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WO2024203587A1 - Plastic oil/fat composition production method and food production method - Google Patents

Plastic oil/fat composition production method and food production method Download PDF

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Publication number
WO2024203587A1
WO2024203587A1 PCT/JP2024/010687 JP2024010687W WO2024203587A1 WO 2024203587 A1 WO2024203587 A1 WO 2024203587A1 JP 2024010687 W JP2024010687 W JP 2024010687W WO 2024203587 A1 WO2024203587 A1 WO 2024203587A1
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WO
WIPO (PCT)
Prior art keywords
fatty acid
mass
acid ester
fatty acids
less
Prior art date
Application number
PCT/JP2024/010687
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French (fr)
Japanese (ja)
Inventor
亮輔 青木
将士 岩崎
穂高 谷津
眞善 境野
実奈 吉村
Original Assignee
株式会社Ｊ－オイルミルズ
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Publication of WO2024203587A1 publication Critical patent/WO2024203587A1/en

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Classifications

    • 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
    • A21D13/80—Pastry not otherwise provided for elsewhere, e.g. cakes, biscuits or cookies
    • 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
    • A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
    • A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
    • A21D2/14—Organic oxygen compounds
    • A21D2/16—Fatty acid esters
    • 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
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines

Definitions

  • the present invention relates to a method for producing a plastic oil composition and a method for producing a food product.
  • Patent documents 1 and 2 are examples of plastic oil compositions.
  • Patent Document 1 describes a plastic oil composition that contains an emulsifier having unsaturated fatty acids with 16 or more carbon atoms in its constituent fatty acids and a diglycerol fatty acid ester having saturated fatty acids with 14 or less carbon atoms in its constituent fatty acids, and has an oil content of 70% by mass or more. It is said that the composition can provide an air-containing foam-like composition that is stable and melts easily in the mouth even when the proportion of aqueous components is high, and a plastic oil composition that serves as the base for the air-containing composition.
  • Patent Document 2 describes a plastic oil composition that contains 70% by mass or more of an oil that is liquid at 20°C, and (A) 5 to 30% by mass of a polyglycerol fatty acid ester, or (B) 3 to 12% by mass of a polyglycerol fatty acid ester and 2 to 10% by mass of an extremely hardened oil and/or wax, and the total of the polyglycerol fatty acid ester and the extremely hardened oil and/or wax is 6% by mass or more, wherein the polyglycerol fatty acid ester contains 90% or more of saturated fatty acids having 16 to 18 carbon atoms out of 100% of the constituent fatty acids, the plastic oil composition contains 40% or less by mass of saturated fatty acids having 16 or more carbon atoms relative to the mass of the total constituent fatty acids of the plastic oil composition, and the difference in the common logarithm of the storage modulus at 10°C and 30°C in dynamic viscoelasticity measurement is less than 1.0. It is described that this plastic oil composition has good plasticity over a wide
  • the present invention provides a method for producing a plastic oil composition that can improve the balance between plasticity and shape retention.
  • the inventors have found that the plasticity and shape retention of a plastic oil composition can be improved by including a glycerin fatty acid ester in the oil composition containing a fatty acid residue having a carbon number of 13 or more and 15 or less, and by controlling the content of fatty acids having a carbon number of 13 or more and 15 or less in the total fatty acids of the glycerin fatty acid ester within a specified range and controlling the mass ratio of the content of fatty acids having a carbon number of 12 to the content of fatty acids having a carbon number of 13 or more and 15 or less within a specified range.
  • the present invention provides the following method for producing a plastic oil composition and method for producing a food product.
  • a method for producing a plastic oil composition comprising a step of mixing a raw material containing an oil composition,
  • the oil and fat composition contains a glycerin fatty acid ester containing a fatty acid residue having a carbon number of 13 to 15,
  • the glycerin fatty acid ester contains 1.8% by mass or more and 100% by mass or less of fatty acids having 13 or more and 15 or less carbon atoms in the total fatty acids of the glycerin fatty acid ester
  • a method for producing a plastic oil composition wherein the content of fatty acids having 12 carbon atoms in the total fatty acids of the glycerin fatty acid ester is in a mass ratio of 0 to 2.5 relative to the content of fatty acids having 13 to 15 carbon atoms.
  • [2] The method for producing a plastic oil composition described in [1], wherein the fatty acid having 13 or more and 15 or less carbon atoms includes one or more selected from the group consisting of tridecanoic acid, tetradecanoic acid, and pentadecanoic acid.
  • [3] A method for producing a plastic oil composition according to [1] or [2], wherein the content of fatty acids having 12 carbon atoms in the total fatty acids of the glycerin fatty acid ester is 0% by mass or more and 15% by mass or less.
  • [4] The method for producing a plastic oil composition according to any one of [1] to [3], wherein the content of fatty acids having 14 carbon atoms in the total fatty acids of the glycerin fatty acid ester is 1.0% by mass or more and 100% by mass or less.
  • [5] The method for producing a plastic oil composition according to any one of [1] to [4], wherein the glycerin fatty acid ester has a saturated fatty acid (SFA) content of 20% by mass or more and 65% by mass or less of the total fatty acids.
  • SFA saturated fatty acid
  • [6] A method for producing a plastic oil composition according to any one of [1] to [5], wherein the polyunsaturated fatty acid (PUFA) content in the total fatty acids of the glycerin fatty acid ester is 5% by mass or more and 45% by mass or less.
  • PUFA polyunsaturated fatty acid
  • the method for producing a plastic oil composition according to [11] further comprises a step of transesterifying the glycerin fatty acid ester obtained by reacting the fatty acid having a carbon number of 13 to 15 and the glycerin with an edible oil containing a glycerin fatty acid ester other than the glycerin fatty acid ester.
  • a method for producing a food product comprising the step of preparing a food product using a raw material containing a plastic oil composition obtained by the method for producing a plastic oil composition according to any one of [1] to [12].
  • a method for improving the flavor of a plastic oil-and-fat composition comprising a step of mixing a raw material containing an oil-and-fat composition,
  • the oil and fat composition contains a glycerin fatty acid ester containing a fatty acid residue having a carbon number of 13 to 15,
  • the glycerin fatty acid ester contains 1.8% by mass or more and 100% by mass or less of fatty acids having 13 or more and 15 or less carbon atoms in the total fatty acids of the glycerin fatty acid ester
  • a method for improving the flavor of a plastic oil composition wherein the content of fatty acids having 12 carbon atoms in the total fatty acids of the glycerin fatty acid ester is in a mass ratio of 0 to 2.5 relative to the content of fatty acids having 13 to 15 carbon atoms.
  • the present invention provides a method for producing a plastic oil composition that can improve the balance between plasticity and shape retention.
  • a to B indicating a numerical range means A or more and B or less, unless otherwise specified.
  • the upper limit and the lower limit can be appropriately combined, and the numerical range obtained by combining them is also considered to be disclosed.
  • the method for producing a plastic oil composition includes a step of mixing raw materials containing an oil composition, and the oil composition contains a glycerin fatty acid ester containing a fatty acid residue having a carbon number of 13 or more and 15 or less, and the total fatty acids in the glycerin fatty acid ester contain fatty acids having a carbon number of 13 or more and 15 or less at 1.8% by mass or more and 100% by mass or less, and the content of fatty acids having a carbon number of 12 in the total fatty acids in the glycerin fatty acid ester is a mass ratio of 0 to 2.5 relative to the content of fatty acids having a carbon number of 13 or more and 15 or less.
  • the glycerin fatty acid ester refers to an ester bond between glycerin and one or more and three or less fatty acids.
  • the glycerin fatty acid ester is preferably an ester bond between glycerin and three fatty acids.
  • the content of fatty acids having a carbon number of 13 or more and 15 or less in the total fatty acids of the glycerin fatty acid ester is 1.8 mass% or more, preferably 3.0 mass% or more, more preferably 5.0 mass% or more, and even more preferably 6.0 mass% or more, and is 100 mass% or less, for example, may be 90 mass% or less, 80 mass% or less, 60 mass% or less, 50 mass% or less, or 40 mass% or less.
  • the mass ratio of the content of fatty acids having 12 carbon atoms to the content of fatty acids having 13 or more and 15 or less carbon atoms in the total fatty acids of the glycerin fatty acid ester is 2.5 or less, preferably 2.3 or less, more preferably 2.1 or less, even more preferably 1.8 or less, even more preferably 1.5 or less, still more preferably 1.0 or less, and is 0 or more.
  • the mass ratio of the content of fatty acids having 12 carbon atoms to the content of fatty acids having 13 or more and 15 or less carbon atoms in the total fatty acids of the glycerin fatty acid ester is 2.50 or less, preferably 2.00 or less, more preferably 1.50 or less, even more preferably 1.00 or less, even more preferably 0.50 or less, even more preferably less than 0.17, even more preferably 0.15 or less, and is 0 or more.
  • the inventors have found that in the method for producing a plastic oil composition of this embodiment, by setting the content of fatty acids having 13 to 15 carbon atoms and the mass ratio of the content of fatty acids having 12 carbon atoms to the content of fatty acids having 13 to 15 carbon atoms within a specified range, the plasticity and shape retention can be improved.
  • the content of fatty acids having 12 carbon atoms in the total fatty acids of the glycerin fatty acid ester is preferably 15% by mass or less, more preferably 14% by mass or less, even more preferably 13% by mass or less, still more preferably 10% by mass or less, and even more preferably 5% by mass or less, from the viewpoint of further improving the balance of plasticity, shape retention, and flavor.
  • the content of fatty acids having 12 carbon atoms in the total fatty acids of the glycerin fatty acid ester is preferably 15% by mass or less, more preferably 10% by mass or less, even more preferably 5% by mass or less, still more preferably 3% by mass or less, even more preferably 2% by mass or less, and even more preferably 1.5% by mass or less, from the viewpoint of further improving the balance of plasticity, shape retention, and flavor.
  • the content of fatty acids having 14 carbon atoms in the total fatty acids of the glycerin fatty acid ester is preferably 1.0% by mass or more, more preferably 2.0% by mass or more, even more preferably 3.0% by mass or more, even more preferably 4.0% by mass or more, and even more preferably 4.5% by mass or more, from the viewpoint of further improving shape retention and blood glucose level lowering function, and is preferably 100% by mass or less, more preferably 90% by mass or less, even more preferably 70% by mass or less, even more preferably 50% by mass or less, and even more preferably 40% by mass or less, from the viewpoint of keeping physical properties such as the melting point in an appropriate range and further improving handleability.
  • the content of unsaturated fatty acids having 18 carbon atoms in the total fatty acids of the glycerin fatty acid ester is preferably 31% by mass or more, more preferably 35% by mass or more, even more preferably 40% by mass or more, even more preferably 45% by mass or more, even more preferably 50% by mass or more, from the viewpoint of further improving the balance of plasticity, shape retention, and flavor, and is also preferably 90% by mass or less, more preferably 85% by mass or less, even more preferably 80% by mass or less, and even more preferably 75% by mass or less.
  • the fatty acid having 13 to 15 carbon atoms preferably includes one or more selected from the group consisting of tridecanoic acid, tetradecanoic acid, and pentadecanoic acid.
  • Tridecanoic acid is a saturated fatty acid having 13 carbon atoms
  • tetradecanoic acid is a saturated fatty acid having 14 carbon atoms
  • pentadecanoic acid is a saturated fatty acid having 15 carbon atoms.
  • Tetradecanoic acid is also found in large amounts in natural fats and oils such as palm kernel oil, coconut oil, and milk fat.
  • the glycerin fatty acid ester preferably contains an interesterified oil, which can further improve the plasticity.
  • the content of the interesterified oil relative to the entire glycerin fatty acid ester is preferably 10% by mass or more, more preferably 20% by mass or more, even more preferably 30% by mass or more, still more preferably 40% by mass or more, and preferably 100% by mass or less.
  • the content of the transesterified oil relative to the total glycerin fatty acid ester is preferably 1 mass% or more, more preferably 3 mass% or more, even more preferably 5 mass% or more, still more preferably 10 mass% or more, even more preferably 15 mass% or more, and preferably 100 mass% or less.
  • the method for producing the interesterified oil will be described later.
  • the glycerin fatty acid ester may contain edible oils and fats other than the interesterified oil.
  • the edible oils and fats are not particularly limited, but examples thereof include vegetable oils and fats such as rapeseed oil, soybean oil, corn oil, sesame oil, coconut oil, palm oil, palm kernel oil, rice oil, cottonseed oil, safflower oil, sunflower oil, olive oil, linseed oil, peanut oil, monkey fat, cacao butter, and shea butter; animal oils and fats such as beef tallow, lard, chicken fat, milk fat, and fish oil; and synthetic oils and fats such as medium-chain fatty acid triglycerides.
  • processed oils and fats obtained by subjecting the above-mentioned oils and fats to treatments such as fractionation and hydrogenation are also included.
  • one or more types selected from the group consisting of vegetable oils and fats and their processed oils and fats are preferred, and one or more types selected from the group consisting of rapeseed oil, soybean oil, palm oil, sunflower oil, and their processed oils and fats are more preferred.
  • the oil may also contain an interesterified oil other than the interesterified oil of a glycerin fatty acid ester containing a fatty acid residue having a carbon number of 13 to 15.
  • the raw material fat of the interesterified oil may be appropriately selected from the edible fats and oils described above.
  • the melting point of the oil composition in the method for producing a plastic oil composition of this embodiment is preferably 80°C or lower, more preferably 70°C or lower, and even more preferably 60°C or lower, from the viewpoint of improving handleability.
  • the iodine value of the oil composition in the method for producing a plastic oil composition of this embodiment is, from the viewpoint of further improving handleability, preferably 60 or more, more preferably 65 or more, and even more preferably 70 or more, and from the viewpoint of further improving the balance between shape retention and storage stability, preferably 110 or less, more preferably 105 or less, even more preferably 100 or less, even more preferably 90 or less, even more preferably 85 or less, and even more preferably 80 or less.
  • the iodine value of the oil composition in the manufacturing method for a plastic oil composition of this embodiment is, from the viewpoint of further improving handleability, preferably 40 or more, more preferably 50 or more, even more preferably 60 or more, and even more preferably 70 or more, and from the viewpoint of further improving the balance between shape retention and storage stability, is preferably 110 or less, more preferably 105 or less, even more preferably 100 or less, even more preferably 90 or less, even more preferably 85 or less, and even more preferably 80 or less.
  • the saturated fatty acid (SFA) content in the total fatty acids of the glycerin fatty acid ester is, from the viewpoint of further improving the balance between plasticity, shape retention and handleability, preferably 20% by mass or more, more preferably 23% by mass or more, even more preferably 25% by mass or more, even more preferably 30% by mass or more, and is preferably 60% by mass or less, more preferably 55% by mass or less, and even more preferably 50% by mass or less.
  • the saturated fatty acid (SFA) content in the total fatty acids of the glycerin fatty acid ester of the oil composition in the manufacturing method for a plastic oil composition of this embodiment is, from the viewpoint of further improving the balance of plasticity, shape retention and handleability, preferably 20 mass% or more, more preferably 23 mass% or more, even more preferably 25 mass% or more, even more preferably 30 mass% or more, and is preferably 65 mass% or less, more preferably 60 mass% or less, even more preferably 55 mass% or less, and even more preferably 50 mass% or less.
  • the polyunsaturated fatty acid (PUFA) content in the total fatty acids of the glycerin fatty acid ester is, from the viewpoint of further improving the balance of plasticity, shape retention, handleability and storage stability, preferably 10 mass% or more, more preferably 15 mass% or more, even more preferably 18 mass% or more, even more preferably 20 mass% or more, even more preferably 25 mass% or more, and is preferably 45 mass% or less, more preferably 43 mass% or less, even more preferably 40 mass% or less, and even more preferably 35 mass% or less.
  • the polyunsaturated fatty acid (PUFA) content in the total fatty acids of the glycerin fatty acid ester of the oil composition in the manufacturing method for a plastic oil composition of this embodiment is, from the viewpoint of further improving the balance of plasticity, shape retention, handleability and storage stability, preferably 5 mass% or more, more preferably 10 mass% or more, even more preferably 15 mass% or more, even more preferably 18 mass% or more, even more preferably 20 mass% or more, even even more preferably 25 mass% or more, and is preferably 45 mass% or less, more preferably 43 mass% or less, even more preferably 40 mass% or less, and even more preferably 35 mass% or less.
  • the polyunsaturated fatty acid refers to an unsaturated fatty acid having two or more unsaturated bonds.
  • the step of mixing the raw materials containing the oil or fat composition may further include a step of adding an aqueous phase component containing water to the oil phase component containing the oil or fat composition.
  • the process includes a step of adding an aqueous phase component, it is preferable to include an emulsifying step.
  • the emulsifying step can be carried out by stirring at a temperature of 50° C. to 80° C., for example.
  • the method for producing a plastic oil and fat composition of the present embodiment may further include a step of quenching and kneading the oil and fat composition after the step of mixing the raw materials containing the oil and fat composition.
  • the quenching and kneading process is a process of plasticizing the oil and fat composition or the oil and fat raw material containing the oil and fat composition to obtain a plastic oil and fat composition.
  • a cooling mixer such as a perfector, a combinator, a votator, or a nexus.
  • the method for producing a plastic oil composition of this embodiment includes a step of reacting a fatty acid having 13 to 15 carbon atoms with glycerin to produce a glycerin fatty acid ester.
  • a glycerin fatty acid ester by producing a glycerin fatty acid ester by blending a fatty acid having 13 to 15 carbon atoms at an arbitrary content, it is possible to adjust the fatty acid composition of the entire oil composition for food preparation to an arbitrary composition.
  • the fatty acid having 13 to 15 carbon atoms commercially available food additives and reagents can be used, as well as fatty acids obtained by saponifying natural animal and vegetable oils, and fatty acids obtained by molecular distillation of such fatty acids as necessary.
  • the natural animal and vegetable oils may contain fatty acids having 13 to 15 carbon atoms as well as fatty acids having 12 carbon atoms at the same time. Therefore, by being able to produce the glycerin fatty acid ester using fatty acids having 13 to 15 carbon atoms, it becomes easier to adjust the mass ratio of the content of fatty acids having 12 carbon atoms to the content of fatty acids having 13 to 15 carbon atoms in the total fatty acids of the glycerin fatty acid ester.
  • the method for producing a plastic oil composition of the present embodiment may further include a step of transesterifying the glycerin fatty acid ester obtained as described above with an edible oil containing a glycerin fatty acid ester other than the above glycerin fatty acid ester, thereby further improving the balance between plasticity and shape retention.
  • the step of producing a glycerol fatty acid ester by reacting a fatty acid having a carbon number of 13 to 15 with glycerin, and the step of transesterifying the glycerol fatty acid ester obtained as described above with an edible fat or oil containing a glycerol fatty acid ester other than the glycerol fatty acid ester are preferably performed before the step of mixing a raw material containing an oil and fat composition.
  • the method for producing the plastic oil composition of this embodiment includes a step of transesterifying the above-mentioned glycerin fatty acid ester with an edible oil containing a glycerin fatty acid ester other than the above-mentioned glycerin fatty acid ester, the edible oil containing a glycerin fatty acid ester other than the above-mentioned glycerin fatty acid ester is not particularly limited.
  • vegetable oils and fats such as rapeseed oil, soybean oil, corn oil, sesame oil, coconut oil, palm oil, palm kernel oil, rice oil, cottonseed oil, safflower oil, sunflower oil, olive oil, linseed oil, peanut oil, monkey fat, cacao butter, shea butter, etc.; animal oils and fats such as beef tallow, lard, chicken fat, milk fat, and fish oil; and synthetic oils and fats such as medium-chain fatty acid triglycerides.
  • Vegetable oils and fats are preferred, and one or more selected from the group consisting of rapeseed oil, soybean oil, palm oil, and sunflower oil are more preferred.
  • processed oils and fats obtained by subjecting the above-mentioned oils and fats to treatments such as fractionation and hydrogenation can be included.
  • one or more types selected from the group consisting of vegetable oils and fats and processed oils and fats thereof are preferred, and one or more types selected from the group consisting of rapeseed oil, soybean oil, palm oil, sunflower oil and processed oils and fats thereof are more preferred.
  • interesterification can be carried out by a known method.
  • the interesterification method may be random interesterification or specific interesterification of fatty acids bonded to the 1- and 3-positions of glycerol, but random interesterification is preferred.
  • catalysts used for interesterification include chemical catalysts such as sodium methoxide and enzyme catalysts such as lipase.
  • the transesterified oil can be produced, for example, by the following method.
  • the resulting glycerol fatty acid ester is mixed with edible fats and oils containing glycerol fatty acid esters other than the above glycerol fatty acid esters, and 0.3 parts by mass of sodium methoxide is added as a catalyst to 100 parts by mass of the mixed oil, and a random transesterification reaction is carried out while stirring for 60 minutes under conditions of 80°C and a vacuum degree of 2.0 kPa. After the random transesterification reaction, the catalyst is removed by washing with water. After washing with water, decolorization treatment is carried out using activated clay, and further deodorization treatment is carried out to obtain each transesterification oil.
  • the content of the oil phase is preferably 50% by mass or more, more preferably 60% by mass or more, even more preferably 70% by mass or more, even more preferably 75% by mass or more, and preferably 99.4% by mass or less, more preferably 98% by mass or less, even more preferably 90% by mass or less, even more preferably 85% by mass or less.
  • the content of the water phase is preferably 0.6% by mass or more, more preferably 2% by mass or more, even more preferably 10% by mass or more, even more preferably 15% by mass or more, and preferably 50% by mass or less, more preferably 40% by mass or less, even more preferably 30% by mass or less, even more preferably 25% by mass or less.
  • the plastic oil composition of this embodiment may contain conventional known ingredients other than the oil and water, as long as the effect of the present invention is not impaired.
  • Known ingredients include, but are not limited to, milk, dairy products, proteins, carbohydrates, salts, acidulants, pH adjusters, antioxidants, spices, coloring ingredients, flavorings, emulsifiers, etc.
  • Milk includes cow's milk, etc.
  • carbohydrates include monosaccharides (glucose, fructose, galactose, mannose, etc.), disaccharides (lactose, sucrose, maltose, trehalose, etc.), oligosaccharides, sugar alcohols, starch, starch hydrolysates, polysaccharides, etc.
  • antioxidants include L-ascorbic acid, L-ascorbic acid derivatives, tocopherol, tocotrienol, lignan, ubiquinones, xanthins, oryzanol, plant sterols, catechins, polyphenols, tea extracts, etc.
  • Examples of spices include capsaicin, anethole, eugenol, cineole, zingerone, etc.
  • Examples of coloring components include carotene, annatto, astaxanthin, etc.
  • Examples of flavorings include butter flavor, milk flavor, etc.
  • Emulsifiers include lecithin, sorbitan fatty acid esters, polyglycerin fatty acid esters, monoglycerin fatty acid esters, organic acid glycerin fatty acid esters, sucrose fatty acid esters, polyglycerin condensed ricinoleic acid esters, propylene glycol fatty acid esters, calcium stearoyl lactylate, sodium stearoyl lactylate, polyoxyethylene sorbitan fatty acid esters, etc.
  • the method for producing a food product of this embodiment includes a step of preparing a food product using a raw material containing the plastic oil-and-fat composition obtained by the method for producing a plastic oil-and-fat composition of this embodiment.
  • the process for preparing food using raw materials containing the plastic oil composition is not limited, and examples thereof include a method of mixing the plastic oil composition of this embodiment with other raw materials, such as flour, seasonings, fragrances, emulsifiers, etc., and cooking with heat; a method of placing the plastic oil composition of this embodiment on bread, cakes, baked goods, etc.; a method of mixing the plastic oil composition of this embodiment with noodles, rice, meat, fish, vegetables, etc. that have been cooked with heat; and the like.
  • plastic oil composition of this embodiment as a stir-frying oil or frying oil for noodles, rice, meat, fish, vegetables, eggs, etc. can be mentioned.
  • Food products include, but are not limited to, breads such as bread, rolls, sweet buns, cooked bread, stollen, panettone, brioche, etc.; pastries such as Danish, croissants, pies, etc.; cakes such as pound cake, sponge cake, pancake, etc.; baked goods such as biscuits, cookies, baked donuts, bushés, waffles, etc.; sauteed meat, seafood, vegetables, etc.; processed egg foods such as omelets, etc.; noodles such as spaghetti, penne, etc.; rice dishes such as pilaf, doria, etc.; beverages such as milk, soy milk, milk drinks, lactic acid drinks, soft drinks, tea, coffee, etc.
  • the food manufacturing method of this embodiment uses a plastic oil composition produced by the plastic oil composition manufacturing method of this embodiment, and therefore has an excellent balance of plasticity and shape retention, making it suitable for use in food manufacturing.
  • the method for improving the flavor of a plastic oil and fat composition of this embodiment includes a step of mixing a raw material containing the oil and fat composition, wherein the oil and fat composition contains a glycerin fatty acid ester containing a fatty acid residue having a carbon number of 13 or more and 15 or less, the total fatty acids in the glycerin fatty acid ester contain fatty acids having a carbon number of 13 or more and 15 or less at 1.8% by mass or more and 100% by mass or less, and the content of fatty acids having a carbon number of 12 in the total fatty acids in the glycerin fatty acid ester is a mass ratio of 0 to 2.5 relative to the content of fatty acids having a carbon number of 13 or more and 15 or less.
  • the oil composition Details of the oil composition are as described above in the section on the method for producing the plastic oil composition of this embodiment, and therefore will be omitted here.
  • the flavor of the plastic oil composition can be improved.
  • the flavor of the dairy products or flavorings can be improved.
  • a method for producing a plastic oil composition comprising a step of mixing a raw material containing an oil composition,
  • the oil and fat composition contains a glycerin fatty acid ester containing a fatty acid residue having a carbon number of 13 to 15,
  • the glycerin fatty acid ester contains 1.8% by mass or more and 100% by mass or less of fatty acids having 13 or more and 15 or less carbon atoms in the total fatty acids of the glycerin fatty acid ester
  • a method for producing a plastic oil composition wherein the content of fatty acids having 12 carbon atoms in the total fatty acids of the glycerin fatty acid ester is in a mass ratio of 0 to 2.5 relative to the content of fatty acids having 13 to 15 carbon atoms.
  • [2] The method for producing a plastic oil composition described in [1], wherein the fatty acid having 13 or more and 15 or less carbon atoms includes one or more selected from the group consisting of tridecanoic acid, tetradecanoic acid, and pentadecanoic acid.
  • [3] A method for producing a plastic oil composition according to [1] or [2], wherein the content of fatty acids having 12 carbon atoms in the total fatty acids of the glycerin fatty acid ester is 0% by mass or more and 15% by mass or less.
  • [4] A method for producing a plastic oil composition according to [1] or [2], wherein the content of fatty acids having 14 carbon atoms in the total fatty acids of the glycerin fatty acid ester is 1.0% by mass or more and 100% by mass or less.
  • [5] The method for producing a plastic oil composition according to [1] or [2], wherein the glycerin fatty acid ester contains an interesterified oil.
  • [6] The method for producing a plastic oil composition according to [1] or [2], wherein the iodine value of the oil composition is 60 or more and 110 or less.
  • the method for producing a plastic oil composition according to [7] further comprises a step of transesterifying the glycerin fatty acid ester obtained by reacting the fatty acid having a carbon number of 13 to 15 and the glycerin with an edible oil containing a glycerin fatty acid ester other than the glycerin fatty acid ester.
  • a method for producing a food product comprising a step of preparing a food product using a raw material containing a plastic oil composition obtained by the method for producing a plastic oil composition described in [1] or [2].
  • a method for improving the flavor of a plastic oil-and-fat composition comprising a step of mixing a raw material containing an oil-and-fat composition,
  • the oil and fat composition contains a glycerin fatty acid ester containing a fatty acid residue having a carbon number of 13 to 15,
  • the glycerin fatty acid ester contains 1.8% by mass or more and 100% by mass or less of fatty acids having 13 or more and 15 or less carbon atoms in the total fatty acids of the glycerin fatty acid ester
  • a method for improving the flavor of a plastic oil composition wherein the content of fatty acids having 12 carbon atoms in the total fatty acids of the glycerin fatty acid ester is in a mass ratio of 0 to 2.5 relative to the content of fatty acids
  • the raw materials for the fats and oils used were as follows.
  • the fats and oils in each example were blended according to Table 4.
  • the interesterified oil was produced according to the blend in Table 1 and the method for producing interesterified oil described below.
  • Soybean oil Soybean white refined oil NS, manufactured by J-Oil Mills Co., Ltd.
  • Rapeseed oil AJINOMOTO smooth canola oil, manufactured by J-Oil Mills Co., Ltd.
  • Palm oil manufactured by J-Oil Mills Co., Ltd.
  • Palm olein Palm olein IV67, manufactured by J-Oil Mills Co., Ltd. Palm stearin: manufactured by J-Oil Mills Co., Ltd.
  • Glyceryl tritetradecanoate The one used in Production Example 1
  • Glyceryl tritridecanoate The one used in Production Example 1
  • Glyceryl tripentadecanoate The one used in Production Example 1 Palm kernel oil: manufactured by Fuji Oil Co., Ltd.
  • MCT MCT-1, manufactured by J-Oil Mills Co., Ltd.
  • glyceryl tritridecanoate and glyceryl tripentadecanoate the same production method as for glyceryl tritetradecanoate was carried out, except that tetradecanoic acid was changed to tridecanoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) or pentadecanoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), respectively.
  • transesterified oil composition (unit: parts by mass) in Table 1, each oil was blended, and 0.3 parts by mass of sodium methoxide was added as a catalyst to 100 parts by mass of the oil, and a random transesterification reaction was carried out while stirring for 60 minutes under conditions of 80°C and a vacuum degree of 2.0 kPa. After the random transesterification reaction, the catalyst was removed by washing with water. After washing with water, decolorization treatment was carried out using activated clay, and further deodorization treatment was carried out to obtain each transesterified oil.
  • ⁇ GC device Product name GC2010 (manufactured by Shimadzu Corporation) Column: SP-2560 (100 m x 0.25 mm x 0.2 ⁇ m) (manufactured by Sperco) ⁇ Inlet temperature: 250°C Carrier gas: Helium (29.1 ml/min) Split ratio: 25:1 Column temperature: 180°C 55min ⁇ (8°C/min) ⁇ 220°C 5min Detector: Hydrogen flame ion detector (260°C)
  • the obtained margarines were tasted by four expert panelists and evaluated for plasticity, shape retention, and flavor based on the following evaluation criteria.
  • plasticity the smoothness of the margarine when spread with a spoon was evaluated.
  • shape retention the margarine was evaluated for its ability to maintain a good hardness even after being placed on a spoon and left at room temperature for 5 minutes.
  • flavor the taste of butter flavor and skim milk powder was evaluated for its strong flavor.
  • the scores were determined by consensus of the expert panelists. For Examples 1-1 to 1-3, Comparative Example 1 was used as the standard (3 points), and for Examples 2-1 to 2-3, Comparative Example 2 was used as the standard (3 points). The results are shown in Table 4.
  • cookies were made as follows. 1. The fats and oils were mixed using a Hobart mixer fitted with a beater at medium speed for 1 minute 30 seconds. 2. Add the sifted caster sugar and salt and mix at medium speed for 1 minute 30 seconds. 3. Add water and mix on medium speed for 1 minute 30 seconds. 4. The flour was added and mixed at low speed for 30 seconds to obtain a cookie dough. 5. The dough was divided into 280 g portions and shaped into log shapes with a diameter of approximately 4 cm and a length of approximately 35 cm. 6. Wrap it in paper and chill it in the refrigerator for an hour. 7. The mixture was cut into pieces 1 cm thick with a knife and baked in an oven (top oven temperature setting: 180° C./bottom oven temperature setting: 180° C., 15 minutes).
  • the obtained cookies were eaten by four expert panelists and evaluated for crispness and flavor based on the following evaluation criteria: Examples 1-1 to 1-3 were evaluated based on Comparative Example 1 (3.0 points), and Examples 2-1 to 2-3 were evaluated based on Comparative Example 2 (3.0 points).
  • the margarines obtained in the Examples had a better balance of plasticity and shape retention than the Comparative Examples, and also had a better flavor. Furthermore, the cookies made using the margarines obtained in the Examples were evaluated as being equal to or better than the cookies made using the margarines obtained in the Comparative Examples in terms of crispness and flavor.
  • Comparative Example 1' was used as the standard (3 points) for Examples 1-4 to 1-6. Comparative Example 1' was evaluated simultaneously with Examples 1-4 to 1-6 using the same composition of fats and oils as in Comparative Example 1 described above. The results are shown in Table 5.

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Abstract

A plastic oil/fat composition production method including a step for mixing starting materials including an oil/fat composition, wherein: the oil/fat composition contains a C13-15 fatty acid residue-containing glycerin fatty acid ester; a C13-15 fatty acid is contained in the amount of 1.8-100 mass% among the total fatty acids of the glycerin fatty acid ester; and the C12 fatty acid content among the total fatty acids of the glycerin fatty acid ester is 0-2.5 by mass ratio relative to the C13-15 fatty acid content.

Description

可塑性油脂組成物の製造方法および食品の製造方法Method for producing plastic oil composition and method for producing food
　本発明は、可塑性油脂組成物の製造方法および食品の製造方法に関する。 The present invention relates to a method for producing a plastic oil composition and a method for producing a food product.
　可塑性油脂組成物について、特許文献１および２のものが挙げられる。 Patent documents 1 and 2 are examples of plastic oil compositions.
　特許文献１には、構成脂肪酸中に炭素数１６以上の不飽和脂肪酸を有する乳化剤と、構成脂肪酸中に炭素数１４以下の飽和脂肪酸を有するジグリセリン脂肪酸エステルと、を含み、油脂の含有量が７０質量％以上である、可塑性油脂組成物が記載され、水性成分の割合が高くても安定で、かつ、口どけのよい、含気泡状の組成物、および、当該含気泡組成物のベースとなる可塑性油脂組成物を提供できる、とされている。 Patent Document 1 describes a plastic oil composition that contains an emulsifier having unsaturated fatty acids with 16 or more carbon atoms in its constituent fatty acids and a diglycerol fatty acid ester having saturated fatty acids with 14 or less carbon atoms in its constituent fatty acids, and has an oil content of 70% by mass or more. It is said that the composition can provide an air-containing foam-like composition that is stable and melts easily in the mouth even when the proportion of aqueous components is high, and a plastic oil composition that serves as the base for the air-containing composition.
　特許文献２には、２０℃で液体である油脂を７０質量％以上と、（Ａ）ポリグリセリン脂肪酸エステルを５～３０質量％、または（Ｂ）ポリグリセリン脂肪酸エステルを３～１２質量％および極度硬化油および／またはワックスを２～１０質量％含有し、かつポリグリセリン脂肪酸エステルと極度硬化油および／またはワックスとの合計が６質量％以上、とを含有する可塑性油脂組成物であって、ポリグリセリン脂肪酸エステルが、構成脂肪酸１００％中、炭素数が１６～１８の飽和脂肪酸の含有量が９０％以上であり、可塑性油脂組成物が、可塑性油脂組成物の全構成脂肪酸の質量に対して、４０質量％以下の、炭素数１６以上の飽和脂肪酸を含有し、動的粘弾性測定における１０℃と３０℃の貯蔵弾性率の常用対数の数値の差が、１．０未満であることを特徴とする可塑性油脂組成物が記載されている。当該可塑性油脂組成物によれば、主原料としてパーム油を使用しなくとも、幅広い温度域で可塑性が良好で、作業性において非常に好適な物性をそなえた可塑性油脂組成物を提供できることが記載されている。 Patent Document 2 describes a plastic oil composition that contains 70% by mass or more of an oil that is liquid at 20°C, and (A) 5 to 30% by mass of a polyglycerol fatty acid ester, or (B) 3 to 12% by mass of a polyglycerol fatty acid ester and 2 to 10% by mass of an extremely hardened oil and/or wax, and the total of the polyglycerol fatty acid ester and the extremely hardened oil and/or wax is 6% by mass or more, wherein the polyglycerol fatty acid ester contains 90% or more of saturated fatty acids having 16 to 18 carbon atoms out of 100% of the constituent fatty acids, the plastic oil composition contains 40% or less by mass of saturated fatty acids having 16 or more carbon atoms relative to the mass of the total constituent fatty acids of the plastic oil composition, and the difference in the common logarithm of the storage modulus at 10°C and 30°C in dynamic viscoelasticity measurement is less than 1.0. It is described that this plastic oil composition has good plasticity over a wide temperature range, even without using palm oil as the main raw material, and can provide a plastic oil composition with very favorable physical properties in terms of workability.
特開２０２１－１５８９４３号公報JP 2021-158943 A 特開２０２１－１６８６２０号公報JP 2021-168620 A
　本発明は、可塑性および保形性のバランスを向上できる可塑性油脂組成物の製造方法を提供するものである。 The present invention provides a method for producing a plastic oil composition that can improve the balance between plasticity and shape retention.
　本発明者らは、可塑性油脂組成物中の油脂組成物が炭素数が１３以上１５以下である脂肪酸残基を含むグリセリン脂肪酸エステルを含み、当該グリセリン脂肪酸エステルにおいて、グリセリン脂肪酸エステルの総脂肪酸中の、炭素数が１３以上１５以下である脂肪酸の含有量を所定の範囲内とするとともに、炭素数が１３以上１５以下である脂肪酸の含有量に対する、炭素数が１２である脂肪酸の含有量の質量比を所定の範囲内とすることによって、可塑性油脂組成物の可塑性および保形性を向上できることを見出した。 The inventors have found that the plasticity and shape retention of a plastic oil composition can be improved by including a glycerin fatty acid ester in the oil composition containing a fatty acid residue having a carbon number of 13 or more and 15 or less, and by controlling the content of fatty acids having a carbon number of 13 or more and 15 or less in the total fatty acids of the glycerin fatty acid ester within a specified range and controlling the mass ratio of the content of fatty acids having a carbon number of 12 to the content of fatty acids having a carbon number of 13 or more and 15 or less within a specified range.
　本発明は、以下の可塑性油脂組成物の製造方法および食品の製造方法を提供する。 The present invention provides the following method for producing a plastic oil composition and method for producing a food product.
［１］
　油脂組成物を含む原料を混合する工程を含む、可塑性油脂組成物の製造方法であって、
　前記油脂組成物が、炭素数が１３以上１５以下である脂肪酸残基を含むグリセリン脂肪酸エステルを含有し、
　前記グリセリン脂肪酸エステルの総脂肪酸中、炭素数が１３以上１５以下である脂肪酸を１．８質量％以上１００質量％以下含有し、
　前記グリセリン脂肪酸エステルの総脂肪酸中、炭素数が１２である脂肪酸の含有量が、前記炭素数が１３以上１５以下である脂肪酸の含有量に対する質量比で０以上２．５以下である、可塑性油脂組成物の製造方法。
［２］
　前記炭素数が１３以上１５以下である脂肪酸が、トリデカン酸、テトラデカン酸およびペンタデカン酸からなる群から選択される１種または２種以上を含む、［１］に記載の可塑性油脂組成物の製造方法。
［３］
　前記グリセリン脂肪酸エステルの総脂肪酸中、炭素数が１２である脂肪酸の含有量が、０質量％以上１５質量％以下である、［１］または［２］に記載の可塑性油脂組成物の製造方法。
［４］
　前記グリセリン脂肪酸エステルの総脂肪酸中、炭素数が１４である脂肪酸の含有量が、１．０質量％以上１００質量％以下である、［１］～［３］のいずれかに記載の可塑性油脂組成物の製造方法。
［５］
　前記グリセリン脂肪酸エステルの総脂肪酸中、飽和脂肪酸（ＳＦＡ）含有量が、２０質量％以上６５質量％以下である、［１］～［４］のいずれかに記載の可塑性油脂組成物の製造方法。
［６］
　前記グリセリン脂肪酸エステルの総脂肪酸中、多価不飽和脂肪酸（ＰＵＦＡ）含有量が、５質量％以上４５質量％以下である、［１］～［５］のいずれかに記載の可塑性油脂組成物の製造方法。
［７］
　グリセリン脂肪酸エステルの総脂肪酸中、炭素数が１８の不飽和脂肪酸の含有量が、３１質量％以上９０質量％以下である、［１］～［６］のいずれかに記載の可塑性油脂組成物の製造方法。
［８］
　前記グリセリン脂肪酸エステルがエステル交換油を含む、［１］～［７］のいずれかに記載の可塑性油脂組成物の製造方法。
［９］
　前記油脂組成物のヨウ素価が、６０以上１１０以下である、［１］～［８］のいずれかに記載の可塑性油脂組成物の製造方法。
［１０］
　前記油脂組成物のヨウ素価が、４０以上１１０以下である、［１］～［８］のいずれかに記載の可塑性油脂組成物の製造方法。
［１１］
　炭素数が１３以上１５以下である脂肪酸およびグリセリンを反応させてグリセリン脂肪酸エステルを製造する工程を含む、［１］～［１０］のいずれかに記載の可塑性油脂組成物の製造方法。
［１２］
　炭素数が１３以上１５以下である前記脂肪酸および前記グリセリンを反応させて得られる前記グリセリン脂肪酸エステルと、前記グリセリン脂肪酸エステル以外のグリセリン脂肪酸エステルを含む食用油脂とをエステル交換する工程をさらに含む、［１１］に記載の可塑性油脂組成物の製造方法。
［１３］
　［１］～［１２］のいずれかに記載の可塑性油脂組成物の製造方法で得られた可塑性油脂組成物を含む原材料を用いて食品を調製する工程を含む、食品の製造方法。
［１４］
　油脂組成物を含む原料を混合する工程を含む、可塑性油脂組成物の風味の向上方法であって、
　前記油脂組成物が、炭素数が１３以上１５以下である脂肪酸残基を含むグリセリン脂肪酸エステルを含有し、
　前記グリセリン脂肪酸エステルの総脂肪酸中、炭素数が１３以上１５以下である脂肪酸を１．８質量％以上１００質量％以下含有し、
　前記グリセリン脂肪酸エステルの総脂肪酸中、炭素数が１２である脂肪酸の含有量が、前記炭素数が１３以上１５以下である脂肪酸の含有量に対する質量比で０以上２．５以下である、可塑性油脂組成物の風味の向上方法。 [1]
A method for producing a plastic oil composition, comprising a step of mixing a raw material containing an oil composition,
The oil and fat composition contains a glycerin fatty acid ester containing a fatty acid residue having a carbon number of 13 to 15,
The glycerin fatty acid ester contains 1.8% by mass or more and 100% by mass or less of fatty acids having 13 or more and 15 or less carbon atoms in the total fatty acids of the glycerin fatty acid ester,
A method for producing a plastic oil composition, wherein the content of fatty acids having 12 carbon atoms in the total fatty acids of the glycerin fatty acid ester is in a mass ratio of 0 to 2.5 relative to the content of fatty acids having 13 to 15 carbon atoms.
[2]
The method for producing a plastic oil composition described in [1], wherein the fatty acid having 13 or more and 15 or less carbon atoms includes one or more selected from the group consisting of tridecanoic acid, tetradecanoic acid, and pentadecanoic acid.
[3]
A method for producing a plastic oil composition according to [1] or [2], wherein the content of fatty acids having 12 carbon atoms in the total fatty acids of the glycerin fatty acid ester is 0% by mass or more and 15% by mass or less.
[4]
The method for producing a plastic oil composition according to any one of [1] to [3], wherein the content of fatty acids having 14 carbon atoms in the total fatty acids of the glycerin fatty acid ester is 1.0% by mass or more and 100% by mass or less.
[5]
The method for producing a plastic oil composition according to any one of [1] to [4], wherein the glycerin fatty acid ester has a saturated fatty acid (SFA) content of 20% by mass or more and 65% by mass or less of the total fatty acids.
[6]
A method for producing a plastic oil composition according to any one of [1] to [5], wherein the polyunsaturated fatty acid (PUFA) content in the total fatty acids of the glycerin fatty acid ester is 5% by mass or more and 45% by mass or less.
[7]
The method for producing a plastic oil composition according to any one of [1] to [6], wherein the content of unsaturated fatty acids having 18 carbon atoms in the total fatty acids of the glycerin fatty acid ester is 31% by mass or more and 90% by mass or less.
[8]
The method for producing a plastic oil composition according to any one of [1] to [7], wherein the glycerin fatty acid ester contains an interesterified oil.
[9]
The method for producing a plastic oil composition according to any one of [1] to [8], wherein the iodine value of the oil composition is 60 or more and 110 or less.
[10]
The method for producing a plastic oil composition according to any one of [1] to [8], wherein the iodine value of the oil composition is 40 or more and 110 or less.
[11]
A method for producing a plastic oil composition according to any one of [1] to [10], comprising a step of producing a glycerin fatty acid ester by reacting a fatty acid having 13 to 15 carbon atoms with glycerin.
[12]
The method for producing a plastic oil composition according to [11] further comprises a step of transesterifying the glycerin fatty acid ester obtained by reacting the fatty acid having a carbon number of 13 to 15 and the glycerin with an edible oil containing a glycerin fatty acid ester other than the glycerin fatty acid ester.
[13]
A method for producing a food product, comprising the step of preparing a food product using a raw material containing a plastic oil composition obtained by the method for producing a plastic oil composition according to any one of [1] to [12].
[14]
A method for improving the flavor of a plastic oil-and-fat composition, comprising a step of mixing a raw material containing an oil-and-fat composition,
The oil and fat composition contains a glycerin fatty acid ester containing a fatty acid residue having a carbon number of 13 to 15,
The glycerin fatty acid ester contains 1.8% by mass or more and 100% by mass or less of fatty acids having 13 or more and 15 or less carbon atoms in the total fatty acids of the glycerin fatty acid ester,
A method for improving the flavor of a plastic oil composition, wherein the content of fatty acids having 12 carbon atoms in the total fatty acids of the glycerin fatty acid ester is in a mass ratio of 0 to 2.5 relative to the content of fatty acids having 13 to 15 carbon atoms.
　本発明によれば、可塑性および保形性のバランスを向上できる可塑性油脂組成物の製造方法を提供することができる。 The present invention provides a method for producing a plastic oil composition that can improve the balance between plasticity and shape retention.
　以下、本発明の実施の形態について、各成分の具体例を挙げて説明する。なお、本明細書では、数値範囲を示す「Ａ～Ｂ」は特に断りがなければ、Ａ以上Ｂ以下を表す。また、本明細書において数値範囲の上限値及び下限値を示したときは、上限値及び下限値を適宜組み合わせることができ、それにより得られた数値範囲も開示しているものとする。 Below, the embodiments of the present invention will be described with specific examples of each component. In this specification, "A to B" indicating a numerical range means A or more and B or less, unless otherwise specified. In addition, when an upper limit and a lower limit of a numerical range are indicated in this specification, the upper limit and the lower limit can be appropriately combined, and the numerical range obtained by combining them is also considered to be disclosed.
（可塑性油脂組成物の製造方法）
　本実施形態に係る可塑性油脂組成物の製造方法は、油脂組成物を含む原料を混合する工程を含み、油脂組成物は、炭素数が１３以上１５以下である脂肪酸残基を含むグリセリン脂肪酸エステルを含有し、グリセリン脂肪酸エステルの総脂肪酸中、炭素数が１３以上１５以下である脂肪酸を１．８質量％以上１００質量％以下含有し、グリセリン脂肪酸エステルの総脂肪酸中、炭素数が１２である脂肪酸の含有量が、炭素数が１３以上１５以下である脂肪酸の含有量に対する質量比で０以上２．５以下である。 (Method for producing plastic oil composition)
The method for producing a plastic oil composition according to this embodiment includes a step of mixing raw materials containing an oil composition, and the oil composition contains a glycerin fatty acid ester containing a fatty acid residue having a carbon number of 13 or more and 15 or less, and the total fatty acids in the glycerin fatty acid ester contain fatty acids having a carbon number of 13 or more and 15 or less at 1.8% by mass or more and 100% by mass or less, and the content of fatty acids having a carbon number of 12 in the total fatty acids in the glycerin fatty acid ester is a mass ratio of 0 to 2.5 relative to the content of fatty acids having a carbon number of 13 or more and 15 or less.
　本実施形態において、グリセリン脂肪酸エステルとは、グリセリンと１つ以上３つ以下の脂肪酸がエステル結合したものを表す。本実施形態において、グリセリン脂肪酸エステルは、好ましくは、グリセリンに脂肪酸が３つ結合したものである。 In this embodiment, the glycerin fatty acid ester refers to an ester bond between glycerin and one or more and three or less fatty acids. In this embodiment, the glycerin fatty acid ester is preferably an ester bond between glycerin and three fatty acids.
　本実施形態の可塑性油脂組成物の製造方法において、グリセリン脂肪酸エステルの総脂肪酸中、炭素数が１３以上１５以下である脂肪酸の含有量は、１．８質量％以上、好ましくは３．０質量％以上、より好ましくは５．０質量％以上、さらに好ましくは６．０質量％以上であり、そして１００質量％以下であり、例えば９０質量％以下であってもよく、８０質量％以下であってもよく、６０質量％以下であってもよく、５０質量％以下であってもよく、４０質量％以下であってもよい。
　炭素数が１３以上１５以下である脂肪酸の含有量が上記範囲内であることにより、可塑性油脂組成物の可塑性、保形性および風味のバランスを向上できる。 In the method for producing a plastic oil composition of this embodiment, the content of fatty acids having a carbon number of 13 or more and 15 or less in the total fatty acids of the glycerin fatty acid ester is 1.8 mass% or more, preferably 3.0 mass% or more, more preferably 5.0 mass% or more, and even more preferably 6.0 mass% or more, and is 100 mass% or less, for example, may be 90 mass% or less, 80 mass% or less, 60 mass% or less, 50 mass% or less, or 40 mass% or less.
By ensuring that the content of fatty acids having 13 or more and 15 or less carbon atoms is within the above range, the balance of plasticity, shape retention, and flavor of the plastic oil composition can be improved.
　グリセリン脂肪酸エステルにおいて、グリセリン脂肪酸エステルの総脂肪酸中、炭素数が１３以上１５以下である脂肪酸の含有量に対する炭素数が１２である脂肪酸の含有量の質量比は、２．５以下、好ましくは２．３以下、より好ましくは２．１以下、さらに好ましくは１．８以下、さらにより好ましくは１．５以下、より一層好ましくは１．０以下であり、そして０以上である。
　さらにグリセリン脂肪酸エステルにおいて、グリセリン脂肪酸エステルの総脂肪酸中、炭素数が１３以上１５以下である脂肪酸の含有量に対する炭素数が１２である脂肪酸の含有量の質量比は、２．５０以下、好ましくは２．００以下、より好ましくは１．５０以下、さらに好ましくは１．００以下、さらにより好ましくは０．５０以下、より一層好ましくは０．１７未満、さらにより一層好ましくは０．１５以下であり、そして０以上である。
　炭素数が１３以上１５以下である脂肪酸の含有量に対する炭素数が１２である脂肪酸の含有量の質量比が上記範囲内であることにより、可塑性油脂組成物の可塑性、保形性および風味のバランスを向上できる。 In the glycerin fatty acid ester, the mass ratio of the content of fatty acids having 12 carbon atoms to the content of fatty acids having 13 or more and 15 or less carbon atoms in the total fatty acids of the glycerin fatty acid ester is 2.5 or less, preferably 2.3 or less, more preferably 2.1 or less, even more preferably 1.8 or less, even more preferably 1.5 or less, still more preferably 1.0 or less, and is 0 or more.
Furthermore, in the glycerin fatty acid ester, the mass ratio of the content of fatty acids having 12 carbon atoms to the content of fatty acids having 13 or more and 15 or less carbon atoms in the total fatty acids of the glycerin fatty acid ester is 2.50 or less, preferably 2.00 or less, more preferably 1.50 or less, even more preferably 1.00 or less, even more preferably 0.50 or less, even more preferably less than 0.17, even more preferably 0.15 or less, and is 0 or more.
By having the mass ratio of the content of fatty acids having 12 carbon atoms to the content of fatty acids having 13 or more and 15 or less carbon atoms within the above range, the balance of plasticity, shape retention, and flavor of the plastic oil composition can be improved.
　本発明者らは、本実施形態の可塑性油脂組成物の製造方法において、炭素数が１３以上１５以下である脂肪酸の含有量および、炭素数が１３以上１５以下である脂肪酸の含有量に対する炭素数が１２である脂肪酸の含有量の質量比を所定の範囲内とすることにより、可塑性および保形性を向上できることを見出した。 The inventors have found that in the method for producing a plastic oil composition of this embodiment, by setting the content of fatty acids having 13 to 15 carbon atoms and the mass ratio of the content of fatty acids having 12 carbon atoms to the content of fatty acids having 13 to 15 carbon atoms within a specified range, the plasticity and shape retention can be improved.
　グリセリン脂肪酸エステルにおいて、グリセリン脂肪酸エステルの総脂肪酸中、炭素数が１２である脂肪酸の含有量は、可塑性、保形性および風味のバランスをより向上させる観点から、好ましくは１５質量％以下、より好ましくは１４質量％以下、さらに好ましくは１３質量％以下、さらにより好ましくは１０質量％以下、より一層好ましくは５質量％以下である。炭素数が１２である脂肪酸の含有量の下限に制限はないが、例えば０質量％以上である。
　また、グリセリン脂肪酸エステルにおいて、グリセリン脂肪酸エステルの総脂肪酸中、炭素数が１２である脂肪酸の含有量は、可塑性、保形性および風味のバランスをより向上させる観点から、好ましくは１５質量％以下、より好ましくは１０質量％以下、さらに好ましくは５質量％以下、さらにより好ましくは３質量％以下、より一層好ましくは２質量％以下、さらにより一層好ましくは１．５質量％以下である。炭素数が１２である脂肪酸の含有量の下限に制限はないが、例えば０質量％以上である。 In the glycerin fatty acid ester, the content of fatty acids having 12 carbon atoms in the total fatty acids of the glycerin fatty acid ester is preferably 15% by mass or less, more preferably 14% by mass or less, even more preferably 13% by mass or less, still more preferably 10% by mass or less, and even more preferably 5% by mass or less, from the viewpoint of further improving the balance of plasticity, shape retention, and flavor. There is no lower limit for the content of fatty acids having 12 carbon atoms, but it is, for example, 0% by mass or more.
In addition, in the glycerin fatty acid ester, the content of fatty acids having 12 carbon atoms in the total fatty acids of the glycerin fatty acid ester is preferably 15% by mass or less, more preferably 10% by mass or less, even more preferably 5% by mass or less, still more preferably 3% by mass or less, even more preferably 2% by mass or less, and even more preferably 1.5% by mass or less, from the viewpoint of further improving the balance of plasticity, shape retention, and flavor. There is no lower limit for the content of fatty acids having 12 carbon atoms, but it is, for example, 0% by mass or more.
　グリセリン脂肪酸エステルにおいて、グリセリン脂肪酸エステルの総脂肪酸中、炭素数が１４である脂肪酸の含有量は、保形性をより向上させる観点および血糖値低下機能をより向上させる観点から、好ましくは１．０質量％以上、より好ましくは２．０質量％以上、さらに好ましくは３．０質量％以上、さらにより好ましくは４．０質量％以上、より一層好ましくは４．５質量％以上であり、また融点等の物性を適正な範囲とし、取り扱い性をより向上させる観点から、好ましくは１００質量％以下、より好ましくは９０質量％以下、さらに好ましくは７０質量％以下、さらにより好ましくは５０質量％以下、より一層好ましくは４０質量％以下である。 In the glycerin fatty acid ester, the content of fatty acids having 14 carbon atoms in the total fatty acids of the glycerin fatty acid ester is preferably 1.0% by mass or more, more preferably 2.0% by mass or more, even more preferably 3.0% by mass or more, even more preferably 4.0% by mass or more, and even more preferably 4.5% by mass or more, from the viewpoint of further improving shape retention and blood glucose level lowering function, and is preferably 100% by mass or less, more preferably 90% by mass or less, even more preferably 70% by mass or less, even more preferably 50% by mass or less, and even more preferably 40% by mass or less, from the viewpoint of keeping physical properties such as the melting point in an appropriate range and further improving handleability.
　グリセリン脂肪酸エステルにおいて、グリセリン脂肪酸エステルの総脂肪酸中、炭素数が１８の不飽和脂肪酸の含有量は、可塑性、保形性および風味のバランスをより向上させる観点から、好ましくは３１質量％以上、より好ましくは３５質量％以上、さらに好ましくは４０質量％以上、さらにより好ましくは４５質量％以上、より一層好ましくは５０質量％以上であり、また好ましくは９０質量％以下、より好ましくは８５質量％以下、さらに好ましくは８０質量％以下、さらにより好ましくは７５質量％以下である。 In the glycerin fatty acid ester, the content of unsaturated fatty acids having 18 carbon atoms in the total fatty acids of the glycerin fatty acid ester is preferably 31% by mass or more, more preferably 35% by mass or more, even more preferably 40% by mass or more, even more preferably 45% by mass or more, even more preferably 50% by mass or more, from the viewpoint of further improving the balance of plasticity, shape retention, and flavor, and is also preferably 90% by mass or less, more preferably 85% by mass or less, even more preferably 80% by mass or less, and even more preferably 75% by mass or less.
　炭素数が１３以上１５以下である脂肪酸は、好ましくはトリデカン酸、テトラデカン酸およびペンタデカン酸からなる群から選択される１種または２種以上を含む。トリデカン酸は炭素数１３の飽和脂肪酸であり、テトラデカン酸は炭素数１４の飽和脂肪酸であり、ペンタデカン酸は炭素数１５の飽和脂肪酸である。炭素数が１３以上１５以下である脂肪酸が飽和脂肪酸であることにより、可塑性および保形性のバランスをより向上させることができる。また、テトラデカン酸は、パーム核油、ヤシ油および乳脂等の天然の油脂に多く含まれている。 The fatty acid having 13 to 15 carbon atoms preferably includes one or more selected from the group consisting of tridecanoic acid, tetradecanoic acid, and pentadecanoic acid. Tridecanoic acid is a saturated fatty acid having 13 carbon atoms, tetradecanoic acid is a saturated fatty acid having 14 carbon atoms, and pentadecanoic acid is a saturated fatty acid having 15 carbon atoms. By using a fatty acid having 13 to 15 carbon atoms as a saturated fatty acid, the balance between plasticity and shape retention can be further improved. Tetradecanoic acid is also found in large amounts in natural fats and oils such as palm kernel oil, coconut oil, and milk fat.
　グリセリン脂肪酸エステルは、好ましくはエステル交換油を含む。エステル交換油を含むことにより、可塑性をより向上させることができる。
　グリセリン脂肪酸エステルがエステル交換油を含む場合、グリセリン脂肪酸エステル全体に対するエステル交換油の含有量は、好ましくは１０質量％以上、より好ましくは２０質量％以上、さらに好ましくは３０質量％以上、さらにより好ましくは４０質量％以上であり、そして好ましくは１００質量％以下である。
　また、グリセリン脂肪酸エステル全体に対するエステル交換油の含有量は、好ましくは１質量％以上、より好ましくは３質量％以上、さらに好ましくは５質量％以上、さらにより好ましくは１０質量％以上、より一層好ましくは１５質量％以上であり、そして好ましくは１００質量％以下である。
　エステル交換油の製造方法については後述する。 The glycerin fatty acid ester preferably contains an interesterified oil, which can further improve the plasticity.
When the glycerin fatty acid ester contains an interesterified oil, the content of the interesterified oil relative to the entire glycerin fatty acid ester is preferably 10% by mass or more, more preferably 20% by mass or more, even more preferably 30% by mass or more, still more preferably 40% by mass or more, and preferably 100% by mass or less.
In addition, the content of the transesterified oil relative to the total glycerin fatty acid ester is preferably 1 mass% or more, more preferably 3 mass% or more, even more preferably 5 mass% or more, still more preferably 10 mass% or more, even more preferably 15 mass% or more, and preferably 100 mass% or less.
The method for producing the interesterified oil will be described later.
　グリセリン脂肪酸エステルがエステル交換油を含む場合、エステル交換油以外の食用油脂を含んでもよい。食用油脂については特に制限されないが、例えば、菜種油、大豆油、コーン油、ゴマ油、ヤシ油、パーム油、パーム核油、米油、綿実油、紅花油、ヒマワリ油、オリーブ油、亜麻仁油、落花生油、サル脂、カカオ脂、シア脂などの植物油脂；牛脂、豚脂、鶏脂、乳脂、魚油などの動物油脂；及び中鎖脂肪酸トリグリセリドなどの合成油脂が挙げられる。また、上記油脂に分別、水素添加等の処理を施した加工油脂が挙げられる。これらの中でも、好ましくは植物油脂およびその加工油脂からなる群から選択される１種又は２種以上であり、より好ましくは菜種油、大豆油、パーム油、ヒマワリ油およびそれらの加工油脂からなる群から選択される１種又は２種以上である。また、前述の炭素数が１３以上１５以下である脂肪酸残基を含むグリセリン脂肪酸エステルのエステル交換油以外の、エステル交換油を含んでも良い。当該エステル交換油の原料油脂は前述の食用油脂から適宜選択することができる。 When the glycerin fatty acid ester contains an interesterified oil, it may contain edible oils and fats other than the interesterified oil. The edible oils and fats are not particularly limited, but examples thereof include vegetable oils and fats such as rapeseed oil, soybean oil, corn oil, sesame oil, coconut oil, palm oil, palm kernel oil, rice oil, cottonseed oil, safflower oil, sunflower oil, olive oil, linseed oil, peanut oil, monkey fat, cacao butter, and shea butter; animal oils and fats such as beef tallow, lard, chicken fat, milk fat, and fish oil; and synthetic oils and fats such as medium-chain fatty acid triglycerides. In addition, processed oils and fats obtained by subjecting the above-mentioned oils and fats to treatments such as fractionation and hydrogenation are also included. Among these, one or more types selected from the group consisting of vegetable oils and fats and their processed oils and fats are preferred, and one or more types selected from the group consisting of rapeseed oil, soybean oil, palm oil, sunflower oil, and their processed oils and fats are more preferred. The oil may also contain an interesterified oil other than the interesterified oil of a glycerin fatty acid ester containing a fatty acid residue having a carbon number of 13 to 15. The raw material fat of the interesterified oil may be appropriately selected from the edible fats and oils described above.
　本実施形態の可塑性油脂組成物の製造方法における油脂組成物の融点は、取り扱い性をより良好とする観点から、好ましくは８０℃以下、より好ましくは７０℃以下、さらに好ましくは６０℃以下である。油脂組成物の融点の下限に制限はないが、例えば１０℃以上であってもよく、２０℃以上であってもよい。 The melting point of the oil composition in the method for producing a plastic oil composition of this embodiment is preferably 80°C or lower, more preferably 70°C or lower, and even more preferably 60°C or lower, from the viewpoint of improving handleability. There is no lower limit for the melting point of the oil composition, but it may be, for example, 10°C or higher, or 20°C or higher.
　本実施形態の可塑性油脂組成物の製造方法における油脂組成物のヨウ素価は、取り扱い性をより向上させる観点から、好ましくは６０以上、より好ましくは６５以上、さらに好ましくは７０以上であり、そして保形性および保存安定性のバランスをより向上させる観点から、好ましくは１１０以下、より好ましくは１０５以下、さらに好ましくは１００以下、さらにより好ましくは９０以下、より一層好ましくは８５以下、さらにより一層好ましくは８０以下である。
　また、本実施形態の可塑性油脂組成物の製造方法における油脂組成物のヨウ素価は、取り扱い性をより向上させる観点から、好ましくは４０以上、より好ましくは５０以上、さらに好ましくは６０以上、さらにより好ましくは７０以上であり、そして保形性および保存安定性のバランスをより向上させる観点から、好ましくは１１０以下、より好ましくは１０５以下、さらに好ましくは１００以下、さらにより好ましくは９０以下、より一層好ましくは８５以下、さらにより一層好ましくは８０以下である。 The iodine value of the oil composition in the method for producing a plastic oil composition of this embodiment is, from the viewpoint of further improving handleability, preferably 60 or more, more preferably 65 or more, and even more preferably 70 or more, and from the viewpoint of further improving the balance between shape retention and storage stability, preferably 110 or less, more preferably 105 or less, even more preferably 100 or less, even more preferably 90 or less, even more preferably 85 or less, and even more preferably 80 or less.
In addition, the iodine value of the oil composition in the manufacturing method for a plastic oil composition of this embodiment is, from the viewpoint of further improving handleability, preferably 40 or more, more preferably 50 or more, even more preferably 60 or more, and even more preferably 70 or more, and from the viewpoint of further improving the balance between shape retention and storage stability, is preferably 110 or less, more preferably 105 or less, even more preferably 100 or less, even more preferably 90 or less, even more preferably 85 or less, and even more preferably 80 or less.
　本実施形態の可塑性油脂組成物の製造方法における油脂組成物の、グリセリン脂肪酸エステルの総脂肪酸中の飽和脂肪酸（ＳＦＡ）含有量は、可塑性、保形性および取り扱い性のバランスをより向上させる観点から、好ましくは２０質量％以上、より好ましくは２３質量％以上、さらに好ましくは２５質量％以上、さらにより好ましくは３０質量％以上であり、そして好ましくは６０質量％以下、より好ましくは５５質量％以下、さらに好ましくは５０質量％以下である。
　また、本実施形態の可塑性油脂組成物の製造方法における油脂組成物の、グリセリン脂肪酸エステルの総脂肪酸中の飽和脂肪酸（ＳＦＡ）含有量は、可塑性、保形性および取り扱い性のバランスをより向上させる観点から、好ましくは２０質量％以上、より好ましくは２３質量％以上、さらに好ましくは２５質量％以上、さらにより好ましくは３０質量％以上であり、そして好ましくは６５質量％以下、より好ましくは６０質量％以下、さらに好ましくは５５質量％以下、さらに好ましくは５０質量％以下である。 In the oil composition in the method for producing a plastic oil composition of this embodiment, the saturated fatty acid (SFA) content in the total fatty acids of the glycerin fatty acid ester is, from the viewpoint of further improving the balance between plasticity, shape retention and handleability, preferably 20% by mass or more, more preferably 23% by mass or more, even more preferably 25% by mass or more, even more preferably 30% by mass or more, and is preferably 60% by mass or less, more preferably 55% by mass or less, and even more preferably 50% by mass or less.
In addition, the saturated fatty acid (SFA) content in the total fatty acids of the glycerin fatty acid ester of the oil composition in the manufacturing method for a plastic oil composition of this embodiment is, from the viewpoint of further improving the balance of plasticity, shape retention and handleability, preferably 20 mass% or more, more preferably 23 mass% or more, even more preferably 25 mass% or more, even more preferably 30 mass% or more, and is preferably 65 mass% or less, more preferably 60 mass% or less, even more preferably 55 mass% or less, and even more preferably 50 mass% or less.
　本実施形態の可塑性油脂組成物の製造方法における油脂組成物の、グリセリン脂肪酸エステルの総脂肪酸中の多価不飽和脂肪酸（ＰＵＦＡ）含有量は、可塑性、保形性、取り扱い性および保存安定性のバランスをより向上させる観点から、好ましくは１０質量％以上、より好ましくは１５質量％以上、さらに好ましくは１８質量％以上、さらにより好ましくは２０質量％以上、より一層好ましくは２５質量％以上であり、そして好ましくは４５質量％以下、より好ましくは４３質量％以下、さらに好ましくは４０質量％以下、さらにより好ましくは３５質量％以下である。
　また、本実施形態の可塑性油脂組成物の製造方法における油脂組成物の、グリセリン脂肪酸エステルの総脂肪酸中の多価不飽和脂肪酸（ＰＵＦＡ）含有量は、可塑性、保形性、取り扱い性および保存安定性のバランスをより向上させる観点から、好ましくは５質量％以上、より好ましくは１０質量％以上、さらに好ましくは１５質量％以上、さらにより好ましくは１８質量％以上、より一層好ましくは２０質量％以上、さらにより一層好ましくは２５質量％以上であり、そして好ましくは４５質量％以下、より好ましくは４３質量％以下、さらに好ましくは４０質量％以下、さらにより好ましくは３５質量％以下である。
　なお、多価不飽和脂肪酸とは、不飽和結合を２つ以上持つ不飽和脂肪酸を表す。 In the oil composition in the method for producing a plastic oil composition of this embodiment, the polyunsaturated fatty acid (PUFA) content in the total fatty acids of the glycerin fatty acid ester is, from the viewpoint of further improving the balance of plasticity, shape retention, handleability and storage stability, preferably 10 mass% or more, more preferably 15 mass% or more, even more preferably 18 mass% or more, even more preferably 20 mass% or more, even more preferably 25 mass% or more, and is preferably 45 mass% or less, more preferably 43 mass% or less, even more preferably 40 mass% or less, and even more preferably 35 mass% or less.
In addition, the polyunsaturated fatty acid (PUFA) content in the total fatty acids of the glycerin fatty acid ester of the oil composition in the manufacturing method for a plastic oil composition of this embodiment is, from the viewpoint of further improving the balance of plasticity, shape retention, handleability and storage stability, preferably 5 mass% or more, more preferably 10 mass% or more, even more preferably 15 mass% or more, even more preferably 18 mass% or more, even more preferably 20 mass% or more, even even more preferably 25 mass% or more, and is preferably 45 mass% or less, more preferably 43 mass% or less, even more preferably 40 mass% or less, and even more preferably 35 mass% or less.
The polyunsaturated fatty acid refers to an unsaturated fatty acid having two or more unsaturated bonds.
　本実施形態の可塑性油脂組成物の製造方法において、油脂組成物を含む原料を混合する工程は、油脂組成物を含む油相成分に水を含む水相成分を加える工程をさらに含んでもよい。
　水相成分を添加する工程を含む場合、乳化する工程を含むことが好ましい。乳化する工程は、例えば５０℃以上８０℃以下の温度で攪拌することにより行うことができる。また、乳化する工程および後述の急冷練り合わせする工程を適性に行うため、油相成分および水相成分を混合する前にそれぞれ、５０℃以上８０℃以下の温度に加温することが好ましい。 In the method for producing a plastic oil or fat composition of this embodiment, the step of mixing the raw materials containing the oil or fat composition may further include a step of adding an aqueous phase component containing water to the oil phase component containing the oil or fat composition.
When the process includes a step of adding an aqueous phase component, it is preferable to include an emulsifying step. The emulsifying step can be carried out by stirring at a temperature of 50° C. to 80° C., for example. In order to appropriately carry out the emulsifying step and the quenching kneading step described below, it is preferable to heat the oil phase component and the aqueous phase component to a temperature of 50° C. to 80° C. before mixing them.
　本実施形態の可塑性油脂組成物の製造方法は、油脂組成物を含む原料を混合する工程の後に、油脂組成物を急冷練り合わせする工程をさらに含んでもよい。
　急冷練り合わせする工程は、油脂組成物または油脂組成物を含む油脂原料を可塑化し、可塑性油脂組成物とする工程である。急冷練り合わせする方法に制限はないが、例えば、パーフェクター、コンビネーター、ボテーター、ネクサス等の冷却混合機で急冷しながら混和することにより行うことができる。 The method for producing a plastic oil and fat composition of the present embodiment may further include a step of quenching and kneading the oil and fat composition after the step of mixing the raw materials containing the oil and fat composition.
The quenching and kneading process is a process of plasticizing the oil and fat composition or the oil and fat raw material containing the oil and fat composition to obtain a plastic oil and fat composition. There is no limitation on the method of quenching and kneading, but it can be performed, for example, by mixing while quenching with a cooling mixer such as a perfector, a combinator, a votator, or a nexus.
　本実施形態の可塑性油脂組成物の製造方法は、炭素数が１３以上１５以下である脂肪酸およびグリセリンを反応させてグリセリン脂肪酸エステルを製造する工程を含む。上記工程では、炭素数が１３以上１５以下である脂肪酸を任意の含有量で配合してグリセリン脂肪酸エステルを製造することにより、食品調製用油脂組成物全体の脂肪酸組成を任意の組成に調整することが可能である。炭素数が１３以上１５以下である脂肪酸としては、市販の食品添加物や試薬を用いることができるほか、天然の動植物油を鹸化して得られる脂肪酸や、それら脂肪酸を必要に応じて分子蒸留して得られた脂肪酸を用いることができる。天然の動植物油を用いて炭素数が１３以上１５以下である脂肪酸残基を含むグリセリン脂肪酸エステルを製造する場合、天然の動植物油が炭素数が１３以上１５以下の脂肪酸を含むとともに、炭素数が１２の脂肪酸を同時に含む場合があるため、炭素数が１３以上１５以下である脂肪酸を用いてグリセリン脂肪酸エステルを製造できることにより、グリセリン脂肪酸エステルの総脂肪酸中の、炭素数が１３以上１５以下の脂肪酸の含有量に対する炭素数が１２の脂肪酸の含有量の質量比を調整しやすくなる。 The method for producing a plastic oil composition of this embodiment includes a step of reacting a fatty acid having 13 to 15 carbon atoms with glycerin to produce a glycerin fatty acid ester. In the above step, by producing a glycerin fatty acid ester by blending a fatty acid having 13 to 15 carbon atoms at an arbitrary content, it is possible to adjust the fatty acid composition of the entire oil composition for food preparation to an arbitrary composition. As the fatty acid having 13 to 15 carbon atoms, commercially available food additives and reagents can be used, as well as fatty acids obtained by saponifying natural animal and vegetable oils, and fatty acids obtained by molecular distillation of such fatty acids as necessary. When producing a glycerin fatty acid ester containing a fatty acid residue having 13 to 15 carbon atoms using natural animal and vegetable oils, the natural animal and vegetable oils may contain fatty acids having 13 to 15 carbon atoms as well as fatty acids having 12 carbon atoms at the same time. Therefore, by being able to produce the glycerin fatty acid ester using fatty acids having 13 to 15 carbon atoms, it becomes easier to adjust the mass ratio of the content of fatty acids having 12 carbon atoms to the content of fatty acids having 13 to 15 carbon atoms in the total fatty acids of the glycerin fatty acid ester.
　また、本実施形態の可塑性油脂組成物の製造方法は、上記のように得られたグリセリン脂肪酸エステルと、上記グリセリン脂肪酸エステル以外のグリセリン脂肪酸エステルを含む食用油脂とをエステル交換する工程をさらに含んでもよい。これにより、可塑性および保形性のバランスをより向上できる。
　また、炭素数が１３以上１５以下である脂肪酸およびグリセリンを反応させてグリセリン脂肪酸エステルを製造する工程および、上記のように得られたグリセリン脂肪酸エステルと、上記グリセリン脂肪酸エステル以外のグリセリン脂肪酸エステルを含む食用油脂とをエステル交換する工程は、油脂組成物を含む原料を混合する工程の前に行われることが好ましい。 The method for producing a plastic oil composition of the present embodiment may further include a step of transesterifying the glycerin fatty acid ester obtained as described above with an edible oil containing a glycerin fatty acid ester other than the above glycerin fatty acid ester, thereby further improving the balance between plasticity and shape retention.
In addition, the step of producing a glycerol fatty acid ester by reacting a fatty acid having a carbon number of 13 to 15 with glycerin, and the step of transesterifying the glycerol fatty acid ester obtained as described above with an edible fat or oil containing a glycerol fatty acid ester other than the glycerol fatty acid ester are preferably performed before the step of mixing a raw material containing an oil and fat composition.
　本実施形態の可塑性油脂組成物の製造方法が、上記グリセリン脂肪酸エステルと、上記グリセリン脂肪酸エステル以外のグリセリン脂肪酸エステルを含む食用油脂とをエステル交換する工程を含む場合、上記グリセリン脂肪酸エステル以外のグリセリン脂肪酸エステルを含む食用油脂については特に制限されない。例えば、菜種油、大豆油、コーン油、ゴマ油、ヤシ油、パーム油、パーム核油、米油、綿実油、紅花油、ヒマワリ油、オリーブ油、亜麻仁油、落花生油、サル脂、カカオ脂、シア脂などの植物油脂；牛脂、豚脂、鶏脂、乳脂、魚油などの動物油脂；及び中鎖脂肪酸トリグリセリドなどの合成油脂が挙げられる。好ましくは植物油脂であり、より好ましくは菜種油、大豆油、パーム油、およびヒマワリ油からなる群から選択される１種又は２種以上である。また、上記油脂に分別、水素添加等の処理を施した加工油脂が挙げられる。これらの中でも、好ましくは植物油脂およびその加工油脂からなる群から選択される１種又は２種以上であり、より好ましくは菜種油、大豆油、パーム油、ヒマワリ油およびそれらの加工油脂からなる群から選択される１種又は２種以上である。 When the method for producing the plastic oil composition of this embodiment includes a step of transesterifying the above-mentioned glycerin fatty acid ester with an edible oil containing a glycerin fatty acid ester other than the above-mentioned glycerin fatty acid ester, the edible oil containing a glycerin fatty acid ester other than the above-mentioned glycerin fatty acid ester is not particularly limited. For example, vegetable oils and fats such as rapeseed oil, soybean oil, corn oil, sesame oil, coconut oil, palm oil, palm kernel oil, rice oil, cottonseed oil, safflower oil, sunflower oil, olive oil, linseed oil, peanut oil, monkey fat, cacao butter, shea butter, etc.; animal oils and fats such as beef tallow, lard, chicken fat, milk fat, and fish oil; and synthetic oils and fats such as medium-chain fatty acid triglycerides. Vegetable oils and fats are preferred, and one or more selected from the group consisting of rapeseed oil, soybean oil, palm oil, and sunflower oil are more preferred. In addition, processed oils and fats obtained by subjecting the above-mentioned oils and fats to treatments such as fractionation and hydrogenation can be included. Among these, one or more types selected from the group consisting of vegetable oils and fats and processed oils and fats thereof are preferred, and one or more types selected from the group consisting of rapeseed oil, soybean oil, palm oil, sunflower oil and processed oils and fats thereof are more preferred.
　エステル交換油の製造方法において、エステル交換は公知の方法によって行うことができる。エステル交換の方法は、ランダムエステル交換でも、グリセロールの１、３位に結合した脂肪酸に特異的なエステル交換でもよいが、ランダムエステル交換が好ましい。また、エステル交換に用いる触媒としてはナトリウムメトキシド等の化学触媒やリパーゼ等の酵素触媒等が挙げられる。
　エステル交換油の製造方法は、例えば下記の方法で行うことができる。
　得られたグリセリン脂肪酸エステルと、上記グリセリン脂肪酸エステル以外のグリセリン脂肪酸エステルを含む食用油脂とを混合した混合油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２．０ｋＰａ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行う。ランダムエステル交換反応後、水洗して触媒を除去する。水洗後、活性白土を用いて脱色処理をおこない、更に脱臭処理をおこなって各エステル交換油を得る。 In the method for producing interesterified oil, interesterification can be carried out by a known method. The interesterification method may be random interesterification or specific interesterification of fatty acids bonded to the 1- and 3-positions of glycerol, but random interesterification is preferred. Examples of catalysts used for interesterification include chemical catalysts such as sodium methoxide and enzyme catalysts such as lipase.
The transesterified oil can be produced, for example, by the following method.
The resulting glycerol fatty acid ester is mixed with edible fats and oils containing glycerol fatty acid esters other than the above glycerol fatty acid esters, and 0.3 parts by mass of sodium methoxide is added as a catalyst to 100 parts by mass of the mixed oil, and a random transesterification reaction is carried out while stirring for 60 minutes under conditions of 80°C and a vacuum degree of 2.0 kPa. After the random transesterification reaction, the catalyst is removed by washing with water. After washing with water, decolorization treatment is carried out using activated clay, and further deodorization treatment is carried out to obtain each transesterification oil.
　本実施形態の可塑性油脂組成物は、油脂を含む油相と水を含む水相とを油中水型に乳化した油中水型可塑性油脂組成物であってもよいし、水分が０．５質量％以下であるショートニングであってもよいが、油中水型可塑性油脂組成物であることが好ましい。油中水型可塑性油脂組成物の例としては、ファットスプレッドやマーガリン等が挙げられる。
　油中水型可塑性油脂組成物の場合、油相の含有量は、好ましくは５０質量％以上、より好ましくは６０質量％以上、さらに好ましくは７０質量％以上、さらにより好ましくは７５質量％以上であり、そして好ましくは９９．４質量％以下、より好ましくは９８質量％以下、さらに好ましくは９０質量％以下、さらにより好ましくは８５質量％以下である。水相の含有量は、好ましくは０．６質量％以上、より好ましくは２質量％以上、さらに好ましくは１０質量％以上、さらにより好ましくは１５質量％以上であり、そして好ましくは５０質量％以下、より好ましくは４０質量％以下、さらに好ましくは３０質量％以下、さらにより好ましくは２５質量％以下である。 The plastic oil composition of the present embodiment may be a water-in-oil type plastic oil composition in which an oil phase containing oils and an aqueous phase containing water are emulsified into a water-in-oil type, or may be shortening having a water content of 0.5 mass % or less, but is preferably a water-in-oil type plastic oil composition. Examples of the water-in-oil type plastic oil composition include fat spreads and margarine.
In the case of a water-in-oil type plastic fat composition, the content of the oil phase is preferably 50% by mass or more, more preferably 60% by mass or more, even more preferably 70% by mass or more, even more preferably 75% by mass or more, and preferably 99.4% by mass or less, more preferably 98% by mass or less, even more preferably 90% by mass or less, even more preferably 85% by mass or less. The content of the water phase is preferably 0.6% by mass or more, more preferably 2% by mass or more, even more preferably 10% by mass or more, even more preferably 15% by mass or more, and preferably 50% by mass or less, more preferably 40% by mass or less, even more preferably 30% by mass or less, even more preferably 25% by mass or less.
　本実施形態の可塑性油脂組成物は、本発明の効果を損なわない範囲において油脂と水以外に従来の公知の成分を含んでもよい。公知の成分としては、特に制限されないが、例えば乳、乳製品、蛋白質、糖質、塩類、酸味料、ｐＨ調整剤、抗酸化剤、香辛料、着色成分、香料、乳化剤等が挙げられる。乳としては、牛乳等が挙げられる。乳製品としては、脱脂乳、クリーム、チーズ（ナチュラルチーズ、プロセスチーズ等）、発酵乳、濃縮乳、脱脂濃縮乳、無糖れん乳、加糖れん乳、無糖脱脂れん乳、加糖脱脂れん乳、全粉乳、脱脂粉乳、クリームパウダー、ホエイパウダー、蛋白濃縮ホエイパウダー、ホエイ蛋白コンセントレート、ホエイ蛋白アイソレート、バターミルクパウダー、トータルミルクプロテイン、カゼインナトリウム、カゼインカリウム等が挙げられる。蛋白質としては、大豆蛋白質、エンドウ豆蛋白質、小麦蛋白質等の植物蛋白質等が挙げられる。糖質としては、単糖（グルコース、フルクトース、ガラクトース、マンノース等）、二糖類（ラクトース、スクロース、マルトース、トレハロース等）、オリゴ糖、糖アルコール、デンプン、デンプン分解物、多糖類等が挙げられる。抗酸化剤としては、Ｌ－アスコルビン酸、Ｌ－アスコルビン酸誘導体、トコフェロール、トコトリエノール、リグナン、ユビキノン類、キサンチン類、オリザノール、植物ステロール、カテキン類、ポリフェノール類、茶抽出物等が挙げられる。香辛料としては、カプサイシン、アネトール、オイゲノール、シネオール、ジンゲロン等が挙げられる。着色成分としては、カロテン、アナトー、アスタキサンチン等が挙げられる。香料としては、バターフレーバー、ミルクフレーバー等が挙げられる。乳化剤としては、レシチン、ソルビタン脂肪酸エステル、ポリグリセリン脂肪酸エステル、モノグリセリン脂肪酸エステル、有機酸グリセリン脂肪酸エステル、ショ糖脂肪酸エステル、ポリグリセリン縮合リシノレイン酸エステル、プロピレングリコール脂肪酸エステル、ステアロイル乳酸カルシウム、ステアロイル乳酸ナトリウム、ポリオキシエチレンソルビタン脂肪酸エステル等が挙げられる。 The plastic oil composition of this embodiment may contain conventional known ingredients other than the oil and water, as long as the effect of the present invention is not impaired. Known ingredients include, but are not limited to, milk, dairy products, proteins, carbohydrates, salts, acidulants, pH adjusters, antioxidants, spices, coloring ingredients, flavorings, emulsifiers, etc. Milk includes cow's milk, etc. Dairy products include skim milk, cream, cheese (natural cheese, processed cheese, etc.), fermented milk, concentrated milk, skim concentrated milk, unsweetened condensed milk, sweetened condensed milk, unsweetened condensed skim milk, sweetened condensed skim milk, whole milk powder, skim milk powder, cream powder, whey powder, protein concentrated whey powder, whey protein concentrate, whey protein isolate, buttermilk powder, total milk protein, sodium caseinate, potassium caseinate, etc. Proteins include plant proteins such as soy protein, pea protein, wheat protein, etc. Examples of carbohydrates include monosaccharides (glucose, fructose, galactose, mannose, etc.), disaccharides (lactose, sucrose, maltose, trehalose, etc.), oligosaccharides, sugar alcohols, starch, starch hydrolysates, polysaccharides, etc. Examples of antioxidants include L-ascorbic acid, L-ascorbic acid derivatives, tocopherol, tocotrienol, lignan, ubiquinones, xanthins, oryzanol, plant sterols, catechins, polyphenols, tea extracts, etc. Examples of spices include capsaicin, anethole, eugenol, cineole, zingerone, etc. Examples of coloring components include carotene, annatto, astaxanthin, etc. Examples of flavorings include butter flavor, milk flavor, etc. Emulsifiers include lecithin, sorbitan fatty acid esters, polyglycerin fatty acid esters, monoglycerin fatty acid esters, organic acid glycerin fatty acid esters, sucrose fatty acid esters, polyglycerin condensed ricinoleic acid esters, propylene glycol fatty acid esters, calcium stearoyl lactylate, sodium stearoyl lactylate, polyoxyethylene sorbitan fatty acid esters, etc.
　本実施形態の食品の製造方法は、本実施形態の可塑性油脂組成物の製造方法で得られた可塑性油脂組成物を含む原材料を用いて食品を調製する工程を含む。
　可塑性油脂組成物を含む原材料を用いて食品を調製する工程は制限されないが、例えば本実施形態の可塑性油脂組成物を、他の原材料、例えば粉類、調味料、香料、乳化剤等と混合し、加熱調理する方法；本実施形態の可塑性油脂組成物を、パン類、ケーキ類、焼き菓子類等に載せる方法；本実施形態の可塑性油脂組成物を、麺類、米類、肉類、魚類、野菜類等を加熱調理したものに和える方法等が挙げられる。
　また、可塑性油脂組成物を含む原材料を用いて食品を調製する工程として、例えば、本実施形態の可塑性油脂組成物を、麺類、米類、肉類、魚類、野菜類、卵類等の炒め油、フライ油等として使用する方法等が挙げられる。
　食品としては制限されないが、食パン、ロールパン、菓子パン、調理パン、シュトーレン、パネトーネ、ブリオッシュなどのパン類；デニッシュ、クロワッサン、パイなどのペストリー；パウンドケーキ、スポンジケーキ、ホットケーキなどのケーキ類；ビスケット、クッキー、焼きドーナツ、ブッセ、ワッフルなどの焼き菓子類；肉類、魚介類、野菜等のソテー；オムレツ等の卵加工食品；スパゲティ、ペンネ等の麺類；ピラフ、ドリア等のご飯類；牛乳、豆乳、乳飲料、乳酸飲料、清涼飲料、茶、コーヒー等の飲料等が挙げられる。
　本実施形態の食品の製造方法は、本実施形態の可塑性油脂組成物の製造方法により製造された可塑性油脂組成物を用いるため、可塑性および保形性のバランスに優れ、食品の製造に好適に用いることができる。 The method for producing a food product of this embodiment includes a step of preparing a food product using a raw material containing the plastic oil-and-fat composition obtained by the method for producing a plastic oil-and-fat composition of this embodiment.
The process for preparing food using raw materials containing the plastic oil composition is not limited, and examples thereof include a method of mixing the plastic oil composition of this embodiment with other raw materials, such as flour, seasonings, fragrances, emulsifiers, etc., and cooking with heat; a method of placing the plastic oil composition of this embodiment on bread, cakes, baked goods, etc.; a method of mixing the plastic oil composition of this embodiment with noodles, rice, meat, fish, vegetables, etc. that have been cooked with heat; and the like.
Furthermore, as a process for preparing food using raw materials containing the plastic oil composition, for example, a method of using the plastic oil composition of this embodiment as a stir-frying oil or frying oil for noodles, rice, meat, fish, vegetables, eggs, etc. can be mentioned.
Food products include, but are not limited to, breads such as bread, rolls, sweet buns, cooked bread, stollen, panettone, brioche, etc.; pastries such as Danish, croissants, pies, etc.; cakes such as pound cake, sponge cake, pancake, etc.; baked goods such as biscuits, cookies, baked donuts, bushés, waffles, etc.; sauteed meat, seafood, vegetables, etc.; processed egg foods such as omelets, etc.; noodles such as spaghetti, penne, etc.; rice dishes such as pilaf, doria, etc.; beverages such as milk, soy milk, milk drinks, lactic acid drinks, soft drinks, tea, coffee, etc.
The food manufacturing method of this embodiment uses a plastic oil composition produced by the plastic oil composition manufacturing method of this embodiment, and therefore has an excellent balance of plasticity and shape retention, making it suitable for use in food manufacturing.
　本実施形態の可塑性油脂組成物の風味の向上方法は、油脂組成物を含む原料を混合する工程を含み、油脂組成物が、炭素数が１３以上１５以下である脂肪酸残基を含むグリセリン脂肪酸エステルを含有し、グリセリン脂肪酸エステルの総脂肪酸中、炭素数が１３以上１５以下である脂肪酸を１．８質量％以上１００質量％以下含有し、グリセリン脂肪酸エステルの総脂肪酸中、炭素数が１２である脂肪酸の含有量が、炭素数が１３以上１５以下である脂肪酸の含有量に対する質量比で０以上２．５以下である。
　上記油脂組成物の詳細については、本実施形態の可塑性油脂組成物の製造方法の項で上述した通りであるため、省略する。
　このような本実施形態の可塑性油脂組成物の風味の向上方法によれば、可塑性油脂組成物の風味を向上することができる。中でも、可塑性油脂組成物に乳類や香料類を加えた場合に、それらの風味を向上することができる。 The method for improving the flavor of a plastic oil and fat composition of this embodiment includes a step of mixing a raw material containing the oil and fat composition, wherein the oil and fat composition contains a glycerin fatty acid ester containing a fatty acid residue having a carbon number of 13 or more and 15 or less, the total fatty acids in the glycerin fatty acid ester contain fatty acids having a carbon number of 13 or more and 15 or less at 1.8% by mass or more and 100% by mass or less, and the content of fatty acids having a carbon number of 12 in the total fatty acids in the glycerin fatty acid ester is a mass ratio of 0 to 2.5 relative to the content of fatty acids having a carbon number of 13 or more and 15 or less.
Details of the oil composition are as described above in the section on the method for producing the plastic oil composition of this embodiment, and therefore will be omitted here.
According to the method for improving the flavor of a plastic oil composition of the present embodiment, the flavor of the plastic oil composition can be improved. In particular, when dairy products or flavorings are added to the plastic oil composition, the flavor of the dairy products or flavorings can be improved.
　以上、本発明の実施形態について述べたが、これらは本発明の例示であり、上記以外の様々な構成を採用することもできる。
　また、本発明は前述の実施形態に限定されるものではなく、本発明の目的を達成できる範囲での変形、改良等は本発明に含まれるものである。 Although the embodiments of the present invention have been described above, these are merely examples of the present invention, and various configurations other than those described above can also be adopted.
Furthermore, the present invention is not limited to the above-described embodiment, and modifications and improvements within the scope of the present invention that can achieve the object of the present invention are included in the present invention.
　以下、参考形態の例を付記する。
［１］
　油脂組成物を含む原料を混合する工程を含む、可塑性油脂組成物の製造方法であって、
　前記油脂組成物が、炭素数が１３以上１５以下である脂肪酸残基を含むグリセリン脂肪酸エステルを含有し、
　前記グリセリン脂肪酸エステルの総脂肪酸中、炭素数が１３以上１５以下である脂肪酸を１．８質量％以上１００質量％以下含有し、
　前記グリセリン脂肪酸エステルの総脂肪酸中、炭素数が１２である脂肪酸の含有量が、前記炭素数が１３以上１５以下である脂肪酸の含有量に対する質量比で０以上２．５以下である、可塑性油脂組成物の製造方法。
［２］
　前記炭素数が１３以上１５以下である脂肪酸が、トリデカン酸、テトラデカン酸およびペンタデカン酸からなる群から選択される１種または２種以上を含む、［１］に記載の可塑性油脂組成物の製造方法。
［３］
　前記グリセリン脂肪酸エステルの総脂肪酸中、炭素数が１２である脂肪酸の含有量が、０質量％以上１５質量％以下である、［１］または［２］に記載の可塑性油脂組成物の製造方法。
［４］
　前記グリセリン脂肪酸エステルの総脂肪酸中、炭素数が１４である脂肪酸の含有量が、１．０質量％以上１００質量％以下である、［１］または［２］に記載の可塑性油脂組成物の製造方法。
［５］
　前記グリセリン脂肪酸エステルがエステル交換油を含む、［１］または［２］に記載の可塑性油脂組成物の製造方法。
［６］
　前記油脂組成物のヨウ素価が、６０以上１１０以下である、［１］または［２］に記載の可塑性油脂組成物の製造方法。
［７］
　炭素数が１３以上１５以下である脂肪酸およびグリセリンを反応させてグリセリン脂肪酸エステルを製造する工程を含む、［１］または［２］に記載の可塑性油脂組成物の製造方法。
［８］
　炭素数が１３以上１５以下である前記脂肪酸および前記グリセリンを反応させて得られる前記グリセリン脂肪酸エステルと、前記グリセリン脂肪酸エステル以外のグリセリン脂肪酸エステルを含む食用油脂とをエステル交換する工程をさらに含む、［７］に記載の可塑性油脂組成物の製造方法。
［９］
　［１］または［２］に記載の可塑性油脂組成物の製造方法で得られた可塑性油脂組成物を含む原材料を用いて食品を調製する工程を含む、食品の製造方法。
［１０］
　油脂組成物を含む原料を混合する工程を含む、可塑性油脂組成物の風味の向上方法であって、
　前記油脂組成物が、炭素数が１３以上１５以下である脂肪酸残基を含むグリセリン脂肪酸エステルを含有し、
　前記グリセリン脂肪酸エステルの総脂肪酸中、炭素数が１３以上１５以下である脂肪酸を１．８質量％以上１００質量％以下含有し、
　前記グリセリン脂肪酸エステルの総脂肪酸中、炭素数が１２である脂肪酸の含有量が、前記炭素数が１３以上１５以下である脂肪酸の含有量に対する質量比で０以上２．５以下である、可塑性油脂組成物の風味の向上方法。 Below, examples of reference forms are given.
[1]
A method for producing a plastic oil composition, comprising a step of mixing a raw material containing an oil composition,
The oil and fat composition contains a glycerin fatty acid ester containing a fatty acid residue having a carbon number of 13 to 15,
The glycerin fatty acid ester contains 1.8% by mass or more and 100% by mass or less of fatty acids having 13 or more and 15 or less carbon atoms in the total fatty acids of the glycerin fatty acid ester,
A method for producing a plastic oil composition, wherein the content of fatty acids having 12 carbon atoms in the total fatty acids of the glycerin fatty acid ester is in a mass ratio of 0 to 2.5 relative to the content of fatty acids having 13 to 15 carbon atoms.
[2]
The method for producing a plastic oil composition described in [1], wherein the fatty acid having 13 or more and 15 or less carbon atoms includes one or more selected from the group consisting of tridecanoic acid, tetradecanoic acid, and pentadecanoic acid.
[3]
A method for producing a plastic oil composition according to [1] or [2], wherein the content of fatty acids having 12 carbon atoms in the total fatty acids of the glycerin fatty acid ester is 0% by mass or more and 15% by mass or less.
[4]
A method for producing a plastic oil composition according to [1] or [2], wherein the content of fatty acids having 14 carbon atoms in the total fatty acids of the glycerin fatty acid ester is 1.0% by mass or more and 100% by mass or less.
[5]
The method for producing a plastic oil composition according to [1] or [2], wherein the glycerin fatty acid ester contains an interesterified oil.
[6]
The method for producing a plastic oil composition according to [1] or [2], wherein the iodine value of the oil composition is 60 or more and 110 or less.
[7]
A method for producing a plastic oil composition according to [1] or [2], comprising a step of producing a glycerin fatty acid ester by reacting a fatty acid having 13 to 15 carbon atoms with glycerin.
[8]
The method for producing a plastic oil composition according to [7] further comprises a step of transesterifying the glycerin fatty acid ester obtained by reacting the fatty acid having a carbon number of 13 to 15 and the glycerin with an edible oil containing a glycerin fatty acid ester other than the glycerin fatty acid ester.
[9]
A method for producing a food product, comprising a step of preparing a food product using a raw material containing a plastic oil composition obtained by the method for producing a plastic oil composition described in [1] or [2].
[10]
A method for improving the flavor of a plastic oil-and-fat composition, comprising a step of mixing a raw material containing an oil-and-fat composition,
The oil and fat composition contains a glycerin fatty acid ester containing a fatty acid residue having a carbon number of 13 to 15,
The glycerin fatty acid ester contains 1.8% by mass or more and 100% by mass or less of fatty acids having 13 or more and 15 or less carbon atoms in the total fatty acids of the glycerin fatty acid ester,
A method for improving the flavor of a plastic oil composition, wherein the content of fatty acids having 12 carbon atoms in the total fatty acids of the glycerin fatty acid ester is in a mass ratio of 0 to 2.5 relative to the content of fatty acids having 13 to 15 carbon atoms.
　以下に本発明の実施例を示すが、本発明の趣旨はこれらに限定されるものではない。
　以下の例において、特に断りのない場合、配合の単位は質量部である。 Examples of the present invention will be described below, but the gist of the present invention is not limited to these.
In the following examples, unless otherwise specified, the units of blending are parts by mass.
　油脂の原材料は以下のものを使用した。各例の油脂については、表４に従い配合した。またエステル交換油については、表１の配合に従い、下記＜エステル交換油の製造方法＞に従い、製造した。
・大豆油：大豆白絞油ＮＳ、株式会社Ｊ－オイルミルズ製
・菜種油：ＡＪＩＮＯＭＯＴＯさらさらキャノーラ油、株式会社J-オイルミルズ製
・パーム油：株式会社Ｊ－オイルミルズ製
・パームオレイン：パームオレインＩＶ６７、株式会社Ｊ－オイルミルズ製
・パームステアリン：株式会社Ｊ－オイルミルズ製
・トリテトラデカン酸グリセリル：製造例１のものを用いた
・トリトリデカン酸グリセリル：製造例１のものを用いた
・トリペンタデカン酸グリセリル：製造例１のものを用いた
・パーム核油：不二製油株式会社製
・ＭＣＴ：ＭＣＴ－１、株式会社Ｊ－オイルミルズ製 The raw materials for the fats and oils used were as follows. The fats and oils in each example were blended according to Table 4. The interesterified oil was produced according to the blend in Table 1 and the method for producing interesterified oil described below.
Soybean oil: Soybean white refined oil NS, manufactured by J-Oil Mills Co., Ltd. Rapeseed oil: AJINOMOTO smooth canola oil, manufactured by J-Oil Mills Co., Ltd. Palm oil: manufactured by J-Oil Mills Co., Ltd. Palm olein: Palm olein IV67, manufactured by J-Oil Mills Co., Ltd. Palm stearin: manufactured by J-Oil Mills Co., Ltd. Glyceryl tritetradecanoate: The one used in Production Example 1 Glyceryl tritridecanoate: The one used in Production Example 1 Glyceryl tripentadecanoate: The one used in Production Example 1 Palm kernel oil: manufactured by Fuji Oil Co., Ltd. MCT: MCT-1, manufactured by J-Oil Mills Co., Ltd.
（製造例１：トリテトラデカン酸グリセリル、トリトリデカン酸グリセリルおよびトリペンタデカン酸グリセリルの製造方法）
　ミリスチン酸（テトラデカン酸）（富士フイルム和光純薬製）８９．７質量部及びグリセリン（富士フイルム和光純薬製）１０．３質量部を混合したものに対して、触媒として水酸化ナトリウムを０．１質量部添加し、２２０℃、大気圧の条件で窒素を吹き込みながら２４０分間撹拌することでエステル合成反応を行った。エステル合成反応後、水酸化ナトリウム水溶液を添加して脱酸を行い、未反応のテトラデカン酸を取り除いた。脱酸後、活性白土を用いて脱色処理をおこない、更に脱臭処理をおこなってトリテトラデカン酸グリセリルを得た。
　トリトリデカン酸グリセリルおよびトリペンタデカン酸グリセリルについては、上記トリテトラデカン酸グリセリルの製造方法において、テトラデカン酸をそれぞれトリデカン酸（東京化成工業株式会社製）またはペンタデカン酸（東京化成工業株式会社製）に変更した以外は、トリテトラデカン酸グリセリルの製造方法と同様に行った。 (Production Example 1: Method for producing glyceryl tritetradecanoate, glyceryl tritridecanoate, and glyceryl tripentadecanoate)
0.1 parts by mass of sodium hydroxide was added as a catalyst to a mixture of 89.7 parts by mass of myristic acid (tetradecanoic acid) (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) and 10.3 parts by mass of glycerin (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), and the mixture was stirred for 240 minutes while blowing in nitrogen at 220° C. and atmospheric pressure to carry out an ester synthesis reaction. After the ester synthesis reaction, an aqueous sodium hydroxide solution was added to carry out deacidification, and unreacted tetradecanoic acid was removed. After deacidification, the mixture was decolorized using activated clay, and further deodorized to obtain glyceryl tritetradecanoate.
For glyceryl tritridecanoate and glyceryl tripentadecanoate, the same production method as for glyceryl tritetradecanoate was carried out, except that tetradecanoic acid was changed to tridecanoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) or pentadecanoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), respectively.
＜エステル交換油の製造方法＞
　表１のエステル交換油配合（単位は質量部とする）に従い、各油脂を配合し、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２．０ｋＰａ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行った。ランダムエステル交換反応後、水洗して触媒を除去した。水洗後、活性白土を用いて脱色処理をおこない、更に脱臭処理をおこなって各エステル交換油を得た。 <Method of producing interesterified oil>
According to the transesterified oil composition (unit: parts by mass) in Table 1, each oil was blended, and 0.3 parts by mass of sodium methoxide was added as a catalyst to 100 parts by mass of the oil, and a random transesterification reaction was carried out while stirring for 60 minutes under conditions of 80°C and a vacuum degree of 2.0 kPa. After the random transesterification reaction, the catalyst was removed by washing with water. After washing with water, decolorization treatment was carried out using activated clay, and further deodorization treatment was carried out to obtain each transesterified oil.
Figure JPOXMLDOC01-appb-T000001
Figure JPOXMLDOC01-appb-T000001
＜グリセリン脂肪酸エステル中の脂肪酸含有量の分析＞
　各例の油脂を三フッ化ホウ素メタノール法にて脂肪酸メチルエステルとした後、下記の条件にて、ガスクロマトグラフィー（ＧＣ）法で脂肪酸組成を分析し、各脂肪酸の脂肪酸全体における含有量（質量％）を算出した。なお、表中、例えば「Ｃ１２：０」は、炭素数１２、不飽和結合０の脂肪酸を表し、「Ｃ１８：１」は、炭素数１８、不飽和結合１の脂肪酸を表す。また得られた結果から、グリセリン脂肪酸エステルの総脂肪酸中の、炭素数が１３以上１５以下である脂肪酸の含有量、炭素数が１３以上１５以下である脂肪酸の含有量に対する炭素数が１２である脂肪酸の含有量の質量比、炭素数が１８の不飽和脂肪酸、飽和脂肪酸（ＳＦＡ）の含有量、多価不飽和脂肪酸（ＰＵＦＡ）の含有量を算出した。結果を表４および表５に示す。
・ＧＣ装置：製品名ＧＣ２０１０（（株）島津製作所製）
・カラム：ＳＰ－２５６０（１００ｍ×０．２５ｍｍ×０．２μｍ）（スペルコ社製）
・注入口温度：２５０℃
・キャリアガス：ヘリウム（２９．１ｍｌ／ｍｉｎ）
・スプリット比：２５：１
・カラム温度：１８０℃５５ｍｉｎ→（８℃／ｍｉｎ）→２２０℃５ｍｉｎ
・検出器：水素炎イオン検出器（２６０℃） <Analysis of fatty acid content in glycerin fatty acid esters>
The fats and oils of each example were converted into fatty acid methyl esters by the boron trifluoride methanol method, and the fatty acid composition was analyzed by gas chromatography (GC) under the following conditions, and the content (mass%) of each fatty acid in the total fatty acids was calculated. In the table, for example, "C12:0" represents a fatty acid with 12 carbon atoms and 0 unsaturated bonds, and "C18:1" represents a fatty acid with 18 carbon atoms and 1 unsaturated bond. From the results obtained, the content of fatty acids with 13 to 15 carbon atoms in the total fatty acids of the glycerin fatty acid ester, the mass ratio of the content of fatty acids with 12 carbon atoms to the content of fatty acids with 13 to 15 carbon atoms, the content of unsaturated fatty acids with 18 carbon atoms, the content of saturated fatty acids (SFA), and the content of polyunsaturated fatty acids (PUFA) were calculated. The results are shown in Tables 4 and 5.
・GC device: Product name GC2010 (manufactured by Shimadzu Corporation)
Column: SP-2560 (100 m x 0.25 mm x 0.2 μm) (manufactured by Sperco)
・Inlet temperature: 250℃
Carrier gas: Helium (29.1 ml/min)
Split ratio: 25:1
Column temperature: 180°C 55min → (8°C/min) → 220°C 5min
Detector: Hydrogen flame ion detector (260°C)
＜ヨウ素価＞
　各例の油脂について、ヨウ素価は「基準油脂分析試験法２．３．４．１－１９９６ヨウ素価（ウィイス－シクロヘキサン法）」（日本油化学会）に則って測定した。 <Iodine value>
The iodine value of each of the fats and oils was measured in accordance with "Standard Methods for the Analysis of Fats, Oils and Oils 2.3.4.1-1996 Iodine Value (Wiess-Cyclohexane Method)" (Japan Oil Chemists' Society).
＜マーガリン評価＞
　各例で得られた油脂をミキシングタンクに入れ、６５℃にて加熱攪拌した。次いで、表２に記載の配合に従い、バター香料および着色料をミキシングタンクに加えて混合した。次いで、表２に記載の配合に従い、６５℃に加熱した水、脱脂粉乳（森永乳業株式会社製）をミキシングタンクに加え、６５℃に保ったまま攪拌を続けることで乳化液を得た。得られた乳化液をパーフェクターに通して急冷混捏し、マーガリンを得た。 <Margarine Evaluation>
The oils and fats obtained in each example were placed in a mixing tank and heated and stirred at 65°C. Next, according to the formulations shown in Table 2, butter flavoring and coloring were added to the mixing tank and mixed. Next, according to the formulations shown in Table 2, water heated to 65°C and skim milk powder (manufactured by Morinaga Milk Industry Co., Ltd.) were added to the mixing tank and stirred while maintaining the temperature at 65°C to obtain an emulsion. The obtained emulsion was passed through a perfecter to rapidly cool and knead, and margarine was obtained.
Figure JPOXMLDOC01-appb-T000002
Figure JPOXMLDOC01-appb-T000002
　得られたマーガリンについて、専門パネラー４名で喫食し、以下の評価基準に基づいて、可塑性、保形性および風味を評価した。可塑性については、マーガリンをスプーンで伸ばしたときの滑らかさを評価した。保形性については、マーガリンをスプーンに取って５分間室温で放置した後でも良好な硬さを維持できるかどうかを評価した。風味については、バター香料と脱脂粉乳の風味が強く感じられるかどうかを評価した。評点は、専門パネラーの合議にて決定した。
　実施例１－１～１－３については、比較例１を基準（３点）とし、実施例２－１～２－３については、比較例２を基準（３点）とした。結果を表４に示す。
（評価基準）
（可塑性）
５：非常に滑らかである
４：やや滑らかである
３：滑らかである
２：あまり滑らかでない
１：まったく滑らかでない
（保形性）
５：形状をしっかり維持できている
４：形状を維持できている
３：形状をやや維持できている
２：やや形が崩れている
１：形がくずれている
（風味）
５：バター香料と脱脂粉乳の風味が非常に強く感じられる
４：バター香料と脱脂粉乳の風味がやや強く感じられる
３：バター香料と脱脂粉乳の風味が感じられるが強くない
２：バター香料と脱脂粉乳の風味が弱い
１：バター香料と脱脂粉乳の風味がとても弱い The obtained margarines were tasted by four expert panelists and evaluated for plasticity, shape retention, and flavor based on the following evaluation criteria. For plasticity, the smoothness of the margarine when spread with a spoon was evaluated. For shape retention, the margarine was evaluated for its ability to maintain a good hardness even after being placed on a spoon and left at room temperature for 5 minutes. For flavor, the taste of butter flavor and skim milk powder was evaluated for its strong flavor. The scores were determined by consensus of the expert panelists.
For Examples 1-1 to 1-3, Comparative Example 1 was used as the standard (3 points), and for Examples 2-1 to 2-3, Comparative Example 2 was used as the standard (3 points). The results are shown in Table 4.
(Evaluation Criteria)
(Plasticity)
5: Very smooth 4: Somewhat smooth 3: Smooth 2: Not very smooth 1: Not smooth at all (shape retention)
5: The shape is well maintained 4: The shape is well maintained 3: The shape is somewhat well maintained 2: The shape is slightly distorted 1: The shape is distorted (flavor)
5: The flavor of butter flavor and skim milk powder is very strong 4: The flavor of butter flavor and skim milk powder is somewhat strong 3: The flavor of butter flavor and skim milk powder is felt but not strong 2: The flavor of butter flavor and skim milk powder is weak 1: The flavor of butter flavor and skim milk powder is very weak
＜クッキーの評価＞
　上記で得られたマーガリンを用いて、表３の配合に従い、下記のとおりクッキーを作製した。
１．ビーターを取り付けたホバートミキサーを用いて、油脂を中速１分３０秒ミキシングした。
２．ふるった上白糖、塩を添加し、中速１分３０秒ミキシングした。
３．水を添加し、中速１分３０秒ミキシングした。
４．粉を添加し、低速３０秒ミキシングし、クッキー生地を得た。
５．生地を２８０ｇずつに分割し、直径約４ｃｍ、長さ約３５ｃｍの棒状に成型した。
６．ペーパーで包んで冷蔵庫で１時間冷やした。
７．包丁で１ｃｍ幅の厚さにカットし、オーブンで焼成した（オーブンの上火の設定温度：１８０℃／オーブンの下火の設定温度：１８０℃、１５分）。 Cookie Rating
Using the margarine obtained above and according to the formulation in Table 3, cookies were made as follows.
1. The fats and oils were mixed using a Hobart mixer fitted with a beater at medium speed for 1 minute 30 seconds.
2. Add the sifted caster sugar and salt and mix at medium speed for 1 minute 30 seconds.
3. Add water and mix on medium speed for 1 minute 30 seconds.
4. The flour was added and mixed at low speed for 30 seconds to obtain a cookie dough.
5. The dough was divided into 280 g portions and shaped into log shapes with a diameter of approximately 4 cm and a length of approximately 35 cm.
6. Wrap it in paper and chill it in the refrigerator for an hour.
7. The mixture was cut into pieces 1 cm thick with a knife and baked in an oven (top oven temperature setting: 180° C./bottom oven temperature setting: 180° C., 15 minutes).
Figure JPOXMLDOC01-appb-T000003
Figure JPOXMLDOC01-appb-T000003
　得られたクッキーについて、専門パネラー４名で喫食し、以下の評価基準に基づいて、サクミおよび風味を評価した。実施例１－１～３は、比較例１を基準（３．０点）とし、実施例２－１～３は、比較例２を基準（３．０点）として評価した。
（評価基準）
（サクミ）
５：非常にサクサクしている
４：サクサクしている
３：ややサクサクしている
２：あまりサクサクしていない
１：まったくサクサクしていない
（風味）
５：油臭さがまったくなく、非常に良好な風味が感じられる
４：油臭さがほとんどなく、良好な風味が感じられる
３：油臭さが少しあるが、やや良好な風味が感じられる
２：油臭さが強く、良好な風味が感じられない
１：油臭さが非常に強く、良好な風味がまったく感じられない The obtained cookies were eaten by four expert panelists and evaluated for crispness and flavor based on the following evaluation criteria: Examples 1-1 to 1-3 were evaluated based on Comparative Example 1 (3.0 points), and Examples 2-1 to 2-3 were evaluated based on Comparative Example 2 (3.0 points).
(Evaluation Criteria)
(Sakumi)
5: Very crispy 4: Crispy 3: Slightly crispy 2: Not very crispy 1: Not at all crispy (flavor)
5: No oily smell at all, very good flavor 4: Almost no oily smell, good flavor 3: Slight oily smell, but some good flavor 2: Strong oily smell, no good flavor 1: Very strong oily smell, no good flavor
Figure JPOXMLDOC01-appb-T000004
Figure JPOXMLDOC01-appb-T000004
　表４の結果より、実施例で得られたマーガリンについては、比較例に対していずれも可塑性および保形性のバランスが良好で、さらに風味も良好であった。
また、実施例で得られたマーガリンを用いて作製したクッキーについては、比較例で得られたマーガリンを用いて作製したクッキーと比較して、サクミおよび風味の評価が同等若しくは良好であった。 As can be seen from the results in Table 4, the margarines obtained in the Examples had a better balance of plasticity and shape retention than the Comparative Examples, and also had a better flavor.
Furthermore, the cookies made using the margarines obtained in the Examples were evaluated as being equal to or better than the cookies made using the margarines obtained in the Comparative Examples in terms of crispness and flavor.
　また、比較例１’および実施例１－４～１－６について、実施例１－１～１－３および実施例２－１～２－３と同様に、マーガリン評価およびクッキーの評価を行った。実施例１－４～１－６については比較例１’を基準（３点）とした。なお、比較例１’は、上述した比較例１と同一の配合の油脂を用いて、実施例１－４～１－６と同時に評価した。結果を表５に示す。 In addition, margarine and cookie evaluations were performed for Comparative Example 1' and Examples 1-4 to 1-6 in the same manner as for Examples 1-1 to 1-3 and Examples 2-1 to 2-3. Comparative Example 1' was used as the standard (3 points) for Examples 1-4 to 1-6. Comparative Example 1' was evaluated simultaneously with Examples 1-4 to 1-6 using the same composition of fats and oils as in Comparative Example 1 described above. The results are shown in Table 5.
Figure JPOXMLDOC01-appb-T000005
Figure JPOXMLDOC01-appb-T000005
　表５の結果より、実施例１－４～１－６で得られたマーガリンについては、比較例１’に対していずれも可塑性が良好で、さらに風味も良好であった。 The results in Table 5 show that the margarines obtained in Examples 1-4 to 1-6 all had better plasticity and flavor than Comparative Example 1'.
　この出願は、２０２３年３月３０日に出願された日本出願特願２０２３－０５５８４６号を基礎とする優先権を主張し、その開示の全てをここに取り込む。 This application claims priority based on Japanese Patent Application No. 2023-055846, filed on March 30, 2023, the entire disclosure of which is incorporated herein by reference.

Claims (14)

  1. 　油脂組成物を含む原料を混合する工程を含む、可塑性油脂組成物の製造方法であって、
    　前記油脂組成物が、炭素数が１３以上１５以下である脂肪酸残基を含むグリセリン脂肪酸エステルを含有し、
    　前記グリセリン脂肪酸エステルの総脂肪酸中、炭素数が１３以上１５以下である脂肪酸を１．８質量％以上１００質量％以下含有し、
    　前記グリセリン脂肪酸エステルの総脂肪酸中、炭素数が１２である脂肪酸の含有量が、前記炭素数が１３以上１５以下である脂肪酸の含有量に対する質量比で０以上２．５以下である、可塑性油脂組成物の製造方法。     A method for producing a plastic oil composition, comprising a step of mixing a raw material containing an oil composition,
    The oil and fat composition contains a glycerin fatty acid ester containing a fatty acid residue having a carbon number of 13 to 15,
    The glycerin fatty acid ester contains 1.8% by mass or more and 100% by mass or less of fatty acids having 13 or more and 15 or less carbon atoms in the total fatty acids of the glycerin fatty acid ester,
    A method for producing a plastic oil composition, wherein the content of fatty acids having 12 carbon atoms in the total fatty acids of the glycerin fatty acid ester is in a mass ratio of 0 to 2.5 relative to the content of fatty acids having 13 to 15 carbon atoms.
  2. 　前記炭素数が１３以上１５以下である脂肪酸が、トリデカン酸、テトラデカン酸およびペンタデカン酸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に記載の可塑性油脂組成物の製造方法。 The method for producing a plastic oil composition according to claim 1, wherein the fatty acid having 13 to 15 carbon atoms includes one or more selected from the group consisting of tridecanoic acid, tetradecanoic acid, and pentadecanoic acid.
  3. 　前記グリセリン脂肪酸エステルの総脂肪酸中、炭素数が１２である脂肪酸の含有量が、０質量％以上１５質量％以下である、請求項１または２に記載の可塑性油脂組成物の製造方法。 The method for producing a plastic oil composition according to claim 1 or 2, wherein the content of fatty acids having 12 carbon atoms in the total fatty acids of the glycerin fatty acid ester is 0% by mass or more and 15% by mass or less.
  4. 　前記グリセリン脂肪酸エステルの総脂肪酸中、炭素数が１４である脂肪酸の含有量が、１．０質量％以上１００質量％以下である、請求項１または２に記載の可塑性油脂組成物の製造方法。 The method for producing a plastic oil composition according to claim 1 or 2, wherein the content of fatty acids having 14 carbon atoms in the total fatty acids of the glycerin fatty acid ester is 1.0% by mass or more and 100% by mass or less.
  5. 　前記グリセリン脂肪酸エステルの総脂肪酸中、飽和脂肪酸（ＳＦＡ）含有量が、２０質量％以上６５質量％以下である、請求項１または２に記載の可塑性油脂組成物の製造方法。 The method for producing a plastic oil composition according to claim 1 or 2, wherein the saturated fatty acid (SFA) content in the total fatty acids of the glycerin fatty acid ester is 20% by mass or more and 65% by mass or less.
  6. 　前記グリセリン脂肪酸エステルの総脂肪酸中、多価不飽和脂肪酸（ＰＵＦＡ）含有量が、５質量％以上４５質量％以下である、請求項１または２に記載の可塑性油脂組成物の製造方法。 The method for producing a plastic oil composition according to claim 1 or 2, wherein the polyunsaturated fatty acid (PUFA) content in the total fatty acids of the glycerin fatty acid ester is 5% by mass or more and 45% by mass or less.
  7. 　グリセリン脂肪酸エステルの総脂肪酸中、炭素数が１８の不飽和脂肪酸の含有量が、３１質量％以上９０質量％以下である、請求項１または２に記載の可塑性油脂組成物の製造方法。 The method for producing a plastic oil composition according to claim 1 or 2, wherein the content of unsaturated fatty acids having 18 carbon atoms in the total fatty acids of the glycerin fatty acid ester is 31% by mass or more and 90% by mass or less.
  8. 　前記グリセリン脂肪酸エステルがエステル交換油を含む、請求項１または２に記載の可塑性油脂組成物の製造方法。 The method for producing a plastic oil composition according to claim 1 or 2, wherein the glycerin fatty acid ester comprises an interesterified oil.
  9. 　前記油脂組成物のヨウ素価が、６０以上１１０以下である、請求項１または２に記載の可塑性油脂組成物の製造方法。 The method for producing a plastic oil composition according to claim 1 or 2, wherein the iodine value of the oil composition is 60 or more and 110 or less.
  10. 　前記油脂組成物のヨウ素価が、４０以上１１０以下である、請求項１または２に記載の可塑性油脂組成物の製造方法。 The method for producing a plastic oil composition according to claim 1 or 2, wherein the iodine value of the oil composition is 40 or more and 110 or less.
  11. 　炭素数が１３以上１５以下である脂肪酸およびグリセリンを反応させてグリセリン脂肪酸エステルを製造する工程を含む、請求項１または２に記載の可塑性油脂組成物の製造方法。 The method for producing the plastic oil composition according to claim 1 or 2, comprising the step of reacting a fatty acid having 13 to 15 carbon atoms with glycerin to produce a glycerin fatty acid ester.
  12. 　炭素数が１３以上１５以下である前記脂肪酸および前記グリセリンを反応させて得られる前記グリセリン脂肪酸エステルと、前記グリセリン脂肪酸エステル以外のグリセリン脂肪酸エステルを含む食用油脂とをエステル交換する工程をさらに含む、請求項１１に記載の可塑性油脂組成物の製造方法。 The method for producing a plastic oil composition according to claim 11 further comprises a step of transesterifying the glycerin fatty acid ester obtained by reacting the fatty acid having 13 to 15 carbon atoms with the glycerin, with an edible oil containing a glycerin fatty acid ester other than the glycerin fatty acid ester.
  13. 　請求項１または２に記載の可塑性油脂組成物の製造方法で得られた可塑性油脂組成物を含む原材料を用いて食品を調製する工程を含む、食品の製造方法。 A method for producing food, comprising the step of preparing food using a raw material containing a plastic oil composition obtained by the method for producing a plastic oil composition according to claim 1 or 2.
  14. 　油脂組成物を含む原料を混合する工程を含む、可塑性油脂組成物の風味の向上方法であって、
    　前記油脂組成物が、炭素数が１３以上１５以下である脂肪酸残基を含むグリセリン脂肪酸エステルを含有し、
    　前記グリセリン脂肪酸エステルの総脂肪酸中、炭素数が１３以上１５以下である脂肪酸を１．８質量％以上１００質量％以下含有し、
    　前記グリセリン脂肪酸エステルの総脂肪酸中、炭素数が１２である脂肪酸の含有量が、前記炭素数が１３以上１５以下である脂肪酸の含有量に対する質量比で０以上２．５以下である、可塑性油脂組成物の風味の向上方法。     A method for improving the flavor of a plastic oil-and-fat composition, comprising a step of mixing a raw material containing an oil-and-fat composition,
    The oil and fat composition contains a glycerin fatty acid ester containing a fatty acid residue having a carbon number of 13 to 15,
    The glycerin fatty acid ester contains 1.8% by mass or more and 100% by mass or less of fatty acids having 13 or more and 15 or less carbon atoms in the total fatty acids of the glycerin fatty acid ester,
    A method for improving the flavor of a plastic oil composition, wherein the content of fatty acids having 12 carbon atoms in the total fatty acids of the glycerin fatty acid ester is in a mass ratio of 0 to 2.5 relative to the content of fatty acids having 13 to 15 carbon atoms.
PCT/JP2024/010687 2023-03-30 2024-03-19 Plastic oil/fat composition production method and food production method WO2024203587A1 (en)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4832164B1 (en) * 1969-10-31 1973-10-04
JPS4928644B1 (en) * 1970-02-06 1974-07-29
US20030039737A1 (en) * 2001-07-16 2003-02-27 Cooper Garth J. S. Population of dairy cows producing milk with desirable characteristics and methods of making and using same
JP2011160745A (en) * 2010-02-12 2011-08-25 Kao Corp Butter creams

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4832164B1 (en) * 1969-10-31 1973-10-04
JPS4928644B1 (en) * 1970-02-06 1974-07-29
US20030039737A1 (en) * 2001-07-16 2003-02-27 Cooper Garth J. S. Population of dairy cows producing milk with desirable characteristics and methods of making and using same
JP2011160745A (en) * 2010-02-12 2011-08-25 Kao Corp Butter creams

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