Oil-in-water emulsion

Abstract

To provide an oil-in-water emulsion composition that contains a fat containing an abundance of α-linolenic acid 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 α-linolenic acid in constituent fatty acids; (B) 0.010-0.15 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] It is known that α-linolenic acid (C18:3, ALA), which is abundant in flaxseed, is converted into highly physiologically active eicosapentaenoic acid (C20:5) and docosahexaenoic acid (C22:6) when it enters the body, and in recent years, various functional oils and fats rich in α-linolenic acid have been proposed (for example, Patent Document 1). However, oils and fats rich in α-linolenic acid have very low oxidation stability and easily produce unpleasant odors. For this reason, antioxidants such as tocopherol, rosemary extract, ascorbic acid fatty acid ester, catechin, and lecithin are usually added to the oils and fats to prevent the deterioration of the flavor of the oils and fats.

[0003] Edible oils and fats come in the form of oil-in-water (O / W) emulsions and powdered oils and fats that are dried and powdered. Powdered oils and fats have the characteristic of being quickly soluble and dispersible 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 in which 50% by weight or more of the total constituent fatty acids are unsaturated fatty acids, a powdered base material, and water, and having excellent flavor and redispersibility in water. Patent Document 3 proposes a powdered oil containing highly unsaturated fatty acid-containing oils and fats, edible proteins, edible carbohydrates, and an edible antioxidant, having excellent water dispersibility, and having little oxidative deterioration odor after aging. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] JP 2002-138297 A [Patent Document 2] JP 2003-306693 A [Patent Document 3] JP 2019-41721 A Summary of the Invention [Problem to be solved by the invention]

[0005] According to the present inventor, vitamin C fatty acid ester is a suitable additive that can suppress the oxidation of fats and oils rich in α-linolenic acid, especially the deterioration of flavor caused by photooxidation. However, when an attempt was made to prepare an oil-in-water emulsion composition by blending fats and oils rich in α-linolenic acid with vitamin C fatty acid ester, it was found that although the oil-in-water emulsion composition can be provided with oxidation stability, immediately after the preparation of the oil-in-water emulsion composition, a fishy odor and a fishy odor different from the unpleasant odor generated by the oxidation of fats and oils are generated. Therefore, the present invention relates to providing an oil-in-water emulsion composition which contains fats and oils rich in α-linolenic acid and a vitamin C fatty acid ester, has high oxidative stability, and has little fishy or raw odor. [Means for solving the problem]

[0006] The present inventors conducted extensive research to solve the above problems and found that, even when fats and oils rich in α-linolenic acid and vitamin C fatty acid esters are used, if a hydroxy acid or a salt thereof is added to a certain range and emulsified, it is possible to obtain an oil-in-water emulsion composition and powdered oil and fat that have oxidation stability and little fishy or fishy odor.

[0007] That is, the present invention relates to a composition comprising the following components (A), (B) and (C): (A) Fats and oils in which 15% by mass or more of the constituent fatty acids are α-linolenic acid (B) Vitamin C fatty acid ester: 0.010 to 0.15% by mass based on 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 obtained by drying the oil-in-water emulsion composition. Effect of the Invention

[0008] According to the present invention, it is possible to provide an oil-in-water emulsion composition and a powdered oil having high oxidation stability, little fishy odor and raw odor, and high functionality of α-linolenic acid. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0009] The oil-in-water emulsion composition of the present invention contains (A) an oil or fat in which 15% by mass or more of the constituent fatty acids are α-linolenic acid. In this specification, "(A) an oil or fat in which 15% by mass or more of the constituent fatty acids are α-linolenic acid" is also referred to as "component (A) oil or fat". In the present invention, the content of α-linolenic acid in the fatty acids constituting the oil 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 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 45% or more, even more preferably 50% or more, even more preferably 52% or more, and from the viewpoint of oxidation stability, it is preferably 70% or less, more preferably 65% ​​or less, 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%. In this specification, the amount of fatty acid is calculated as the amount of free fatty acid.

[0010] In the present invention, the constituent fatty acids other than α-linolenic acid that constitute the 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 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 of the unsaturated fatty acids is preferably 14 to 24, and more preferably 16 to 22.

[0011] In particular, the content of linoleic acid (C18:2) in the fatty acids constituting the oils and fats 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 fats and oils is preferably 5 to 40%, more preferably 5 to 30%, and even more preferably 10 to 20%.

[0012] Furthermore, the content of oleic acid (C18:1) in the fatty acids constituting the 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 fat or oil is preferably 10 to 65%, more preferably 10 to 50%, and even more preferably 10 to 30%.

[0013] The total content of saturated fatty acids in the fatty acids constituting the oil or fat 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 standpoints of appearance, physiological effects, and industrial productivity of the oil or fat. The saturated fatty acid preferably has 14 to 24 carbon atoms, and more preferably has 16 to 22 carbon atoms.

[0014] In the present invention, the fat or oil contains at least one of monoacylglycerol, diacylglycerol, and triacylglycerol. There is no particular limitation on the type of fat or oil, and any fat or oil may be used as long as it can be used as an edible fat or oil. From the viewpoint of industrial productivity of the oil, the triacylglycerol content in the component (A) oil is preferably 88% or more, more preferably 90% or more, even more preferably 92% or more, even more preferably 95% or more, and is preferably 99.8% or less, more preferably 99.5% or less, even more preferably 99% or less. The triacylglycerol content in the component (A) oil or fat is preferably 88 to 99.8%, more preferably 90 to 99.5%, even more preferably 92 to 99.5%, and still more preferably 95 to 99%.

[0015] The content of diacylglycerol in the component (A) oil or fat is preferably 0.1% or more, more preferably 0.2% or more, and is preferably 9% or less, more preferably 7% or less, even more preferably 5% or less, and even more preferably 3% or less, from the viewpoint of industrial productivity of the oil or fat. The content of diacylglycerol in the component (A) oil or fat is preferably 0.1 to 9%, more preferably 0.1 to 7%, even more preferably 0.2 to 5%, and still more preferably 0.2 to 3%. The content of monoacylglycerol in the component (A) fat or oil is preferably 5% or less, more preferably 3% or less, even more preferably 2% or less, even more preferably 1% or less, and even more preferably 0.5% or less, from the viewpoints of flavor, industrial productivity of the fat or oil, and oxidation stability. The content of monoacylglycerol in the fat or oil may be 0%. The content of free fatty acid or its salt in the oil or fat (A) is preferably 3% or less, more preferably 2% or less, even more preferably 1% or less, and even more preferably 0.5% or less, from the viewpoints of flavor and oxidation stability. The content of free fatty acid or its salt in the oil or fat may be 0%. The fatty acid composition of the triacylglycerol, diacylglycerol and monoacylglycerol may be the same or different.

[0016] In the present invention, the oil and fat component (A) may be any of vegetable oil and fat or animal oil and fat as long as it can be used as edible oil and fat.For example, vegetable oil and fat such as soybean oil, rapeseed oil, safflower oil, rice oil, corn oil, sunflower oil, cottonseed oil, olive oil, sesame oil, peanut oil, pearl barley 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, monkey fat, shea butter, algae oil, etc.; animal oil and fat such as fish oil, lard, beef tallow, butter fat, etc.; or oil and fat such as interesterified oil, hydrogenated oil, fractionated oil, etc. thereof. Among them, from the viewpoint of usability, it is preferable to use vegetable oils and fats, more preferably liquid oils and fats with excellent low temperature resistance, and more preferably at least one oil and fat selected from perilla oil, linseed oil, perilla oil, chia seed oil and sacha inchi oil, which are rich in α-linolenic acid. Note that liquid oils and fats refer to oils and fats that are liquid at 20°C when a cooling test according to Standard Fats and Oils Analysis Test Method 2.3.8-27 is carried out.

[0017] The content of the component (A) oil or fat in the oil-in-water emulsion composition is, from the standpoints of emulsion stability, oxidation stability, flavor, and industrial productivity, 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, even more preferably 30% or more, 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%.

[0018] 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" is also 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 a commercially available product, preferably a commercially available product for food and drink, can be used. As the higher fatty acid, a linear saturated fatty acid having 12 to 22 carbon atoms is preferable. The vitamin C fatty acid ester is preferably vitamin C palmitate or vitamin C stearate, more preferably vitamin C palmitate, because it has high oxidation stability, little fishy or raw odor, and good flavor.

[0019] In the present invention, the content of component (B) in the oil-in-water emulsion composition is 0.010 to 0.15% based on component (A). From the viewpoint of oxidation stability, the content of component (B) in the oil-in-water emulsion composition is 0.010% or more based on component (A), preferably 0.020% or more, and more preferably 0.025% or more. From the viewpoint of solubility and appearance of vitamin C fatty acid ester, the content is 0.15% or less, preferably 0.10% or less, more preferably 0.070% or less, even more preferably 0.050% or less, and even more preferably 0.040% or less. The content of component (B) in the oil-in-water emulsion composition relative to component (A) is 0.010 to 0.15%, preferably 0.020 to 0.10%, more preferably 0.025 to 0.10%, even more preferably 0.025 to 0.050%, and still more preferably 0.025 to 0.040%.

[0020] 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" is also 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. The salt of the hydroxy acid is preferably an alkali metal salt, more preferably a sodium salt or a potassium salt, and even more preferably a sodium salt. 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.

[0021] 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 oxidation stability and flavor, the content of component (C) in the oil-in-water emulsion composition is 0.15% or more, preferably 0.16% or more, more preferably 0.20% or more, and even more preferably 0.30% or more, and from the viewpoints of oxidation 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, 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 0.15 to 4.0%, more preferably 0.16 to 3.0%, even more preferably 0.20 to 2.0%, and still more preferably 0.30 to 1.0%. In this specification, when component (C) is a salt or a hydrate, the content of component (C) is the value converted into the hydroxy acid, which is a free acid.

[0022] 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 the emulsifier used in the present invention include processed starch; synthetic emulsifiers such as organic acid monoglyceride, polyglycerol fatty acid ester, propylene glycol fatty acid ester, polyglycerol condensed ricinoleic acid ester, sorbitan fatty acid ester, sorbitol fatty acid ester, and sucrose fatty acid ester; and natural emulsifiers such as saponin, lecithin or its enzymatic hydrolysis product, milk protein (buttermilk powder, sodium caseinate, etc.), soy protein, wheat protein, and the like, or isolates or hydrolysis products of these proteins. These may be used alone or in combination of two or more. Among them, from the viewpoints of emulsion stability, flavor, and oxidation stability, preferably, one or more selected from processed starch, sucrose fatty acid ester, polyglycerol fatty acid ester, lecithin or its enzymatic hydrolysis product, and milk protein, more preferably, one or more selected from processed starch, sucrose fatty acid ester, polyglycerol fatty acid ester, lecithin or its enzymatic hydrolysis product, and milk protein, and further, one or more selected from milk protein. 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.); oxidation (e.g., oxidized starch treated with an oxidizing agent such as sodium hypochlorite, etc.), or a combination of these processes.

[0023] The content of component (D) in the oil-in-water emulsion composition is, from the viewpoints of emulsion stability, flavor, and oxidation stability, 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, 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%.

[0024] 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))], from the standpoints of flavor, solubility of vitamin C fatty acid ester, physiological function, and oxidative stability, is preferably 200 or more, more preferably 400 or more, even more preferably 800 or more, and even more preferably 1000 or more, and from the standpoints of flavor and oxidative stability, is preferably 8000 or less, more preferably 6000 or less, even more preferably 4000 or less, and even more preferably 3000 or less. 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 and fat [(ALA) / (component (B))] is preferably 200 to 8,000, more preferably 400 to 6,000, even more preferably 400 to 4,000, even more preferably 800 to 4,000, and even more preferably 1,000 to 3,000, from the standpoints of flavor, solubility of vitamin C fatty acid ester, physiological function, and oxidative stability.

[0025] 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 3 or more, more preferably 5 or more, and even more preferably 10 or more, from the viewpoints of flavor and oxidative stability, and is preferably 400 or less, more preferably 300 or less, even more preferably 200 or less, even more preferably 150 or less, and even more preferably 100 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 the content of component (A) to the content of component (C) in the oil-in-water emulsion composition [(component (C)) / (component (B))] is preferably 3 to 400, more preferably 3 to 300, even more preferably 3 to 200, even more preferably 5 to 150, and even more preferably 10 to 100, from the viewpoints of flavor and oxidative stability.

[0026] 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 the oil (A). The content of the oil-soluble components may be appropriately set within a range that does not impair the object of the present invention.

[0027] 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, sugar alcohols, etc.; hydrophilic antioxidants; and water-soluble components such as thickeners, preservatives, colorants, sweeteners, seasonings, fragrances, etc. In the present invention, these can be appropriately blended depending on the viscosity, physical properties, etc. 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 emulsion stability, flavor, and oxidation stability.

[0028] The blending ratio (mass ratio) of the oil phase to the aqueous 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.

[0029] The oil-in-water emulsion composition of the present invention can be produced by mixing components (A), (B) and (C), and optionally (D), according to a conventional method. Preferably, first, components (A) and (B) are mixed to prepare an oil phase. On the other hand, water and component (C), and optionally (D) are mixed to prepare an aqueous phase. Next, the oil phase is added to the aqueous phase, and preliminary emulsification is performed as necessary, followed by homogenization to obtain an oil-in-water emulsion composition. Examples of homogenizers include high-pressure homogenizers, ultrasonic emulsifiers, colloid mills, ajihomomomixers, and milders.

[0030] The oil-in-water emulsion composition thus produced may be used as it is, but is preferably dried and used as a powdered oil. The oil-in-water emulsion composition of the present invention has high oxidation stability while containing a large amount of α-linolenic acid, and has little fishy or fishy odor, so that it is possible to provide a powdered oil that contains a large amount of α-linolenic acid and has a good flavor. As the drying method, a general method can be used, for example, 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 them, spray drying is preferred from the viewpoints of productivity, heat history, and particle shape.

[0031] 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. In addition to ordinary foods and beverages, the foods and beverages include, for example, foods for specified health uses and functional foods that claim to have the physiological effects of α-linolenic acid. 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.

[0032] The oil-in-water emulsion composition of the present invention comprises the following components (A), (B) and (C) in terms of high oxidation stability, good flavor with little fishy or raw odor, and physiological effects: (A) Fats and oils in which 20 to 70% by mass of the constituent fatty acids are α-linolenic acid (B) Vitamin C fatty acid ester: 0.010 to 0.10% by mass based on component (A) (C) Hydroxy acid or its salt: 0.16 to 6.0% by mass It is preferable that the composition is an oil-in-water emulsion composition containing the above.

[0033] The oil-in-water emulsion composition of the present invention comprises the following components (A), (B), (C) and (D) in terms of high oxidation stability, good flavor with little fishy or raw odor, and physiological effects: (A) Fats and oils in which 20 to 70% by mass of the constituent fatty acids are α-linolenic acid (B) Vitamin C fatty acid ester: 0.010 to 0.10% by mass based on component (A) (C) Hydroxy acid or its salt: 0.16 to 6.0% by mass (D) Emulsifier: 0.05 to 30% by mass It is preferable that the composition is an oil-in-water emulsion composition containing the above.

[0034] The oil-in-water emulsion composition of the present invention comprises the following components (A), (B), (C) and (D) in terms of high oxidation stability, good flavor with little fishy or raw odor, and physiological effects: (A) Fats and oils in which 20 to 70% by mass of the constituent fatty acids are α-linolenic acid (B) Vitamin C fatty acid ester: 0.020 to 0.10% by mass based on component (A) (C) Hydroxy acid or its salt: 0.16 to 6.0% by mass (D) Emulsifier: 0.2 to 30% by mass It is preferable that the composition is an oil-in-water emulsion composition containing the above.

[0035] The oil-in-water emulsion composition of the present invention comprises the following components (A), (B), (C) and (D) in terms of high oxidation stability, good flavor with little fishy or raw odor, and physiological effects: (A) Fats and oils in which 25 to 70% by mass of the constituent fatty acids are α-linolenic acid (B) Vitamin C fatty acid ester: 0.025 to 0.10% by mass based on 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 the above.

[0036] In relation to the above-mentioned embodiments, the present invention further discloses the following oil-in-water emulsion composition and powdered oil.

[0037] <1> The following components (A), (B) and (C): (A) Fats and oils in which 15% by mass or more of the constituent fatty acids are α-linolenic acid (B) Vitamin C fatty acid ester: 0.010 to 0.15% by mass based on component (A) (C) Hydroxy acid or its salt: 0.15 to 6.0% by mass 1. An oil-in-water emulsion composition comprising:

[0038] <2> The content of α-linolenic acid in 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 45% 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, 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 45 to 65% by mass, even more preferably 50 to 65% by mass, and even more preferably 52 to 60% by mass. <1> 2. 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> 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 triacylglycerol in the component (A) oil or fat is preferably 88% by mass or more, more preferably 90% by mass or more, even more preferably 92% by mass or more, even more preferably 95% by mass or more, and is preferably 99.8% by mass or less, more preferably 99.5% by mass or less, even more preferably 99% by mass or less, and is preferably 88 to 99.8% by mass, more preferably 90 to 99.5% by mass, even more preferably 92 to 99.5% by mass, even more preferably 95 to 99% by mass. <1> ~ <4> 1. The oil-in-water emulsion composition according to any one of claims 1 to 9. <6> The content of diacylglycerol in the component (A) oil or fat is preferably 0.1% by mass or more, more preferably 0.2% by mass or more, and is preferably 9% by mass or less, more preferably 7% by mass or less, even more preferably 5% by mass or less, even more preferably 3% by mass or less, and is preferably 0.1 to 9% by mass, more preferably 0.1 to 7% by mass, even more preferably 0.2 to 5% by mass, even more preferably 0.2 to 3% 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% by mass or less, even more preferably 0.5% 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 is preferably 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 is preferably derived from at least one oil selected from perilla oil, linseed oil, perilla oil, chia seed oil and sacha inchi oil. <1> ~ <8> 1. The oil-in-water emulsion composition according to any one of claims 1 to 9. <10> The content of the component (A) oil or fat 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, 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, even more preferably 45% by mass or less, and also 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, even more preferably 30 to 45% by mass. <1> ~ <9> 1. The oil-in-water emulsion composition according to any one of claims 1 to 9. <11> Component (B) is preferably vitamin C palmitate, vitamin C stearate or a combination thereof, more preferably vitamin C palmitate. <1> ~ <10> 1. The oil-in-water emulsion composition according to any one of claims 1 to 9. <12> The content of component (B) in the oil-in-water emulsion composition relative to component (A) is 0.010% by mass or more, preferably 0.020% by mass or more, more preferably 0.025% by mass or more, and is 0.15% by mass or less, preferably 0.10% by mass or less, more preferably 0.070% by mass or less, even more preferably 0.050% by mass or less, even more preferably 0.040% by mass or less, and is 0.010 to 0.15% by mass, preferably 0.020 to 0.10% by mass, more preferably 0.025 to 0.10% by mass, even more preferably 0.025 to 0.050% by mass, and even more preferably 0.025 to 0.040% by mass. <1> ~ <11> 1. The oil-in-water emulsion composition according to any one of claims 1 to 9. <13> (C) 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, sodium citrate, or a combination thereof, and even more preferably sodium citrate. <1> ~ <12> 1. The oil-in-water emulsion composition according to any one of claims 1 to 9. <14> The content of component (C) in the oil-in-water emulsion composition is 0.15% by mass or more, preferably 0.16% by mass or more, more preferably 0.20% by mass or more, even more preferably 0.30% 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, even more preferably 1.0% by mass or less, and is 0.15 to 6.0% by mass, preferably 0.15 to 4.0% by mass, more preferably 0.16 to 3.0% by mass, even more preferably 0.20 to 2.0% by mass, even more preferably 0.30 to 1.0% by mass. <1> ~ <13> 1. The oil-in-water emulsion composition according to any one of claims 1 to 9. <15> Preferably, it further contains (D) an emulsifier. <1> ~ <14> 1. The oil-in-water emulsion composition according to any one of claims 1 to 9. <16> The emulsifier (D) is preferably one or more selected from modified starch, sucrose fatty acid ester, polyglycerol fatty acid ester, lecithin or its enzymatic hydrolysis product, and milk protein, more preferably one or more selected from modified starch, polyglycerol fatty acid ester, and milk protein, and even more preferably milk protein. <15> 2. The oil-in-water emulsion composition according to claim 1 . <17> 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. <15> or <16> 2. The oil-in-water emulsion composition according to claim 1 . <18> 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 200 or more, more preferably 400 or more, even more preferably 800 or more, even more preferably 1000 or more, and is preferably 8000 or less, more preferably 6000 or less, even more preferably 4000 or less, even more preferably 3000 or less, and is preferably 200 to 8000, more preferably 400 to 6000, even more preferably 400 to 4000, even more preferably 800 to 4000, even more preferably 1000 to 3000. <1> ~ <17> 1. The oil-in-water emulsion composition according to any one of claims 1 to 9. <19> 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 3 or more, more preferably 5 or more, even more preferably 10 or more, and is preferably 400 or less, more preferably 300 or less, even more preferably 200 or less, even more preferably 150 or less, even more preferably 100 or less, and is preferably 3 to 400, more preferably 3 to 300, even more preferably 3 to 200, even more preferably 5 to 150, even more preferably 10 to 100. <1> ~ <18> 1. The oil-in-water emulsion composition according to any one of claims 1 to 9. <20> 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, even more preferably 30 / 70 to 45 / 55. <1> ~ <19> 1. The oil-in-water emulsion composition according to any one of claims 1 to 9. <21> <1> ~ <20> 2. A powdered oil obtained by drying the oil-in-water emulsion composition according to any one of claims 1 to 11. <22> <1> ~ <20> The oil-in-water emulsion composition according to any one of the preceding claims, <21> A food or drink containing the powdered oil or fat described in claim 1. <23> <1> ~ <20> The oil-in-water emulsion composition according to any one of the preceding claims, <21> A feed containing the powdered oil or fat described in claim 1. EXAMPLES

[0039] [Analysis Method] (i) Glyceride Composition of Oil and Fat Approximately 10 mg of the 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] (Conditions) 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: Heating from 80 °C to 340 °C at 10 °C / min and holding for 15 minutes

[0040] (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 × 0.25 mm × 0.2 μm (manufactured by Agilent J&W) Carrier gas: 1.0 mL He / min Injector: Split (1:50), T = 300 °C Detector: FID, T = 300 °C Oven temperature: 150℃ 5min hold → 1℃ / min temperature rise → 160℃ 5min hold → 2℃ / min temperature rise → 200℃ 10min hold → 10℃ / min temperature rise → 220℃ 5min hold

[0041] (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 the mixture was stirred, followed by addition of 10 mL of THF, followed by stirring and centrifugation (3000 r / min, 10 min, 20° C.). Next, 20 mL of hexane and 10 mL of ion-exchanged water were added, followed by centrifugation (3000 r / min, 5 min, 20° C.), and the upper layer was 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.

[0042] [Raw materials] The following oils a to d were prepared. Oil A: Linseed oil (Summit Oil) Oil b: High oleic safflower oil (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 the oils and fats a to d.

[0043] [Table 1]

[0044] Vitamin C palmitate (VCP): L-ascorbic acid palmitate (manufactured by DSM) Sodium citrate: Purified sodium citrate (manufactured by Fuso Chemical Industry Co., Ltd., uses trisodium citrate dihydrate as the substance) Sodium tartrate: L-sodium tartrate (Fuso Chemical Industry Co., Ltd., uses disodium tartrate dihydrate as the substance) Sodium malate: DL-sodium malate (manufactured by Fuso Chemical Industry Co., Ltd. The substance used is disodium DL-malate 1 / 2 hydrate) Citric acid: Refined 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.) Sucrose fatty acid ester: P-1670 (Mitsubishi Chemical Foods) Polyglycerol fatty acid ester: Sunsoft Q17s (manufactured by Taiyo Kagaku) Lysolecithin: SLP-White (Tsuji Oil Mills) Buttermilk powder: Hokkaido buttermilk powder (Yotsuba Dairy) Dextrin: Sandec #100 (manufactured by Sanwa Starch Industry Co., Ltd.)

[0045] Comparative Examples 1 to 4 [Preparation of oil-in-water emulsion composition] The oil and fats and VCP were placed in a four-neck flask in the ratio shown in Table 2, and dissolved under nitrogen atmosphere at 95°C for 30 minutes with stirring (300-350 r / min) to prepare an oil phase. After cooling, it was confirmed that the oil phase did not become cloudy even when left at room temperature for 1 hour. Components (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 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.

[0046] 〔evaluation〕 The oil-in-water emulsion compositions prepared above were evaluated by the following three methods. (1) Sensory evaluation 10 g of the oil-in-water emulsion composition was placed in a 20 mL vial with a lid and stored at room temperature for 24 hours, after which it was evaluated by three expert panelists according to the following criteria: For "fishy odor" and "fishy odor," Comparative Example 1 was given a score of 5 (very strong), and the scores for Comparative Examples 1 to 4 were determined by discussion among the three panelists. 5: Very strong fishy or fishy smell 4: Strongly feel fishy and raw odor 3: Feel fishy and raw odor 2: Barely feel fishy and raw odor 1: Hardly feel fishy and raw odor

[0047] (2) 1-Penten-3-one peak area relative area ratio The analysis of 1-penten-3-one was carried out by headspace solid-phase microextraction / gas chromatography-mass spectrometry (HS-SPME / GC / MS) method. A 50 / 30μm, DVB / CAR / PDMS fiber (manufactured by SUPELCO) was used as the SPME fiber. 10 g of the water-in-oil 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 for 30 minutes with an SPME fiber, followed by analysis under the following conditions. <GC / MS analysis conditions> Apparatus: Agilent 7890A / 5975 (manufactured by Agilent Technologies) Column: VF-WAX 60 m × 0.25 mm × 1.0 μm (manufactured by Agilent J&W) Carrier gas: 1.0 mL He / min Injector: Splitless, 240°C Oven temperature: Hold at 35°C for 4 min → Heat at 3°C / min → 185°C → Heat at 10°C / min → Hold at 240°C for 10 min By using the HS-GC / MS method with SPME, the volatile components in the gas phase were analyzed, and the peak area of 1-penten-3-one, which is one of the causative components of fishy odor, was calculated by integration. The relative area ratios of Comparative Examples 2 to 4 were determined when the peak area of Comparative Example 1 was set to 1.00.

[0048] (3) Oxidation stability The oxidative stability was evaluated for those compositions that received a score of 1 (hardly noticeable) or 2 (very slightly noticeable) 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 capped vial and stored at 50° C. for 3 days, after which the oil in the oil-in-water emulsion composition was extracted and the POV was measured.

[0049] [Table 2]

[0050] As shown in Table 2, Comparative Examples 1, 2, and 4, which contained oil a or oil c and VCP, had a strong fishy odor and raw odor. Comparative Example 3, which did not contain VCP, had a small fishy odor and raw odor but had low oxidation stability.

[0051] Examples 1 to 20 [Preparation of oil-in-water emulsion composition] The fats and oils and VCP were placed in a four-neck flask in the ratios shown in Table 3, and dissolved in a nitrogen atmosphere at 95°C for 30 minutes with stirring (300-350 r / min). After cooling, it was confirmed that the oil did not become cloudy even when 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.

[0052] 〔evaluation〕 The oil-in-water emulsion compositions prepared above were evaluated by the following three methods. (1) Sensory evaluation As for the "fishy odor" and "fishy odor," the evaluation was performed in the same manner as in Comparative Examples 2 to 4, with Comparative Example 1 being given a score of 5 (very strong).

[0053] (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 calculated in the same manner as in Comparative Examples 2-4.

[0054] (3) Oxidation stability In the same manner as in Comparative Example 3, the oil-in-water emulsion composition was stored at 50° C. for 3 days, and then the POV was measured. The results are shown in Table 3.

[0055] [Table 3]

[0056] As shown in Table 3, Examples 1 to 20 had little fishy odor and fishy odor, and were better in oxidation stability than Comparative Example 3.

[0057] Examples 21 to 22 and Comparative Examples 5 to 6 [Preparation of oil-in-water emulsion composition] The oil / fat a and VCP were placed in a four-neck flask in the ratio shown in Table 4, and dissolved under a nitrogen atmosphere at 95° C. for 30 minutes with stirring (300 to 350 r / min) to prepare an oil phase. Next, the components (C), (D) and dextrin shown in Table 4 were added to the 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.

[0058] [Preparation of powdered oils and fats] 0.8 g of the oil-in-water emulsion composition obtained above was spread onto a 6 cm diameter stainless steel dish, heated and dried on a hot plate at 150°C for 3 minutes and at 80°C for 5 minutes, and then pulverized to obtain a powdered oil.

[0059] 〔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.

[0060] (2) Sensory evaluation The flavor of the powdered oils and fats was evaluated by a panel of three experts according to the criteria shown below. The scores were determined by discussion among the three experts. 1: Almost no fishy smell, raw smell or smell of oxidized oil 2: Fishy smell, raw smell, or smell of oxidized oil 3: There is a strong smell of fish, fishy smell, or oxidized / deteriorated oil. The results are shown in Table 4.

[0061] [Table 4]

[0062] As shown in Table 4, the oil-in-water emulsion composition of the present invention has high oxidation stability capable of withstanding the heat load during spray drying, and therefore the powdered oils and fats spray-dried therefrom have good flavor with reduced fishy odor, fishy odor, and oxidative deterioration odor of oil.

[0063] Reference examples 1~4 [Preparation of oil-in-water emulsion composition] The oil and fat and VCP were placed in a four-neck flask in the ratio shown in Table 5, and dissolved under nitrogen atmosphere at 95°C for 30 minutes with stirring (300-350 r / min) to prepare an oil phase. After cooling, it was confirmed that the oil did not become cloudy even when left at room temperature for 1 hour. The 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 each of the oil-in-water emulsion compositions.

[0064] 〔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 comparative examples and examples, with Comparative Example 1 being given a score of 5 (very strong). The results are shown in Table 5.

[0065] [Table 5]

[0066] As shown in Table 5, in the case of oil b with an ALA concentration of 0.2% and oil d with an ALA concentration of 11.0%, even though VCP was added, the oil-in-water emulsion composition had little fishy odor and fishy odor, and no problems occurred.

Claims

1. The following components (A), (B) and (C): (A) Fats and oils in which 15% by mass or more of the constituent fatty acids are α-linolenic acid (B) Vitamin C fatty acid ester: 0.010 to 0.15% 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: 88 to 99.8 mass% of the component (A) fat or oil is triacylglycerol, Component (C) an oil-in-water emulsion composition, wherein the hydroxy acid or a salt thereof is one or more selected from the group consisting of citric acid, tartaric acid, malic acid, and salts thereof.

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

3. 3. The oil-in-water emulsion composition according to claim 2, wherein the emulsifier (D) is at least one selected from the group consisting of modified starch, sucrose fatty acid ester, polyglycerol fatty acid ester, lecithin or an enzymatic hydrolysis product thereof, and milk protein.

4. The oil-in-water emulsion composition according to any one of claims 1 to 3, wherein the mass ratio of the oil phase to the water phase is from 5 / 95 to 80 / 20.

5. A powdered oil obtained by drying the oil-in-water emulsion composition according to any one of claims 1 to 4.

Images