｐｐｍ以下でかつグリシドール濃度が０．１ｐｐｍ以下であり、保存安定性に優れた油脂組成物により達成され、かかる油脂組成物により、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しうる。 The object of the present invention is achieved by an oil and fat composition comprising linoleic acid and α-linolenic acid, having a 3-MCPD concentration of 0.33 ppm or less and a glycidol concentration of 0.1 ppm or less, and having excellent storage stability. Such an oil / fat composition can provide an oil / fat composition used for infant formula milk powder having excellent 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]　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、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０．１ｐｐｍ以下であり、冷蔵保存で風味変化が発生しにくい上記育児用調製粉乳用油脂組成物。
[２]　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、[１]に記載の育児用調製粉乳用油脂組成物。
[３]　冷蔵保存において、保存開始から少なくとも１週間後の風味が初期風味と比較して変化しない、[１]または[２]に記載の育児用調製粉乳用油脂組成物。
[４]　脱酸処理されたパーム油およびその分別油から選択される第１油脂を含む原料油脂を脱色・脱臭処理して得られた、[１]～[３]のいずれか一項に記載の育児用調製粉乳用油脂組成物。
[５]　脱臭処理が２００℃以上２３０℃以下で行われた、[１]～[４]のいずれか一項に記載の育児用調製粉乳用油脂組成物。
[６]　原料油脂がエステル交換されていない、[４]または[５]のいずれか一項に記載の育児用調製粉乳用油脂組成物。
[７]　[１]～[６]のいずれか一項に記載の育児用調製粉乳用油脂組成物を含む、育児用調製粉乳。
[８]　[１]～[６]のいずれか一項に記載の育児用調製粉乳用油脂組成物の製造方法であって、下記工程を含む方法：
　(i) 脱酸処理されたパーム油およびその分別油から選択される第１油脂、及び第１油脂以外の任意に含まれる一または複数の他の油脂を混合した油脂を製造し、前記混合油脂を脱色処理し、その後前記脱色処理した油脂を２００℃以上２３０℃以下で脱臭処理する工程、または
　(ii) 脱酸処理されたパーム油およびその分別油から選択される第１油脂、及び第１油脂以外の任意に含まれる一または複数の他の油脂を各々脱色処理し、その後前記脱色処理した油脂を２００℃以上２３０℃以下で各々脱臭処理して、前記脱臭処理された油脂を混合する工程。
[９]　工程(i)の混合油脂がエステル交換されておらず、かつ工程(ii)の脱酸処理されたパーム油およびその分別油から選択される第１油脂、及び第１油脂以外の任意に含まれる一または複数の他の油脂のいずれもエステル交換されていない、[８]記載の製造方法。 Other aspects of the present invention may be as follows.
[1] An oil and fat composition for use in infant formula containing linoleic acid and α-linolenic acid, having a 3-monochloropropane-1,2-diol (3-MCPD) concentration of 0.33 ppm or less The above fat composition for infant formula, which has a glycidol concentration of 0.1 ppm or less and hardly changes in flavor when stored refrigerated.
[2] The composition according to [1], wherein linoleic acid is contained in an amount of 5.0 to 32.0 mass% and α-linolenic acid is contained in an amount of 0.8 mass% or more with respect to the total mass of the oil or fat composition. Oil and fat composition for infant formula.
[3] The fat and oil composition for infant formulas according to [1] or [2], wherein in refrigerated storage, the flavor at least one week after the start of storage does not change compared to the initial flavor.
[4] The method according to any one of [1] to [3], obtained by decolorizing and deodorizing a raw oil / fat containing a first oil / fat selected from deoxidized palm oil and its fractionated oil Oil and fat composition for infant formula.
[5] The oil and fat composition for infant formulas according to any one of [1] to [4], wherein the deodorization treatment is performed at 200 ° C. or higher and 230 ° C. or lower.
[6] The oil / fat composition for infant formulas according to any one of [4] or [5], wherein the raw oil / fat is not transesterified.
[7] An infant formula containing the oil composition for infant formulas according to any one of [1] to [6].
[8] A method for producing an oil and fat composition for infant formulas according to any one of [1] to [6], comprising the following steps:
(i) producing a fat mixed with a first fat selected from deoxidized palm oil and its fractionated oil and one or more other fats and oils optionally included other than the first fat; and the mixed fat A step of deodorizing the degreased oil and fat at 200 ° C. to 230 ° C., or (ii) a first fat selected from deoxidized palm oil and its fractionated oil, and a first One or more other fats and oils optionally contained other than fats and oils are each decolorized, and then the decolored fats and oils are deodorized at 200 to 230 ° C., and the deodorized fats and oils are mixed. .
[9] The mixed fats and oils of step (i) are not transesterified, and the first fats and oils selected from the deoxidized palm oil and the fractionated oils of step (ii), and any other than the first fats and oils The production method according to [8], wherein none of the one or more other fats and oils contained in is transesterified.
　本発明により、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ており、更に、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油脂組成物を製造することができる。 According to the present invention, the concentration of 3-MCPD and glycidol and their fatty acid esters, 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 wanting to reduce intake from the viewpoint of safety Is sufficiently reduced, and an oil and fat composition having excellent storage stability can be produced as an oil and fat composition for infant formula.
＜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, and sugar. 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. include.
In the Consumer Affairs Agency, the permissible standard for labeling infant formulas is 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（「基準油脂分析試験法」（２０１３年版、日本油科学会発行）、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, more preferably 4.4 to 6.0 g of lipid and 0.3% of linoleic acid as a composition per 100 kcal. In an amount of ˜1.4 g and α-linolenic acid in an amount of 0.05 g or more. That is, it is preferable that oleoleic acid 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.
There are various measurement methods for the amount of linoleic acid and α-linolenic acid in fats and oils. In this specification, reference oil analysis method ("Reference Oil Analysis Test Method" (2013 edition, published by Japan Oil Science Society), 2 4.4.2.2-2013 Fatty acid composition Value measured by FID temperature rising gas chromatograph method) is used.
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は、３－ＭＣＰＤ濃度が０．３３ｐｐｍ以下でかつグリシドール濃度が０．１ｐｐｍ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０．０７ｐｐｍ以下である。 The oil and fat composition used for the infant formula of the present invention has a 3-MCPD concentration of 0.33 ppm or less and a glycidol concentration of 0.1 ppm or less. More preferably, the 3-MCPD concentration is 0.25 ppm or less and the glycidol concentration is 0.07 ppm or less.
　本発明の育児用調製粉乳に用いられる油脂組成物は、冷蔵保存で風味変化が発生しにくい。好ましくは、冷蔵保存で、保存開始から少なくとも１週間後の風味が初期風味と比較して変化しにくい。より好ましくは、冷蔵保存で少なくとも２週間風味が変化しにくく、更に好ましくは冷蔵保存で少なくとも３週間風味が変化しにくく、更により好ましくは冷蔵保存で少なくとも４週間風味が変化しにくい。
　本明細書において風味変化とは、主に、低温保存時の劣化臭のことを意味する。本明細書において、「冷蔵保存で風味変化が発生しにくい」とは、冷蔵温度（１～１０℃程度）で保存開始する前の初期風味と比較してほぼ変化が無い場合をいう。 The oil and fat composition used in the infant formula for milking of the present invention is less likely to change in flavor when stored refrigerated. Preferably, in refrigerated storage, the flavor at least one week after the start of storage is less likely to change compared to the initial flavor. More preferably, the flavor does not change easily for at least 2 weeks after refrigerated storage, more preferably the flavor does not change easily for at least 3 weeks after refrigerated storage, and even more preferably the flavor does not change easily for at least 4 weeks after refrigerated storage.
In the present specification, the flavor change mainly means a deteriorated odor during low temperature storage. In the present specification, “a flavor change hardly occurs during refrigerated storage” refers to a case where there is almost no change compared to the initial flavor before the start of storage at a refrigerated temperature (about 1 to 10 ° C.).
　「冷蔵保存で風味変化が発生しにくい」か否かについては、例えば以下の方法により試験を行うことができる。
１．１００ｍＬの褐色瓶に油脂組成物７０ｇを投入し、密閉（キャップ）をする。
２．１００ｍＬ褐色瓶に入れた油脂組成物を、５℃に設定された恒温槽に保存する。
３．保存開始から１週間、２週間、３週間、４週間、５週間、６週間で風味を確認する。
　風味は、以下の基準に則り、初期風味と比較した５段階で評価する。
　５点：風味変化無し
　４点：僅かに風味変化あり
　３点：明らかな風味変化あり 
　２点：劣化臭あり
　１点：強い劣化臭あり
４.初期風味と比較して５点の場合には、風味変化が発生しにくいと判断する。 Whether or not “a change in flavor is unlikely to occur during refrigerated storage” can be tested, for example, by the following method.
1. Put 70g of oil composition into a 100mL brown bottle and seal (cap) it.
2. The oil and fat composition placed in a 100 mL brown bottle is stored in a thermostat set at 5 ° C.
3. The flavor is confirmed 1 week, 2 weeks, 3 weeks, 4 weeks, 5 weeks, and 6 weeks from the start of storage.
The flavor is evaluated according to the following criteria in five stages compared to the initial flavor.
5 points: no change in flavor 4 points: slight change in flavor 3 points: clear change in flavor
2 points: There is a deteriorated odor 1 point: There is a strong deteriorated odor 4. In the case of 5 points compared to the initial flavor, it is judged that a change in flavor is unlikely to occur.
　本発明の油脂組成物の原料油脂としては、製造され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、ハイオレイックサフラワー油、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。 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 oils and fats 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 Bean oil, rapeseed oil, corn oil, sunflower oil, safflower oil, egoma oil, flaxseed oil, high oleic sunflower oil, high oleic rapeseed oil, high oleic safflower oil, cottonseed oil, rice bran oil, sesame oil, olive oil, peanut oil, cacao oil And vegetable oils such as fish oil, beef tallow, pork tallow and the like, and fractionated oils of these fats can also be used.
　本発明の油脂組成物を製造するための原料油脂としては、脱酸処理されたパーム油およびその分別油から選択される第１油脂を含むことが好ましい。
　脱酸処理では後述するようにアルカリ水溶液を使用することが通常であるが、アルカリ脱酸では、酸価の高いパーム油やラウリン酸を多く含むヤシ油、パーム核油は、多量の石けんが生成し、油も石けんと共にアルカリフーツとして除去されてしまうので、収量が低下するという問題があるため、蒸留法による精製などを用いることが多く、これらの油脂は通常脱酸処理がなされていない。 As raw material fats and oils for producing the fat and oil composition of the present invention, it is preferable to include a first fat and oil selected from deoxidized palm oil and its fractionated oil.
In the deoxidation treatment, an alkaline aqueous solution is usually used as will be described later. However, in alkali deoxidation, palm oil and palm kernel oil containing a large amount of acid acid, palm oil containing a large amount of lauric acid, and a large amount of soap are produced. However, since the oil is also removed together with the soap as alkaline foots, there is a problem that the yield is lowered. Therefore, purification by a distillation method or the like is often used, and these fats and oils are not usually deoxidized.
　本明細書において原料油脂に関して「脱酸処理されたパーム油」という場合には、少なくとも脱酸処理されていればよく、脱酸処理を行った後、公知の方法により脱色処理および／または脱臭処理が更になされていてもよい。好ましくは脱酸処理後、脱色処理及び脱臭処理を行った油脂である。本明細書では、原料油脂における脱酸処理後の脱色処理及び脱臭処理を、後の工程で行なわれる脱色処理及び脱臭処理と区別するために、前者を「第１脱色処理」及び「第１脱臭処理」と呼び、後者を「第２脱色処理」及び「第２脱臭処理」と呼ぶ場合がある。 In the present specification, when it is referred to as “deoxidized palm oil” with respect to the raw oil and fat, it is sufficient that it is at least deoxidized, and after deoxidizing, decolorization and / or deodorization by a known method. May be further made. Preferably, the oil is subjected to decolorization and deodorization after deoxidation. In this specification, in order to distinguish the decoloring process and the deodorizing process after the deoxidizing process in the raw material fats and oils from the decoloring process and the deodorizing process performed in the subsequent process, The process may be referred to as “treatment”, and the latter may be referred to as “second decolorization process” and “second deodorization process”.
　「脱酸処理」は、当該技術分野において公知の方法により行なうことができ、例えば、粗油を水酸化ナトリウム水溶液等のアルカリ水溶液により処理することにより行なうことができる。より具体的には、例えば約５％～３０％程度の濃度のアルカリ水溶液を添加して処理してもよい。アルカリ添加量は、混入している遊離脂肪酸の量などによって適宜決定することができる。アルカリ水溶液で処理する時間は、アルカリ濃度や処理温度にもよるが１０～３０分程度である。アルカリ水溶液で処理する温度は６０～８０℃程度で行うことができるが、出来る限り低い温度で行うことが好ましい。例えば、７０～７５℃で２０分程度撹拌することができる。あるいは８０～９０℃程度の高温で行い、処理時間を短縮してもよい。 The “deoxidation treatment” can be performed by a method known in the art, for example, by treating the crude oil with an alkaline aqueous solution such as an aqueous sodium hydroxide solution. More specifically, for example, an alkaline aqueous solution having a concentration of about 5% to 30% may be added and treated. The amount of alkali added can be appropriately determined depending on the amount of free fatty acid mixed therein. The treatment time with the aqueous alkali solution is about 10 to 30 minutes, depending on the alkali concentration and treatment temperature. The treatment with the alkaline aqueous solution can be performed at a temperature of about 60 to 80 ° C., but is preferably performed at the lowest possible temperature. For example, stirring can be performed at 70 to 75 ° C. for about 20 minutes. Alternatively, it may be performed at a high temperature of about 80 to 90 ° C. to shorten the processing time.
　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。
　脱酸処理されたパーム油およびその分別油から選択される第１油脂を本発明の油脂組成物を製造するための原料油脂として使用することにより、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、冷蔵保存で風味変化が発生しにくい保存安定性に優れた油脂を得ることができる。 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.
By using the first fat selected from the deoxidized palm oil and its fractionated oil as the raw fat for producing the fat composition of the present invention, the 3-MCPD concentration can be sufficiently obtained as a formula powder for childcare. Oils and fats that can be lowered to a safe level and that are less likely to cause flavor changes during refrigerated storage and have excellent storage stability can be obtained.
　本発明の１つの態様において、本発明の油脂組成物を製造するための原料油脂中の第１油脂（脱酸処理された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。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。 1 aspect of this invention WHEREIN: The quantity of the 1st fats and oils (oil and fat selected from the deoxidized palm oil and its fractionation oil) in the raw material fats and oils for manufacturing the fat and oil composition of this invention is fat and oil composition. The amount is preferably less than 50% by mass with respect to the total mass of the object. 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.
　本発明の他の態様において、本発明の油脂組成物を製造するための原料油脂として、第１油脂（脱酸処理されたパーム油およびその分別油から選択される油脂）以外にパーム核油またはその分別油を用いることが好ましい。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。
　本発明の油脂組成物を製造するための原料油脂中の第１油脂とパーム核油またはその分別油の質量比は、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。
　本発明の更なる他の態様において、本発明の油脂組成物を製造するための原料油脂は、第１油脂とパーム核油またはその分別油に加えて、さらに他の油脂を含むものであってもよい。他の油脂としては、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、ハイオレイックサフラワー油等が挙げられる。好ましくは、大豆油、菜種油である。 In another aspect of the present invention, as a raw material fat for producing the fat composition of the present invention, a palm kernel oil or a fat other than the first fat (a fat selected from deoxidized palm oil and its fractionated oil) It is preferable to use the fractionated oil. 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.
The mass ratio of the first fat / oil to the palm kernel oil or the fractionated oil thereof in the raw fat / oil for producing the fat / oil composition of the present invention is preferably 20/80 to 80/20, preferably 30/70 to 70 / 30 is more preferable, and 40/60 to 60/40 is even more preferable.
In still another embodiment of the present invention, the raw oil and fat for producing the oil and fat composition of the present invention further contains other oil and fat in addition to the first oil and fat and palm kernel oil or fractionated oil thereof. Also good. Other oils and fats are not limited as long as linoleic acid and α-linolenic acid fall within the permitted standards. For example, soybean oil, rapeseed oil, corn oil, sunflower oil, safflower oil, egoma oil, linseed oil, hyoleum Ic sunflower oil, high oleic rapeseed oil, high oleic safflower oil and the like. Preferably, they are soybean oil and rapeseed oil.
　本発明の更に他の態様では、本発明の油脂組成物を製造するための原料油脂は、脱酸処理されたパーム油およびその分別油から選択される第１油脂を含み、これ以外に一または複数の他の油脂を任意に含んでいてもよい。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、ラウリン系油脂であるパーム核油およびその分別油、ヤシ油、液油である大豆油、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、ハイオレイックサフラワー油等が挙げられる。好ましくは、パーム核油およびその分別油、大豆油、菜種油である。
　これらの油脂は、各々脱酸処理、脱色処理（第１脱色処理）及び脱臭処理（第１脱臭処理）がされていてもよい。 In still another aspect of the present invention, the raw oil / fat for producing the oil / fat composition of the present invention contains a first oil / fat selected from deoxidized palm oil and its fractionated oil, A plurality of other fats and oils may optionally be included. Such fats and oils are not limited as long as linoleic acid and α-linolenic acid fall within the intended range. For example, palm kernel oil that is a lauric fat and its fractionated oil, coconut oil, soybean oil that is liquid oil, Examples include rapeseed oil, corn oil, sunflower oil, safflower oil, egoma oil, linseed oil, high oleic sunflower oil, high oleic rapeseed oil, and high oleic safflower oil. Preference is given to palm kernel oil and its fractionated oil, soybean oil, and rapeseed oil.
These fats and oils may be subjected to deoxidation treatment, decolorization treatment (first decolorization treatment) and deodorization treatment (first deodorization treatment), respectively.
　本発明の油脂組成物を製造するための原料油脂に、第１油脂以外に、さらに一または複数の他の油脂が含まれている場合、第１油脂と一または複数の他の油脂との質量比は、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。 In the case where one or more other fats and oils are further contained in the raw material fats and oils for producing the oil and fat composition of the present invention in addition to the first fats and oils, the masses of the first fats and fats and one or more other fats and oils The ratio is preferably 20/80 to 80/20, more preferably 30/70 to 70/30, and still more preferably 40/60 to 60/40.
　本発明の他の態様では、本発明の油脂組成物は、脱酸処理されたパーム油およびその分別油から選択される第１油脂及び任意に含まれる一または複数の他の油脂の混合物からなる混合油脂から製造され、これらの混合油脂または各々の油脂として、脱色処理（第２脱色処理）及び脱臭処理（第２脱臭処理）される。脱臭処理は２００℃以上２３０℃以下で行なうことが好ましい。 In another aspect of the present invention, the fat composition of the present invention comprises a mixture of a first fat selected from deacidified palm oil and its fractionated oil, and optionally one or more other fats and oils. Manufactured from mixed fats and oils, these mixed fats or oils are subjected to decoloring treatment (second decoloring treatment) and deodorizing treatment (second deodorizing treatment). The deodorizing treatment is preferably performed at 200 ° C. or higher and 230 ° C. or lower.
　なお、本発明の油脂組成物はエステル交換してもしなくても用いることができるが、本発明の油脂組成物は、エステル交換をすることなく３－ＭＣＰＤ量を十分に低減できるため、エステル交換処理を行う必要がない。また、脱酸処理された油脂を原料油脂として用いた場合には、エステル交換により３－ＭＣＰＤ量が増える場合があるためエステル交換せずに用いることがより好ましい。脱酸処理された油脂をエステル交換すると、ジグリセリドや遊離脂肪酸が増加してしまう。ジグリセリドが増加した油脂を脱臭処理すると、３－ＭＣＰＤ量が増加するため、エステル交換油の３－ＭＣＰＤ量は、脱酸処理したエステル交換油の３－ＭＣＰＤ量よりも高くなってしまう。 The oil and fat composition of the present invention can be used with or without transesterification, but the oil and fat composition of the present invention can sufficiently reduce the amount of 3-MCPD without transesterification. There is no need to process. Further, when the deacidified fat is used as the raw fat, it is more preferable to use it without transesterification because the amount of 3-MCPD may be increased by transesterification. Diesterification and free fatty acid will increase if transesterification of the deoxidized fats and oils. Deodorizing treatment of fats and oils with increased diglycerides increases the amount of 3-MCPD, so that the amount of 3-MCPD in the transesterified oil is higher than the amount of 3-MCPD in the de-acidified transesterified oil.
＜油脂組成物の製造方法＞
　本発明の油脂組成物が上述した脱酸処理され、さらに任意に脱色処理（第１脱色処理）、脱臭処理（第１脱臭処理）されたパーム油およびその分別油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) 脱酸処理されたパーム油およびその分別油から選択される第１油脂、及び第１油脂以外の任意に含まれる一または複数の他の油脂を混合した油脂を製造し、前記混合油脂を脱色処理（第２脱色処理）し、その後前記脱色処理した油脂を２００℃以上２３０℃以下で脱臭処理（第２脱臭処理）する工程、または
　(ii) 脱酸処理されたパーム油およびその分別油から選択される第１油脂、及び第１油脂以外の任意に含まれる一または複数の他の油脂を各々脱色処理（第２脱色処理）し、その後前記脱色処理した油脂を２００℃以上２３０℃以下で各々脱臭処理（第２脱臭処理）して、前記脱臭処理された油脂を混合する工程。 <The manufacturing method of fats and oils composition>
In the aspect in which the oil / fat composition of the present invention comprises palm oil that has been subjected to the deoxidation treatment described above and further optionally decolorized (first decoloration), deodorized (first deodorization), and fractionated oil thereof, the oil / fat composition This manufacturing method includes the following steps.
(i) producing a fat mixed with a first fat selected from deoxidized palm oil and its fractionated oil and one or more other fats and oils optionally included other than the first fat; and the mixed fat Decolorizing treatment (second decoloring treatment), and then deodorizing (second deodorizing treatment) the decolorized oil and fat at 200 ° C. or higher and 230 ° C. or lower, or (ii) deoxidized palm oil and its separation The first fat selected from the oil and one or more other fats and oils optionally included other than the first fat are each decolorized (second decolored), and then the degreased fat is 200 ° C. or higher and 230 ° C. The process of performing the deodorizing process (2nd deodorizing process) below, and mixing the said deodorized fats and oils below.
　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、混合工程（１）、脱色処理工程（２）、脱臭処理工程（３）である。 A more preferable embodiment of the production method of the present invention is characterized by passing through at least the following steps (1) to (3). Each process is a mixing process (1), a decoloring process (2), and a deodorizing process (3).
　＜混合工程（１）＞
　脱酸処理されたパーム油およびその分別油から選択される第１油脂、及び任意に含まれる一または複数の他の油脂を配合して混合油脂を作成する。
　ここで、第１油脂及び任意に含まれる他の油脂の各々を以下の脱色処理工程および脱臭処理工程を経た後で配合して混合油脂を作成してもよい。 <Mixing step (1)>
A mixed fat is prepared by blending the first fat selected from the deoxidized palm oil and its fractionated oil, and one or more other fats and oils optionally included.
Here, after mixing the 1st fats and oils and other fats and oils contained arbitrarily after the following decoloring process and deodorizing process, you may create mixed fats and oils.
　＜脱色処理工程（２）＞
　工程（１）で得られた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 fats and oils obtained in the step (1) are decolorized according to a conventional method. As the adsorbent used for the decolorization treatment, acid activated clay is preferably used. 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.
　＜脱臭処理工程（３）＞
　脱臭処理工程は、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。
　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０．１ｐｐｍ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。 <Deodorization process (3)>
The deodorization treatment step is not particularly limited except for the temperature condition (200 to 230 ° C.), and may be a vacuum steam distillation deodorization method usually used for deodorizing edible fats and oils.
In the present invention, the glycidol concentration is 0.1 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.
　上記の製造方法により得られる油脂組成物は、脱臭処理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０．１ｐｐｍ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。 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 treatment step, the 3-MCPD concentration is 0.33 ppm or less, and the glycidol concentration is 0.1 ppm or less. And the flavor is also good.
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 the present specification, these were measured 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.
The oil / fat composition of the present invention can be contained, for example, in an amount of 10 to 30% by mass in the infant formula, but is not limited thereto.
（実施例１）
　脱酸・脱色（第１脱色）・脱臭（第１脱臭）処理されたパームオレイン（ＮＢＤパームオレイン）３５質量部、パーム核オレイン３０質量部、大豆油２０質量部及び菜種油１５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１．５質量部添加し、常圧下で、９０℃、６０分間脱色処理（第２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（第２脱臭処理）を行い冷却時に２５ｐｐｍのクエン酸を添加し、脱臭油を得た。 (Example 1)
35 parts by mass of palm olein (NBD palm olein) treated with deoxidizing / decoloring (first decoloring) / deodorizing (first deodorizing), 30 parts by mass of palm kernel olein, 20 parts by mass of soybean oil and 15 parts by mass of rapeseed oil are mixed. In addition, 1.5 parts by mass of acid activated clay (trade name: Galeon Earth V2, manufactured by Mizusawa Chemical Co., Ltd.) was added to 100 parts of the oil and fat, and decolorization treatment (second decoloration 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. 15 kg of this decolorized oil was subjected to deodorization treatment (second deodorization treatment) under conditions of 210 ° C., 75 minutes, vacuum degree of 0.4 kPa or less, and steam blown in 3.0% (weight% of oil). An acid was added to obtain a deodorized oil.
（実施例２、３）
　表１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 and 3)
The fats and oils having the composition according to the description in Table 1 were decolored and deodorized under the same conditions as in Example 1 to produce each fat and oil composition.
（比較例１、２、３）
　ＮＢＤパームオレインの代わりに、脱色（第１脱色）・脱臭（第１脱臭）処理されたパームオレイン（ＲＢＤパームオレイン）を混合した他は、表１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。 (Comparative Examples 1, 2, 3)
In place of NBD palm olein, a fat and oil having a composition according to Table 1 was used in Example 1 except that palm olein (RBD palm olein) treated with decoloring (first decoloring) and deodorizing (first deodorizing) was mixed. Each oil-fat composition was manufactured by decoloring and deodorizing under the same conditions as above.
　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、保存試験（風味）、脂肪酸組成分析も行った。分析結果を表２に示す。 For each oil and fat obtained in Examples and Comparative Examples, the content of 3-MCPD and glycidol was measured by the analysis method described later. In addition, flavor, storage test (flavor), and fatty acid composition analysis were also performed. The analysis results are shown in Table 2.
（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)
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 (about 1000ppm)
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 (approximately 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 surrogate, and the recovery rate was confirmed.
3) After adding 200 μL of sodium methoxide-methanol solution and stirring, the mixture was 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 the measurement results of analysis [A] and analysis [B], the amount of glycidol was calculated by subtracting the amount of 3-MCPD from the amount of 3-MCPD-FS and multiplying by the glycidol conversion coefficient.
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（風味）方法）
１．１００ｍＬの褐色瓶に油脂組成物７０ｇを投入し、密閉（キャップ）をした。
２．１００ｍＬ褐色瓶に入れた油脂組成物を、５℃に設定された恒温槽に保存した。
３．保存開始から１週間、２週間、３週間、４週間、５週間、６週間での風味を確認した。
　風味は、以下の基準に則り、初期風味と比較した５段階で評価した。評価は７人で行ない、平均値を四捨五入した値を表に示した。
　５点：風味変化無し
　４点：僅かに風味変化あり
　３点：明らかな風味変化あり
　２点：劣化臭あり
　１点：強い劣化臭あり (Preservation test (flavor) method)
1. Into a 100 mL brown bottle, 70 g of the oil / fat composition was charged and sealed (cap).
2. The oil and fat composition placed in a 100 mL brown bottle was stored in a thermostatic bath set at 5 ° C.
3. The flavor at 1 week, 2 weeks, 3 weeks, 4 weeks, 5 weeks, and 6 weeks from the start of storage was confirmed.
The flavor was evaluated according to the following criteria in five stages compared with the initial flavor. The evaluation was performed by 7 people, and the values obtained by rounding off the average values are shown in the table.
5 points: no change in flavor 4 points: slight change in flavor 3 points: clear change in flavor 2 points: deterioration odor 1 point: strong deterioration odor
（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 fat analysis method (2.4.2.2-2013 fatty acid composition FID temperature rising gas chromatograph method).
（結果）
　実施例１～３の油脂はいずれも５℃で６週間風味変化が無く、保存安定性に優れたものであった。
　これに対し、実施例１、３と同じ原料油脂組成であるがＮＢＤパームオレインを使用していない比較例１、３の油脂組成物は５℃で４週間で風味変化が発生しており、保存安定性に優れておらず、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２と同じ原料油脂組成であるが、ＮＢＤパームオレインを使用していない比較例２の油脂組成物は、５℃で３週間で風味変化が発生しており、保存安定性に優れておらず、３－ＭＣＰＤが許容濃度を大きく上回るものであった。 (result)
The fats and oils of Examples 1 to 3 were all excellent in storage stability with no change in flavor at 5 ° C. for 6 weeks.
On the other hand, the oil and fat composition of Comparative Examples 1 and 3 having the same raw material oil and fat composition as in Examples 1 and 3 but not using NBD palm olein had a flavor change in 5 weeks at 5 ° C. and stored. The stability was not excellent, and 3-MCPD greatly exceeded the allowable concentration. Moreover, although it is the same raw material fat composition as Example 2, the oil-fat composition of the comparative example 2 which does not use NBD palm olein has generate | occur | produced the flavor change in 5 weeks at 5 degreeC, and is excellent in storage stability. However, 3-MCPD greatly exceeded the allowable concentration.
Figure JPOXMLDOC01-appb-T000001
Figure JPOXMLDOC01-appb-T000001
Figure JPOXMLDOC01-appb-T000002
Figure JPOXMLDOC01-appb-T000002

Claims (7)

  1. 　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、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０．１ｐｐｍ以下であり、冷蔵保存（１～１０℃）で風味変化が発生しにくい上記育児用調製粉乳用油脂組成物。 An oil and fat composition for use in infant formula containing linoleic acid and α-linolenic acid, having a 3-monochloropropane-1,2-diol (3-MCPD) concentration of 0.33 ppm or less and a glycidol concentration The above fat composition for infant formula, which is 0.1 ppm or less and hardly changes in flavor when stored in a refrigerator (1 to 10 ° C.).
  2. 　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、請求項１に記載の育児用調製粉乳用油脂組成物。 The childcare product according to claim 1, comprising 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. Oil composition for prepared powdered milk.
  3. 　冷蔵保存において、保存開始から少なくとも１週間後の風味が初期風味と比較して変化しない、請求項１または２に記載の育児用調製粉乳用油脂組成物。 The oil and fat composition for infant formulas according to claim 1 or 2, wherein in refrigerated storage, the flavor at least one week after the start of storage does not change compared to the initial flavor.
  4. 　脱酸処理されたパーム油およびその分別油から選択される第１油脂を含む原料油脂を脱色・脱臭処理して得られた、請求項１～３のいずれか一項に記載の育児用調製粉乳用油脂組成物。 The infant formula according to any one of claims 1 to 3, obtained by decolorizing and deodorizing a raw oil / fat containing a first oil / fat selected from deoxidized palm oil and its fractionated oil. Oil and fat composition.
  5. 　脱臭処理が２００℃以上２３０℃以下で行われた、請求項１～４のいずれか一項に記載の育児用調製粉乳用油脂組成物。 The fat and oil composition for infant formulas according to any one of claims 1 to 4, wherein the deodorization treatment is performed at 200 ° C or higher and 230 ° C or lower.
  6. 　請求項１～５のいずれか一項に記載の育児用調製粉乳用油脂組成物を含む、育児用調製粉乳。 Child-rearing formula milk comprising the oil-fat composition for child-rearing formula milk according to any one of claims 1 to 5.
  7. 　請求項１～５のいずれか一項に記載の育児用調製粉乳用油脂組成物の製造方法であって、下記工程を含む方法：
    　(i) 脱酸処理されたパーム油およびその分別油から選択される第１油脂、及び第１油脂以外の任意に含まれる一または複数の他の油脂を混合した油脂を製造し、前記混合油脂を脱色処理し、その後前記脱色処理した油脂を２００℃以上２３０℃以下で脱臭処理する工程、または
    　(ii) 脱酸処理されたパーム油およびその分別油から選択される第１油脂、及び第１油脂以外の任意に含まれる一または複数の他の油脂を各々脱色処理し、その後前記脱色処理した油脂を２００℃以上２３０℃以下で各々脱臭処理して、前記脱臭処理された油脂を混合する工程。     A method for producing an oil-fat composition for infant formula milk according to any one of claims 1 to 5, comprising the following steps:
    (i) producing a fat mixed with a first fat selected from deoxidized palm oil and its fractionated oil and one or more other fats and oils optionally included other than the first fat; and the mixed fat A step of deodorizing the degreased oil and fat at 200 ° C. to 230 ° C., or (ii) a first fat selected from deoxidized palm oil and its fractionated oil, and a first One or more other fats and oils optionally contained other than fats and oils are each decolorized, and then the decolored fats and oils are deodorized at 200 to 230 ° C., and the deodorized fats and oils are mixed. .
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