antioxidant preparations

Abstract

To provide an antioxidant formulation that has an increased level of L-ascorbic acid or the like with its dispersibility being improved.SOLUTION: An antioxidant formulation contains L-ascorbic acid fatty acid ester, oil-based substance, and sucrose-mixed fatty acid ester. The content of the L-ascorbic acid fatty acid ester is 13 mass% or more relative to the total mass of the antioxidant formulation.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to an antioxidant preparation. More specifically, the present invention relates to an antioxidant preparation containing a high content of L-ascorbic acid fatty acid esters. [Background technology]

[0002] L-ascorbic acid (also known as vitamin C) has a strong reducing effect and is added to many foods as a water-soluble antioxidant, and is used as a safe and nutritional supplement. L-ascorbic acid derivatives, such as L-ascorbic acid fatty acid esters, are also used as antioxidants because they have the same strong reducing effect as L-ascorbic acid. Depending on the application of L-ascorbic acid and its derivatives (hereinafter referred to as "L-ascorbic acid, etc."), enhanced antioxidant function is required. For example, in the case of fried foods, enhanced antioxidant performance is required to maintain the crispy, freshly fried texture and color of the food. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] International Publication No. 2018 / 190203 Summary of the Invention [Problem to be solved by the invention]

[0004] However, when attempting to increase the amount of antioxidants such as L-ascorbic acid, the L-ascorbic acid settled and separated in the oil phase, preventing it from dispersing well in the oil phase. Adding an emulsifier and then shearing with a high-pressure homogenizer solved the problem by dispersing the L-ascorbic acid, etc. However, shearing with a high-pressure homogenizer created the problem of an increase in the viscosity of the oil phase. Since the increase in viscosity can cause pipe clogging, an improvement was needed.

[0005] For these reasons, there has been a demand for both strengthening the antioxidant function of antioxidant preparations and improving the dispersibility of L-ascorbic acid, etc. An object of the present invention is to provide an antioxidant preparation that can achieve both high concentration and good dispersibility of L-ascorbic acid or the like. [Means for solving the problem]

[0006] <1> An antioxidant preparation comprising an L-ascorbic acid fatty acid ester, an oily substance, and a sucrose mixed fatty acid ester, wherein the content of the L-ascorbic acid fatty acid ester is 13 mass% or more based on the total mass of the antioxidant preparation. <2> The antioxidant preparation according to <1>, wherein the mixed fatty acid portion of the sucrose mixed fatty acid ester is composed of oleic acid, palmitic acid, and stearic acid. <3> The antioxidant preparation according to <1> or <2>, wherein the content of the L-ascorbic acid fatty acid ester is 16 mass% or more based on the total mass of the antioxidant preparation. <4> The antioxidant preparation according to <1> or <2>, wherein the content of the L-ascorbic acid fatty acid ester is 20 mass% or more based on the total mass of the antioxidant preparation. <5> The antioxidant preparation according to any one of <1> to <4>, wherein the L-ascorbic acid fatty acid ester is L-ascorbic acid palmitate. <6> The antioxidant preparation according to any one of <1> to <5>, wherein the particle size of the antioxidant preparation is 1200 nm or less as measured by ELSZ. <7> The antioxidant preparation according to any one of <1> to <6>, wherein the antioxidant preparation has a viscosity of 1000 mPa·s or less according to the Standard Oil and Fat Analysis Method. <8> The antioxidant preparation according to <7>, wherein the content of the sucrose mixed fatty acid ester is 4 mass% or more based on the total mass of the antioxidant preparation. <9> The antioxidant preparation according to <7>, wherein the content of the sucrose mixed fatty acid ester is 8% by mass or more based on the total mass of the antioxidant preparation. <10> The antioxidant preparation according to any one of <1> to <9>, wherein the oily substance is at least one selected from the group consisting of rapeseed oil, soybean oil, corn oil, rice oil, olive oil, sesame oil, safflower oil, sunflower oil, peanut oil, almond oil, cottonseed oil, fish oil, whale oil, shark oil, fish liver oil, mink oil, avocado oil, jojoba oil, lard, squalene, medium-chain fatty acid triglycerides, vitamins A, D and E, and derivatives thereof. <11> The antioxidant preparation according to any one of <1> to <10>, further comprising a surfactant. <12> The antioxidant preparation according to <11>, wherein the surfactant is at least one selected from the group consisting of glycerin fatty acid esters, sucrose fatty acid esters, sorbitan fatty acid esters, propylene glycol fatty acid esters, saponins, and sterols. [Effects of the Invention]

[0007] According to the present invention, there is provided an antioxidant preparation that can achieve both high concentration and good dispersibility of L-ascorbic acid or the like. [Brief explanation of the drawings]

[0008] [Figure 1] FIG. 1 is a diagram showing the dispersion state of L-ascorbyl palmitate in triglyceride in the antioxidant preparation of Example 1 at room temperature. [Figure 2] 2A, 2B, and 2C are diagrams showing the dispersion state of L-ascorbyl palmitate in triglycerides at room temperature in the antioxidant preparations of Examples 1, 2, and 3, respectively. [Figure 3] FIG. 3 is a diagram showing the dispersion state of L-ascorbyl palmitate in triglyceride at room temperature in the antioxidant preparation of Comparative Example 1. [Figure 4] 4A and 4B are diagrams showing the dispersion state of L-ascorbyl palmitate in triglyceride at room temperature in the antioxidant preparations of Comparative Examples 1 and 2, respectively. DETAILED DESCRIPTION OF THE INVENTION

[0009] The present invention will be described below with reference to embodiments, but the present invention is not limited to the following embodiments.

[0010] The present invention relates to an antioxidant preparation comprising an L-ascorbic acid fatty acid ester, an oily substance, and a sucrose mixed fatty acid ester, wherein the content of the L-ascorbic acid fatty acid ester is 13 mass% or more based on the total mass of the antioxidant preparation. The content of the L-ascorbic acid fatty acid ester is preferably 16% by mass or more, more preferably 20% by mass or more, based on the total mass of the antioxidant preparation.

[0011] It is preferable that the particle size of the antioxidant preparation is 1200 nm or less as measured using ELSZ (zeta potential / particle size / molecular weight measurement system, manufactured by Otsuka Electronics Co., Ltd., product name "ELSZ-2000ZS"). It is also preferable that the viscosity of the antioxidant preparation be 1000 mPa·s or less according to the Standard Fats and Oils Analysis Method.

[0012] According to the present invention, by using a sucrose mixed fatty acid ester as an emulsifier, it is possible to achieve both high concentration and dispersibility of L-ascorbic acid, etc. The antioxidant preparation will be described in detail below.

[0013] L-ascorbic acid fatty acid esters are monoesters, diesters, triesters, etc., of L-ascorbic acid and fatty acids. Examples of the acid moiety of the ester include lauric acid, myristic acid, palmitic acid, stearic acid, arachidonic acid, behenic acid, cerotic acid, oleic acid, linoleic acid, docosahexaenoic acid, and eicosapentaenoic acid. Among these, L-ascorbic acid palmitate and L-ascorbic acid stearate are particularly preferred, with L-ascorbic acid palmitate being the most preferred. Due to its smaller molecular weight, L-ascorbic acid palmitate has a slightly higher effect than L-ascorbic acid stearate when added in the same amount.

[0014] The L-ascorbic acid fatty acid ester may be selected from the above group and used alone, or two or more may be used in combination. The amount of L-ascorbic acid fatty acid ester is preferably 0.1 to 70% by mass, more preferably 1 to 30% by mass, and even more preferably 5 to 25% by mass, based on the total mass of the antioxidant preparation. To exhibit an effective antioxidant effect, 0.1% by mass or more is required, and to produce a fluid liquid, 70% by mass or less is preferred.

[0015] The oily substance is an oily substance that is liquid at room temperature, and includes animal and vegetable oils, hydrocarbons, vitamins, medium-chain fatty acid triglycerides, etc. Specific examples of animal and vegetable oils include rapeseed oil, soybean oil, corn oil, rice oil, olive oil, sesame oil, safflower oil, sunflower oil, peanut oil, almond oil, cottonseed oil, fish oil, whale oil, shark oil, fish liver oil, mink oil, avocado oil, jojoba oil, and lard. Examples of hydrocarbons include squalene. Medium-chain fatty acid triglycerides are single or mixtures of triglycerides having a fatty acid group with any carbon number ranging from 6 to 24. Examples of vitamins include vitamins A, D, and E and their derivatives. Among these, rapeseed oil and medium-chain fatty acid triglycerides are particularly preferred.

[0016] Instead of oily substances, solvents such as glycerin and propylene glycol can also be used.

[0017] The oily substance may be selected from the above group and used alone, or two or more may be used in combination. The amount of the oily substance used is preferably 30 to 99.9% by mass, more preferably 60 to 98% by mass, based on the total mass of the antioxidant preparation. To uniformly disperse the L-ascorbic acid fatty acid ester, the amount of the oily substance used is preferably within the above range.

[0018] Sucrose mixed fatty acid esters are diesters, triesters, etc., composed of sucrose and mixed fatty acids. Examples of the acid moiety of the ester include lauric acid, myristic acid, palmitic acid, stearic acid, arachidonic acid, behenic acid, cerotic acid, oleic acid, linoleic acid, docosahexaenoic acid, and eicosapentaenoic acid. The sucrose mixed fatty acid ester is preferably a triester, and more preferably, the mixed fatty acid moiety is composed of oleic acid, palmitic acid, and stearic acid.

[0019] The content of the sucrose mixed fatty acid ester is preferably 4% by mass or more, more preferably 8% by mass or more, based on the total mass of the antioxidant preparation.

[0020] An emulsifier (surfactant) can be added to the antioxidant preparation. The addition of an emulsifier can stabilize the dispersion state of the dispersion. Preferred emulsifiers are nonionic surfactants and amphoteric surfactants. Specific examples of nonionic surfactants include glycerin fatty acid esters, sucrose fatty acid esters, sorbitan fatty acid esters, propylene glycol fatty acid esters, saponin, and sterols. Among these, glycerin fatty acid esters, sucrose fatty acid esters, and sorbitan fatty acid esters are particularly preferred. Although lecithins such as lecithin, enzyme-treated lecithin, and enzyme-degraded lecithin do not cause browning if used in very small amounts, it is preferable not to use them.

[0021] The emulsifier may be one selected from the above group, or two or more may be mixed and used. The amount of surfactant used is preferably 20% by mass or less, more preferably 1 to 10% by mass, based on the total mass of the antioxidant formulation. Even if more than 20% by mass is used, an increase in the amount does not result in an increase in the effect as a dispersant.

[0022] A single fatty acid can be used as the emulsifier. The single fatty acid may be any of the fatty acids listed as the acid moiety of the ester in the section on sucrose mixed fatty acid esters above. In this case, one type may be selected and used, or two or more types may be mixed and used. Among these, it is preferable to select from the group consisting of oleic acid, palmitic acid, and stearic acid. The term "mixed fatty acids" includes (1) the group of fatty acids that make up the acid portion of sucrose mixed fatty acid esters, (2) the group of single fatty acids used as emulsifiers in combination with sucrose mixed fatty acid esters, and (3) the group of fatty acids that combines the above-mentioned (1) and (2). The combinations of each group of fatty acids are independent of each other.

[0023] Next, a method for producing an antioxidant preparation will be described, but is not limited to the following example. The emulsifier is added to the oily substance, and the mixture is heated to 55-65°C. The temperature is maintained while stirring, dissolving the emulsifier in the oily substance. While cooling the resulting solution, L-ascorbic acid palmitate is added, and the mixture is stirred for approximately 15 minutes using a homomixer. After stirring, the solution is cooled until its temperature reaches 20°C. This produces an antioxidant formulation.

[0024] Alternatively, it can be produced by the following method.

[0025] An emulsifier and an L-ascorbic acid fatty acid ester are dissolved in an oily substance heated to 70 to 80°C, and the mixture is cooled while being thoroughly stirred with a homomixer to give the antioxidant preparation of the present invention.

[0026] The antioxidant preparation of the present invention obtained by the above-mentioned production method is a fluid, cloudy liquid with a viscosity in the range of approximately 100 to 3000 cp, although this varies somewhat depending on the concentration of the L-ascorbic acid fatty acid ester to be mixed.

[0027] The antioxidant preparation can be easily incorporated into fats and oils and foods containing fats and oils by mixing and stirring. Alternatively, the antioxidant preparation can be incorporated into food ingredients during the food production process by kneading it. A preferred amount is, for example, 0.1 to 0.5% by mass of the edible oil.

[0028] When antioxidant preparations are added alone to oils and fats, oil-containing foods, or food ingredients, etc., they have the same effect as powdered L-ascorbic acid fatty acid esters, provided that the final amount added is the same. Furthermore, when used in combination with other antioxidant preparations, the effect is synergistically enhanced.

[0029] The antioxidant preparation does not solidify or lose its fluidity even when stored at temperatures as low as 0°C. Furthermore, when stored in a dark place at room temperature, there is no loss of L-ascorbic acid fatty acid esters for at least six months.

[0030] The antioxidant preparation can be added to cosmetics, medicines, feeds, etc. in addition to foods.

[0031] (Other embodiments) As described above, the present invention has been described by way of the embodiments, but the statements that form part of this disclosure should not be understood as limiting the present invention. From this disclosure, various alternative embodiments, examples, and operating techniques will become apparent to those skilled in the art. In addition to the antioxidant preparation, the present invention also relates to foods, such as fried foods, that use the antioxidant preparation. According to the present invention, the antioxidant function is enhanced, so that fried foods can be obtained that retain a crispy, freshly fried feel and maintain their color even after being left for a predetermined period of time. As such, the present invention naturally includes various embodiments not described herein. Therefore, the technical scope of the present invention is defined only by the invention-specifying matters according to the scope of the claims that are appropriate from the above description.

[0032] The present invention will be explained in more detail below with reference to examples, but is not limited to these. [Example]

[0033] Example 1 (antioxidant preparation) An antioxidant formulation was prepared according to the following recipe. L-Ascorbic acid palmitate 20% by mass Sucrose mixed fatty acid ester 4% by mass Triglycerides 76% by mass A sucrose mixed fatty acid ester (manufactured by Mitsubishi Chemical Foods Corporation, product name "Ryoto Sugar Ester POS-135") consisting of sucrose and mixed fatty acids (oleic acid, palmitic acid, and stearic acid) was added to the triglyceride, and the mixture was heated to 60°C and stirred continuously to dissolve the sucrose mixed fatty acid ester in the triglyceride. While cooling the resulting solution with tap water, L-ascorbyl palmitate was added thereto, and the mixture was stirred at 3,000 rpm for 15 minutes using a homomixer. After stirring, the solution was cooled with tap water until the temperature of the solution reached 20°C. In this way, the antioxidant preparation of Example 1 was obtained.

[0034] (dispersed state) The dispersion state of L-ascorbic acid palmitate in the triglyceride was visually observed at room temperature for the obtained antioxidant preparation of Example 1. The obtained results are shown in FIG. As shown in FIG. 1, it was observed that L-ascorbyl palmitate particles were dispersed finely and uniformly throughout the triglyceride, so that no particles were visible to the naked eye, and the triglyceride was opaque.

[0035] (viscosity) The obtained antioxidant preparation of Example 1 was homogenized using a high-pressure homogenizer, and then the viscosity of the antioxidant preparation was measured according to the standard method for analyzing fats and oils. As a result, the viscosity of the antioxidant formulation was 1235 mPa·s. The dispersion state of L-ascorbyl palmitate in triglyceride was visually observed at room temperature, and the results are shown in Figure 2A.

[0036] (dispersibility) The particle size of the antioxidant preparation was measured using ELSZ (zeta potential, particle size, and molecular weight measurement system, manufactured by Otsuka Electronics Co., Ltd., product name "ELSZ-2000ZS"). As a result, the particle size of the antioxidant preparation was 1041.0 nm.

[0037] According to Example 1, an antioxidant preparation containing a high content of L-ascorbic acid fatty acid esters and in which the L-ascorbic acid fatty acid esters were uniformly dispersed was obtained.

[0038] <Example 2> (antioxidant preparation) Antioxidant preparations were prepared in the same manner as in Example 1, except that the amount of sucrose mixed fatty acid ester added was changed as follows. L-Ascorbic acid palmitate 20% by mass Sucrose mixed fatty acid ester 8% by mass Triglycerides 72% by mass The obtained antioxidant preparation was subjected to the same procedures as in Example 1 to observe the dispersion state of L-ascorbic acid palmitate in the triglyceride and to measure the viscosity of the antioxidant preparation. (dispersed state) As a result, similar to Example 1, it was observed that L-ascorbic acid palmitate particles were dispersed finely and uniformly throughout the triglyceride to the extent that no particles were visible, and the triglyceride was opaque. (viscosity) The viscosity of the antioxidant formulation was 532 mPa·s. The dispersion state of L-ascorbyl palmitate in triglyceride was visually observed at room temperature, and the results are shown in Figure 2B.

[0039] (dispersibility) The particle size of the antioxidant preparation was measured using the ELSZ described above. As a result, the particle size of the antioxidant preparation was 902.2 nm.

[0040] Example 3 (antioxidant preparation) Antioxidant preparations were prepared in the same manner as in Example 1, except that the amount of sucrose mixed fatty acid ester added was changed as follows. L-Ascorbic acid palmitate 20% by mass Sucrose mixed fatty acid ester 12% by mass Triglycerides 72% by mass The obtained antioxidant preparation was subjected to the same procedures as in Example 1 to observe the dispersion state of L-ascorbic acid palmitate in the triglyceride and to measure the viscosity of the antioxidant preparation. (dispersed state) As a result, similar to Example 1, it was observed that L-ascorbic acid palmitate particles were dispersed finely and uniformly throughout the triglyceride to the extent that no particles were visible, and the triglyceride was opaque. (viscosity) The viscosity of the antioxidant formulation was 425 mPa·s. The dispersion state of L-ascorbyl palmitate in triglyceride was visually observed at room temperature, and the results are shown in Figure 2C.

[0041] (dispersibility) The particle size of the antioxidant preparation was measured using the ELSZ described above. As a result, the particle size of the antioxidant preparation was 854.4 nm.

[0042] <Comparative Example 1> (antioxidant preparation) An antioxidant preparation was prepared in the same manner as in Example 1, except that the sucrose mixed fatty acid ester was replaced with sucrose stearate (manufactured by Mitsubishi Chemical Foods Corporation, trade name "Ryoto Sugar Ester S-170") and the mass ratio was changed. L-Ascorbic acid palmitate 20.25% by mass Sucrose stearate 4% by mass Triglycerides 75.75% by mass

[0043] (dispersed state) The resulting antioxidant preparation was visually observed at room temperature to determine the state of dispersion of L-ascorbyl palmitate in the triglyceride. The results are shown in Figure 3. The dispersion state of L-ascorbyl palmitate in triglyceride was visually observed at room temperature, and the results are shown in Figure 3. As shown in FIG. 3, it was visually observed that particles of L-ascorbyl palmitate were dispersed throughout the triglyceride, and the triglyceride was opaque.

[0044] (viscosity) The obtained antioxidant preparation of Comparative Example 1 was homogenized with a high-pressure homogenizer, and then the viscosity of the antioxidant preparation was measured according to the standard method for analyzing fats and oils. The viscosity of the antioxidant formulation was 1235 mPa·s. The dispersion state of L-ascorbyl palmitate in triglyceride was visually observed at room temperature, and the results are shown in Figure 4A.

[0045] (dispersibility) The particle size of the antioxidant preparation was measured using the ELSZ described above. As a result, the particle size of the antioxidant preparation was 1453.2 nm.

[0046] <Comparative Example 2> (antioxidant preparation) An antioxidant preparation was prepared in the same manner as in Example 1, except that the sucrose mixed fatty acid ester was replaced with sucrose stearate (manufactured by Mitsubishi Chemical Foods Corporation, trade name "Ryoto Sugar Ester S-170") and the mass ratio was changed. L-Ascorbic acid palmitate 20.25% by mass Sucrose stearate 8% by mass Triglycerides 71.75% by mass

[0047] The obtained antioxidant preparation was subjected to the same procedures as in Example 1 and Comparative Example 1 to observe the dispersion state of L-ascorbic acid palmitate in the triglyceride and to measure the viscosity of the antioxidant preparation. (dispersed state) As a result, similarly to Comparative Example 1, particles of L-ascorbic acid palmitate were observed to be dispersed throughout the triglyceride, and the triglyceride was opaque. (viscosity) The viscosity of the antioxidant formulation was 1186 mPa·s. The dispersion state of L-ascorbyl palmitate in triglyceride was visually observed at room temperature, and the results are shown in Figure 4B.

[0048] (dispersibility) The particle size of the antioxidant preparation was measured using the ELSZ described above. As a result, the particle size of the antioxidant preparation was 1393.1 nm.

[0049] The results of Examples 1 to 3 and Comparative Examples 1 and 2 showed that even when the L-ascorbyl palmitate content was as high as 20% by mass, the use of a sucrose mixed fatty acid ester as an emulsifier improved the dispersibility of L-ascorbyl palmitate in triglycerides. It was also shown that the use of a sucrose mixed fatty acid ester made it possible to achieve both a high concentration and good dispersibility of L-ascorbyl palmitate. The results of Examples 1 to 3 showed that when a sucrose mixed fatty acid ester is used as an emulsifier, the viscosity of the antioxidant preparation is reduced and the flowability is improved when the content is 8% by mass or more. [Industrial Applicability]

[0050] Despite its high content of L-ascorbic acid palmitate, the antioxidant preparation exhibits good dispersibility. Therefore, by adding the antioxidant preparation to frying oil, L-ascorbic acid palmitate is present in high concentrations with good dispersibility, effectively inhibiting oxidation of fried foods. Furthermore, because the antioxidant preparation contains a higher content of L-ascorbic acid palmitate than conventional preparations, the antioxidant preparation can be added to frying oil less frequently. Furthermore, the antioxidant preparation has low viscosity in addition to dispersibility, and therefore can be used in the form of a spray. Therefore, by spraying the antioxidant preparation onto fried foods as a color-fixing agent, color fixation of the fried foods can be effectively prevented.

Claims

1. L-ascorbic acid palmitate, An oily substance; and a sucrose mixed fatty acid ester, the mixed fatty acid portion of the sucrose mixed fatty acid ester is composed of oleic acid, palmitic acid, and stearic acid; The content of each component based on the total mass of the antioxidant preparation is: The content of the L-ascorbic acid palmitate is 13% by mass or more and 30% by mass or less, The content of the sucrose mixed fatty acid ester is 4% by mass or more, The remainder of the antioxidant preparation is the oily substance.

2. 2. The antioxidant preparation according to claim 1, wherein the content of the L-ascorbyl palmitate is 16% by mass or more based on the total mass of the antioxidant preparation.

3. 2. The antioxidant preparation according to claim 1, wherein the content of the L-ascorbyl palmitate is 20% by mass or more based on the total mass of the antioxidant preparation.

4. The antioxidant preparation according to any one of claims 1 to 3, wherein the content of the sucrose mixed fatty acid ester is 4% by mass or more and 8% by mass or less.

5. An antioxidant preparation according to any one of claims 1 to 3, wherein the content of the sucrose mixed fatty acid ester is 8% by mass or more.

6. The antioxidant preparation according to any one of claims 1 to 5, wherein the particle size of the antioxidant preparation is 1200 nm or less as measured by ELSZ.

7. The antioxidant preparation according to any one of claims 1 to 5, wherein the antioxidant preparation has a viscosity of 1000 mPa·s or less, as measured by the Standard Oil and Fat Analysis Method.

8. The antioxidant preparation according to any one of claims 1 to 7, wherein the oily substance is one or more selected from the group consisting of rapeseed oil, soybean oil, corn oil, rice oil, olive oil, sesame oil, safflower oil, sunflower oil, peanut oil, almond oil, cottonseed oil, fish oil, whale oil, shark oil, fish liver oil, mink oil, avocado oil, jojoba oil, lard, squalene, medium-chain fatty acid triglycerides, vitamins A, D and E, and derivatives thereof.

9. The antioxidant preparation according to any one of claims 1 to 8, further comprising a surfactant.

10. 10. The antioxidant preparation according to claim 9, wherein the surfactant is at least one selected from the group consisting of glycerin fatty acid esters, sucrose fatty acid esters, sorbitan fatty acid esters, propylene glycol fatty acid esters, saponins, and sterols.

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