JP6796055B2 - L-ascorbic acid fatty acid ester preparation - Google Patents

Description

The present invention relates to L-ascorbic acid fatty acid ester preparations.

L-ascorbic acid fatty acid ester is an ester bond of fatty acid to L-ascorbic acid, has vitamin C action and antioxidant action, and is lipophilic, so it is mainly used for nutrition of foods containing edible fats and oils and fats. It is used as a fortifier, antioxidant, etc. However, since L-ascorbic acid fatty acid ester has poor dispersibility in water (water dispersibility), for example, even if it is used as it is in an aqueous food such as refreshing drinking water, a crystal of L-ascorbic acid fatty acid ester in the food. Will float without being dispersed. Therefore, in order to make the L-ascorbic acid fatty acid ester widely applicable to various foods and drinks, various formulation methods are being studied.

Examples of such a method include an aqueous dispersible ascorbic acid fatty acid ester composition (Patent Document 1) containing an ascorbic acid fatty acid ester, a hydrophilic surfactant and an oligosaccharide, and an L-ascorbic acid fatty acid ester. An antioxidant preparation characterized by being uniformly dispersed in an oily substance (Patent Document 2), and a hydrophilic inclusion complex formed by emulsifying a higher fatty acid ester of L-ascorbic acid with cyclodextrin (Patent Document 2). 3), L-ascorbic acid fatty acid ester, powdered base material and oil-soluble substance are added to water to emulsify, and the obtained oil-in-water emulsified composition is dried to produce a powdered L-ascorbic acid fatty acid ester preparation. A method (Patent Document 4) and the like are known.

However, even if the preparations obtained by these methods are added to the dough of foods mainly composed of flour and / or starch (for example, snack foods) and used, a sufficient antioxidant effect cannot be obtained, and thus they can be replaced. A novel L-ascorbic acid fatty acid ester preparation has been sought.

Japanese Unexamined Patent Publication No. 7-115951 Japanese Unexamined Patent Publication No. 9-208986 Japanese Unexamined Patent Publication No. 10-231244 Japanese Unexamined Patent Publication No. 2014-155453

An object of the present invention is to provide an L-ascorbic acid fatty acid ester preparation which can obtain a sufficient antioxidant effect by being added to a dough of a food mainly containing flour and / or starch.

As a result of diligent studies on the above-mentioned problems, the present inventors have solved the above-mentioned problems with the L-ascorbic acid fatty acid ester preparation obtained by formulating a solid fat or oil at room temperature by a specific method. It was found that it could be solved, and the present invention was made based on this finding.

That is, the present invention
A powdery L-ascorbic acid fatty acid ester preparation containing particles containing (1) (a) L-ascorbic acid fatty acid ester and (b) fats and oils solid at room temperature.
(2) L-ascorbic acid fatty acid ester preparation obtained by cooling and powdering a melted mixture containing (a) L-ascorbic acid fatty acid ester and (b) solid fats and oils at room temperature.
(3) The preparation according to claim 1 or 2, for suppressing an increase in peroxide value and / or flavor deterioration of foods and drinks.
(4) A method for producing an L-ascorbic acid fatty acid ester preparation, which comprises a step of cooling and powdering a melted mixture containing (a) L-ascorbic acid fatty acid ester and (b) solid fats and oils at room temperature. ,
Including.

In the food or drink to which the L-ascorbic acid fatty acid ester preparation of the present invention is added, an increase in peroxide value and / or a deterioration in flavor due to the progress of oxidation of fats and oils contained in the food or drink is sufficiently suppressed.
The L-ascorbic acid fatty acid ester preparation of the present invention can sufficiently suppress the oxidation of the food by adding it to the dough of the food mainly composed of flour and / or starch.

The constituent fatty acids of the L-ascorbic acid fatty acid ester used in the present invention are not particularly limited as long as they are fatty acids derived from edible animal and vegetable fats and oils, and are, for example, linear saturated or unsaturated fatty acids having 6 to 24 carbon atoms. Examples include fatty acids, preferably linear saturated or unsaturated fatty acids having 16 to 18 carbon atoms. Examples of the L-ascorbic acid fatty acid ester used in the present invention include L-ascorbic acid stearic acid ester (food additive) and L-ascorbic acid palmitic acid ester (food additive), all of which are preferably used. However, L-ascorbic acid palmitic acid ester is more preferable because of its relatively low melting point and high vitamin C activity due to its small molecular weight.

As the fats and oils that are solid at room temperature used in the present invention, well-known edible fats and oils that are solid or semi-solid at room temperature (10 to 35 ° C.) can be used, for example, lard, palm oil, palm oil, and the like. Contains animal fats such as beef tallow, lard, and cacao fat, vegetable fats, and hardened fats and oils obtained by hydrogenating liquid animal and vegetable oils (including extremely hardened fats and oils having an iodine value of 2 or less). ), Which is preferably an extremely hardened fat. As the fats and oils that are solid at room temperature used in the present invention, they may be used alone, or two or more of them may be used in combination.

The method for producing the L-ascorbic acid fatty acid ester preparation of the present invention is not particularly limited. For example, a melted mixture containing (a) L-ascorbic acid fatty acid ester and (b) fats and oils solid at room temperature can be prepared. A powdery L-ascorbic acid fatty acid ester preparation containing particles containing (a) L-ascorbic acid fatty acid ester and (b) solid fats and oils at room temperature is obtained by a method including a step of cooling and pulverizing. Be done. The specific production method is not particularly limited, but for example, (1) one or more types of fats and oils that are solid at room temperature are heated to a melting point or higher (for example, 60 to 90 ° C.) to be melted and mixed. After raising the temperature to 100 to 120 ° C., L-ascorbic acid fatty acid ester is added to melt and mix, and the obtained mixture is spray-cooled under temperature conditions of -196 to 30 ° C. to form a powdery L-. A method of recovering as an ascorbic acid fatty acid ester preparation, (2) The mixture is allowed to stand at a temperature of, for example, -196 ° C. to room temperature for 1 to 72 hours to be cooled and solidified, and then pulverized by a method known per se and powdered. A method for preparing an L-ascorbic acid fatty acid ester preparation in the form of a form can be carried out.

In the above methods (1) and (2), the ratio of the L-ascorbic acid fatty acid ester to the fat and oil solid at room temperature (L-ascorbic acid fatty acid ester / fat and oil solid at room temperature) in the mixture is not particularly limited. However, for example, the mass ratio is preferably 1/99 to 60/40, more preferably 10/90 to 45/55.

Further, in the method (1) above, spray cooling is carried out, for example, by using a general spray cooling device and spraying the melt into a tower filled with, for example, a cooled gas. When liquid nitrogen is used to cool the gas in the tower, the liquid nitrogen may be injected from any of the upper, middle and lower stages in the tower, or may be injected from two or more places. A pressurized spray nozzle, a rotary disk spray nozzle, or the like is used for spraying. The sprayed solution is cooled into powder, which falls to the bottom of the tower and is collected. The average particle size of the obtained powder is not particularly limited, but is preferably 50 to 1000 μm, and more preferably 100 to 500 μm.

Further, in the method (2) above, the crushing method may be physically finely crushed, and for example, a compression crusher, a shear crusher, an impact crusher, a roll mill, a high-speed rotary mill, a jet mill or the like is used. Examples thereof include known pulverization methods described above. The degree of pulverization is not particularly limited, but for example, pulverization is preferably performed so that the average particle size is preferably in the range of 50 to 1000 μm, more preferably 100 to 500 μm.

The L-ascorbic acid fatty acid ester preparation of the present invention is in powder form. The average particle size of the powder is not particularly limited, but is preferably 50 to 1000 μm, more preferably 100 to 500 μm.

To the L-ascorbic acid fatty acid ester preparation of the present invention, for example, a food emulsifier, an antioxidant (excluding the L-ascorbic acid fatty acid ester), etc. are added as long as the object and effect of the present invention are not impaired. be able to.

Examples of the emulsifier for foods include glycerin fatty acid ester, sucrose fatty acid ester, sorbitan fatty acid ester, propylene glycol fatty acid ester, lecithin and the like. Here, the glycerin fatty acid ester includes glycerin and fatty acid ester, glycerin acetic acid ester, glycerin acetic acid fatty acid ester, glycerin lactic acid fatty acid ester, glycerin ene acid fatty acid ester, glycerin succinic acid fatty acid ester, glycerin diacetyl tartrate fatty acid ester, and poly. Includes glycerin fatty acid ester, polyglycerin condensed ricinoleic acid ester and the like. Further, lecithin includes fractionated lecithin, enzymatically decomposed lecithin, enzyme-treated lecithin and the like. Since the L-ascorbic acid fatty acid ester preparation of the present invention contains an emulsifier for food, the water dispersibility and the like are enhanced, and it can be widely applied to various foods and drinks.

Examples of the antioxidant include extracted tocopherol, rosemary extract, L-ascorbic acid and its salts, catechins, enzyme-treated rutin, sunflower seed extract, grape seed extract, enzymatically decomposed apple extract, BHA, BHT, and the like. Examples include TBHQ and EDTA.

The type of food or drink for which the L-ascorbic acid fatty acid ester preparation of the present invention is used is not particularly limited, and can be widely used for various foods and drinks including foods mainly composed of flour and / or starch. Foods mainly composed of flour and / or starch include, for example, bakeries such as bread, cookies, crackers, biscuits, cakes, pizzas and pies, pastas such as spaghetti and macaroni, noodles such as udon, buckwheat and ramen. Snacks such as okaki, potato chips, snacks, cake donuts, yeast donuts, fried bread, karinto, hemp flowers, sirter andagi, churos, fried buns, American dogs, piroshki, fritters, tempura, cutlets, fried pizza and other oily foods Examples include Japanese sweets such as donuts, buns, piro, mochi, and ohagi.

Examples of the flour include wheat flour, buckwheat flour, barley flour, rice flour and the like. Examples of starch include potato starch, tapioca starch, waxy cornstarch, cornstarch, wheat starch, etherified modified starch, esterified modified starch, crosslinked modified starch, oxidized modified starch, etc. obtained from these as raw materials, and many other starches. It also includes the food material it contains (eg, dried potato starch, dried mashed potatoes, dried potato flakes, etc.).

In foods mainly composed of flour and / or starch, the proportion of flour and / or starch in the raw material flour of the food is, for example, 50% by mass or more, preferably 70% by mass or more, and more preferably 80% by mass of the total raw material flour. It may be% or more. The proportion of flour and / or starch in the raw material of foods mainly composed of flour and / or starch is, for example, 20% by mass or more, preferably 40% by mass or more, and more preferably 60% by mass or more of the total raw material. You may.

Foods and drinks other than foods mainly composed of cereal flour and / or starch include, for example, Western confectionery materials such as chocolate and nuts, soymilk, soybean foods such as soybean milk, and tofu, milk, cheese, butter, ice cream, cream, Milk foods and drinks such as pudding, yogurt, fermented milk drinks, milk-containing drinks, hamburgers, sausages, fish sausages, tsumire, processed livestock and marine products such as boiled and dried, EPA (eikosapentaenoic acid), DHA (docosahexaenoic acid), Examples thereof include fats and oils such as fish oil, perilla oil, soybean oil, rapeseed oil, margarine and shortening, and processed fats and oils.

The method of using the L-ascorbic acid fatty acid ester preparation of the present invention is not particularly limited, and can be added to the dough of the food, for example, in the production of foods mainly composed of flour and / or starch. More specifically, in the production of foods mainly composed of flour and / or starch, (1) an L-ascorbic acid fatty acid ester preparation is added to the flour and / or starch and mixed, and the obtained mixture is used as a raw material flour. Examples thereof include a method of preparing a dough, and (2) a method of adding an L-ascorbic acid fatty acid ester preparation to a dough mainly composed of flour and / or starch and kneading the dough. Methods for producing foods from dough have been well established in the past and may be followed in the present invention using L-ascorbic acid fatty acid ester preparations.

The amount of the L-ascorbic acid fatty acid ester preparation of the present invention used for foods mainly composed of flour and / or starch is not particularly limited, but for example, it is usually 0.01 to 1 per 100 parts by mass of flour and / or starch. It is by mass, preferably 0.05 to 0.5 parts by mass.

The L-ascorbic acid fatty acid ester preparation of the present invention is used for applications such as suppressing oxidation of foods and drinks (including suppressing oxidation by light), suppressing an increase in peroxide value, and suppressing deterioration of flavor.

Hereinafter, the present invention will be specifically described with reference to Examples, but the present invention is not limited thereto.

[Manufacturing of L-ascorbic acid fatty acid ester preparation]
(1) Raw materials 1) L-ascorbic acid palmitic acid ester (manufactured by Watanabe Chemical Co., Ltd.)
2) L-ascorbic acid stearic acid ester (manufactured by Tokyo Chemical Industry Co., Ltd.)
3) Palm extremely hydrogenated oil (melting point 57 ° C; manufactured by Yokoseki Oil & Fat Co., Ltd.)
4) Rapeseed extremely hydrogenated oil (melting point 67 ° C; manufactured by Yokoseki Oil & Fat Co., Ltd.)
5) Extremely hardened soybean oil (melting point 67 ° C; manufactured by Yokoseki Oil & Fat Co., Ltd.)
6) Glycerin fatty acid ester (Product name: Poem DO-100V; manufactured by RIKEN Vitamin Co., Ltd.)
7) Medium-chain fatty acid triglyceride (Product name: Actor M-1; manufactured by RIKEN Vitamin Co., Ltd.)
8) Modified starch A (Product name: N creamer 46; manufactured by Ingredion Japan)
9) Modified starch B (Product name: Purity Gum BE; manufactured by Ingredion Japan)

(2) Formulation of L-ascorbic acid fatty acid ester preparation Table 1 shows the composition of the L-ascorbic acid fatty acid ester preparation prepared using the above raw materials. Of these, L-ascorbic acid fatty acid ester preparations 1 to 6 are examples according to the present invention, and L-ascorbic acid fatty acid ester preparations 7 and 8 are comparative examples thereof. The amount of preparations 1 to 6 and 8 was 100 g, and the amount of preparation 7 was 420 g.

(3) Method for producing L-ascorbic acid fatty acid ester preparations 1 to 5 Solid fats and oils in a 300 mL glass beaker at room temperature (that is, any of palm extremely hydrogenated oil, rapeseed extremely hydrogenated oil, and soybean extremely hydrogenated oil) Was heated to around 80 ° C. while stirring with a glass rod, and after confirming that the mixture was uniformly dissolved, the temperature was raised to 110 ° C. L-ascorbic acid fatty acid ester (that is, L-ascorbic acid palmitic acid ester or L-ascorbic acid stearic acid ester) was added little by little under the same temperature condition while stirring with a glass rod, and the mixture was completely dissolved. The obtained mixture was poured into a stainless steel tray, cooled at room temperature for 2 hours, and solidified, which was roughly pulverized to obtain a flake-like solid. The solid matter is crushed to an average particle size of about 100 μm using a crusher (model: SM-1C; set to “speed 10”; manufactured by AS ONE Corporation), and powdered L-ascorbic acid fatty acid ester preparations 1 to 5 are used. Got

(4) Method for producing L-ascorbic acid fatty acid ester preparation 6 Palm extremely hydrogenated oil and glycerin fatty acid ester were placed in a 300 mL glass beaker and heated to around 80 ° C. with stirring with a glass rod to uniformly dissolve them. After confirming that, the temperature was raised to 110 ° C. While stirring this with a glass rod, L-ascorbic acid palmitic acid ester was added little by little under the same temperature conditions, and the mixture was completely dissolved. The obtained mixture was poured into a stainless steel tray, cooled at room temperature for 2 hours, and solidified, which was roughly pulverized to obtain a flake-like solid. The solid substance is pulverized to an average particle size of about 100 μm using a pulverizer (model: SM-1C; set to “speed 10”; manufactured by AS ONE Corporation) to obtain a powdered L-ascorbic acid fatty acid ester preparation 6. It was.

(5) Method for Producing L-Ascorbic Acid Fatty Acid Ester Preparation 7 1) 2000 mL of tap water was placed in a 3 L stainless steel jug and heated to 80 ° C.
2) While stirring the above 1) with a clear mixer (model: S942; manufactured by M-Technique Co., Ltd.) at low speed, add modified starch A and modified starch B as a powdered base material, and add this to the mixture at low speed with the same mixer. Stir and dissolve for 10 minutes.
3) While further stirring the aqueous phase of 2) above at low speed, L-ascorbic acid palmitic acid ester was added thereto, and this was stirred and dispersed at low speed for 10 minutes with the same mixer to obtain L-ascorbic acid palmitic acid ester. And an aqueous phase containing a powdered base material.
4) While further stirring the aqueous phase of 3) above at a low speed, gradually add medium-chain fatty acid triglyceride preheated to 60 ° C. as an oil-soluble substance, and then stir at 10000 rpm for 15 minutes with the same mixer. It was emulsified to obtain a homogenizing solution which is an oil-in-water emulsified composition.
5) The homogenizing solution of 4) above is spray-dried with a pressure nozzle type spray dryer (model: L-8i; Okawara Kakoki Co., Ltd.) under the conditions of hot air inlet temperature 170 ° C and exhaust temperature 80 ° C. The dried product was collected with a cyclone to obtain a powdered L-ascorbic acid fatty acid ester preparation 7.

(6) About L-ascorbic acid fatty acid ester preparation 8 Since the L-ascorbic acid fatty acid ester preparation 8 has only one kind of raw material, the raw material itself was used as the L-ascorbic acid fatty acid ester preparation.

[Making and evaluation of snack foods]
(1) Preparation of snack confectionery Potato flakes (product name: mash potte; manufactured by Yukiwa Foods Co., Ltd.) 600 g, potato starch (product name: potato starch; sold by Metro Cash and Carry Japan Co., Ltd.) 400 g, and the amount added as shown in Table 2 The L-ascorbic acid fatty acid ester preparation was placed in a 2 L volume polyethylene bag, and the bag with the mouth tied was held by hand and stirred for 1 minute to mix uniformly. The obtained mixture was put into a noodle making machine (model: MPC-2500; manufactured by Fuji Seiki Co., Ltd.), and while stirring, 500 g of water in which 10 g of salt was previously dissolved was added little by little, and the mixture was further stirred for 10 minutes. , The dough was prepared. After that, a tube-shaped dough (about 1 cm in diameter) extruded from the macaroni mold attached to the noodle making machine is cut into a width of 1 cm, and this is cut into frying oil at 150 to 160 ° C [palm oil (product name: refined palm oil; Miyoshi oil and fat). A mixture of rice bran oil (product name: rice salad oil; manufactured by Boseau Oil & Fat Co., Ltd.); palm oil / rice oil = 8/2 (mass ratio)] was fried for 3 minutes to obtain snacks 1 to 17.

(2) Preservation of Snack Confectionery 30 g of each of snack confectionery 1 to 17 was placed in a 100 mL polyethylene bag and sealed, and this was stored in a constant temperature bath at 60 ° C. for 5 days and 10 days, respectively.

(3) Measurement of Peroxide Value Using crushed snacks 1 to 17 as a sample, oil was extracted from the sample using diethyl ether, and the obtained oil was referred to as "reference fat analysis test method (II). The peroxide value (meq / kg) was measured based on "2.4-1996 peroxide value (chloroform method)" edited by the Japan Oil Chemists' Society. Measurements were taken immediately after the snack food was made and after storage for 5 and 10 days. The results are shown in Table 4.

(4) Sensory evaluation test The snack foods 1 to 17 stored for 10 days were eaten, and the deteriorated flavor due to the oxidation of the fats and oils contained in the snack foods was evaluated. In the test, evaluation was performed by 10 panelists according to the evaluation criteria shown in Table 3 below, and the average score was calculated and symbolized according to the following criteria. The results are shown in Table 4.
⊚: Very good average score 3.5 or more ○: Good average score 3.0 or more and less than 3.5 Δ: Slightly bad average score 2.0 or more and less than 3.0 ×: Bad average score less than 2.0

As is clear from the results in Table 4, the snack foods 1 to 12 obtained by adding the L-ascorbic acid fatty acid ester preparations 1 to 6 of the present invention have a peroxide value of 20 meq after storage at 60 ° C. for 10 days. It was suppressed to less than / kg, and the sensory evaluation was an excellent result of "○" or higher. On the other hand, snacks 13 to 16 obtained by adding L-ascorbic acid fatty acid ester preparation 7 or 8 and snacks 17 produced by adding L-ascorbic acid fatty acid ester preparation at 60 ° C. for 10 days. After storage, the peroxide value increased to 20 meq / kg or more, and the sensory evaluation was "Δ" or less, which was inferior to that of the present invention.

Claims (3)

It is a powder containing particles containing (a) L-ascorbic acid fatty acid ester and (b) fats and oils that are solid at room temperature, and L for suppressing an increase in peroxide value and / or flavor deterioration of foods and drinks. -Ascorbic acid fatty acid ester preparation. A method for producing an L-ascorbic acid fatty acid ester preparation, which comprises a step of cooling and pulverizing a melted mixture containing (a) L-ascorbic acid fatty acid ester and (b) solid fats and oils at room temperature. Mixture of (a) L-ascorbyl fatty acid ester and (b) the ratio of solid fat at room temperature [(a) / (b)] is 10 / 90-45 / 55 in mass ratio, claim 2 The method for producing an L-ascorbic acid fatty acid ester preparation according to.