L-ascorbic acid fatty acid ester preparation and production method thereof

Abstract

To provide an L-ascorbic acid fatty acid ester preparation which is a preparation containing L-ascorbic acid fatty acid ester, has desirable stability while being produced and kept for a long time, and is highly effective, when added to a beverage / food product, in curbing flavor deterioration and / or preventing oxidation and further in preventing or curbing color deterioration, or in preventing or curbing color change.SOLUTION: An L-ascorbic acid fatty acid ester preparation is obtained by: adding L-ascorbic acid fatty acid ester, a powdering base material, organic acid salt, and vitamin E to water and emulsifying the components; preparing a water-in-oil emulsified composition of pH 5.0-8.0; and dehydration processing the obtained water-in-oil emulsified composition.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to an L-ascorbic acid fatty acid ester preparation and a method for producing the same. [Background technology]

[0002] L-ascorbic acid fatty acid esters are formed by esterifying L-ascorbic acid with a fatty acid. They have vitamin C activity and antioxidant properties, and because they are lipophilic, they are used as nutritional enhancers and antioxidants for foods that contain edible oils and fats.

[0003] However, although L-ascorbic acid fatty acid esters are oil-soluble, they are difficult to handle because they have low solubility in fats and oils and have a melting point of 110° C. or higher. In addition, because they have poor dispersibility in water (water dispersibility), even if they are used in aqueous foods such as milk drinks and soft drinks, the crystals of the L-ascorbic acid fatty acid esters will not disperse but will float in the food.

[0004] In addition, in the production of foods such as noodles, cookies, and biscuits, water is added to wheat flour and kneaded to produce dough, so water is present in the dough, and therefore, in the production of foods such as noodles, cookies, and biscuits, it is difficult to uniformly disperse crystals of L-ascorbic acid fatty acid esters in the dough, as in the case of aqueous foods such as milk drinks and soft drinks.

[0005] Therefore, the following techniques have been used: Patent Document 1 discloses a water-dispersible ascorbic acid fatty acid ester composition comprising an ascorbic acid fatty acid ester, a hydrophilic surfactant, and an oligosaccharide. Patent Document 2 discloses an antioxidant preparation characterized in that an L-ascorbic acid fatty acid ester is uniformly dispersed in an oily substance. Patent Document 3 discloses a hydrophilic inclusion complex formed by including a higher fatty acid ester of L-ascorbic acid in cyclodextrin. Patent Document 4 discloses a particulate powder obtained by heating and melting an L-ascorbic acid fatty acid ester and a hardened oil or fat to 100° C. or higher, and then recovering the powder by spray cooling.

[0006] In the methods disclosed in Patent Documents 1 to 4, when dispersed in water, the L-ascorbic acid fatty acid ester has low affinity to water and floats in the aqueous dispersion. In such a dispersed state, the L-ascorbic acid fatty acid ester precipitates or sediments during storage of the aqueous food in which the L-ascorbic acid fatty acid ester is dispersed, making it difficult to uniformly blend the L-ascorbic acid fatty acid ester in the food, and therefore a sufficient antioxidant effect cannot be obtained. Furthermore, in Patent Document 4, the L-ascorbic acid fatty acid ester is heated at high temperatures during production, which causes the L-ascorbic acid fatty acid ester to decompose, resulting in a problem of a decrease in the content.

[0007] In relation to improving the dispersibility of L-ascorbic acid fatty acid esters in foods and beverages, Patent Document 5 discloses a method for producing a powdered L-ascorbic acid fatty acid ester preparation, which comprises adding an L-ascorbic acid fatty acid ester, a powdered base material, and an oil-soluble substance to water to emulsify the mixture, and then drying the resulting oil-in-water emulsion composition. [Prior art documents] [Patent documents]

[0008] [Patent Document 1] Japanese Patent Application Publication No. 7-115951 [Patent Document 2] Japanese Patent Application Publication No. 9-208986 [Patent Document 3] Japanese Patent Application Publication No. 10-231244 [Patent Document 4] International Publication No. 2016 / 136285 [Patent Document 5] JP 2014-155453 A Summary of the Invention [Problem to be solved by the invention]

[0009] However, the method disclosed in Patent Document 5 has excellent dispersibility of L-ascorbic acid fatty acid ester in food and drink, but the stability of the L-ascorbic acid fatty acid ester preparation is poor. In addition, when L-ascorbic acid fatty acid ester is brought into contact with water, hydrolysis is likely to proceed, and even if a high amount of L-ascorbic acid fatty acid ester is added, the content of L-ascorbic acid fatty acid ester decreases, and there is a problem of flavor deterioration due to decomposition.

[0010] As described above, various techniques have been used to solve the problem of aqueous dispersion preparations of L-ascorbic acid fatty acid esters, but no L-ascorbic acid fatty acid ester preparations with high L-ascorbic acid fatty acid ester content and good stability with little loss of content have been obtained, so that sufficient antioxidant effect cannot be obtained even when added to food and beverages. Therefore, there is a demand for L-ascorbic acid fatty acid ester preparations that are excellent in antioxidant effect, flavor deterioration suppression effect, and color fading prevention or suppression effect and color discoloration prevention or suppression effect, as well as excellent storage stability.

[0011] Therefore, the present invention aims to provide an L-ascorbic acid fatty acid ester preparation which has little reduction in the content of L-ascorbic acid fatty acid ester, i.e., has good stability during production and long-term storage, and which has high antioxidant effects and flavor deterioration inhibition effects, as well as high anti- and anti-fading effects and anti- and anti-discoloration effects when added to foods and beverages, and a method for producing the same. [Means for solving the problem]

[0012] As a result of intensive research into the above-mentioned problems, the present inventors have found that the above-mentioned problems can be solved by an L-ascorbic acid fatty acid ester preparation obtained by adding an L-ascorbic acid fatty acid ester, a powdered base material, an organic acid, and vitamin E to water and emulsifying the mixture to prepare an oil-in-water emulsion composition, adjusting the pH of the oil-in-water emulsion composition to a specific range, and drying the resulting oil-in-water emulsion composition, thereby completing the present invention.

[0013] That is, the present invention (1) provides an L-ascorbic acid fatty acid ester preparation, which is characterized by being obtained by adding an L-ascorbic acid fatty acid ester, a powdered base material, an organic acid salt, and vitamin E to water and emulsifying the mixture to obtain an oil-in-water emulsion composition having a pH of 5.0 to 8.0, and then drying the obtained oil-in-water emulsion composition.

[0014] The present invention (2) also provides an L-ascorbic acid fatty acid ester preparation according to (1), characterized in that the organic acid salt is at least one selected from the group consisting of sodium salts, potassium salts, and calcium salts of citric acid, malic acid, tartaric acid, gluconic acid, succinic acid, acetic acid, lactic acid, and ascorbic acid.

[0015] The present invention (3) also provides an L-ascorbic acid fatty acid ester preparation according to (1), which contains a non-reducing sugar.

[0016] The present invention (4) also provides an L-ascorbic acid fatty acid ester preparation according to any one of (1) to (3), which is characterized by at least one of the following: prevention of oxidation of food or beverage, inhibition of flavor deterioration, prevention or inhibition of fading, and prevention or inhibition of discoloration.

[0017] The present invention (5) also provides an emulsification step of adding at least an L-ascorbic acid fatty acid ester, a powdered base material, an organic acid salt, and vitamin E to water and emulsifying the mixture to prepare an oil-in-water emulsion composition having a pH of 5.0 to 8.0; a drying step of drying the obtained oil-in-water emulsion composition; The present invention provides a method for producing an L-ascorbic acid fatty acid ester preparation, which is characterized by having the following formula: Effect of the Invention

[0018] According to the present invention, it is possible to provide an L-ascorbic acid fatty acid ester preparation which exhibits little decrease in the content of L-ascorbic acid fatty acid ester and has good stability during production and long-term storage, and it is also possible to provide an L-ascorbic acid fatty acid ester preparation and a production method thereof which, when added to food and beverages, has high antioxidant effects and flavor deterioration suppression effects, as well as high anti- or suppression effects for fading and discoloration. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0019] The L-ascorbic acid fatty acid ester preparation of the present invention is characterized in that it is obtained by adding an L-ascorbic acid fatty acid ester, a powdered base material, an organic acid salt, and vitamin E to water to emulsify the mixture, thereby obtaining an oil-in-water emulsion composition having a pH of 5.0 to 8.0, and then drying the obtained oil-in-water emulsion composition. When added to food or drink, the L-ascorbic acid fatty acid ester preparation of the present invention can prevent or inhibit oxidation and / or flavor deterioration, as well as fading and discoloration of the food or drink.

[0020] The L-ascorbic acid fatty acid ester preparation of the present invention contains L-ascorbic acid fatty acid ester. L-ascorbic acid fatty acid ester is a compound obtained by esterification reaction between L-ascorbic acid and fatty acid, in other words, a compound in which the reaction residue of esterification reaction between L-ascorbic acid and fatty acid is bonded by ester bond. L-ascorbic acid fatty acid ester is not particularly limited as long as it can be used as a food additive, and examples thereof include L-ascorbic acid palmitate, L-ascorbic acid stearate, etc. Among these, L-ascorbic acid fatty acid ester is preferably L-ascorbic acid palmitate because it has a relatively low melting point and a small molecular weight, resulting in high vitamin C activity.

[0021] The L-ascorbic acid fatty acid ester preparation of the present invention contains a powdered base material. The powdered base material can be powdered by coating the ingredients, and is not particularly limited as long as it is used in food, and examples thereof include sugars, thickening polysaccharides or gums, starches, etc. Examples of sugars include glucose, fructose, maltose, sucrose, dextrin, cyclodextrin, corn syrup, etc. Examples of thickening polysaccharides or gums include xanthan gum, locust bean gum, tragacanth gum, gum arabic, pectin, etc. Examples of starches include natural starches such as potato starch, corn starch, waxy corn starch, sweet potato starch, wheat starch, rice starch, tapioca starch, etc., or processed starches thereof (acid-decomposed starch, pregelatinized starch, etc.), and alkenylsuccinic acid ester starch obtained by reacting natural starch and / or processed starch with alkenylsuccinic anhydride in the presence of an alkali catalyst.

[0022] The L-ascorbic acid fatty acid ester preparation of the present invention contains an organic acid salt. The organic acid salt is not particularly limited as long as it is a salt of an organic acid used in food and can provide an oil-in-water emulsion composition having a pH of 5.0 to 8.0, preferably 5.0 to 7.5. The organic acid salt may be at least one selected from the group consisting of sodium salts, potassium salts, and calcium salts of citric acid, malic acid, tartaric acid, gluconic acid, succinic acid, acetic acid, lactic acid, and ascorbic acid. Examples of the organic acid salt include trisodium citrate, sodium malate, sodium tartrate, sodium gluconate, sodium succinate, sodium acetate, sodium lactate, and sodium ascorbate. In the L-ascorbic acid fatty acid ester formulation of the present invention, when an oil-in-water emulsion composition is prepared using an L-ascorbic acid fatty acid ester, a powdered base material, and vitamin E, an organic salt is added to water to adjust the pH of the oil-in-water emulsion composition to 5.0 to 8.0, preferably 5.0 to 7.5, and the stability of the L-ascorbic acid fatty acid ester formulation of the present invention during production and long-term storage can be increased. On the other hand, when an organic acid salt is not used, the synergistic effect of the organic acid salt is not obtained, so the stability of the L-ascorbic acid fatty acid ester formulation during production and long-term storage cannot be increased, and when an organic acid is used instead of an organic acid salt, the pH of the oil-in-water emulsion composition is likely to be less than 5.0, so the stability of the L-ascorbic acid fatty acid ester formulation during production and long-term storage cannot be increased.

[0023] The L-ascorbic acid fatty acid ester preparation of the present invention contains vitamin E. Examples of vitamin E include d-α-tocopherol, d-β-tocopherol, d-γ-tocopherol, d-δ-tocopherol, dl-α-tocopherol, and mixed tocopherols, and any vitamin E may be used. A mixture of these may also be used. The L-ascorbic acid fatty acid ester preparation of the present invention contains the above vitamin E for the purpose of preventing oxidation and / or suppressing flavor deterioration, and preventing or suppressing discoloration and discoloration, and may also contain the above vitamin E for nutritional enhancement. By containing vitamin E in the L-ascorbic acid fatty acid ester preparation of the present invention, the stability of the L-ascorbic acid fatty acid ester preparation of the present invention during production and long-term storage is increased.

[0024] There are no particular limitations on the mixed tocopherols, so long as they are tocopherols recovered from deodorized distillates (e.g., deodorized scum, deodorized sludge, or hot well oil) produced as a by-product in the process of refining vegetable oils. Examples of mixed tocopherols include mixtures containing α-, β-, γ-, and δ-tocopherols and α-, β-, γ-, and δ-tocotrienols, which are homologues of tocopherol, obtained by separating and refining deodorized distillates of canola oil, sesame oil, rice oil, safflower oil, soybean oil, corn oil, rapeseed oil, palm oil, sunflower oil, cottonseed oil, peanut oil, etc.

[0025] Some commercially available vitamin E products contain oil-soluble substances (oils and fats, fat-soluble vitamins other than vitamin E, etc.), but in the present invention, such forms of vitamin E can also be used without any problems.

[0026] Examples of vitamin E that are commercially produced and sold include Emix D (d-δ-tocopherol; manufactured by Mitsubishi Chemical Corporation), Riken E Oil (registered trademark) Super 60 (mixed tocopherols; manufactured by Riken Vitamin Co., Ltd.), Riken E Oil (registered trademark) 600 (mixed tocopherols; manufactured by Riken Vitamin Co., Ltd.), Riken E Oil (registered trademark) 505 (d-α-tocopherol; manufactured by Riken Vitamin Co., Ltd.), and Gamma Bright 90 (d-γ-tocopherol; manufactured by Mitsubishi Chemical Corporation), and these can be used in the present invention.

[0027] The L-ascorbic acid fatty acid ester preparation of the present invention can contain a non-reducing sugar in addition to the L-ascorbic acid fatty acid ester, powdered base material, organic acid salt and vitamin E. In the L-ascorbic acid fatty acid ester preparation of the present invention, when the L-ascorbic acid fatty acid ester, powdered base material, organic acid salt and vitamin E are added to water and emulsified to prepare an oil-in-water emulsion composition having a pH of 5.0 to 8.0, the L-ascorbic acid fatty acid ester preparation can contain a non-reducing sugar by adding a non-reducing sugar to water together with the L-ascorbic acid fatty acid ester, powdered base material, organic acid salt and vitamin E. Examples of the non-reducing sugar include sucrose and trehalose. By containing a non-reducing sugar in the L-ascorbic acid fatty acid ester preparation of the present invention, the stability of the L-ascorbic acid fatty acid ester preparation can be further improved.

[0028] The L-ascorbic acid fatty acid ester preparation of the present invention may contain other additives, such as emulsifiers, antioxidants (other than vitamin E and L-ascorbic acids (fat-soluble and water-soluble)), flavorings, etc., as necessary, within the scope of not impairing the object and effect of the present invention. Regarding other additives, the other additives may be added together with the raw materials when the raw materials are added to water.

[0029] In the L-ascorbic acid fatty acid ester preparation of the present invention, the content of the L-ascorbic acid fatty acid ester is preferably 5.0 to 40.0% by mass, more preferably 5.0 to 30.0% by mass, the content of the powdered base material is preferably 20.0 to 80.0% by mass, more preferably 40.0 to 65.0% by mass, the content of the organic acid salt is preferably 3.0 to 15.0% by mass, more preferably 5.0 to 10.0% by mass, the content of the vitamin E is preferably 5.0 to 50.0% by mass, more preferably 10.0 to 40.0% by mass, and when a non-reducing sugar is contained, the content of the non-reducing sugar is preferably 0.0 to 20.0% by mass, more preferably 5.0 to 15.0% by mass, and when other additives are contained, the amount of the other additives added is preferably 0.0 to 15.0% by mass, more preferably 0.0 to 10.0% by mass. In particular, the L-ascorbic acid fatty acid ester preparation of the present invention can have high stability even when the L-ascorbic acid fatty acid ester is contained in a high content, preferably 5.0 to 40.0% by mass, more preferably 5.0 to 30.0% by mass. Therefore, by having the content of L-ascorbic acid fatty acid ester in the L-ascorbic acid fatty acid ester preparation of the present invention within the above range, the effects of preventing oxidation of foods and beverages, suppressing flavor deterioration, preventing or suppressing fading, and preventing or suppressing discoloration can be further enhanced.

[0030] The L-ascorbic acid fatty acid ester preparation of the present invention is obtained by carrying out an emulsification step of adding an L-ascorbic acid fatty acid ester, a powdered base material, an organic acid salt, and vitamin E to water and emulsifying the mixture to prepare an oil-in-water emulsion composition having a pH of 5.0 to 8.0, and a drying step of drying the obtained oil-in-water emulsion composition. In the emulsification step, a non-reducing sugar can be added to the water together with the L-ascorbic acid fatty acid ester, the powdered base material, the organic acid salt, and vitamin E, if necessary.

[0031] In the emulsification step, L-ascorbic acid fatty acid ester, powdered base material, organic acid salt, and vitamin E are added to water, and if necessary, a non-reducing sugar is further added to water to emulsify. There is no particular restriction on the order in which the L-ascorbic acid fatty acid ester, powdered base material, organic acid salt, vitamin E, and non-reducing sugar used as needed are added to water and dispersed or dissolved, and they may be added to water sequentially to be dispersed or dissolved, or they may be added to water simultaneously to be dispersed or dissolved. When these are added simultaneously, "simultaneously" does not mean that they are added to water at exactly the same timing, and a certain time difference is allowed as long as an aqueous phase containing the L-ascorbic acid fatty acid ester, powdered base material, organic acid salt, vitamin E, and non-reducing sugar used as needed is prepared.

[0032] In the emulsification step, first, the L-ascorbic acid fatty acid ester, the powdered base material, the organic acid salt, and vitamin E are added to water, and if necessary, a non-reducing sugar is further added to the water.

[0033] The water is not particularly limited as long as it is drinkable, and examples thereof include purified water such as distilled water, ion exchange resin treated water, reverse osmosis membrane treated water, and ultrafiltration membrane treated water, tap water, natural water such as groundwater or spring water, and alkaline ionized water.

[0034] In the emulsification step, the aqueous phase containing the L-ascorbic acid fatty acid ester, the powdered base material, the organic acid salt, vitamin E, and the non-reducing sugar used as required is stirred and emulsified to prepare an oil-in-water emulsion composition. The equipment and processing conditions used for emulsification are appropriately selected so that a homogeneous oil-in-water emulsion can be prepared. For example, the aqueous phase containing the L-ascorbic acid fatty acid ester, the powdered base material, the organic acid salt, vitamin E, and the non-reducing sugar used as required is emulsified using a high-speed rotary dispersing / emulsifying machine at a rotation speed of 3000 to 15000 rpm and a stirring time of 5 to 30 minutes to prepare an oil-in-water emulsion composition.

[0035] In the emulsification step, when preparing the oil-in-water emulsion composition, the pH of the oil-in-water emulsion composition is set to 5.0 to 8.0, preferably 5.0 to 7.5. By setting the pH of the oil-in-water emulsion composition within the above range, the stability during production and long-term storage is good, and a high content of L-ascorbic acid fatty acid ester can be blended into food and drink, and an L-ascorbic acid fatty acid ester preparation having high antioxidant effect, flavor deterioration suppression effect, and color fading prevention or suppression effect and color change prevention or suppression effect can be obtained. If the pH of the oil-in-water emulsion composition is less than the above range, the L-ascorbic acid fatty acid ester is easily hydrolyzed, and if it exceeds the above range, browning or alkali decomposition of the L-ascorbic acid fatty acid ester occurs.

[0036] The above effect cannot be obtained with an L-ascorbic acid fatty acid ester preparation obtained by simply stirring and mixing an L-ascorbic acid fatty acid ester, a powdered base material, an organic acid salt, and vitamin E. By emulsifying an L-ascorbic acid fatty acid ester, a powdered base material, an organic acid salt, vitamin E, and a non-reducing sugar used as needed by adding them to water, and setting the pH of the oil-in-water emulsion composition within the above range, an L-ascorbic acid fatty acid ester preparation can be obtained that has good stability during production and long-term storage, and has a high antioxidant effect and / or flavor deterioration suppression effect, and further a high discoloration prevention or suppression effect when added to food or beverage.

[0037] In the emulsification step, the pH of the oil-in-water emulsion composition can be adjusted to 5.0 to 8.0, preferably 5.0 to 7.5, by selecting the type of organic acid salt and / or the amount of organic acid salt added.

[0038] In the emulsification step, the temperature of the oil-in-water emulsion composition when preparing the oil-in-water emulsion composition is appropriately selected, but is 40 to 80°C, preferably 60 to 80°C.

[0039] In the emulsification step, the apparatus for preparing the oil-in-water emulsion composition is not particularly limited, and for example, a normal stirring and mixing tank equipped with a stirrer, a heating jacket, a baffle plate, etc. can be used, and a high-speed rotary dispersion / emulsification machine such as TK Homomixer (manufactured by Primix) or Clearmix (manufactured by M Technique) is preferably used. The liquid emulsified by these devices may be further homogenized using a high-pressure homogenization machine. As the high-pressure homogenization machine, for example, APV Gaulin Homogenizer (manufactured by APV), Microfluidizer (manufactured by Powrex), Starburst (manufactured by Sugino Machine), Nanomizer (manufactured by Nanomizer), etc. can be preferably used. Instead of the homogenization machine, a homogenization machine such as an ultrasonic emulsifier may be used.

[0040] In the emulsification step, the amount of each of the raw materials (L-ascorbic acid fatty acid ester, powdered base material, organic acid salt, vitamin E, non-reducing sugar used as necessary, and other additives used as necessary) added to water is appropriately selected, but the amount of L-ascorbic acid fatty acid ester added is preferably 5.0 to 40.0 mass% and more preferably 5.0 to 30.0 mass% based on the total amount of the raw materials added to water. By adding the L-ascorbic acid fatty acid ester in the above range, the effects of preventing oxidation of food and drink, suppressing flavor deterioration, preventing or suppressing discoloration, and preventing or suppressing discoloration are further enhanced.

[0041] The amount of the powdered base material added to the water in the emulsification step is preferably 20.0 to 80.0% by mass, more preferably 40.0 to 65.0% by mass, based on the total amount of the raw materials added to the water. When the amount of the powdered base material added is within the above range, the L-ascorbic acid fatty acid ester is emulsified into a powder formulation.

[0042] The amount of organic acid salt added to water in the emulsification step is preferably 3.0 to 15.0% by mass, more preferably 5.0 to 10.0% by mass, based on the total amount of raw materials added to water. By adding the amount of organic acid salt within the above range, it becomes easier to adjust the pH of the oil-in-water emulsion composition to 5.0 to 8.0, preferably 5.0 to 7.5, and the effects of preventing oxidation of foods and beverages, suppressing flavor deterioration, and preventing or suppressing discoloration and discoloration are further enhanced.

[0043] The amount of vitamin E added to water in the emulsification step is preferably 5.0 to 50.0% by mass, more preferably 10.0 to 40.0% by mass, based on the total amount of raw materials added to water. By adding vitamin E in the above range, a synergistic effect with the L-ascorbic acid fatty acid ester and the organic acid salt is easily obtained, and the effects of preventing oxidation of foods and beverages, suppressing flavor deterioration, preventing or suppressing discoloration, and preventing or suppressing discoloration are further improved.

[0044] When non-reducing sugar is added to water in the emulsification step, the amount of non-reducing sugar added is preferably 0.0 to 20.0% by mass, more preferably 5.0 to 15.0% by mass, based on the total amount of raw materials added to water. By adding non-reducing sugar to water in the above range, the effects of preventing oxidation of food and drink, suppressing flavor deterioration, preventing or suppressing discoloration, and preventing or suppressing discoloration are enhanced, and the effect of masking the specific odor of vitamins is also enhanced.

[0045] When other additives are added in the emulsification step, the amount of the other additives added is preferably 0.0 to 15.0 mass %, more preferably 0.0 to 10.0 mass %, based on the total amount of raw materials added to water.

[0046] In the emulsification step, the amount of water used to prepare the oil-in-water emulsion composition is appropriately selected, but it is preferable that the amount of water be such that the total concentration of the raw materials (L-ascorbic acid fatty acid ester, powdered base material, organic acid salt, vitamin E, non-reducing sugar used as needed, and other additives used as needed) added to the water in the oil-in-water emulsion composition is 20.0 to 60.0% by mass.

[0047] In the drying step, the oil-in-water emulsion composition obtained in the emulsification step is dried. Examples of drying methods include spray drying, drum drying, belt drying, vacuum drying, and vacuum freeze drying, and spray drying is preferred. There is no particular limitation on the spray drying device used in the present invention, and known devices such as an injection type spray drying device or a rotary disk type spray device can be used. The device and processing conditions used in the drying treatment of the oil-in-water emulsion composition are appropriately selected so that the water is removed from the oil-in-water emulsion composition to obtain a powdered L-ascorbic acid fatty acid ester preparation.

[0048] Then, by carrying out an emulsification step and a drying step, the L-ascorbic acid fatty acid ester preparation of the present invention can be obtained.

[0049] The method for producing an L-ascorbic acid fatty acid ester preparation of the present invention is characterized by comprising an emulsification step of adding at least an L-ascorbic acid fatty acid ester, a powdered base material, an organic acid salt, and vitamin E to water and emulsifying the mixture to prepare an oil-in-water emulsion composition having a pH of 5.0 to 8.0, and a drying step of drying the obtained oil-in-water emulsion composition. Furthermore, in the method for producing an L-ascorbic acid fatty acid ester preparation of the present invention, in the emulsification step, non-reducing sugars and / or other additives can be added to water together with the L-ascorbic acid fatty acid ester, powdered base material, organic acid salt and vitamin E and emulsified.

[0050] The emulsification process, drying process, L-ascorbic acid fatty acid ester, powdered base material, organic acid salt, vitamin E, non-reducing sugar and other additives involved in the manufacturing method for the L-ascorbic acid fatty acid ester preparation of the present invention are the same as the emulsification process, drying process, L-ascorbic acid fatty acid ester, powdered base material, organic acid salt, vitamin E, non-reducing sugar and other additives involved in the above-mentioned L-ascorbic acid fatty acid ester preparation of the present invention.

[0051] The L-ascorbic acid fatty acid ester preparation of the present invention and the L-ascorbic acid fatty acid ester preparation obtained by carrying out the manufacturing method of the L-ascorbic acid fatty acid ester preparation of the present invention are obtained by first forming an oil-in-water emulsion composition from an L-ascorbic acid fatty acid ester, a powdered base material, an organic acid salt, vitamin E, and a non-reducing sugar used as necessary, and then drying the composition, so that the organic acid salt and the non-reducing sugar that work to enhance the stability of the L-ascorbic acid fatty acid ester coexist in a state where vitamin E and the L-ascorbic acid fatty acid ester are densely present by emulsification. Therefore, in the L-ascorbic acid fatty acid ester preparation of the present invention and the L-ascorbic acid fatty acid ester preparation obtained by carrying out the manufacturing method of the L-ascorbic acid fatty acid ester preparation of the present invention, the synergistic effect of the L-ascorbic acid fatty acid ester, the organic acid salt, and vitamin E, and the non-reducing sugar used as necessary, is easily obtained, so that the stability of the L-ascorbic acid fatty acid ester preparation during manufacturing and long-term storage can be increased.

[0052] Furthermore, in the L-ascorbic acid fatty acid ester preparation of the present invention and the L-ascorbic acid fatty acid ester preparation obtained by carrying out the manufacturing method for an L-ascorbic acid fatty acid ester preparation of the present invention, an oil-in-water emulsion composition in a state suitable for obtaining the effects of the present invention can be obtained by adjusting the pH of the oil-in-water emulsion composition to 5.0 to 8.0, preferably 5.0 to 7.5, so that the L-ascorbic acid fatty acid ester preparation of the present invention and the L-ascorbic acid fatty acid ester preparation obtained by carrying out the manufacturing method for an L-ascorbic acid fatty acid ester preparation of the present invention can have high stability during production and long-term storage of the L-ascorbic acid fatty acid ester preparation.

[0053] In addition, the L-ascorbic acid fatty acid ester preparation of the present invention and the L-ascorbic acid fatty acid ester preparation obtained by carrying out the method for producing the L-ascorbic acid fatty acid ester preparation of the present invention can have high stability during production and long-term storage, and therefore the content of L-ascorbic acid fatty acid ester can be increased, thereby improving the effects of preventing oxidation of foods and drinks, suppressing flavor deterioration, preventing or suppressing fading, and preventing or suppressing discoloration, etc. In the L-ascorbic acid fatty acid ester preparation of the present invention, vitamin E is emulsified as an oil-in-water type by the L-ascorbic acid fatty acid ester having amphiphilic properties, so there is no oil floating, and it is easily dispersed in water or water-rich food raw materials, so it can be dispersed uniformly.

[0054] The L-ascorbic acid fatty acid ester preparation of the present invention and the L-ascorbic acid fatty acid ester preparation obtained by carrying out the production method for the L-ascorbic acid fatty acid ester preparation of the present invention have high dispersibility in water or water-rich food materials and excellent stability even when containing a high content of L-ascorbic acid fatty acid ester. Therefore, the L-ascorbic acid fatty acid ester preparation of the present invention, which has little content loss during production and excellent stability, can be uniformly dispersed and blended into foods and beverages including milk and other dairy drinks, chlorophyll-containing beverages, matcha water, soft drinks, and other beverages, instant noodles in which a large amount of water is present in the dough during production because the dough is produced by adding water to wheat flour and kneading it, cookies such as matcha cookies, biscuits, and myoglobin-containing meats (for example, fish such as tuna, bonito, yellowtail, sardines, mackerel, horse mackerel, yellowtail, amberjack, herring, red sea bream, and other fish, marine mammals such as whales, livestock such as pigs, cows, sheep, and horses, poultry such as chickens, ducks, turkeys, and ducks, and wild birds and animals such as boars, deer, and bears). Therefore, the L-ascorbic acid fatty acid ester preparation of the present invention and the L-ascorbic acid fatty acid ester preparation obtained by the manufacturing method of the L-ascorbic acid fatty acid ester preparation of the present invention can fully exert effects such as preventing oxidation of food and beverages, suppressing flavor deterioration, preventing or suppressing fading, and preventing or suppressing discoloration.

[0055] The L-ascorbic acid fatty acid ester preparation of the present invention and the L-ascorbic acid fatty acid ester preparation obtained by carrying out the manufacturing method of the L-ascorbic acid fatty acid ester preparation of the present invention have high dispersibility in water and excellent stability even when containing a high content of L-ascorbic acid fatty acid ester, so when producing boiled processed foods of green vegetables such as boiled asparagus, the L-ascorbic acid fatty acid ester preparation of the present invention can be present in a high content and highly dispersed state in the water for boiling. Therefore, the L-ascorbic acid fatty acid ester preparation of the present invention and the L-ascorbic acid fatty acid ester preparation obtained by carrying out the manufacturing method of the L-ascorbic acid fatty acid ester preparation of the present invention can fully exert the effects of preventing oxidation of boiled processed foods, suppressing flavor deterioration, preventing or suppressing discoloration, and preventing or suppressing discoloration.

[0056] The present invention will be specifically described below by showing examples, but the present invention is not limited to the examples shown below. EXAMPLES

[0057] (Examples 1 to 12, Comparative Examples 1 to 10) [Preparation of L-ascorbic acid fatty acid ester formulation] (1) Raw materials 1) L-Ascorbyl palmitate (Watanabe Chemical Co., Ltd.) 2) L-Ascorbic acid stearate (Tokyo Chemical Industry Co., Ltd.) 3) Vitamin E (1) (Product name: Riken E Oil (registered trademark) 600; manufactured by Riken Vitamin Co., Ltd., mixed tocopherol) Vitamin E (2) (Product name: Riken E Oil (registered trademark) 505; manufactured by Riken Vitamin Co., Ltd., d-α-tocopherol) 4) Hardened palm oil (melting point 57°C; Yokoseki Oils & Fat Co., Ltd.) 5) Medium-chain triglyceride (product name: MCT Oil HC 100%; manufactured by Nisshin Oillio Co., Ltd.) 6) Trisodium citrate (product name: purified sodium citrate; manufactured by Fuso Chemical Co., Ltd.) 7) Sodium malate (product name: DL-sodium malate; manufactured by Fuso Chemical Co., Ltd.) 8) Sodium tartrate (Product name: Sodium L-tartrate; manufactured by Fuso Chemical Co., Ltd.) 9) Sodium gluconate (product name: Healthy A; manufactured by Fuso Chemical Co., Ltd.) 10) Sodium succinate (Product name: disodium succinate; manufactured by Fuso Chemical Co., Ltd.) 11) Sodium acetate (product name: anhydrous sodium acetate; manufactured by Fuso Chemical Co., Ltd.) 12) Sodium lactate (product name: sodium lactate (50%); manufactured by Fuso Chemical Co., Ltd.) 13) Sodium ascorbate (Product name: Sodium L-ascorbate; manufactured by Fuso Chemical Co., Ltd.) 14) Sodium fumarate (Product name: Monosodium fumarate; manufactured by Fuso Chemical Industry Co., Ltd.) 15) Sodium hydrogen carbonate (product name: sodium bicarbonate KF; manufactured by AGC) 16) Trehalose (product name: Treha; manufactured by Hayashibara Co., Ltd.) 17) Gum arabic (product name: San Arabic; manufactured by San-ei Pharmaceutical Trading Co., Ltd.) 18) Alkenyl succinate starch A (product name: N-Creamer 46; manufactured by Ingredion Japan) 19) Alkenyl succinate starch B (product name: Purity Gum BE; manufactured by Ingredion Japan) 20) Dextrin (product name: PineDeX #2; manufactured by Matsutani Chemical Co., Ltd.) 21) Vitamin E emulsified powder (product name: Fujimix E-20N; manufactured by Fuso Chemical Co., Ltd.) (2) Formulation of L-ascorbic acid fatty acid ester preparation The formulations of the L-ascorbic acid fatty acid ester preparations prepared using the above raw materials are shown in Table 1. They are named Example Products 1 to 12 and Comparative Examples Products 1 to 10. Note that Comparative Examples Products 5, 6, 8, and 9 are L-ascorbic acid fatty acid ester preparations prepared by separately mixing and adding vitamin E emulsion powder (Fujimix E-20N).

[0058] [Table 1]

[0059] [Table 2]

[0060] (3) Manufacturing Methods of Examples 1 to 12 and Comparative Examples 1 to 10 [Method A] 1) Tap water was poured into a 3L stainless steel mug and heated to 80°C. 2) While stirring the above 1) at low speed with a TK homogenizer (model: MARK2.5; manufactured by Primix Corporation), the powdered base material was added thereto, and this was stirred and dissolved at low speed with the same mixer for 10 minutes. 3) While further stirring the aqueous phase of 2) above at low speed, the organic acid salt, (and trehalose if necessary) and L-ascorbic acid fatty acid ester were added thereto, and this was stirred and dispersed in the same mixer at low speed for 10 minutes to obtain an aqueous phase containing the L-ascorbic acid fatty acid ester and powdered base material. 4) While stirring the aqueous phase of 3) at low speed, vitamin E preheated to 60℃ was gradually added, and the mixture was stirred and emulsified at 10,000 rpm for 15 minutes in the same mixer to obtain a homogenized liquid, which is an oil-in-water emulsion composition. The pH of this homogenized liquid was measured (model: LAQUA D-72LAB; manufactured by Horiba, Ltd.). 5) The homogenized liquid from 4) above was spray-dried in a spray dryer (model: Mini Spray Dryer B-290; Buchi) under conditions of a hot air inlet temperature of 170°C and an exhaust temperature of 80°C, and the dried product was collected in a cyclone to obtain a powdered L-ascorbic acid fatty acid ester preparation.

[0061] [Method B] 1) Tap water was poured into a 3L stainless steel mug and heated to 80°C. 2) While stirring the above 1) at low speed with a TK homogenizer (model: MARK2.5; manufactured by Primix Corporation), the powdered base material was added thereto, and this was stirred and dissolved at low speed with the same mixer for 10 minutes. 3) While the aqueous phase of 2) above was being stirred at low speed, vitamin E that had been preheated to 60°C was added thereto, and the mixture was stirred and dispersed at low speed for 10 minutes in the same mixer. 4) While stirring 3) at low speed, the organic acid salt (and trehalose if necessary) and L-ascorbic acid fatty acid ester were gradually added to 3), and then this was stirred and emulsified in the same mixer at 10,000 rpm for 15 minutes to obtain a homogenized liquid, which is an oil-in-water emulsion composition. The pH of this homogenized liquid was measured (model: LAQUA D-72LAB; manufactured by Horiba, Ltd.). 5) The homogenized liquid from 4) above was spray-dried in a spray dryer (model: Mini Spray Dryer B-290; Buchi) under conditions of a hot air inlet temperature of 170°C and an exhaust temperature of 80°C, and the dried product was collected in a cyclone to obtain a powdered L-ascorbic acid fatty acid ester preparation.

[0062] [Method C] 1) Tap water was poured into a 3L stainless steel mug and heated to 80°C. 2) While stirring the above 1) at low speed with a TK homogenizer (model: MARK2.5; manufactured by Primix), the organic acid salt (and trehalose, if necessary) and powdered base material were added thereto, and this was stirred and dissolved at low speed with the same mixer for 10 minutes. 3) While the aqueous phase of 2) above was being stirred at low speed, vitamin E heated to 60°C was added thereto, and the mixture was stirred and dispersed at low speed for 10 minutes in the same mixer. 4) While stirring 3) at low speed, L-ascorbic acid fatty acid ester was gradually added to 3), and then this was stirred and emulsified for 15 minutes at 10,000 rpm in the same mixer to obtain a homogenized liquid, which is an oil-in-water emulsion composition. The pH of this homogenized liquid was measured (model: LAQUA D-72LAB; manufactured by Horiba, Ltd.). 5) The homogenized liquid from 4) above was spray-dried in a spray dryer (model: Mini Spray Dryer B-290; Buchi) under conditions of a hot air inlet temperature of 170°C and an exhaust temperature of 80°C, and the dried product was collected in a cyclone to obtain a powdered L-ascorbic acid fatty acid ester preparation.

[0063] [Method D] 1) Tap water was poured into a 3L stainless steel mug and heated to 80°C. 2) While stirring the above 1) at low speed with a TK homogenizer (model: MARK2.5; manufactured by Primix Corporation), the powdered base material was added thereto, and this was stirred and dissolved at low speed with the same mixer for 10 minutes. 3) While the aqueous phase of 2) above was further stirred at low speed, sodium bicarbonate, trehalose, and L-ascorbyl palmitate were added thereto, and this was stirred and dispersed in the same mixer at low speed for 10 minutes to obtain an aqueous phase containing L-ascorbyl palmitate and powdered base material. 4) While stirring the aqueous phase of 3) at low speed, vitamin E preheated to 60℃ was gradually added, and the mixture was stirred and emulsified at 10,000 rpm for 15 minutes in the same mixer to obtain a homogenized liquid, which is an oil-in-water emulsion composition. The pH of this homogenized liquid was measured (model: LAQUA D-72LAB; manufactured by Horiba, Ltd.). 5) The homogenized liquid from 4) above was spray-dried in a spray dryer (model: Mini Spray Dryer B-290; Buchi) under conditions of a hot air inlet temperature of 170°C and an exhaust temperature of 80°C, and the dried product was collected in a cyclone to obtain a powdered L-ascorbic acid fatty acid ester preparation.

[0064] [Method E] 1) Tap water was poured into a 3L stainless steel mug and heated to 80°C. 2) While stirring the above 1) at low speed with a TK homogenizer (model: MARK2.5; manufactured by Primix Corporation), the powdered base material was added thereto, and this was stirred and dissolved at low speed with the same mixer for 10 minutes. 3) While the aqueous phase of 2) above was further stirred at low speed, trehalose and L-ascorbic acid fatty acid ester were added thereto, and this was stirred and dispersed in the same mixer at low speed for 10 minutes to obtain an aqueous phase containing L-ascorbic acid fatty acid ester and powdered base material. 4) While stirring the aqueous phase of 3) at low speed, vitamin E preheated to 60℃ was gradually added, and the mixture was stirred and emulsified at 10,000 rpm for 15 minutes in the same mixer to obtain a homogenized liquid, which is an oil-in-water emulsion composition. The pH of this homogenized liquid was measured (model: LAQUA D-72LAB; manufactured by Horiba, Ltd.). 5) The homogenized liquid from 4) above was spray-dried in a spray dryer (model: Mini Spray Dryer B-290; Buchi) under conditions of a hot air inlet temperature of 170°C and an exhaust temperature of 80°C, and the dried product was collected in a cyclone to obtain a powdered L-ascorbic acid fatty acid ester preparation.

[0065] [Method F] 1) Tap water was poured into a 3L stainless steel mug and heated to 80°C. 2) While stirring the above 1) at low speed with a TK homogenizer (model: MARK2.5; manufactured by Primix Corporation), the powdered base material was added thereto, and this was stirred and dissolved at low speed with the same mixer for 10 minutes. 3) While the aqueous phase of 2) above was further stirred at low speed, the L-ascorbic acid fatty acid ester was added thereto, and this was stirred and dispersed in the same mixer at low speed for 10 minutes to obtain an aqueous phase containing the L-ascorbic acid fatty acid ester and powdered base material. 4) While stirring the aqueous phase of 3) at low speed, vitamin E preheated to 60℃ was gradually added, and the mixture was stirred and emulsified at 10,000 rpm for 15 minutes in the same mixer to obtain a homogenized liquid, which is an oil-in-water emulsion composition. The pH of this homogenized liquid was measured (model: LAQUA D-72LAB; manufactured by Horiba, Ltd.). 5) The homogenized liquid from 4) above was spray-dried in a spray dryer (model: Mini Spray Dryer B-290; Buchi) under conditions of a hot air inlet temperature of 170°C and an exhaust temperature of 80°C, and the dried product was collected in a cyclone to obtain a powdered L-ascorbic acid fatty acid ester preparation.

[0066] [Method G] 1) Tap water was poured into a 3L stainless steel mug and heated to 80°C. 2) While stirring the above 1) at low speed with a TK homogenizer (model: MARK2.5; manufactured by Primix Corporation), the powdered base material was added thereto, and this was stirred and dissolved at low speed with the same mixer for 10 minutes. 3) While the aqueous phase of 2) above was further stirred at low speed, the organic acid salt, trehalose, and L-ascorbic acid fatty acid ester were added thereto, and this was stirred and dispersed in the same mixer at low speed for 10 minutes to obtain an aqueous phase containing the L-ascorbic acid fatty acid ester and powdered base material. 4) The aqueous phase of 3) above was stirred in the same mixer at 10,000 rpm for 15 minutes to obtain a homogenized liquid. pH measurement (model: LAQUA D-72LAB; manufactured by Horiba, Ltd.) was performed on this homogenized liquid. 5) The homogenized liquid from 4) above was spray-dried in a spray dryer (model: Mini Spray Dryer B-290; Buchi) under conditions of a hot air inlet temperature of 170°C and an exhaust temperature of 80°C, and the dried product was collected in a cyclone to obtain a powdered L-ascorbic acid fatty acid ester preparation.

[0067] [Method H] 1) A 300 mL glass beaker was charged with a solid oil at room temperature (i.e., extremely hardened palm oil), which was then heated to approximately 80°C while stirring with a glass rod. After confirming that the oil had dissolved uniformly, the temperature was increased to 110°C. 2) While stirring with a glass rod, L-ascorbic acid fatty acid ester was added little by little under the same temperature conditions, and completely dissolved. The obtained mixture was poured into a stainless steel tray, cooled at room temperature for 2 hours, and solidified, which was roughly crushed to obtain a flaky solid. The solid was crushed to an average particle size of about 100 μm using a crusher (model: SM-1C; set to "speed 10"; manufactured by AS ONE Co., Ltd.). This powdered L-ascorbic acid fatty acid ester was mixed with vitamin E emulsified powder to obtain an L-ascorbic acid fatty acid ester preparation (Comparative Example 6). In addition, since there is no process of adding water to obtain a homogenized liquid in this manufacturing method, pH measurement was not performed (it does not dissolve in water).

[0068] [Method I: No emulsification step] 1) Dextrin was added as a powder base material to a 3 L stainless steel mug and stirred at low speed for 10 minutes using a TK homogenizer (model: MARK2.5; manufactured by Primix Corporation). 2) While stirring 1) above at low speed, the organic acid salt, trehalose, and L-ascorbyl palmitate were added thereto, and the mixture was stirred at low speed in the same mixer for 10 minutes. 3) Vitamin E, which had been preheated to 60°C, was gradually added, and the mixture was stirred and homogenized in the same mixer at 10,000 rpm for 15 minutes to obtain a composition (Comparative Example Product I). Note that, since this manufacturing method does not include a step of adding water to obtain a homogenized liquid, pH was not measured. In addition, the finished L-ascorbic acid fatty acid ester formulation was a powder with high oiliness, and oil floating was confirmed when it was added to water.

[0069] [Stability of L-ascorbic acid fatty acid ester formulations] 100 g of each of the obtained L-ascorbic acid fatty acid ester preparations (Examples 1 to 12, Comparative Examples 1 to 10) was placed in a 1 L plastic bag and stored at 40° C. in a dark place for 30 or 60 days. The content of L-ascorbic acid fatty acid ester contained in the L-ascorbic acid fatty acid ester preparation was analyzed as follows. 0.5-1.0 g of L-ascorbic acid fatty acid ester preparation was weighed into a 50 mL centrifuge tube, 30 mL of ethanol was added, and the mixture was shaken for 5 minutes. After centrifugation, the upper layer was separated and taken into a 100 mL volumetric flask. This extraction was repeated three times. Ethanol was added, filtered, and the filtrate was appropriately diluted with ethanol. 2 mL was taken into a small test tube, and 2 mL of methanol was added. 1 mL of 1% DL-homocysteine ​​solution was added, and the mixture was left at 40°C for 15 minutes (reduction), and 1 mL of 1% L-ascorbic acid-methanol solution was added, and the volume was adjusted to 10 mL with methanol, and high performance liquid chromatography was performed. <High-performance liquid chromatography operating conditions> Model: LC-20AT (Shimadzu Corporation) Detector: SPD-20AV (Shimadzu Corporation) Column: L-Column ODS φ4.6mm×150mm (Chemicals Evaluation Institute, Japan) Mobile phase: A mixture of methanol and 0.05 mol / L sodium phosphate buffer (pH 2.0) (85:15) Flow rate: 1.0mL / min Measurement wavelength: 254nm Column temperature: 40℃ Injection volume: 20μL The content of L-ascorbic acid fatty acid ester in the L-ascorbic acid fatty acid ester preparation was measured, and the content by mass % (residual rate) of L-ascorbic acid fatty acid ester immediately after preparation and during storage was calculated relative to the amount of L-ascorbic acid fatty acid ester (100%). The results are shown in Table 3.

[0070] [Table 3]

[0071] The values ​​in the table indicate the content by mass (residual rate) of L-ascorbic acid fatty acid ester immediately after production and after storage, with the charged amount of L-ascorbic acid fatty acid ester being 100% by mass. From the results shown in Table 3, the L-ascorbic acid fatty acid ester preparations of Examples 1 to 12 had a high residual rate of L-ascorbic acid fatty acid ester and were stable even after long-term storage immediately after production. On the other hand, the results of Comparative Examples 1 to 6, 8, and 10 showed low residual rates immediately after production. In addition, the L-ascorbic acid fatty acid ester preparation of Comparative Example 2 (containing sodium bicarbonate) showed a brownish color of the powder immediately after production. The L-ascorbic acid fatty acid ester preparation of Comparative Example 7 (manufactured by a method not using an emulsification process) had good stability immediately after production, but poor storage stability. Comparative Example 9 was made of L-ascorbic acid fatty acid ester raw powder as is, so it had good stability immediately after production, but poor storage stability.

[0072] 1. Preparation and evaluation of instant noodles (fried instant noodles) (1) Ingredients for fried instant noodles Semi-strong wheat flour (product name: (Toku) Hiryu: manufactured by Nisshin Flour Milling Co., Ltd.) Acetylated tapioca starch (product name: Matsutani Sakura, manufactured by Matsutani Chemical Industry Co., Ltd.) - Table salt (product name: Nakru N: manufactured by Naikai Shoji Co., Ltd.) - Kansui (Product name: Powdered Kansui Red: manufactured by Oriental Yeast Co., Ltd.) L-ascorbic acid fatty acid ester preparations (Examples 1 to 12, Comparative Examples 1 to 10) (2) Manufacturing method of fried instant noodles Each of the specified raw materials was mixed for 10 minutes using a mixer-integrated noodle making machine (model: MODEL-MG-77; manufactured by Suzuki Menko Co., Ltd.), and the 1.0 mm thick noodle band obtained by rolling with a roll was cut into strips with a width of 1.2 mm to obtain each noodle strand. 200 g of each of these noodle strands was steamed at 100 to 102°C for 11 minutes, and 20 g of a spray liquid (aqueous solution of 40 g of salt, 10 g of white sugar, and 10 g of monosodium glutamate dissolved in 940 g of water) was sprayed onto each of the obtained steamed noodles, and then the noodles were molded. Each of the molded steamed noodles was fried in palm oil at 150°C for 60 seconds, and each of the obtained fried instant noodles was allowed to cool at room temperature. Each of the fried instant noodles allowed to cool at room temperature was placed in a plastic bag and then heat sealed. (3) Sensory evaluation of fried instant noodles The fried instant noodles obtained by method (2) above were stored in a dark place at a temperature of 40°C for 4 weeks and 8 weeks. A sensory evaluation of the fried instant noodles after storage was carried out. Evaluation was carried out by 10 panelists according to the sensory evaluation criteria shown in Table 4 below, and the average scores were calculated and coded according to the evaluation criteria shown below. The results are shown in Table 5. ◎: Very good, average score 3.5 or higher ○: Good, average score 3.0 or more, less than 3.5 △: Slightly poor Average score: 2.0 or more, less than 3.0 ×: Poor, average score less than 2.0

[0073] [Table 4]

[0074] [Table 5]

[0075] As is clear from the results in Table 5, the instant noodles containing the L-ascorbic acid fatty acid ester preparations of the present invention (Examples 1 to 12) had almost no deteriorated flavor even after long-term storage. In contrast, the instant noodles containing the L-ascorbic acid fatty acid ester preparations (Comparative Examples 1 to 10) had sensory evaluations of "△" or lower, and were inferior to those of the present invention.

[0076] 2. Evaluation of stability in dairy beverages (dispersibility, sensory) The L-ascorbic acid fatty acid ester preparations (Examples 1 to 12, Comparative Examples 1 to 10) in Tables 1 and 2 above were added to milk (Meiji Oishii Gyunyu: Meiji) so that the L-ascorbic acid fatty acid ester was added at an amount of 0.05% or 0.1%, and the beverages for each test group were filled into 50 ml colorless, transparent glass bottles, sealed, and shaken up and down by hand for 60 seconds to disperse the beverages in the milk. The samples were stored at 10℃ under 1500 Lux fluorescent light for 5 days. As a control, milk without the test sample was stored in the dark at 10℃. Ten panelists evaluated the product according to the evaluation criteria shown in Table 6 below, and the average scores were calculated and coded according to the evaluation criteria shown below. The results are shown in Tables 7 and 8. ◎: Very good, average score 3.5 or higher ○: Good, average score 3.0 or more, less than 3.5 △: Slightly poor Average score: 2.0 or more, less than 3.0 ×: Poor, average score less than 2.0

[0077] [Table 6]

[0078] [Table 7]

[0079] [Table 8]

[0080] As is clear from the results of Tables 7 and 8, the milk beverages obtained by adding the L-ascorbic acid fatty acid ester preparations of the present invention (Examples 1 to 12) had good dispersibility, and even after storage at 10° C. under light irradiation for 5 days, the sensory evaluation was excellent, with a result of “○” or higher. In contrast, the milk beverages obtained by adding the L-ascorbic acid fatty acid ester preparations (Comparative Examples 1 to 10) had a sensory evaluation of “△” or lower, and were inferior to those of the present invention.

[0081] 3. Stability evaluation of chlorophyll-containing foods and beverages [Preparation of anti-fading agent for chlorophyll-containing foods and beverages (containing L-ascorbic acid fatty acid ester preparation)] (1) Raw materials 1) Sodium ascorbate (product name: Sodium L-ascorbate; manufactured by Fuso Chemical Co., Ltd.) 2) Ascorbic acid (product name: L-ascorbic acid BP; manufactured by Fuso Chemical Co., Ltd.) 3) Citric acid (product name: purified citric acid (anhydrous); manufactured by Fuso Chemical Co., Ltd.) 4) Sodium fumarate (product name: monosodium fumarate; manufactured by Fuso Chemical Co., Ltd.) 5) Sodium malate (product name: DL-sodium malate; manufactured by Fuso Chemical Co., Ltd.) 6) Sodium hydrogen carbonate (product name: sodium bicarbonate KF; manufactured by AGC) 7) Sodium carbonate (product name: Soda Ash Light; manufactured by Tokuyama Corporation) 8) Dextrin (product name: PineDeX #2; manufactured by Matsutani Chemical Co., Ltd.) 9) Magnesium carbonate (product name: magnesium carbonate; manufactured by Kyowa Chemical Industry Co., Ltd.) 10) α-Lipoic acid (product name: α-Lipoic acid CD; manufactured by CycloChem) 11) Example Product 1 12) Example Product 9 13) Example Product 11 14) Example 12 15) Comparative Example 6 16) Comparative Example 8 17) Comparative Example 9 18) Comparative Example 10 19) Vitamin E emulsified powder (product name: Fujimix E-20N; manufactured by Fuso Chemical Co., Ltd.) (2) Contains anti-fading agents The compositions prepared using the above raw materials are shown in Tables 9 and 10. These were named Example Products 11 to 17 and Comparative Example Products 10 to 16.

[0082] [Table 9]

[0083] [Table 10]

[0084] [Preparation and evaluation of matcha water (color retention effect)] 88 parts by weight of tap water, 10 parts by weight of granulated sugar, and 2 parts by weight of matcha powder (product name: organic matcha; manufactured by Yamasan Co., Ltd.) were weighed out with 1 part by weight of the anti-fading agent (Examples 11 to 17, Comparative Examples 10 to 16) in Tables 9 and 10 above. After mixing the matcha, granulated sugar, and anti-fading agent, tap water was added and thoroughly mixed using a magnetic stirrer (model: MODEL M-16G; manufactured by Koike Precision Machinery Co., Ltd.). 20 ml of matcha water from each test group was filled into a transparent container. The mixture was left to stand for 7 days at 10°C under fluorescent light of 1500 Lux. As a control, matcha water without the addition of the test sample was stored in the dark at 10°C.

[0085] [Matcha water discoloration] Ten panelists checked the color fading according to the evaluation criteria shown in Table 11 below, calculated the average score, and coded according to the evaluation criteria shown below. In addition, the pH of the matcha water in each test group was measured and used as an index for evaluating the quality during storage. The results are shown in Table 12 (in parentheses in the table). ◎: Very good, average score 3.5 or higher ○: Good, average score 3.0 or more, less than 3.5 △: Slightly poor Average score: 2.0 or more, less than 3.0 ×: Poor, average score less than 2.0

[0086] [Table 11]

[0087] [Table 12]

[0088] As is clear from the results in Table 12, the anti-fading agents for chlorophyll-containing foods and beverages containing the L-ascorbic acid fatty acid ester preparations of the present invention (Examples 11 to 17) were excellent in inhibiting the fading of matcha water over a long period of time. In contrast, the anti-fading agents for chlorophyll-containing foods and beverages containing the L-ascorbic acid fatty acid ester preparations (Comparative Examples 10 to 16) showed a change in color after 2 days of storage and a large drop in the pH of matcha water.

[0089] [Sensory evaluation of matcha water] Ten panelists evaluated the product according to the evaluation criteria shown in Table 13 below, and the average scores were calculated and coded according to the evaluation criteria shown below. The results are shown in Tables 12 and 13. ◎: Very good, average score 3.5 or higher ○: Good, average score 3.0 or more, less than 3.5 △: Slightly poor Average score: 2.0 or more, less than 3.0 ×: Poor, average score less than 2.0

[0090] [Table 13]

[0091] [Table 14]

[0092] From Table 14, it was shown that the anti-fading agents for chlorophyll-containing foods and beverages containing the L-ascorbic acid fatty acid ester preparations of the present invention (Examples 11 to 17) did not cause the flavor of matcha to deteriorate over a long period of time. In contrast, it was confirmed that the anti-fading agents for chlorophyll-containing foods and beverages containing the L-ascorbic acid fatty acid ester preparations (Comparative Examples 10 to 16) had a weak effect of suppressing flavor deterioration.

[0093] [Preparation and evaluation of matcha cookies (color retention effect)] A dough was prepared by mixing 100 parts by weight of wheat flour (weak flour), 40 parts by weight of sugar, 1 part by weight of matcha powder, 50 parts by weight of unsalted butter, 10 parts by weight of egg yolk, 1 part by weight of baking powder, and 12 parts by weight of water. To this dough, 1 part by weight of the anti-fading agent (Examples 11 to 17, Comparative Examples 10 to 16) in Tables 9 and 10 was added, rolled out to a thickness of about 6 mm, cut, and baked in an oven at 180°C for 15 minutes to produce matcha cookies. The cookies were left to stand for 7 days at room temperature (25°C) under fluorescent light of 1000 Lux. As a control, matcha cookies without any test sample were prepared.

[0094] [Matcha cookie discoloration] The state of discoloration was checked by 10 panelists according to the evaluation criteria shown in Table 15 below, the average scores were calculated, and the average scores were coded according to the evaluation criteria shown below. The results are shown in Table 16. ◎: Very good, average score 3.5 or higher ○: Good, average score 3.0 or more, less than 3.5 △: Slightly poor Average score: 2.0 or more, less than 3.0 ×: Poor, average score less than 2.0

[0095] [Table 15]

[0096] [Table 16]

[0097] From Table 16, it was shown that the chlorophyll-containing food and drink discoloration inhibitors containing the L-ascorbic acid fatty acid ester preparations of the present invention (Examples 11 to 17) were excellent in inhibiting the discoloration of matcha cookies for a long period of time. In contrast, the chlorophyll-containing food and drink discoloration inhibitors containing the L-ascorbic acid fatty acid ester preparations (Comparative Examples 10 to 16) showed a change in color from 2 days onwards.

[0098] [Sensory evaluation of matcha cookies] Ten panelists evaluated the product according to the evaluation criteria shown in Table 17 below, and the average scores were calculated and coded according to the evaluation criteria shown below. The results are shown in Table 18. ◎: Very good, average score 3.5 or higher ○: Good, average score 3.0 or more, less than 3.5 △: Slightly poor Average score: 2.0 or more, less than 3.0 ×: Poor, average score less than 2.0

[0099] [Table 17]

[0100] [Table 18]

[0101] From Table 18, it was shown that the discoloration inhibitors for chlorophyll-containing foods and beverages containing the L-ascorbic acid fatty acid ester preparations of the present invention (Examples 11 to 17) suppressed the flavor deterioration of matcha cookies for a long period of time. On the other hand, it was confirmed that the discoloration inhibitors for chlorophyll-containing foods and beverages containing the L-ascorbic acid fatty acid ester preparations (Comparative Examples 10 to 16) did not have a long-term flavor deterioration suppression effect.

[0102] [Production and evaluation of green vegetables (boiled asparagus) (effect of color retention)] 1% by weight of salt and 2% by weight of each of the prepared anti-fading agents (Examples 11 to 17, Comparative Examples 10 to 16) shown in Tables 9 and 10 were added to boiling water. The aqueous solution was heated and when it boiled, asparagus was added. After re-boiling, the water was heated for 1 minute and drained to obtain boiled asparagus. In addition, boiled asparagus was produced in the same manner except that an aqueous solution with a salt concentration of 1% by weight was used, and used as a control for the sensory evaluation and appearance evaluation. The mixture was left to stand at 5° C. under fluorescent light of 1,500 Lux for 3 days.

[0103] [Discoloration of green vegetables] The state of discoloration was checked by 10 panelists according to the evaluation criteria shown in Table 19 below, the average scores were calculated, and the average scores were coded according to the evaluation criteria shown below. The results are shown in Table 20. ◎: Very good, average score 3.5 or higher ○: Good, average score 3.0 or more, less than 3.5 △: Slightly poor Average score: 2.0 or more, less than 3.0 ×: Poor, average score less than 2.0

[0104] [Table 19]

[0105] [Table 20]

[0106] From Table 20, it was shown that the chlorophyll-containing food and drink discoloration inhibitors containing the L-ascorbic acid fatty acid ester preparations of the present invention (Examples 11 to 17) were excellent in inhibiting discoloration of green vegetables for a long period of time. In contrast, the chlorophyll-containing food and drink discoloration inhibitors containing the L-ascorbic acid fatty acid ester preparations (Comparative Examples 10 to 16) showed a change in color after one day.

[0107] [Sensory evaluation of green vegetables] Ten panelists evaluated the product according to the evaluation criteria shown in Table 21 below, and the average scores were calculated and coded according to the evaluation criteria shown below. The results are shown in Table 22. ◎: Very good, average score 3.5 or higher ○: Good, average score 3.0 or more, less than 3.5 △: Slightly poor Average score: 2.0 or more, less than 3.0 ×: Poor, average score less than 2.0

[0108] [Table 21]

[0109] [Table 22]

[0110] From Table 22, it was shown that the discoloration inhibitor for chlorophyll-containing foods and beverages containing the L-ascorbic acid fatty acid ester preparations of the present invention (Examples 11 to 17) suppresses the flavor deterioration of green vegetables for a long period of time. On the other hand, it was confirmed that the discoloration inhibitor for chlorophyll-containing foods and beverages containing the L-ascorbic acid fatty acid ester preparations (Comparative Examples 10 to 16) does not have a long-term flavor deterioration suppression effect.

[0111] 4. Preparation and Evaluation of Tuna Fillets (1) Raw materials · Bigeye tuna fillet (frozen) L-ascorbic acid fatty acid ester preparations (Examples 1 to 12, Comparative Examples 1 to 10) (2) Tuna fillet processing method Frozen tuna fillets were cut to a thickness of about 8 mm and immersed in various immersion solutions containing 2% of the L-ascorbic acid fatty acid ester formulations (Examples 1 to 12, Comparative Examples 1 to 10) shown in Tables 1 and 2 at 4°C for 5 minutes. After immersion, the tuna fillets were drained for 10 minutes and then placed in a plastic bag (Unipack H-8 (thickness 0.08 mm); Seisan Nippon Sha) and stored at 4°C.

[0112] [Prevention of discoloration (or browning) of tuna fillets] According to the evaluation criteria shown in Table 23 below, 10 panelists visually confirmed the discoloration (or browning) state, calculated the average score, and coded according to the following criteria. The "pH measurement of tuna fillet" is the value measured by putting 10g of tuna fillet and 90g of ion-exchanged water in a food processor, finely grinding the tuna, and measuring the liquid containing the pulverized flesh (pH meter type: D-72LAB; manufactured by Horiba, Ltd.), and is used as an index of food preservation and color retention. The results are shown in Table 24 (in parentheses in the table). ◎: Very good, average score 3.5 or higher ○: Good, average score 3.0 or more, less than 3.5 △: Slightly poor Average score: 2.0 or more, less than 3.0 ×: Poor, average score less than 2.0

[0113] [Table 23]

[0114] [Table 24]

[0115] As is clear from the results in Table 24 above, the product of the present invention was excellent in the effect of inhibiting discoloration (or browning) of tuna fillets over a long period of time. In contrast, the comparative product and the control product showed a change in color from 2 days onwards.

[0116] [Sensory evaluation of tuna fillets] Ten panelists evaluated the product according to the evaluation criteria shown in Table 25 below, and the average scores were calculated and coded according to the following criteria. The results are shown in Table 26. ◎: Very good, average score 3.5 or higher ○: Good, average score 3.0 or more, less than 3.5 △: Slightly poor Average score: 2.0 or more, less than 3.0 ×: Poor, average score less than 2.0

[0117] [Table 25]

[0118] [Table 26]

[0119] From Table 26 above, it was confirmed that the tuna fillets containing the product of the present invention had an excellent effect of suppressing flavor deterioration for a long period of time. In contrast, it was confirmed that the tuna fillets containing the comparative product and the control product had a weak effect of suppressing flavor deterioration.

[0120] 5. Preparation and evaluation of Negitoro Negitoro was prepared by adding 100g of edible oil (Tromiyu; NOF Corp.) to 900g of frozen tuna fillet, crushing and mixing it in a grinder. 1% of L-ascorbic acid fatty acid ester preparations (Examples 1-12, Comparative Examples 1-10) in Tables 1 and 2 and 0.3% of an acid-type shelf life enhancer (product name: anhydrous sodium acetate; Fuso Chemical Co., Ltd.) were added to the negitoro, which was then placed in a plastic bag (Unipack H-8 (thickness 0.08mm; Nippon Seisan Co., Ltd.) and stored at 10°C.

[0121] [Prevention of discoloration (or browning) of negitoro] According to the evaluation criteria shown in Table 27 below, 10 panelists visually confirmed the discoloration (or browning) state, calculated the average score, and coded according to the following criteria. The "pH measurement of Negitoro" was done by putting 10g of Negitoro and 90g of ion-exchanged water in a food processor, and measuring the liquid containing the finely ground flesh (pH meter type: D-72LAB; manufactured by Horiba, Ltd.), and is used as an index of food preservation and color retention. The results are shown in Table 28 (in parentheses in the table). ◎: Very good, average score 3.5 or higher ○: Good, average score 3.0 or more, less than 3.5 △: Slightly poor Average score: 2.0 or more, less than 3.0 ×: Poor, average score less than 2.0

[0122] [Table 27]

[0123] [Table 28]

[0124] As is clear from the results in Table 28 above, the product of the present invention was excellent in the effect of inhibiting discoloration (or browning) of negitoro for a long period of time, even when used in combination with an acid-type shelf life improver. In contrast, the comparative product and the control product used in combination with an acid-type shelf life improver showed a change in color after one day of storage.

[0125] [Sensory evaluation of Negitoro] Ten panelists evaluated the product according to the evaluation criteria shown in Table 29 below, and the average scores were calculated and coded according to the following criteria. The results are shown in Table 30. ◎: Very good, average score 3.5 or higher ○: Good, average score 3.0 or more, less than 3.5 △: Slightly poor Average score: 2.0 or more, less than 3.0 ×: Poor, average score less than 2.0

[0126] [Table 29]

[0127] [Table 30]

[0128] From Table 30 above, it was confirmed that the negitoro containing the product of the present invention and an acid-type shelf life improver in combination had an excellent effect of suppressing flavor deterioration over a long period of time. In contrast, the negitoro containing the comparative product and an acid-type shelf life improver in combination had a weak effect of suppressing flavor deterioration.

[0129] 6. Preparation and Evaluation of Beef Steaks Beef (Angus beef shoulder roast; purchased from a supermarket, approximately 250 g) was dusted with 1.5% of the L-ascorbic acid fatty acid ester preparations (Examples 1 to 12, Comparative Examples 1 to 10) shown in Tables 1 and 2 based on the weight of the meat (sprinkled evenly over the surface of the meat).

[0130] [Prevents discoloration (or browning) of beef steaks] Ten panelists visually confirmed the discoloration (or browning) state according to the evaluation criteria shown in Table 31 below, calculated the average score, and coded according to the following criteria. The results are shown in Table 32. ◎: Very good, average score 3.5 or higher ○: Good, average score 3.0 or more, less than 3.5 △: Slightly poor Average score: 2.0 or more, less than 3.0 ×: Poor, average score less than 2.0

[0131] [Table 31]

[0132] [Table 32]

[0133] As is clear from the results in Table 32 above, the product of the present invention was excellent in inhibiting discoloration (or browning) of beef steaks for a long period of time. In contrast, the comparative product and the control product showed a change in color after storage for one day or more.

[0134] [Sensory evaluation of beef steak] Ten panelists evaluated the product according to the evaluation criteria shown in Table 33 below, and the average scores were calculated and coded according to the following criteria. The results are shown in Table 34. ◎: Very good, average score 3.5 or higher ○: Good, average score 3.0 or more, less than 3.5 △: Slightly poor Average score: 2.0 or more, less than 3.0 ×: Poor, average score less than 2.0

[0135] [Table 33]

[0136] [Table 34]

[0137] From Table 34 above, it was confirmed that the beef steak containing the product of the present invention had an excellent effect of suppressing flavor deterioration for a long period of time. On the other hand, the beef steak containing the comparative product had a weak effect of suppressing flavor deterioration.

Claims

1. The L-ascorbic acid fatty acid ester preparation is obtained by adding an L-ascorbic acid fatty acid ester, a powdered base material, an organic acid salt and vitamin E to water to emulsify the mixture, thereby obtaining an oil-in-water emulsion composition having a pH of 5.0 to 8.0, and then drying the obtained oil-in-water emulsion composition.

2. The L-ascorbic acid fatty acid ester preparation according to claim 1, characterized in that the organic acid salt is at least one selected from the group consisting of sodium salts, potassium salts and calcium salts of citric acid, malic acid, tartaric acid, gluconic acid, succinic acid, acetic acid, lactic acid and ascorbic acid.

3. 2. The L-ascorbic acid fatty acid ester preparation according to claim 1, further comprising a non-reducing sugar.

4. The L-ascorbic acid fatty acid ester preparation according to any one of claims 1 to 3, characterized in that it has at least one of the following properties: prevention of oxidation, suppression of flavor deterioration, prevention or suppression of discoloration, and prevention or suppression of discoloration of foods and beverages.

5. an emulsification step of adding at least an L-ascorbic acid fatty acid ester, a powdered base material, an organic acid salt, and vitamin E to water and emulsifying the mixture to prepare an oil-in-water emulsion composition having a pH of 5.0 to 8.0; a drying step of drying the obtained oil-in-water emulsion composition; The method for producing an L-ascorbic acid fatty acid ester preparation comprising the steps of:

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