JP2630949B2 - Tasteless and odorless method for substances with high amino acid content - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION (Industrial application field) The present invention relates to a method for deodorizing a substance containing a high content of amino acids in a tasteless and odorless manner.

Since the amino acid-rich substance treated by the method of the present invention is tasteless and odorless, it can be used as a raw material for various foods and pharmaceuticals (solid or liquid amino acid preparations, supplemental nutrition, etc.).

(Prior Art) In the process of producing a brew using soy as a raw material, substances containing various amino acids at high concentrations are by-produced.

This amino acid-rich substance, particularly an amino acid mixture containing a large amount of leucine, has a peculiar unpleasant odor and unpleasant taste (bitterness). Therefore, when this substance is used as it is, focusing on the nutritional value, for example, when an amino acid preparation is produced, masking, that is, flavoring and smelling must be performed.

On the other hand, as a purification method for removing the unpleasant odor and unpleasant taste of the amino acid-rich substance and obtaining a leucine-rich substance, a method for removing tyrosine from a leucine mixture (JP-A-49-85019), Fractional crystallization from an aqueous solution containing isoleucine and valine (Japanese Patent Application Laid-Open No. 56-1645)
0), fractional crystallization by acetylation (JP-A-60-415)
5), a method using a special precipitant (Japanese Patent Publication No. 56-10907 and
10908), and a fractional crystallization method from an aqueous solution containing leucine and isoleucine (Japanese Patent Publication No. 56-38583).

(Problems to be Solved by the Invention and Object of the Invention) The above-mentioned various methods that have been conventionally proposed for deodorizing a substance having a high amino acid content require expensive reagents and apparatuses when performing the method. Therefore, although the raw material itself can be obtained inexpensively and abundantly, there is a problem in that the cost of a final product such as a leucine-rich substance increases.

Thus, an object of the present invention is to provide a method for making a substance containing a high amount of amino acid tasteless and odorless, which does not require expensive reagents, is simple in operation, and can minimize an increase in cost. It is in.

(Means and Actions for Solving the Problems and Achieving the Object) According to the present invention, the above problems are characterized in that an oxidizing agent is allowed to act on a substance having a high amino acid content, and then the oxidizing agent is removed. The problem is solved by a method for deodorizing and deodorizing a substance having a high amino acid content, and the above object is achieved.

The high-amino acid-containing substance to be treated in the method of the present invention can be a by-product in the brewing industry using soybean as a raw material, particularly an amino acid mixture containing a large amount of leucine as described above. . The oxidizing agent may be an inorganic oxidizing agent or an organic oxidizing agent. Examples of the inorganic oxidizing agent include hydrogen peroxide, and examples of the organic oxidizing agent include acetic acid, acetic acid and acetate, N- Examples thereof include chlorosuccinimide, chloramine T, and trichloromethanesulfonyl chloride. The effect of the oxidizing agent on the amino acid-rich substance is 0.0001-10 of the amino acid-rich substance.
It is preferable to add 0.0000001 to 80% by weight of the oxidizing agent to the solution by weight and react at a temperature within the temperature range of room temperature to 200 ° C. When acetic acid or acetic acid and acetate are used, ultraviolet irradiation is performed. The time required for the reaction depends on the type of the oxidizing agent used, the temperature conditions and the like, but is about several minutes to 48 hours. The subsequent removal of the oxidizing agent is carried out by any one or a combination of powdering treatments such as evaporation to dryness, freeze drying, spray drying and the like, solvent washing treatment and enzyme treatment. It is selected in consideration of the type. For example, when an inorganic oxidizing agent is selected, powdering treatment is often sufficient, and when an organic oxidizing agent is selected, after the powdering treatment, further treatment is performed using a solvent such as water, alcohol, or an aqueous alcohol solution. Is preferred.
When hydrogen peroxide is used as the oxidizing agent, it can be decomposed by catalase which is a specific decomposing enzyme.

(Examples) Next, the present invention will be described in more detail with reference to Examples, Amino Acid Composition Ratio Measurement-Sensory Test Examples, Formulation Examples as Application Examples, and Supplemental Nutrition Food Production Examples.

Example 1 An amino acid-rich substance (60 g) was dissolved in 3000 ml of purified water. 30 ml of 30% aqueous hydrogen peroxide was added to this solution, stirred, left to stand for 2 hours, and spray-dried at an intake temperature of 150 to 160 ° C and an exhaust temperature of 55 to 60 ° C to obtain a powder. 50g of this powder
Then, 1000 ml of a 70% aqueous ethanol solution was added thereto, and the mixture was stirred for 30 minutes, filtered by suction, and washed with 1000 ml of absolute ethanol. The residue was dissolved in 2000 ml of purified water, and the inlet air temperature was 150-160 ° C.
The desired substance was obtained as a powder by performing spray drying at an exhaust temperature of 55-60 ° C (yield: 65%).

Example 2 60 g of an amino acid-rich substance was dissolved in 3000 ml of purified water. After adding 150 ml of acetic acid to this solution and stirring,
UV light was applied for 5 hours. The obtained solution was spray-dried at an intake temperature of 150 to 160 ° C and an exhaust temperature of 55 to 60 ° C to obtain a desired substance as a powder (yield: 9).
1%).

Example 3 60 g of an amino acid-rich substance was dissolved in 3000 ml of purified water. After adding 70 ml of acetic acid and 70 g of ammonium acetate to the solution and stirring, the mixture was irradiated with ultraviolet rays for 5 hours. The obtained solution was spray-dried at an intake temperature of 150 to 160 ° C and an exhaust temperature of 55 to 60 ° C to obtain a desired substance as a powder (yield: 90%).

Example 4 An amino acid-rich substance (60 g) was dissolved in 3000 ml of purified water. 30 g of N-chlorosuccinimide was added to this solution, stirred, left to stand for 2 hours, and lyophilized to obtain a powder. To 50 g of this powder was added 1000 ml of a 70% aqueous ethanol solution, and the mixture was stirred for 30 minutes.
Washed with 00 ml. The residue was dissolved in 2000 ml of purified water, and spray-dried at an intake temperature of 150 to 160 ° C and an exhaust temperature of 55 to 60 ° C to obtain a desired substance as a powder (yield: 61).
%).

Example 5 An amino acid-rich substance (60 g) was dissolved in 3000 ml of purified water. 50 g of chloramine T is added to this solution and stirred,
After standing for 2 hours, freeze-drying was performed to obtain a powder. To 50 g of this powder, 1000 ml of a 70% aqueous ethanol solution was added, followed by stirring for 30 minutes, suction filtration, and washing with 100 ml of purified water. The residue was dissolved in 2000 ml of purified water, and spray-dried at an intake temperature of 150 to 160 ° C and an exhaust temperature of 55 to 60 ° C to obtain a desired substance as a powder (yield: 58%).

Amino acid composition ratio measurement and sensory test Samples of the untreated amino acid-rich material (control) used in each of the above examples and the treated amino acid-rich material (Example 1-5) obtained in each example The contents of leucine and other amino acids were measured, and a sensory test on odor and taste was conducted.

a) Measurement test of amino acid content This measurement is performed by high performance liquid chromatography,
The measurement conditions were as follows.

Column: Develosil ODS-5N Detection: UV absorption spectrophotometer (200 nm) Mobile phase: 0.02 M-potassium dihydrogen phosphate Column temperature: Constant temperature around 40 ° C Flow rate: 1.0 ml / min Specimen: 20 μl of 1 mg / ml concentration sample b) Sensory test This test was performed by an expert panel consisting of 5 boys, and the procedure was as follows.

Odor: 1 g of a sample was collected in a beaker and determined by sniffing. Taste: A small amount of the sample was placed on the tongue and the taste was determined. C) Results The results of these tests were as shown in Table 1 below.

Application Example 1 (amino acid preparation-tablet) 200 g of tasteless and odorless amino acid-rich substance obtained in Example 1
97g of crystalline cellulose and 3g of magnesium stearate
Was added and mixed, and the diameter was 8 mm by a rotary tablet press,
A tablet having a thickness of 3.4 mm and a weight of 180 mg was produced (uncoated tablet). A part of the obtained uncoated tablet was subjected to film coating using hydroxypropyl methylcellulose and titanium oxide and using water as a solvent to obtain a white film-coated tablet.

In addition, plain tablets and film-coated tablets were produced using leucine according to the Japanese Pharmacopoeia in the same manner as described above.

Using these uncoated tablets and film-coated tablets as samples, under severe conditions (50 ° C., 30 days and 40 ° C., relative humidity 75
%, 30 days) (the leucine content was measured in the same manner as in the measurement example described above). The results are as shown in Table 2 below. All the preparations were stable, and no change was observed in appearance.

Application Example 2 (amino acid preparation-granule) 200 g of tasteless and odorless amino acid-rich substance obtained in Example 1
Was added and mixed with 6 g of polyvinylpyrrolidone, 60 ml of anhydrous ethanol was added to the mixture, and the mixture was granulated by a usual method.
It was dried to produce granules.

Application Example 3 (amino acid preparation-capsule) The granules obtained in Application Example 2 were filled in a gelatin capsule to obtain a capsule.

Application Example 4 (amino acid preparation-drink) 15 g of tasteless and odorless amino acid-rich substance obtained in Example 1
Was dissolved in 500 ml of purified water. 7.5 g of honey,
55 g of refined sugar and 200 ml of boiling water are added to dissolve the honey and refined sugar, and water is further added to make the total volume 750 ml, followed by autoclaving (121 ° C., 20 minutes). The solution was allowed to cool, and 50 ml was dispensed into bottles to produce drinks.

Application Example 5 (supplementary food or food material) Tasteless and odorless amino acid-rich substance 40 obtained in Example 1
g, 30 g of lactalbumin and 30 g of gelatin were suspended in water, and spray-dried at an intake temperature of 150-160 ° C. and an exhaust temperature of 55-60 ° C. to make powder. This powder was granulated with a dry granulator to obtain granules. This granule can be used as a food material, especially as a supplemental nutritional food material for amino acid enrichment.

(Effect of the Invention) According to the method of the present invention, the unpleasant taste and unpleasant odor of the amino acid-rich substance obtained in the process of producing a brewery derived from soybean can be removed very easily, and thus the treatment can be performed. The cost increase accompanying the above can be suppressed as much as possible.

In addition, since the amino acid-rich substance treated by the method of the present invention is tasteless and odorless, it is not necessary to use a flavoring agent or a flavoring agent in combination when used as a raw material of an amino acid preparation or a supplemental nutritional food material.

 ──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Yuji Noguchi 35 Higashi-gaicho, Higashi-ku, Nagoya City, Aichi Prefecture Inside Sanwa Chemical Research Institute Co., Ltd. Inside Sanwa Chemical Laboratory Co., Ltd.

Claims (9)

(57) [Claims] An oxidizing agent is allowed to act on a high amino acid-containing substance,
Next, a method for deodorizing a substance containing a high content of amino acids by removing an oxidizing agent. 2. The method according to claim 1, wherein the amino acid-rich substance is a mixture of amino acids containing a large amount of leucine. 3. A tasteless and odorless amino acid-rich substance according to claim 1 or 2, wherein the oxidizing agent is at least one of an inorganic oxidizing agent and an organic oxidizing agent. Method. 4. An oxidizing agent is added to a 0.0001-10% by weight solution of a substance having a high amino acid content at a temperature of -200 ° C.
The method according to any one of claims 1 to 3, wherein the reaction is carried out at a temperature within the above temperature range, and then the oxidizing agent is removed. 5. The method according to claim 1, wherein the oxidizing agent is removed by any one of powdering treatment, solvent washing treatment and enzyme treatment or a combination thereof. A method for deodorizing a substance high in amino acids according to one of the above aspects. 6. The method for deodorizing a substance rich in amino acids according to claim 3, wherein the inorganic oxidizing agent is hydrogen peroxide. 7. The organic oxidizing agent is acetic acid, acetic acid and acetate, N-
Claims: It is at least one selected from chlorosuccinimide, chloramine T and trichloromethanesulfonyl chloride, and when acetic acid or acetic acid and an acetate are used, is irradiated with ultraviolet rays. Item 4. The method for deodorizing a substance containing a high content of amino acids according to Item 3. 8. The method according to claim 5, wherein the powdering treatment is selected from evaporation to dryness, freeze drying and spray drying. 9. The method according to claim 5, wherein the solvent is selected from water, alcohol and an aqueous alcohol solution in the solvent washing treatment.