Oil-based emulsions in water

Abstract

To provide an oil-in-water emulsion composition that contains a diacylglycerol-containing fat containing an abundance of α-linolenic acid, and a vitamin C fatty acid ester C and has high oxidation stability but has a fishy or nasty odor reduced.SOLUTION: An oil-in-water emulsion composition contains components (A), (B), and (C): (A) a fat that contains at least 15 mass% of diacylglycerol and at least 15 mass% of α-linolenic acid in fatty acids constituting the fat; (B) 0.020-1.0 mass% of a vitamin C fatty acid ester relative to component (A); and (C) 0.15-6.0 mass% of a hydroxy acid or a salt thereof.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to an oil-in-water emulsion composition and a powdered oil or fat. [Background technology]

[0002] α-Linolenic acid (C18:3, ALA), which is abundant in flaxseed, is known to be converted into the highly physiologically active eicosapentaenoic acid (C20:5) and docosahexaenoic acid (C22:6) upon ingestion, and in recent years, there has been a demand for the use of oils and fats rich in this acid. However, oils and fats rich in α-linolenic acid have very low oxidative stability and easily produce unpleasant odors. For this reason, antioxidants such as tocopherol, rosemary extract, ascorbic acid fatty acid esters, catechin, and lecithin are typically added to oils and fats to prevent deterioration of the oil's flavor.

[0003] On the other hand, it has been reported that fats and oils containing high concentrations of diacylglycerol have physiological effects such as suppressing the increase in blood triglycerides (neutral fats) after eating and reducing accumulation in the body. Therefore, various functional oils and fats rich in α-linolenic acid and diacylglycerol have been proposed to effectively express the physiologically active functions of α-linolenic acid and diacylglycerol (for example, Patent Document 1).

[0004] Edible oils and fats come in the form of oil-in-water (O / W) emulsions and powdered oils, which are dried and powdered. Powdered oils and fats have the advantage of quickly dissolving and dispersing in water, and when used in food, they can bring various effects, such as adding flavor and improving texture. For example, Patent Document 2 proposes a powdered oil containing a glyceride mixture containing 15 to 94.9% by weight of diglycerides, with 50% by weight or more of the total constituent fatty acids being unsaturated fatty acids, a powdered base material, and water, and having excellent flavor and re-dispersibility in water. Patent Document 3 proposes a powdered oil containing highly unsaturated fatty acid-containing oils, edible proteins, edible carbohydrates, and an edible antioxidant, having excellent water dispersibility and little oxidative deterioration odor over time. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Japanese Patent Application Laid-Open No. 2002-138297 [Patent Document 2] Japanese Patent Application Laid-Open No. 2003-306693 [Patent Document 3] Japanese Patent Application Publication No. 2019-41721 Summary of the Invention [Problem to be solved by the invention]

[0006] According to the present inventors, vitamin C fatty acid esters are suitable additives that can suppress the deterioration of flavor caused by oxidation, particularly photooxidation, of diacylglycerol-containing fats and oils that are rich in α-linolenic acid. However, when an attempt was made to prepare an oil-in-water emulsion composition by blending a diacylglycerol-containing oil rich in α-linolenic acid with a vitamin C fatty acid ester, it was found that although oxidation stability could be imparted to the oil-in-water emulsion composition, a fishy odor and a fishy smell, which were different from the unpleasant odor generated by oxidation of the oil, were generated immediately after preparation of the oil-in-water emulsion composition. Therefore, the present invention relates to an oil-in-water emulsion composition that contains a diacylglycerol-containing oil rich in α-linolenic acid and a vitamin C fatty acid ester, and that has high oxidation stability while having little fishy or fishy odor. [Means for solving the problem]

[0007] As a result of extensive research to solve the above problems, the present inventors have found that even when a diacylglycerol-containing oil rich in α-linolenic acid and a vitamin C fatty acid ester are used, if a hydroxy acid or a salt thereof is added in a certain range and emulsified, an oil-in-water emulsion composition and a powdered oil that are oxidatively stable and have little fishy or fishy odor can be obtained.

[0008] That is, the present invention provides a composition comprising the following components (A), (B) and (C): (A) Oils and fats having a diacylglycerol content of 15% by mass or more and an α-linolenic acid content of 15% by mass or more among the fatty acids constituting the oils and fats (B) Vitamin C fatty acid ester: 0.020 to 1.0% by mass of component (A) (C) Hydroxy acid or its salt 0.15 to 6.0% by mass The present invention provides an oil-in-water emulsion composition comprising: The present invention also provides a powdered oil or fat obtained by drying the oil-in-water emulsion composition. [Effects of the Invention]

[0009] According to the present invention, it is possible to provide an oil-in-water emulsion composition and powdered oil that have high oxidation stability, little fishy or raw odor, and high functionality of α-linolenic acid and diacylglycerol. DETAILED DESCRIPTION OF THE INVENTION

[0010] The oil-in-water emulsion composition of the present invention contains (A) an oil or fat having a diacylglycerol content of 15% by mass or more and an α-linolenic acid content of 15% by mass or more among the fatty acids constituting the oil or fat. In this specification, the oil or fat refers to one or more of monoacylglycerol, diacylglycerol, and triacylglycerol. There are no particular limitations on the type of oil or fat, and any oil or fat that can be used as an edible oil or fat may be used. Hereinafter, in this specification, "(A) fats and oils having a diacylglycerol content of 15% by mass or more and an α-linolenic acid content of 15% by mass or more among the fatty acids constituting the fats and oils" will also be referred to as "component (A) fats and oils." In the present invention, the content of α-linolenic acid in the fatty acids constituting the oil or fat of component (A) is 15% by mass (hereinafter simply referred to as "%") or more. From the viewpoint of physiological effects, the content of α-linolenic acid in the fatty acids constituting the oil or fat is 15% or more, preferably 20% or more, more preferably 25% or more, even more preferably 30% or more, even more preferably 40% or more, even more preferably 50% or more, and even more preferably 52% or more. Furthermore, from the viewpoint of oxidation stability, the content is preferably 70% or less, more preferably 65% ​​or less, and even more preferably 60% or less. The content of α-linolenic acid in the fatty acids constituting the oil or fat of component (A) is 15% or more, preferably 15 to 70%, more preferably 20 to 70%, even more preferably 25 to 70%, even more preferably 30 to 65%, even more preferably 40 to 65%, even more preferably 50 to 65%, and even more preferably 52 to 60%. The amount of fatty acid in this specification is the amount converted to free fatty acid.

[0011] In the present invention, the constituent fatty acids other than α-linolenic acid that constitute the component (A) oil or fat are not particularly limited, and may be either saturated fatty acids or unsaturated fatty acids. From the viewpoints of flavor and industrial productivity of the oil, the content of unsaturated fatty acids in the fatty acids constituting the component (A) oil is preferably 60 to 100%, more preferably 70 to 100%, and even more preferably 80 to 99.5%. From the viewpoint of physiological effects, the number of carbon atoms in the unsaturated fatty acids is preferably 14 to 24, and more preferably 16 to 22.

[0012] In particular, the content of linoleic acid (C18:2) in the fatty acids constituting component (A) oil is preferably 5% or more, more preferably 10% or more, from the viewpoint of industrial productivity, and is preferably 40% or less, more preferably 30% or less, and even more preferably 20% or less. The content of linoleic acid in the fatty acids constituting the component (A) oil or fat is preferably 5 to 40%, more preferably 5 to 30%, and even more preferably 10 to 20%.

[0013] Furthermore, the content of oleic acid (C18:1) in the fatty acids constituting the component (A) oil or fat is preferably 10% or more, and preferably 65% ​​or less, more preferably 50% or less, and even more preferably 30% or less, from the viewpoint of industrial productivity. The content of oleic acid in the fatty acids constituting the component (A) oil or fat is preferably 10 to 65%, more preferably 10 to 50%, and even more preferably 10 to 30%.

[0014] The total content of saturated fatty acids in the fatty acids constituting component (A) oil is preferably 30% or less, more preferably 20% or less, even more preferably 10% or less, even more preferably 7% or less, and is preferably 0.5% or more, from the viewpoints of appearance, physiological effects, and industrial productivity of the oil. The saturated fatty acid preferably has 14 to 24 carbon atoms, and more preferably 16 to 22 carbon atoms.

[0015] In the present invention, the component (A) oil or fat contains 15% or more diacylglycerol. The higher the concentration of diacylglycerol in the component (A) oil or fat, the more likely it is that the component (B) vitamin C fatty acid ester will be contained, thereby enhancing oxidation stability. Therefore, from the viewpoint of effectively exerting the effect, it is preferable that the oil or fat contains a high content of diacylglycerol. The diacylglycerol content in the oil or fat component (A) is 15% or more, preferably 20% or more, more preferably 25% or more, even more preferably 30% or more, even more preferably 50% or more, even more preferably 60% or more, even more preferably 70% or more, and even more preferably 80% or more, from the viewpoint of the solubility, appearance, and physiological effects of the vitamin C fatty acid ester, and is preferably 99.5% or less, more preferably 98% or less, even more preferably 95% or less, and even more preferably 90% or less, from the viewpoint of industrial productivity. The diacylglycerol content in the component (A) oil or fat is 15% or more, preferably 15 to 99.5%, more preferably 20 to 98%, even more preferably 25 to 98%, even more preferably 30 to 95%, even more preferably 50 to 95%, even more preferably 60 to 90%, even more preferably 70 to 90%, and even more preferably 80 to 90%.

[0016] The oil or fat component (A) preferably contains triacylglycerol, and the content of triacylglycerol in the oil or fat component (A) is preferably 1% or more, more preferably 2% or more, even more preferably 5% or more, and even more preferably 10% or more, from the viewpoint of industrial productivity of the oil or fat, and is also preferably 85% or less, more preferably 80% or less, even more preferably 75% or less, even more preferably 72% or less, even more preferably 50% or less, and even more preferably 25% or less. The content of triacylglycerol in the component (A) oil or fat is preferably 1 to 85%, more preferably 2 to 80%, even more preferably 2 to 75%, even more preferably 5 to 50%, and even more preferably 10 to 25%.

[0017] The content of monoacylglycerol in the component (A) oil or fat is preferably 5% or less, more preferably 3% or less, even more preferably 2% or less, still more preferably 1.5% or less, and preferably more than 0%, from the viewpoints of flavor, industrial productivity of the oil or fat, and oxidation stability. The content of monoacylglycerol in the oil or fat may be 0%.

[0018] The content of free fatty acids or salts thereof in the oils and fats of component (A) is preferably 3% or less, more preferably 2% or less, even more preferably 1% or less, and is preferably more than 0% from the viewpoints of flavor and oxidation stability. The content of free fatty acids or salts thereof in the oils and fats may be 0%. The fatty acid composition of the triacylglycerol, diacylglycerol and monoacylglycerol may be the same or different.

[0019] Component (A) fats and oils can be obtained by an esterification reaction between fatty acids derived from fats and oils and glycerin, or by a transesterification reaction (glycerolysis) between fats and oils and glycerin. Esterification reactions and glycerolysis reactions are broadly classified into chemical methods using chemical catalysts such as alkali metals or their alloys, oxides or hydroxides of alkali metals or alkaline earth metals, and alkoxides of alkali metals or alkaline earth metals, and enzymatic methods using enzymes such as lipase. Among these, from the viewpoint of controlling the fatty acid composition, an esterification reaction between fractionated fatty acids derived from fats and oils, which will be described later, and glycerin is preferred.

[0020] In the present invention, the oils and fats (edible oils and fats) may be either vegetable oils and fats or animal oils and fats. Examples include vegetable oils and fats such as soybean oil, rapeseed oil, safflower oil, rice oil, corn oil, sunflower oil, cottonseed oil, olive oil, sesame oil, peanut oil, Job's tears oil, wheat germ oil, perilla oil, linseed oil, perilla oil, chia seed oil, sacha inchi oil, walnut oil, kiwi seed oil, salvia seed oil, grape seed oil, macadamia nut oil, hazelnut oil, pumpkin seed oil, camellia oil, tea seed oil, borage oil, palm oil, palm olein, palm stearin, coconut oil, palm kernel oil, cacao butter, sal fat, shea butter, and algae oil; animal oils and fats such as fish oil, lard, beef tallow, and butter fat; and interesterified oils, hydrogenated oils, and fractionated oils thereof. Among these, vegetable oils are preferred from the viewpoint of ease of use, and liquid oils with excellent low-temperature resistance are more preferred, and at least one oil selected from perilla oil, linseed oil, perilla oil, chia seed oil, and sacha inchi oil, which are rich in α-linolenic acid, is more preferred. Note that liquid oils refer to oils that are liquid at 20°C when subjected to a cooling test according to Standard Fats, Oils, and Related Materials Analysis Test Method 2.3.8-27.

[0021] Fatty acids derived from fats and oils can be obtained by hydrolyzing fats and oils. Methods for hydrolyzing fats and oils include high-temperature, high-pressure hydrolysis and enzymatic hydrolysis. High-temperature, high-pressure hydrolysis is a method in which water is added to fats and oils and the mixture is reacted under high temperature and high pressure conditions to obtain fatty acids and glycerin. Enzymatic hydrolysis is a method in which water is added to fats and oils and the mixture is reacted under low temperature conditions using an oil hydrolase as a catalyst to obtain fatty acids and glycerin. The hydrolysis reaction can be carried out according to a conventional method.

[0022] After the hydrolysis of fats and oils, it is preferable to remove solids by fractionating the hydrolysis reaction product. Fractionation methods include solvent fractionation, natural fractionation (dry fractionation), and wetting agent fractionation. The means for removing the precipitated solids include static separation, filtration, centrifugation, and a method of mixing the fatty acid with an aqueous solution of a wetting agent and separating the solids.

[0023] The esterification reaction between fatty acids derived from fats and oils and glycerin is preferably carried out under mild conditions by an enzymatic method, which is excellent in terms of flavor and the like. The amount of the enzyme used can be determined appropriately taking into consideration the activity of the enzyme. When an immobilized enzyme is used, the amount is preferably 1 to 30%, more preferably 2 to 20%, of the total mass of the esterification reaction raw materials in order to improve the reaction rate. The reaction temperature for the esterification reaction is preferably 0 to 100° C., more preferably 20 to 80° C., and even more preferably 30 to 60° C., from the viewpoint of increasing the reaction rate and suppressing the deactivation of the enzyme. The reaction time is preferably within 15 hours, more preferably 1 to 12 hours, and even more preferably 2 to 10 hours, from the viewpoint of industrial productivity. The fatty acids and glycerin can be brought into contact with each other by immersion, stirring, or by passing the mixture through a column packed with immobilized lipase using a pump or the like.

[0024] After the esterification reaction, the product may be subjected to a refining process that is usually used for fats and oils, such as distillation, acid treatment, water washing, bleaching, and deodorization.

[0025] The content of the oil or fat component (A) in the oil-in-water emulsion composition is preferably 5% or more, more preferably 8% or more, even more preferably 10% or more, even more preferably 15% or more, even more preferably 20% or more, and even more preferably 30% or more, from the viewpoints of emulsion stability, oxidation stability, flavor, and industrial productivity, and is preferably 80% or less, more preferably 75% or less, even more preferably 70% or less, even more preferably 60% or less, even more preferably 50% or less, and even more preferably 45% or less. The content of the component (A) oil or fat in the oil-in-water emulsion composition is preferably 5 to 80%, more preferably 8 to 75%, even more preferably 10 to 70%, even more preferably 15 to 60%, even more preferably 20 to 50%, and even more preferably 30 to 45%.

[0026] The oil-in-water emulsion composition of the present invention contains (B) a vitamin C fatty acid ester. Hereinafter, in this specification, the "vitamin C fatty acid ester" will also be referred to as "component (B)." The vitamin C fatty acid ester used in the present invention is an ester of L-ascorbic acid and a higher fatty acid, and commercially available products, preferably those for food and beverage use, can be used. As the higher fatty acid, a linear saturated fatty acid having 12 to 22 carbon atoms is preferred. One or more types of vitamin C fatty acid esters may be used in combination. The vitamin C fatty acid ester is preferably vitamin C palmitate, vitamin C stearate, or a combination thereof, more preferably vitamin C palmitate, because it has high oxidation stability, little fishy or fishy odor, and a good flavor.

[0027] In the present invention, the content of component (B) in the oil-in-water emulsion composition is 0.020 to 1.0% relative to component (A). From the viewpoint of oxidative stability, the content of component (B) in the oil-in-water emulsion composition is 0.020% or more, preferably 0.025% or more, more preferably 0.03% or more, even more preferably 0.05% or more, and even more preferably 0.1% or more relative to component (A). From the viewpoint of solubility and appearance of the vitamin C fatty acid ester, the content of component (B) in the oil-in-water emulsion composition is 1.0% or less, preferably 0.5% or less, more preferably 0.3% or less, and even more preferably 0.2% or less. The content of component (B) in the oil-in-water emulsion composition is 0.020 to 1.0%, preferably 0.025 to 1.0%, more preferably 0.03 to 0.5%, even more preferably 0.05 to 0.5%, even more preferably 0.1 to 0.5%, even more preferably 0.1 to 0.3%, and even more preferably 0.1 to 0.2%, relative to component (A).

[0028] The oil-in-water emulsion composition of the present invention contains (C) a hydroxy acid or a salt thereof. Hereinafter, in this specification, "hydroxy acid or a salt thereof" may also be referred to as "component (C)." The hydroxy acid used in the present invention is a general term for compounds having a carboxy group and an alcoholic hydroxyl group in one molecule, and examples thereof include lactic acid, tartaric acid, malic acid, and citric acid. As the salt of a hydroxy acid, an alkali metal salt is preferred, with sodium salt and potassium salt being more preferred, with sodium salt being even more preferred. These may be used alone or in combination of two or more. The hydroxy acid or its salt may be either an anhydride or a hydrate. Among these, from the viewpoints of oxidation stability and flavor, the hydroxy acid or its salt is preferably one or more selected from citric acid, tartaric acid, malic acid, and salts thereof, more preferably citric acid or sodium citrate, and even more preferably sodium citrate.

[0029] In the present invention, the content of component (C) in the oil-in-water emulsion composition is 0.15 to 6.0%. From the viewpoints of oxidative stability and flavor, the content of component (C) in the oil-in-water emulsion composition is 0.15% or more, preferably 0.20% or more, more preferably 0.30% or more, even more preferably 0.50% or more, and even more preferably 0.60% or more, and from the viewpoints of oxidative stability and flavor, the content of component (C) in the oil-in-water emulsion composition is 6.0% or less, preferably 4.0% or less, even more preferably 3.0% or less, even more preferably 2.0% or less, and even more preferably 1.0% or less. The content of component (C) in the oil-in-water emulsion composition is 0.15 to 6.0%, preferably 0.20 to 4.0%, more preferably 0.30 to 3.0%, even more preferably 0.50 to 2.0%, and still more preferably 0.60 to 1.0%. In this specification, when component (C) is a salt or a hydrate, the content of component (C) is expressed as a value converted into the hydroxy acid, which is a free acid.

[0030] The oil-in-water emulsion composition of the present invention preferably further contains an emulsifier (D) in terms of emulsion stability, appearance, and industrial productivity. Hereinafter, in this specification, the "emulsifier" may also be referred to as "component (D)." Examples of emulsifiers used in the present invention include processed starch; synthetic emulsifiers such as organic acid monoglycerides, polyglycerol fatty acid esters, propylene glycol fatty acid esters, polyglycerol condensed ricinoleate esters, sorbitan fatty acid esters, sorbitol fatty acid esters, and sucrose fatty acid esters; and natural emulsifiers such as saponin, lecithin or its enzymatic hydrolysates, milk proteins (such as buttermilk powder and sodium caseinate), soybean proteins, and wheat proteins, as well as isolates and hydrolysates of these proteins. These emulsifiers may be used alone or in combination of two or more. Among these, from the viewpoints of emulsion stability, flavor, and oxidative stability, preferred are one or more selected from processed starch, sucrose fatty acid esters, polyglycerol fatty acid esters, lecithin or its enzymatic hydrolysates, and milk proteins, more preferred are one or more selected from processed starch, polyglycerol fatty acid esters, and milk proteins, and even more preferred are one or more selected from milk proteins. Examples of processed starches include starches that have been subjected to processes such as etherification (e.g., hydroxypropyl starch, carboxymethyl starch, etc.); esterification (e.g., acetylated starch, octenyl succinate starch, phosphate starch, etc.); crosslinking (e.g., phosphate crosslinked starch, adipic acid crosslinked starch, etc.); and oxidation (e.g., oxidized starch treated with an oxidizing agent such as sodium hypochlorite, etc.), or a combination of these processes.

[0031] The content of component (D) in the oil-in-water emulsion composition is preferably 0.05% or more, more preferably 0.2% or more, even more preferably 0.5% or more, and even more preferably 1% or more, from the viewpoints of emulsion stability, flavor, and oxidation stability, and is preferably 30% or less, more preferably 10% or less, and even more preferably 5% or less. The content of component (D) in the oil-in-water emulsion composition is preferably 0.05 to 30%, more preferably 0.2 to 10%, even more preferably 0.5 to 10%, and still more preferably 1 to 5%.

[0032] In the present invention, the mass ratio of the content of component (B) relative to component (A) to the content of α-linolenic acid in the fatty acids constituting the component (A) oil, [(ALA) / (component (B))], is preferably 30 or more, more preferably 40 or more, even more preferably 50 or more, even more preferably 100 or more, even more preferably 150 or more, and even more preferably 200 or more, from the viewpoints of flavor, solubility of vitamin C fatty acid ester, physiological function, and oxidative stability; and is preferably 3000 or less, more preferably 2500 or less, even more preferably 2000 or less, even more preferably 1500 or less, even more preferably 1000 or less, and even more preferably 800 or less, from the viewpoints of flavor and oxidative stability. In the present invention, the mass ratio of the content of component (B) relative to component (A) to the content of α-linolenic acid in the fatty acids constituting the component (A) oil / fat [(ALA) / (component (B))] is preferably 30 to 3,000, more preferably 40 to 2,500, even more preferably 50 to 2,000, even more preferably 100 to 1,500, even more preferably 150 to 1,000, and even more preferably 200 to 800, from the viewpoints of flavor, solubility of vitamin C fatty acid ester, physiological function, and oxidative stability.

[0033] In the present invention, the mass ratio of the content of component (B) relative to component (A) to the content of component (C) in the oil-in-water emulsion composition [(component (C)) / (component (B))] is preferably 0.20 or more, more preferably 0.30 or more, even more preferably 0.50 or more, even more preferably 2.0 or more, even more preferably 3.0 or more, and even more preferably 5.0 or more, from the viewpoints of flavor and oxidative stability; and is preferably 200 or less, more preferably 100 or less, even more preferably 50 or less, even more preferably 40 or less, even more preferably 30 or less, and even more preferably 20 or less, from the viewpoints of flavor and oxidative stability. In the present invention, the mass ratio of the content of component (B) relative to component (A) to the content of component (C) in the oil-in-water emulsion composition [(component (C)) / (component (B))] is preferably 0.20 to 200, more preferably 0.30 to 100, even more preferably 0.50 to 50, even more preferably 0.50 to 40, even more preferably 0.50 to 30, even more preferably 2.0 to 30, even more preferably 3.0 to 30, and even more preferably 5.0 to 20, from the viewpoints of flavor and oxidative stability.

[0034] The oil phase of the oil-in-water emulsion composition may contain an antioxidant other than component (B) or other oil-soluble components from the viewpoint of the oxidation stability of component (A) oil. The content of the oil-soluble components can be appropriately set within a range that does not impair the object of the present invention.

[0035] The aqueous phase of the oil-in-water emulsion composition is not particularly limited, and may contain water; excipients such as monosaccharides, disaccharides, starch hydrolysates, and sugar alcohols; hydrophilic antioxidants; and water-soluble components such as thickeners, preservatives, colorants, sweeteners, seasonings, and fragrances. In the present invention, these can be appropriately blended depending on the viscosity, physical properties, and the like of the target composition. The pH of the aqueous phase is preferably 1 to 12, more preferably 2 to 11, and even more preferably 5 to 10, from the viewpoints of oxidation stability, emulsion stability, and flavor.

[0036] The blending ratio (mass ratio) of the oil phase to the water phase in the oil-in-water emulsion composition is preferably 5 / 95 to 80 / 20, more preferably 8 / 92 to 75 / 25, even more preferably 10 / 90 to 70 / 30, even more preferably 15 / 85 to 60 / 40, even more preferably 20 / 80 to 50 / 50, and even more preferably 30 / 70 to 45 / 55.

[0037] The oil-in-water emulsion composition of the present invention can be produced by mixing component (A), component (B), component (C), and, if necessary, component (D) according to a conventional method. Preferably, component (A) and component (B) are first mixed to prepare an oil phase. On the other hand, water and component (C), and, if necessary, component (D), are mixed to prepare an aqueous phase. Next, the oil phase is added to the aqueous phase, and if necessary, preliminary emulsification is carried out, followed by homogenization, to obtain an oil-in-water emulsion composition. Examples of the homogenizer include a high-pressure homogenizer, an ultrasonic emulsifier, a colloid mill, an Ajihomomixer, and a milder.

[0038] The oil-in-water emulsion composition thus produced may be used as is, or may be dried and used as a powdered oil. The oil-in-water emulsion composition of the present invention has high oxidation stability despite its high content of α-linolenic acid and little fishy or fishy odor, and therefore can provide a powdered oil rich in α-linolenic acid and with a good flavor. As the drying method, a common method can be used, such as spray drying, freeze drying, vacuum drying, belt drying, shelf drying, drum drying, etc. If necessary, classification, granulation, pulverization, etc. may be performed to obtain particles of a desired particle size. Among these, spray drying is preferred from the viewpoints of productivity, thermal history, and particle shape.

[0039] The oil-in-water emulsion composition and powdered oil of the present invention can be used in the same way as general edible oils and fats, and can be applied to various foods, beverages, and feeds that use oils and fats. Examples of foods and beverages that use oils and fats include, in addition to ordinary foods and beverages, foods for specified health uses that claim to utilize the physiological effects of α-linolenic acid or diacylglycerol, and foods with functional claims. The form of the food or drink may be solid, semi-solid, or liquid, and examples thereof include beverages, water-in-oil type oil-containing foods, oil-in-water type oil-containing foods, bakery foods, confectionery, frozen foods, retort foods, and nutritional supplement compositions such as tablets, capsules, and lozenges. Examples of feed include livestock feed for cows, pigs, etc., small animal feed for rabbits, mice, etc., seafood feed for eels, shrimp, etc., and pet food for dogs, cats, etc.

[0040] The oil-in-water emulsion composition of the present invention contains the following components (A), (B) and (C) in order to have high oxidation stability, a good flavor with little fishy or raw odor, and physiological effects: (A) Oils and fats having a diacylglycerol content of 20 to 98% by mass and an α-linolenic acid content of 20 to 70% by mass among fatty acids constituting the oils and fats (B) Vitamin C fatty acid ester: 0.025 to 1.0% by mass of component (A) (C) Hydroxy acid or its salt 0.20 to 6.0 mass% It is preferable that the composition is an oil-in-water emulsion composition containing:

[0041] The oil-in-water emulsion composition of the present invention comprises the following components (A), (B), (C) and (D) in order to have high oxidation stability, a good flavor with little fishy or raw odor, and physiological effects: (A) Oils and fats having a diacylglycerol content of 20 to 98% by mass and an α-linolenic acid content of 20 to 70% by mass among fatty acids constituting the oils and fats (B) Vitamin C fatty acid ester: 0.025 to 1.0% by mass of component (A) (C) Hydroxy acid or its salt 0.20 to 6.0 mass% (D) Emulsifier 0.05 to 30% by mass It is preferable that the composition is an oil-in-water emulsion composition containing:

[0042] The oil-in-water emulsion composition of the present invention comprises the following components (A), (B), (C) and (D) in order to have high oxidation stability, a good flavor with little fishy or raw odor, and physiological effects: (A) Oils and fats having a diacylglycerol content of 20 to 95% by mass and an α-linolenic acid content of 20 to 70% by mass among fatty acids constituting the oils and fats (B) Vitamin C fatty acid ester 0.025 to 0.5% by mass of component (A) (C) Hydroxy acid or its salt 0.20 to 6.0 mass% (D) Emulsifier 0.2 to 30% by mass It is preferable that the composition is an oil-in-water emulsion composition containing:

[0043] The oil-in-water emulsion composition of the present invention comprises the following components (A), (B), (C) and (D) in order to have high oxidation stability, a good flavor with little fishy or raw odor, and physiological effects: (A) Oils and fats having a diacylglycerol content of 30 to 90% by mass and an α-linolenic acid content of 25 to 70% by mass among the fatty acids constituting the oils and fats (B) Vitamin C fatty acid ester: 0.05 to 0.5% by mass of component (A) (C) Hydroxy acid or its salt 0.20 to 3.0% by mass (D) Emulsifier 0.2 to 10% by mass It is preferable that the composition is an oil-in-water emulsion composition containing:

[0044] In relation to the above-mentioned embodiments, the present invention further discloses the following oil-in-water emulsion composition and powdered oil.

[0045] <1> The following components (A), (B), and (C): (A) Oils and fats having a diacylglycerol content of 15% by mass or more and an α-linolenic acid content of 15% by mass or more among the fatty acids constituting the oils and fats (B) Vitamin C fatty acid ester: 0.020 to 1.0% by mass of component (A) (C) Hydroxy acid or its salt 0.15 to 6.0% by mass An oil-in-water emulsion composition comprising:

[0046] <2> The content of α-linolenic acid in the fatty acids constituting the oil or fat of component (A) is 15% by mass or more, preferably 20% by mass or more, more preferably 25% by mass or more, even more preferably 30% by mass or more, even more preferably 40% by mass or more, even more preferably 50% by mass or more, and even more preferably 52% by mass or more, and is preferably 70% by mass or less, more preferably 65% ​​by mass or less, and even more preferably 60% by mass or less, and is preferably 15 to 70% by mass, more preferably 20 to 70% by mass, even more preferably 25 to 70% by mass, even more preferably 30 to 65% by mass, even more preferably 40 to 65% by mass, even more preferably 50 to 65% by mass, and even more preferably 52 to 60% by mass. <1> The oil-in-water emulsion composition according to claim 1. <3> The content of linoleic acid in the fatty acids constituting the oil or fat of component (A) is preferably 5% by mass or more, more preferably 10% by mass or more, and is preferably 40% by mass or less, more preferably 30% by mass or less, even more preferably 20% by mass or less, and is preferably 5 to 40% by mass, more preferably 5 to 30% by mass, even more preferably 10 to 20% by mass. <1> or <2> The oil-in-water emulsion composition according to claim 1. <4> The content of oleic acid in the fatty acids constituting the oil or fat of component (A) is preferably 10% by mass or more, and is preferably 65% ​​by mass or less, more preferably 50% by mass or less, and even more preferably 30% by mass or less, and is preferably 10 to 65% by mass, more preferably 10 to 50% by mass, and even more preferably 10 to 30% by mass. <1> ~ <3> 1. The oil-in-water emulsion composition according to any one of claims 1 to 9. <5> The content of diacylglycerol in the component (A) oil or fat is 15% by mass or more, preferably 20% by mass or more, more preferably 25% by mass or more, even more preferably 30% by mass or more, even more preferably 50% by mass or more, even more preferably 60% by mass or more, even more preferably 70% by mass or more, and even more preferably 80% by mass or more, and is preferably 99.5% by mass or less, more preferably 98% by mass or less, even more preferably 95% by mass or less, and even more preferably 90% by mass or less, and is preferably 15 to 99.5% by mass, more preferably 20 to 98% by mass, even more preferably 25 to 98% by mass, even more preferably 30 to 95% by mass, even more preferably 50 to 95% by mass, even more preferably 60 to 90% by mass, even more preferably 70 to 90% by mass, and even more preferably 80 to 90% by mass. <1> ~ <4> 1. The oil-in-water emulsion composition according to any one of claims 1 to 9. <6> The content of triacylglycerol in the component (A) oil or fat is preferably 1% by mass or more, more preferably 2% by mass or more, even more preferably 5% by mass or more, and even more preferably 10% by mass or more, and is preferably 85% by mass or less, more preferably 80% by mass or less, even more preferably 75% by mass or less, even more preferably 50% by mass or less, and even more preferably 25% by mass or less, and is preferably 1 to 85% by mass, more preferably 2 to 80% by mass, even more preferably 2 to 75% by mass, even more preferably 5 to 50% by mass, and even more preferably 10 to 25% by mass. <1> ~ <5> 1. The oil-in-water emulsion composition according to any one of claims 1 to 9. <7> The content of monoacylglycerol in the component (A) oil or fat is preferably 5% by mass or less, more preferably 3% by mass or less, even more preferably 2% by mass or less, even more preferably 1.5% by mass or less, and preferably more than 0% by mass. <1> ~ <6> 1. The oil-in-water emulsion composition according to any one of claims 1 to 9. <8> The content of free fatty acids or salts thereof in the component (A) oil or fat is preferably 3% by mass or less, more preferably 2% by mass or less, even more preferably 1% by mass or less, and preferably more than 0% by mass. <1> ~ <7> 1. The oil-in-water emulsion composition according to any one of claims 1 to 9. <9> The component (A) oil or fat preferably contains an esterified oil of fractionated fatty acids derived from oil or fat and glycerin. <1> ~ <8> 1. The oil-in-water emulsion composition according to any one of claims 1 to 9. <10> The fractionated fatty acids are preferably derived from at least one oil selected from perilla oil, linseed oil, perilla oil, chia seed oil, and sacha inchi oil. <9> The oil-in-water emulsion composition according to claim 1. <11> The content of the oil or fat component (A) in the oil-in-water emulsion composition is preferably 5% by mass or more, more preferably 8% by mass or more, even more preferably 10% by mass or more, even more preferably 15% by mass or more, even more preferably 20% by mass or more, and even more preferably 30% by mass or more, and is preferably 80% by mass or less, more preferably 75% by mass or less, even more preferably 70% by mass or less, even more preferably 60% by mass or less, even more preferably 50% by mass or less, and even more preferably 45% by mass or less, and is preferably 5 to 80% by mass, more preferably 8 to 75% by mass, even more preferably 10 to 70% by mass, even more preferably 15 to 60% by mass, even more preferably 20 to 50% by mass, and even more preferably 30 to 45% by mass. <1> ~ <10> 1. The oil-in-water emulsion composition according to any one of claims 1 to 9. <12> Component (B) is preferably vitamin C palmitate, vitamin C stearate, or a combination thereof, more preferably vitamin C palmitate. <1> ~ <11> 1. The oil-in-water emulsion composition according to any one of claims 1 to 9. <13> The content of component (B) in the oil-in-water emulsion composition relative to component (A) is 0.020% by mass or more, preferably 0.025% by mass or more, more preferably 0.03% by mass or more, even more preferably 0.05% by mass or more, and still more preferably 0.1% by mass or more, and is 1.0% by mass or less, preferably 0.5% by mass or less, more preferably 0.3% by mass or less, and still more preferably 0.2% by mass or less, and is 0.020 to 1.0% by mass, preferably 0.025 to 1.0% by mass, more preferably 0.03 to 0.5% by mass, even more preferably 0.05 to 0.5% by mass, even more preferably 0.1 to 0.5% by mass, even more preferably 0.1 to 0.3% by mass, and still more preferably 0.1 to 0.2% by mass. <1> ~ <12> 1. The oil-in-water emulsion composition according to any one of claims 1 to 9. <14> (C) The hydroxy acid or its salt is preferably at least one selected from citric acid, tartaric acid, malic acid, and salts thereof, more preferably citric acid, sodium citrate, or a combination thereof, and even more preferably sodium citrate. <1> ~ <13> 1. The oil-in-water emulsion composition according to any one of claims 1 to 9. <15> The content of component (C) in the oil-in-water emulsion composition is 0.15% by mass or more, preferably 0.20% by mass or more, more preferably 0.30% by mass or more, even more preferably 0.50% by mass or more, still more preferably 0.60% by mass or more, and is 6.0% by mass or less, preferably 4.0% by mass or less, even more preferably 3.0% by mass or less, even more preferably 2.0% by mass or less, still more preferably 1.0% by mass or less, and is 0.15 to 6.0% by mass, preferably 0.20 to 4.0% by mass, more preferably 0.30 to 3.0% by mass, even more preferably 0.50 to 2.0% by mass, and still more preferably 0.60 to 1.0% by mass. <1> ~ <14> 1. The oil-in-water emulsion composition according to any one of claims 1 to 9. <16> Preferably, it further contains (D) an emulsifier. <1> ~ <15> 1. The oil-in-water emulsion composition according to any one of claims 1 to 9. <17> The (D) emulsifier is preferably one or more selected from modified starch, sucrose fatty acid ester, polyglycerol fatty acid ester, lecithin or its enzymatic hydrolyzate, and milk protein, more preferably one or more selected from modified starch, polyglycerol fatty acid ester, and milk protein, and even more preferably one or more selected from milk protein. <16> The oil-in-water emulsion composition according to claim 1. <18> The content of component (D) in the oil-in-water emulsion composition is preferably 0.05% by mass or more, more preferably 0.2% by mass or more, even more preferably 0.5% by mass or more, and even more preferably 1% by mass or more, and is preferably 30% by mass or less, more preferably 10% by mass or less, and even more preferably 5% by mass or less, and is preferably 0.05 to 30% by mass, more preferably 0.2 to 10% by mass, even more preferably 0.5 to 10% by mass, and even more preferably 1 to 5% by mass. <16> or <17> The oil-in-water emulsion composition according to claim 1. <19> The mass ratio of the content of component (B) relative to the content of component (A) to the content of α-linolenic acid in the fatty acids constituting the component (A) oil and fat [(ALA) / (component (B))] is preferably 3. 0 or more, more preferably 40 or more, more preferably 50 or more, more preferably 100 or more, more preferably 150 or more, and more preferably 200 or more; and preferably 3000 or less, more preferably 2500 or less, more preferably 2000 or less, more preferably 1500 or less, more preferably 1000 or less, and more preferably 800 or less; and preferably 30 to 3000, more preferably 40 to 2500, more preferably 50 to 2000, more preferably 100 to 1500, more preferably 150 to 1000, and more preferably 200 to 800. <1> ~ <18> 1. The oil-in-water emulsion composition according to any one of claims 1 to 9. <20> The mass ratio of the content of component (B) relative to component (A) to the content of component (C) in the oil-in-water emulsion composition [(component (C)) / (component (B))] is preferably 0.20 or more, more preferably 0.30 or more, even more preferably 0.50 or more, even more preferably 2.0 or more, even more preferably 3.0 or more, and even more preferably 5.0 or more, and is preferably 200 or less, more preferably 100 or less, even more preferably 50 or less, even more preferably 40 or less, even more preferably 30 or less, and even more preferably 20 or less, and is preferably 0.20 to 200, more preferably 0.30 to 100, even more preferably 0.50 to 50, even more preferably 0.50 to 40, even more preferably 0.50 to 30, even more preferably 2.0 to 30, even more preferably 2.0 to 30, even more preferably 3.0 to 30, and even more preferably 5.0 to 20. <1> ~ <19> 1. The oil-in-water emulsion composition according to any one of claims 1 to 9. <21> The blending ratio (mass ratio) of the oil phase to the water phase is preferably 5 / 95 to 80 / 20, more preferably 8 / 92 to 75 / 25, even more preferably 10 / 90 to 70 / 30, even more preferably 15 / 85 to 60 / 40, even more preferably 20 / 80 to 50 / 50, and even more preferably 30 / 70 to 45 / 55. <1> ~ <20> 1. The oil-in-water emulsion composition according to any one of claims 1 to 9. A powdery oil and fat obtained by drying the water-in-oil type emulsified composition according to any one of <22><1> to <21>. <23>A food or drink containing the water-in-oil type emulsified composition according to any one of <22><1> to <21> or the powdery oil and fat according to <22>. <24>A feed containing the water-in-oil type emulsified composition according to any one of <22><1> to <21> or the powdery oil and fat according to <22>.

Examples

[0047] 〔Analysis method〕 (i) Glyceride composition of oil and fat Approximately 10 mg of an oil and fat sample and 0.5 mL of a trimethylsilylating agent (“Silylating agent TH”, manufactured by Kanto Chemical Co., Inc.) were added to a glass sample bottle, sealed, and heated at 70 °C for 15 minutes. 1.0 mL of water and 1.5 mL of hexane were added thereto and shaken. After standing, the upper layer was subjected to gas chromatography (GLC) for analysis. <GLC analysis conditions> (Condition) Apparatus: Agilent 7890B (manufactured by Agilent Technologies) Column: DB-1ht 10 m × 0.25 mm × 0.2 μm (manufactured by Agilent J&W) Carrier gas: 1.0 mL He / min Injector: Split (1:50), T = 340 °C Detector: FID, T = 350 °C Oven temperature: Temperature was raised from 80 °C to 340 °C at 10 °C / min and held for 15 minutes.

[0048] (ii) Constituent fatty acid composition of oil and fat Fatty acid methyl esters were prepared according to “Method for Preparation of Fatty Acid Methyl Esters (2.4.1.-1996)” in “Standard Oil and Fat Analysis Test Methods” edited by the Japanese Oil Chemists' Society, and the obtained oil and fat sample was measured in accordance with American Oil Chemists. Society Official Method Ce 1f-96 (GLC method). <GLC analysis conditions> Apparatus: Agilent 7890B (manufactured by Agilent Technologies) Column: CP-SIL88 50 m x 0.25 mm x 0.2 μm (Agilent J&W) Carrier gas: 1.0 mL He / min Injector: Split (1:50), T=300℃ Detector: FID, T=300℃ Oven temperature: 150°C, 5 min hold → 1°C / min temperature increase → 160°C, 5 min hold → 2°C / min temperature increase → 200°C, 10 min hold → 10°C / min temperature increase → 220°C, 5 min hold

[0049] (iii) Peroxide Value (POV) Measurement 5 mL of ion-exchanged water was added to approximately 2.5 g of the oil-in-water emulsion composition and stirred, followed by addition of 10 mL of THF, stirring, and centrifugation (3000 r / min, 10 minutes, 20°C). Next, 20 mL of hexane and 10 mL of ion-exchanged water were added, followed by centrifugation (3000 r / min, 5 minutes, 20°C). The upper layer was then removed and the solvent was removed using a rotary evaporator to prepare an oil. The POV of the extracted oils and fats was measured based on the Standard Method for Analysis of Fats and Oils (JOCS) 2.5.2.2-2013.

[0050] [Raw materials] The following oils a to d were prepared. Oil a: Semi-refined linseed oil (ADM) was enzymatically hydrolyzed to obtain fatty acids, and the saturated fatty acid content was reduced by winterization. The fractionated fatty acids and glycerin were then esterified under reduced pressure using a commercially available immobilized 1,3-position-selective lipase as a catalyst. After filtering off the immobilized enzyme, the reaction product was subjected to molecular distillation, washed with water, deodorized, and 0.2% by mass of a tocopherol preparation (Riken Vitamin Co., Ltd.) was added to obtain oil a. Oil b: High oleic safflower oil (manufactured by J-Oil Mills) Oil c: Oil a and oil b were mixed in a mass ratio of 1:1 to prepare oil c. Oil d: Oil a and oil b were mixed in a mass ratio of 1:4 to prepare oil d. Table 1 shows the glyceride compositions and fatty acid compositions of fats and oils a to d.

[0051] [Table 1]

[0052] Vitamin C palmitate (VCP): L-ascorbic acid palmitate (manufactured by DSM) Vitamin C stearate (VCS): 6-O-Stearoyl-L-ascorbic Acid (Tokyo Chemical Industry Co., Ltd.) Sodium citrate: Purified sodium citrate (Fuso Chemical Co., Ltd., uses trisodium citrate dihydrate as the substance) Sodium tartrate: Sodium L-tartrate (Fuso Chemical Co., Ltd.) Sodium malate: DL-sodium malate (Fuso Chemical Co., Ltd.) Citric acid: Purified citric acid (manufactured by Fuso Chemical Industry Co., Ltd.) Modified starch: Emulstar 500A (Matsutani Chemical Industry) Sodium caseinate: Sodium caseinate AR (manufactured by San-ei Gen F.F.I.) Polyglycerin fatty acid ester: Sunsoft Q17s (Taiyo Chemical) Lysolecithin: SLP-White (Tsuji Oil Mills) Buttermilk powder: Hokkaido buttermilk powder (Yotsuba Dairy) Rosemary extract: StabilEnhance OSR D4 (Naturex) Hydrophilic antioxidant: Xtrablend RN (Naturex) Dextrin: Sandec #100 (manufactured by Sanwa Starch Industry Co., Ltd.)

[0053] Comparative Examples 1 to 6 [Preparation of oil-in-water emulsion composition] The oil and fat and VCP were placed in a four-neck flask in the proportions shown in Table 2, and dissolved under a nitrogen atmosphere at 95°C for 30 minutes with stirring (300-350 r / min) to prepare an oil phase. After allowing to cool, it was confirmed that the oil phase did not become cloudy even after being left at room temperature for 1 hour. Component (C) and (D) shown in Table 2 were added to ion-exchanged water and stirred at 10,000 r / min for 2 minutes to prepare an aqueous phase. The above oil phase was added to the aqueous phase and stirred at 10,000 r / min for 8 minutes to prepare oil-in-water type emulsion compositions respectively.

[0054] 〔Evaluation〕 The oil-in-water type emulsion compositions prepared above were evaluated by the following three methods. (1) Sensory evaluation 10 g of the oil-in-water type emulsion composition was placed in a 20 mL vial with a lid and stored at room temperature for 24 hours. Then, three professional panelists evaluated it according to the judgment criteria shown below. For "fishy odor" and "raw smell", the score of Comparative Example 1 was set as 5 (felt very strongly), and for other examples, the score was determined by the agreement of the three. 5: Feel fishy odor and raw smell very strongly 4: Feel fishy odor and raw smell strongly 3: Feel fishy odor and raw smell, there is a problem 2: Feel fishy odor and raw smell very slightly, no problem 1: Hardly feel fishy odor and raw smell

[0055] (2) 1-Penten-3-one peak area relative area ratio Analysis of 1-penten-3-one, which is one of the typical fishy odor components, was carried out to evaluate the inhibitory effect on fishy odor and raw smell. The analysis of 1-penten-3-one was performed by headspace solid-phase microextraction / gas chromatography-mass spectrometry (HS-SPME / GC / MS) method. The SPME fiber used was 50 / 30μm, DVB / CAR / PDMS fiber (manufactured by SUPELCO). 10 g of the oil-in-water type emulsion composition was placed in a 20 mL vial with a lid and stored at room temperature for 24 hours. Then, 1 g of the sample was weighed into a headspace vial (10 mL), heated at 40°C for 20 minutes, and the headspace phase was sampled by the SPME fiber for 30 minutes. Then, the analysis was carried out under the following conditions. <GC / MS analysis conditions> Apparatus: Agilent 7890A / 5975 (manufactured by Agilent Technologies) Column: VF-WAX 60 m x 0.25 mm x 1.0 μm (Agilent J&W) Carrier gas: 1.0 mL He / min Injector: Splitless, 240℃ Oven temperature: 35°C, held for 4 minutes → 3°C / min temperature increase → 185°C → 10°C / min temperature increase → 240°C, held for 10 minutes The volatile components in the gas phase were analyzed by HS-GC / MS using SPME, and the peak area of ​​1-penten-3-one, one of the components that causes the fishy odor, was calculated by integration. The relative ratios of the peak area of ​​Comparative Examples 2 to 6 were calculated, assuming that the peak area of ​​Comparative Example 1 was 1.00.

[0056] (3) Oxidation stability The oxidative stability of the oil-in-water emulsion composition was evaluated for those that received a score of 1 (almost not noticeable) or 2 (slightly noticeable, but not a problem) in the sensory evaluation. In the evaluation of oxidative stability, 10 g of the oil-in-water emulsion composition was placed in a 20 mL vial with a cap and stored at 60°C for 3 days, after which the oil in the oil-in-water emulsion composition was extracted and the POV was measured. The results are shown in Table 2.

[0057] [Table 2]

[0058] As shown in Table 2, Comparative Examples 1, 2, and 6, which contained 0.1% VCP and oil / fat a or oil / fat c, had a strong fishy odor. Comparative Examples 3 and 5, which contained no VCP, and Comparative Example 4, which contained 0.015% VCP, had little fishy odor and a fishy odor that was at an acceptable level, but had low oxidation stability.

[0059] Examples 1 to 23 [Preparation of oil-in-water emulsion composition] The oil and fat and VCP or VCS were placed in a four-neck flask in the proportions shown in Table 3, and dissolved under a nitrogen atmosphere at 95°C with stirring (300-350 r / min) for 30 minutes to prepare an oil phase. After allowing to cool, it was confirmed that the oil did not become cloudy even after being left at room temperature for 1 hour. Components (C) and (D) shown in Table 3 were added to ion-exchanged water and stirred at 10,000 r / min for 2 minutes to prepare an aqueous phase. The oil phase was added to the aqueous phase and stirred at 10,000 r / min for 8 minutes to prepare oil-in-water emulsion compositions.

[0060] 〔evaluation〕 The oil-in-water emulsion compositions prepared above were evaluated by the following three methods. (1) Sensory evaluation As with the evaluation of Comparative Examples 2 to 6, the "fishy smell" and "fishy smell" of Comparative Example 1 were evaluated as being 5 (very strong).

[0061] (2) 1-Penten-3-one Peak Area Relative Area Ratio The peak area of ​​Comparative Example 1 was set to 1.00, and the relative area ratio was determined in the same manner as in Comparative Examples 2 to 6.

[0062] (3) Oxidation stability In the same manner as in Comparative Examples 3 to 5, the oil-in-water emulsion compositions were stored at 60°C for 3 days, and then the POV was measured. The results are shown in Table 3.

[0063] [Table 3-1]

[0064] [Table 3-2]

[0065] As shown in Tables 3-1 and 3-2, Examples 1 to 23 were rated 1 (almost not noticeable) or 2 (slightly noticeable, but not problematic), and the fishy odor and fishy smell were minimal and not problematic. It was also confirmed that the relative area ratio of the peak area of ​​1-penten-3-one compared to Comparative Example 1 was small. In addition, the oxidation stability was also better than that of Comparative Examples 3 to 5.

[0066] Examples 24 to 25 and Comparative Example 7 [Preparation of oil-in-water emulsion composition] VCP and rosemary extract were heated and mixed with oil / fat a under reduced pressure in the proportions shown in Table 4 to prepare an oil phase. The components (C), (D), hydrophilic antioxidant, and dextrin shown in Table 4 were added to ion-exchanged water while stirring at 1,400 r / min, and the mixture was stirred at 4,000 r / min for 26 minutes to prepare an aqueous phase. The oil phase was then added to the aqueous phase, and the mixture was stirred at 8,000 r / min for 15 minutes to obtain an oil-in-water emulsion composition.

[0067] [Preparation of powdered oils and fats] The oil-in-water emulsion composition obtained above was spray-dried using a spray dryer (TRS-5W2N manufactured by Sakamoto Giken Co., Ltd.) under conditions of an air temperature of 150°C, a spray flow rate of 90 g / min, a two-fluid nozzle, and a spray air flow rate of 150 to 160 L / min, to obtain a powdered oil.

[0068] 〔evaluation〕 The powdered oils and fats prepared above were evaluated by the following two methods. (1) Oxidation stability The oil from the powdered oil was extracted and the POV was measured.

[0069] (2) Sensory evaluation The flavor of the powdered oils and fats was evaluated by a panel of three experts according to the following criteria. The scores were determined through discussion among the three. 3: Strong fishy smell, fishy smell and smell of oxidized and deteriorated oil 2: There is a fishy smell, a fishy smell, or the smell of oxidized oil, which is problematic 1: Almost no fishy smell, fishy smell or smell of oxidized oil The results are shown in Table 4.

[0070] [Table 4]

[0071] As shown in Table 4, the oil-in-water emulsion compositions of the present invention in Examples 24 and 25 have high oxidation stability that can withstand the heat load during spray drying, and therefore the powdered oils spray-dried therefrom had a good flavor with reduced fishy odor, fishy odor, and oxidative deterioration odor of oil.

[0072] Reference examples 1~2 [Preparation of oil-in-water emulsion composition] The oil phase was prepared by dissolving fat d and VCP in the proportions shown in Table 5 in a four-neck flask at 95°C for 30 minutes with stirring (300-350 r / min) under a nitrogen atmosphere. After allowing to cool, it was confirmed that the oil did not become cloudy even after being left at room temperature for 1 hour. Component (D) shown in Table 5 was added to ion-exchanged water and stirred at 10,000 r / min for 2 minutes to prepare an aqueous phase. The oil phase was added to the aqueous phase and stirred at 10,000 r / min for 8 minutes to prepare oil-in-water emulsion compositions.

[0073] 〔evaluation〕 The oil-in-water emulsion compositions prepared above were subjected to a sensory evaluation. In the sensory evaluation, the "fishy odor" and "fishy odor" were evaluated in the same manner as in the evaluations of the above comparative examples and examples, with Comparative Example 1 being given a score of 5 (very strong). The results are shown in Table 5.

[0074] [Table 5]

[0075] As shown in Table 5, in the case of oil d with an ALA concentration of 10.5%, even with the addition of VCP, the fishy odor and fishy smell of the oil-in-water emulsion composition was minimal and at an acceptable level, and no problems arose.

Claims

1. The following components (A), (B), and (C): (A) An oil or fat having a diacylglycerol content of 15% by mass or more and an α-linolenic acid content of 15% by mass or more among fatty acids constituting the oil or fat. (B) Vitamin C fatty acid ester 0.020 to 1.0% by mass based on component (A) (C) Hydroxy acid or its salt: 0.15 to 6.0% by mass An oil-in-water emulsion composition comprising:

2. 2. The oil-in-water emulsion composition according to claim 1, wherein the (C) hydroxy acid or a salt thereof is at least one selected from the group consisting of citric acid, tartaric acid, malic acid, and salts thereof.

3. The oil-in-water emulsion composition according to claim 1 or 2, further comprising (D) an emulsifier.

4. 4. The oil-in-water emulsion composition according to claim 3, wherein the emulsifier (D) is at least one selected from the group consisting of modified starch, polyglycerol fatty acid ester, lecithin or enzymatic decomposition products thereof, and milk protein.

5. 5. The oil-in-water emulsion composition according to any one of claims 1 to 4, wherein the mass ratio of oil phase / aqueous phase is 5 / 95 to 80 / 20.

6. A powdered oil or fat obtained by drying the oil-in-water emulsion composition according to any one of claims 1 to 5.

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