KR20190104819A - Process for preparing organic acid glycerin esters containing isoflavone / soyasaponin complex extracted from soybean and cosmetic composition containing the same - Google Patents

Abstract

The present invention relates to a method for manufacturing organic acid glycerin ester containing an isoflavone/soyasaponin composite extracted from a soybean embryo, and a cosmetic composition containing the same. More specifically, isoflavone and soyasaponin are extracted from a soybean embryo (black soybean, green flesh black bean, soybean and the like) through organic acid hydrolysis and organic acid glycerin esterification to make a composite. According to the present invention, spontaneous separation of unsaturated fatty acid causing rancid odor and alkaline protein nitrogen compounds causing beany flavor is induced, thereby reducing odor.

Description

Process for preparing organic acid glycerin esters containing isoflavone / soyasaponin complex extracted from soybean embryos and cosmetic composition containing the same {process for preparing organic acid glycerin esters containing isoflavone / soyasaponin complex extracted from soybean and cosmetic composition containing the same}

The present invention relates to a method for producing an organic acid glycerin ester comprising an isoflavone / soyasaponin complex extracted from soybean embryos and to a cosmetic composition comprising the same, more specifically soybean embryos (black beans, weak beans, rat eye, soybeans, etc.) Isoflavone and soyasaponin by using organic acid hydrolysis and organic acid glycerin esterification, and a basic protein that generates unsaturated fatty acids and soybean salt that may exhibit acid odor in the preparation of the complex. The present invention relates to a method for preparing an organic acid glycerin ester comprising an isoflavone / soyasaponin complex extracted from soybean embryos that induces spontaneous separation of nitrogen compounds to reduce off-flavor, and a cosmetic composition comprising the same.

Obesity (Obesity) or obesity is a state in which fat is excessively accumulated in the body, which is a general term for a state in which fat is increased due to an increase in the number of adipocytes in adipocytes or an increase in the size of adipocytes. Obesity itself may not be a problem, but the social complications caused and the secondary complications caused by excess fat are severe. For example, obesity causes diseases such as hypertension, hyperlipidemia, heart disease, diabetes, arteriosclerosis, fatty liver, joint abnormalities, arthritis, sexual dysfunction, and cancer. In particular, once made fat cells are reduced in size, and because they are not naturally removed and remain in the body permanently, interest for the prevention and treatment of obesity is increasing.

To prevent or treat obesity, and to maintain a good weight requires a balanced diet and regular exercise. In recent years, obesity can be treated by taking drugs that reduce fat absorption. These diet pills can cause side effects such as cardiovascular disease and stroke, such as high blood pressure, and if you stop taking them, Cases often occur. In the case of severe obesity, surgery is performed to remove fat, to limit the amount of food the body can digest, or to perform surgery such as satellite surgery or gastric band insertion, but there are reports of side effects or complications. And even deaths have been reported.

Accordingly, the development of anti-obesity drugs with low toxicity and side effects are urgently needed, and recently, alternative methods or preparation methods of various extracts using active ingredients derived from natural products such as cosmetics, foods and health functional foods have been studied.

Recently, it has been reported that soybean embryo extract inhibits the differentiation of adipocytes, reduces the size of adipocytes, and converts white adipocytes into brown adipocytes to inhibit the accumulation of unnecessary fat in vivo. 10-1749967)

Soy is high in protein and fat and contains a large amount of bioactive substances such as isoflavone and soyasaponin. It is found more in germinated soybean embryos than not. Soy isoflavones have a molecular formula of C ₁₅ H ₁₀ O ₂ and 12 isomers are known, most of which are present as glycosides of daidzin, genistin and glycitin, including sugars.

 Isoflavone is called phytoestrogen because it is structurally similar to the female hormone estrogen and is known to exhibit estrogen-like activity in the human body.

Many studies have reported on the physiological activity and functionality of isoflavones.In addition to the effects of inhibiting the differentiation of adipocytes, it is associated with estrogens and causes cells such as prostate cancer, breast cancer, colon cancer, lung cancer and skin cancer. Anti-cancer effects that inhibit the growth of bone, increase calcium absorption in bone, prevent osteoporosis due to lack of estrogen, increase bone density, anti-aging and antioxidant activity, as well as lower the incidence of cardiovascular disease, diabetes, etc. (Korean Patent No. 10-1820096)

In the United States, about 15% of middle-aged women are receiving estrogen, but soybeans, a natural food, are spotlighted as an alternative to estrogen.

Soyasaponin is used in the aglycone soyasapogenol A, B, E and DDMP (2,3-dihydro-2,5-dihydroxy-6-methyl-4Hpyran-4-one) and the sugars attached to it. Are classified in various ways. In general, soyasaponin is A-A, Ab, Ad, Ae, Af and B-B is αg, βg, βa, γg, γa with DDMP and Ba, Bb, Bb ', Bc without DDMP. Are divided into Bd and Be, but they are named differently according to scholars. Soyasaponin is attracting much attention as it has been found to have various physiological activities such as anti-oxidant activity, anti-viral, hepatotoxicity removal, anti-tumor activity, and immune enhancing effect including blood cholesterol reduction effect.

However, soybean embryos contain not only isoflavones and soyasaponins but also unsaturated fatty acids, which easily dissipate in the air, create an unpleasant smell, and contain soy-based fishy smells. It has the disadvantage of degrading product functionality.

KR 10-1749967 B1 (2017.06.16) KR 10-1820096 B1 (2018.01.12)

In order to solve the above problems, the present invention is to provide a method for preparing an organic acid glycerine ester comprising an isoflavone / soya saponin complex extracted from soybean embryos to reduce off-odor by soybean fishy smell and cosmetic composition comprising the same.

In addition, the present invention is a method for preparing an organic acid glycerin ester comprising an isoflavone / soya saponin complex extracted from soybean embryos that are easily preserved by inducing spontaneous separation of unsaturated fatty acids that are easily rancid in air and may exhibit rancidity. It is to provide a cosmetic composition comprising.

The method for preparing an organic acid glycerin ester comprising an isoflavone / soyasaponin complex extracted from soybean embryos according to the present invention comprises preparing a raw material step (S10), isoflavone and soyasaponin extraction step (S20), filtration and Concentration step (S30), glycerin esterification reaction solution preparation step (S40), organic acid glycerin esterification step (S50), crystallization step (S60) of the esterified using the anti-solvent and filtration and drying step (S70) Isoflavone / soyasaponin complex extracted from soybean embryos.

Isoflavone and soya saponin extraction step (S20) by the organic acid hydrolysis is characterized in that for 1 to 2 hours at 1 to 20 atm, 80 ℃ to 150 ℃.

In addition, the isoflavone and soya saponin extraction step (S20) by the organic acid hydrolysis is characterized in that the organic acid is added 0.5 to 10 parts by weight based on 100 parts by weight of the raw material.

In addition, the organic acid glycerin esterification step (S50) is characterized in that proceeds from 80 ℃ to 150 ℃.

Cosmetic composition comprising an organic acid glycerin ester comprising an isoflavone / soya saponin complex extracted from soybean embryos according to the production method of the present invention 10 to 20 based on 100 parts by weight of the organic acid glycerin ester prepared by the manufacturing method Contains by weight.

The preparation method of the organic acid glycerin ester including the isoflavone / soyasaponin complex extracted from the soybean embryo according to the present invention can improve the extraction speed and yield of isoflavone and soyasaponin.

In addition, isoflavones and soyasaponin can be extracted simultaneously without using an organic solvent or performing a stepwise solvent fractionation process.

In addition, the off-flavor may be reduced by inducing spontaneous separation of the basic fatty acid nitrogen compounds that generate unsaturated fatty acids and soybeans that may exhibit acid odor.

In addition, the organic acid glycerin ester containing the isoflavone / soyasaponin complex extracted from soybean embryos according to the present invention is accompanied by emulsification stability and antiseptic properties, so that the amount of emulsifier and preservatives can be reduced when added during product manufacturing process. It is easy to add and use as a finished product.

1 is a flowchart of a method for preparing an organic acid glycerin ester including an isoflavone / soyasaponin complex extracted from soybean embryos according to the present invention.
Figure 2 shows the results of the volatile organic compound analysis experiment.

Advantages and features of the present invention and methods for achieving them will be apparent with reference to the embodiments described below in detail. However, the present invention is not limited to the embodiments disclosed below, but may be implemented in various forms, only the embodiments of the present invention make the disclosure of the present invention complete, and those of ordinary skill in the art to which the present invention belongs. It is provided to fully inform the scope of the invention, and the invention is defined only by the scope of the claims.

The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. In this specification, the singular also includes the plural unless specifically stated otherwise in the phrase. As used herein, "comprises" and / or "comprising" does not exclude the presence or addition of one or more other components in addition to the mentioned components.

Unless otherwise defined, all terms (including technical and scientific terms) used in the present specification may be used in a sense that can be commonly understood by those skilled in the art. In addition, terms defined in commonly used books are not to be interpreted ideally or excessively unless they are clearly specifically defined.

Hereinafter, preferred embodiments of the present invention will be described in detail.

Referring to Figure 1, a method for producing an organic acid glycerin ester comprising an isoflavone / soyasaponin complex extracted from soybean embryos according to the present invention is a raw material preparation step (S10), isoflavone and soyasaponin extraction step by organic acid hydrolysis (S20), filtration and concentration step (S30), glycerin esterification reaction solution preparation step (S40), organic acid glycerin esterification step (S50), crystallization step (S60) and filtration and drying step of the antisolvent (S70).

The raw material preparation step (S10) is soybean embryos washed with water after drying to prepare a powder form. Soybean embryos contain large amounts of bioactive substances, such as isoflavone and soyasaponin, which are found more in germinated soybean embryos than not, so they extract more isoflavones and soyasaponins. In order to use germinated soybean embryos, but is not limited thereto.

Next, the isoflavone and soya saponin extraction step (S20) by organic acid hydrolysis is a step of performing 1 to 2 hours of hydrolysis under conditions of 1 to 20 atm and 80 to 150 ° C. under an organic acid catalyst of a predetermined concentration or more.

If the temperature is less than 80 ℃, the rate of hydrolysis decreases due to the slow diffusion rate of water into the raw material. If the temperature exceeds 150 ℃, the hydrogen ion concentration of water increases and the exchange capacity of alkali ions decreases. Is reduced.

If the hydrolysis time is less than 1 hour, the hydrolysis progress is low, and the yield of hydrolysis can be reduced. If the hydrolysis time is more than 2 hours, peroxide reaction or carbonization reaction by prolonged heating exposure of the raw material proceeds, thereby peroxide or carbide. There is a risk of occurrence.

In addition, it is preferable that 0.5-10 weight part of organic acids are added with respect to 100 weight part of raw materials. When the organic acid is less than 0.5 parts by weight, the swelling rate is reduced by the hydration reaction of soybean embryo protein, the extraction yield is inhibited due to a decrease in hydrolysis capacity due to the reduction of the diffusion rate of the material. When the organic acid exceeds 10 parts by weight, the swelling caused by the hydration reaction of soybean embryo protein rises sharply, requiring more than 20 times as much water as the amount of raw materials.

Next, the filtration and concentration step (S30) is a step for removing the unreacted residue remaining in the hydrolyzate obtained by hydrolysis, wherein the unreacted residue refers to ash and insoluble cellulose which do not participate in hydrolysis. . The filtered hydrolyzate is concentrated under reduced pressure and concentrated to a concentration of 10 Brix.

Next, the step of preparing a glycerin esterification reaction solution (S40). It is dissolved by adding 10 parts by weight of an alkali catalyst to 100 parts by weight of glycerin to prepare a solution for glycerin esterification.

The organic acid glycerin esterification step (S50) is a step of performing the organic acid glycerin esterification reaction by adding the prepared glycerin esterification reaction solution to the hydrolysis concentrate. It converts isoflavones and soyasaponins extracted by hydrolysis into α-hydroxy acid glycerin esters, and the α-hydroxy acid glycerin esters are combined with emulsion stability and antiseptic properties to produce cosmetics. When used in the process, the amount of emulsifier and preservative can be reduced.

Organic acid glycerin esterification reaction is carried out at 80 ~ 150 ℃ it is carried out by repeating three times for 1 hour. If the temperature is less than 80 ° C., the evaporation rate of the water produced during the esterification reaction is low, and thus, the forward reaction rate of the ester reaction due to the reverse reaction by the remaining water is very slow or the conversion rate is significantly reduced. In addition, the carbonization phenomenon of the neutralized salts generated when it is carried out above 150 ℃ can discolor the ester color.

The crystallization step of the esterified product using an antisolvent (S60) induces crystal growth by adding an antisolvent to the esterified product and converts water, neutralized salts, odor components, basic protein nitrogen compounds, etc., which are self-separated from the esterified product. Step.

In the present invention, ethanol acts as an antisolvent for the esterified product, cannot dissolve or solubilize the esterified product containing isoflavone and soyasaponin, induces crystal growth, and self-separates water, neutralizing salts and odors from the esterified product. It serves to convert components, basic protein nitrogen compounds and the like.

The antisolvent concentration is preferably 50 to 500% of the amount of water in the esterified product. If the antisolvent concentration is less than 50% of the amount of water in the esterified product, the antisolvent concentration does not act as an antisolvent and is formed as a simple mixture. If more than 500% of the moisture content in the 400% range and there is no significant effect.

Finally, the filtration and drying step (S70) is a step of filtering the crystal sludge to remove the antisolvent (ethanol) and drying and pulverizing the crystallization to finally obtain an organic acid glycerin ester powder containing isoflavone and soya saponin. .

The method for preparing organic acid glycerine ester containing isoflavone and soya saponin can improve the extraction speed and yield of isoflavone and soya saponin, and isoflavone and soya saponin without using an organic solvent or performing a stepwise solvent fractionation process. It can be extracted at the same time.

To prepare a cosmetic comprising the organic acid glycerin ester powder containing the isoflavones and soya saponin, which has the advantage of easy preservation by the separation of unsaturated fatty acids that can remove the smell of soybean odor and reduce acid odor.

Example 1 Isoflavone and Soya Saponin Complex Using Organic Acid Hydrolysis Extraction and Organic Acid Glycerin Esterification

Soybean embryos were washed with water, dried and ground to prepare 100 g of soybean embryo powder in powder form.

To 100 g of soybean germ powder, 1 g of citric acid and 2 L of purified water were added and stirred at 80 rpm at 60 ° C. for hydrolysis for 1 hour.

The unreacted residue remaining in the hydrolyzed extract was filtered to obtain 1600 ml of soybean embryo organic acid hydrolyzate.

The soybean embryonic organic acid hydrolyzate was concentrated under reduced pressure and concentrated to 10Brix concentration to prepare a concentrate 100g.

10 g of NaOH was added to 100 g of glycerin and completely dissolved by heating and stirring at 135 ° C. for 10 minutes to prepare a glycerin ester reaction solution.

15 g of the glycerin esterification reaction solution was added to 100 g of the hydrolysis concentrate, and the organic acid glycerin esterification reaction was repeated three times at 105 ° C. for 1 hour.

To 100 g of the organic acid glycerin esterified reactant, 100 g of the same amount of antisolvent (95% ethanol) was added thereto, stirred at 60 rpm at 72 ° C. for 10 minutes, and left to cool for 2 hours to perform crystal growth.

The crystalline sludge was filtered to remove the antisolvent and completely dried at 40 ° C. to obtain an organic acid glycerine ester comprising an isoflavone / soyasaponin complex extracted from 25 g of soybean embryos.

Comparative Example 1 Crude Extract of Isoflavones and Soya Saponins by Organic Acid Hydrolysis

Soybean embryos were washed with water, dried and ground to prepare 100 g of soybean embryo powder in powder form.

To 100 g of soybean embryo powder, 1 g of citric acid and 2 L of purified water were added, and the mixture was stirred at 80 ° C. at 60 rpm for 1 hour to hydrolyze.

The unreacted residue remaining in the hydrolyzed extract was filtered to obtain 1600 ml of soybean embryo organic acid hydrolyzate.

The hydrolyzate was concentrated under reduced pressure and concentrated to 10Birx concentration to prepare 100 g of concentrate (crude extract of isoflavone and soya saponin by organic acid hydrolysis).

Experimental Example 1-Analysis of Volatile Organic Compounds

Using the composite of Example 1 and the extract of Comparative Example 1 was carried out volatile organic compound analysis (VOCs) through GC / MS, the results were obtained as shown in FIG.

Figure 2 (a) is the VOCs results of the extract of Comparative Example 1 and Figure 2 (b) is the VOCs results of the composite of Example 1. As can be seen in Figure 2 (b), the complex of Example 1 is Acetaldehyde, Propionaldehyde, Isobutyraldehyde, Benzaldehyde, Methylethylketone, 3-Methylpentane, n-Decanoic acid, cis-1,2-Dimethylcyclohexane, 2,6-Diphenylphenol and so on It was confirmed that the volatile organic compounds causing fishy smell were removed or reduced.

Experimental Example 2-Sensory Experiment

A cosmetic composition containing a glycerin ester including the complex of Example 1 or the extract of Comparative Example 1 was prepared in the composition specified in Table 1 below, and the sensory experiment was conducted.

ingredient Composition Example 1 (part by weight) Comparative Composition Example 1 (part by weight) Caffeine 50 50 Sodium salicylate 20 20 Glycerin Ester Comprising the Complex of Example 1 15 - Glycerin esters containing the extract of Comparative Example 1 - 15 Aspartame One One Soy Phospholipids 14 14

In order to confirm the off-odor effect according to the present invention, the odor sensory experiments of the composition example 1 and the comparative composition example 1 were conducted, and a total of 20 people having different ages and sexes were evaluated for the presence of odors. The results are shown in Table 2.

Odor (odor) Composition Example 1 (persons) Comparative Composition Example 1 U One 18 radish 19 2

It can be seen from Table 2 that Composition Example 1 comprising the organic acid glycerin ester according to the preparation method of the present invention has reduced odor compared to Comparative Composition Example 1.

S10: Raw material preparation stage
S20: Isoflavone and Soya Saponin Extraction Step by Organic Acid Hydrolysis
S30: Filtration and concentration step
S40: step of preparing a glycerin esterification reaction solution
S50: organic acid glycerin esterification step
S60: crystallization step of esterified product using anti-solvent
S70: Filtration and drying step

Claims (5)

In the manufacturing method of the organic acid glycerin ester containing the isoflavone / soya saponin complex extracted from soybean embryo,
Raw material preparation step (S10);
Isoflavone and soya saponin extraction step by organic acid hydrolysis (S20);
Filtration and concentration step (S30);
Glycerin esterification reaction solution preparation step (S40);
Organic acid glycerin esterification step (S50);
Crystallization step of the esterified product using an antisolvent (S60); And
Filtration and drying step (S70); Method of producing an organic acid glycerin ester comprising an isoflavone / soya saponin complex extracted from soybean embryos comprising. The method of claim 1,
The isoflavone and soya saponin extraction step (S20) by the organic acid hydrolysis is
A method for producing an organic acid glycerin ester comprising an isoflavone / soyasaponin complex extracted from soybean embryos, characterized in that it proceeds for 1 to 2 hours at 1 to 20 atm and 80 ° C to 150 ° C. The method of claim 1,
The isoflavone and soya saponin extraction step (S20) by the organic acid hydrolysis is
A method for producing an organic acid glycerin ester comprising an isoflavone / soyasaponin complex extracted from soybean embryos, characterized in that 0.5 to 10 parts by weight of an organic acid is added to 100 parts by weight of a raw material. The method of claim 1,
Organic acid glycerin esterification step (S50)
Method for producing an organic acid glycerin ester comprising an isoflavone / soyasaponin complex extracted from soybean embryos characterized in that proceeds at 80 ℃ to 150 ℃. Organic acid glycerin comprising an isoflavone / soyasaponin complex extracted from soybean embryos containing 10 to 20 parts by weight of the organic acid glycerin ester prepared by the method according to any one of claims 1 to 4. Cosmetic composition containing an ester.

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