JP2022088160A - Oil-in-water emulsion composition - Google Patents

Abstract

An object of the present invention is to provide an oil-in-water emulsified composition containing fats and oils rich in α-linolenic acid and vitamin C fatty acid ester, having high oxidation stability and little fishy and fishy odors. [Solution] The following components (A), (B) and (C): (A) oils and fats in which 15% by mass or more of the constituent fatty acids are α-linolenic acid (B) vitamin C fatty acid esters for component (A) 0.010 to 0.15 mass% (C) hydroxy acid or salt thereof 0.15 to 6.0 mass% oil-in-water emulsion composition. [Selection figure] None

Description

The present invention relates to an oil-in-water emulsified composition and powdered fats and oils.

Α-linolenic acid (C18: 3, ALA), which is abundant in flaxseed, is converted to highly bioactive eicosapentaenoic acid (C20: 5) and docosahexaenoic acid (C22: 6) when it enters the body. In recent years, various functional fats and oils containing abundant α-linolenic acid have been proposed (for example, Patent Document 1). However, fats and oils rich in α-linolenic acid have very low oxidative stability and easily generate an unpleasant odor. Therefore, it is usually carried out to prevent the flavor deterioration of fats and oils by adding antioxidants such as tocopherol, rosemary extract, ascorbic acid fatty acid ester, catechin and lecithin to fats and oils.

As edible oils and fats, there are oil-in-water type (O / W type) emulsified liquids and powdered oils and fats obtained by drying and powdering them. Powdered fats and oils have characteristics such as being quickly dissolved and dispersed in water, and can bring about various effects such as flavoring and texture improvement when used in foods.
For example, in Patent Document 2, a powdered fat and oil containing a glyceride mixture in which 50% by weight or more of all 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 powdered fats and oils containing highly unsaturated fatty acid-containing fats and oils, edible proteins, edible carbohydrates, and edible antioxidants, which are excellent in water dispersibility and have little oxidative deterioration odor after aging.

Japanese Unexamined Patent Publication No. 2002-138297 Japanese Patent Application Laid-Open No. 2003-306693 Japanese Unexamined Patent Publication No. 2019-41721

According to the present inventor, the vitamin C fatty acid ester is a suitable additive capable of suppressing the oxidation of fats and oils rich in α-linolenic acid, particularly the deterioration of flavor due to photooxidation. However, when an attempt was made to prepare an oil-in-water emulsified composition by blending a fat and oil rich in α-linolenic acid and a vitamin C fatty acid ester, the oil-in-water emulsified composition could be imparted with oxidative stability. Immediately after the preparation of the oil-in-water emulsified composition, it was found that a fishy odor and a fishy odor different from the unpleasant odor generated by the oxidation of fats and oils were generated.
Therefore, the present invention relates to an oil-in-water emulsified composition containing a fat and oil rich in α-linolenic acid and a vitamin C fatty acid ester, having high oxidative stability and less fishy odor and fishy odor. ..

As a result of diligent studies to solve the above problems, the present inventor has been able to emulsify by containing hydroxy acid or a salt thereof in a certain range even when a fat or oil rich in α-linolenic acid and a vitamin C fatty acid ester are used. For example, it has been found that an oil-in-water emulsified composition and powdered fats and oils having oxidative stability and less fishy odor and fishy odor can be obtained.

That is, in the present invention, 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) 0.010 to 0.15% by mass with respect to the vitamin C fatty acid ester component (A)
(C) Hydroxy acid or salt thereof 0.15 to 6.0% by mass
To provide an oil-in-water emulsified composition containing the above.
The present invention also provides powdered fats and oils obtained by drying the oil-in-water emulsified composition.

According to the present invention, it is possible to provide an oil-in-water emulsified composition and powdered fats and oils having high oxidative stability, less fishy odor and less fishy odor, and having high functionality of α-linolenic acid.

The oil-in-water emulsified composition of the present invention contains fats and oils in which 15% by mass or more of the constituent fatty acids (A) are α-linolenic acid. In the present specification, "(A) fats and oils in which 15% by mass or more of constituent fatty acids are α-linolenic acid" is also referred to as "component (A) fats and oils".
In the present invention, the content of α-linolenic acid in the fatty acid constituting the fat and oil of the component (A) fat and oil 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 fats and oils is 15% or more, preferably 20% or more, more preferably 25% or more, still more preferably 30% or more, and further. It is preferably 40% or more, more preferably 45% or more, further preferably 50% or more, still more preferably 52% or more, and from the viewpoint of oxidative stability, preferably 70% or less, more preferably 65% or less. , More preferably 60% or less.
Component (A) The content of α-linolenic acid in the fatty acids constituting the fats and oils is 15% or more, preferably 15 to 70%, more preferably 20 to 70%, still more preferably 25 to 70. %, More preferably 30 to 65%, still more preferably 40 to 65%, still more preferably 50 to 65%, still more preferably 52 to 60%.
The amount of fatty acid in the present specification is a free fatty acid equivalent.

In the present invention, the constituent fatty acids other than α-linolenic acid constituting the fats and oils are not particularly limited, and may be either saturated fatty acids or unsaturated fatty acids.
From the viewpoint of flavor and industrial productivity of fats and oils, the content of unsaturated fatty acids in the fatty acids constituting the fats and oils is preferably 60 to 100%, more preferably 70 to 100%, still more preferably 80 to 99. It is 5%. From the viewpoint of physiological effects, the number of carbon atoms of the unsaturated fatty acid is preferably 14 to 24, more preferably 16 to 22.

Among them, the content of linoleic acid (C18: 2) in the fatty acids constituting the fats and oils is preferably 5% or more, more preferably 10% or more, and preferably 40, from the viewpoint of industrial productivity. % Or less, more preferably 30% or less, still 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%, still more preferably 10 to 20%.

The content of oleic acid (C18: 1) in the fatty acids constituting the fats and oils is preferably 10% or more, preferably 65% or less, and more preferably 50% from the viewpoint of industrial productivity. Below, it is more preferably 30% or less.
The content of oleic acid in the fatty acids constituting the fats and oils is preferably 10 to 65%, more preferably 10 to 50%, still more preferably 10 to 30%.

The total content of saturated fatty acids in the fatty acids constituting the fats and oils is preferably 30% or less, more preferably 20% or less, still more preferably 10% or less, from the viewpoints of appearance, physiological effect, and industrial productivity of fats and oils. More preferably, it is 7% or less, and more preferably 0.5% or more.
The number of carbon atoms of the saturated fatty acid is preferably 14 to 24, more preferably 16 to 22.

In the present invention, the fat and oil contains any one or more of monoacylglycerol, diacylglycerol and triacylglycerol. The type of fat and oil is not particularly limited, and any fat or oil that can be used as an edible fat or oil may be used.
Component (A) The content of triacylglycerol in the fat and oil is preferably 88% or more, more preferably 90% or more, still more preferably 92% or more, still more preferably 95% from the viewpoint of industrial productivity of the fat or oil. It is more preferably 99.8% or less, more preferably 99.5% or less, still more preferably 99% or less.
The content of triacylglycerol in the component (A) fat and oil is preferably 88 to 99.8%, more preferably 90 to 99.5%, still more preferably 92 to 99.5%, still more preferably 95 to 99. %.

Component (A) The content of diacylglycerol in fats and oils is preferably 0.1% or more, more preferably 0.2% or more, and preferably 9% or less, from the viewpoint of industrial productivity of fats and oils. It is more preferably 7% or less, further preferably 5% or less, still more preferably 3% or less.
The content of diacylglycerol in the component (A) fat and oil is preferably 0.1 to 9%, more preferably 0.1 to 7%, still more preferably 0.2 to 5%, still more preferably 0.2 to 0.2. It is 3%.
Component (A) The content of monoacylglycerol in the fat and oil is preferably 5% or less, more preferably 3% or less, still more preferably 3% or less, from the viewpoint of flavor, industrial productivity of the fat and oil, and oxidative stability. It is 2% or less, more preferably 1% or less, still more preferably 0.5% or less. The content of monoacylglycerol in fats and oils may be 0%.
The content of the free fatty acid or its salt in the component (A) fat and oil is preferably 3% or less, more preferably 2% or less, still more preferably 1% or less, still more preferably, from the viewpoint of flavor and oxidative stability. Is 0.5% or less. The content of free fatty acid or a salt thereof in fats and oils may be 0%.
The fatty acid compositions of triacylglycerols, diacylglycerols and monoacylglycerols may be the same or different.

In the present invention, the component (A) fat or oil may be either a vegetable fat or an animal fat or oil as long as it can be used as an edible fat or oil. For example, soybean oil, rapeseed oil, safflower oil, rice oil, corn oil, sunflower oil, cottonseed oil, olive oil, sesame oil, peanut oil, honeybee oil, wheat germ oil, perilla oil, flaxseed oil, sesame oil, chia seed oil, sacha inch oil. , Walnut oil, kiwi seed oil, salvia seed oil, grape seed oil, macadamia nut oil, hazelnut oil, pumpkin seed oil, camellia oil, brown seed oil, borage oil, palm oil, palm olein, palm stea, palm oil, palm kernel Vegetable fats and oils such as oils, cacao fats, monkey fats, shea fats and algae oils; animal fats and oils such as fish oils, lards, beef fats and butter fats; or their ester exchange oils, hydrogenated oils and fractionated oils. Can be mentioned.
Among them, from the viewpoint of usability, it is preferable to use vegetable oil, liquid oil having excellent low temperature resistance, and perilla oil, linseed oil, and perilla oil rich in α-linolenic acid. It is preferable to use at least one oil / fat selected from chia seed oil and sacha inchi oil. The liquid fat and oil means a fat and oil that is liquid at 20 ° C. when the cooling test according to the standard fat and oil analysis test method 2.3.8-27 is carried out.

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

The oil-in-water emulsified composition of the present invention contains (B) vitamin C fatty acid ester. Hereinafter, the “vitamin C fatty acid ester” is also referred to as “component (B)” in the present specification.
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, and more preferably vitamin C palmitate, because it has high oxidative stability, has little fishy odor and fishy odor, and has a good flavor.

In the present invention, the content of the component (B) in the oil-in-water emulsified composition is 0.010 to 0.15% with respect to the component (A). The content of the component (B) in the oil-in-water emulsified composition is 0.010% or more, preferably 0.020% or more with respect to the component (A) from the viewpoint of oxidative stability. , More preferably 0.025% or more. Further, from the viewpoint of solubility and appearance of the vitamin C fatty acid ester, it is 0.15% or less, preferably 0.10% or less, more preferably 0.070% or less, still more preferably 0.050% or less. More preferably, it is 0.040% or less.
The content of the component (B) in the oil-in-water emulsified composition is 0.010 to 0.15%, preferably 0.020 to 0.10%, more preferably 0.020 to 0.10% with respect to the component (A). Is 0.025 to 0.10%, more preferably 0.025 to 0.050%, still more preferably 0.025 to 0.040%.

The oil-in-water emulsified composition of the present invention contains (C) hydroxy acid or a salt thereof. Hereinafter, in the present 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.
As the salt of hydroxy acid, an alkali metal salt is preferable, a sodium salt and a potassium salt are more preferable, and a sodium salt is further preferable. These may be used alone or in combination of two or more. The hydroxy acid or a salt thereof may be either an anhydride or a hydrate.
Among them, hydroxy acid or a salt thereof is preferably one or more selected from citric acid, tartrate acid, malic acid and salts thereof from the viewpoint of oxidative stability and flavor, and more preferably citric acid or citric acid. It is sodium, more preferably sodium citrate.

In the present invention, the content of the component (C) in the oil-in-water emulsified composition is 0.15 to 6.0%. The content of the component (C) in the oil-in-water emulsified composition is 0.15% or more, preferably 0.16% or more, more preferably 0. 20% or more, more preferably 0.30% or more, and from the viewpoint of oxidative stability and flavor, 6.0% or less, preferably 4.0% or less, more preferably 3.0%. Below, it is more preferably 2.0% or less, still more preferably 1.0% or less.
The content of the component (C) in the oil-in-water emulsified composition is 0.15 to 6.0%, preferably 0.15 to 4.0%, and more preferably 0.16 to 3.0. %, More preferably 0.20 to 2.0%, still more preferably 0.30 to 1.0%.
In the present specification, when the component (C) is a salt or a hydrate, the content of the component (C) is a value converted into a hydroxy acid which is a free acid.

It is preferable that the oil-in-water emulsified composition of the present invention further contains (D) an emulsifier in terms of emulsion stability, appearance, and industrial productivity. Hereinafter, the “emulsifier” is also referred to as “component (D)” in the present specification.
The emulsifier used in the present invention is, for example, a processed starch; a synthetic emulsifier such as an organic acid monoglyceride, a polyglycerin fatty acid ester, a propylene glycol fatty acid ester, a polyglycerin condensed ricinoleic acid ester, a sorbitan fatty acid ester, a sorbitol fatty acid ester, and a sucrose fatty acid ester. Examples include proteins such as saponin, lecithin or enzymatic decomposition products thereof, milk proteins (butter milk powder, sodium caseinate, etc.), soybean proteins, wheat proteins, and natural emulsifiers such as isolates and decomposition products of these proteins. These may be used alone or in combination of two or more. Among them, one or more selected from processed starch, sucrose fatty acid ester, polyglycerin fatty acid ester, lecithin or an enzymatic decomposition product thereof, and milk protein are preferable from the viewpoint of emulsion stability, flavor and oxidative stability. , More preferably one or more selected from processed starch, sucrose fatty acid ester, polyglycerin fatty acid ester, lecithin or an enzymatic degradation product thereof, and milk protein, and further one or more selected from milk protein.
Examples of the processed starch include etherification of hydroxypropyl starch, carboxymethyl starch, etc.; esterification of acetylated starch, octenyl succinic acid starch, phosphoric acid starch, etc.; Examples thereof include starch subjected to processing such as oxidation of oxidized starch treated with an oxidizing agent such as sodium chlorate, or a combination of these processing.

The content of the component (D) in the oil-in-water emulsified composition is preferably 0.05% or more, more preferably 0.2% or more, still more preferably 0.2% or more, from the viewpoint of emulsion stability, flavor and oxidative stability. It is 0.5% or more, more preferably 1% or more, preferably 30% or less, more preferably 10% or less, still more preferably 5% or less.
The content of the component (D) in the oil-in-water emulsified composition is preferably 0.05 to 30%, more preferably 0.2 to 10%, still more preferably 0.5 to 10%, still more preferably 1. It is ~ 5%.

In the present invention, the mass ratio of the content of the component (B) to the component (A) and the content of α-linolenic acid in the fatty acid constituting the component (A) fat and oil [(ALA) / (component (B)). )] Is preferably 200 or more, more preferably 400 or more, still more preferably 800 or more, still more preferably 800 or more, from the viewpoint of flavor, solubility of vitamin C fatty acid ester, physiological function, and oxidative stability. Is 1000 or more, and from the viewpoint of flavor and oxidative stability, it is preferably 8000 or less, more preferably 6000 or less, still more preferably 4000 or less, still more preferably 3000 or less.
In the present invention, the mass ratio of the content of the component (B) to the component (A) and the content of α-linolenic acid in the fatty acid constituting the component (A) fat and oil [(ALA) / (component (B)). )] Are preferably 200 to 8000, more preferably 400 to 6000, still more preferably 400 to 4000, still more preferably 800 to 800, from the viewpoints of flavor, solubility of vitamin C fatty acid ester, physiological function, and oxidative stability. It is 4000, more preferably 1000 to 3000.

In the present invention, the mass ratio of the content of the component (B) to the component (A) and the content of the component (C) in the oil-in-water emulsified composition [(component (C)) / (component (B)). )] Is preferably 3 or more, more preferably 5 or more, still more preferably 10 or more, and preferably 400 from the viewpoint of flavor and oxidative stability. Below, it is more preferably 300 or less, still more preferably 200 or less, still more preferably 150 or less, still more preferably 100 or less.
In the present invention, the mass ratio of the content of the component (B) to the component (A) and the content of the component (C) in the oil-in-water emulsified composition [(component (C)) / (component (B)). )] Is preferably 3 to 400, more preferably 3 to 300, still more preferably 3 to 200, still more preferably 5 to 150, still more preferably 10 to 100, from the viewpoint of flavor and oxidative stability.

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

The aqueous phase of the oil-in-water emulsified composition is not particularly limited, and water; excipients such as monosaccharides, disaccharides, starch decomposition products, sugar alcohols; hydrophilic antioxidants; thickeners, preservatives, and coloring agents. It can contain water-soluble components such as additives, sweeteners, seasonings, and fragrances. In the present invention, these can be appropriately blended according to 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 viewpoint of emulsion stability, flavor and oxidation stability.

The compounding ratio (mass ratio) of the oil phase to the aqueous phase in the oil-in-water emulsified composition is preferably 5/95 to 80/20, more preferably 8/92 to 75/25, and further preferably 10/90 to 70. / 30, more preferably 15/85 to 60/40, still more preferably 20/80 to 50/50, still more preferably 30/70 to 45/55.

The oil-in-water emulsified composition of the present invention can be produced by mixing the component (A), the component (B) and the component (C), and if necessary, the component (D) according to a conventional method. Preferably, first, the component (A) and the component (B) are mixed to prepare an oil phase. On the other hand, water and the component (C), and if necessary, the component (D) are mixed to prepare an aqueous phase. Then, an oil phase is added to the aqueous phase, and if necessary, pre-emulsification is performed to homogenize the aqueous phase, whereby an oil-in-water emulsified composition can be obtained. Examples of the homogenizer include a high-pressure homogenizer, an ultrasonic emulsifier, a colloid mill, an azihomo mixer, and a milder.

The oil-in-water emulsified composition thus produced may be used as it is, but it is preferably dried and used as a powdered oil or fat. The oil-in-water emulsified composition of the present invention has high oxidative stability while containing a large amount of α-linolenic acid, and has little fishy odor and fishy odor. Can be provided.
As the drying method, a general method can be used, and examples thereof include spray drying, freeze drying, vacuum drying, belt drying, shelf drying, drum drying and the like. If necessary, classification, granulation, pulverization, etc. may be performed in order to obtain particles having a desired particle size. Among them, spray drying is preferable from the viewpoint of productivity, heat history, and particle shape.

The oil-in-water emulsified composition and powdered fats and oils of the present invention can be used in the same manner as general edible fats and oils, and can be applied to various foods and drinks and feeds using fats and oils. Examples of foods and drinks include foods for specified health use, foods with functional claims, and the like, which advocate the physiological effect of α-linolenic acid, in addition to ordinary foods and drinks.
The form of the food and drink may be solid, semi-solid or liquid, for example, beverages, water-in-oil oil-containing foods, oil-in-water oil-containing foods, bakery foods, confectionery, frozen foods, retort foods, and even more. Examples thereof include nutritional supplement compositions such as tablets, capsules and troches.
Examples of the feed include livestock feed used for cattle, pigs, etc., small animal feed used for rabbits, mice, etc., fish and shellfish feed used for eels, shrimp, etc., pet food used for dogs, cats, etc.

The oil-in-water emulsified composition of the present invention has the following components (A), (B) and ( C):
(A) Fats and oils in which 20 to 70% by mass of the constituent fatty acids are α-linolenic acid (B) 0.010 to 0.10% by mass with respect to the vitamin C fatty acid ester component (A).
(C) Hydroxy acid or salt thereof 0.16 to 6.0% by mass
It is preferable that the oil-in-water emulsified composition contains.

The oil-in-water emulsified composition of the present invention has the following components (A), (B), ( C) and (D):
(A) Fats and oils in which 20 to 70% by mass of the constituent fatty acids are α-linolenic acid (B) 0.010 to 0.10% by mass with respect to the vitamin C fatty acid ester component (A).
(C) Hydroxy acid or salt thereof 0.16 to 6.0% by mass
(D) Emulsifier 0.05 to 30% by mass
It is preferable that the oil-in-water emulsified composition contains.

The oil-in-water emulsified composition of the present invention has the following components (A), (B), ( C) and (D):
(A) Fats and oils in which 20 to 70% by mass of the constituent fatty acids are α-linolenic acid (B) 0.020 to 0.10% by mass with respect to the vitamin C fatty acid ester component (A).
(C) Hydroxy acid or salt thereof 0.16 to 6.0% by mass
(D) Emulsifier 0.2 to 30% by mass
It is preferable that the oil-in-water emulsified composition contains.

The oil-in-water emulsified composition of the present invention has the following components (A), (B), ( C) and (D):
(A) Oils and fats in which 25 to 70% by mass of constituent fatty acids are α-linolenic acid (B) 0.025 to 0.10% by mass with respect to the vitamin C fatty acid ester component (A)
(C) Hydroxy acid or salt thereof 0.20 to 3.0% by mass
(D) Emulsifier 0.2 to 10% by mass
It is preferable that the oil-in-water emulsified composition contains.

With respect to the above-described embodiments, the present invention further discloses the following oil-in-water emulsified compositions and powdered fats and oils.

<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) 0.010 to 0.15% by mass with respect to the vitamin C fatty acid ester component (A)
(C) Hydroxy acid or salt thereof 0.15 to 6.0% by mass
An oil-in-water emulsified composition containing.

<2> Component (A) The content of α-linolenic acid in the fatty acids constituting the fats and oils is 15% by mass or more, preferably 20% by mass or more, more preferably 25% by mass or more, still more preferable. Is 30% by mass or more, more preferably 40% by mass or more, further preferably 45% by mass or more, further preferably 50% by mass or more, still more preferably 52% by mass or more, and preferably 70% by mass or less. It is preferably 65% by mass or less, more preferably 60% by mass or less, preferably 15 to 70% by mass, more preferably 20 to 70% by mass, still more preferably 25 to 70% by mass, still more preferably 30 to 30 to 70% by mass. The underwater oil type according to <1>, which is 65% by mass, more preferably 40 to 65% by mass, still more preferably 45 to 65% by mass, still more preferably 50 to 65% by mass, still more preferably 52 to 60% by mass. Emulsifying composition.
<3> Component (A) The content of linoleic acid in the fatty acids constituting the fats and oils is preferably 5% by mass or more, more preferably 10% by mass or more, and preferably 40% by mass or less. It is preferably 30% by mass or less, more preferably 20% by mass or less, preferably 5 to 40% by mass, more preferably 5 to 30% by mass, still more preferably 10 to 20% by mass <1> or. The oil-in-water emulsified composition according to <2>.
<4> Component (A) The content of oleic acid in the fatty acids constituting the fats and oils is preferably 10% by mass or more, preferably 65% by mass or less, more preferably 50% by mass or less, and further. It is preferably 30% by mass or less, preferably 10 to 65% by mass, more preferably 10 to 50% by mass, still more preferably 10 to 30% by mass, to any one of <1> to <3>. The oil-in-water emulsified composition according to the above.
<5> Component (A) The content of triacylglycerol in the fat and oil is preferably 88% by mass or more, more preferably 90% by mass or more, still more preferably 92% by mass or more, still more preferably 95% by mass or more. Further, it is preferably 99.8% by mass or less, more preferably 99.5% by mass or less, further preferably 99% by mass or less, and preferably 88 to 99.8% by mass, more preferably 90 to 99% by mass. It is 5.5% by mass, more preferably 92 to 99.5% by mass, still more preferably 95 to 99% by mass. The oil-in-water emulsified composition according to any one of <1> to <4>.
<6> Component (A) The content of diacylglycerol in the fat and oil is preferably 0.1% by mass or more, more preferably 0.2% by mass or more, and preferably 9% by mass or less, more preferably. It is 7% by mass or less, more preferably 5% by mass or less, further preferably 3% by mass or less, preferably 0.1 to 9% by mass, more preferably 0.1 to 7% by mass, still more preferably 0. . The oil-in-water emulsified composition according to any one of <1> to <5>, which is 2 to 5% by mass, more preferably 0.2 to 3% by mass.
<7> Component (A) The content of monoacylglycerol in the fat and oil is preferably 5% by mass or less, more preferably 3% by mass or less, still more preferably 2% by mass or less, still more preferably 1% by mass or less. The oil-in-water emulsified composition according to any one of <1> to <6>, more preferably 0.5% by mass or less, and preferably more than 0% by mass.
<8> Component (A) The content of free fatty acid or a salt thereof in the oil / fat is preferably 3% by mass or less, more preferably 2% by mass or less, still more preferably 1% by mass or less, and preferably 0. The oil-in-water emulsified composition according to any one of <1> to <7>, which is by mass%.
<9> The component (A) is described in any one of <1> to <8>, wherein the oil and fat is preferably derived from at least one oil and fat selected from perilla oil, flaxseed oil, perilla oil, chia seed oil and sacha inchi oil. Oil-in-water emulsified composition.
<10> The content of the component (A) fat and oil in the oil-in-water emulsified composition is preferably 5% by mass or more, more preferably 8% by mass or more, still more preferably 10% by mass or more, still more preferably 15% by mass. The above is more preferably 20% by mass or more, further preferably 30% by mass or more, still preferably 80% by mass or less, more preferably 75% by mass or less, still more preferably 70% by mass or less, still more preferably 60% by mass. % Or less, more preferably 50% by mass or less, still more preferably 45% by mass or less, still preferably 5 to 80% by mass, more preferably 8 to 75% by mass, still more preferably 10 to 70% by mass, and further. The oil-in-water emulsified composition according to any one of <1> to <9>, preferably 15 to 60% by mass, more preferably 20 to 50% by mass, still more preferably 30 to 45% by mass.
<11> The oil-in-water oil according to any one of <1> to <10>, wherein the component (B) is preferably vitamin C palmitate, vitamin C stearate or a combination thereof, and more preferably vitamin C palmitate. Molded emulsified composition.
<12> The content of the component (B) in the oil-in-water emulsified composition is 0.010% by mass or more, preferably 0.020% by mass or more, based on the component (A). It is preferably 0.025% by mass or more, and 0.15% by mass or less, preferably 0.10% by mass or less, more preferably 0.070% by mass or less, and further preferably 0.050% by mass. Hereinafter, it is more preferably 0.040% by mass or less, and more preferably 0.010 to 0.15% by mass, preferably 0.020 to 0.10% by mass, and more preferably 0.025 to 0%. The oil-in-water emulsified composition according to any one of <1> to <11>, which is 10% by mass, more preferably 0.025 to 0.050% by mass, still more preferably 0.025 to 0.040% by mass. thing.
<13> (C) Hydroxy acid or a salt thereof is preferably one or more selected from citric acid, tartrate acid, malic acid and salts thereof, and more preferably citric acid, sodium citrate or a combination thereof. The oil-in-water emulsified composition according to any one of <1> to <12>, which is more preferably sodium citrate.
<14> The content of the component (C) in the oil-in-water emulsified composition is 0.15% by mass or more, preferably 0.16% by mass or more, and more preferably 0.20% by mass or more. It is more preferably 0.30% by mass or more, and more preferably 6.0% by mass or less, preferably 4.0% by mass or less, still more preferably 3.0% by mass or less, still more preferably 2.0. It is 0% by mass or less, more preferably 1.0% by mass or less, and 0.15 to 6.0% by mass, preferably 0.15 to 4.0% by mass, and more preferably 0.16 to 0.16% by mass. The underwater oil type according to any one of <1> to <13>, which is 3.0% by mass, more preferably 0.20 to 2.0% by mass, still more preferably 0.30 to 1.0% by mass. Emulsifying composition.
<15> The oil-in-water emulsified composition according to any one of <1> to <14>, which further contains (D) an emulsifier.
<16> The emulsifier (D) is preferably one or more selected from processed starch, sucrose fatty acid ester, polyglycerin fatty acid ester, lecithin or an enzymatic decomposition product thereof, and milk protein, and more preferably processed starch and poly. The oil-in-water emulsifying composition according to <15>, which is one or more selected from a glycerin fatty acid ester and a milk protein, and more preferably a milk protein.
<17> The content of the component (D) in the oil-in-water emulsified composition is preferably 0.05% by mass or more, more preferably 0.2% by mass or more, still more preferably 0.5% by mass or more, and further. It is preferably 1% by mass or more, preferably 30% by mass or less, more preferably 10% by mass or less, still more preferably 5% by mass or less, and preferably 0.05 to 30% by mass, more preferably. The oil-in-water emulsified composition according to <15> or <16>, wherein is 0.2 to 10% by mass, more preferably 0.5 to 10% by mass, still more preferably 1 to 5% by mass.
<18> Mass ratio of the content of the component (B) to the component (A) and the content of α-linolenic acid in the fatty acid constituting the component (A) fat [(ALA) / (component (B)) ], Is preferably 200 or more, more preferably 400 or more, still more preferably 800 or more, still more preferably 1000 or more, and preferably 8000 or less, more preferably 6000 or less, still more preferably 4000 or less, still more preferably. Of <1> to <17>, which is 3000 or less, preferably 200 to 8000, more preferably 400 to 6000, still more preferably 400 to 4000, still more preferably 800 to 4000, still more preferably 1000 to 3000. The oil-in-water emulsified composition according to any one.
<19> Mass ratio of the content of the component (B) to the component (A) to the content of the component (C) in the oil-in-water emulsified composition [(component (C)) / (component (B)) ], Is preferably 3 or more, more preferably 5 or more, still more preferably 10 or more, and preferably 400 or less, more preferably 300 or less, still more preferably 200 or less, still more preferably 150 or less. It is more preferably 100 or less, still more preferably 3 to 400, more preferably 3 to 300, still more preferably 3 to 200, still more preferably 5 to 150, still more preferably 10 to 100 <1> to. The oil-in-water emulsified composition according to any one of <18>.
<20> The blending ratio (mass ratio) of the oil phase and the aqueous phase is preferably 5/95 to 80/20, more preferably 8/92 to 75/25, still more preferably 10/90 to 70/30, and further. The underwater oil type according to any one of <1> to <19>, preferably 15/85 to 60/40, more preferably 20/80 to 50/50, still more preferably 30/70 to 45/55. Emulsifying composition.
<21> A powdered fat or oil obtained by drying the oil-in-water emulsified composition according to any one of <1> to <20>.
<22> A food or drink containing the oil-in-water emulsified composition according to any one of <1> to <20> or the powdered oil and fat according to <21>.
<23> A feed containing the oil-in-water emulsified composition according to any one of <1> to <20> or the powdered oil and fat according to <21>.

[Analysis method]
(I) Glycemic composition of fats and oils To a glass sample bottle, about 10 mg of fats and oils sample and 0.5 mL of a trimethylsilylating agent (“silylating agent TH”, manufactured by Kanto Chemical Co., Inc.) were added, sealed, and heated at 70 ° C. for 15 minutes. To this, 1.0 mL of water and 1.5 mL of hexane were added and shaken. After standing, the upper layer was subjected to gas chromatography (GLC) for analysis.
<GLC analysis conditions>
(conditions)
Equipment: Agilent 7890B (manufactured by Agilent Technologies)
Column: DB-1ht 10m x 0.25mm x 0.2μm (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: Raise from 80 ° C to 340 ° C at 10 ° C / min and hold for 15 minutes

(Ii) Composition of fats and oils Fatty acid composition Fatty acid methyl esters are prepared and obtained according to "Preparation method of fatty acid methyl ester (2.4.1.-1996)" in "Standard fat and oil analysis test method" edited by Japan Oil Chemistry Society. Oil samples were prepared from American Oil Chemists. Measurement was performed according to Society Official Method Ce 1f-96 (GLC method).
<GLC analysis conditions>
Equipment: Agilent 7890B (manufactured by Agilent Technologies)
Column: CP-SIL88 50m x 0.25mm x 0.2μm (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 ° C 5 min retention → 1 ° C / min temperature rise → 160 ° C 5 min retention → 2 ° C / min temperature rise → 200 ° C 10 min retention → 10 ° C / min temperature rise → 220 ° C 5 min retention

(Iii) Measurement of peroxide value (POV) Add 5 mL of ion-exchanged water to about 2.5 g of oil-in-water emulsified composition, stir, add 10 mL of THF, stir and centrifuge (3000 r / min, 10 minutes, 20). ℃). Then, 20 mL of hexane and 10 mL of ion-exchanged water were added and centrifuged (3000 r / min, 5 minutes, 20 ° C.), and then the upper layer was taken and the solvent was distilled off with a rotary evaporator to prepare oils and fats.
The POV of the extracted fats and oils was measured based on the standard fats and oils analysis method (JOCS) 2.5.2.2-2013.

〔material〕
The following fats and oils a to d were prepared.
Oil a: Flaxseed oil (made by Summit Oil)
Oil b: High oleic safflower oil (manufactured by J-Oil Mills)
Oil c: Oil a and oil b were mixed at a mass ratio of 1: 1 to obtain oil c.
Oil d: Oil a and oil b were mixed at a mass ratio of 1: 4 to obtain oil d.
Table 1 shows the glyceride composition and the fatty acid composition of the fats and oils a to d.

Vitamin C palmitate (VCP): L-ascorbic acid palmitic acid ester (manufactured by DSM)
Sodium citrate: Purified sodium citrate (using trisodium citrate dihydrate as a substance manufactured by Fuso Chemical Industry Co., Ltd.)
Sodium tartrate: L-sodium tartrate (use disodium tartrate dihydrate as a substance manufactured by Fuso Chemical Industry)
Sodium malate: DL-sodium malate (DL-disodium malate 1/2 hydrate is used as a substance manufactured by Fuso Chemical Industry Co., Ltd.)
Citric acid: Purified citric acid (manufactured by Fuso Chemical Industry Co., Ltd.)
Modified starch: Emulstar 500A (manufactured by Matsutani Chemical Industry Co., Ltd.)
Sodium casein: Sodium casein AR (manufactured by Saneigen FFI)
Sucrose fatty acid ester: P-1670 (manufactured by Mitsubishi Chemical Foods)
Polyglycerin fatty acid ester: Sunsoft Q17s (manufactured by Taiyo Kagaku)
Lysolecithin: SLP-White (made by Tsuji Oil)
Buttermilk powder: Hokkaido buttermilk powder (manufactured by Yotsuba Milk Products Co., Ltd.)
Dextrin: Sandeck # 100 (manufactured by Sanwa Cornstarch Co., Ltd.)

Comparative Examples 1 to 4
[Preparation of oil-in-water emulsified composition]
The oil and fat and VCP were put into a four-necked flask at the ratio shown in Table 2 and dissolved in a nitrogen atmosphere at 95 ° C. for 30 minutes (300 to 350 r / min) to prepare an oil phase. After allowing to cool, it was confirmed that the oil phase did not become turbid even when left at room temperature for 1 hour.
The components (C) and (D) shown in Table 2 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 an oil-in-water emulsified composition.

〔evaluation〕
The oil-in-water emulsified composition prepared above was evaluated by the following three methods.
(1) Sensory evaluation 10 g of an oil-in-water emulsified composition was placed in a 20 mL vial with a lid, stored at room temperature for 24 hours, and then evaluated by three expert panels according to the criteria shown below. Regarding "fishy odor" and "fishy odor", the score of Comparative Example 1 was set to 5 (it feels very strong), and the scores of Comparative Examples 1 to 4 were determined by discussion of three people.
5: Very strong fishy and fishy odors 4: Strongly felt fishy and fishy odors 3: Feeling fishy and fishy odors 2: Very slight fishy and fishy odors 1: Fishy and fishy odors I hardly feel

(2) 1-Pentene-3-on peak area relative area ratio The analysis of 1-Pentene-3-on was performed by the headspace solid-phase microextraction / gas chromatograph mass spectrometry (HS-SPME / GC / MS) method. .. As the SPME fiber, 50/30 μm, DVB / CAR / PDMS fiber (manufactured by SUPELCO) was used.
Place 10 g of the oil-in-water emulsified composition in a 20 mL vial with a lid, store at room temperature for 24 hours, weigh 1 g of the sample into a headspace vial (10 mL), heat at 40 ° C. for 20 minutes, and then use SPME fiber. After sampling the headspace phase for 30 minutes, analysis was performed under the following conditions.
<GC / MS analysis conditions>
Equipment: Agilent 7890A / 5975 (manufactured by Agilent Technologies)
Column: VF-WAX 60m x 0.25mm x 1.0μm (manufactured by Agilent J & W)
Carrier gas: 1.0 mL He / min
Injector: Splitless, 240 ° C
Oven temperature: 35 ° C 4 min maintenance → 3 ° C / min temperature rise → 185 ° C → 10 ° C / min temperature rise → 240 ° C 10 min maintenance Analysis of volatile components in the gas phase by HS-GC / MS method using SPME Then, the peak area area of 1-pentene-3-one, which is one of the causative components of fishy odor, was calculated by integration. The relative area ratio of Comparative Examples 2 to 4 was obtained when the peak area area of Comparative Example 1 was 1.00.

(3) Oxidation stability In the above sensory evaluation, the oxidative stability was evaluated for those having a score of 1 (almost no feeling) or 2 (very slight feeling). In the evaluation of oxidative stability, 10 g of the oil-in-water emulsified composition was placed in a 20 mL vial with a lid, stored at 50 ° C. for 3 days, and then the oil of the oil-in-water emulsified composition was extracted and POV was measured.

As shown in Table 2, Comparative Examples 1, 2 and 4 in which the fat a or the fat c and VCP were blended had a strong fishy odor and fishy odor. Comparative Example 3 in which VCP was not blended had less fishy odor and fishy odor, but had low oxidative stability.

Examples 1 to 20
[Preparation of oil-in-water emulsified composition]
Oils and fats and VCP were placed in a four-necked flask at the ratios shown in Table 3 and dissolved in a nitrogen atmosphere at 95 ° C. for 30 minutes (300 to 350 r / min). After allowing to cool, it was confirmed that the oil did not become turbid even when left at room temperature for 1 hour.
The components (C) and (D) shown in Table 3 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 an oil-in-water emulsified composition.

〔evaluation〕
The oil-in-water emulsified composition prepared above was evaluated by the following three methods.
(1) Sensory evaluation Regarding "fishy odor" and "fishy odor", the score of Comparative Example 1 was evaluated as 5 (feels very strong) in the same manner as the evaluation of Comparative Examples 2 to 4.

(2) 1-Pentene-3-on Peak Area Relative Area Ratio The peak area area of Comparative Example 1 was set to 1.00, and the relative area ratio was obtained in the same manner as in Comparative Examples 2 to 4.

(3) Oxidation Stability In the same manner as in Comparative Example 3, the POV of the oil-in-water emulsified composition after storage at 50 ° C. for 3 days was measured.
The results are shown in Table 3.

As shown in Table 3, Examples 1 to 20 had less fishy odor and fishy odor, and their oxidative stability was better than that of Comparative Example 3.

Examples 21 to 22 and Comparative Examples 5 to 6
[Preparation of oil-in-water emulsified composition]
The oil and fat a and VCP were put into a four-necked flask at the ratios shown in Table 4 and dissolved in a nitrogen atmosphere at 95 ° C. for 30 minutes (300 to 350 r / min) to prepare an oil phase.
Then, the components (C), (D) and dextrin shown in Table 4 were added to the ion-exchanged water, and the mixture was 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 an oil-in-water emulsified composition.

[Preparation of powdered fats and oils]
0.8 g of the oil-in-water emulsified composition obtained above is spread on a stainless steel petri dish having a diameter of 6 cm, heated and dried at 150 ° C. for 3 minutes and 80 ° C. for 5 minutes on a hot plate, and then pulverized to produce powdered oil and fat. Got

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

(2) Sensory evaluation The flavor of powdered fats and oils was evaluated by three expert panels according to the criteria shown below. The score was decided by the discussion of three people.
1: Almost no fishy odor, fishy odor and oxidative deterioration odor of oil 2: Feel fishy odor, fishy odor and oxidative deterioration odor of oil 3: Strongly feel fishy odor, fishy odor and oxidative deterioration odor of oil It is shown in Table 4.

As shown in Table 4, the oil-in-water emulsified composition of the present invention has high oxidative stability that can withstand the heat load during spray drying. The oxidative deterioration odor was suppressed and the flavor was good.

Reference examples 1 to 4
[Preparation of oil-in-water emulsified composition]
The oil and fat and VCP were placed in a four-necked flask at the ratios shown in Table 5 and dissolved in a nitrogen atmosphere at 95 ° C. for 30 minutes (300 to 350 r / min) to prepare an oil phase. After allowing to cool, it was confirmed that the oil did not become turbid even when left at room temperature for 1 hour.
The component (D) shown in Table 5 was 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 an oil-in-water emulsified composition.

〔evaluation〕
The oil-in-water emulsified composition prepared above was subjected to sensory evaluation. In the sensory evaluation, the "fishy odor" and the "fishy odor" were evaluated with a score of 5 (feeling very strongly) in Comparative Example 1 as in the evaluation of Comparative Examples and Examples.
The results are shown in Table 5.

As shown in Table 5, in the oils and fats b having an ALA concentration of 0.2% and the oils and fats d having an ALA concentration of 11.0%, even if VCP is added, the fish odor and fishy odor of the oil-in-water emulsified composition are small, and the problem is It did not occur.

Claims (7)

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) 0.010 to 0.15% by mass with respect to the vitamin C fatty acid ester component (A)
(C) Hydroxy acid or salt thereof 0.15 to 6.0% by mass
An oil-in-water emulsified composition containing. The oil-in-water emulsified composition according to claim 1, wherein 88 to 99.8% by mass of the component (A) fat and oil is triacylglycerol. (C) The oil-in-water emulsified composition according to claim 1 or 2, wherein the hydroxy acid or a salt thereof is one or more selected from citric acid, tartaric acid, malic acid and salts thereof. The oil-in-water emulsified composition according to any one of claims 1 to 3, further comprising (D) an emulsifier. (D) The oil-in-water emulsified composition according to claim 4, wherein the emulsifier is one or more selected from processed starch, sucrose fatty acid ester, polyglycerin fatty acid ester, lecithin or an enzymatic decomposition product thereof, and milk protein. The oil-in-water emulsified composition according to any one of claims 1 to 5, wherein the mass ratio of the oil phase / the aqueous phase is 5/95 to 80/20. A powdered fat or oil obtained by drying the oil-in-water emulsified composition according to any one of claims 1 to 6.