WO2020189382A1 - Method for manufacturing transesterified oil/fat - Google Patents
Method for manufacturing transesterified oil/fat Download PDFInfo
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- WO2020189382A1 WO2020189382A1 PCT/JP2020/010068 JP2020010068W WO2020189382A1 WO 2020189382 A1 WO2020189382 A1 WO 2020189382A1 JP 2020010068 W JP2020010068 W JP 2020010068W WO 2020189382 A1 WO2020189382 A1 WO 2020189382A1
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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
-
- A—HUMAN NECESSITIES
- A21—BAKING; EDIBLE DOUGHS
- A21D—TREATMENT, e.g. PRESERVATION, OF FLOUR OR DOUGH, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS; PRESERVATION THEREOF
- A21D13/00—Finished or partly finished bakery products
- A21D13/40—Products characterised by the type, form or use
- A21D13/46—Croutons
Definitions
- the present invention relates to a method for producing transesterified fats and oils.
- Transesterified fats and oils are fats and oils obtained by exchanging the ester bond site between fatty acid and glycerin in the raw material fat and oil using a catalyst. Transesterified fats and oils are often used in plastic fat and oil compositions such as margarine and shortening.
- Patent Document 1 discloses a random transesterified oil / fat of a blended oil in which palm kernel oil and palm extremely hydrogenated oil are mixed at 70:30.
- a plastic oil / fat composition having a mixed oil / fat in which the random transesterified oil / fat and corn oil are mixed at a mass ratio of 60:40 is used as an oil phase to obtain a sugar cream having good creaming property and good taste. Is said to be possible.
- Patent Document 2 palm extremely hardened oil, palm oil, and palm kernel extremely hardened oil are mixed, sodium methylate is added as a catalyst, transesterification reaction is carried out under reduced pressure, and then washing with water, dehydration, and decolorization are performed. It is disclosed that transesterified fats and oils have been obtained, and they are used as plastic fats and oils in layered food fats and oils compositions.
- Patent Documents 1 and 2 disclose or suggest that transesterified oils and fats are attached to foods, especially foods having a crispy texture, and the flavor and texture of the foods.
- An object of the present invention is to provide a transesterified oil / fat that does not easily feel oily when attached to a food and improves the crispy texture of the food.
- the present invention comprises a step of obtaining an extremely hardened fat and oil of fat and oil A, an extremely hardened fat and oil of fat and oil B, and a mixed fat and oil containing fat and oil C.
- Including the transesterification step of the mixed fat and oil A method for producing transesterified fats and oils.
- the content of the extremely hardened fat A in the mixed fat is 35% by mass or more and 70% by mass or less.
- the content of the extremely hardened fat / oil B is 10% by mass or more and 45% by mass or less. This is the production method, wherein the content of fats and oils C is 15% by mass or more and 40% by mass or less.
- Fats and oils A Lauric acid-based fats and oils
- B Palm-based fats and oils
- C Edible fats and oils having a total content of oleic acid and linoleic acid in the constituent fatty acids of 65% by mass or more and 95% by mass or less.
- the present invention comprises a step of preparing a fat X composed of a fat A and a fat B, and The step of extremely curing the fat and oil after the step of preparing the fat and oil X, and A step of obtaining a mixed fat and oil containing the fat and oil and the fat and oil C after the step of being extremely cured, and Including the transesterification step of the mixed fat and oil, A method for producing transesterified fats and oils.
- the content of the fat A in the fat X is 40% by mass or more and 88% by mass or less.
- the content of the fat and oil B is 12% by mass or more and 60% by mass or less.
- the content of the fats and oils after the step of being extremely hardened in the mixed fats and oils is 60% by mass or more and 85% by mass or less.
- the linoleic acid content in the constituent fatty acids of the fat and oil C is preferably 30% by mass or more and 80% by mass or less.
- the fat and oil C contains one or more selected from the group consisting of corn oil, soybean oil and rice oil.
- the transesterification step is preferably a non-selective transesterification step.
- the present invention is also a method for producing a food product containing transesterified fats and oils obtained by the above-mentioned production method.
- the ester-exchanged fats and oils produced by a specific production method do not easily feel oily when attached to foods, and improve the crispness of the foods to which the ester-exchanged fats and oils are attached. Can be made to.
- the first invention of the present application is a step of obtaining an extremely hardened fat and oil of fat and oil A, an extremely hardened fat and oil of fat and oil B, and a mixed fat and oil containing fat and oil C.
- Including the transesterification step of the mixed fat and oil A method for producing transesterified fats and oils.
- the content of the extremely hardened fat A in the mixed fat is 35% by mass or more and 70% by mass or less.
- the content of the extremely hardened fat / oil B is 10% by mass or more and 45% by mass or less. This is the production method, wherein the content of fats and oils C is 15% by mass or more and 40% by mass or less.
- Fats and oils A Lauric acid-based fats and oils
- B Palm-based fats and oils
- C Edible fats and oils having a total content of oleic acid and linoleic acid in the constituent fatty acids of 65% by mass or more and 95% by mass or less.
- the fat and oil A is a lauric-based fat and oil, and is one or more selected from the group consisting of, for example, palm kernel oil, coconut oil, and processed fats and oils which have been subjected to processing such as fractionation, hydrogenation, and transesterification. It may be a lauric oil or fat.
- the fat A is preferably one or more selected from the group consisting of palm kernel oil, coconut oil, palm kernel fractionated oil, and palm fractionated oil, and one or more selected from the group consisting of palm kernel oil and coconut oil. Two are more preferred, and palm kernel oil is even more preferred.
- the extremely hardened fat and oil A can be obtained by hydrogenating the fat and oil A by a conventional method. For example, a method of hydrogenating until the iodine value becomes substantially 0 using a metal catalyst such as nickel or platinum can be mentioned.
- the fats and oils B are palm-based fats and oils, and are, for example, one or more palm-based fats and oils selected from the group consisting of palm oils and processed fats and oils that have been subjected to processing such as separation, hydrogenation, and transesterification. It may be there.
- the oil / fat B is preferably one or two selected from the group consisting of palm oil and palm fractionated oil, and more preferably palm oil.
- the extremely hardened fat and oil of fat and oil B can be obtained by the same method as the extremely hardened fat and oil of fat and oil A.
- the fat and oil C is an edible fat and oil in which the total content of oleic acid and linoleic acid in its constituent fatty acids is 65% by mass or more and 95% by mass or less.
- the total content of oleic acid and linoleic acid in the constituent fatty acids of the fat and oil C is preferably 70% by mass or more and 90% by mass or less, and more preferably 75% by mass or more and 85% by mass or less.
- the linoleic acid content in the constituent fatty acids in the fat C is preferably 30% by mass or more and 80% by mass or less, more preferably 30% by mass or more and 70% by mass or less, and 40% by mass or more. It is more preferably 60% by mass or less.
- the crispy texture of the food to which the obtained transesterified oil and fat is attached can be improved.
- the contents of oleic acid and linoleic acid in the constituent fatty acids can be measured according to the standard fat analysis test method 2.4.2.3-2013.
- any raw material fat or oil may be used as long as the total content of oleic acid and linoleic acid in the constituent fatty acids is 65% by mass or more and 95% by mass or less.
- it may contain one or more of soybean oil, rapeseed oil, cotton seed oil, corn oil, rice oil, peanut oil, sunflower oil, safflower oil, sesame oil, olive oil, etc., and may contain soybean oil, cotton seed oil, corn oil, etc.
- Corn oil is even more preferred, and corn oil is even more preferred.
- the mixed fat and oil includes the extremely hardened fat and oil of fat and oil A, the extremely hardened fat and oil of fat and oil B, and the fat and oil C.
- the mixed fat and oil is preferably composed of the extremely hardened fat and oil of fat and oil A, the extremely hardened fat and oil of fat and oil B, and the fat and oil C.
- any two kinds of fats and oils of the extremely hardened fats and oils A, the extremely hardened fats and oils B, and the fats and oils C are transesterified, and then another fat and oil is transesterified. It may include a step of mixing.
- the content of the extremely hardened fat A in the mixed fat is 35% by mass or more and 70% by mass or less, preferably 37% by mass or more and 70% by mass or less, and 40% by mass or more and 60% by mass or less. It is more preferable that it is 40% by mass or more and 50% by mass or less.
- the content of the extremely hardened fat and oil in the fat and oil A in the mixed fat and oil is within the above range, the crispy feeling of the food to which the obtained transesterified fat and oil is attached can be improved.
- the content of the extremely hardened fat and oil in the fat and oil B in the mixed fat and oil is 10% by mass or more and 45% by mass or less, preferably 10% by mass or more and 43% by mass or less, and 20% by mass or more and 40% by mass or less. It is more preferable that it is 30% by mass or more and 40% by mass or less.
- the content of fats and oils C in the mixed fats and oils is preferably 15% by mass or more and 40% by mass or less, preferably 18% by mass or more and 37% by mass or less, and more preferably 20% by mass or more and 35% by mass or less. preferable.
- content of the oil and fat C in the mixed oil and fat is within the above range, when the obtained transesterified oil and fat is attached to the food, it is difficult to feel the oiliness, and the transesterified oil and fat is attached. The crispness of food can be improved.
- the transesterification step may be a non-selective transesterification step or a position-specific transesterification step, but a non-selective transesterification step is preferable.
- the catalyst used in the non-selective transesterification step include chemical catalysts such as sodium methoxide, sodium ethoxide, and sodium hydroxide; and enzyme catalysts such as Lipozyme (registered trademark) TL IM.
- the second invention of the present application is a step of preparing a fat X composed of a fat A and a fat B, and The step of extremely curing the fat and oil after the step of preparing the fat and oil X, and A step of obtaining a mixed fat and oil containing the fat and oil and the fat and oil C after the step of being extremely cured, and Including the transesterification step of the mixed fat and oil, This is a method for producing transesterified fats and oils.
- the fat A, the fat B, the fat C, and the transesterification step in the second invention of the present application are as described in the first invention of the present application.
- the step of extremely curing may include a step of transesterifying the fat and oil X.
- the content of the fat A in the fat X is 40% by mass or more and 88% by mass or less, preferably 43% by mass or more and 80% by mass or less, and 46% by mass or more and 70% by mass or less. More preferably, it is 50% by mass or more and 65% by mass or less.
- the content of the fat and oil B in the fat and oil X is 12% by mass or more and 60% by mass or less, preferably 20% by mass or more and 57% by mass or less, and 30% by mass or more and 54% by mass or less. More preferably, it is more preferably 35% by mass or more and 50% by mass or less.
- the mixed fat and oil contains the fat and oil after the step of being extremely hardened and the fat and oil C, and is preferably composed of the fat and oil after the step of being extremely hardened and the fat and oil C.
- the content of the fats and oils after the step of being extremely cured in the mixed fats and oils is 60% by mass or more and 85% by mass or less, and preferably 65% by mass or more and 85% by mass or less.
- the content of the fat and oil C in the mixed fat and oil is preferably 15% by mass or more and 40% by mass or less, and preferably 15% by mass or more and 35% by mass or less.
- the content of the oil and fat C in the mixed oil and fat is within the above range, when the obtained transesterified oil and fat is attached to the food, it is difficult to feel the oiliness, and the transesterified oil and fat is attached. The crispness of food can be improved.
- the transesterified fats and oils obtained by the production method of the present invention are suitably used for foods in which a crispy texture is preferred.
- foods include croutons, rusks, biscotti, fried foods, rice crackers, cookies, biscuits and the like.
- the means for incorporating the transesterified oil and fat into the food product is not limited, but means for impregnating, coating, spraying, dropping, oiling and the like are preferable.
- the food to which the transesterified oil and fat is attached is less likely to feel oily and the crispy feeling is improved.
- the transesterified fats and oils obtained by the production method of the present invention can also be used as an edible fats and oils composition mixed with other edible fats and oils, foodstuffs other than edible fats and oils, food additives and the like.
- the edible oil / fat composition can be used as, for example, frying oil, margarine or shortening.
- Corn oil (oleic acid content: 39% by mass, linoleic acid content: 57% by mass, manufactured by J-Oil Mills Co., Ltd.) Palm oil (oleic acid content: 39% by mass, linoleic acid content: 9% by mass, manufactured by J-Oil Mills Co., Ltd.) Palm kernel oil (oleic acid content: 14% by mass, linoleic acid content: 2% by mass, manufactured by J-Oil Mills Co., Ltd.) Palm extremely hydrogenated oil (manufactured by Yokoseki Yushi Kogyo Co., Ltd.) Palm kernel extremely hardened oil (in-house preparation of J-Oil Mills Co., Ltd.)
- transesterified oil 1 A mixed fat and oil was prepared by mixing 100 parts by mass of palm kernel oil and 60 parts by mass of palm oil. To 100 parts by mass of the mixed fat and oil, 0.3 part by mass of sodium methoxide was added as a catalyst, and a random transesterification reaction was carried out while stirring at 80 ° C. and a vacuum degree of 2.7 kPa for 60 minutes. After the random transesterification reaction, the catalyst was removed by washing with water, and hydrogenation was performed until the oil became extremely hydrogenated. After hydrogenation, decolorization treatment was performed using activated clay, and further deodorization treatment was performed to obtain transesterified fats and oils 1.
- transesterified oil and fat 2 A mixed fat and oil was prepared by mixing 80 parts by mass of transesterified fat and oil 1 and 20 parts by mass of corn oil. To 100 parts by mass of the mixed fat and oil, 0.3 part by mass of sodium methoxide was added as a catalyst, and a random transesterification reaction was carried out while stirring at 80 ° C. and a vacuum degree of 2.7 kPa for 60 minutes. After the random transesterification reaction, the catalyst was removed by washing with water, decolorization treatment was performed using activated clay, and further deodorization treatment was performed to obtain transesterified fats and oils 2.
- transesterified oil and fat 3 The same method as for the preparation of transesterified fat 2 except that the mixed fat described in the preparation of transesterified fat 2 was changed to a mixed fat obtained by mixing 80 parts by mass of transesterified fat 1 and 20 parts by mass of palm oil. A transesterified oil and fat 3 was obtained.
- transesterified fat 4 (Preparation of transesterified fat 4) Esters except that the mixed fats and oils described in the preparation of transesterified fats and oils 2 were changed to mixed fats and oils obtained by mixing 40 parts by mass of palm core extremely hardened oil, 40 parts by mass of palm nucleus extremely hardened oil, and 20 parts by mass of corn oil. The transesterified oil 4 was obtained in the same manner as in the preparation of the transesterified oil 2.
- the croutons After impregnating the oil and fat, the croutons are placed in a plastic bag with a chuck and stored at 20 ° C for 24 hours, and then eaten by three specialized panelists. The flavor, crispness, and oiliness are discussed according to the following evaluation criteria. I evaluated it above. The evaluation results are shown in Table 1.
- Oil absorption (mass%) (M2-M1) / M1 ⁇ 100
- Comparative Example 1 in which the total content of oleic acid and linoleic acid in the constituent fatty acids is 48% by mass, which is a transesterified oil and fat of palm oil and extremely hydrogenated oil, and Comparative Example 2 in which an extremely hardened oil and fat are impregnated after the ester exchange. Although the crouton felt almost no oily, it had a bad flavor and was too hard, so it had a poor crispy texture.
- the croutons of Comparative Example 3 impregnated with fats and oils obtained by mixing extremely hardened fats and oils and corn oil after transesterification had a good flavor and a crispy texture, but were slightly oily.
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Abstract
Provided is a method for manufacturing a transesterified oil/fat that is capable of, when stuck to a food, imparting little oiliness and improving the crispy texture of the food. The method for manufacturing a transesterified oil/fat, said method comprising a step for obtaining a mixed oil/fat containing an extremely hardened oil/fat of oil/fat A, an extremely hardened oil/fat of oil/fat B and oil/fat C and a step for transesterifying the mixed oil/fat, wherein, in the mixed oil/fat, the content of the extremely hardened oil/fat of oil/fat A is 35-70 mass% inclusive, the content of the extremely hardened oil/fat of oil/fat B is 10-45 mass% inclusive and the content of oil/fat C is 15-40 mass% inclusive. Oil/fat A: a laurin-based oil/fat. Oil/fat B: a palm-based oil/fat. Oil/fat C: an edible oil/fat wherein, in the constituting fatty acids thereof, the total content of oleic acid and linolic acid is 65-95 mass% inclusive.
Description
本発明は、エステル交換油脂の製造方法に関する。
The present invention relates to a method for producing transesterified fats and oils.
エステル交換油脂は、触媒を使って、原料油脂中の脂肪酸とグリセリンとのエステル結合の部位を交換して得られる油脂である。エステル交換油脂は、マーガリンやショートニングといった可塑性油脂組成物によく利用されている。
Transesterified fats and oils are fats and oils obtained by exchanging the ester bond site between fatty acid and glycerin in the raw material fat and oil using a catalyst. Transesterified fats and oils are often used in plastic fat and oil compositions such as margarine and shortening.
例えば、特許文献１では、パーム核油とパーム極度硬化油を７０：３０で混合した配合油のランダムエステル交換油脂が開示されている。該ランダムエステル交換油脂とコーン油を６０：４０の質量比で混合した混合油脂を油相とした可塑性油脂組成物は、クリーミング性が良好であり、呈味性が良好であるシュガークリームを得ることができるとされている。一方、特許文献２では、パーム極度硬化油、パーム油、パーム核極度硬化油を混合し、触媒としてナトリウムメチラートを添加し、減圧下で、エステル交換反応した後、水洗、脱水、脱色しエステル交換油脂を得たことが開示されており、可塑性油脂として層状食品用油脂組成物に使用されている。
For example, Patent Document 1 discloses a random transesterified oil / fat of a blended oil in which palm kernel oil and palm extremely hydrogenated oil are mixed at 70:30. A plastic oil / fat composition having a mixed oil / fat in which the random transesterified oil / fat and corn oil are mixed at a mass ratio of 60:40 is used as an oil phase to obtain a sugar cream having good creaming property and good taste. Is said to be possible. On the other hand, in Patent Document 2, palm extremely hardened oil, palm oil, and palm kernel extremely hardened oil are mixed, sodium methylate is added as a catalyst, transesterification reaction is carried out under reduced pressure, and then washing with water, dehydration, and decolorization are performed. It is disclosed that transesterified fats and oils have been obtained, and they are used as plastic fats and oils in layered food fats and oils compositions.
一方で、特許文献１、２ともに、食品、特にサクサク感が好まれる食品にエステル交換油脂を付着させること、及び該食品の風味や食感について開示も示唆もされていない。
On the other hand, neither Patent Documents 1 and 2 disclose or suggest that transesterified oils and fats are attached to foods, especially foods having a crispy texture, and the flavor and texture of the foods.
本発明の目的は、食品に付着させた際に、油っぽさを感じにくく、食品のサクサクした食感を向上させるエステル交換油脂を提供することにある。
An object of the present invention is to provide a transesterified oil / fat that does not easily feel oily when attached to a food and improves the crispy texture of the food.
本発明者らは、上記課題を解決するために鋭意検討した結果、特定の製造方法により製造されるエステル交換油脂を食品に付着させれば、油っぽさを感じさせにくく、該食品のサクサク感を向上させることを見出し、本発明を完成した。
As a result of diligent studies to solve the above problems, the present inventors have made that if transesterified oils and fats produced by a specific production method are attached to a food, it is difficult to make the food feel oily, and the food is crispy. We have found to improve the feeling and completed the present invention.
すなわち、本発明は、油脂Ａの極度硬化油脂、油脂Ｂの極度硬化油脂、及び油脂Ｃを含む混合油脂を得る工程と、
前記混合油脂のエステル交換工程と、を含む、
エステル交換油脂の製造方法であって、
前記混合油脂中の
油脂Ａの前記極度硬化油脂の含有量が３５質量％以上７０質量％以下、
油脂Ｂの前記極度硬化油脂の含有量が１０質量％以上４５質量％以下、
油脂Ｃの含有量が１５質量％以上４０質量％以下である、前記製造方法である。
油脂Ａ：ラウリン系油脂
油脂Ｂ：パーム系油脂
油脂Ｃ：構成脂肪酸中のオレイン酸及びリノール酸の合計含有量が６５質量％以上９５質量％以下の食用油脂 That is, the present invention comprises a step of obtaining an extremely hardened fat and oil of fat and oil A, an extremely hardened fat and oil of fat and oil B, and a mixed fat and oil containing fat and oil C.
Including the transesterification step of the mixed fat and oil,
A method for producing transesterified fats and oils.
The content of the extremely hardened fat A in the mixed fat is 35% by mass or more and 70% by mass or less.
The content of the extremely hardened fat / oil B is 10% by mass or more and 45% by mass or less.
This is the production method, wherein the content of fats and oils C is 15% by mass or more and 40% by mass or less.
Fats and oils A: Lauric acid-based fats and oils B: Palm-based fats and oils C: Edible fats and oils having a total content of oleic acid and linoleic acid in the constituent fatty acids of 65% by mass or more and 95% by mass or less.
前記混合油脂のエステル交換工程と、を含む、
エステル交換油脂の製造方法であって、
前記混合油脂中の
油脂Ａの前記極度硬化油脂の含有量が３５質量％以上７０質量％以下、
油脂Ｂの前記極度硬化油脂の含有量が１０質量％以上４５質量％以下、
油脂Ｃの含有量が１５質量％以上４０質量％以下である、前記製造方法である。
油脂Ａ：ラウリン系油脂
油脂Ｂ：パーム系油脂
油脂Ｃ：構成脂肪酸中のオレイン酸及びリノール酸の合計含有量が６５質量％以上９５質量％以下の食用油脂 That is, the present invention comprises a step of obtaining an extremely hardened fat and oil of fat and oil A, an extremely hardened fat and oil of fat and oil B, and a mixed fat and oil containing fat and oil C.
Including the transesterification step of the mixed fat and oil,
A method for producing transesterified fats and oils.
The content of the extremely hardened fat A in the mixed fat is 35% by mass or more and 70% by mass or less.
The content of the extremely hardened fat / oil B is 10% by mass or more and 45% by mass or less.
This is the production method, wherein the content of fats and oils C is 15% by mass or more and 40% by mass or less.
Fats and oils A: Lauric acid-based fats and oils B: Palm-based fats and oils C: Edible fats and oils having a total content of oleic acid and linoleic acid in the constituent fatty acids of 65% by mass or more and 95% by mass or less.
また、本発明は、油脂Ａと油脂Ｂからなる油脂Ｘを準備する工程と、
油脂Ｘを準備する前記工程後の油脂を極度硬化する工程と、
極度硬化する前記工程後の油脂と油脂Ｃとを含む混合油脂を得る工程と、
前記混合油脂のエステル交換工程と、を含む、
エステル交換油脂の製造方法であって、
前記油脂Ｘ中の
前記油脂Ａの含有量が４０質量％以上８８質量％以下、
前記油脂Ｂの含有量が１２質量％以上６０質量％以下であり、
前記混合油脂中の
極度硬化する前記工程後の油脂の含有量が６０質量％以上８５質量％以下、
前記油脂Ｃの含有量が１５質量％以上４０質量％以下である、前記製造方法である。
油脂Ａ：ラウリン系油脂
油脂Ｂ：パーム系油脂
油脂Ｃ：構成脂肪酸中のオレイン酸及びリノール酸の合計含有量が６５質量％以上９５質量％以下の食用油脂 Further, the present invention comprises a step of preparing a fat X composed of a fat A and a fat B, and
The step of extremely curing the fat and oil after the step of preparing the fat and oil X, and
A step of obtaining a mixed fat and oil containing the fat and oil and the fat and oil C after the step of being extremely cured, and
Including the transesterification step of the mixed fat and oil,
A method for producing transesterified fats and oils.
The content of the fat A in the fat X is 40% by mass or more and 88% by mass or less.
The content of the fat and oil B is 12% by mass or more and 60% by mass or less.
The content of the fats and oils after the step of being extremely hardened in the mixed fats and oils is 60% by mass or more and 85% by mass or less.
The production method, wherein the content of the fat and oil C is 15% by mass or more and 40% by mass or less.
Fats and oils A: Lauric acid-based fats and oils B: Palm-based fats and oils C: Edible fats and oils having a total content of oleic acid and linoleic acid in the constituent fatty acids of 65% by mass or more and 95% by mass or less.
油脂Ｘを準備する前記工程後の油脂を極度硬化する工程と、
極度硬化する前記工程後の油脂と油脂Ｃとを含む混合油脂を得る工程と、
前記混合油脂のエステル交換工程と、を含む、
エステル交換油脂の製造方法であって、
前記油脂Ｘ中の
前記油脂Ａの含有量が４０質量％以上８８質量％以下、
前記油脂Ｂの含有量が１２質量％以上６０質量％以下であり、
前記混合油脂中の
極度硬化する前記工程後の油脂の含有量が６０質量％以上８５質量％以下、
前記油脂Ｃの含有量が１５質量％以上４０質量％以下である、前記製造方法である。
油脂Ａ：ラウリン系油脂
油脂Ｂ：パーム系油脂
油脂Ｃ：構成脂肪酸中のオレイン酸及びリノール酸の合計含有量が６５質量％以上９５質量％以下の食用油脂 Further, the present invention comprises a step of preparing a fat X composed of a fat A and a fat B, and
The step of extremely curing the fat and oil after the step of preparing the fat and oil X, and
A step of obtaining a mixed fat and oil containing the fat and oil and the fat and oil C after the step of being extremely cured, and
Including the transesterification step of the mixed fat and oil,
A method for producing transesterified fats and oils.
The content of the fat A in the fat X is 40% by mass or more and 88% by mass or less.
The content of the fat and oil B is 12% by mass or more and 60% by mass or less.
The content of the fats and oils after the step of being extremely hardened in the mixed fats and oils is 60% by mass or more and 85% by mass or less.
The production method, wherein the content of the fat and oil C is 15% by mass or more and 40% by mass or less.
Fats and oils A: Lauric acid-based fats and oils B: Palm-based fats and oils C: Edible fats and oils having a total content of oleic acid and linoleic acid in the constituent fatty acids of 65% by mass or more and 95% by mass or less.
前記油脂Ｃの構成脂肪酸中のリノール酸含有量が３０質量％以上８０質量％以下であることが好ましい。
The linoleic acid content in the constituent fatty acids of the fat and oil C is preferably 30% by mass or more and 80% by mass or less.
前記油脂Ｃがコーン油、大豆油及び米油からなる群から選択される１種または２種以上を含むことが好ましい。
It is preferable that the fat and oil C contains one or more selected from the group consisting of corn oil, soybean oil and rice oil.
エステル交換工程は非選択的エステル交換工程であることが好ましい。
The transesterification step is preferably a non-selective transesterification step.
本発明はまた、前記製造方法で得られたエステル交換油脂を含む食品の製造方法である。
The present invention is also a method for producing a food product containing transesterified fats and oils obtained by the above-mentioned production method.
本発明によれば、特定の製造方法により製造されるエステル交換油脂は、食品に付着させた際に、油っぽさを感じさせにくく、該エステル交換油脂を付着させた食品のサクサク感を向上させることができる。
According to the present invention, the ester-exchanged fats and oils produced by a specific production method do not easily feel oily when attached to foods, and improve the crispness of the foods to which the ester-exchanged fats and oils are attached. Can be made to.
本願の第一の発明は、油脂Ａの極度硬化油脂、油脂Ｂの極度硬化油脂及び油脂Ｃを含む混合油脂を得る工程と、
前記混合油脂のエステル交換工程と、を含む、
エステル交換油脂の製造方法であって、
前記混合油脂中の
油脂Ａの前記極度硬化油脂の含有量が３５質量％以上７０質量％以下、
油脂Ｂの前記極度硬化油脂の含有量が１０質量％以上４５質量％以下、
油脂Ｃの含有量が１５質量％以上４０質量％以下である、前記製造方法である。
油脂Ａ：ラウリン系油脂
油脂Ｂ：パーム系油脂
油脂Ｃ：構成脂肪酸中のオレイン酸及びリノール酸の合計含有量が６５質量％以上９５質量％以下の食用油脂 The first invention of the present application is a step of obtaining an extremely hardened fat and oil of fat and oil A, an extremely hardened fat and oil of fat and oil B, and a mixed fat and oil containing fat and oil C.
Including the transesterification step of the mixed fat and oil,
A method for producing transesterified fats and oils.
The content of the extremely hardened fat A in the mixed fat is 35% by mass or more and 70% by mass or less.
The content of the extremely hardened fat / oil B is 10% by mass or more and 45% by mass or less.
This is the production method, wherein the content of fats and oils C is 15% by mass or more and 40% by mass or less.
Fats and oils A: Lauric acid-based fats and oils B: Palm-based fats and oils C: Edible fats and oils having a total content of oleic acid and linoleic acid in the constituent fatty acids of 65% by mass or more and 95% by mass or less.
前記混合油脂のエステル交換工程と、を含む、
エステル交換油脂の製造方法であって、
前記混合油脂中の
油脂Ａの前記極度硬化油脂の含有量が３５質量％以上７０質量％以下、
油脂Ｂの前記極度硬化油脂の含有量が１０質量％以上４５質量％以下、
油脂Ｃの含有量が１５質量％以上４０質量％以下である、前記製造方法である。
油脂Ａ：ラウリン系油脂
油脂Ｂ：パーム系油脂
油脂Ｃ：構成脂肪酸中のオレイン酸及びリノール酸の合計含有量が６５質量％以上９５質量％以下の食用油脂 The first invention of the present application is a step of obtaining an extremely hardened fat and oil of fat and oil A, an extremely hardened fat and oil of fat and oil B, and a mixed fat and oil containing fat and oil C.
Including the transesterification step of the mixed fat and oil,
A method for producing transesterified fats and oils.
The content of the extremely hardened fat A in the mixed fat is 35% by mass or more and 70% by mass or less.
The content of the extremely hardened fat / oil B is 10% by mass or more and 45% by mass or less.
This is the production method, wherein the content of fats and oils C is 15% by mass or more and 40% by mass or less.
Fats and oils A: Lauric acid-based fats and oils B: Palm-based fats and oils C: Edible fats and oils having a total content of oleic acid and linoleic acid in the constituent fatty acids of 65% by mass or more and 95% by mass or less.
前記油脂Ａはラウリン系油脂であり、例えば、パーム核油、ヤシ油、及びこれらに分別、水素添加、エステル交換などの加工処理がなされた加工油脂からなる群から選ばれる１種または２種以上のラウリン系油脂であってよい。前記油脂Ａは、パーム核油、ヤシ油、パーム核分別油、ヤシ分別油からなる群から選ばれる１種または２種以上が好ましく、パーム核油、ヤシ油からなる群から選ばれる１種または２種がより好ましく、パーム核油がさらに好ましい。
The fat and oil A is a lauric-based fat and oil, and is one or more selected from the group consisting of, for example, palm kernel oil, coconut oil, and processed fats and oils which have been subjected to processing such as fractionation, hydrogenation, and transesterification. It may be a lauric oil or fat. The fat A is preferably one or more selected from the group consisting of palm kernel oil, coconut oil, palm kernel fractionated oil, and palm fractionated oil, and one or more selected from the group consisting of palm kernel oil and coconut oil. Two are more preferred, and palm kernel oil is even more preferred.
油脂Ａの前記極度硬化油脂は、常法によって油脂Ａを水素添加することによって得ることができる。例えば、ニッケルや白金などの金属触媒を用いて、ヨウ素価が実質的に０になるまで水素添加する方法が挙げられる。
The extremely hardened fat and oil A can be obtained by hydrogenating the fat and oil A by a conventional method. For example, a method of hydrogenating until the iodine value becomes substantially 0 using a metal catalyst such as nickel or platinum can be mentioned.
前記油脂Ｂはパーム系油脂であり、例えば、パーム油及びこれに分別、水素添加、エステル交換などの加工処理がなされた加工油脂からなる群から選ばれる１種または２種以上のパーム系油脂であってよい。前記油脂Ｂは、パーム油、パーム分別油からなる群から選ばれる１種または２種が好ましく、パーム油がより好ましい。
The fats and oils B are palm-based fats and oils, and are, for example, one or more palm-based fats and oils selected from the group consisting of palm oils and processed fats and oils that have been subjected to processing such as separation, hydrogenation, and transesterification. It may be there. The oil / fat B is preferably one or two selected from the group consisting of palm oil and palm fractionated oil, and more preferably palm oil.
油脂Ｂの前記極度硬化油脂は、油脂Ａの前記極度硬化油脂と同じ方法で得ることができる。
The extremely hardened fat and oil of fat and oil B can be obtained by the same method as the extremely hardened fat and oil of fat and oil A.
前記油脂Ｃは、その構成脂肪酸中のオレイン酸及びリノール酸の合計含有量が６５質量％以上９５質量％以下の食用油脂である。前記油脂Ｃの構成脂肪酸中のオレイン酸及びリノール酸の合計含有量は、７０質量％以上９０質量％以下であることが好ましく、７５質量％以上８５質量％以下であることがより好ましい。また、前記油脂Ｃ中の構成脂肪酸中のリノール酸含有量は、３０質量％以上８０質量％以下であることが好ましく、３０質量％以上７０質量％以下であることがより好ましく、４０質量％以上６０質量％以下であることがさらに好ましい。上記の範囲にあることで、得られるエステル交換油脂を付着させた食品のサクサクした食感を向上させることができる。構成脂肪酸中のオレイン酸及びリノール酸の含有量は、基準油脂分析試験法の２．４．２．３－２０１３に従って測定することができる。
The fat and oil C is an edible fat and oil in which the total content of oleic acid and linoleic acid in its constituent fatty acids is 65% by mass or more and 95% by mass or less. The total content of oleic acid and linoleic acid in the constituent fatty acids of the fat and oil C is preferably 70% by mass or more and 90% by mass or less, and more preferably 75% by mass or more and 85% by mass or less. The linoleic acid content in the constituent fatty acids in the fat C is preferably 30% by mass or more and 80% by mass or less, more preferably 30% by mass or more and 70% by mass or less, and 40% by mass or more. It is more preferably 60% by mass or less. Within the above range, the crispy texture of the food to which the obtained transesterified oil and fat is attached can be improved. The contents of oleic acid and linoleic acid in the constituent fatty acids can be measured according to the standard fat analysis test method 2.4.2.3-2013.
前記油脂Ｃとしては、その構成脂肪酸中のオレイン酸及びリノール酸の合計含有量が６５質量％以上９５質量％以下であれば、いずれの原料油脂を用いてもよい。例えば、大豆油、菜種油、綿実油、コーン油、米油、落花生油、ひまわり油、紅花油、ごま油、オリーブ油等の１種または２種以上を含むものであってよく、大豆油、綿実油、コーン油、米油、落花生油、ひまわり油、ハイリノール紅花油、ごま油の１種または２種以上を含むことが好ましく、大豆油、コーン油、米油の１種または２種以上を含むことがより好ましく、コーン油を含むことがさらに好ましく、コーン油がさらにより好ましい。上記の原料油脂を選択することで、得られるエステル交換油脂を付着させた食品のサクサクした食感を向上させることができるとともに、食品の風味を向上させることができる。
As the fat and oil C, any raw material fat or oil may be used as long as the total content of oleic acid and linoleic acid in the constituent fatty acids is 65% by mass or more and 95% by mass or less. For example, it may contain one or more of soybean oil, rapeseed oil, cotton seed oil, corn oil, rice oil, peanut oil, sunflower oil, safflower oil, sesame oil, olive oil, etc., and may contain soybean oil, cotton seed oil, corn oil, etc. , Rice oil, peanut oil, sunflower oil, hylinol safflower oil, sesame oil, preferably one or more, and more preferably soybean oil, corn oil, rice oil, one or more. , Corn oil is even more preferred, and corn oil is even more preferred. By selecting the above-mentioned raw material fats and oils, the crispy texture of the food to which the obtained transesterified fats and oils are attached can be improved, and the flavor of the food can be improved.
前記混合油脂は、油脂Ａの前記極度硬化油脂、油脂Ｂの前記極度硬化油脂及び前記油脂Ｃを含む。前記混合油脂は、油脂Ａの前記極度硬化油脂、油脂Ｂの前記極度硬化油脂及び前記油脂Ｃからなることが好ましい。前記混合油脂を得る前記工程は、油脂Ａの前記極度硬化油脂、油脂Ｂの前記極度硬化油脂及び前記油脂Ｃのうち、任意の２種の油脂をエステル交換してから、もう１種の油脂を混合する工程を含んでいてもよい。
The mixed fat and oil includes the extremely hardened fat and oil of fat and oil A, the extremely hardened fat and oil of fat and oil B, and the fat and oil C. The mixed fat and oil is preferably composed of the extremely hardened fat and oil of fat and oil A, the extremely hardened fat and oil of fat and oil B, and the fat and oil C. In the step of obtaining the mixed fat and oil, any two kinds of fats and oils of the extremely hardened fats and oils A, the extremely hardened fats and oils B, and the fats and oils C are transesterified, and then another fat and oil is transesterified. It may include a step of mixing.
前記混合油脂中の油脂Ａの前記極度硬化油脂の含有量は、３５質量％以上７０質量％以下であり、３７質量％以上７０質量％以下であることが好ましく、４０質量％以上６０質量％以下であることがより好ましく、４０質量％以上５０質量％以下であることがさらに好ましい。前記混合油脂中の油脂Ａの前記極度硬化油脂の含有量が上記の範囲にあることで、得られるエステル交換油脂を付着させた食品のサクサク感を向上させることができる。
The content of the extremely hardened fat A in the mixed fat is 35% by mass or more and 70% by mass or less, preferably 37% by mass or more and 70% by mass or less, and 40% by mass or more and 60% by mass or less. It is more preferable that it is 40% by mass or more and 50% by mass or less. When the content of the extremely hardened fat and oil in the fat and oil A in the mixed fat and oil is within the above range, the crispy feeling of the food to which the obtained transesterified fat and oil is attached can be improved.
前記混合油脂中の油脂Ｂの前記極度硬化油脂の含有量は、１０質量％以上４５質量％以下であり、１０質量％以上４３質量％以下であることが好ましく、２０質量％以上４０質量％以下であることがより好ましく、３０質量％以上４０質量％以下であることがさらに好ましい。前記混合油脂中の油脂Ｂの前記極度硬化油脂の含有量が上記の範囲にあることで、得られるエステル交換油脂を付着させた食品のサクサク感を向上させることができる。
The content of the extremely hardened fat and oil in the fat and oil B in the mixed fat and oil is 10% by mass or more and 45% by mass or less, preferably 10% by mass or more and 43% by mass or less, and 20% by mass or more and 40% by mass or less. It is more preferable that it is 30% by mass or more and 40% by mass or less. When the content of the extremely hardened fat and oil in the fat and oil B in the mixed fat and oil is in the above range, the crispy feeling of the food to which the obtained transesterified fat and oil is attached can be improved.
前記混合油脂中の油脂Ｃの含有量は、１５質量％以上４０質量％以下であり、１８質量％以上３７質量％以下であることが好ましく、２０質量％以上３５質量％以下であることがより好ましい。前記混合油脂中の油脂Ｃの含有量が上記の範囲にあることで、得られるエステル交換油脂を食品に付着させた際に、油っぽさを感じさせにくく、該エステル交換油脂を付着させた食品のサクサク感を向上させることができる。
The content of fats and oils C in the mixed fats and oils is preferably 15% by mass or more and 40% by mass or less, preferably 18% by mass or more and 37% by mass or less, and more preferably 20% by mass or more and 35% by mass or less. preferable. When the content of the oil and fat C in the mixed oil and fat is within the above range, when the obtained transesterified oil and fat is attached to the food, it is difficult to feel the oiliness, and the transesterified oil and fat is attached. The crispness of food can be improved.
前記エステル交換工程は、非選択的エステル交換工程でも、位置特異的エステル交換工程でもよいが、非選択的エステル交換工程が好ましい。非選択的エステル交換工程に使用する触媒としては、ナトリウムメトキシド、ナトリウムエトキシド、水酸化ナトリウム等の化学触媒；Ｌｉｐｏｚｙｍｅ（登録商標） ＴＬ ＩＭ等の酵素触媒が挙げられる。
The transesterification step may be a non-selective transesterification step or a position-specific transesterification step, but a non-selective transesterification step is preferable. Examples of the catalyst used in the non-selective transesterification step include chemical catalysts such as sodium methoxide, sodium ethoxide, and sodium hydroxide; and enzyme catalysts such as Lipozyme (registered trademark) TL IM.
本願の第二の発明は、油脂Ａと油脂Ｂからなる油脂Ｘを準備する工程と、
油脂Ｘを準備する前記工程後の油脂を極度硬化する工程と、
極度硬化する前記工程後の油脂と油脂Ｃとを含む混合油脂を得る工程と、
前記混合油脂のエステル交換工程と、を含む、
エステル交換油脂の製造方法である。 The second invention of the present application is a step of preparing a fat X composed of a fat A and a fat B, and
The step of extremely curing the fat and oil after the step of preparing the fat and oil X, and
A step of obtaining a mixed fat and oil containing the fat and oil and the fat and oil C after the step of being extremely cured, and
Including the transesterification step of the mixed fat and oil,
This is a method for producing transesterified fats and oils.
油脂Ｘを準備する前記工程後の油脂を極度硬化する工程と、
極度硬化する前記工程後の油脂と油脂Ｃとを含む混合油脂を得る工程と、
前記混合油脂のエステル交換工程と、を含む、
エステル交換油脂の製造方法である。 The second invention of the present application is a step of preparing a fat X composed of a fat A and a fat B, and
The step of extremely curing the fat and oil after the step of preparing the fat and oil X, and
A step of obtaining a mixed fat and oil containing the fat and oil and the fat and oil C after the step of being extremely cured, and
Including the transesterification step of the mixed fat and oil,
This is a method for producing transesterified fats and oils.
本願の第二の発明における前記油脂Ａ、前記油脂Ｂ、前記油脂Ｃ及び前記エステル交換工程については、本願の第一の発明に記載した通りである。
The fat A, the fat B, the fat C, and the transesterification step in the second invention of the present application are as described in the first invention of the present application.
極度硬化する前記工程においては、前記油脂Ｘをエステル交換処理する工程を含んでいてもよい。
The step of extremely curing may include a step of transesterifying the fat and oil X.
前記油脂Ｘ中の前記油脂Ａの含有量は、４０質量％以上８８質量％以下であり、４３質量％以上８０質量％以下であることが好ましく、４６質量％以上７０質量％以下であることがより好ましく、５０質量％以上６５質量％以下であることがさらに好ましい。また、前記油脂Ｘ中の前記油脂Ｂの含有量は、１２質量％以上６０質量％以下であり、２０質量％以上５７質量％以下であることが好ましく、３０質量％以上５４質量％以下であることがより好ましく、３５質量％以上５０質量％以下であることがさらに好ましい。
The content of the fat A in the fat X is 40% by mass or more and 88% by mass or less, preferably 43% by mass or more and 80% by mass or less, and 46% by mass or more and 70% by mass or less. More preferably, it is 50% by mass or more and 65% by mass or less. The content of the fat and oil B in the fat and oil X is 12% by mass or more and 60% by mass or less, preferably 20% by mass or more and 57% by mass or less, and 30% by mass or more and 54% by mass or less. More preferably, it is more preferably 35% by mass or more and 50% by mass or less.
前記混合油脂は極度硬化する前記工程後の油脂と前記油脂Ｃとを含むが、極度硬化する前記工程後の油脂と前記油脂Ｃとからなることが好ましい。前記混合油脂中の極度硬化する前記工程後の油脂の含有量は、６０質量％以上８５質量％以下であり、６５質量％以上８５質量％以下であることが好ましい。前記混合油脂中の極度硬化する前記工程後の油脂の含有量が上記の範囲にあることで、得られるエステル交換油脂を付着させた食品のサクサク感を向上させることができる。
The mixed fat and oil contains the fat and oil after the step of being extremely hardened and the fat and oil C, and is preferably composed of the fat and oil after the step of being extremely hardened and the fat and oil C. The content of the fats and oils after the step of being extremely cured in the mixed fats and oils is 60% by mass or more and 85% by mass or less, and preferably 65% by mass or more and 85% by mass or less. When the content of the fats and oils after the step of extremely hardening in the mixed fats and oils is in the above range, the crispy feeling of the food to which the obtained transesterified fats and oils are attached can be improved.
前記混合油脂中の前記油脂Ｃの含有量は、１５質量％以上４０質量％以下であり、１５質量％以上３５質量％以下であることが好ましい。前記混合油脂中の油脂Ｃの含有量が上記の範囲にあることで、得られるエステル交換油脂を食品に付着させた際に、油っぽさを感じさせにくく、該エステル交換油脂を付着させた食品のサクサク感を向上させることができる。
The content of the fat and oil C in the mixed fat and oil is preferably 15% by mass or more and 40% by mass or less, and preferably 15% by mass or more and 35% by mass or less. When the content of the oil and fat C in the mixed oil and fat is within the above range, when the obtained transesterified oil and fat is attached to the food, it is difficult to feel the oiliness, and the transesterified oil and fat is attached. The crispness of food can be improved.
本発明の製造方法で得られたエステル交換油脂は、サクサクした食感が好まれる食品に好適に用いられる。そのような食品としては、クルトン、ラスク、ビスコッティ、揚げ物、米菓、クッキー、ビスケット等が挙げられる。前記エステル交換油脂を前記食品に含有させる手段は問わないが、含浸、塗布、噴霧、滴下、油ちょう等の付着させる手段が好ましい。前記エステル交換油脂を付着させた食品は、油っぽさを感じにくく、サクサク感が向上する。
The transesterified fats and oils obtained by the production method of the present invention are suitably used for foods in which a crispy texture is preferred. Examples of such foods include croutons, rusks, biscotti, fried foods, rice crackers, cookies, biscuits and the like. The means for incorporating the transesterified oil and fat into the food product is not limited, but means for impregnating, coating, spraying, dropping, oiling and the like are preferable. The food to which the transesterified oil and fat is attached is less likely to feel oily and the crispy feeling is improved.
本発明の製造方法で得られたエステル交換油脂は、他の食用油脂、食用油脂以外の食材、食品添加物等と混合した食用油脂組成物として使用することもできる。前記食用油脂組成物は、例えば、フライ油、マーガリンやショートニングとして用いることができる。
The transesterified fats and oils obtained by the production method of the present invention can also be used as an edible fats and oils composition mixed with other edible fats and oils, foodstuffs other than edible fats and oils, food additives and the like. The edible oil / fat composition can be used as, for example, frying oil, margarine or shortening.
以下、実施例および比較例を挙げて、本発明をさらに詳細に説明する。しかし、以下の実施例は、本発明を限定するものではない。
Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples. However, the following examples do not limit the present invention.
（原料油脂）
エステル交換油脂の製造および評価に際して、以下の原料油脂を使用した。なお、原料油脂の構成脂肪酸中のオレイン酸及びリノール酸の含有量は、基準油脂分析試験法の２．４．２．３－２０１３に従って測定した。
コーン油（オレイン酸含有量：３９質量％、リノール酸含有量：５７質量％、株式会社Ｊ－オイルミルズ製）
パーム油（オレイン酸含有量：３９質量％、リノール酸含有量：９質量％、株式会社Ｊ－オイルミルズ製）
パーム核油（オレイン酸含有量：１４質量％、リノール酸含有量：２質量％、株式会社Ｊ－オイルミルズ製）
パーム極度硬化油（横関油脂工業株式会社製）
パーム核極度硬化油（株式会社Ｊ－オイルミルズの社内調製品） (Raw material fats and oils)
The following raw material fats and oils were used in the production and evaluation of transesterified fats and oils. The contents of oleic acid and linoleic acid in the constituent fatty acids of the raw material fats and oils were measured according to 2.4.2.3-2013 of the standard fats and oils analysis test method.
Corn oil (oleic acid content: 39% by mass, linoleic acid content: 57% by mass, manufactured by J-Oil Mills Co., Ltd.)
Palm oil (oleic acid content: 39% by mass, linoleic acid content: 9% by mass, manufactured by J-Oil Mills Co., Ltd.)
Palm kernel oil (oleic acid content: 14% by mass, linoleic acid content: 2% by mass, manufactured by J-Oil Mills Co., Ltd.)
Palm extremely hydrogenated oil (manufactured by Yokoseki Yushi Kogyo Co., Ltd.)
Palm kernel extremely hardened oil (in-house preparation of J-Oil Mills Co., Ltd.)
エステル交換油脂の製造および評価に際して、以下の原料油脂を使用した。なお、原料油脂の構成脂肪酸中のオレイン酸及びリノール酸の含有量は、基準油脂分析試験法の２．４．２．３－２０１３に従って測定した。
コーン油（オレイン酸含有量：３９質量％、リノール酸含有量：５７質量％、株式会社Ｊ－オイルミルズ製）
パーム油（オレイン酸含有量：３９質量％、リノール酸含有量：９質量％、株式会社Ｊ－オイルミルズ製）
パーム核油（オレイン酸含有量：１４質量％、リノール酸含有量：２質量％、株式会社Ｊ－オイルミルズ製）
パーム極度硬化油（横関油脂工業株式会社製）
パーム核極度硬化油（株式会社Ｊ－オイルミルズの社内調製品） (Raw material fats and oils)
The following raw material fats and oils were used in the production and evaluation of transesterified fats and oils. The contents of oleic acid and linoleic acid in the constituent fatty acids of the raw material fats and oils were measured according to 2.4.2.3-2013 of the standard fats and oils analysis test method.
Corn oil (oleic acid content: 39% by mass, linoleic acid content: 57% by mass, manufactured by J-Oil Mills Co., Ltd.)
Palm oil (oleic acid content: 39% by mass, linoleic acid content: 9% by mass, manufactured by J-Oil Mills Co., Ltd.)
Palm kernel oil (oleic acid content: 14% by mass, linoleic acid content: 2% by mass, manufactured by J-Oil Mills Co., Ltd.)
Palm extremely hydrogenated oil (manufactured by Yokoseki Yushi Kogyo Co., Ltd.)
Palm kernel extremely hardened oil (in-house preparation of J-Oil Mills Co., Ltd.)
（エステル交換油脂１の調製）
１００質量部のパーム核油と６０質量部のパーム油とを混合した混合油脂を調製した。前記混合油脂１００質量部に対して、ナトリウムメトキシドを触媒として０．３質量部添加し、８０℃、真空度２．７ｋＰａの条件で６０分間攪拌しながらランダムエステル交換反応をおこなった。ランダムエステル交換反応後、水洗して触媒を除去し、極度硬化油になるまで水素添加をおこなった。水素添加後、活性白土を用いて脱色処理をおこない、さらに脱臭処理をおこない、エステル交換油脂１を得た。 (Preparation of transesterified oil 1)
A mixed fat and oil was prepared by mixing 100 parts by mass of palm kernel oil and 60 parts by mass of palm oil. To 100 parts by mass of the mixed fat and oil, 0.3 part by mass of sodium methoxide was added as a catalyst, and a random transesterification reaction was carried out while stirring at 80 ° C. and a vacuum degree of 2.7 kPa for 60 minutes. After the random transesterification reaction, the catalyst was removed by washing with water, and hydrogenation was performed until the oil became extremely hydrogenated. After hydrogenation, decolorization treatment was performed using activated clay, and further deodorization treatment was performed to obtain transesterified fats and oils 1.
１００質量部のパーム核油と６０質量部のパーム油とを混合した混合油脂を調製した。前記混合油脂１００質量部に対して、ナトリウムメトキシドを触媒として０．３質量部添加し、８０℃、真空度２．７ｋＰａの条件で６０分間攪拌しながらランダムエステル交換反応をおこなった。ランダムエステル交換反応後、水洗して触媒を除去し、極度硬化油になるまで水素添加をおこなった。水素添加後、活性白土を用いて脱色処理をおこない、さらに脱臭処理をおこない、エステル交換油脂１を得た。 (Preparation of transesterified oil 1)
A mixed fat and oil was prepared by mixing 100 parts by mass of palm kernel oil and 60 parts by mass of palm oil. To 100 parts by mass of the mixed fat and oil, 0.3 part by mass of sodium methoxide was added as a catalyst, and a random transesterification reaction was carried out while stirring at 80 ° C. and a vacuum degree of 2.7 kPa for 60 minutes. After the random transesterification reaction, the catalyst was removed by washing with water, and hydrogenation was performed until the oil became extremely hydrogenated. After hydrogenation, decolorization treatment was performed using activated clay, and further deodorization treatment was performed to obtain transesterified fats and oils 1.
（エステル交換油脂２の調製）
８０質量部のエステル交換油脂１と２０質量部のコーン油とを混合した混合油脂を調製した。前記混合油脂１００質量部に対して、ナトリウムメトキシドを触媒として０．３質量部添加し、８０℃、真空度２．７ｋＰａの条件で６０分間攪拌しながらランダムエステル交換反応をおこなった。ランダムエステル交換反応後、水洗して触媒を除去し、活性白土を用いて脱色処理をおこない、さらに脱臭処理をおこない、エステル交換油脂２を得た。 (Preparation of transesterified oil and fat 2)
A mixed fat and oil was prepared by mixing 80 parts by mass of transesterified fat and oil 1 and 20 parts by mass of corn oil. To 100 parts by mass of the mixed fat and oil, 0.3 part by mass of sodium methoxide was added as a catalyst, and a random transesterification reaction was carried out while stirring at 80 ° C. and a vacuum degree of 2.7 kPa for 60 minutes. After the random transesterification reaction, the catalyst was removed by washing with water, decolorization treatment was performed using activated clay, and further deodorization treatment was performed to obtain transesterified fats and oils 2.
８０質量部のエステル交換油脂１と２０質量部のコーン油とを混合した混合油脂を調製した。前記混合油脂１００質量部に対して、ナトリウムメトキシドを触媒として０．３質量部添加し、８０℃、真空度２．７ｋＰａの条件で６０分間攪拌しながらランダムエステル交換反応をおこなった。ランダムエステル交換反応後、水洗して触媒を除去し、活性白土を用いて脱色処理をおこない、さらに脱臭処理をおこない、エステル交換油脂２を得た。 (Preparation of transesterified oil and fat 2)
A mixed fat and oil was prepared by mixing 80 parts by mass of transesterified fat and oil 1 and 20 parts by mass of corn oil. To 100 parts by mass of the mixed fat and oil, 0.3 part by mass of sodium methoxide was added as a catalyst, and a random transesterification reaction was carried out while stirring at 80 ° C. and a vacuum degree of 2.7 kPa for 60 minutes. After the random transesterification reaction, the catalyst was removed by washing with water, decolorization treatment was performed using activated clay, and further deodorization treatment was performed to obtain transesterified fats and oils 2.
（エステル交換油脂３の調製）
エステル交換油脂２の調製に記載の混合油脂を、８０質量部のエステル交換油脂１と２０質量部のパーム油とを混合した混合油脂に変えた以外はエステル交換油脂２の調製と同じ方法で、エステル交換油脂３を得た。 (Preparation of transesterified oil and fat 3)
The same method as for the preparation of transesterified fat 2 except that the mixed fat described in the preparation of transesterified fat 2 was changed to a mixed fat obtained by mixing 80 parts by mass of transesterified fat 1 and 20 parts by mass of palm oil. A transesterified oil and fat 3 was obtained.
エステル交換油脂２の調製に記載の混合油脂を、８０質量部のエステル交換油脂１と２０質量部のパーム油とを混合した混合油脂に変えた以外はエステル交換油脂２の調製と同じ方法で、エステル交換油脂３を得た。 (Preparation of transesterified oil and fat 3)
The same method as for the preparation of transesterified fat 2 except that the mixed fat described in the preparation of transesterified fat 2 was changed to a mixed fat obtained by mixing 80 parts by mass of transesterified fat 1 and 20 parts by mass of palm oil. A transesterified oil and fat 3 was obtained.
（エステル交換油脂４の調製）
エステル交換油脂２の調製に記載の混合油脂を、４０質量部のパーム極度硬化油と４０質量部のパーム核極度硬化油、２０質量部のコーン油とを混合した混合油脂に変えた以外はエステル交換油脂２の調製と同じ方法で、エステル交換油脂４を得た。 (Preparation of transesterified fat 4)
Esters except that the mixed fats and oils described in the preparation of transesterified fats and oils 2 were changed to mixed fats and oils obtained by mixing 40 parts by mass of palm core extremely hardened oil, 40 parts by mass of palm nucleus extremely hardened oil, and 20 parts by mass of corn oil. The transesterified oil 4 was obtained in the same manner as in the preparation of the transesterified oil 2.
エステル交換油脂２の調製に記載の混合油脂を、４０質量部のパーム極度硬化油と４０質量部のパーム核極度硬化油、２０質量部のコーン油とを混合した混合油脂に変えた以外はエステル交換油脂２の調製と同じ方法で、エステル交換油脂４を得た。 (Preparation of transesterified fat 4)
Esters except that the mixed fats and oils described in the preparation of transesterified fats and oils 2 were changed to mixed fats and oils obtained by mixing 40 parts by mass of palm core extremely hardened oil, 40 parts by mass of palm nucleus extremely hardened oil, and 20 parts by mass of corn oil. The transesterified oil 4 was obtained in the same manner as in the preparation of the transesterified oil 2.
（クルトンによる評価）
表１に記載の油脂を６０℃に加温して溶解させた。溶解した油脂に予め質量（Ｍ１）を測定したクルトン（製品名：ＨＡＮＤＰＡＣＫこんがりクルトンプレーン味、ノンフライクルトン、日本製粉株式会社製）を漬けて、クルトンに油脂を含浸させた後、遠心管に入れて、１０００ｒｐｍ、４分の条件で遠心分離した。遠心管からクルトンを取り出し、油脂含浸後のクルトンの質量（Ｍ２）を測定した。油脂含浸後のクルトンは、チャック付きポリ袋に入れて、２０℃で２４時間保管してから、専門パネラー３名が食し、風味、サクサク感、油っぽさについて下記の評価基準により、合議の上評価した。評価結果は表１に記載した。 (Evaluation by croutons)
The fats and oils listed in Table 1 were heated to 60 ° C. to dissolve them. Soak croutons (product name: HANDPACK brown crouton plain taste, non-fried croutons, manufactured by Nippon Flour Mills Co., Ltd.) whose mass (M1) has been measured in advance in the melted fats and oils, impregnate the croutons with fats and oils, and then put them in a centrifuge tube. Centrifugation was carried out under the conditions of 1000 rpm and 4 minutes. The croutons were taken out from the centrifuge tube, and the mass (M2) of the croutons after impregnation with oil and fat was measured. After impregnating the oil and fat, the croutons are placed in a plastic bag with a chuck and stored at 20 ° C for 24 hours, and then eaten by three specialized panelists. The flavor, crispness, and oiliness are discussed according to the following evaluation criteria. I evaluated it above. The evaluation results are shown in Table 1.
表１に記載の油脂を６０℃に加温して溶解させた。溶解した油脂に予め質量（Ｍ１）を測定したクルトン（製品名：ＨＡＮＤＰＡＣＫこんがりクルトンプレーン味、ノンフライクルトン、日本製粉株式会社製）を漬けて、クルトンに油脂を含浸させた後、遠心管に入れて、１０００ｒｐｍ、４分の条件で遠心分離した。遠心管からクルトンを取り出し、油脂含浸後のクルトンの質量（Ｍ２）を測定した。油脂含浸後のクルトンは、チャック付きポリ袋に入れて、２０℃で２４時間保管してから、専門パネラー３名が食し、風味、サクサク感、油っぽさについて下記の評価基準により、合議の上評価した。評価結果は表１に記載した。 (Evaluation by croutons)
The fats and oils listed in Table 1 were heated to 60 ° C. to dissolve them. Soak croutons (product name: HANDPACK brown crouton plain taste, non-fried croutons, manufactured by Nippon Flour Mills Co., Ltd.) whose mass (M1) has been measured in advance in the melted fats and oils, impregnate the croutons with fats and oils, and then put them in a centrifuge tube. Centrifugation was carried out under the conditions of 1000 rpm and 4 minutes. The croutons were taken out from the centrifuge tube, and the mass (M2) of the croutons after impregnation with oil and fat was measured. After impregnating the oil and fat, the croutons are placed in a plastic bag with a chuck and stored at 20 ° C for 24 hours, and then eaten by three specialized panelists. The flavor, crispness, and oiliness are discussed according to the following evaluation criteria. I evaluated it above. The evaluation results are shown in Table 1.
（吸油量の計算）
吸油量は下記式により計算して求めた。求めた吸油量は表１に記載した。
吸油量（質量％）＝（Ｍ２－Ｍ１）／Ｍ１×１００ (Calculation of oil absorption)
The oil absorption amount was calculated by the following formula. The obtained oil absorption is shown in Table 1.
Oil absorption (mass%) = (M2-M1) / M1 × 100
吸油量は下記式により計算して求めた。求めた吸油量は表１に記載した。
吸油量（質量％）＝（Ｍ２－Ｍ１）／Ｍ１×１００ (Calculation of oil absorption)
The oil absorption amount was calculated by the following formula. The obtained oil absorption is shown in Table 1.
Oil absorption (mass%) = (M2-M1) / M1 × 100
（風味の評価基準）
５：油脂含浸前のクルトンよりも風味がとてもよい
４：油脂含浸前のクルトンよりも風味がよい
３：油脂含浸前のクルトンよりも風味がややよい
２：油脂含浸前のクルトンと風味が変わらない
１：油脂含浸前のクルトンよりも風味が悪い
ここで風味がよいとは、咀嚼中に香ばしい香りが感じられることを意味する。 (Flavor evaluation criteria)
5: Very good flavor than croutons before oil impregnation 4: Better flavor than croutons before oil impregnation 3: Slightly flavored than croutons before oil impregnation 2: Flavor is the same as croutons before oil impregnation 1: Poor flavor than croutons before oil impregnation Here, good flavor means that a fragrant aroma is felt during chewing.
５：油脂含浸前のクルトンよりも風味がとてもよい
４：油脂含浸前のクルトンよりも風味がよい
３：油脂含浸前のクルトンよりも風味がややよい
２：油脂含浸前のクルトンと風味が変わらない
１：油脂含浸前のクルトンよりも風味が悪い
ここで風味がよいとは、咀嚼中に香ばしい香りが感じられることを意味する。 (Flavor evaluation criteria)
5: Very good flavor than croutons before oil impregnation 4: Better flavor than croutons before oil impregnation 3: Slightly flavored than croutons before oil impregnation 2: Flavor is the same as croutons before oil impregnation 1: Poor flavor than croutons before oil impregnation Here, good flavor means that a fragrant aroma is felt during chewing.
（サクサク感の評価基準）
５：油脂含浸前のクルトンよりもとてもサクサクしている
４：油脂含浸前のクルトンよりもサクサクしている
３：油脂含浸前のクルトンよりもややサクサクしている
２：油脂含浸前のクルトンよりもやや硬くあまりサクサク感を感じない
１：油脂含浸前のクルトンよりも硬くサクサク感を感じない (Evaluation criteria for crispness)
5: Very crispy than the croutons before oil impregnation 4: Crispy than the croutons before oil impregnation 3: Slightly crisper than the croutons before oil impregnation 2: Than the croutons before oil impregnation Slightly hard and does not feel crispy 1: Harder and less crispy than croutons before oil impregnation
５：油脂含浸前のクルトンよりもとてもサクサクしている
４：油脂含浸前のクルトンよりもサクサクしている
３：油脂含浸前のクルトンよりもややサクサクしている
２：油脂含浸前のクルトンよりもやや硬くあまりサクサク感を感じない
１：油脂含浸前のクルトンよりも硬くサクサク感を感じない (Evaluation criteria for crispness)
5: Very crispy than the croutons before oil impregnation 4: Crispy than the croutons before oil impregnation 3: Slightly crisper than the croutons before oil impregnation 2: Than the croutons before oil impregnation Slightly hard and does not feel crispy 1: Harder and less crispy than croutons before oil impregnation
（油っぽさの評価基準）
５：全く油っぽさを感じない
４：ほとんど油っぽさを感じない
３：あまり油っぽさを感じない
２：やや油っぽい
１：油っぽい (Evaluation criteria for oiliness)
5: I don't feel oily at all 4: I don't feel oily at all 3: I don't feel much oily 2: Slightly oily 1: Oily
５：全く油っぽさを感じない
４：ほとんど油っぽさを感じない
３：あまり油っぽさを感じない
２：やや油っぽい
１：油っぽい (Evaluation criteria for oiliness)
5: I don't feel oily at all 4: I don't feel oily at all 3: I don't feel much oily 2: Slightly oily 1: Oily
表１に記載の通り、クルトンの吸油量はいずれも約２３質量％であり、吸油量に大きな差はなかった。実施例の油脂を含浸させたクルトンは、２４時間経過しても風味がとてもよく、サクサクした食感にも優れていた。更に油っぽさもほとんど感じられなかった。構成脂肪酸中のオレイン酸及びリノール酸の合計含有量が４８質量％のパーム油と極度硬化油とのエステル交換油脂である比較例１及び、エステル交換後に極度硬化した油脂を含浸させた比較例２のクルトンは、ほとんど油っぽさを感じないものの、風味が悪く、硬すぎるため、サクサクした食感に劣っていた。エステル交換後に極度硬化した油脂とコーン油とを混合した油脂を含浸させた比較例３のクルトンは、風味がよく、サクサクした食感であったが、油っぽさがやや感じられた。
As shown in Table 1, the oil absorption of croutons was about 23% by mass, and there was no significant difference in the oil absorption. The croutons impregnated with the fats and oils of the examples had a very good flavor even after 24 hours, and had an excellent crispy texture. Furthermore, I could hardly feel the oiliness. Comparative Example 1 in which the total content of oleic acid and linoleic acid in the constituent fatty acids is 48% by mass, which is a transesterified oil and fat of palm oil and extremely hydrogenated oil, and Comparative Example 2 in which an extremely hardened oil and fat are impregnated after the ester exchange. Although the crouton felt almost no oily, it had a bad flavor and was too hard, so it had a poor crispy texture. The croutons of Comparative Example 3 impregnated with fats and oils obtained by mixing extremely hardened fats and oils and corn oil after transesterification had a good flavor and a crispy texture, but were slightly oily.
As shown in Table 1, the oil absorption of croutons was about 23% by mass, and there was no significant difference in the oil absorption. The croutons impregnated with the fats and oils of the examples had a very good flavor even after 24 hours, and had an excellent crispy texture. Furthermore, I could hardly feel the oiliness. Comparative Example 1 in which the total content of oleic acid and linoleic acid in the constituent fatty acids is 48% by mass, which is a transesterified oil and fat of palm oil and extremely hydrogenated oil, and Comparative Example 2 in which an extremely hardened oil and fat are impregnated after the ester exchange. Although the crouton felt almost no oily, it had a bad flavor and was too hard, so it had a poor crispy texture. The croutons of Comparative Example 3 impregnated with fats and oils obtained by mixing extremely hardened fats and oils and corn oil after transesterification had a good flavor and a crispy texture, but were slightly oily.
Claims (6)
- 油脂Ａの極度硬化油脂、油脂Ｂの極度硬化油脂、及び油脂Ｃを含む混合油脂を得る工程と、
前記混合油脂のエステル交換工程と、を含む、
エステル交換油脂の製造方法であって、
前記混合油脂中の
油脂Ａの前記極度硬化油脂の含有量が３５質量％以上７０質量％以下、
油脂Ｂの前記極度硬化油脂の含有量が１０質量％以上４５質量％以下、
前記油脂Ｃの含有量が１５質量％以上４０質量％以下である、前記製造方法。
油脂Ａ：ラウリン系油脂
油脂Ｂ：パーム系油脂
油脂Ｃ：構成脂肪酸中のオレイン酸及びリノール酸の合計含有量が６５質量％以上９５質量％以下の食用油脂 A step of obtaining an extremely hardened fat and oil of fat and oil A, an extremely hardened fat and oil of fat and oil B, and a mixed fat and oil containing fat and oil C.
Including the transesterification step of the mixed fat and oil,
A method for producing transesterified fats and oils.
The content of the extremely hardened fat A in the mixed fat is 35% by mass or more and 70% by mass or less.
The content of the extremely hardened fat / oil B is 10% by mass or more and 45% by mass or less.
The production method, wherein the content of the fat and oil C is 15% by mass or more and 40% by mass or less.
Fats and oils A: Lauric acid-based fats and oils B: Palm-based fats and oils C: Edible fats and oils having a total content of oleic acid and linoleic acid in the constituent fatty acids of 65% by mass or more and 95% by mass or less. - 油脂Ａと油脂Ｂからなる油脂Ｘを準備する工程と、
油脂Ｘを準備する前記工程後の油脂を極度硬化する工程と、
極度硬化する前記工程後の油脂と油脂Ｃとを含む混合油脂を得る工程と、
前記混合油脂のエステル交換工程と、を含む、
エステル交換油脂の製造方法であって、
前記油脂Ｘ中の
前記油脂Ａの含有量が４０質量％以上８８質量％以下、
前記油脂Ｂの含有量が１２質量％以上６０質量％以下であり、
前記混合油脂中の
極度硬化する前記工程後の油脂の含有量が６０質量％以上８５質量％以下、
前記油脂Ｃの含有量が１５質量％以上４０質量％以下である、前記製造方法。
油脂Ａ：ラウリン系油脂
油脂Ｂ：パーム系油脂
油脂Ｃ：構成脂肪酸中のオレイン酸及びリノール酸の合計含有量が６５質量％以上９５質量％以下の食用油脂 The process of preparing the fat and oil X composed of the fat and oil A and the fat and oil B,
The step of extremely curing the fat and oil after the step of preparing the fat and oil X, and
A step of obtaining a mixed fat and oil containing the fat and oil and the fat and oil C after the step of being extremely cured, and
Including the transesterification step of the mixed fat and oil,
A method for producing transesterified fats and oils.
The content of the fat A in the fat X is 40% by mass or more and 88% by mass or less.
The content of the fat and oil B is 12% by mass or more and 60% by mass or less.
The content of the fats and oils after the step of being extremely hardened in the mixed fats and oils is 60% by mass or more and 85% by mass or less.
The production method, wherein the content of the fat and oil C is 15% by mass or more and 40% by mass or less.
Fats and oils A: Lauric acid-based fats and oils B: Palm-based fats and oils C: Edible fats and oils having a total content of oleic acid and linoleic acid in the constituent fatty acids of 65% by mass or more and 95% by mass or less. - 前記油脂Ｃの構成脂肪酸中のリノール酸含有量が３０質量％以上８０質量％以下である、請求項１または２に記載の製造方法。 The production method according to claim 1 or 2, wherein the content of linoleic acid in the constituent fatty acids of the fat C is 30% by mass or more and 80% by mass or less.
- 前記油脂Ｃがコーン油、大豆油及び米油からなる群から選択される１種または２種以上を含む、請求項１乃至３のいずれか１項に記載のエステル交換油脂の製造方法。 The method for producing a transesterified fat or oil according to any one of claims 1 to 3, wherein the fat or oil C contains one or more selected from the group consisting of corn oil, soybean oil and rice oil.
- 前記エステル交換工程が非選択的エステル交換工程である、請求項１乃至４いずれか１項に記載の製造方法。 The production method according to any one of claims 1 to 4, wherein the transesterification step is a non-selective transesterification step.
- 請求項１乃至５に記載の製造方法で得られたエステル交換油脂を含む食品の製造方法。
A method for producing a food product containing a transesterified oil or fat obtained by the production method according to any one of claims 1 to 5.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2019052028A JP2022076026A (en) | 2019-03-20 | 2019-03-20 | Method for producing transesterified fat |
| JP2019-052028 | 2019-03-20 |
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| Publication Number | Publication Date |
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| WO2020189382A1 true WO2020189382A1 (en) | 2020-09-24 |
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| Application Number | Title | Priority Date | Filing Date |
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| PCT/JP2020/010068 WO2020189382A1 (en) | 2019-03-20 | 2020-03-09 | Method for manufacturing transesterified oil/fat |
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| Country | Link |
|---|---|
| JP (1) | JP2022076026A (en) |
| TW (1) | TW202041659A (en) |
| WO (1) | WO2020189382A1 (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02132191A (en) * | 1988-11-12 | 1990-05-21 | Fuji Oil Co Ltd | Preparation of milk fats-like fats and oils |
| JPH09241672A (en) * | 1996-03-05 | 1997-09-16 | Fuji Oil Co Ltd | Hard stock and production of hard stock-containing plastic oil and fat composition |
| WO2007129590A1 (en) * | 2006-05-01 | 2007-11-15 | Fuji Oil Company, Limited | Oil and fat composition for chocolate |
| WO2017163957A1 (en) * | 2016-03-24 | 2017-09-28 | 不二製油グループ本社株式会社 | Plastic fat and roll-in fat composition using same |
-
2019
- 2019-03-20 JP JP2019052028A patent/JP2022076026A/en active Pending
-
2020
- 2020-03-09 WO PCT/JP2020/010068 patent/WO2020189382A1/en active Application Filing
- 2020-03-11 TW TW109108011A patent/TW202041659A/en unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02132191A (en) * | 1988-11-12 | 1990-05-21 | Fuji Oil Co Ltd | Preparation of milk fats-like fats and oils |
| JPH09241672A (en) * | 1996-03-05 | 1997-09-16 | Fuji Oil Co Ltd | Hard stock and production of hard stock-containing plastic oil and fat composition |
| WO2007129590A1 (en) * | 2006-05-01 | 2007-11-15 | Fuji Oil Company, Limited | Oil and fat composition for chocolate |
| WO2017163957A1 (en) * | 2016-03-24 | 2017-09-28 | 不二製油グループ本社株式会社 | Plastic fat and roll-in fat composition using same |
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| Publication number | Publication date |
|---|---|
| TW202041659A (en) | 2020-11-16 |
| JP2022076026A (en) | 2022-05-19 |
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