JP2003049189A - Powdered fat containing new highly-branched cyclic dextrin, method for producing the same, and food and drink given by utilizing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a powdered fat having good fluidity, excellent dispensability into water, excellent oxidative stability, and excellent sustainability of flavor, and to provide a method for producing the same. SOLUTION: This method for producing the powdered fat includes a process for mixing a fatty acid ester and a highly-branched cyclic dextrin with water so as to form a liquid composition for the powdered fat and the other process for drying the liquid composition. The powdered fat containing the fatty acid ester and the highly-branched cyclic dextrin, the composition for the powdered fat containing the same, and food and drink containing the powdered fat are provided in the specification, respectively.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a powdery fat and oil, a method for producing the same, a powdery fat and oil composition, and a composition containing the powdery fat and oil.

[0002]

BACKGROUND OF THE INVENTION Oils and fats are components generally extracted from animals and plants, and are used for improving the flavor and texture of foods. Recently, it has been recognized that fats and oils have important functions as nutrients. Therefore, fats and oils are important as raw materials for various foods.

With the recent trend toward health, various oils and fats have been developed and used in foods. For example, polyunsaturated fatty acids such as eicosapentaenoic acid (also referred to as EPA) and docosahexaenoic acid (DHA) are useful for preventing cardiovascular diseases, promoting brain development, maintaining and improving memory / learning function, and anti-inflammatory. It was clarified that it has functions such as an antitumor effect. Therefore, in order to impart such a function to fats and oils, attempts have been made to develop fats and oils to which these highly unsaturated fatty acids are added.

However, the polyunsaturated fatty acids and fats and oils containing them are apt to be oxidized, and have the drawback of lacking stability. Further, although fish oil contains a large amount of these highly unsaturated fatty acids, it is difficult to remove the peculiar fish odor, which makes it difficult to use as a food.

Oils and fats are usually used in the form of liquid oils such as tempura oil and plastic oils and fats such as margarine and shortening. However, depending on the application, it may be easier to use the oil and fat in the powder state. Oils and fats are usually
It can be powdered by the following methods (1) to (4).

(1) Fats and oils, proteins such as casein soda, whey protein and egg white, oligosaccharides such as sucrose and lactose, an aqueous solution of starch or its degradation product or cellulose, glycerin fatty acid ester, lecithin,
A method in which an emulsion is prepared using an emulsifier such as sorbitan fatty acid ester and sucrose fatty acid ester as a raw material, and the emulsion is spray-dried (spray dry method: JP-B-41-1415); (3) A method of spraying solid fats and oils in a molten state in a low temperature atmosphere, coagulating and powdering (spray cool method); and (4) After preparing an emulsion in the same manner as in (1) above, Vacuum freeze-drying device A method of drying using a belt type continuous vacuum drying device or a drum type vacuum drying device.

Among the above-mentioned methods, the spray dry method (1) has a coating film of an excipient formed on the surface of the powdered fat and oil, and therefore, compared with powdered fats and oils produced by other methods, The method is generally used because it has good quality stability and can keep manufacturing cost low.

[0008] In order to obtain powdery fats and oils by the spray drying method, usually, as an excipient for coating fats and oils,
Sugars such as glucose, lactose, sucrose, dextrin, and modified starch, and / or proteins such as casein soda, gelatin, and milk are used.

However, in the spray-drying method, since peroxide is generated during spray-drying, the obtained powdery fat and oil contains peroxide and is not suitable as a raw material for food. The production of peroxides is particularly remarkable when fats and oils containing a large amount of highly unsaturated fatty acids are used.

In order to suppress oxidation during spray drying of fats and oils, it is conceivable to add an antioxidant usually used for fats and oils. However, an antioxidant capable of exerting an excellent antioxidant action on oils and fats containing a large amount of highly unsaturated fatty acids has not yet been obtained.

Further, the main powder characteristics required for powdery fats and oils are: smooth feel and good fluidity, dispersibility in water.

However, the above two characteristics are substantially opposite to each other. To obtain good liquidity,
It is necessary to firmly coat the oil and fat with protein to prevent the oil and fat from seeping out. However, when the oil and fat are firmly coated,
The dispersibility of powdery fats and oils in water deteriorates.

On the other hand, in order to obtain dispersibility in water, it is necessary to make the amount of protein used as a film as small as possible. However, if the amount of protein is too small, the lipid may ooze out. In addition, increasing the affinity for water means that it tends to absorb moisture during storage, and it is sufficiently conceivable that blocking will occur.

As described above, it is desired to provide a powdery fat and oil which has good fluidity and good dispersibility in water regardless of the melting point and type of the fat and oil contained in the powdery fat and oil. . Compared to powdery fats and oils obtained by the conventional spray drying method, less peroxide is generated during spray drying, and powdery fats and oils excellent in oxidative stability and flavor maintenance, especially highly unsaturated fatty acids, are added in a large amount. It is also desirable to obtain powdered fats and oils containing.

[0015]

DISCLOSURE OF THE INVENTION The present invention is intended to solve the above problems, and provides a powdery fat or oil having good fluidity and excellent dispersibility in water, and stable oxidation. It is an object of the present invention to provide powdery fats and oils excellent in maintaining properties and flavors, and to provide a method for producing these powdery fats and oils.

[0016]

Means for Solving the Problems The inventors of the present invention have intensively studied to develop a powdery fat and oil having the above-mentioned preferable properties in order to solve the above-mentioned problems, and as a result, have incorporated a highly branched cyclic dextrin into the fat and oil. It was found that by this, powdery fats and oils having good fluidity and easy handling and excellent dispersibility in water in a wide temperature range from low temperature to high temperature can be obtained, and based on this, the present invention was completed.

When powdered oils and fats were prepared using a spray-drying apparatus using highly branched cyclic dextrin, it was found that even if oils and fats that were liquid at room temperature, such as fish oil, were used, very dry powdered oils and fats could be obtained. . In addition, when the highly branched cyclic dextrin is not used, the fish odor strongly remains in the spray drying device and cannot be used for the next production without washing, whereas when the highly branched cyclic dextrin is used, almost no odor remains in the device. I knew it wasn't.

Further, by blending the highly branched cyclic dextrin with the oil and fat, the oil and fat containing a large amount of highly unsaturated fatty acid is effectively surface-treated, so that the generation of peroxide due to heat history is suppressed and the oil and fat are preserved. It was also found that the antioxidant function works even in the state, and powdery fats and oils excellent in oxidative stability and flavor maintenance are obtained.

The powdery fat and oil of the present invention contains a fatty acid ester and a hyperbranched cyclic dextrin, and the fatty acid constituting the fatty acid ester contains a highly unsaturated fatty acid.

[0020] In one embodiment, the polyunsaturated fatty acid may contain three or more double bonds in one molecule.

[0021] In one embodiment, the polyunsaturated fatty acid may be a long chain fatty acid and may be selected from the group consisting of dihomo-γ-linolenic acid, eicosapentaenoic acid, docosapentaenoic acid and arachidonic acid.

The powdery fat and oil of the present invention may further contain an emulsifier.

The powdery fat and oil of the present invention may further contain an excipient.

The method for producing powdery fats and oils of the present invention includes the steps of mixing a fatty acid ester, a highly branched cyclic dextrin and water to obtain a liquid composition for powdery fats and oils, and a step of drying the liquid composition. The fatty acids forming the fatty acid ester include highly unsaturated fatty acids.

In one embodiment, the liquid composition for powdered fats and oils may further contain an emulsifier.

[0026] In one embodiment, the drying step may be performed by spray drying.

The powdery fat and oil composition of the present invention contains a fatty acid ester and a highly branched cyclic dextrin, and the fatty acid constituting the fatty acid ester contains a highly unsaturated fatty acid.

The food or drink of the present invention contains any of the above fats and oils.

[0029]

BEST MODE FOR CARRYING OUT THE INVENTION The present invention will be described in detail below.

<Material for Powdered Oil and Fat> The powdered oil and fat of the present invention contains a fatty acid ester and a highly branched cyclic dextrin.

In the present specification, "powdered oil and fat" refers to powder containing fatty acid ester. The powdered fat / oil usually contains about 10% by weight or more of a fatty acid ester, preferably about 20% by weight or more, based on the weight of the entire powdered fat / oil.
More preferably about 50 wt% or more, and even more preferably about 70 wt% or more fatty acid ester is contained. Powdered fats and oils are usually aggregates of small solid particles. “Powder” means a set of small solids in a state where there is no strong adhesive force between the solids. The average diameter of the solid particles of the powdery fat and oil is typically 1 cm or less, preferably 5 mm or less, more preferably 3 mm or less, still more preferably 1000 μm or less, and particularly preferably 500 μm or less. The diameter of the solid particles of the powdery fat and oil does not necessarily have to be uniform, but is preferably in a relatively narrow range. The ratio of the minimum diameter to the maximum diameter of the solid particles is preferably 100 or less, more preferably 50 or less, even more preferably 10 or less.

The powdery fat and oil of the present invention is produced from the powdery fat and oil composition.

(1) Fatty acid ester: The powdery fat and oil composition contains "fatty acid ester" as the first component.
The term "fatty acid ester" refers to an ester bond of fatty acid and alcohol, which does not have an emulsifying action.

The fatty acid constituting the fatty acid ester may be an aliphatic monocarboxylic acid or an aliphatic dicarboxylic acid. Preferably, it is an aliphatic monocarboxylic acid.

The fatty acid may be saturated fatty acid or unsaturated fatty acid. Fatty acids that do not contain double bonds are called saturated fatty acids. Examples of saturated fatty acids include butyric acid (C4:
0), caproic acid (C6: 0), caprylic acid (C8:
0), capric acid (C10: 0), lauric acid (C1
2: 0), myristic acid (C14: 0), palmitic acid (C16: 0), stearic acid (C18: 0), arachidic acid (C20: 0), behenic acid (C22: 0), lignoceric acid (C24: 0), cerotic acid (C26:
0), montanic acid (C28: 0), melicinic acid (C3
0: 0) and the like.

Fatty acids containing double bonds are called unsaturated fatty acids. Examples of unsaturated fatty acids include myristoleic acid (C
14: 1), palmitooleic acid (C16: 1), oleic acid (C18: 1), linoleic acid (C18: 2), linolenic acid (C18: 3), γ-linolenic acid (C18 :).
3), eicosenoic acid (C20: 1), dihomo-γ-linolenic acid (C20: 3), arachidonic acid (C20: 4),
Eicosapentaenoic acid (C20: 5), erucic acid (C2
2: 1), docosapentaenoic acid (C22: 5), docosahexaenoic acid (C22: 6) and the like.

A fatty acid containing two or more double bonds in one molecule is called a polyunsaturated fatty acid. Examples of polyunsaturated fatty acids include linoleic acid (C18: 2), linolenic acid (C1
8: 3), γ-linolenic acid (C18: 3), dihomo-γ.
-Linolenic acid (C20: 3), arachidonic acid (C20:
4), eicosapentaenoic acid (C20: 5), docosapentaenoic acid (C22: 5), docosahexaenoic acid (C2)
2: 6) and the like. Preferably, the polyunsaturated fatty acid contains 3 or more double bonds. Examples of highly unsaturated fatty acids containing three or more double bonds include γ-linolenic acid (C18: 3) and dihomo-γ-linolenic acid (C20:
3), arachidonic acid (C20: 4), eicosapentaenoic acid (C20: 5), docosapentaenoic acid (C22:
5), docosahexaenoic acid (C22: 6) and the like. More preferably, the polyunsaturated fatty acid contains 4 or more double bonds. Examples of highly unsaturated fatty acids containing four or more double bonds include arachidonic acid (C20: 4), eicosapentaenoic acid (C20: 5), docosapentaenoic acid (C22: 5), docosahexaenoic acid (C22: 6). ) And the like.

The amount of the polyunsaturated fatty acid in the fatty acid ester is preferably 1 to 90 mol%, more preferably 10 to 90% by mol based on the total amount of the fatty acids present in the fatty acid ester.
It is 80 mol%, and even more preferably 20 to 70 mol%.

The fatty acids can be of any chain length. Fatty acids having 6 or less carbon atoms are called short-chain fatty acids, and have 7 to 1 carbon atoms.
Fatty acids of 3 are called medium chain fatty acids, and fatty acids having 14 or more carbon atoms are called long chain fatty acids. The fatty acids are preferably medium chain fatty acids and long chain fatty acids, more preferably long chain fatty acids. The upper limit of the chain length is not particularly limited, but it is preferably 50 or less carbon atoms, more preferably 40 or less carbon atoms, and further preferably 30 or less carbon atoms. Examples of long chain fatty acids include myristic acid (C14: 0), palmitic acid (C16: 0), stearic acid (C18: 0), oleic acid (C18: 1), linoleic acid (C18: 2), linolenic acid. (C18: 3), γ-linolenic acid (C18:
3), dihomo-γ-linolenic acid (C20: 3), arachidonic acid (C20: 4), eicosapentaenoic acid (C2
0: 5), behenic acid (C22: 0), erucic acid (C2
2: 1), docosapentaenoic acid (C22: 5), docosahexaenoic acid (C22: 6) and the like.

The alcohol constituting the fatty acid ester is
It can be any alcohol. Examples of alcohols are glycerol, methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, 2-methyl-2-propanol, 1-pentanol, 2-pentanol, 3-pentanol. , 1-hexanol, 2-hexanol, 3-hexanol, higher alcohols having 14 or more carbon atoms, propylene glycol, sorbitol and the like. The alcohol is preferably glycerol.

When the alcohol is a polyhydric alcohol,
The fatty acid ester can be an ester of one molecule of polyhydric alcohol with one or more molecules of fatty acid. For example, when the alcohol is glycerol, it can form an ester with one, two or three molecules of fatty acid as it is a trihydric alcohol. An ester with one molecule of fatty acid is called monoacylglycerol, an ester with two molecules of fatty acid is called diacylglycerol, and an ester with three molecules of fatty acid is called triacylglycerol.

The fatty acid ester is preferably oil and fat. “Fat and oil” refers to triacylglycerol. 1
In the molecule triacylglycerol, three molecules of fatty acid are bound to glycerin, but the three molecules of fatty acid may be the same or different. The fat or oil may be a pure triacylglycerol or a mixture of a plurality of different triacylglycerols. Generally, the fats and oils extracted from natural products are a mixture of different triacylglycerols.

Fatty acid esters can be extracted from natural sources. Natural sources can be plants, animals or microorganisms. The fatty acid ester can be of plant, animal or microbial origin. The animal may be selected from the group consisting of fish, birds, and mammals. The fish may preferably be selected from the group consisting of herring, sardines (such as anchovy, sardine, naked sardine, coral sardine), tuna, bonito, cod (such as cod, socodala, tigodara), saury, mackerel, mackerel and salmon. The fish is more preferably selected from the group consisting of herring, sardines (such as anchovy, sardine, bare sardine, coral sardine), tuna, bonito, cod (such as cod, socodala, tigodara) and salmon. The birds are preferably
It can be selected from the group consisting of chicken, goose, turkey, duck, and quail. The mammal may preferably be selected from the group consisting of cattle, pigs, horses and whales. The plant may preferably be selected from the group consisting of coco, oil palm, soybean, rapeseed, sesame, cotton, olive, safflower, sunflower, rice, corn, and flax.

The fatty acid ester is preferably fish oil, beef tallow, lard, chicken fat, soybean oil, coconut oil, palm oil, palm kernel oil, linseed oil, cottonseed oil, rapeseed oil, rice fat,
It may be a mixture such as corn oil, olive oil and safflower oil or a processed product thereof. In one embodiment, the fatty acid ester derived from fish is more preferable.

Fatty acid esters can also be processed, if desired, using methods known to those skilled in the art. Examples of the method for processing the fatty acid ester include transesterification, hydrogenation, and fractionation.

The fatty acid ester may be in a solid, semi-solid or liquid form at room temperature. Here, room temperature refers to about 20 to 25 ° C.

(2) Hyperbranched cyclic dextrin: The powdery fat and oil composition contains "hyperbranched cyclic dextrin" as the second component. The highly branched cyclic dextrin has an inner branched cyclic structure portion and an outer branched structure portion and has a degree of polymerization of 5
A glucan that is 0 or more. "Glucan" means D-
A polysaccharide composed of glucose. Here, the term glucan includes glucan derivatives. The term “inner branched cyclic structure portion” as used herein means α-1,
It refers to a cyclic structure portion formed by a 4-glucoside bond and an α-1,6-glucoside bond. What is the outer branch structure part?
In the specification of the present application, it refers to a non-cyclic structure portion bonded to the inner branched cyclic structure. Hyperbranched cyclic dextrins and methods of making the same are described in detail in Japanese Patent No. 3107358.

The hyperbranched cyclic dextrin contained in the powdery fat of the present invention may have at least one branch as a whole molecule.

The highly branched cyclic dextrin contained in the powdery fat and oil of the present invention may have any degree of polymerization as long as the degree of polymerization is 50 or more, but the degree of polymerization is preferably about 5.
0 to about 10,000, more preferably about 50 to about 7.0
00, most preferably about 50 to about 5,000.

The degree of polymerization in the inner branched cyclic structure present in the highly branched cyclic dextrin is preferably about 10 to about 500, more preferably about 10 to about 100.

The degree of polymerization in the hyperbranched cyclic structure present in the hyperbranched cyclic dextrin is preferably about 40 or more, more preferably about 100 or more, further preferably about 300 or more, still more preferably about 500 or more. is there.

It is sufficient that the glucan produced by the method of the present invention has at least one α-1,6-glucoside bond in the inner branched cyclic structure, and usually 1 to about 2 units.
00, preferably about 1 to about 50.

As the hyperbranched cyclic dextrin, one having one degree of polymerization may be used alone, or a mixture of various degrees of polymerization may be used. Preferably, the degree of polymerization of the highly branched cyclic dextrin is such that the ratio of the degree of polymerization of the maximum degree of polymerization to the degree of polymerization of the minimum degree of polymerization is about 100 or less, more preferably about 50 or less, and even more preferably about 10 or less. Is.

The outline of the method for producing the highly branched cyclic dextrin is described below. In the method for producing highly branched cyclic dextrin, the term raw material includes derivatized raw material. The hyperbranched cyclic dextrin reacts a saccharide having an α-1,4-glucoside bond and at least one α-1,6-glucoside bond with an enzyme capable of acting on the saccharide to form a cyclic structure. Can be manufactured by.

The enzyme which can be used for the production of the hyper-branched cyclic dextrin has a degree of polymerization of 50, acting on a saccharide having an α-1,4-glucoside bond and at least one α-1,6-glucoside bond. Any enzyme can be used as long as it is an enzyme capable of forming a glucan having a cyclic structure. Enzymes that can be used include branching enzymes (also called 1,4-α-glucan branching enzymes, branching enzymes, branching enzymes, Q enzymes), D enzymes (4
Examples include, but are not limited to, -α-glucanotransferase, disproportionation enzyme, also called amylomaltase), CGTase (also called cyclodextrin glucanotransferase), and the like.

Branching enzyme (EC 2.4.1.18)
Is a part of the α-1,4-glucan chain of starch-based sugars.
It is an enzyme that transfers to the position and forms a branch.

The enzyme D (EC 2.4.1.25) is also called the disproportionating enzyme,
It is an enzyme that catalyzes the transglycosylation reaction (heterogenization reaction) of maltooligosaccharides. The D enzyme is an enzyme that transfers a glucosyl group or a maltosyl or maltooligosyl unit from the non-reducing end of the donor molecule to the non-reducing end of the acceptor molecule. Therefore, the enzymatic reaction results in a heterogeneity in the degree of polymerization of the maltooligosaccharide initially given.

The branching enzyme exists in various plants, animals, microorganisms such as bacteria, and the origin thereof does not matter. From the point that the optimum reaction temperature is high, a branching enzyme purified from Escherichia coli in which a thermophilic bacterium-derived branching enzyme gene is cloned, or a potato-derived branching enzyme is preferable from the viewpoint that a large amount of the enzyme can be easily obtained. .

As the D enzyme, those derived from various plants or microorganisms can be used, and commercially available enzymes can also be used. The D enzyme was first discovered in potato, but it is known that it is present in various plants and microorganisms such as Escherichia coli in addition to potato. This enzyme is called D enzyme when it is derived from a plant and amylomaltase when it is derived from a microorganism. Therefore, the D enzyme may be used regardless of its origin, even if a gene encoding the plant-derived enzyme is expressed using a host such as Escherichia coli.

CGTase (EC 2.4.1.19)
As the CGTase, a well-known microorganism-derived CGTase or a commercially available CGTase can be used. CG derived from microorganism
Tase is preferably commercially available Bacillus.
CGT derived from stearothromophilus
ase (Hayashibara Institute of Biochemistry, Okayama), Bac
CGTase derived from illus macerans (trade name: Contizyme, Amano Pharmaceutical Co., Ltd., Nagoya), or Alkalophilic Bacillus
sp. CGTase from A2-5a can be used.
More preferably, Alcalophilic Bacil
lus sp. CGTase from A2-5a can be used. Alcalophilic Bacillus
sp. A2-5a is a CGTas having a high activity in the alkaline range disclosed in JP-A-7-107972.
It is a strain that produces e, and the applicant assigns a contract number (FERM P-13
864).

The above-mentioned branching enzyme, D enzyme, or CGT
ase is α-1,4- or α-1,6 in the starch molecule.
If the enzymatic activity of endo-type amylases that hydrolyze glucoside-bonds is not detected or is very weak, even crude enzymes in the purification stage can be used for the production of hyperbranched cyclic dextrins.

The enzyme used for producing the hyperbranched cyclic dextrin may be immobilized, regardless of whether it is a purified enzyme or a crude enzyme. The reaction may be carried out batchwise or continuously.
Examples of the immobilization method include carrier binding method (for example, covalent binding method, ionic binding method, or physical adsorption method), crosslinking method or entrapment method (lattice type or microcapsule type), and other methods well known to those skilled in the art. Can be used.

As a raw material used for producing the hyperbranched cyclic dextrin, a saccharide having an α-1,4-glucoside bond and at least one α-1,6-glucoside bond can be used. Examples of such saccharides include starch, partially degraded starch, amylopectin, glycogen, waxy starch, high amylose starch, soluble starch, dextrin, starch hydrolyzate, and enzymatically synthesized amylopectin by phosphorylase.

As the starch, any starch can be used as long as it is a commercially available starch. For example, underground starch such as potato starch, sweet potato starch, litter starch, tapioca starch, and above-ground starch such as corn starch, wheat starch, rice starch and the like can be used.

Examples of the partially decomposed products of starch include those obtained by partially hydrolyzing the above starch with an enzyme or an acid, and debranched products of starch.

As the amylopectin, waxy corn starch composed of 100% amylopectin can be preferably used because the glucan produced has a more uniform molecular weight distribution. For example, amylopectin having a degree of polymerization of about 600 or more can be used as a raw material.

When a branching enzyme is used, α-
Glucans having only 1,4-bonds can also be used as a raw material. Examples of the saccharides having only α-1,4-glucoside bonds include amylose, partially decomposed products of starch, starch debranched products, enzymatically synthesized amylose by phosphorylase, and maltooligosaccharides. Amylose having a degree of polymerization of about 400 or more can be preferably used.

As the raw material, the above-mentioned starch or a derivative such as a partially decomposed product of starch may be used. For example,
At least one of the alcoholic hydroxyl groups of the starch is
Glycosylated, hydroxyalkylated, alkylated, acetylated, carboxymethylated, sulfated or phosphorylated derivatives and the like can also be used. Further, a mixture of two or more of these may also be used as a raw material.

In the method for producing a highly branched cyclic dextrin, any step can be used in the step of reacting the above raw material with the enzyme as long as it is reaction conditions such as pH and temperature at which the highly branched cyclic dextrin is produced. The concentration of the raw material (substrate concentration) can also be determined in consideration of reaction conditions and the like.

When the enzyme is a branching enzyme, the pH of the reaction is usually about 3 to about 11. Reaction rate, efficiency,
From the viewpoint of the stability of the enzyme and the like, it is preferably about 4 to about 10, more preferably about 7 to about 9. The temperature is about 10 ° C to about 110 ° C, preferably about 20 ° C to about 90 ° C in terms of reaction rate, efficiency, enzyme stability, and the like. Substrate concentration is usually about 0.05% to about 6
From the viewpoint of about 0%, reaction rate, efficiency, and ease of handling the substrate solution, preferably about 0.1% to about 30%.
It is a degree. The amount of enzyme used is usually about 50 to 10,000 units per gram of substrate.

When the enzyme is D enzyme, the pH of the reaction
Is usually about 3 to about 10, preferably about 4 to about 9, and more preferably about 6 to about 8 in terms of reaction rate, reaction efficiency, enzyme stability, and the like. The temperature is
From about 10 ° C to about 90 ° C, from the viewpoint of reaction rate, reaction efficiency, enzyme stability, etc., preferably about 20 ° C to about 6 ° C.
0 ° C., more preferably about 30 ° C. to about 40 ° C. When using an enzyme obtained from a thermostable microorganism, etc., it can be used at a high temperature of about 50 ° C to about 110 ° C.
The concentration of the raw material (substrate concentration) can also be determined in consideration of reaction conditions and the like. Usually, about 0.1% to about 50%, preferably about 0.1% to about 30% from the viewpoints of reaction rate, efficiency, easy handling of substrate solution, etc. Preferably, it is about 0.1% to about 20%. The amount of the enzyme used is determined in relation to the reaction time and the concentration of the substrate, and it is usually preferable to select the amount of the enzyme so that the reaction is completed in about 1 hour to about 48 hours. Substrate 1g
Per unit is usually about 500 to about 100,000 units, preferably about 700 to about 25,000 units, more preferably about 2,000 to about 20,000 units.

When the enzyme is CGTase, the pH during the reaction is usually about 4 to about 11. Reaction rate, efficiency,
From the viewpoint of enzyme stability and the like, it is preferably about 4.5 to about 10, and more preferably about 5 to about 8. The reaction temperature is about 20 ° C to about 110 ° C, preferably about 40 ° C to about 90 ° C in view of reaction rate, efficiency, enzyme stability, and the like.
Is. The substrate concentration is usually about 0.1% to about 50%, and preferably about 0.1% to about 30% from the viewpoints of reaction rate, efficiency, handling of the substrate solution, and the like. The amount of enzyme used is usually about 1 to about 10,000 units, preferably about 1 to about 1,000 per 1 g of the substrate.
Units, more preferably about 1 to about 500 units.

The hyper-branched cyclic dextrin having various cyclic structures obtained in the above reaction is separated by a separation method well known to those skilled in the art, for example, chromatographic separation (for example, gel filtration chromatography, HPLC) membrane separation, A method such as precipitation using a solvent (eg, methanol, ethanol) can be used alone or in combination to purify.

According to the above-mentioned method, the yield of highly branched cyclic dextrin from starch as a raw material is very high, and particularly when a branching enzyme is used, it can be obtained at a yield of almost 100%.
When D enzyme or CGTase is used, glucans having only a cyclic structure are also produced.
For example, it can be easily separated from the cyclic glucan having the desired branched structure by gel filtration using Sephadex. In addition, the separated highly branched cyclic dextrin is
It can be separated according to molecular weight by gel filtration such as PLC.

The degree of polymerization of the reaction product can be measured by gel filtration from the elution position of amylose having a known degree of polymerization using a differential refractometer. Further, by using a differential refractometer and a low angle laser light scattering photometer in combination, the degree of polymerization can be determined by the following principle. The output of the differential refractometer is proportional to the concentration of glucan, and the output of the low-angle laser light scatterometer is proportional to the product of the degree of polymerization of glucan and the concentration. Therefore, by measuring the ratio of the outputs of both detectors, the degree of polymerization of glucan can be determined.

The degree of polymerization of the highly branched cyclic dextrin can be easily adjusted appropriately. For example, an exo-type amylase, for example, glucoamylase, is allowed to act on the obtained glucan to cleave the sugar chain of the outer branched structure, so that a glucan having a lower degree of polymerization can be easily obtained.

The weight of the highly branched cyclic dextrin contained in the powdery fat and oil composition of the present invention is 100% by weight of the fatty acid ester.
With respect to parts by weight, it is typically about 7 parts by weight to about 500 parts by weight, preferably about 7 parts by weight to about 300 parts by weight, more preferably about 9 parts by weight to about 150 parts by weight, and It is preferably about 10 parts by weight to about 150 parts by weight. When the weight of the highly branched cyclic dextrin is too large, the fat and oil content may be relatively reduced and the performance as a fat and oil may not be sufficiently obtained when it is used as a fat and oil. If the amount used is too small, the effect of the highly branched cyclic dextrin tends to decrease. For example, it may be difficult to obtain the effect of improving the fluidity of the powder and the solubility in water, the effect of the oxidative stability, and the effect of suppressing the fish odor during drying in the oil / fat powder manufacturing stage.

(3) Water: The powdery fat and oil composition may contain water as a third component, if necessary. Water is soft water,
Either intermediate water or hard water may be used. What is soft water?
Water having a hardness of 20 ° or more is referred to, intermediate water is water having a hardness of 10 ° or more and less than 20 °, and hard water is water having a hardness of less than 10 °. The water is preferably soft water or intermediate water,
More preferred is soft water.

The weight of water contained in the powdery fat and oil composition is arbitrary within the range where the composition exhibits fluidity.
It is preferably from about 100 parts by weight to about 300 parts by weight with respect to 100 parts by weight of the solid matter in the powdery fat and oil composition. If the weight of water is too large, a large amount of energy is required for drying the powdery liquid composition for fats and oils, and the cost may be excessive. If the amount used is too small, the powdery liquid composition for fats and oils tends to be inhomogeneous, and it may be difficult to obtain the effect of addition.

(4) Emulsifier: The powdery fat and oil composition may further contain an emulsifier as a fourth component. "emulsifier"
The term "refers to a substance that contains both a hydrophilic group and a lipophilic group in the molecule and therefore easily forms an adsorption layer at the interface between water and oil. For example, various known surfactants can be mentioned. The emulsifier is
Has an emulsifying effect. “Having an emulsifying action” means that two liquids that do not mix with each other by simply mixing (for example,
Water and an organic liquid such as oil that is immiscible with water) can be formed by adding a substance and mixing the substance to form a stable emulsion. "Emulsion"
Means a mixture in which one liquid is dispersed in the other liquid (outer phase) in the form of fine spheres (inner phase). Emulsions include cases where oil is dispersed in water (O / W emulsion) and cases where water is dispersed in oil (W / O emulsion) depending on the type of emulsifier. Emulsifiers generally contain both hydrophilic and lipophilic groups in the molecule. Hydrophilic groups are easy to adsorb to water, and lipophilic groups are easy to adsorb to oil. Therefore, the emulsifier forms an adsorption layer at the interface between water and oil. Generally, a strongly hydrophilic emulsifier (ie, a water-soluble emulsifier) is suitable for forming an O / W emulsion. Generally, to form a W / O emulsion,
Strongly lipophilic emulsifiers (ie oil-soluble emulsifiers) are suitable.

As the emulsifier, any emulsifier can be used as long as it is an emulsifier generally used in foods. Examples of the emulsifier include nonionic surfactants such as glycerin fatty acid ester, sucrose fatty acid ester, sorbitan fatty acid ester, and propylene glycol fatty acid ester; lecithin.

Examples of glycerin fatty acid ester include:
Glycerin acetic acid fatty acid ester, glycerin lactic acid fatty acid ester, glycerin carboxylic acid fatty acid ester, glycerin succinic acid fatty acid ester, glycerin acetyl tartaric acid fatty acid ester, glycerin acetic acid ester, polyglycerin fatty acid ester, polyglycerin condensed ricinoleic acid ester propylene glycol fatty acid ester, etc. To be

Examples of sorbitan fatty acid esters include:
Examples thereof include sorbitan monooleate (span 80) and sorbitan monolaurate (span 20).

Examples of the sucrose fatty acid ester include sucrose fatty acid ester containing palmitic acid or stearic acid as a fatty acid.

Examples of lecithin include soybean lecithin and egg yolk lecithin. The lecithin may be enzymatically degraded lecithin.

The emulsifiers may be used alone or in combination of two or more.

The weight of the emulsifier contained in the powdery fat and oil composition of the present invention may be within the range which achieves the purpose of emulsion formation and is preferable in terms of taste.
It is typically about 0.001 to about 50 parts by weight, preferably about 0.01 to about 1 part by weight, relative to 0 parts by weight.
0 parts by weight, more preferably about 0.1 parts by weight to about 5 parts by weight.
Parts by weight. If the weight of the emulsifier is too large, the taste of the emulsifier tends to be strong and the taste tends to deteriorate, and the emulsifying function may deteriorate depending on the type of the emulsifier. If the amount used is too small, the emulsification in the powdery fat may easily become inhomogeneous.

(5) Excipient: The powdery fat and oil composition may contain an excipient. The “excipient” is a general term for substances that normally coat the outside of the fat or oil that is the core substance when producing a powdery fat or oil. Excipients are any substances that do not substantially impair the effects of the addition of hyperbranched cyclic dextrin and do not adversely affect fats and oils. Examples of excipients include
Examples thereof include casein and its salts (for example, casein soda), gelatin, proteins such as whey protein and egg white; oligosaccharides such as sucrose, lactose and glucose; sugar alcohols such as sorbitol and mannitol; starch and its decomposition products. The excipient is preferably casein soda, gelatin, whey protein, egg white, sucrose, lactose, starch or a decomposition product thereof. The powdery fat and oil of the present invention may contain one kind or a plurality of kinds of these excipients.

The weight of the excipient contained in the powdery fat and oil composition of the present invention is 100 parts by weight of the fatty acid ester.
It is typically about 5 parts by weight to about 500 parts by weight, preferably about 10 parts by weight to about 300 parts by weight, more preferably about 20 parts by weight to about 150 parts by weight. If the weight of the excipient is too high, the concentration of fat will be relatively low,
In some cases, it may be difficult to obtain a preferable quality as a powdered fat and oil as a fat and oil feedstock. If the amount used is too small, oil bleeding may occur and it may be difficult to obtain the effect of addition.

(6) Other components: The powdery fat and oil may optionally contain other additives or food materials as long as the performance of the fat and oil and the effect of the addition of the highly branched cyclic dextrin are not substantially impaired. it can. Other additives or food materials include antioxidants (for example, tocopherol), flavors, colorants, flavors (salt, sweetener, sodium citrate, etc.), minerals, vitamins used in general food production. , PH adjusters, grain powders (eg, sweet corn powder), and the like.

<Production of Powdered Oils and Fats> The powdered oils and fats of the present invention can be obtained by any method from the composition for powdered oils and fats.
For example, it is produced by mixing a fatty acid ester, a highly branched cyclic dextrin and water to obtain a powdery liquid composition for fats and oils, and then drying this liquid composition.

In this method, specifically, first, a fatty acid ester, a highly branched cyclic dextrin and water, and optionally other components such as an emulsifier are mixed by a pastelizer, a cake mixer, a horizontal mixer or the like to obtain a powder form. A liquid composition for oils and fats is obtained. As a mixing method, the mixing time and the mixing method are not particularly limited as long as the obtained powdery liquid composition for fats and oils is uniformly mixed. For example, water may be added and mixed after mixing the oily raw material and the aqueous raw material. However, after the oily raw materials (eg, fatty acid ester, emulsifier, and antioxidant) and the aqueous raw materials (eg, highly branched cyclic dextrin, excipient and water) are mixed separately in advance, the oily raw materials and the aqueous materials are mixed. It is preferable to mix the raw materials.

Next, the powdery liquid composition for fats and oils is emulsified using a homogenizer or the like. The emulsion type is an oil-in-water type emulsion. The particle size may be large or small as long as an emulsified state is obtained. The dispersed particle size is preferably 20 microns or less, more preferably 10 microns or less. The model used in the emulsification is not particularly limited as long as it can emulsify. For example, a homogenizer, a homomixer, a mycoloider, etc. can be used.

Next, the emulsified liquid composition for powdered fats and oils is dried to obtain powdered fats and oils. The drying method is preferably a drying method in which the emulsified state is maintained until just before the completion of drying. Further, it is also preferable from the viewpoint of industrial production that the drying method is capable of treating a large amount of the powdery liquid composition for fats and oils. Examples of such a drying method include spray drying (also referred to as spray drying) and freeze drying. Preferably, the drying is done by spray drying.

The fatty acid ester in the powdery fat or oil thus obtained is usually surface-treated with a highly branched cyclic dextrin. "Surface treatment" means, between the fatty acid ester and the highly branched cyclic dextrin, the fluidity, the dispersibility in water, as compared with the case of the fatty acid ester dried alone.
It means that the hyperbranched cyclic dextrin has some action on the surface of the fatty acid ester to the extent that an interaction is obtained to the extent that either improvement in oxidative stability or flavor retention is obtained. The surface of the fatty acid ester is probably presumed to be covered with the hyperbranched cyclic dextrin. However, as long as the effect of adding the hyperbranched cyclic dextrin can be obtained, whether the hyperbranched cyclic dextrin actually adheres to the fatty acid ester or not. Does not matter.

The obtained powdery fat or oil contains fatty acid ester, preferably about 10% by weight, based on the weight of the powdery fat or oil.
-80% by weight, more preferably about 20% -75% by weight, even more preferably 30% -75% by weight.

The obtained powdery fat and oil has a highly branched cyclic dextrin, preferably about 1 to the weight of the powdery fat and oil.
Wt% to 90 wt%, more preferably 2.5 wt% to 8
0 wt%, even more preferably 5 wt% to 70 wt%
contains.

The obtained powdery fat and oil contains an emulsifier, preferably 0.01% by weight to 10% by weight, based on the weight of the powdery fat and oil.
Wt%, more preferably 0.1 wt% to 5 wt%, even more preferably 0.5 wt% to 1.5 wt%.

<Production of Foods and Beverages Containing Powdered Oils and Fats> By adding the powdered oils and fats of the present invention to various foods or feeds or feeds, or by adding other foods or feeds or feeds during the production of powdered oils or fats. By adding
Foods and drinks containing fats and oils are provided.

Examples of the above foods and drinks include dietary supplements, health foods, functional foods, foods for the elderly, and the like. In the present specification, the food and drink is a generic term for solids, fluids and liquids, and mixtures thereof, which are edible.

The dietary supplement refers to a food in which a specific nutritional component is fortified. Healthy food refers to food that is considered to be healthy or healthy, and includes dietary supplements, natural foods, diet foods, and the like. The functional food is a food for supplementing nutritional components that fulfill the body's regulation function, and is synonymous with food for specified health uses. What is food for the elderly?
Foods that have been treated so that they are easier to digest and absorb than untreated foods.

Examples of the forms of these foods and drinks include meat,
Natural foods such as fish and nuts (treated with fats and oils); Foods to which fats and oils are added during cooking such as Chinese food, ramen and soups; Tempura, fried foods, fried rice, donuts, sugars, etc. using oils and fats as heat medium Foods: Coffee cream powder, cream soup powder, butter, margarine, mayonnaise, dressing, chocolate, instant noodles, caramel, biscuits, cookies, cakes, ice cream, etc. Examples thereof include foods in which oils and fats are sprayed or applied during processing and finishing of biscuits, bean jam, and the like. However, the food of the present invention is not limited to foods originally containing fats and oils, for example, bread, noodles, rice, confectionery (candy, chewing gum, gummy, tablet confectionery, Japanese confectionery), tofu and its processing. Agricultural food such as products; fermented food such as sake, medicinal liquor, mirin, vinegar, soy sauce and miso; livestock food such as yogurt, ham, bacon and sausage;
It may be a marine product such as kamaboko, fried tempura, and rice paste; fruit juice drink, infant formula, soft drink, sports drink, alcoholic drink, tea and other drinks.

The food and drink of the present invention can also be in the form of pharmaceutical preparations,
Or protein (As a protein source, proteins such as milk protein with high amino acid balance and high nutritional value, soybean protein, egg albumin, etc. are most widely used, but their degradation products, egg white oligopeptides, soybean hydrolysates , A mixture of various amino acids may be used), sugars, fats, trace elements, vitamins, emulsifiers, natural liquid foods in which the fats and oils of the present invention are mixed with flavors, semi-digestive nutrition foods and component nutrition foods, drinks It may be in a processed form such as an agent or enteral nutrition. When the food or drink of the present invention is in the form of a pharmaceutical preparation, the food or drink of the present invention includes powders, granules, tablets, capsules, troches, internal liquids, suspensions,
It may be in the form of an emulsion, a syrup, a drink, a natural liquid diet, a semi-digestive diet, a component diet, an enteral diet, and the like.

For example, when the powdery fat and oil of the present invention is produced by using a fat and oil containing a large amount of highly unsaturated fatty acid ester such as fish oil, it is particularly useful for health foods and the like.

These foods and drinks can be produced by a known method. The powdery fat and oil of the present invention is added at any stage as long as it does not substantially modify or decompose the fatty acid ester. The amount of the powdered fat and oil added is not particularly limited,
The target fatty acid ester is appropriately set so as to have a desired content.

[0106]

The present invention will be described in more detail with reference to the following examples. The present invention is not limited to the following examples.

<Production Example 1: Preparation of highly branched cyclic dextrin> Takata, H .; Et al., Carbohydr. Re
s. , 295 (1996) 91-101 by scaling up the method to synthesize a hyperbranched cyclic dextrin. Specifically, first, 20 kg of waxy cornstarch (average polymerization degree of 30,000 or more)
60 liters of 5 mM sodium phosphate buffer (pH
It was suspended in 7.5) and gelatinized by heating in a 100 ° C. water bath with sufficient stirring. After cooling to about 50 ° C., it was confirmed that the pH was around 7. Then, after adding 8,000,000 units of branching enzyme, the reaction product was obtained by stirring at 50 ° C. for 18 hours while maintaining the temperature. Then, the reaction product was deionized and then dried by a spray drier to obtain a white powder of highly branched cyclic dextrin. The weight average molecular weight of the inner branched cyclic structure portion of the obtained highly branched cyclic dextrin was 50, and the weight average polymerization degree of the whole molecule was 1,
It was 800.

<Examples 1 to 4: Preparation of powdery fats and oils> Table 1
The raw materials shown in the column of oil phase part were mixed at the compounding ratio (parts by weight) shown in the same column to prepare an oil phase part. The raw materials in the column of the water phase portion shown in Table 1 were dissolved in 200 parts by weight of warm water at 50 ° C. in the mixing ratio shown in the same column to prepare the water phase portion.

Next, the oil phase part and the water phase part were mixed and preliminarily emulsified, and further homogenized using a homogenizer (manufactured by Izumi Food Machinery Co., Ltd.) at 150 kg / cm ² to obtain an emulsion. Obtained. This emulsion was spray-dried using a spray dryer (manufactured by Okawara Koki Co., Ltd.) at a temperature of 150 ° C. to obtain a powdery fat and oil. It is presumed that the powdery fat and oil has a coating film of the excipient and the highly branched cyclic dextrin formed on the surface.

[0110]

[Table 1] In order to investigate the solubility (or dispersibility) of the obtained powdery fats and oils, the following dissolution tests were conducted at three water temperatures. First, distilled water at 70 ℃, 25 ℃, or 5 ℃ is 200m each.
Each was placed in a 500 ml beaker. Then, each beaker was charged with 4 g of either powdered oil or fat. This mixture was stirred for 3 minutes at a rotation speed of 400 rpm by a table top agitator equipped with a propeller blade. After this, the dissolved (decomposed) state was visually examined. The dissolution state was evaluated according to the following four stages: all dissolved within 1 minute (marked with ⊚), all dissolved within 1 to 5 minutes (marked with ○), slightly dissolved (marked with △), and not dissolved (x). mark). The results are shown in Table 1.

As is clear from the results shown in Table 1, when 10 to 150 parts by weight of the highly branched cyclic dextrin was blended (Examples 1 to 4), the coating film was easily dissolved in water at a wide temperature of 5 to 70 ° C. And showed excellent dispersibility. The powdery fat and oil obtained was a powder having a smooth feel and excellent fluidity. It was confirmed that the fluidity was improved even when 5 parts of the highly branched cyclic dextrin was blended (Example 5).

Comparative Example 1 The powdery fat and oil of Comparative Example 1 was prepared in the same manner as in Example 1 except that dextrin having a DE value of 3 was used in place of the hyperbranched cyclic dextrin (Comparative Example 1 in Table 1). Obtained.

The powdery fats and oils obtained were evaluated in the same manner as the powdery fats and oils of Examples 1 to 5. The results are shown in Table 1. The powdery fat and oil of Comparative Example 1 had poor solubility as the water temperature became lower, and did not satisfy the expected effect.

<Examples 6 to 9> Refined fish oil was used in place of soybean white squeezing oil, and highly branched cyclic dextrin was added to 10,150.
Or Example 1 except that 100 parts by weight (Table 2) was used.
A powdery fat and oil was obtained in the same manner as in. The refined fish oil used contained 6 mol% of EPA and 17 mol% of DHA in all fatty acids (Ueda Oil Co., Ltd .; trade name: DHA oil).

[0115]

[Table 2] In order to examine the preservability of the obtained powdery fat and oil, the peroxide value (POV: meq / Kg) when the powdery fat and oil was incubated at 30 ° C. for 30 days was measured on the 0th day according to the usual method (standard fat and oil analysis test method). From every 10 days. The results are shown in Table 3.
And shown in FIG.

As is clear from the results of Table 3, Example 6
The peroxide values of the powdered fats and oils of ~ 8 were suppressed to about 3 times the POV at the start of the test after 30 days, and hardly increased. In Examples 6 to 8, the rate of oxidative deterioration was extremely slow, and as shown in Table 3, it was found that the flavor was maintained well. It was also confirmed in Example 9 that the oxidation could be considerably suppressed.

[0117]

[Table 3] The odor of the obtained powdery fat and oil was examined by sensory evaluation. By smelling the obtained powdery fat and oil,
Evaluation was made on the following three scales: no fish odor and rancid odor (⊚), almost no fish odor and rancid odor (∘), and severe fish odor and rancid odor (x). The results are shown in Table 4.
Shown in.

[0118]

[Table 4] As can be seen from the results in Table 4, the powdery fats and oils obtained by blending the hyper-branched cyclic dextrin hardly generate fishy odor and rancid odor, and have a low blending amount (also in Example 1, The generation of acid rancidity was suppressed.

<Comparative Examples 2 and 3> A dextrin having a DE value of 3 was used in place of the hyperbranched cyclic dextrin (Table 2).
Powdered oils and fats of Comparative Examples 3 and 4 were obtained in the same manner as in Examples 5 and 6 except for Comparative Examples 3 and 4).

The powdery fats and oils obtained were evaluated in the same manner as the powdery fats and oils of Examples 6 to 9. The results are shown in Tables 3 and 4.

As is clear from the results of Table 3, Comparative Example 2
The peroxide value of the powdered fats and oils of Nos. 3 and 3 increased to 50 times the POV at the start of the test at 20 days.

The POVs of Comparative Examples 2 and 3 at the 10th day and 20th day were about 1 as compared with the POV of the same day on the same day.
It was a high value of 5 to 30 times, and it was confirmed that the oxidation was significantly advanced. This result was in good agreement with the result of sensory evaluation.

As can be seen from the results in Table 4, the powdered fats and oils obtained without using the highly branched cyclic dextrin had a content of 30
When stored at ℃, fishy odor was generated very rapidly, and the rancid odor became stronger with each storage.

<Example 10: Preparation of dietary supplement> Table 5
The oil phase part was prepared by mixing the raw materials shown in the oil phase part column at the mixing ratio (parts by weight) shown in the same column, and the raw materials shown in the water phase part column in Table 5 are shown in the same column. A dietary supplement was obtained in the same manner as in Example 1 except that the aqueous phase portion was prepared by dissolving in 200 parts by weight of warm water of 65 ° C. at a mixing ratio.

[0125]

[Table 5] The resulting dietary supplement was a powder with a smooth feel and excellent fluidity. 5g of the obtained dietary supplement
Was diluted with 40 cc of hot water at 30 ° C. by a conventional method, and as a result, this milk powder was easily dissolved in water and showed excellent dispersibility.

<Example 11: Preparation of dietary supplement> Table 6
The oil phase part was prepared by mixing the raw materials shown in the oil phase part column at the mixing ratio (parts by weight) shown in the same column, and the raw materials shown in the water phase part column in Table 6 were shown in the same column. A dietary supplement was obtained in the same manner as in Example 1 except that the aqueous phase portion was prepared by dissolving in 200 parts by weight of warm water of 65 ° C. at a mixing ratio.

[0127]

[Table 6] The resulting dietary supplement was a powder with a smooth feel and excellent fluidity.

The obtained dietary supplement is treated at 30 ° C. for 30 days.
Incubated in an open system. As a result of diluting 5 g of the dietary supplement after incubation with 40 cc of hot water at 30 ° C. by a conventional method, this dietary supplement easily dissolved in water and showed excellent dispersibility. As a result of eating the dietary supplement dissolved in water, there was no fishy smell and it was easy to drink. From this,
It was shown that the dietary supplement obtained by using the highly branched cyclic dextrin has good oxidative stability and high storage stability.

<Example 12: Preparation of coffee cream powder> The oil phase part was prepared by mixing the raw materials shown in the oil phase part column of Table 7 in the compounding ratio (parts by weight) shown in the same column. 7
The raw materials in the column of the water phase part shown in 6 are mixed at the mixing ratio shown in the column.
A coffee cream powder was obtained in the same manner as in Example 1, except that the aqueous phase was prepared by dissolving it in 200 parts by weight of warm water at 5 ° C.

[0130]

[Table 7] The coffee cream powder obtained was a powder having a smooth feel and extremely good fluidity. As a result of adding 15 g of the obtained coffee cream powder to 180 g of coffee, this coffee cream powder was easily dissolved in coffee and exhibited excellent dispersibility.

<Example 13> The oil phase part was prepared by mixing the raw materials shown in the oil phase part column of Table 8 in the compounding ratio (parts by weight) shown in the same column, and the water phase part shown in Table 8 was prepared. Coffee cream powder was obtained in the same manner as in Example 1 except that the raw materials in the column were dissolved in 200 parts by weight of warm water at 65 ° C. in the mixing ratio shown in the column to prepare the aqueous phase part.

[0132]

[Table 8] The coffee cream powder obtained was a powder having a smooth feel and extremely good fluidity.

30 parts of the obtained coffee cream powder
Incubated for 30 days in an open system at 30 ° C. As a result of adding 15 g of the coffee cream powder after incubation to 180 g of coffee, this coffee cream powder was easily dissolved in coffee and exhibited excellent dispersibility.
As a result of drinking coffee to which coffee cream powder was added, there was no fishy smell and it was easy to drink. From this, it was shown that the coffee cream powder obtained by using the highly branched cyclic dextrin has good oxidation stability and high storage stability.

<Example 14: Preparation of corn soup powder> The raw materials shown in the column of oil phase portion in Table 9 were mixed at the compounding ratio (parts by weight) shown in the same column to prepare an oil phase portion, and The raw materials in the column of the water phase portion shown in 9 are mixed at the mixing ratio shown in the column at 65 ° C.
A corn soup powder was obtained by the same method as in Example 1 except that 200 parts by weight of warm water was prepared to prepare an aqueous phase part.

[0135]

[Table 9] The resulting corn soup powder was a powder having a smooth feel and extremely good fluidity. 20 g of the obtained corn soup powder was heated according to a conventional method at 120 cc in hot water at 50 ° C.
As a result of diluting with, the corn soup powder easily dissolved in hot water and showed excellent dispersibility.

<Example 15: Preparation of corn soup powder> Raw materials shown in the column of oil phase portion of Table 10 were mixed in the compounding ratio (parts by weight) shown in the same column to prepare an oil phase portion, 10
The raw materials in the column of the water phase part shown in 6 are mixed at the mixing ratio shown in the column.
A corn soup powder was obtained in the same manner as in Example 1 except that the water phase portion was prepared by dissolving in 200 parts by weight of warm water at 5 ° C.

[0137]

[Table 10] The resulting corn soup powder was a powder having a smooth feel and extremely good fluidity.

The resulting corn soup powder was incubated for 30 days in an open system at 30 ° C. 20 g of corn soup powder after incubation was added to 50
As a result of diluting with 120 cc of hot water at 0 ° C., this corn soup powder was easily dissolved in hot water and showed excellent dispersibility. As a result of eating corn soup powder dissolved in hot water, there was no fishy smell and it was easy to drink. From this, it was shown that the corn soup powder obtained by using the highly branched cyclic dextrin has good oxidation stability and high storage stability.

[0139]

INDUSTRIAL APPLICABILITY According to the present invention, a powdery fat or oil containing a fatty acid ester and a highly branched cyclic dextrin can be produced. According to the present invention, the obtained powdery fat and oil has good fluidity and is easy to handle, and has excellent dispersibility in water in a wide temperature range from low temperature to high temperature.

According to the present invention, the generation of peroxide due to the heat history of the obtained powdery fat and oil is suppressed, and the antioxidant function works even in the storage state, and the powder is excellent in the stability of oxidation and the maintenance of flavor. It becomes a fat and oil. Therefore, even when an oil or fat containing a large amount of highly unsaturated fatty acid is used as the fatty acid ester, a powdery oil or fat with less generation of peroxide and excellent in oxidative stability and flavor maintenance can be obtained.

The powdery fat and oil obtained according to the present invention can be suitably used for various foods and drinks, cosmetics, pharmaceuticals and the like.

[Brief description of drawings]

FIG. 1 is a graph showing the antioxidant properties of powdered fats and oils using highly branched cyclic dextrin.

Continuation of front page (51) Int.Cl. ⁷ identification code FI theme code (reference) C11C 3/00 A23D 9/00 518 516 (72) Inventor Koichi Inoue Koichi 2-2F Tennoji Kokubuncho, Osaka Reference) 4B001 AC03 AC05 AC15 AC40 BC04 EC09 4B018 LE03 MD11 MD12 MD13 MD17 MD27 ME13 MF06 4B026 DC04 DL03 DX08 4B036 LC03 LE01 LF01 LH11 LH13 LP09 4H059 BA17 BA30 BA33 BB05 BB45 BC16 BC13 BC45 BB45 BC13 BC45 BC13

Claims (11)

[Claims] 1. A powdery fat or oil containing a fatty acid ester and a highly branched cyclic dextrin, wherein the fatty acid constituting the fatty acid ester contains a highly unsaturated fatty acid.
Fats and oils. 2. The polyunsaturated fatty acid comprises 3 in one molecule.
The fat or oil according to claim 1, which comprises one or more double bonds. 3. The oil or fat according to claim 1, wherein the polyunsaturated fatty acid is a long chain fatty acid. 4. The polyunsaturated fatty acid is dihomo-γ-
The oil or fat according to claim 3, which is selected from the group consisting of linolenic acid, eicosapentaenoic acid, docosapentaenoic acid and arachidonic acid. 5. The oil or fat according to claim 1, which further contains an emulsifier. 6. The oil or fat according to claim 1, further comprising an excipient. 7. A method for producing a powdery fat or oil, which comprises a step of mixing a fatty acid ester, a hyperbranched cyclic dextrin and water to obtain a liquid composition for a powdery fat and oil, and a step of drying the liquid composition. And the fatty acids constituting the fatty acid ester include polyunsaturated fatty acids. . 8. The method according to claim 7, wherein the powdery fat and oil liquid composition further contains an emulsifier. 9. The method of claim 7, wherein the drying step is performed by spray drying. 10. A powdery composition for fats and oils containing a fatty acid ester and a highly branched cyclic dextrin, wherein the fatty acid constituting the fatty acid ester contains a highly unsaturated fatty acid. 11. A food or drink containing the oil or fat according to any one of claims 1 to 6.