JPS6312117B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a novel antioxidant for oils and fats. More specifically, the present invention relates to an antioxidant that has a long-lasting antioxidant effect on oils and fats and is completely harmless to the human body. Various natural animal and vegetable oils have been widely used in foods, medicines, cosmetics, etc., but these oils and fats can be oxidized during long-term storage, producing peroxides and causing quality deterioration. well known. Therefore, in order to prevent the oxidation of fats and oils, antioxidants such as butylhydroxyanisole, dibutylhydroxytoluene, vitamin C,
D1-α-tocopherol (vitamin E), gallic acid, nordihydroguaiaretic acid, and in some cases spices and guaiac butter are often used, but all of these antioxidants 2. Due to reasons such as insufficient antioxidant effect, lack of safety, or high price.
Although they are used in combination with one or more species, or in combination with organic acids, they are still not fully satisfactory. However, the present inventor has conducted extensive research to eliminate the above-mentioned drawbacks, provide an antioxidant that has excellent antioxidant effects on oils and fats, and is safe for the human body.As a result, the general formula: We have discovered a new fact that 3 (or 5)-oxy-γ-pyrone compounds represented by the formula (wherein R is a hydrogen atom, methyl group, or carboxyl group) are extremely effective as antioxidants for oils and fats. , we have completed the present invention. That is, the present invention uses specific 3 (or 5)-oxy-γ-pyrone compounds, namely pyromeconic acid (R is a hydrogen atom), allomaltol (R is a methyl group) and comenic acid (R is a carboxyl group) as active ingredients. This article focuses on antioxidants for oils and fats. All of these 3 (or 5)-oxy-γ-pyrone compounds have extremely low toxicity, and no abnormalities have been observed in allergy or phototoxicity tests. 3 (or 5)-oxy-γ- in the present invention
As shown in the Examples below, the pyrone compound can be used in its optimum amount as seen in other antioxidants such as vitamin E (hereinafter referred to as VE) and dibutylhydroxytoluene (hereinafter referred to as BHT) [e.g. About 0.05% for VE, and about 0.05% for BHT.
0.01%], and has the excellent advantage that its antioxidant ability improves in proportion to the amount of 3 (or 5)-oxy-γ-pyrone compound added. The blending amount can be arbitrarily selected depending on the amount, but usually 3 (or 5)
- The amount of the oxy-γ-pyrone compound to be blended is 0.05 part or more, preferably 0.1 to 100 parts of fats and oils.
If the amount of the 3 (or 5)-oxy-γ-pyrone compound is less than the above range, sufficient antioxidant effect cannot be expected, which is not preferable. Therefore, the antioxidant of the present invention can be added alone or together with other antioxidants to various foods, cosmetics, external pharmaceutical preparations, etc., and can prevent the oxidation of fats and oils contained in foods, cosmetics, external pharmaceutical preparations, etc. It is particularly effective as an antioxidant for cosmetics and external medicines. Next, the antioxidant of the present invention will be explained by giving examples and formulation examples. Example 1 3 (or 5) for each plant and animal shown in Table 1
-Oxy-γ-pyrone compounds (aromaltol,
Comenic acid, pyromeconic acid) were added to give a concentration of 0.5% and mixed uniformly. The resulting mixture was heated to 100°C and aeration was performed at a flow rate of 150 ml/min to forcibly oxidize the oil to be tested, and its peroxide value (which was released when potassium iodide was added to the sample) was measured. The amount of iodine expressed in milliequivalents per 1 kg of sample)
was measured over time. The test results are shown in Table 1. For comparison, the results were obtained when no antioxidant was added (blank), when VE was used as an antioxidant at its optimum blending amount of 0.05%, and
Table 1 also shows the case where BHT is used at its optimum blending amount of 0.01%.

【table】

[Table] Figure 1 shows the antioxidant effects of 3 (or 5)-oxy-γ-pyrone compounds (aromaltol, comenic acid, pyromeconic acid), VE, and BHT when corn oil was used as the test oil. It is shown as the change in peroxide value over time. Example 2 Changes in peroxide value over time at each concentration of comenic acid, allomaltol, and pyromeconic acid were measured in the same manner as in Example 1 when corn oil was used. The test results are shown in Figures 2-4. Similarly, the results of measuring the peroxide value at each optimum blending amount of VE and BHT and at each concentration in the vicinity are shown in FIGS. 5 and 6. As is clear from Figures 2 to 6, 3 (or 5)
-Oxy-γ-pyrone compounds show a marked decrease in their peroxide value as their concentration increases, whereas in the case of VE and BHT, their concentrations increase from 0.05% and 0.01%, respectively. It can be seen that even as the size increases, there is no significant change in their peroxide values. Formulation example 1 (External medicine) (Ointment base) Ingredients Glyceryl monostearate 4 Cethanol 0.5 Stearic acid 5 Lanolin 2 Propylene glycol 2 Liquid paraffin 3 Pyromeconic acid 0.1 Flavoring and preservative Appropriate amount Formulation example 2 (Food) (Butter) , margarine) Ingredient part Oil content 90 Glyceryl monostearate 10 Aromaltol 0.2 Edible oil (corn oil, saffron oil, salad oil, etc.) Ingredient part Oil content 80 Sorbitan sesquistearate 20 Comenic acid 0.2 (Instant ramen noodles) Ingredients Oil 15 Sorbitan monostearate 5 Aromaltol 0.05 Others 80

[Brief explanation of the drawing]

Figure 1 shows allomaltol, comenic acid, pyromeconic acid, VE and BHT as antioxidants, respectively.
Graphs showing changes in the peroxide value of corn oil over time when using comenic acid, Figures 2 to 4 are
A graph showing the change in peroxide value of corn oil over time when allomaltol and pyromeconic acid were used at various concentrations, Figure 5 is a graph similar to Figure 2 when VE was used, and Figure 6 is This is a graph similar to Figure 2 when using BHT.

Claims (1)

[Claims] 1. General formula: An antioxidant for fats and oils containing a 3 (or 5)-oxy-γ-pyrone compound represented by the formula (wherein R is a hydrogen atom, a methyl group, or a carboxyl group) as an active ingredient.