JPH0227389B2 - KOSANKAZAINOSEIZOHO - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a method for producing an antioxidant using licorice as a raw material. Antioxidants that are added to oils and fats that are easily oxidized by oxygen in the air, as well as various foods and cosmetics that contain them, have traditionally been synthetic products such as dibutylhydroxytoluene (BHT), butylhydroxyanisole (BHA), and Natural products such as tocopherols and spice extracts are used.
However, although synthetic products have strong antioxidant power, their use is restricted due to safety issues, and BHA in particular has recently been completely banned from being added to oils and fats other than palm oil. It came to this. Natural products are said to be relatively safe, but tocopherols are inferior to synthetic products in terms of stability in food and antioxidant power, and spice extracts have excellent antioxidant power. However, because it has a unique aroma, it cannot be used for anything other than foods that can benefit from its flavor. On the other hand, it is also known that components extracted from the roots of licorice roots with water, ethanol, or ether exhibit antioxidant properties. (Journal of Japan Food Industry Association; Volume 25,
No. 25, 1978). However, water or ethanol extracts of licorice contain sweet glycyrrhizin and sugars, so they cannot be used as general antioxidants unless these are removed. Ether extracts do not have these drawbacks, but ether extraction is difficult to perform on an industrial scale due to ether's flammability, explosiveness, anesthetic properties, etc., so it has yet to be put into practical use. do not have. In contrast, the present inventors have discovered that when licorice is extracted using an organic compound selected from the group consisting of methylene chloride, chloroform, ethyl acetate, n-propyl acetate, n-butyl acetate, and isobutyl acetate as an extraction solvent, They discovered that a substance that is tasteless and odorless and exhibits extremely strong antioxidant power can be extracted, leading to the completion of the present invention, which features the above-mentioned extraction method. Licorice (especially its root), which is used as a raw material in the production method of the present invention, has been used as a medical raw material since ancient times.
The water-extracted extract is also used as an additive for soybean oil, miso, etc. The raw material licorice in the present invention can be the same as the licorice normally used for these purposes,
It doesn't require anything special. Further, the residue after extracting glycyrrhizin from licorice using neutral or slightly alkaline water can also be used as a raw material for the production method of the present invention. The process of extracting antioxidant substances from licorice or its glycyrrhizin extraction residue does not require any special extraction conditions, other than using the above-mentioned extraction solvent. Only very limited solvents have the ability to selectively extract antioxidant substances from licorice, and the commonly used solvents such as toluene, benzene, and
- With hydrocarbon solvents such as hexane and petroleum ether, almost no antioxidants are extracted, and the antioxidant power of the extract is extremely weak. In addition, lower alcohols and lower ketones extract glycyrrhizin and other flavor components along with antioxidant substances.
The resulting extract not only has poor antioxidant power but also has a strong sweet taste, and its range of use is extremely limited unless the flavor components are removed. Extraction is performed by immersing the raw material to be treated in about 3 times the amount of the solvent and heating it under reflux, or by immersing the raw material in about 5 times the amount of the solvent at room temperature. These operations are
It is desirable to repeat these two or three times individually or in combination. After removing solid substances such as dust from the obtained extract by filtration or centrifugation, the extraction solvent is distilled off using an appropriate method to obtain a light brown, tasteless and odorless substance that has antioxidant properties. This substance can be used as an antioxidant for many purposes as it is, but if necessary, it may be subjected to purification treatment such as decolorization to the extent that its antioxidant power is not impaired before being used as an antioxidant. You can also use it as The appropriate amount to be used is about 0.005 to 0.05% by weight based on the fats and oils. When used, it may be used by adding an appropriate excipient and forming it into granules, or it may be used by dissolving it in oil, propylene glycol, glyceric acid monostearate, etc., or a mixture thereof. The antioxidant obtained by the method of the present invention is
Demonstrates excellent antioxidant power comparable to BHT.
Moreover, since it is oil-soluble and, as mentioned above, tasteless and odorless, it dissolves evenly and well even when mixed directly into fats and oils, significantly improving stability without impairing the original flavor of the fats and oils. be able to. Examples of fats and oil-containing foods that can be stabilized using the antioxidant obtained by the method of the present invention include fish oil, lard, tallow, het,
Chicken oil, soybean oil, linseed oil, cottonseed oil, safflower oil, rice oil, corn oil, coconut oil, palm oil,
Sesame oil, cacao oil, castor oil, peanut oil, butter, cheese, margarine, toning, mayonnaise, dressing, ham, sausage, potato chips, fried rice crackers, fried ramen, curry roux, etc. The antioxidant produced by the method of the present invention can also be added to oils and fats used in various oil-containing cosmetics such as creams, emulsions, and hair styling products to stabilize them and prevent accidents such as skin disorders caused by oil and fat oxides. It is extremely effective. The present invention will be explained below with reference to Examples and Test Examples. Example 1 Add 2 kg of crushed licorice root to 10 ml of ethyl acetate at room temperature.
After soaking for a time to extract the ethyl acetate soluble components,
The extract and the extraction residue were separated by filtration. The same operation was repeated two more times to obtain a total of 30 extracts. The solvent of the extract was distilled off, and the remaining solid matter was dried under reduced pressure and pulverized to obtain 72 g of a light brown powder having antioxidant power (hereinafter referred to as antioxidant A). Example 2 After extracting glycyrrhizin by soaking 1 kg of licorice root in 1% aqueous ammonia, the extraction residue was dried.
This was heated under reflux with methylene chloride from step 3 for 2 hours to extract the methylene chloride soluble components.
The same operation was repeated for the extract and the separated extraction residue to obtain a total of 6 extracts. After that, the solvent of the extract was distilled off, and the extract was further dried under reduced pressure.
Light brown powder with antioxidant power (hereinafter referred to as antioxidant B)
) 25g was obtained. Test Example 1 The AOM test method was applied to purified lard containing no antioxidants to which 0.02% by weight of antioxidants A, B, tocopherol (purity 70%) or synthetic antioxidant BHT purified in the above example was added. The performance of each antioxidant was compared by measuring the time T ₂₀ until the peroxide value (POV) reached 20. The results are shown in Table 1. Table 1 Antioxidant T ₂₀ [Hr] A 20 B 22 Tocopherol 13 BHT 22 Additive-free 3 Test Example 2 The same procedure as in Test Example 1 was carried out for the extract obtained in the same manner as in Example 2 except that the extraction solvent was changed. Antioxidant power was tested using the method. Table 2 shows the results.
Shown below. In the same table, the first seven examples are control examples conducted on extracts obtained using a solvent different from the solvent used in the present invention. Table 2 Extract solvent T ₂₀ [HR] petroleum ether 3.0 N -hexane 3.5 cyclohexan 4.0 toruhexan 5.0 methanol 5.0 acetone 5.2 chlorofolm 22.0 chlorofolm2.0 N -prophlum 21.0 n -butylpille 21.0 isobutille 21.0 Test 3 Lard, palm oil, etc. 0.02% of antioxidant B according to Example 2 was added to the mixture, and the mixed oil was heated to 145%.
200g of ramen noodles heated to ±5°C and formed were fried for 2 minutes. Separately, as a control product, fried ramen noodles were produced in the same manner as above, except that no antioxidant was added or tocopherol (purity 70%) or BHT was used instead. Immediately after production, each fried ramen was sealed in a polypropylene film bag and stored at 50°C. A portion of the fried ramen immediately after production, and 40 and 80 days after storage was taken, the oil and fat content was extracted with ethyl ether, and the peroxide value was measured according to a modified version of the Rhea method. The results are shown in Table 3.

[Table] Test example 4 Pork (minced meat) 2.4Kg, pork fat (shredded) 1.2Kg,
70g of common salt, 1g of sodium nitrite, 5g of sugar, 5g of grain koshiyo, 20g of grape wine, and 0.7g of the antioxidant A from Example 1 were mixed and filled into a casing with a diameter of 3cm, and dried at 5°C for 30 days to make salami. produced sausages. Separately, a control product was produced in the same manner as above except that antioxidant A was not added. We conducted a sensory test on the flavor of these sausages, and found that while the control product felt oily, the product with antioxidant A had no such effect.
Moreover, no unpleasant taste due to the addition of antioxidants was felt.

Claims (1)

[Claims] 1 Extracting the residue obtained by extracting glycyrrhizin from licorice or licorice using an organic solvent selected from the group consisting of methylene chloride, chloroform, ethyl acetate, n-propyl acetate, n-butyl acetate, and isobutyl acetate as an extraction solvent, A method for producing an antioxidant, which comprises collecting extracted licorice components from an extract.