WO2023199789A1 - Hydrogenation odor–imparting agent, fat and oil composition, production method for fat and oil composition, method for imparting hydrogenation odor to food, method for producing fried food - Google Patents

Hydrogenation odor–imparting agent, fat and oil composition, production method for fat and oil composition, method for imparting hydrogenation odor to food, method for producing fried food Download PDF

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WO2023199789A1
WO2023199789A1 PCT/JP2023/013897 JP2023013897W WO2023199789A1 WO 2023199789 A1 WO2023199789 A1 WO 2023199789A1 JP 2023013897 W JP2023013897 W JP 2023013897W WO 2023199789 A1 WO2023199789 A1 WO 2023199789A1
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Prior art keywords
oil
fat
nonenal
oxidized
less
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PCT/JP2023/013897
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French (fr)
Japanese (ja)
Inventor
恵理奈 肥山
瑞貴 山中
真祐 春口
里奈 清水
勇介 原
賀美 井上
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株式会社Ｊ－オイルミルズ
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Publication of WO2023199789A1 publication Critical patent/WO2023199789A1/en

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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
    • A23L5/10—General methods of cooking foods, e.g. by roasting or frying

Definitions

  • the present invention relates to a hydrogenated odor imparting agent, an oil and fat composition, a method for producing an oil and fat composition, a method for imparting a hydrogenated odor to foods, and a method for producing fried foods.
  • Hydrogenated oils are widely used in oil and fat foods such as margarine, shortening, and butter cream, confectionery such as donuts, cakes, and chocolate, and as frying oil for other foods.
  • Hydrogenated oils include vegetable oils and fats such as soybean oil, rapeseed oil, palm oil, coconut oil, and palm kernel oil, or animal fats and oils such as whale oil, fish oil, beef tallow, and pork fat, in a temperature range of about 160°C to about 210°C. It is produced by hydrogenation in the presence of a nickel catalyst or the like at a temperature of . Hydrogenated oils are edible processed oils and fats that are solid at room temperature, are manufactured using inexpensive oil and fat raw materials, and have stable quality, so they are used in large quantities and in a wide range of applications.
  • Hydrogenated oils include partially hydrogenated fats and oils, which are hydrogenated so that some unsaturated fatty acids remain, and highly hydrogenated oils, which are hydrogenated so that unsaturated fatty acids are completely eliminated.
  • partially hydrogenated fats and oils have an odor called "hydrogenated odor". Hydrogenated odors tend to be perceived as imparting a sticky, elegant sweetness that is created as a result of food processing such as heating being applied to foods containing hydrogenated oils. For example, when fats and oils containing hydrogenated oil are used as frying oil for donuts, the cooked donuts are given a sweet cooking taste, which motivates consumers to purchase them and gives them a sufficient sense of satisfaction when eating them. Additionally, products using hydrogenated oils such as margarine and fat spreads have a unique richness and sweetness that enhance their flavor.
  • Patent Document 1 describes a hydrogenated oil flavoring agent consisting of (E)-6-octenal.
  • Patent Document 1 only describes that a hydrogenated oil flavor can be imparted to an oil and fat product with reduced hydrogenated oil, and does not mention that a hydrogenated oil flavor can be imparted to an oil and fat product that does not contain hydrogenated oil. However, it is insufficient.
  • the problem to be solved by the present invention is to provide a hydrogenated odor imparting agent and an oil/fat composition that can impart a hydrogenated odor to foods even if they do not contain partially hydrogenated oil/fat.
  • Another problem to be solved by the present invention is a method for producing the oil and fat composition, a method for imparting a hydrogenated odor to food without adding partially hydrogenated oil and fat to food, and a method using the oil and fat composition. It is an object of the present invention to provide a method for producing a food including a step of frying fried seeds in oil.
  • the present inventors have made repeated studies in view of the above-mentioned problems, and have combined at least one selected from the group consisting of oxidized fats and oils, rice oil, linseed oil, and evening primrose oil, cis-6-nonenal, and trans-6-nonenal. It has been found that even if the agent contained as an active ingredient does not contain partially hydrogenated fats and oils, it is possible to impart a hydrogenated odor to foods. The present invention has been completed based on these findings.
  • the present invention provides a hydrogenated odor-imparting method containing as active ingredients at least one selected from the group consisting of oxidized oil, rice oil, linseed oil, and evening primrose oil, cis-6-nonenal, and trans-6-nonenal. It is a drug.
  • the content ratio of the cis-6-nonenal to the trans-6-nonenal is preferably 0.01 or more and 50 or less.
  • the hydrogenated odor imparting agent preferably contains the oxidized fat, and the peroxide value of the oxidized fat is preferably 15 or more and 350 or less.
  • the oxidized fat is preferably at least one oxidized fat selected from the group consisting of milk fat, arachidonic acid-containing fat, sunflower oil, and macadamia nut oil.
  • the present invention comprises at least one selected from the group consisting of oxidized oil, rice oil, linseed oil, and evening primrose oil, cis-6-nonenal, trans-6-nonenal, and an edible oil or fat as a base oil. It is an oil and fat composition.
  • the content of cis-6-nonenal is preferably 0.01 ppm or more and 10 ppm or less, and the content of trans-6-nonenal is preferably 0.01 ppm or more and 10 ppm or less.
  • the oil and fat composition of the present invention preferably contains the oxidized oil and fat, and the peroxide value of the oxidized oil and fat is preferably 15 or more and 350 or less.
  • the oxidized fat is preferably at least one oxidized fat selected from the group consisting of milk fat, arachidonic acid-containing fat, sunflower oil, and macadamia nut oil.
  • the content of at least one selected from the group consisting of the oxidized oil, rice oil, linseed oil, and evening primrose oil is preferably 1 ppm or more and 30,000 ppm or less.
  • the oil and fat composition of the present invention is preferably used for frying.
  • At least one selected from the group consisting of oxidized oil, rice oil, linseed oil, and evening primrose oil, cis-6-nonenal, and trans-6-nonenal are added to an edible oil or fat as a base oil.
  • This is a method for producing an oil and fat composition including the steps of:
  • the method for producing an oil and fat composition of the present invention preferably includes oxidizing the edible oil and fat, which is a raw material for the oxidized oil, by heating the edible oil and fat while supplying air so that the peroxide value becomes 15 to 300.
  • the method further includes a step of producing the oxidized fat.
  • the edible fat or oil used as a raw material for the oxidized fat is preferably at least one selected from the group consisting of milk fat, arachidonic acid-containing fat, sunflower oil, and macadamia nut oil.
  • the amount of air supplied in the oxidation treatment is preferably 0.005 L/min or more and 10 L/min or less per 1 kg of the edible fat or oil.
  • the heating temperature in the oxidation treatment is preferably 50°C or more and 220°C or less.
  • the present invention provides a food product comprising the step of adding at least one member selected from the group consisting of oxidized oil, rice oil, linseed oil, and evening primrose oil, cis-6-nonenal, and trans-6-nonenal to the food product. This is a method of imparting a hydrogenated odor to the food product.
  • the present invention provides an edible fat that is a base oil by adding at least one selected from the group consisting of oxidized fat, rice oil, linseed oil, and evening primrose oil, cis-6-nonenal, and trans-6-nonenal.
  • This is a method for producing fried foods, which includes the steps of: adding the oil and fat composition to produce an oil and fat composition; and frying fried seeds using the oil and fat composition.
  • the hydrogenated odor imparting agent and oil/fat composition of the present invention can impart a hydrogenated odor to foods even if they do not contain partially hydrogenated oil/fat.
  • the method for producing an oil or fat composition of the present invention can produce an oil or fat composition that can impart hydrogenated odor to foods even if it does not contain partially hydrogenated oil or fat.
  • the method of imparting hydrogenated odor to foods of the present invention can impart hydrogenated odor to foods without adding partially hydrogenated fats and oils to foods.
  • fried foods can be produced by frying fried seeds using an oil or fat composition that can impart a hydrogenated odor to fried foods even if the partially hydrogenated oil or fat is not included.
  • the hydrogenated odor imparting agent of the present invention contains as an active ingredient at least one selected from the group consisting of oxidized fats and oils, rice oil, linseed oil, and evening primrose oil.
  • the hydrogenated odor imparting agent of the present invention preferably contains oxidized fats and oils. Oxidized fats and oils are obtained by oxidizing raw material edible fats and oils.
  • the edible fats and oils used as raw materials for oxidation treatment are not particularly limited as long as they are edible and edible, but include rapeseed oil, soybean oil, palm oil, corn oil, olive oil, sesame oil, linseed oil, perilla oil, Vegetable oils and fats such as safflower oil, sunflower oil, cottonseed oil, rice oil, peanut oil, shea butter, monkey fat, cacao butter, palm kernel oil, coconut oil, grapeseed oil, macadamia nut oil, coconut oil, evening primrose oil; microbial fats and oils Animal fats and oils such as beef tallow, lard, milk fat, chicken oil, and fish oil; Synthetic fats and oils such as medium-chain fatty acid triglycerides; and the like.
  • the edible fats and oils used as raw materials for oxidation treatment include milk fat, arachidonic acid-containing fat, sunflower oil, macadamia nut oil, rapeseed oil, soybean oil, corn oil, grapeseed oil, lard, coconut oil, rice oil, and linseed oil.
  • the oil is at least one type of oil selected from the group consisting of milk fat, arachidonic acid-containing oil, sunflower oil, and macadamia nut oil.
  • the peroxide value of edible oils and fats generally distributed in the market is about 0 to 10, but the peroxide value is increased to about 15 to 350.
  • the range of peroxide value (hereinafter sometimes referred to as "POV") may be in the range of 20 to 300, and may be in the range of 25 to 290. , may be in the range of 40 or more and 270 or less, and may be in the range of 60 or more and 250 or less.
  • the peroxide value can be measured in accordance with "Standard Oil and Fat Analysis Test Method 2.5.2 Peroxide Value" (Japan Oil Chemists' Society).
  • the oils and fats to be subjected to oxidation treatment may be used alone or in combination of two or more types, but when two or more types are used together, the peroxide value of the entire mixed oil after oxidation treatment may be within the above range.
  • two or more types of fats and oils may be oxidized separately and then mixed, as long as the peroxide value of the entire mixed oil obtained by mixing after the oxidation treatment is within the above range.
  • the above milk fat is obtained from raw milk, cow's milk, special milk, etc. and has an oil and fat content of 95% by mass or more and 100% by mass or less.
  • Examples include anhydrous milk fat, clarified butter, and the like.
  • Anhydrous milk fat refers to milk etc. from which almost all components other than milk fat have been removed, and is sometimes expressed as AMF (Anhydrous Milk Fat, butter oil).
  • Clarified butter is butter with the fat content removed.
  • the milk fat used in the present invention is preferably anhydrous milk fat or clarified butter, more preferably anhydrous milk fat.
  • the oil content of the milk fat is preferably 98% by mass or more and 100% by mass or less, more preferably 99% by mass or more and 100% by mass or less.
  • the arachidonic acid-containing fat or oil refers to a fat or oil containing arachidonic acid.
  • arachidonic acid there is no particular restriction on the origin of arachidonic acid, and those obtained from various animals and plants, microorganisms, algae, etc. are commercially available, and those skilled in the art can use these known ones as appropriate, but it is preferably derived from microorganisms.
  • the content of arachidonic acid in the arachidonic acid-containing oil is not particularly limited, but is preferably 5% by mass or more, more preferably 8% by mass or more, and preferably 10% by mass or more. More preferred.
  • the proportion of oleic acid in the total amount of constituent fatty acids is preferably 70% by mass or more and 100% by mass or less, more preferably 75% by mass or more and 95% by mass or less.
  • the content is preferably 80% by mass or more and 90% by mass or less.
  • the content of oleic acid in the total amount of constituent fatty acids shall be measured in accordance with the method described in "Standard Oil and Fat Analysis Test Method 2.5.23-2013 Fatty Acid Composition (Capillary Gas Chromatography Method” (Japan Oil Chemists' Society)) I can do it.
  • oxidized edible oils and fats are compositions made up of an extremely large variety of chemical substances, and it is either impossible to investigate and identify each chemical substance contained, or it may be extremely excessive. This method is not practical because it requires a large amount of financial expenditure and time.
  • the rice oil may contain rice germ oil.
  • the hydrogenated odor imparting agent of the present invention contains cis-6-nonenal and trans-6-nonenal as active ingredients. These are well-known compounds, and cis-6-nonenal manufactured by Sigma Adrich and trans-6-nonenal manufactured by Sundia MediTech Company are known.
  • the hydrogenated odor-imparting agent of the present invention may optionally contain auxiliary agents that are commonly added to edible foods.
  • auxiliary agents include antioxidants, antifoaming agents, emulsifiers, perfumes, flavoring agents, pigments, physiologically active substances, and the like. Specific examples include ascorbic acid fatty acid ester, lignan, coenzyme Q, ⁇ -oryzanol, tocopherol, and silicone.
  • the hydrogenated odor imparting agent of the present invention may or may not contain partially hydrogenated fats and oils, but preferably does not contain partially hydrogenated fats and oils. This results in a composition that does not contain trans fatty acids.
  • the partially hydrogenated fat or oil in the present invention means a hydrogenated fat or oil having an iodine value of 4 or more.
  • the content ratio of cis-6-nonenal and trans-6-nonenal in the hydrogenated odorant of the present invention is preferably It is 0.01 or more and 50 or less.
  • the content is 0.02 or more and 50 or less, 0.03 or more and 50 or less, 0.04 or more and 50 or less, 0.05 or more and 50 or less, 0.06 or more and 50 or less, 0.07 or more and 50 or less, and 0.08 or more. It may be 50 or less, or 0.09 or more and 50 or less.
  • the content is more preferably 0.05 or more and 40 or less, still more preferably 0.1 or more and 30 or less, particularly preferably 0.15 or more and 25 or less, most preferably 1.0 or more and 20 or less, and most preferably 2 .0 or more and 10 or less.
  • the hydrogenated odor imparting agent of the present invention can impart hydrogenated odor to foods with higher efficiency.
  • the hydrogenated odorant of the present invention may be provided in the form of an oil or fat composition.
  • the oil and fat composition of the present invention comprises at least one selected from the group consisting of oxidized oil, rice oil, linseed oil, and evening primrose oil, cis-6-nonenal, trans-6-nonenal, and an edible base oil. Contains oils and fats.
  • the oil and fat composition of the present invention can be prepared in any form such as liquid, powder, paste, etc. by adding excipients, adjuvants, emulsifiers, pH adjusters, etc. as necessary and using known methods. It can be made into an oil and fat composition.
  • liquid oils, margarines, fat spreads, shortenings, powdered oils, etc. mainly composed of edible oils and fats may be prepared by pharmaceutical techniques commonly known to those skilled in the art, or the amount of edible oils and fats may be adjusted. It may be prepared in the form of a small solution, powder, gel, granules, etc., and any form thereof may be adopted.
  • an auxiliary agent such as corn syrup may be used, and an emulsifying raw material may be prepared by adding an emulsifier, which may then be powdered.
  • means for powdering include spray drying and freeze drying.
  • the oil and fat composition of the present invention contains an oxidized oil and fat
  • the oxidized oil and fat are as described above.
  • the content of at least one selected from the group consisting of oxidized oil, rice oil, linseed oil, and evening primrose oil contained in the oil and fat composition of the present invention is preferably 1 ppm to 30,000 ppm, more preferably 100 ppm to 25,000 ppm.
  • the content is more preferably 250 ppm or more and 23,000 ppm or less, particularly preferably 500 ppm or more and 21,000 ppm or less.
  • the oil and fat composition of the present invention can impart a hydrogenated odor to foods with higher efficiency.
  • the cis-6-nonenal and trans-6-nonenal contained in the oil and fat composition of the present invention are also as described above.
  • the content of cis-6-nonenal and the content of trans-6-nonenal contained in the oil and fat composition of the present invention are preferably 0.01 ppm or more and 10 ppm or less, more preferably 0.02 ppm or more and 8 ppm or less, and Preferably it is 0.03 ppm or more and 5 ppm or less, particularly preferably 0.05 ppm or more and 3 ppm or less.
  • the oil and fat composition of the present invention can impart a hydrogenated odor to foods with higher efficiency.
  • the total content of cis-6-nonenal and trans-6-nonenal contained in the oil and fat composition of the present invention is preferably 0.1 ppm or more and 20 ppm or less, more preferably 0.15 ppm or more and 10 ppm or less, and even more preferably 0. It is 2 ppm or more and 5 ppm or less, particularly preferably 0.25 ppm or more and 2 ppm or less, and most preferably 0.3 ppm or more and 1.5 ppm or less.
  • the oil and fat composition of the present invention can impart hydrogenated odor to foods with higher efficiency.
  • the edible oils and fats that are the base oils contained in the oil and fat compositions of the present invention include, for example, rapeseed oil (including high oleic acid types), soybean oil, palm oil, palm kernel oil, corn oil, olive oil, sesame oil, linseed oil, Vegetable oils and fats such as perilla oil, safflower oil, sunflower oil, cottonseed oil, rice oil, peanut oil, coconut oil, shea butter, monkey fat, cacao butter, grapeseed oil, macadamia nut oil, coconut oil, evening primrose oil, beef tallow, pork Examples include animal fats and oils such as fat, chicken fat, and milk fat, medium-chain fatty acid triglycerides, and the like.
  • processed oils and fats such as these fractionated oils (medium melting point part of palm oil, soft fractionated palm oil, hard fractionated palm oil, etc.), transesterified oil, and the like can be mentioned.
  • Edible fats and oils may be used alone or in combination of two or more.
  • the fat and oil composition of the present invention may optionally contain auxiliary agents that are commonly added to edible foods.
  • auxiliary agents include antioxidants, antifoaming agents, emulsifiers, fragrances, flavoring agents, pigments, and physiologically active substances. Specific examples include ascorbic acid fatty acid ester, lignan, coenzyme Q, ⁇ -oryzanol, tocopherol, and silicone.
  • the oil and fat composition of the present invention may or may not contain partially hydrogenated fats and oils, but preferably does not contain hydrogenated oils, particularly partially hydrogenated fats and oils. This results in a composition that does not contain trans fatty acids.
  • the use of the oil and fat composition of the present invention is not limited to specific uses.
  • the oil and fat composition of the present invention is preferably used as an oil and fat composition for frying.
  • the method for producing an oil and fat composition of the present invention includes at least one selected from the group consisting of oxidized oil, rice oil, linseed oil, and evening primrose oil, cis-6-nonenal, and trans-6-nonenal as a base. It includes the process of adding to edible fats and oils.
  • the oxidized oil or fat is obtained by oxidizing the edible oil or fat used as the raw material, as described above.
  • the method for producing an oil or fat composition of the present invention preferably includes oxidizing the edible oil or fat, which is a raw material for the oxidized oil, by heat-treating the edible oil or fat while supplying air so that the peroxide value becomes 15 or more and 350 or less.
  • the method further includes a step of producing the oxidized fat.
  • the method of oxidizing the edible oil or fat used as the raw material may be any method as long as it can be oxidized to a peroxide value within the above-mentioned predetermined range, and is not particularly limited, but preferably includes a method of heat treatment.
  • a suitable container such as a tank
  • the container is equipped with a heating method such as an electric heating type, a direct flame burner type, a microwave type, a steam type, or a hot air type. It is preferable to do so.
  • the heating temperature is 50°C or more and 220°C or less, and the heating time is 0.1 hour or more and 240 hours or less, and the heating temperature is 60°C or more and 160°C or less, More preferably, the heating time is 1 hour or more and 100 hours or less.
  • the cumulative amount of heating temperature (°C) x heating time (hours) is preferably 200 or more and 20,000 or less, more preferably 220 or more and 18,000 or less, and even more preferably 240 or more and 15,000 or less.
  • the cumulative amount of heating temperature (°C) x heating time (hours) is: heating temperature (°C) before changing the temperature x heating time (hours) before changing the temperature + It can be calculated as the heating temperature (°C) after changing the temperature x the heating time (hours) after changing the temperature, or the integral value of the heating temperature (°C) over the heating time (hours).
  • oxygen may be supplied by taking in oxygen from the open space of the container by stirring or by blowing oxygen into the container.
  • Air or the like may be used as the oxygen source. This promotes the oxidation of the edible oil and fat used as the raw material.
  • the amount of oxygen supplied is preferably in a range of 0.001 L/min or more and 2 L/min or less per 1 kg of the edible fat or oil.
  • the flow rate is preferably in the range of 0.005 L/min or more and 10 L/min or less, and more preferably 0.01 L/min or more and 5 L/min or less per 1 kg of the fat or oil.
  • the method of imparting a hydrogenated odor to foods of the present invention includes at least one selected from the group consisting of oxidized fats and oils, rice oil, linseed oil, and evening primrose oil, cis-6-nonenal, and trans-6-nonenal. It includes the process of adding to food.
  • the hydrogenated odor imparting agent of the present invention or the fat composition of the present invention is added to foods.
  • the method of addition is not particularly limited; for example, the hydrogenated odor imparting agent of the present invention or the oil/fat composition of the present invention may be added to foods as is, or the oil/fat composition of the present invention may be made into a flavored oil and then added to foods. may be added to.
  • fried seeds may be fried using the edible oil or fat to which the hydrogenated odor-imparting agent of the present invention has been added or the oil and fat composition of the present invention, giving the fried food (fried food) a unique sweet aroma. It can give a pleasant flavor.
  • Foods to which the hydrogenated odorant or fat composition of the present invention is added are not particularly limited, but include, for example: Edible fats and oils; Processed oil and fat foods such as margarine, spreads, butter, mayonnaise, dressings, and creams (referring to foods that contain edible oils and fats as raw materials); Beverages such as milk, soy milk, milk drinks, lactic acid drinks, sports drinks; Confectionery such as donuts, cookies, pies, cakes, madeleines, jellies, puddings, mousses, chocolates, and gummies; Bread such as sweet bread; Noodles such as soba, udon, ramen, and pasta; Rice such as fried rice; Dairy products such as cheese, butter, and yogurt; Processed meat foods such as hamburgers, hams, and sausages; Processed seafood foods such as chikuwa and kamaboko; Soups such as corn soup, consommé soup, and potage; Seasonings and sauces such as Chinese ingredients and grilled meat sauce;
  • the method for producing fried foods of the present invention includes adding at least one selected from the group consisting of oxidized oil, rice oil, linseed oil, and evening primrose oil, cis-6-nonenal, and trans-6-nonenal to a base oil.
  • the method includes a step of adding to an edible fat and oil to produce an oil and fat composition, and a step of frying fried seeds using the oil and fat composition.
  • Examples of the fried foods include, but are not limited to, donuts, fried bread, curry bread, piroshki, corn dogs, croutons, karinto, fried rice crackers, snacks, fritters, pork cutlets, chicken cutlets, fried chicken, fried chicken, and fried fish. , tempura, croquettes, minced meat cutlets, fries, chicken nuggets, hash browns, fried tofu, instant ramen, etc.
  • Examples 1 to 25 and Comparative Examples 1 to 4 Refined palm oil (manufactured by J-Oil Mills Co., Ltd.) 60% by mass and transesterified oil (the transesterified oil is transesterified fat 1 prepared in [Example] described in International Publication No. 2020/004058) Specifically, after mixing 75% by mass of palm stearin (iodine value 35), 10% by mass of palm oil, and 15% by mass of soybean oil, the mixture was prepared using sodium methoxide as a catalyst. A mixed oil consisting of 40% by mass (prepared by transesterification and further refinement) was used as the base oil, and each component was added to the base oil to the concentration shown in Tables 1 to 6. Each oil and fat composition was prepared.
  • Comparative example 5 The donut dough was fried in the same manner as the donut dough using the oil and fat composition consisting only of the base oil. The results are shown in Table 6.
  • Control example 1 The donut dough was fried in the same manner as the donut dough using an oil and fat composition consisting of 60% by mass of the refined palm oil and 40% by mass of hydrogenated rapeseed fat (manufactured by J-Oil Mills Co., Ltd.). The results are shown in Table 6.
  • the donuts fried with oil and fat compositions of Comparative Examples 1 to 4 that did not contain cis-6-nonenal had a flavor somewhat similar to the control donuts that were fried with the oil and fat composition of Comparative Example 1. , or the flavor was not close to that of the control donut.
  • the donuts fried with the oil and fat composition of Comparative Example 5 that did not contain cis-6-nonenal and trans-6-nonenal did not have a flavor similar to the control donut.
  • the donuts fried using the oil and fat compositions of Examples 1 to 25 had a flavor very similar to or similar to the control donut.
  • each oil and fat composition was prepared by adding each component to the base oil so as to have the concentrations shown in Tables 7 and 8.
  • commercially available fried chicken (boneless fried chicken manufactured by Ajinomoto Frozen Foods Co., Ltd.) was fried at 180° C. for 5 minutes and 30 seconds. The results are shown in Tables 7 and 8.
  • Comparative example 7 The commercially available fried chicken was fried in the same manner as the fried chicken using the oil and fat composition consisting only of the base oil. The results are shown in Table 8.
  • Control example 2 The commercially available fried chicken was fried in the same manner as the fried chicken using an oil and fat composition consisting of 60% by mass of the purified palm oil and 40% by mass of hydrogenated rapeseed fat (manufactured by J-Oil Mills Co., Ltd.). The results are shown in Table 8.

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  • Engineering & Computer Science (AREA)
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Abstract

Provided is a hydrogenation odor–imparting agent that can impart a hydrogenation odor to food even when a partially hydrogenated oil is not included.　The hydrogenation odor–imparting agent contains, as active ingredients, cis-6-Nonenal, trans-6-Nonenal, and at least one selected from the group consisting of oxidized fats and oils, rice oil, linseed oil, and evening primrose oil. Also provided is a fat and oil composition containing cis-6-Nonenal, trans-6-Nonenal, an edible fat and oil serving as a base oil, and at least one selected from the group consisting of oxidized fats and oils, rice oil, linseed oil, and evening primrose oil.

Description

水添臭付与剤、油脂組成物、油脂組成物の製造方法、食品に水添臭を付与する方法、及びフライ食品の製造方法Hydrogenated odor imparting agent, oil and fat composition, method for producing oil and fat composition, method for imparting hydrogenated odor to food, and method for producing fried food
　本発明は、水添臭付与剤、油脂組成物、油脂組成物の製造方法、食品に水添臭を付与する方法、及びフライ食品の製造方法に関する。 The present invention relates to a hydrogenated odor imparting agent, an oil and fat composition, a method for producing an oil and fat composition, a method for imparting a hydrogenated odor to foods, and a method for producing fried foods.
　硬化油は、マーガリン、ショートニング、バタークリーム等の油脂食品、ドーナッツ、ケーキ、チョコレート等の菓子類、その他の食品の揚げ油などに幅広く利用されている。 Hydrogenated oils are widely used in oil and fat foods such as margarine, shortening, and butter cream, confectionery such as donuts, cakes, and chocolate, and as frying oil for other foods.
　硬化油は、大豆油、菜種油、パーム油、ヤシ油、パーム核油等の植物性油脂、あるいは鯨油、魚油、牛脂、豚脂等の動物性油脂に、約１６０℃以上約２１０℃以下の範囲の温度で、ニッケル触媒等の存在下に水素添加する方法等により製造されている。硬化油は、常温で固形の食用加工油脂であり、安価な油脂原料を用いて製造され、かつ品質が安定しているから、大量かつ広い応用範囲で使用されている。 Hydrogenated oils include vegetable oils and fats such as soybean oil, rapeseed oil, palm oil, coconut oil, and palm kernel oil, or animal fats and oils such as whale oil, fish oil, beef tallow, and pork fat, in a temperature range of about 160°C to about 210°C. It is produced by hydrogenation in the presence of a nickel catalyst or the like at a temperature of . Hydrogenated oils are edible processed oils and fats that are solid at room temperature, are manufactured using inexpensive oil and fat raw materials, and have stable quality, so they are used in large quantities and in a wide range of applications.
　硬化油には、不飽和脂肪酸の一部が残るように水素添加した部分水素添加油脂と、不飽和脂肪酸が完全になくなるように水素添加した極度硬化油とがある。このうち、特に部分水素添加油脂は、「水添臭」と呼ばれる臭気を有する。水添臭は、硬化油を含む食品に加熱等の食品加工が加えられる結果、醸成されるねっとりとした上品な甘さを付与すると認識される傾向がある。例えば、ドーナッツの揚げ油として硬化油を含む油脂を使用した場合、調理されたドーナッツに甘い調理感が付与され、消費者の購買意欲を惹起し、喫食時に十分な満足感を与える。また、マーガリン、ファットスプレッド等の硬化油を使用した製品は、独特のコクと甘さがこれらの風味を増加させる。 Hydrogenated oils include partially hydrogenated fats and oils, which are hydrogenated so that some unsaturated fatty acids remain, and highly hydrogenated oils, which are hydrogenated so that unsaturated fatty acids are completely eliminated. Among these, partially hydrogenated fats and oils have an odor called "hydrogenated odor". Hydrogenated odors tend to be perceived as imparting a sticky, elegant sweetness that is created as a result of food processing such as heating being applied to foods containing hydrogenated oils. For example, when fats and oils containing hydrogenated oil are used as frying oil for donuts, the cooked donuts are given a sweet cooking taste, which motivates consumers to purchase them and gives them a sufficient sense of satisfaction when eating them. Additionally, products using hydrogenated oils such as margarine and fat spreads have a unique richness and sweetness that enhance their flavor.
　一方、部分水素添加油脂においては、水素添加処理により油脂中のトランス脂肪酸含有量が増加することが知られている。最近、トランス脂肪酸が動脈硬化等の原因となる可能性があるとして、その表示指針が米国連邦政府より発表された結果、トランス脂肪酸を多く含む硬化油の使用が嫌われるケースも増えており、代替油脂の開発等の有効な解決法の出現が強く望まれている。 On the other hand, in partially hydrogenated fats and oils, it is known that hydrogenation treatment increases the trans fatty acid content in the fats and oils. Recently, the U.S. federal government has announced labeling guidelines for trans fatty acids, which may cause arteriosclerosis, etc. As a result, there are an increasing number of cases in which the use of hydrogenated oils containing a large amount of trans fatty acids is discouraged, and alternatives are being sought. The emergence of effective solutions such as the development of oils and fats is strongly desired.
　特許文献１には、（Ｅ）－６－オクテナールからなる硬化油風味付与剤が記載されている。 Patent Document 1 describes a hydrogenated oil flavoring agent consisting of (E)-6-octenal.
特開２０１４－２００２３６号公報Japanese Patent Application Publication No. 2014-200236
　しかしながら、特許文献１では、硬化油を低減した油脂製品に対して硬化油風味を付与できる点が記載されているのみであり、硬化油を含まない油脂製品に対して硬化油風味を付与する点においては、不十分である。 However, Patent Document 1 only describes that a hydrogenated oil flavor can be imparted to an oil and fat product with reduced hydrogenated oil, and does not mention that a hydrogenated oil flavor can be imparted to an oil and fat product that does not contain hydrogenated oil. However, it is insufficient.
　近年、硬化油、なかでも部分水素添加油脂を含んでいなくても、水添臭を食品に付与できる化合物を有効成分とする水添臭付与剤、及び部分水素添加油脂を含んでいなくても当該化合物を含む油脂組成物が希求されていたが、そのような水添臭付与剤及び油脂組成物は提供されていなかった。本発明が解決しようとする課題は、部分水素添加油脂を含んでいなくても、水添臭を食品に付与できる水添臭付与剤及び油脂組成物を提供することである。さらに本発明が解決しようとする別の課題は、前記油脂組成物の製造方法、部分水素添加油脂を食品に添加しなくても食品に水添臭を付与する方法、及び前記油脂組成物を用いて揚げ種を油ちょうする工程を含む食品の製造方法を提供することである。 In recent years, hydrogenated oils, especially hydrogenated odor-imparting agents whose active ingredients are compounds that can impart a hydrogenated odor to foods even if they do not contain partially hydrogenated fats and oils, and hydrogenated odor-imparting agents that do not contain partially hydrogenated fats and oils, However, such hydrogenated odor-imparting agents and fat compositions have not been provided. The problem to be solved by the present invention is to provide a hydrogenated odor imparting agent and an oil/fat composition that can impart a hydrogenated odor to foods even if they do not contain partially hydrogenated oil/fat. Furthermore, another problem to be solved by the present invention is a method for producing the oil and fat composition, a method for imparting a hydrogenated odor to food without adding partially hydrogenated oil and fat to food, and a method using the oil and fat composition. It is an object of the present invention to provide a method for producing a food including a step of frying fried seeds in oil.
　本発明者らは上記課題に鑑み検討を重ね、酸化油脂、米油、アマニ油、及び月見草油からなる群から選ばれる少なくとも１種と、シス－６－ノネナールと、トランス－６－ノネナールとを有効成分として含む剤が、部分水素添加油脂を含んでいなくても食品に水添臭を付与できることを見出した。本発明はこれらの知見に基づき完成されるに至ったものである。 The present inventors have made repeated studies in view of the above-mentioned problems, and have combined at least one selected from the group consisting of oxidized fats and oils, rice oil, linseed oil, and evening primrose oil, cis-6-nonenal, and trans-6-nonenal. It has been found that even if the agent contained as an active ingredient does not contain partially hydrogenated fats and oils, it is possible to impart a hydrogenated odor to foods. The present invention has been completed based on these findings.
　本発明は、酸化油脂、米油、アマニ油、及び月見草油からなる群から選ばれる少なくとも１種と、シス－６－ノネナールと、トランス－６－ノネナールとを有効成分として含む、水添臭付与剤である。
　前記シス－６－ノネナールと前記トランス－６－ノネナールとの含有量の比は、好ましくは０．０１以上５０以下である。
　前記水添臭付与剤は、好ましくは前記酸化油脂を含み、前記酸化油脂の過酸化物価は、好ましくは１５以上３５０以下である。また、前記酸化油脂は、好ましくは乳脂、アラキドン酸含有油脂、ヒマワリ油、及びマカダミアナッツオイルからなる群から選ばれる少なくとも１種の酸化油脂である。 The present invention provides a hydrogenated odor-imparting method containing as active ingredients at least one selected from the group consisting of oxidized oil, rice oil, linseed oil, and evening primrose oil, cis-6-nonenal, and trans-6-nonenal. It is a drug.
The content ratio of the cis-6-nonenal to the trans-6-nonenal is preferably 0.01 or more and 50 or less.
The hydrogenated odor imparting agent preferably contains the oxidized fat, and the peroxide value of the oxidized fat is preferably 15 or more and 350 or less. The oxidized fat is preferably at least one oxidized fat selected from the group consisting of milk fat, arachidonic acid-containing fat, sunflower oil, and macadamia nut oil.
　本発明は、酸化油脂、米油、アマニ油、及び月見草油からなる群から選ばれる少なくとも１種と、シス－６－ノネナールと、トランス－６－ノネナールと、ベース油である食用油脂とを含む油脂組成物である。
　前記シス－６－ノネナールの含有量は、好ましくは０．０１ｐｐｍ以上１０ｐｐｍ以下であり、前記トランス－６－ノネナールの含有量は、好ましくは０．０１ｐｐｍ以上１０ｐｐｍ以下である。
　本発明の油脂組成物は、好ましくは前記酸化油脂を含み、前記酸化油脂の過酸化物価は、好ましくは１５以上３５０以下である。また、前記酸化油脂は、好ましくは乳脂、アラキドン酸含有油脂、ヒマワリ油、及びマカダミアナッツオイルからなる群から選ばれる少なくとも１種の酸化油脂である。
　前記酸化油脂、米油、アマニ油、及び月見草油からなる群から選ばれる少なくとも１種の含有量は、好ましくは１ｐｐｍ以上３００００ｐｐｍ以下である。
　本発明の油脂組成物は、好ましくはフライ用である。 The present invention comprises at least one selected from the group consisting of oxidized oil, rice oil, linseed oil, and evening primrose oil, cis-6-nonenal, trans-6-nonenal, and an edible oil or fat as a base oil. It is an oil and fat composition.
The content of cis-6-nonenal is preferably 0.01 ppm or more and 10 ppm or less, and the content of trans-6-nonenal is preferably 0.01 ppm or more and 10 ppm or less.
The oil and fat composition of the present invention preferably contains the oxidized oil and fat, and the peroxide value of the oxidized oil and fat is preferably 15 or more and 350 or less. The oxidized fat is preferably at least one oxidized fat selected from the group consisting of milk fat, arachidonic acid-containing fat, sunflower oil, and macadamia nut oil.
The content of at least one selected from the group consisting of the oxidized oil, rice oil, linseed oil, and evening primrose oil is preferably 1 ppm or more and 30,000 ppm or less.
The oil and fat composition of the present invention is preferably used for frying.
　本発明は、酸化油脂、米油、アマニ油、及び月見草油からなる群から選ばれる少なくとも１種と、シス－６－ノネナールと、トランス－６－ノネナールとを、ベース油である食用油脂に添加する工程を含む油脂組成物の製造方法である。
　本発明の油脂組成物の製造方法は、好ましくは前記酸化油脂の原料となる食用油脂に空気を供給しつつ加熱処理することにより、過酸化物価が１５以上３００以下となるように酸化処理して前記酸化油脂を製造する工程を更に含む。
　前記酸化油脂の原料となる食用油脂は、好ましくは乳脂、アラキドン酸含有油脂、ヒマワリ油、及びマカダミアナッツオイルからなる群から選ばれる少なくとも１種である。
　前記酸化処理における空気の供給量は、好ましくは前記食用油脂１ｋｇあたり０．００５Ｌ／分以上１０Ｌ／分以下である。
　前記酸化処理における加熱温度は、好ましくは５０℃以上２２０℃以下である。 In the present invention, at least one selected from the group consisting of oxidized oil, rice oil, linseed oil, and evening primrose oil, cis-6-nonenal, and trans-6-nonenal are added to an edible oil or fat as a base oil. This is a method for producing an oil and fat composition, including the steps of:
The method for producing an oil and fat composition of the present invention preferably includes oxidizing the edible oil and fat, which is a raw material for the oxidized oil, by heating the edible oil and fat while supplying air so that the peroxide value becomes 15 to 300. The method further includes a step of producing the oxidized fat.
The edible fat or oil used as a raw material for the oxidized fat is preferably at least one selected from the group consisting of milk fat, arachidonic acid-containing fat, sunflower oil, and macadamia nut oil.
The amount of air supplied in the oxidation treatment is preferably 0.005 L/min or more and 10 L/min or less per 1 kg of the edible fat or oil.
The heating temperature in the oxidation treatment is preferably 50°C or more and 220°C or less.
　本発明は、酸化油脂、米油、アマニ油、及び月見草油からなる群から選ばれる少なくとも１種と、シス－６－ノネナールと、トランス－６－ノネナールとを食品に添加する工程を含む、食品に水添臭を付与する方法である。 The present invention provides a food product comprising the step of adding at least one member selected from the group consisting of oxidized oil, rice oil, linseed oil, and evening primrose oil, cis-6-nonenal, and trans-6-nonenal to the food product. This is a method of imparting a hydrogenated odor to
　さらに本発明は、酸化油脂、米油、アマニ油、及び月見草油からなる群から選ばれる少なくとも１種と、シス－６－ノネナールと、トランス－６－ノネナールとを、ベース油である食用油脂に添加し、油脂組成物を製造する工程と、当該油脂組成物を用いて揚げ種を油ちょうする工程を含む、フライ食品の製造方法である。 Furthermore, the present invention provides an edible fat that is a base oil by adding at least one selected from the group consisting of oxidized fat, rice oil, linseed oil, and evening primrose oil, cis-6-nonenal, and trans-6-nonenal. This is a method for producing fried foods, which includes the steps of: adding the oil and fat composition to produce an oil and fat composition; and frying fried seeds using the oil and fat composition.
　本発明の水添臭付与剤及び油脂組成物は、部分水素添加油脂を含んでいなくても、水添臭を食品に付与できるものである。本発明の油脂組成物の製造方法は、部分水素添加油脂を含んでいなくても、水添臭を食品に付与できる油脂組成物を製造できる。本発明の食品に水添臭を付与する方法は、部分水素添加油脂を食品に添加しなくても食品に水添臭を付与できる。本発明のフライ食品の製造方法は、部分水素添加油脂を含んでいなくても、水添臭をフライ食品に付与できる油脂組成物を用いて揚げ種を油ちょうしてフライ食品を製造できる。 The hydrogenated odor imparting agent and oil/fat composition of the present invention can impart a hydrogenated odor to foods even if they do not contain partially hydrogenated oil/fat. The method for producing an oil or fat composition of the present invention can produce an oil or fat composition that can impart hydrogenated odor to foods even if it does not contain partially hydrogenated oil or fat. The method of imparting hydrogenated odor to foods of the present invention can impart hydrogenated odor to foods without adding partially hydrogenated fats and oils to foods. In the method for producing fried foods of the present invention, fried foods can be produced by frying fried seeds using an oil or fat composition that can impart a hydrogenated odor to fried foods even if the partially hydrogenated oil or fat is not included.
　本発明について更に詳細に説明する。なお、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。
＜水添臭付与剤＞
　本発明の水添臭付与剤は、酸化油脂、米油、アマニ油、及び月見草油からなる群から選ばれる少なくとも１種を有効成分として含む。本発明の水添臭付与剤は、好ましくは酸化油脂を含む。酸化油脂は原料となる食用油脂を酸化処理して得られる。 The present invention will be explained in more detail. Note that when an upper limit value and a lower limit value of a numerical range are indicated, the upper limit value and the lower limit value can be combined as appropriate, and the resulting numerical range is also disclosed.
<Hydrogenated odor imparting agent>
The hydrogenated odor imparting agent of the present invention contains as an active ingredient at least one selected from the group consisting of oxidized fats and oils, rice oil, linseed oil, and evening primrose oil. The hydrogenated odor imparting agent of the present invention preferably contains oxidized fats and oils. Oxidized fats and oils are obtained by oxidizing raw material edible fats and oils.
　酸化処理の原料となる前記食用油脂としては、飲食可能とされた油脂であればよく、特に制限はないが、菜種油、大豆油、パーム油、コーン油、オリーブ油、ゴマ油、アマニ油、えごま油、紅花油、ヒマワリ油、綿実油、米油、落花生油、シア脂、サル脂、カカオ脂、パーム核油、ヤシ油、グレープシード油、マカダミアナッツオイル、ココナッツオイル、月見草油などの植物油脂；微生物油脂；牛脂、豚脂、乳脂、鶏油、魚油等の動物油脂；中鎖脂肪酸トリグリセリドなどの合成油脂などが挙げられる。また、アラキドン酸等の特定の脂肪酸を多く含有した油脂であってもよい。酸化処理の原料となる前記食用油脂として、乳脂、アラキドン酸含有油脂、ヒマワリ油、マカダミアナッツオイル、菜種油、大豆油、コーン油、グレープシード油、豚脂、ココナッツオイル、米油、及びアマニ油からなる群から選ばれた少なくとも１種の油脂であることが好ましく、乳脂、アラキドン酸含有油脂、ヒマワリ油、及びマカダミアナッツオイルからなる群から選ばれた少なくとも１種の油脂であることがより好ましい。酸化の程度としては、過酸化物価を指標にするとき、一般に市場に流通している食用油脂の過酸化物価が０～１０程度であるところ、その過酸化物価が１５以上３５０以下程度に高められていることが好ましい。過酸化物価（Peroxide value；以下「ＰＯＶ」という場合がある。）の範囲は、別の態様にあっては、２０以上３００以下の範囲であってよく、２５以上２９０以下の範囲であってよく、４０以上２７０以下の範囲であってよく、６０以上２５０以下の範囲であってよい。過酸化物価が上記範囲内であると水添臭付与効果が高く、食品の風味も良くなる。過酸化物価（ＰＯＶ）は、「基準油脂分析試験法　２．５．２　過酸化物価」（日本油化学会）に則って測定できる。なお、酸化処理に供する油脂は、一種類を単独で使用してもよく、二種類以上を併用してもよいが、二種類以上を併用した場合、酸化処理後の混合油全体における過酸化物価が上記範囲内であればよい。また、二種類以上の油脂を別々に酸化処理して混合してもよく、酸化処理後に混合してなる混合油全体における過酸化物価が上記範囲内であればよい。 The edible fats and oils used as raw materials for oxidation treatment are not particularly limited as long as they are edible and edible, but include rapeseed oil, soybean oil, palm oil, corn oil, olive oil, sesame oil, linseed oil, perilla oil, Vegetable oils and fats such as safflower oil, sunflower oil, cottonseed oil, rice oil, peanut oil, shea butter, monkey fat, cacao butter, palm kernel oil, coconut oil, grapeseed oil, macadamia nut oil, coconut oil, evening primrose oil; microbial fats and oils Animal fats and oils such as beef tallow, lard, milk fat, chicken oil, and fish oil; Synthetic fats and oils such as medium-chain fatty acid triglycerides; and the like. Alternatively, it may be an oil or fat containing a large amount of specific fatty acids such as arachidonic acid. The edible fats and oils used as raw materials for oxidation treatment include milk fat, arachidonic acid-containing fat, sunflower oil, macadamia nut oil, rapeseed oil, soybean oil, corn oil, grapeseed oil, lard, coconut oil, rice oil, and linseed oil. Preferably, the oil is at least one type of oil selected from the group consisting of milk fat, arachidonic acid-containing oil, sunflower oil, and macadamia nut oil. As for the degree of oxidation, when the peroxide value is used as an indicator, the peroxide value of edible oils and fats generally distributed in the market is about 0 to 10, but the peroxide value is increased to about 15 to 350. It is preferable that In another embodiment, the range of peroxide value (hereinafter sometimes referred to as "POV") may be in the range of 20 to 300, and may be in the range of 25 to 290. , may be in the range of 40 or more and 270 or less, and may be in the range of 60 or more and 250 or less. When the peroxide value is within the above range, the hydrogenation odor imparting effect is high and the flavor of the food is also good. The peroxide value (POV) can be measured in accordance with "Standard Oil and Fat Analysis Test Method 2.5.2 Peroxide Value" (Japan Oil Chemists' Society). In addition, the oils and fats to be subjected to oxidation treatment may be used alone or in combination of two or more types, but when two or more types are used together, the peroxide value of the entire mixed oil after oxidation treatment may be within the above range. Furthermore, two or more types of fats and oils may be oxidized separately and then mixed, as long as the peroxide value of the entire mixed oil obtained by mixing after the oxidation treatment is within the above range.
　前記乳脂は、生乳、牛乳、特別牛乳等から得られる油脂含量が９５質量％以上１００質量％以下のものをいう。例えば、無水乳脂、澄ましバター等が挙げられる。無水乳脂は、牛乳等から乳脂肪以外のほとんどすべての成分を除去したものをいい、ＡＭＦ（Anhydrous Milk Fat、バターオイル）等と表記される場合もある。澄ましバターはバターの脂肪分を分取したものである。本発明で使用する乳脂は、好ましくは無水乳脂または澄ましバターであり、より好ましくは無水乳脂である。また、乳脂の油脂含量は、好ましくは９８質量％以上１００質量％以下であり、より好ましくは９９質量％以上１００質量％以下である。 The above milk fat is obtained from raw milk, cow's milk, special milk, etc. and has an oil and fat content of 95% by mass or more and 100% by mass or less. Examples include anhydrous milk fat, clarified butter, and the like. Anhydrous milk fat refers to milk etc. from which almost all components other than milk fat have been removed, and is sometimes expressed as AMF (Anhydrous Milk Fat, butter oil). Clarified butter is butter with the fat content removed. The milk fat used in the present invention is preferably anhydrous milk fat or clarified butter, more preferably anhydrous milk fat. Further, the oil content of the milk fat is preferably 98% by mass or more and 100% by mass or less, more preferably 99% by mass or more and 100% by mass or less.
　前記アラキドン酸含有油脂は、アラキドン酸を含む油脂をいう。アラキドン酸の由来に特に制限はなく、各種動植物、微生物、藻類等から得られたものが市販されており、当業者はこれら公知のものを適宜使用することが出来るが、好ましくは微生物由来である。アラキドン酸含有油脂中のアラキドン酸の含有量は、特に限定するものではないが、５質量％以上であることが好ましく、８質量％以上であることがより好ましく、１０質量％以上であることが更に好ましい。 The arachidonic acid-containing fat or oil refers to a fat or oil containing arachidonic acid. There is no particular restriction on the origin of arachidonic acid, and those obtained from various animals and plants, microorganisms, algae, etc. are commercially available, and those skilled in the art can use these known ones as appropriate, but it is preferably derived from microorganisms. . The content of arachidonic acid in the arachidonic acid-containing oil is not particularly limited, but is preferably 5% by mass or more, more preferably 8% by mass or more, and preferably 10% by mass or more. More preferred.
　前記ヒマワリ油は、特に限定するものではないが、構成脂肪酸総量に占めるオレイン酸の割合が７０質量％以上１００質量％以下であることが好ましく、７５質量％以上９５質量％以下であることがより好ましく、８０質量％以上９０質量％以下であることが更に好ましい。構成脂肪酸総量に占めるオレイン酸の含有量は、「基準油脂分析試験法２．５．２３－２０１３脂肪酸組成（キャピラリーガスクロマトグラフ法」（日本油化学会）に記載の方法に準拠して測定することができる。 Although the sunflower oil is not particularly limited, the proportion of oleic acid in the total amount of constituent fatty acids is preferably 70% by mass or more and 100% by mass or less, more preferably 75% by mass or more and 95% by mass or less. The content is preferably 80% by mass or more and 90% by mass or less. The content of oleic acid in the total amount of constituent fatty acids shall be measured in accordance with the method described in "Standard Oil and Fat Analysis Test Method 2.5.23-2013 Fatty Acid Composition (Capillary Gas Chromatography Method" (Japan Oil Chemists' Society)) I can do it.
　なお、一般に、食用油脂の酸化処理物は極めて多種類の化学物質で構成される組成物となっており、含まれる化学物質を調べ、逐一特定することは、不可能であるか、又は著しく過大な経済的支出や時間を要するためおよそ実際的ではない。 In general, oxidized edible oils and fats are compositions made up of an extremely large variety of chemical substances, and it is either impossible to investigate and identify each chemical substance contained, or it may be extremely excessive. This method is not practical because it requires a large amount of financial expenditure and time.
　本発明の水添臭付与剤が有効成分として米油を含む場合、当該米油は米胚芽油を含んでいてよい。 When the hydrogenated odor-imparting agent of the present invention contains rice oil as an active ingredient, the rice oil may contain rice germ oil.
　本発明の水添臭付与剤は、シス－６－ノネナールとトランス－６－ノネナールを有効成分として含む。これらは周知の化合物であり、シス－６－ノネナールとしてシグマアドリッチ社製のもの、トランス－６－ノネナールとしてSundia MediTech Company製のもの等が知られている。 The hydrogenated odor imparting agent of the present invention contains cis-6-nonenal and trans-6-nonenal as active ingredients. These are well-known compounds, and cis-6-nonenal manufactured by Sigma Adrich and trans-6-nonenal manufactured by Sundia MediTech Company are known.
　本発明の水添臭付与剤には、食用に通常添加される助剤が適宜配合されていてもよい。当該助剤としては、酸化防止剤、消泡剤、乳化剤、香料、風味付与剤、色素、生理活性物質等が挙げられる。具体的には、例えば、アスコルビン酸脂肪酸エステル、リグナン、コエンザイムＱ、γ－オリザノール、トコフェロール、シリコーン等が挙げられる。 The hydrogenated odor-imparting agent of the present invention may optionally contain auxiliary agents that are commonly added to edible foods. Examples of the auxiliary agents include antioxidants, antifoaming agents, emulsifiers, perfumes, flavoring agents, pigments, physiologically active substances, and the like. Specific examples include ascorbic acid fatty acid ester, lignan, coenzyme Q, γ-oryzanol, tocopherol, and silicone.
　本発明の水添臭付与剤は、部分水素添加油脂を含んでいても、含んでいなくてもよいが、好ましくは部分水素添加油脂を含まない。それによって、トランス脂肪酸を含まない組成となる。本発明における部分水素添加油脂は、ヨウ素価が４以上の水素添加油脂を意味する。 The hydrogenated odor imparting agent of the present invention may or may not contain partially hydrogenated fats and oils, but preferably does not contain partially hydrogenated fats and oils. This results in a composition that does not contain trans fatty acids. The partially hydrogenated fat or oil in the present invention means a hydrogenated fat or oil having an iodine value of 4 or more.
　本発明の水添臭付与剤中のシス－６－ノネナールとトランス－６－ノネナールとの含有量の比（シス－６－ノネナールの含有量／トランス－６－ノネナールの含有量）は、好ましくは０．０１以上５０以下である。前記含有量は０．０２以上５０以下、０．０３以上５０以下、０．０４以上５０以下、０．０５以上５０以下、０．０６以上５０以下、０．０７以上５０以下、０．０８以上５０以下、又は０．０９以上５０以下であってもよい。前記含有量は、より好ましくは０．０５以上４０以下、更に好ましくは０．１以上３０以下、特に好ましくは０．１５以上２５以下、最も好ましくは１．０以上２０以下、特に最も好ましくは２．０以上１０以下である。当該比が前記される範囲であると、本発明の水添臭付与剤はより高い効率で食品に水添臭を付与できる。 The content ratio of cis-6-nonenal and trans-6-nonenal in the hydrogenated odorant of the present invention (content of cis-6-nonenal/content of trans-6-nonenal) is preferably It is 0.01 or more and 50 or less. The content is 0.02 or more and 50 or less, 0.03 or more and 50 or less, 0.04 or more and 50 or less, 0.05 or more and 50 or less, 0.06 or more and 50 or less, 0.07 or more and 50 or less, and 0.08 or more. It may be 50 or less, or 0.09 or more and 50 or less. The content is more preferably 0.05 or more and 40 or less, still more preferably 0.1 or more and 30 or less, particularly preferably 0.15 or more and 25 or less, most preferably 1.0 or more and 20 or less, and most preferably 2 .0 or more and 10 or less. When the ratio is within the range described above, the hydrogenated odor imparting agent of the present invention can impart hydrogenated odor to foods with higher efficiency.
＜油脂組成物＞
　本発明の限定されない任意の態様においては、本発明の水添臭付与剤は、油脂組成物の形態で提供されてよい。本発明の油脂組成物は、酸化油脂、米油、アマニ油、及び月見草油からなる群から選ばれる少なくとも１種と、シス－６－ノネナールと、トランス－６－ノネナールと、ベース油である食用油脂とを含む。本発明の油脂組成物は、必要に応じて任意に賦形剤、補助剤、乳化剤、ｐＨ調整剤等を配合して、公知の手法により、液体状、粉末状、ペースト状等の任意の形態の油脂組成物となし得る。すなわち、例えば、通常当業者に周知の製剤的技術により、食用油脂を主体とした、液体油脂、マーガリン、ファットスプレッド、ショートニング、粉末油脂等に調製されてもよく、あるいは、食用油脂の配合量が少ない溶液状、粉末状、ゲル状、顆粒状等に調製されてもよく、それら形態は任意に採用し得る。また、例えば、粉末化する場合には、コーンシロップ等の補助剤を使用することができ、更に、乳化剤を添加して乳化原料を調製したうえ、これを粉末化してもよい。粉末化の手段としては、スプレードライ、フリーズドライ等が挙げられる。 <Oil composition>
In any non-limiting embodiment of the present invention, the hydrogenated odorant of the present invention may be provided in the form of an oil or fat composition. The oil and fat composition of the present invention comprises at least one selected from the group consisting of oxidized oil, rice oil, linseed oil, and evening primrose oil, cis-6-nonenal, trans-6-nonenal, and an edible base oil. Contains oils and fats. The oil and fat composition of the present invention can be prepared in any form such as liquid, powder, paste, etc. by adding excipients, adjuvants, emulsifiers, pH adjusters, etc. as necessary and using known methods. It can be made into an oil and fat composition. That is, for example, liquid oils, margarines, fat spreads, shortenings, powdered oils, etc. mainly composed of edible oils and fats may be prepared by pharmaceutical techniques commonly known to those skilled in the art, or the amount of edible oils and fats may be adjusted. It may be prepared in the form of a small solution, powder, gel, granules, etc., and any form thereof may be adopted. For example, in the case of powdering, an auxiliary agent such as corn syrup may be used, and an emulsifying raw material may be prepared by adding an emulsifier, which may then be powdered. Examples of means for powdering include spray drying and freeze drying.
　本発明の油脂組成物が酸化油脂を含有する場合、当該酸化油脂については前記される通りである。また本発明の油脂組成物が含有する、酸化油脂、米油、アマニ油、及び月見草油からなる群から選ばれる少なくとも１種の含有量は、好ましくは１ｐｐｍ以上３００００ｐｐｍ以下、より好ましくは１００ｐｐｍ以上２５０００ｐｐｍ以下、更に好ましくは２５０ｐｐｍ以上２３０００ｐｐｍ以下、特に好ましくは５００ｐｐｍ以上２１０００ｐｐｍ以下である。当該含有量が前記される範囲であると、本発明の油脂組成物はより高い効率で食品に水添臭を付与できる。 When the oil and fat composition of the present invention contains an oxidized oil and fat, the oxidized oil and fat are as described above. Further, the content of at least one selected from the group consisting of oxidized oil, rice oil, linseed oil, and evening primrose oil contained in the oil and fat composition of the present invention is preferably 1 ppm to 30,000 ppm, more preferably 100 ppm to 25,000 ppm. The content is more preferably 250 ppm or more and 23,000 ppm or less, particularly preferably 500 ppm or more and 21,000 ppm or less. When the content is within the range described above, the oil and fat composition of the present invention can impart a hydrogenated odor to foods with higher efficiency.
　本発明の油脂組成物が含有するシス－６－ノネナール及びトランス－６－ノネナールについても前記される通りである。本発明の油脂組成物が含有するシス－６－ノネナールの含有量及びトランス－６－ノネナールの含有量のそれぞれは、好ましくは０．０１ｐｐｍ以上１０ｐｐｍ以下、より好ましくは０．０２ｐｐｍ以上８ｐｐｍ以下、更に好ましくは０．０３ｐｐｍ以上５ｐｐｍ以下、特に好ましくは０．０５ｐｐｍ以上３ｐｐｍ以下である。当該含有量が前記される範囲であると、本発明の油脂組成物はより高い効率で食品に水添臭を付与できる。
　本発明の油脂組成物が含有するシス－６－ノネナール及びトランス－６－ノネナールの合計含有量は、好ましくは０．１ｐｐｍ以上２０ｐｐｍ以下、より好ましくは０．１５ｐｐｍ以上１０ｐｐｍ以下、更に好ましくは０．２ｐｐｍ以上５ｐｐｍ以下、特に好ましくは０．２５ｐｐｍ以上２ｐｐｍ以下、最も好ましくは０．３ｐｐｍ以上１．５ｐｐｍ以下である。前記合計含有量が前記される範囲であると、本発明の油脂組成物はより高い効率で食品に水添臭を付与できる。 The cis-6-nonenal and trans-6-nonenal contained in the oil and fat composition of the present invention are also as described above. The content of cis-6-nonenal and the content of trans-6-nonenal contained in the oil and fat composition of the present invention are preferably 0.01 ppm or more and 10 ppm or less, more preferably 0.02 ppm or more and 8 ppm or less, and Preferably it is 0.03 ppm or more and 5 ppm or less, particularly preferably 0.05 ppm or more and 3 ppm or less. When the content is within the range described above, the oil and fat composition of the present invention can impart a hydrogenated odor to foods with higher efficiency.
The total content of cis-6-nonenal and trans-6-nonenal contained in the oil and fat composition of the present invention is preferably 0.1 ppm or more and 20 ppm or less, more preferably 0.15 ppm or more and 10 ppm or less, and even more preferably 0. It is 2 ppm or more and 5 ppm or less, particularly preferably 0.25 ppm or more and 2 ppm or less, and most preferably 0.3 ppm or more and 1.5 ppm or less. When the total content is within the above range, the oil and fat composition of the present invention can impart hydrogenated odor to foods with higher efficiency.
　本発明の油脂組成物が含有するベース油である食用油脂としては、例えば、菜種油（高オレイン酸タイプを含む）、大豆油、パーム油、パーム核油、コーン油、オリーブ油、ゴマ油、アマニ油、えごま油、紅花油、ヒマワリ油、綿実油、米油、落花生油、ヤシ油、シア脂、サル脂、カカオ脂、グレープシード油、マカダミアナッツオイル、ココナッツオイル、月見草油等の植物油脂、牛脂、豚脂、鶏脂、乳脂等の動物油脂、中鎖脂肪酸トリグリセリド等が挙げられる。加えて、これらの分別油（パーム油の中融点部、パーム油の軟質分別油、パーム油の硬質分別油等）、エステル交換油等の加工油脂等が挙げられる。食用油脂は、一種単独でも二種以上が混合されていてもよい。 The edible oils and fats that are the base oils contained in the oil and fat compositions of the present invention include, for example, rapeseed oil (including high oleic acid types), soybean oil, palm oil, palm kernel oil, corn oil, olive oil, sesame oil, linseed oil, Vegetable oils and fats such as perilla oil, safflower oil, sunflower oil, cottonseed oil, rice oil, peanut oil, coconut oil, shea butter, monkey fat, cacao butter, grapeseed oil, macadamia nut oil, coconut oil, evening primrose oil, beef tallow, pork Examples include animal fats and oils such as fat, chicken fat, and milk fat, medium-chain fatty acid triglycerides, and the like. In addition, processed oils and fats such as these fractionated oils (medium melting point part of palm oil, soft fractionated palm oil, hard fractionated palm oil, etc.), transesterified oil, and the like can be mentioned. Edible fats and oils may be used alone or in combination of two or more.
　本発明の油脂組成物には、食用に通常添加される助剤が適宜配合されていてもよい。助剤としては、酸化防止剤、消泡剤、乳化剤、香料、風味付与剤、色素、生理活性物質等が挙げられる。具体的には、例えば、アスコルビン酸脂肪酸エステル、リグナン、コエンザイムＱ、γ－オリザノール、トコフェロール、シリコーン等が挙げられる。 The fat and oil composition of the present invention may optionally contain auxiliary agents that are commonly added to edible foods. Examples of the auxiliary agents include antioxidants, antifoaming agents, emulsifiers, fragrances, flavoring agents, pigments, and physiologically active substances. Specific examples include ascorbic acid fatty acid ester, lignan, coenzyme Q, γ-oryzanol, tocopherol, and silicone.
　本発明の油脂組成物は、部分水素添加油脂を含んでいても、含んでいなくてもよいが、好ましくは硬化油、特に部分水素添加油脂を含まない。それによって、トランス脂肪酸を含まない組成となる。 The oil and fat composition of the present invention may or may not contain partially hydrogenated fats and oils, but preferably does not contain hydrogenated oils, particularly partially hydrogenated fats and oils. This results in a composition that does not contain trans fatty acids.
　本発明の油脂組成物の用途は特定の用途に限定されない。本発明の油脂組成物は、好ましくはフライ用油脂組成物として使用される。 The use of the oil and fat composition of the present invention is not limited to specific uses. The oil and fat composition of the present invention is preferably used as an oil and fat composition for frying.
＜油脂組成物の製造方法＞
　本発明の油脂組成物の製造方法は、酸化油脂、米油、アマニ油、及び月見草油からなる群から選ばれる少なくとも１種と、シス－６－ノネナールと、トランス－６－ノネナールとを、ベース油である食用油脂に添加する工程を含む。 <Method for producing oil and fat composition>
The method for producing an oil and fat composition of the present invention includes at least one selected from the group consisting of oxidized oil, rice oil, linseed oil, and evening primrose oil, cis-6-nonenal, and trans-6-nonenal as a base. It includes the process of adding to edible fats and oils.
　本発明の油脂組成物が前記酸化油脂を含む場合、前記の通り前記酸化油脂は前記原料となる食用油脂を酸化処理して得られる。本発明の油脂組成物の製造方法は、好ましくは前記酸化油脂の原料となる食用油脂に空気を供給しつつ加熱処理することにより、過酸化物価が１５以上３５０以下となるように酸化処理して前記酸化油脂を製造する工程を更に含む。 When the oil or fat composition of the present invention contains the oxidized oil or fat, the oxidized oil or fat is obtained by oxidizing the edible oil or fat used as the raw material, as described above. The method for producing an oil or fat composition of the present invention preferably includes oxidizing the edible oil or fat, which is a raw material for the oxidized oil, by heat-treating the edible oil or fat while supplying air so that the peroxide value becomes 15 or more and 350 or less. The method further includes a step of producing the oxidized fat.
　前記原料となる食用油脂を酸化処理する方法としては、上記所定範囲の過酸化物価に酸化処理することができる方法であればよく、特に制限はないが、好ましくは加熱処理する方法が挙げられる。例えば、工業的スケールで生産する観点からは、タンク等の適当な容器に原料油脂を収容したうえ、容器に備わる電熱式、直火バーナー式、マイクロ波式、蒸気式、熱風式などの加熱手段で行うことが好ましい。 The method of oxidizing the edible oil or fat used as the raw material may be any method as long as it can be oxidized to a peroxide value within the above-mentioned predetermined range, and is not particularly limited, but preferably includes a method of heat treatment. For example, from the perspective of production on an industrial scale, raw material oils and fats are stored in a suitable container such as a tank, and the container is equipped with a heating method such as an electric heating type, a direct flame burner type, a microwave type, a steam type, or a hot air type. It is preferable to do so.
　加熱処理の条件としては、特に制限はないが、加熱温度５０℃以上２２０℃以下で、加熱時間が０．１時間以上２４０時間以下で行うことが好ましく、加熱温度６０℃以上１６０℃以下で、加熱時間が１時間以上１００時間以下で行うことがより好ましい。また、加熱温度（℃）×加熱時間（時間）の積算量の条件としては、好ましくは２００以上２００００以下であり、より好ましくは２２０以上１８０００以下であり、更に好ましくは２４０以上１５０００以下である。なお、加熱温度を変化させた場合、加熱温度（℃）×加熱時間（時間）の積算量は、温度を変化させる前の加熱温度（℃）×温度を変化させる前の加熱時間（時間）＋温度を変化させた後の加熱温度（℃）×温度を変化させた後の加熱時間（時間）、又は加熱時間（時間）にわたる加熱温度（℃）の積分値として算出することができる。 There are no particular restrictions on the conditions for the heat treatment, but it is preferable that the heating temperature is 50°C or more and 220°C or less, and the heating time is 0.1 hour or more and 240 hours or less, and the heating temperature is 60°C or more and 160°C or less, More preferably, the heating time is 1 hour or more and 100 hours or less. Further, the cumulative amount of heating temperature (°C) x heating time (hours) is preferably 200 or more and 20,000 or less, more preferably 220 or more and 18,000 or less, and even more preferably 240 or more and 15,000 or less. When changing the heating temperature, the cumulative amount of heating temperature (°C) x heating time (hours) is: heating temperature (°C) before changing the temperature x heating time (hours) before changing the temperature + It can be calculated as the heating temperature (°C) after changing the temperature x the heating time (hours) after changing the temperature, or the integral value of the heating temperature (°C) over the heating time (hours).
　加熱処理に際しては、撹拌により容器の開放スペースから酸素を取り入れたり、酸素を吹き込んだりして、酸素を供給してもよい。酸素源は空気などを用いてもよい。これにより前記原料となる食用油脂の酸化が促進される。その場合、酸素の供給量としては、前記食用油脂１ｋｇあたり０．００１Ｌ／分以上２Ｌ／分以下となる範囲とすることが好ましい。例えば、空気の場合は、上記油脂１ｋｇあたり０．００５Ｌ／分以上１０Ｌ／分以下となる範囲とすることが好ましく、０．０１Ｌ／分以上５Ｌ／分以下となる範囲とすることがより好ましい。 During the heat treatment, oxygen may be supplied by taking in oxygen from the open space of the container by stirring or by blowing oxygen into the container. Air or the like may be used as the oxygen source. This promotes the oxidation of the edible oil and fat used as the raw material. In that case, the amount of oxygen supplied is preferably in a range of 0.001 L/min or more and 2 L/min or less per 1 kg of the edible fat or oil. For example, in the case of air, the flow rate is preferably in the range of 0.005 L/min or more and 10 L/min or less, and more preferably 0.01 L/min or more and 5 L/min or less per 1 kg of the fat or oil.
＜水添臭付与剤及び油脂組成物の応用＞
　本発明の食品に水添臭を付与する方法は、酸化油脂、米油、アマニ油、及び月見草油からなる群から選ばれる少なくとも１種と、シス－６－ノネナールと、トランス－６－ノネナールとを食品に添加する工程を含む。本発明の食品に水添臭を付与する方法では、例えば、本発明の水添臭付与剤又は本発明の油脂組成物を食品へ添加する。 <Application of hydrogenated odor imparting agent and oil/fat composition>
The method of imparting a hydrogenated odor to foods of the present invention includes at least one selected from the group consisting of oxidized fats and oils, rice oil, linseed oil, and evening primrose oil, cis-6-nonenal, and trans-6-nonenal. It includes the process of adding to food. In the method of imparting a hydrogenated odor to foods of the present invention, for example, the hydrogenated odor imparting agent of the present invention or the fat composition of the present invention is added to foods.
　添加方法は特に限定されず、例えば、本発明の水添臭付与剤又は本発明の油脂組成物がそのまま食品に添加されてもよいし、本発明の油脂組成物を風味油の形態としてから食品に添加されてもよい。また、本発明の水添臭付与剤が添加された食用油脂又は本発明の油脂組成物を用いて揚げ種を油ちょうしてもよく、油ちょうされた食品（フライ食品）に独特の甘い香りを感じさせる風味を付与することができる。 The method of addition is not particularly limited; for example, the hydrogenated odor imparting agent of the present invention or the oil/fat composition of the present invention may be added to foods as is, or the oil/fat composition of the present invention may be made into a flavored oil and then added to foods. may be added to. Furthermore, fried seeds may be fried using the edible oil or fat to which the hydrogenated odor-imparting agent of the present invention has been added or the oil and fat composition of the present invention, giving the fried food (fried food) a unique sweet aroma. It can give a pleasant flavor.
　本発明の水添臭付与剤又は油脂組成物が添加される食品は特に限定されないが、例えば、
食用油脂；
マーガリン、スプレッド、バター、マヨネーズ、ドレッシング、クリーム等の油脂加工食品（食用油脂を原料として含有する食品を指す）；
牛乳、豆乳、乳飲料、乳酸飲料、スポーツ飲料等の飲料；
ドーナツ、クッキー、パイ、ケーキ、マドレーヌ、ゼリー、プディング、ムース、チョコレート、グミ等の菓子類；
菓子パン等のパン類；
そば、うどん、ラーメン、パスタ等の麺類；
炒飯等の米飯類；
チーズ、バター、ヨーグルト等の乳製品；
ハンバーグ、ハム、ソーセージ等の畜肉加工食品；
ちくわ、蒲鉾等の水産加工食品；
コーンスープ、コンソメスープ、ポタージュ等のスープ類；
中華の素、焼き肉のタレ等の調味料類やソース類；
冷凍食品、煮物、揚げ物、焼き物、健康食品等が挙げられる。本発明の水添臭付与剤が添加される食品は、好ましくは食用油脂及び油脂加工食品の少なくとも１種であり、より好ましくは食用油脂である。 Foods to which the hydrogenated odorant or fat composition of the present invention is added are not particularly limited, but include, for example:
Edible fats and oils;
Processed oil and fat foods such as margarine, spreads, butter, mayonnaise, dressings, and creams (referring to foods that contain edible oils and fats as raw materials);
Beverages such as milk, soy milk, milk drinks, lactic acid drinks, sports drinks;
Confectionery such as donuts, cookies, pies, cakes, madeleines, jellies, puddings, mousses, chocolates, and gummies;
Bread such as sweet bread;
Noodles such as soba, udon, ramen, and pasta;
Rice such as fried rice;
Dairy products such as cheese, butter, and yogurt;
Processed meat foods such as hamburgers, hams, and sausages;
Processed seafood foods such as chikuwa and kamaboko;
Soups such as corn soup, consommé soup, and potage;
Seasonings and sauces such as Chinese ingredients and grilled meat sauce;
Examples include frozen foods, boiled foods, fried foods, grilled foods, and health foods. The food to which the hydrogenated odor imparting agent of the present invention is added is preferably at least one of edible fats and oils and processed fats and oils, more preferably edible fats and oils.
　本発明のフライ食品の製造方法は、酸化油脂、米油、アマニ油、及び月見草油からなる群から選ばれる少なくとも１種と、シス－６－ノネナールと、トランス－６－ノネナールとを、ベース油である食用油脂に添加し、油脂組成物を製造する工程と、当該油脂組成物を用いて揚げ種を油ちょうする工程を含む。 The method for producing fried foods of the present invention includes adding at least one selected from the group consisting of oxidized oil, rice oil, linseed oil, and evening primrose oil, cis-6-nonenal, and trans-6-nonenal to a base oil. The method includes a step of adding to an edible fat and oil to produce an oil and fat composition, and a step of frying fried seeds using the oil and fat composition.
　前記フライ食品として、特に限定されないが、例えば、ドーナツ、揚げパン、カレーパン、ピロシキ、アメリカンドッグ、クルトン、かりんとう、揚げ米菓、スナック菓子、フリッター類、トンカツ、チキンカツ、唐揚げ、フライドチキン、魚フライ、天ぷら、コロッケ、メンチカツ、ポテトフライ、チキンナゲット、ハッシュドポテト、揚げ豆腐、インスタントラーメン等が挙げられる。 Examples of the fried foods include, but are not limited to, donuts, fried bread, curry bread, piroshki, corn dogs, croutons, karinto, fried rice crackers, snacks, fritters, pork cutlets, chicken cutlets, fried chicken, fried chicken, and fried fish. , tempura, croquettes, minced meat cutlets, fries, chicken nuggets, hash browns, fried tofu, instant ramen, etc.
　以下、本発明を実施例に基づき更に詳細に説明するが、本発明はこれらに限定されるものではない。 Hereinafter, the present invention will be explained in more detail based on Examples, but the present invention is not limited thereto.
　実施例、比較例及び対照例において、３名のパネルが下記各ドーナツを、4名のパネルが下記各フライドチキンを喫食し、下記基準に従って下記各ドーナツ及び下記各フライドチキンの水添臭を評価した。
－水添臭評価の基準－
　Ａ：対照例（部分水素添加油脂を使用した場合）にとても近い風味である。
　Ｂ：対照例（部分水素添加油脂を使用した場合）に近い風味である。
　Ｃ：対照例（部分水素添加油脂を使用した場合）にやや近い風味である。
　Ｄ：対照例（部分水素添加油脂を使用した場合）に近い風味ではない。 In the Examples, Comparative Examples, and Control Examples, three panels ate the donuts below, and four panels ate the fried chicken below, and evaluated the hydrogenated odor of each donut and fried chicken below according to the criteria below. did.
- Standards for hydrogenation odor evaluation -
A: The flavor is very similar to the control example (when partially hydrogenated oil and fat was used).
B: Flavor similar to the control example (when partially hydrogenated oil and fat was used).
C: Flavor somewhat similar to the control example (when partially hydrogenated oil and fat was used).
D: The flavor is not close to that of the control example (when partially hydrogenated oil and fat was used).
実施例１～２５及び比較例１～４
　精製パーム油（株式会社Ｊ－オイルミルズ社製）６０質量％及びエステル交換油（当該エステル交換油は、国際公開第２０２０／００４０５８号に記載の［実施例］で調製されたエステル交換油脂１に準じて調製された。具体的には、パームステアリン（ヨウ素価３５）７５質量％、パーム油１０質量％、及び大豆油１５質量％の含有量で混合された後、ナトリウムメトキシドを触媒としたエステル交換が行われ、更に精製されて調製された）４０質量％からなる混合油をベース油として用い、そのベース油に対して表１～６に示す濃度となるように、各成分を添加して各油脂組成物を調製した。市販のドーナツ原料（日本食研株式会社製ドーナツボールミックス）１００質量部に水３０質量部を加えて混合し、得られた生地がしっとりひとまとまりになるまで手で混ぜた。当該ドーナツ生地の適量を丸く成形し、前記各油脂組成物を用いて１６０℃で５分間油ちょうした。結果を表１～６に示す。 Examples 1 to 25 and Comparative Examples 1 to 4
Refined palm oil (manufactured by J-Oil Mills Co., Ltd.) 60% by mass and transesterified oil (the transesterified oil is transesterified fat 1 prepared in [Example] described in International Publication No. 2020/004058) Specifically, after mixing 75% by mass of palm stearin (iodine value 35), 10% by mass of palm oil, and 15% by mass of soybean oil, the mixture was prepared using sodium methoxide as a catalyst. A mixed oil consisting of 40% by mass (prepared by transesterification and further refinement) was used as the base oil, and each component was added to the base oil to the concentration shown in Tables 1 to 6. Each oil and fat composition was prepared. 30 parts by mass of water was added to 100 parts by mass of a commercially available donut raw material (donut ball mix manufactured by Nihon Shokuken Co., Ltd.) and mixed, and the resulting dough was mixed by hand until it became a moist ball. An appropriate amount of the donut dough was shaped into a round shape and fried with each of the above-mentioned oil and fat compositions at 160° C. for 5 minutes. The results are shown in Tables 1-6.
比較例５
　前記ベース油のみからなる油脂組成物を用いて、前記ドーナツ生地を前記ドーナツ生地と同様に油ちょうした。結果を表６に示す。 Comparative example 5
The donut dough was fried in the same manner as the donut dough using the oil and fat composition consisting only of the base oil. The results are shown in Table 6.
対照例１
　前記精製パーム油６０質量％及び菜種水添脂（株式会社Ｊ－オイルミルズ製）４０質量％からなる油脂組成物を用いて、前記ドーナツ生地を前記ドーナツ生地と同様に油ちょうした。結果を表６に示す。 Control example 1
The donut dough was fried in the same manner as the donut dough using an oil and fat composition consisting of 60% by mass of the refined palm oil and 40% by mass of hydrogenated rapeseed fat (manufactured by J-Oil Mills Co., Ltd.). The results are shown in Table 6.
Figure JPOXMLDOC01-appb-T000001
Figure JPOXMLDOC01-appb-T000001
Figure JPOXMLDOC01-appb-T000002
Figure JPOXMLDOC01-appb-T000002
Figure JPOXMLDOC01-appb-T000003
Figure JPOXMLDOC01-appb-T000003
Figure JPOXMLDOC01-appb-T000004
Figure JPOXMLDOC01-appb-T000004
Figure JPOXMLDOC01-appb-T000005
Figure JPOXMLDOC01-appb-T000005
Figure JPOXMLDOC01-appb-T000006
Figure JPOXMLDOC01-appb-T000006
１）Sundia MediTech Company社製
２）シグマアドリッチ社製
３）シス－６－ノネナールの含有量／トランス－６－ノネナールの含有量
４）無水乳脂（丸和油脂株式会社製バターオイルＣＭＬ、油脂含量９９．８質量％）２５０ｇをビーカーに入れ、これに０．２５Ｌ／分の量の空気を供給しつつ、オイルバス中、撹拌速度２００ｒｐｍで攪拌しながら、１００℃及び２５時間の条件で加熱処理を施した。得られた酸化油脂のＰＯＶは８５．５だった。
５）アラキドン酸含有トリグリセリド（サントリー株式会社製SUNTGA40S（微生物由来アラキドン酸、アラキドン酸純度４０～４５質量％、トリグリセリド純度９５質量％以上）２５質量％と、パームオレイン（株式会社Ｊ－オイルミルズ製IV67）７５質量％からなる混合物２５０ｇをビーカーに入れ、これに０．２５Ｌ／分の量の空気を供給しつつ、オイルバス中、撹拌速度２００ｒｐｍで攪拌しながら、９５℃及び１５時間の条件で加熱処理を施した。得られた酸化油脂のＰＯＶは１２６だった。
６）ハイオレヒマワリ油（株式会社Ｊ－オイルミルズ製、構成脂肪酸総量に占めるオレイン酸含有量８３．７質量％）２５０ｇをビーカーに入れ、これに０．２５Ｌ／分の量の空気を供給しつつ、オイルバス中、撹拌速度２００ｒｐｍで攪拌しながら、１００～１０５℃及び３８時間の条件で加熱処理を施した。得られた酸化油脂のＰＯＶは１０７だった。
７）米胚芽油（築野食品工業株式会社製）
８）あまに油（株式会社Ｊ－オイルミルズ製）
９）月見草油（株式会社長白工房製）
　なお、各酸化油脂のＰＯＶは「基準油脂分析試験法２．５．２過酸化物価」に則って測定された値である。 1) Manufactured by Sundia MediTech Company 2) Manufactured by Sigma Adrich 3) Content of cis-6-nonenal/content of trans-6-nonenal 4) Anhydrous milk fat (butter oil CML manufactured by Maruwa Yushi Co., Ltd., fat content 99 .8 mass%) was placed in a beaker, and while supplying air at an amount of 0.25 L/min, heat treatment was performed at 100 ° C. for 25 hours while stirring at a stirring speed of 200 rpm in an oil bath. provided. The POV of the obtained oxidized fat was 85.5.
5) 25% by mass of arachidonic acid-containing triglyceride (SUNTGA40S manufactured by Suntory Ltd. (arachidonic acid derived from microorganisms, arachidonic acid purity 40-45% by mass, triglyceride purity 95% by mass or more) and palm olein (IV67 manufactured by J-Oil Mills Ltd.) ) 75% by mass was placed in a beaker and heated at 95°C for 15 hours while supplying 0.25 L/min of air and stirring at a stirring speed of 200 rpm in an oil bath. The POV of the obtained oxidized oil and fat was 126.
6) Put 250 g of high-ole sunflower oil (manufactured by J-Oil Mills Co., Ltd., oleic acid content 83.7% by mass based on the total amount of constituent fatty acids) into a beaker, and supply air at an amount of 0.25 L/min to it. At the same time, heat treatment was performed at 100 to 105° C. for 38 hours while stirring at a stirring speed of 200 rpm in an oil bath. The POV of the obtained oxidized fat was 107.
7) Rice germ oil (manufactured by Tsukino Foods Co., Ltd.)
8) Linseed oil (manufactured by J-Oil Mills Co., Ltd.)
9) Evening primrose oil (manufactured by Chohaku Kobo Co., Ltd.)
The POV of each oxidized fat and oil is a value measured in accordance with "Standard Oil and Fat Analysis Test Method 2.5.2 Peroxide Value".
　シス－６－ノネナールを含まない比較例１～４の油脂組成物を用いて油ちょうされたドーナツは、対照例１の油脂組成物を用いて油ちょうされた対照ドーナツにやや近い風味であった、ないし当該対照ドーナツに近い風味でなかった。
　シス－６－ノネナール及びトランス－６－ノネナールを含まない比較例５の油脂組成物を用いて油ちょうされたドーナツは、前記対照ドーナツに近い風味でなかった。
　一方、実施例１～２５の油脂組成物を用いて油ちょうされたドーナツは、前記対照ドーナツにとても近い風味、ないし近い風味であった。 The donuts fried with oil and fat compositions of Comparative Examples 1 to 4 that did not contain cis-6-nonenal had a flavor somewhat similar to the control donuts that were fried with the oil and fat composition of Comparative Example 1. , or the flavor was not close to that of the control donut.
The donuts fried with the oil and fat composition of Comparative Example 5 that did not contain cis-6-nonenal and trans-6-nonenal did not have a flavor similar to the control donut.
On the other hand, the donuts fried using the oil and fat compositions of Examples 1 to 25 had a flavor very similar to or similar to the control donut.
実施例２６～３２及び比較例６
　菜種油（株式会社Ｊ－オイルミルズ社製）をベース油として用い、そのベース油に対して表７及び表８に示す濃度となるように、各成分を添加して各油脂組成物を調製した。当該各油脂組成物を用いて市販のフライドチキン（味の素冷凍食品株式会社製骨なしフライドチキン）を１８０℃で５分３０秒間油ちょうした。結果を表７及び表８に示す。 Examples 26 to 32 and Comparative Example 6
Using rapeseed oil (manufactured by J-Oil Mills Co., Ltd.) as a base oil, each oil and fat composition was prepared by adding each component to the base oil so as to have the concentrations shown in Tables 7 and 8. Using each of the oil and fat compositions, commercially available fried chicken (boneless fried chicken manufactured by Ajinomoto Frozen Foods Co., Ltd.) was fried at 180° C. for 5 minutes and 30 seconds. The results are shown in Tables 7 and 8.
比較例７
　前記ベース油のみからなる油脂組成物を用いて、前記市販のフライドチキンを前記フライドチキンと同様に油ちょうした。結果を表８に示す。 Comparative example 7
The commercially available fried chicken was fried in the same manner as the fried chicken using the oil and fat composition consisting only of the base oil. The results are shown in Table 8.
対照例２
　前記精製パーム油６０質量％及び菜種水添脂（株式会社Ｊ－オイルミルズ製）４０質量％からなる油脂組成物を用いて、前記市販のフライドチキンを前記フライドチキンと同様に油ちょうした。結果を表８に示す。 Control example 2
The commercially available fried chicken was fried in the same manner as the fried chicken using an oil and fat composition consisting of 60% by mass of the purified palm oil and 40% by mass of hydrogenated rapeseed fat (manufactured by J-Oil Mills Co., Ltd.). The results are shown in Table 8.
Figure JPOXMLDOC01-appb-T000007
Figure JPOXMLDOC01-appb-T000007
Figure JPOXMLDOC01-appb-T000008
Figure JPOXMLDOC01-appb-T000008
１０）アラキドン酸含有トリグリセリド（サントリー株式会社製SUNTGA40S（微生物由来アラキドン酸、アラキドン酸純度４０～４５質量％、トリグリセリド純度９５質量％以上）２５０ｇをビーカーに入れ、これに０．２５Ｌ／分の量の空気を供給しつつ、オイルバス中、撹拌速度２００ｒｐｍで攪拌しながら、９５℃及び１５時間の条件で加熱処理を施した。得られた酸化油脂のＰＯＶは１８９だった。
１１）マカダミアナッツ油（サミット製油株式会社製）２５０ｇをビーカーに入れ、これに０．２５Ｌ／分の量の空気を供給しつつ、オイルバス中、撹拌速度２００ｒｐｍで攪拌しながら、１００～１０５℃及び３０時間の条件で加熱処理を施した。得られた酸化油脂ＰＯＶは９８だった。 10) Put 250 g of arachidonic acid-containing triglyceride (SUNTGA40S manufactured by Suntory Ltd. (arachidonic acid derived from microorganisms, arachidonic acid purity 40-45% by mass, triglyceride purity 95% by mass or more) into a beaker, and add 0.25L/min. Heat treatment was performed at 95°C for 15 hours while supplying air and stirring at a stirring speed of 200 rpm in an oil bath.The POV of the obtained oxidized fat was 189.
11) Put 250 g of macadamia nut oil (manufactured by Summit Oil Co., Ltd.) into a beaker, and while supplying air at a rate of 0.25 L/min, heat the oil to 100 to 105°C while stirring at a stirring speed of 200 rpm in an oil bath. Heat treatment was performed under the following conditions: and 30 hours. The obtained oxidized fat POV was 98.
　シス－６－ノネナール及びトランス－６－ノネナールを含まない比較例６及び７の油脂組成物を用いて油ちょうされたフライドチキンは、対照例２の油脂組成物を用いて油ちょうされた対照フライドチキンに近い風味でなかった。
　一方、実施例２６～３２の油脂組成物を用いて油ちょうされたフライドチキンは、前記対照フライドチキンにとても近い風味、ないし近い風味であった。 The fried chicken fried with oil and fat compositions of Comparative Examples 6 and 7, which do not contain cis-6-nonenal and trans-6-nonenal, is different from the control fried chicken that is fried with oil and fat composition of Comparative Example 2. It didn't taste like chicken.
On the other hand, the fried chicken fried using the oil and fat compositions of Examples 26 to 32 had a flavor very similar to or similar to that of the control fried chicken.

Claims (17)

  1. 　酸化油脂、米油、アマニ油、及び月見草油からなる群から選ばれる少なくとも１種と、シス－６－ノネナールと、トランス－６－ノネナールとを有効成分として含む、水添臭付与剤。 A hydrogenated odor-imparting agent containing as active ingredients at least one selected from the group consisting of oxidized fats and oils, rice oil, linseed oil, and evening primrose oil, cis-6-nonenal, and trans-6-nonenal.
  2. 　前記シス－６－ノネナールと前記トランス－６－ノネナールとの含有量の比が０．０１以上５０以下である、請求項１に記載の水添臭付与剤。 The hydrogenated odor imparting agent according to claim 1, wherein the content ratio of the cis-6-nonenal to the trans-6-nonenal is 0.01 or more and 50 or less.
  3. 　前記酸化油脂を含み、前記酸化油脂の過酸化物価が１５以上３５０以下である、請求項１又は２に記載の水添臭付与剤。 The hydrogenated odor-imparting agent according to claim 1 or 2, which contains the oxidized fat and has a peroxide value of 15 or more and 350 or less.
  4. 　前記酸化油脂を含み、前記酸化油脂が乳脂、アラキドン酸含有油脂、ヒマワリ油、及びマカダミアナッツオイルからなる群から選ばれる少なくとも１種の酸化油脂である、請求項１又は２に記載の水添臭付与剤。 The hydrogenated odor according to claim 1 or 2, which contains the oxidized oil and fat, and the oxidized oil is at least one oxidized oil and fat selected from the group consisting of milk fat, arachidonic acid-containing oil, sunflower oil, and macadamia nut oil. Imparting agent.
  5. 　酸化油脂、米油、アマニ油、及び月見草油からなる群から選ばれる少なくとも１種と、シス－６－ノネナールと、トランス－６－ノネナールと、ベース油である食用油脂とを含むことを特徴とする油脂組成物。 It is characterized by containing at least one selected from the group consisting of oxidized oil, rice oil, linseed oil, and evening primrose oil, cis-6-nonenal, trans-6-nonenal, and an edible oil or fat as a base oil. An oil and fat composition.
  6. 　前記シス－６－ノネナールの含有量が０．０１ｐｐｍ以上１０ｐｐｍ以下であり、前記トランス－６－ノネナールの含有量が０．０１ｐｐｍ以上１０ｐｐｍ以下である、請求項５に記載の油脂組成物。 The oil and fat composition according to claim 5, wherein the content of the cis-6-nonenal is 0.01 ppm or more and 10 ppm or less, and the content of the trans-6-nonenal is 0.01 ppm or more and 10 ppm or less.
  7. 　前記酸化油脂を含み、前記酸化油脂の過酸化物価が１５以上３５０以下である、請求項５又は６に記載の油脂組成物。 The oil or fat composition according to claim 5 or 6, which contains the oxidized oil and fat and has a peroxide value of 15 or more and 350 or less.
  8. 　前記酸化油脂を含み、前記酸化油脂が乳脂、アラキドン酸含有油脂、ヒマワリ油、及びマカダミアナッツオイルからなる群から選ばれる少なくとも１種の酸化油脂である、請求項５又は６に記載の油脂組成物。 The oil or fat composition according to claim 5 or 6, which contains the oxidized oil and fat, and the oxidized oil is at least one oxidized oil and fat selected from the group consisting of milk fat, arachidonic acid-containing oil, sunflower oil, and macadamia nut oil. .
  9. 　前記酸化油脂、米油、アマニ油、及び月見草油からなる群から選ばれる少なくとも１種の含有量が１ｐｐｍ以上３００００ｐｐｍ以下である、請求項５又は６に記載の油脂組成物。 The oil or fat composition according to claim 5 or 6, wherein the content of at least one selected from the group consisting of the oxidized oil, rice oil, linseed oil, and evening primrose oil is 1 ppm or more and 30,000 ppm or less.
  10. 　フライ用である、請求項５又は６に記載の油脂組成物。 The oil and fat composition according to claim 5 or 6, which is for frying.
  11. 　酸化油脂、米油、アマニ油、及び月見草油からなる群から選ばれる少なくとも１種と、シス－６－ノネナールと、トランス－６－ノネナールとを、ベース油である食用油脂に添加する工程を含むことを特徴とする油脂組成物の製造方法。 Includes a step of adding at least one selected from the group consisting of oxidized oil, rice oil, linseed oil, and evening primrose oil, cis-6-nonenal, and trans-6-nonenal to an edible oil or fat that is a base oil. A method for producing an oil and fat composition, characterized by:
  12. 　前記酸化油脂の原料となる食用油脂に空気を供給しつつ加熱処理することにより、過酸化物価が１５以上３５０以下となるように酸化処理して前記酸化油脂を製造する工程を更に含む、請求項１１に記載の油脂組成物の製造方法。 Claim further comprising the step of producing the oxidized fat by oxidizing the edible fat, which is a raw material for the oxidized fat, by heat-treating it while supplying air so that the peroxide value is 15 or more and 350 or less. 12. The method for producing an oil or fat composition according to 11.
  13. 　前記酸化油脂の原料となる食用油脂は、乳脂、アラキドン酸含有油脂、ヒマワリ油、及びマカダミアナッツオイルからなる群から選ばれる少なくとも１種である、請求項１１又は１２に記載の油脂組成物の製造方法。 The production of an oil or fat composition according to claim 11 or 12, wherein the edible oil or fat that is a raw material for the oxidized oil or fat is at least one selected from the group consisting of milk fat, arachidonic acid-containing oil, sunflower oil, and macadamia nut oil. Method.
  14. 　前記酸化処理における空気の供給量が前記食用油脂１ｋｇあたり０．００５Ｌ／分以上１０Ｌ／分以下である、請求項１２に記載の油脂組成物の製造方法。 The method for producing an oil or fat composition according to claim 12, wherein the amount of air supplied in the oxidation treatment is 0.005 L/min or more and 10 L/min or less per 1 kg of the edible fat or oil.
  15. 　前記酸化処理における加熱温度が５０℃以上２２０℃以下である、請求項１２に記載の油脂組成物の製造方法。 The method for producing an oil or fat composition according to claim 12, wherein the heating temperature in the oxidation treatment is 50°C or more and 220°C or less.
  16. 　酸化油脂、米油、アマニ油、及び月見草油からなる群から選ばれる少なくとも１種と、シス－６－ノネナールと、トランス－６－ノネナールとを食品に添加する工程を含む、食品に水添臭を付与する方法。 A step of adding at least one member selected from the group consisting of oxidized oil, rice oil, linseed oil, and evening primrose oil, cis-6-nonenal, and trans-6-nonenal to the food, which produces a hydrogenated odor in the food. How to grant.
  17. 　フライ食品の製造方法であって、
    　酸化油脂、米油、アマニ油、及び月見草油からなる群から選ばれる少なくとも１種と、シス－６－ノネナールと、トランス－６－ノネナールとを、ベース油である食用油脂に添加し、油脂組成物を製造する工程と、
    　当該油脂組成物を用いて揚げ種を油ちょうする工程を含む、フライ食品の製造方法。     A method for producing a fried food, the method comprising:
    At least one selected from the group consisting of oxidized fats and oils, rice oil, linseed oil, and evening primrose oil, cis-6-nonenal, and trans-6-nonenal are added to edible fats and oils as a base oil, and the fat composition is adjusted. The process of manufacturing things,
    A method for producing a fried food, comprising the step of frying fried seeds in oil using the oil and fat composition.
PCT/JP2023/013897 2022-04-13 2023-04-04 Hydrogenation odor–imparting agent, fat and oil composition, production method for fat and oil composition, method for imparting hydrogenation odor to food, method for producing fried food WO2023199789A1 (en)

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Citations (3)

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CN101124979A (en) * 2007-08-31 2008-02-20 张之涤 Natural dairy spice and preparation method thereof
JP2009089684A (en) * 2007-10-11 2009-04-30 Nisshin Oillio Group Ltd Low trans-fatty acid oil and fat composition
WO2014167957A1 (en) * 2013-04-10 2014-10-16 長谷川香料株式会社 Agent for imparting hardened oil flavor

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CN101124979A (en) * 2007-08-31 2008-02-20 张之涤 Natural dairy spice and preparation method thereof
JP2009089684A (en) * 2007-10-11 2009-04-30 Nisshin Oillio Group Ltd Low trans-fatty acid oil and fat composition
WO2014167957A1 (en) * 2013-04-10 2014-10-16 長谷川香料株式会社 Agent for imparting hardened oil flavor

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