WO2019093708A1 - Method for producing odor-suppressing composition containing unsaturated oil and arginine - Google Patents

Abstract

The present invention relates to a method for producing an odor-suppressing composition containing an unsaturated oil and arginine, and a composition produced thereby, wherein a sulfur compound can be used to remove or reduce the odor generated by an aldehyde compound that is generated as the unsaturated oil is oxidized, and suppress discoloration caused by arginine.

Description

Process for preparing odor-suppressing unsaturated oil and arginine-containing composition

The present invention relates to a method for producing an odor-suppressing biologically-derived unsaturated oil and an arginine-containing composition, and a composition prepared thereby.

The fatty acid which is a kind of bio-derived oil is a carboxylic acid compound having a hydrocarbon chain having 12 to 24 carbon atoms, and unsaturated fatty acid means that at least one C = C double bond exists in a hydrocarbon chain. Omega-3 fatty acids have a double bond at the third carbon position from the end of a hydrocarbon chain. They contain a large amount of fatty acids such as fish oil and flaxseed oil, which are refined and used as food additives and health functional foods. In general, there are omega-3s such as EPA (Eicosapentaenoic acid) and DHA (Docosahexaenoic acid) in fish oil and seaweed, and omega-3 fatty acid called ALA (Alpha-linoleic acid) This omega-3 fatty acid lowers the levels of triglycerides and cholesterol and inhibits thrombus formation. It also reduces inflammation, helps absorption of calcium, helps calm, improves bone function, and prevents various adult diseases. Therefore, omega-3 fatty acids have been reported to prevent hypertension and arteriosclerosis, prevent Alzheimer's disease, anti-cancer effect and anti-inflammatory effects such as diabetes prevention, vision protection and arthritis.

However, recent clinical studies and epidemiologic studies have shown that omega-3 can not be used as a treatment for cardiovascular disease or Alzheimer's disease. However, omega-3 is present in the membranes of the human body, but it can not be synthesized in the body, so it is an essential fatty acid to be supplied from the outside, so taking or ingesting it is essential. Therefore, omega-3 health functional foods need to be taken to supplement at least essential fatty acids.

On the other hand, arginine, a kind of essential amino acid, is a precursor of nitric oxide. Nitric oxide is a signaling substance and is involved in various physiological activities such as immune function and vasodilation. Therefore, arginine is effective for hypertension and cardiovascular disease, improves blood supply, improves athletic performance, and has been reported to prevent hair loss. It is also known that it facilitates insulin secretion, improves sexual function as a neurotransmitter, and acts as an immune defense.

Therefore, there is a need for efforts to improve the deficient function of omega-3 for cardiovascular diseases revealed by clinical tests and the like.

On the other hand, omega-3 tends to avoid consumption because of its odor, compared with excellent efficacy. Unsaturated fatty acids such as omega-3 fatty acids are oxidized from the moment they are extracted and react with oxygen to form hydroperoxides and free radicals, which are then decomposed into aldehydes and alcohols. At this time, malodorous odors are caused by the aldehyde compounds such as cis-4-heptenal, octanal, 2,4-octadienal, trans-2 and cis-6-nonadienal.

Oxidized unsaturated fatty acids do not cause clinical side effects, but about 10% of fishy asians and about 20% of Westerners who take omega-3 fatty acids from fish oil as a raw material cause omega-3 to be avoided. It is the main reason to lower the preference.

Unsaturated fatty acids such as omega-3, as well as unsaturated oils such as squalene extracted from sharks and cod liver oil, which are used as health functional foods, are produced as odor-causing aldehyde compounds. In other words, these biological oils also have C = C double bond, which is oxidized by oxygen, and contains aldehyde compounds as malodorous impurities. Therefore, these unsaturated biological oils generally avoid taking them.

Aldehyde compounds smell even in very small amounts, so it is very difficult to completely block these odors. In order to block odor, Reference 1 has used a method of mixing a strong fragrance such as lemon fragrance into fish oil or the like in large quantities and then forming a soft capsule to shield the odor. Reference 2 of the present invention has developed a food composition containing lemon fragrance. Cited Reference 3 used omega-3 coated with corn zein to make confectionery such as chips and cookies. In reference 4, whey and amino acid source were added to foods such as bread containing fat to prevent oxidation of fat, thereby enhancing consumers' taste and prolonging the preservation period. Citation 5 has developed a beverage composition in which fish oil and juice are made into an oil-in-water emulsion for cancer treatment and post treatment. Reference 6 has developed a method of smelling odor by immersing spice plants such as thyme, log wood and the like in fish oil for at least 20 days at around 20 degrees .

So far, the technology has been used to mask odor by using a strong incense or flavor masking method to eliminate rancidity odor, or to smell the odor by mixing proteins such as zein, whey protein and amino acid source. In a patent using a mixture of proteins, zein, whey and amino acid source, which are a complex of a wide range of amino acids, are used without specifying the chemical action with the odor source. Therefore, there is a problem that the odor removal efficiency is not high. In addition, imines produced by reaction with aldehydes, amino acids, proteins and the like, which cause odor, are hydrolyzed by gastric acid upon ingestion, resulting in an adverse reaction that generates aldehydes, resulting in odor in the trim.

[Prior Art Literature]

Patent literature

Citation 1: United States Patent Publication No. 2009-0304784

Reference 2: Korean Patent No. 10-0720638

Citation 3: United States Patent No. 11-530633

Reference 4: United States Patent No. 11-843812

Reference 5: International Patent Publication No. PCT 2014-050061

Reference 6: International Publication No. WO 2008-132127

Accordingly, an object of the present invention is to provide an unsaturated oil and an arginine-containing composition containing arginine capable of supplementing unsatisfactory action of an unsaturated oil in addition to an unsaturated biological oil including omega-3 fatty acids, The present invention provides a composition capable of eliminating or reducing odor caused by an aldehyde compound generated when an unsaturated oil is oxidized, and a method for producing the same.

Specifically, it is an object of the present invention to provide a malodor-suppressing unsaturated oil / arginine composite composition capable of eliminating or reducing odor caused by an aldehyde compound generated by oxidation of an unsaturated oil such as omega-3 fatty acid using a sulfur compound .

In one aspect of the present invention, there is provided a method for producing an odor-suppressing unsaturated oil and an arginine-containing composition, which comprises mixing at least one of sulfur compounds capable of generating sulfur dioxide and cysteine with an unsaturated oil to remove an aldehyde compound generated from the unsaturated oil step; And adding arginine or a salt thereof to the composition, and a process for producing an odor-suppressing unsaturated oil and an arginine-containing composition.

In one aspect of the present invention, the sulfur compounds capable of generating sulfur dioxide include at least one of sodium sulfite, sodium acid sulfite, sodium metabisulfite, sodium dibasulfite, potassium sulfite, potassium metabisulfite, potassium acid sulfite and calcium hydrogen sulfite Containing unsaturated oil and a method for producing an arginine-containing composition.

In one aspect of the present invention, the salt of arginine is at least one of a hydrochloride salt, a sulfate salt, and a nitrate salt, and provides a method of preparing an odor-suppressing unsaturated oil and an arginine-containing composition.

In one aspect of the present invention, the method provides a method for preparing an odor-suppressing unsaturated oil and an arginine-containing composition, which further comprises a step of precipitating and removing the sulfite adduct produced after removing the aldehyde compound .

In one aspect of the present invention, the method comprises the step of adding a basic amino acid to remove residual sulfur dioxide after the step of removing the aldehyde compound, and a method for producing an odor-suppressing unsaturated oil and an arginine- to provide.

In one aspect of the present invention, the method further comprises the step of adding a lipophilic bioactive material after the step of adding arginine or a salt thereof, wherein the lipophilic bioactive material is an anthocyanin, saponin, ginsenoside, quercetin, Containing unsaturated oil and an arginine-containing composition, wherein the composition is at least one or more selected from the group consisting of furitrine, curcumin, cinnamide, lycopene, beta carotene, lutein, vitamin E, polyphenol, tocopherol and terpene.

Another aspect of the present invention provides an odor-suppressing unsaturated oil and an arginine-containing composition produced by any one of the above-described manufacturing methods.

The odor-suppressing unsaturated oil / arginine composition according to an embodiment of the present invention reacts sulfur compounds in a solid state without using any additional solvent to solidify the odor source caused by the aldehyde compound generated when the unsaturated oil is oxidized, It is very convenient compared to the method by distillation or the like, and it is possible to suppress discoloration due to arginine.

Thus, it is possible to provide an odor-suppressing unsaturated oil-containing composition which prevents an uncomfortable feeling on the administration side and has an improved cardiovascular disease prevention function.

1 shows the reaction with aldehyde 1) Shiff-base reaction using lysine; 2) Michael addition reaction with cysteine; 3) A schematic diagram of sulfite addition reaction.

Figure 2 is a GC analysis chart of Omega 3.

3 is a graph showing a change in removal rate according to reaction temperature in the removal reaction of aldehydes using sodium diphosphate.

BRIEF DESCRIPTION OF THE DRAWINGS The above and other objects, features, and advantages of the present invention will become more readily apparent from the following description of preferred embodiments with reference to the accompanying drawings. However, the present invention is not limited to the embodiments described herein but may be embodied in other forms. Rather, the embodiments disclosed herein are provided so that this disclosure will be thorough and complete, and will fully convey the concept of the invention to those skilled in the art.

Like reference numerals are used for like elements in describing each drawing. In the accompanying drawings, the dimensions of the structures are shown enlarged from the actual for the sake of clarity of the present invention. The terms first, second, etc. may be used to describe various components, but the components should not be limited by the terms. The terms are used only for the purpose of distinguishing one component from another. For example, without departing from the scope of the present invention, the first component may be referred to as a second component, and similarly, the second component may also be referred to as a first component. The singular expressions include plural expressions unless the context clearly dictates otherwise.

In the present application, the terms "comprises" or "having" and the like are used to specify that there is a feature, a number, a step, an operation, an element, a component or a combination thereof described in the specification, But do not preclude the presence or addition of one or more other features, integers, steps, operations, components, parts, or combinations thereof. Also, where a portion such as a layer, film, region, plate, or the like is referred to as being "on" another portion, this includes not only the case where it is "directly on" another portion, but also the case where there is another portion in between. On the contrary, when a part such as a layer, film, region, plate or the like is referred to as being "under" another part, it includes not only the case where it is "directly underneath" another part but also another part in the middle.

The odor-suppressing unsaturated oil / arginine complex composition according to an embodiment of the present invention includes a step of removing odors using sulfur compounds.

Since arginine used in the present invention is an amine compound, a very small amount of arginine is dissolved with an unsaturated oil at room temperature, and a Schiff base reaction with an aldehyde, which is an omega-3 malodorous substance, occurs to form an imine compound to alleviate odor . However, when the arginine / unsaturated oil complex is ingested, there is a problem that the aldehyde is formed by the gastric acid and the odor is felt in the trim. In addition, the arginine / unsaturated oil complex exhibits pink-red color due to the resulting imine compound. When stored for a long time, the amount of the imine compound is increased due to oxidation, thereby causing discoloration of the epidermis of the capsule preparation such as soft and hard capsules .

Accordingly, the present invention has developed a technique for removing aldehydes from unsaturated oils. Aldehydes are generally reactive and can react with various materials. However, in the present invention, in consideration of toxicity of reactants and convenience of reaction, 1) a Shiff-base reaction using lysine; 2) Michael addition reaction with cysteine; 3) sulfite addition reaction. These reactions are shown in Fig. 1

As a result of the GC analysis (column: DB-1HT (length: 30 m, ID: 0.32 mm, film: 0.01 탆); detection: 350 degrees (FID) -3 is not very well detected by GC because of the trace amount of octane, which is the most difficult to remove by octane, according to the reference 4, 10% of omega-3 was added to the solution and the reactivity was compared .

Removal efficiency was calculated from the relative area of the main peak of omega-3 and the octanal peak as follows.

Octanal relative peak area (PA-OL) = Octanal peak area (ab 5.7 min) / Omega-3 peak area (ab 17.5 min)

Octane peak area (PA-ROL) = Octanal peak area after RX (ab 5.7 min) / Omega-3 peak area (ab 17.5 min) after aldehyde removal reaction

Octanal removal efficiency = [(PA-OL) - (PA-ROL)] / (PA-OL)

Based on the above facts, the experiment was conducted with the reactant compositions shown in Table 1 below.

Materials	Sample name
	OM	LS	LZ	CA	AP	AD	OA	BA	CY	SB
Omega-3	1 ml	1 ml	1 ml	1 ml	1 ml	1 ml	1 ml	1 ml	1 ml	1 ml
Octanal	0.1 ml	0.1 ml	0.1 ml	0.1 ml	0.1 ml	0.1 ml	0.1 ml	0.1 ml	0.1 ml	0.1 ml
Lysine	0	0.1 g	0.1 g	0.1 g	0.1 g	0.1 g	0.1 g	0.1 g	0	0
Citric acid	0	0	0	a very small amount	0	0	0	0	0	0
Aspartic acid	0	0	0	0	a very small amount	0	0	0	0	0
Adipic acid	0	0	0	0	0	a very small amount	0	0	0	0
Oleic acid	0	0	0	0	0	0	1 drop	0	0	0
Boric acis	0	0	0	0	0	0	0	a very small amount	0	0
Cysteine	0	0	0	0	0	0	0	0	0.1 g	0
Sodium bisulfite	0	0	0	0	0	0	0	0	0	0.1 g
Zeolite	0	0	0.1 g	0	0	0	0	0	0	0

As shown in Table 1, a small amount of a weak acid was added to the reaction of lysine to cause a weak acid to catalyze the Shiff-base reaction. The reason for adding zeolite to the reaction was to remove water generated during the reaction. However, according to the octane removal rate in the room temperature reaction shown in Table 2, the removal of catalyst and water did not significantly affect the reaction, and the reactivity of the Shiff-base reaction itself was not high. On the other hand, the sulfurous acid addition reaction with sodium acid sulfite showed a relatively high removal rate. Table 2 shows the octanal removal rate at room temperature.

Sample	Reaction temperature	Reaction time	Octanal peak area (ab 5.7 min)	Omega mean peak (ab 17.5 min)	Removal ratio (%)
OM	25	Overnight	4143	38904	-
LS	25	Overnight	4753	48068	7.1
LZ	25	Overnight	4730	44575	0.4
CA	25	Overnight	4672	43680	0
AP	25	Overnight	4926	46517	0.6
AD	25	Overnight	4598	46027	6.2
OA	25	Overnight	4190	39137	0
BA	25	Overnight	4474	41849	0
SB	25	Overnight	3164	38638	23.10

As shown in Table 3, the Schiff base reaction was not highly reactive even at a high temperature of 60 ° C. On the other hand, Michael addition reaction by cysteine showed relatively high removal rate, and addition of sulfite with acidic sodium sulfite showed the highest removal rate. Table 3 shows octanal removal rates in a high temperature reaction.

Sample	Reaction temperature	Reaction time	Octanal peak area (ab 5.7 min)	Omega mean peak (ab 17.5 min)	Removal ratio (%)
OM	60	6 hr	4143	38904	-
LZ	60	6 hr	3944	38113	2.8
LS	60	6 hr	3912	37434	1.9
CA	60	6 hr	3910	37407	1.8
AP	60	6 hr	4057	39013	2.4
CY	60	6 hr	3428	38967	17.4
SB	60	6 hr	1561	40095	63.4

In order to investigate the reactivity of sodium hydrosulfite, 1% of aldehyde compounds such as heptenal, octanal, nonadienal, etc. Were added to omega - 3 to investigate their elimination efficiency. At this time, sodium dithiosulfate was used in an amount of 5 wt% relative to the omega-3 solution, and the reaction temperature was maintained at room temperature, 60, 80, and 100 ^o C for 24 hours, and GC analysis was performed to examine the aldehyde removal rate. Respectively. As a result, the aldehyde removal rate was improved with increasing the reaction temperature. At 60 ^o C, almost 100% of the nonadienal and heptenal were removed, and the octanal removal rate was about 50%. At 80 ^° C and above, the removal rate of all compounds was almost 100%.

As a result, the cysteine containing sulfur showed some performance for aldehyde removal. As shown above, cysteine is not highly reactive but its cysteine is very toxic and very safe for use.

On the other hand, sulfur compounds such as acidic sodium sulfite and sodium dibasic sulfate showed excellent aldehyde removal rate. The common feature of these sulfur compounds is that sulfur dioxide is considered to be involved in the aldehyde removal reaction as a substance capable of generating sulfur dioxide gas. Sulfur compounds that can generate sulfur dioxide used as a food additive include sodium sulfite, sodium bisulfite, sodium metabisulfite, sodium hydrosulfite, potassium sulfite, Potassium metabisulfite, potassium hydrogen sulfite, calcium hydrogen sulfite, etc., can be used for the purpose of removing the aldehyde of the present invention. Since the compound produced by the addition reaction of the sulfites is a salt compound, it is insoluble in unsaturated oil. Therefore, when the compound is left at room temperature or low temperature, it is separated by precipitation and is removed by filtration.

This technology is applicable not only to unsaturated fatty acids such as omega-3 but also to unsaturated oils such as squalene extracted from shark and cod liver oil produced from cod liver. In other words, these biological oils also have C = C double bond, which is oxidized by oxygen, and contains aldehyde compounds as malodorous impurities.

The preparation of the odor-suppressing unsaturated oil-containing composition according to one embodiment of the present invention comprises: 1) a step of removing aldehydes; 2) precipitation and filtration steps; 3) arginine mixing and grinding steps; 4) mixing step; 5) capsule manufacturing step.

1) Aldehyde removal step

In the step of removing the aldehyde generated by the autoxidation of the unsaturated oil, the sulfite salt or cysteine in the fine powder state is added to omega-3 and dispersed by stirring. At this time, it is effective to mix a small amount of an antioxidant such as vitamin E to prevent the oxidation of the unsaturated oil.

The sulfites include sodium sulfite, acidic sodium sulfite, sodium metabisulfite, sodium dibasulfate, potassium sulfite, potassium metabisulfite, acidic sodium sulfite and calcium hydrogen sulfite, which are used as food additives. The particle size of these particles is preferably not more than 50 μm. And if it is more than 50 μm, the surface area is small and the reactivity is low.

Since the aldehyde compound contained in the purified unsaturated oil used as a health functional food is very difficult to be analyzed by GC, the amount of the aldehyde compound is estimated to be several ppm or less, so that the amount of the sulfite compound used in the elimination reaction may be small. And 0.5% by weight or less based on the unsaturated oil is suitable for controlling the residual sulfur dioxide according to the standard of the phytosanitary standard. There is a problem in that the sulfur dioxide generated can exceed the standards of the pharmacy.

The reaction temperature is suitably from -10 ° C to 80 ° C. Unsaturated oil can be oxidized at 80 ° C or higher, and the reaction is frozen at -10 ° C or lower, so that sufficient reaction may not occur. Usually, the aldehyde compound in the purified unsaturated oil is very small, so it is not necessary to add a high temperature for the purpose of increasing the reaction efficiency. The reaction time is suitably 4 to 48 hours. The reaction may not be completed in less than 4 hours, and the reaction is terminated in 48 hours or more, so that there is no need to react further.

Next, basic amino acids are added and reacted to neutralize the sulfur dioxide dissolved in the unsaturated oil, if necessary. Basic amino acids include lysine, histidine, and arginine. The molar ratio of the sulfite compound used in the reaction is 1-20 times. Under 1x, complete reaction may not occur, and 20 times or more may cause waste.

Cysteine may be cysteine itself and salts thereof such as hydrochloride, sulfate, and acetate. The particle size of these particles is preferably not more than 50 μm. When the thickness is 50 m or more, there is a problem that the surface area is small and the reactivity is low.

The amount of cysteine is suitably from 1 to 10% by weight based on the unsaturated oil. At least 10% by weight may be wasted, and at 1% by weight or less, the reactivity is low and sufficient removal may not occur. The reaction temperature is in the range of 20 to 80 ° C. Omega-3 can be oxidized at a temperature higher than 80 ° C. The reaction time is suitably from 6 to 48 hours. The reaction may not be completed for less than 6 hours, and the reaction is terminated for longer than 48 hours, so that no further reaction is required.

In the present aldehyde removing step, a sulfur compound such as a sulfite or cysteine is dissolved in a solvent and reacted in a solid state without being reacted, thereby avoiding a troublesome process of removing the solvent.

In order to manifest a complex function in the unsaturated oil, a powder such as aronia, ginseng, bellflower, capers, onion, turmeric, cinnamon, tomato, carrot, kale, nuts, green tea, The lipid-soluble physiologically active substance can be extracted.

2) Precipitation and filtration step

It is preferable to remove the sulfite adduct produced in the step of removing aldehydes because an adverse reaction occurs to generate an aldehyde compound in an acid or a base. When the aldehyde removal step is completed, the reaction product is allowed to stand at room temperature to -20 ° C. for at least 12 hours to precipitate the resulting sulfurous acid addition compound, followed by centrifugation or filtration to remove the impurities. This method is very economical and convenient in comparison with distillation which is a purification method commonly used in chemical processes.

Cysteine is not toxic and can be left alone, but should be removed if it can affect the doses of the main unsaturated oils and arginine.

3) Arginine mixing and grinding steps

Arginine or its salt hydrochloride, sulphate, acetate and the like are added to the unsaturated oil and mixed and pulverized with a homomix, a colloid mill or a ball mill. The amount of arginine is 0-80% by weight and can be adjusted according to the desired function. That is, arginine may not be used only for the function of omega-3, and the amount of addition of up to 80% by weight may be increased to emphasize the function of arginine.

4) Blending step

As a supplementary ingredient, a physiologically active substance such as vitamin E, beta-carotene, lycopene, quercetin, saponin, polyphenol or lutein is added as needed. To prevent sedimentation of arginine and the like, beeswax, lecithin and the like are added to increase the viscosity.

5) Capsule preparation step

The raw material thus prepared is removed from the bubbles under vacuum and made into soft or hard capsules or the like to be used as a health functional food.

Hereinafter, various aspects of the present invention will be described.

In one aspect of the present invention, there is provided a method for producing an odor-suppressing unsaturated oil and an arginine-containing composition, which comprises mixing at least one of sulfur compounds capable of generating sulfur dioxide and cysteine with an unsaturated oil to remove an aldehyde compound generated from the unsaturated oil step; And adding arginine or a salt thereof to the composition, and a process for producing an odor-suppressing unsaturated oil and an arginine-containing composition.

In one embodiment, the unsaturated oil is linoleic acid (ALA) derived from plant seeds such as flax, hemp, and the like; Omega-3 from fish such as salmon, krill, sardines, and the like; Omega-3 fatty acids derived from seaweeds; Squalene, cod liver oil or the like.

In one aspect of the present invention, the sulfur compounds capable of generating sulfur dioxide include at least one of sodium sulfite, sodium acid sulfite, sodium metabisulfite, sodium dibasulfite, potassium sulfite, potassium metabisulfite, potassium acid sulfite and calcium hydrogen sulfite Containing unsaturated oil and a method for producing an arginine-containing composition.

In one aspect of the present invention, the method comprises the step of adding a basic amino acid to remove residual sulfur dioxide after the step of removing the aldehyde compound, and a method for producing an odor-suppressing unsaturated oil and an arginine- to provide.

In one aspect of the present invention, a method for preparing an odor-suppressing unsaturated oil and an arginine-containing composition, further comprising the step of precipitating and removing an amino acid and a sulfite adduct produced after removing the aldehyde compound, to provide.

In one aspect of the present invention, the salt of arginine is at least one of a hydrochloride salt, a sulfate salt, and a nitrate salt, and provides a method of preparing an odor-suppressing unsaturated oil and an arginine-containing composition.

In one aspect of the present invention, the arginine or a salt thereof may be 0-80 wt%.

In one aspect of the present invention, the method further comprises the step of adding a lipophilic bioactive material after the step of adding arginine or a salt thereof, wherein the lipophilic bioactive material is an anthocyanin, saponin, ginsenoside, quercetin, Containing unsaturated oil and an arginine-containing composition, wherein the composition is at least one or more selected from the group consisting of furitrine, curcumin, cinnamide, lycopene, beta carotene, lutein, vitamin E, polyphenol, tocopherol and terpene.

Fat or fatty acid dissolves in the digestive organ lipophilic vitamins such as lipid-soluble physiologically active substances to microemulsify to promote the absorption of the body. Unsaturated oil-containing fat or composition is also a kind of fat, so it will work the same. In the present invention, a physiologically active substance in a plant is extracted using an unsaturated oil-containing oil or composition as an extraction solvent to promote the absorption of the lipophilic bioactive substance contained in the plant to improve the bioavailability, Unsaturated oil-containing compositions and methods for their preparation have been developed. Plants include water-soluble substances that dissolve in water, amphoteric substances that dissolve in both water and oil, and oil-soluble substances that dissolve in oil. Among them, plant-derived physiologically active substances which can be dissolved in unsaturated oils include various known substances as shown in Table 1 below. In view of their physiological activity characteristics, anthocyanins, which are a kind of flavonoids such as Aronia, have been reported to have antioxidant, vision improvement, arthritis and oxidative stress prevention function. Ginsenoside, a ginseng saponin, has various functions such as immunity enhancement, liver function protection, anti-diabetes, anti-arteriosclerosis, inhibition of lipid peroxidation. Curcumin in curcumin has been reported to prevent heart attack and inhibit cancer metastasis. Excreted carotene, lutein, terpene, etc. prevent antioxidant damage to cells, promote the regeneration of already damaged cells, prevent aging, relieve eye fatigue and prevent night blindness.

Table 4 is an example of a plant-derived lipid-soluble physiologically active substance.

[Table 4]

[Correction according to Rule 91. 07.01.2019]

[Correction according to Rule 91. 07.01.2019]

[Correction according to Rule 91. 07.01.2019]

[Correction according to Rule 91. 07.01.2019]

As a method for producing an unsaturated oil-containing composition containing a plant-derived physiologically active substance, a method of extracting a physiologically active substance using alcohol or an organic solvent can be used. However, in this method, since the solvent used for extraction is removed by a method such as vacuum distillation and the extracted physiologically active substance is mixed with unsaturated oil, the process is troublesome and the loss of the extract is severe, resulting in low productivity and uneconomical problems. Therefore, in the present invention, productivity and economical efficiency are improved by using the unsaturated oil-containing oil or the composition as a direct extraction solvent and using a manufacturing process which does not require a solvent removal process. Another aspect of the present invention is a process for producing The present invention provides a malodor-suppressing unsaturated oil and an arginine-containing composition. The malodor-suppressing unsaturated oil and arginine-containing composition according to an embodiment of the present invention can be used as a health functional food after being formulated with a soft capsule. The odor-suppressing unsaturated oil and the arginine-containing composition according to an embodiment of the present invention can be manufactured as an oil-in-water emulsion and used as a composition of juice or beverage. The odor-suppressing unsaturated oil and arginine-containing composition according to an embodiment of the present invention can inhibit fishy smell and odor, and can be used as a food additive having a high flavor and nutritional supply source.

The odor-suppressing unsaturated oil and arginine-containing composition according to an embodiment of the present invention can remove or reduce malodors caused by aldehyde compounds generated by oxidation of unsaturated oils stored and distributed by arginine. Thus, it is possible to prevent unpleasant feeling on the taking and to increase the storage period of foods containing the odor-suppressing unsaturated oil. In addition, the active ingredient of plants and animals can be absorbed at the same time by taking one dose, thereby providing convenient convenience and providing a wider and more effective physiological health function.

Hereinafter, the present invention will be described more specifically by way of specific examples. The following examples are provided to aid understanding of the present invention, and the scope of the present invention is not limited thereto.

Example 1

After the acidic sodium sulphate was sufficiently exchanged in a mortar to obtain particles having a size of 50 μm or less, 0.1 g was added to 200 g of omega-3, and 0.5 g of vitamin E was added. The mixture was stirred at 80 ° C. for 6 hours, Lt; / RTI > 1 g of the following lysine is added to the reaction mixture and stirred for 1 hour. The reaction mixture is placed in a refrigerator for 24 hours, and then centrifuged to remove the precipitate. The omega-3 in which the aldehyde compound was removed was used to prepare a soft capsule with a soft capsule maker.

Example 2

Sodium sulphate was added to the oval-shaped bowl to obtain particles having a size of 50 μm or less. Then, 0.05 g of ointment was added to 200 g of omega-3, and 0.5 g of vitamin E was added. The mixture was stirred at -10 ° C. for 12 hours, Lt; / RTI > Then, 0.5 g of histidine is added to the reaction mixture, which is then stirred for 1 hour. The reaction mixture is placed in a refrigerator for 24 hours, and centrifuged to remove the precipitate. To 100 g of omega-3, from which the aldehyde compound had been removed, 40 g of arginine, 1 g of vitamin E and 10 g of lecithin were added and mixed with a homomixer. The mixture was thoroughly mixed and placed in a vacuum oven to remove air bubbles. Capsules were prepared.

Example 3

Sodium metabisulfite was added to a mortar to obtain particles having a particle size of 50 μm or less. Then, 0.2 g of the mixture was added to 200 g of omega-3 and stirred at 60 ° C. for 6 hours under nitrogen atmosphere. Next, 1 g of arginine is added to the reaction mixture, which is then stirred for 1 hour. The reaction mixture is placed in a refrigerator for 24 hours, and centrifuged to remove the precipitate. To 20 g of omega-3, from which the aldehyde compound has been removed, add 80 g of arginine hydrochloride and 0.5 g of each of vitamin E, beta carotene, lycopene, quercetin, saponin and polyphenol. The resulting mixture is thoroughly pulverized and mixed with a colloid mill, The bubbles were removed and hard capsules were prepared with a hard capsule machine.

Example 4

Sodium dithionite was poured into a mortar to obtain particles having a size of 50 μm or less. Then, 0.5 g of the mixture was added to 200 g of omega-3 and stirred at 40 ° C. for 8 hours under nitrogen atmosphere. The reaction mixture is placed in a refrigerator, left for 24 hours, and centrifuged to remove the precipitate. To 100 g of omega-3 from which the aldehyde compound had been removed, 40 g of arginine hydrochloride and 0.5 g of each of vitamin E, beta carotene, lycopene, quercetin, saponin, polyphenol and the like were added. 10 g of lecithin was added and sufficiently pulverized and mixed with a colloid mill The resultant was put in a vacuum oven and vacuum was applied to remove the bubbles, and a soft capsule was prepared by a soft capsule machine.

Example 5

Potassium sulfite was added to a mortar to obtain particles having a size of 50 μm or less. Then, 1 g was added to 200 g of omega-3, and the mixture was reacted at room temperature for 8 hours under nitrogen atmosphere. The reaction mixture is placed in a refrigerator, left for 24 hours, and centrifuged to remove the precipitate. 30 g of arginine hydrochloride and 0.5 g of vitamin E, beta-carotene, lycopene, quercetin, saponin, polyphenol and the like were added to 100 g of omega-3 from which the aldehyde compound had been removed, and 5 g of beeswax was added thereto. The mixture was thoroughly pulverized and mixed with a colloid mill The resultant was put in a vacuum oven and vacuum was applied to remove the bubbles, and a soft capsule was prepared by a soft capsule machine.

Example 6

The potassium metabisulfite was added to the mortar to obtain particles having a size of 38 μm or less. Then, 0.01 g of the potassium metabisulfite was added to 200 g of omega-3 and the mixture was reacted under nitrogen atmosphere with stirring at 80 ° C. for 8 hours. The reaction mixture is placed in a refrigerator, left for 24 hours, and centrifuged to remove the precipitate. To 100 g of Omega-3, 100 g of the aldehyde compound, 30 g of arginine, 5 g of vitamin E, saponin, and lutein were added, and 5 g of beeswax was added. The mixture was thoroughly pulverized and mixed with a colloid mill, And soft capsules were prepared with a soft capsule maker.

Example 7

After adding 0.05 g of omega-3 to 200 g of omega-3 and adding 1 g of vitamin E, the mixture was stirred for 12 hours at a temperature of 40 ° C and stirred under a nitrogen atmosphere Lt; / RTI > The reaction mixture is placed in a refrigerator, left for 24 hours, and centrifuged to remove the precipitate. 3 g of arginine, 5 g of saponin and lutein, and 5 g of lecithin were added to 100 g of omega-3, from which the aldehyde compound had been removed. The mixture was thoroughly pulverized and mixed with a colloid mill, and the mixture was placed in a vacuum oven. Hard capsules were prepared with a capsule machine.

Example 8

Subsequently, 1 g of vitamin E was added to 200 g of omega-3, and the mixture was stirred at 0 ° C. for 12 hours. The mixture was stirred under nitrogen atmosphere Lt; / RTI > The reaction mixture is placed in a refrigerator, left for 24 hours, and centrifuged to remove the precipitate. The omega-3 in which the aldehyde compound was removed was used to prepare a soft capsule with a soft capsule maker.

Example 9

Cysteine hydrochloride was added to a mortar to obtain particles having a size of 50 μm or less. Then, 20 g of ointment was added to 200 g of omega-3, 2 g of vitamin was added, and the mixture was reacted under nitrogen atmosphere with stirring at 80 ° C. for 24 hours. 10 g of lecithin was added to omega-3 from which the aldehyde compound had been removed, and a soft capsule was prepared using a soft capsule machine.

Example 10

Cysteine was sufficiently introduced into a mortar to obtain particles having a particle size of 50 μm or less. Then, 10 g of the mixture was placed in 200 g of omega-3, and the mixture was reacted under nitrogen atmosphere with stirring at 60 ° C. for 48 hours. To 100 g of omega-3, from which the aldehyde compound had been removed, 40 g of arginine, 2 g of vitamin E and 3 g of beeswax were added and mixed with a homomixer. The mixture was thoroughly mixed and placed in a vacuum oven. Vacuum was removed to remove air bubbles. Capsules were prepared.

Example 11

Add 1 g of vitamin E to 500 g of omega-3 and add 5 g of red ginseng powder, 5 g of arhnia powder 5 g of onion powder, 5 g of carrot powder and 5 g of tomato powder were mixed and reacted under nitrogen atmosphere with stirring at 40 ° C. for 48 hours. The reaction mixture is placed in a refrigerator, left for 24 hours, and centrifuged to remove the precipitate. Then, the resultant was placed in a vacuum oven, a vacuum was applied to remove air bubbles, and a soft capsule was prepared with a soft capsule maker.

Example 12

Potassium sulfite was poured into a mortar to obtain particles having a size of 38 μm or less. Then, 1 g was added to 200 g of squalene, 1 g of vitamin E was added, and the mixture was reacted under nitrogen atmosphere at room temperature for 12 hours with stirring. The reaction mixture is placed in a refrigerator, left for 24 hours, and centrifuged to remove the precipitate. Then, the resultant was placed in a vacuum oven, a vacuum was applied to remove air bubbles, and a soft capsule was prepared with a soft capsule maker.

Example 13

After acidic sodium sulphate was sufficiently exchanged in a mortar to obtain particles having a size of 38 μm or less, 1 g was added to 200 g of cod liver oil, 1 g of vitamin E was added, and the mixture was stirred at 40 ° C. for 12 hours under a nitrogen atmosphere Lt; / RTI > The reaction mixture is placed in a refrigerator, left for 24 hours, and centrifuged to remove the precipitate. Then, the resultant was placed in a vacuum oven, a vacuum was applied to remove air bubbles, and a soft capsule was prepared with a soft capsule maker.

While the present invention has been described in connection with what is presently considered to be practical exemplary embodiments, it is to be understood that the invention is not limited to the disclosed embodiments, but, on the contrary, It will be understood. It is therefore to be understood that the above-described embodiments are illustrative and non-restrictive in every respect.

Claims (9)

1. A method for producing an odor-suppressing unsaturated oil and an arginine-containing composition,

   Mixing at least one of a sulfur compound capable of generating sulfur dioxide and cysteine with an unsaturated oil to remove an aldehyde compound generated in the unsaturated oil; And

   Arginine, or a salt thereof, comprising the step of adding an arginine or a salt thereof.
2. The method according to claim 1,

   Wherein the sulfur compound capable of generating sulfur dioxide comprises at least one of sodium sulfite, sodium acid sulfite, sodium metabisulfite, sodium dibasulfate, potassium sulfite, potassium metabisulfite, potassium acid sulfite and calcium hydrogen sulfite. A method for producing a composition containing a polyunsaturated oil and an arginine.
3. The method according to claim 1,

   Wherein the salt of arginine is at least one of a hydrochloride salt, a sulfate salt and a nitrate salt, and a method of producing an odor-suppressing unsaturated oil and an arginine-containing composition.
4. The method according to claim 1,

   Wherein the arginine or its salt is 0-80 wt.%, And the composition contains an odor-suppressing unsaturated oil and an arginine-containing composition.
5. The method according to claim 1,

   The method of manufacturing an odor-suppressing unsaturated oil and an arginine-containing composition, further comprising the step of precipitating and removing the resulting sulfite adduct after removing the aldehyde compound.
6. The method according to claim 1,

   The method of manufacturing an odor-suppressing unsaturated oil and an arginine-containing composition, further comprising the step of introducing a basic amino acid to remove residual sulfur dioxide after the step of removing the aldehyde compound.
7. The method according to claim 1,

   The method further comprises the step of adding a fat-soluble bioactive substance after the step of adding arginine or a salt thereof,

   Wherein the liposoluble physiologically active substance is at least one or more of anthocyanin, saponin, ginsenoside, quercetin, capryitorin, curcumin, cinnamide, lycopene, betacarotene, lutein, vitamin E, polyphenol, tocopherol, A method for producing a composition containing a polyunsaturated oil and an arginine.
8. The method according to claim 1,

   Wherein said unsaturated oil is at least one or more of linoleic acid (ALA), fish oil, omega-3 fatty acid, squalene and cod liver oil.
9. 9. An odor-suppressing unsaturated oil and an arginine-containing composition produced by the production method of any one of claims 1 to 8.

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