KR101256971B1 - Method of extracting decursinol and cosmetic composition comprising the decursinol - Google Patents

Abstract

The present invention relates to a method for extracting decosinol and to a cosmetic composition comprising the decosinol, and more particularly, to a method for extracting decosinol with high efficiency and high purity from Angelica gigas, and a high purity deciche obtained by the method. It relates to a cosmetic composition comprising a knol.

Description

Extraction method of decocinole and cosmetic composition comprising the decosinol {METHOD OF EXTRACTING DECURSINOL AND COSMETIC COMPOSITION COMPRISING THE DECURSINOL}

The present invention relates to a method for extracting decosinol and to a cosmetic composition comprising the decosinol, and more particularly, to a method for extracting decosinol with high efficiency and high purity from Angelica gigas, and a high purity deciche obtained by the method. It relates to a cosmetic composition comprising a knol.

Recently, as the public's interest in human health and beauty has been greatly increased, research and development of functional materials using various natural products are continuously made. In particular, the skin, the largest organ of the human body, protects the body from external physical and chemical stimuli and maintains homeostasis such as humidity and body temperature. However, ageing or constant exposure to external stimuli accelerates skin aging, including damage to the skin and poor physiology. As the skin ages, the demand for quality of life increases due to natural phenomena or improvement of living standards that inevitably occur with age, and skin aging that has been increased due to various environmental factors. Countermeasures are urgently needed.

The most prominent change in the appearance of the skin accompanying such aging is wrinkles. Wrinkles occur on the face of the forehead, around the eyes, between the legs, and around the mouth, or on different parts of the body, such as the neck, neck, elbow, armpits, hands, and feet. Most wrinkles start to appear around 30 years of age, and as they age, their number, depth, and range increase.

Therefore, the development of a substance for delaying and suppressing skin aging has emerged as an important task in the cosmetic field, and a lot of research is being conducted. In recent years, the use of natural ingredients in cosmetics has been increasing rapidly, and various skin physiological activities on natural plant ingredients have been searched for, and substances having excellent skin aging inhibitory effects have been developed.

Functional raw materials based on such natural materials may include ginseng, Angelica, red ginseng, ginkgo, licorice, soybean, ganoderma lucidum, cinnamon, irises, peony, garlic, onion, yulmu, mugwort, green tea, pine needle extract, etc. The same natural ingredients are not only unstable by themselves, but also have a great problem in the stability of the cosmetics, such as precipitation of the contents, color change when applied to the cosmetics. In addition, when the content of the active ingredient contained in the natural product is not large, there is also a problem that there is a need for an extraction method having a commercially available efficiency.

Among these natural products, Angelica was found to have natural coumarin derivatives such as decusin, decosinol, nodakenin, and umbelliferon isolated from dried roots and fruits. It has been reported to paralyze the exhalation of the extraction and the cardiopulmonary movement, to lower blood pressure, respiratory depression, to excite decosin and to inhibit decosinol. However, in the case of the decosinol, the existing extraction method from Angelica gigas is low in yield and purity, and the conventional extraction method using an organic solvent has new high efficiency and efficiency due to problems such as human harmfulness, environmental toxicity, high cost and low selectivity. High purity environmentally friendly extraction methods are required, and new fields of application using them are required.

The technical problem to be achieved by the present invention is to provide an extraction method for separating the decansinol from the Angelica gigas in high purity and high efficiency.

Another technical problem to be achieved by the present invention is to provide a cosmetic composition comprising the decosinol as an active ingredient.

According to an aspect of the present invention,

A supercritical extraction step of obtaining a supercritical extract from pulverized Angelica dried using a supercritical extraction method;

A hydrolysis step of dissolving the supercritical extract in an organic solvent and then hydrolyzing by adding a base; And

It provides a decosinol extraction method comprising the step of removing the polar substance from the hydrolyzate and separating and purifying the decosinol from the obtained fraction.

The present invention to achieve the above other technical problem,

It provides a cosmetic composition comprising the decosinol as an active ingredient.

The present invention provides an environmentally friendly extraction method for extracting decosinol from sugar cane with high purity and high efficiency, and when the decosinol is used as a cosmetic composition, an improved skin wrinkle improvement effect is obtained.

1 is a graph showing the effect on decansinol cell survival of HDF (Human Dermal Fibroblast) according to the present invention.
Figure 2 is a graph showing the effect on the cell activity of HDF (Human Dermal Fibroblast) according to the concentration of decosinol according to the present invention.

According to an aspect of the present invention,

A supercritical extraction step of obtaining a supercritical extract from pulverized Angelica dried using a supercritical extraction method;

A hydrolysis step of dissolving the supercritical extract in an organic solvent and then hydrolyzing by adding a base; And

It provides a decosinol extraction method comprising the step of removing the polar substance from the hydrolyzate and separating and purifying the decosinol from the obtained fraction.

The present invention to achieve the above other technical problem,

It provides a cosmetic composition comprising the decosinol as an active ingredient.

Hereinafter, the present invention will be described in more detail.

Angelica , the main material of the present invention gigas ) is known as a blood donor, and its root is known as a traditional anticancer, antioxidant. Recently, a number of coumarin derivatives, which are considered to be the main active ingredients of Angelica gigas, have been isolated and identified, and many studies have been conducted on decosin and decosinol angelate.

The present invention provides a method for extracting decosinol with high purity and high efficiency from Angelica gigas, and the method for extracting decosinol according to the present invention is environmentally friendly, high yield and high efficiency by using a combination of supercritical extraction and alkali hydrolysis. Decacinol of Formula 1 is extracted.

≪ Formula 1 >

In the method for extracting decosinol according to the present invention, firstly, commercially available dried Angelica is finely pulverized, and then it is treated by supercritical extraction in a predetermined container, decursin and decosinol, which are active ingredients of Angelica Angelic acid (decursinol angelate) is extracted. The supercritical extraction method used here is an extraction method using a fluid containing carbon dioxide in a supercritical state to be carried out at a flow rate of 0.5 to 2L / min (at room temperature) at a temperature of 40 to 100 ℃ and a pressure of 3,000 to 7,000 psi Can be. If the supercritical extraction temperature is less than 40 ℃ it is difficult to obtain a sufficient extraction efficiency, if it exceeds 100 ℃ it is not preferable because of the economic benefits due to the excess temperature. In addition, when the supercritical extraction pressure is less than 3,000 psi, sufficient extraction efficiency cannot be obtained, and when it exceeds 7,000 psi, economical efficiency is lowered, which is not preferable. If the flow rate of the supercritical fluid is 0.5L / min, a sufficient extraction efficiency can not be obtained, and if it exceeds 2L / min, there is a problem that the economic efficiency is lowered.

 As a fluid containing carbon dioxide in a supercritical state used in the supercritical extraction method, pure carbon dioxide is used, or 70 to 97 parts of carbon dioxide and 3 to 30 parts of cosolvent; Alternatively, it is also possible to use a mixed fluid comprising 70 to 97 parts of carbon dioxide, 1 to 28 parts of lower alcohol and 2 to 10 parts of water. As the cosolvent, lower alcohols such as ethanol and methanol or normal hexane, ethyl acetate and the like can be used. Preferably, lower alcohols, in particular ethanol, are preferably used. The preferred volume of cosolvent is 3 to 30 parts by volume of cosolvent relative to 70 to 97 parts by weight of carbon dioxide, as described above. In addition, when using a lower alcohol as a co-solvent, the addition of a certain ratio of water makes it easier to extract highly polar substances, wherein the volume ratio is 70 to 97 parts of carbon dioxide, 1 to 28 parts of lower alcohol and water 2 To 10 parts by volume may be used.

As described above, the supercritical extract obtained by applying the supercritical extraction method to the Angelica gigas contains a large amount of deucin and decosinol angelate, which are the main components of Angelica gigas, and after dissolving the supercritical extract in an organic solvent, The base is added to the mixture and refluxed to perform alkali hydrolysis. Such alkali hydrolysis breaks down the ester bonds of the supercritical extract and increases the yield of decosinol.

As the organic solvent used for the alkali hydrolysis, an organic solvent which is generally used as a solvent can be used without limitation, but it is preferable to use a lower alcohol or a mixed solvent of lower alcohol and halogenated hydrocarbon. As the base used for the alkali hydrolysis, a general base can be used without limitation, but it is preferable to use a strong base such as potassium hydroxide or sodium hydroxide. The reflux treatment may be performed at a temperature of 40 to 100 ° C. for 10 hours to 100 hours, and it is preferable to check the generation of decosinol through TLC (Thin Layer Chromatography) during the reaction process. The product obtained by treating the supercritical extract by such alkali hydrolysis will include intermediate products and KOH in addition to a small amount of decusin, decosinol angelate and a large amount of decosinol.

Subsequently, the alkaline hydrolyzate is fractionated by fractionation with water and an organic solvent. By this fractionation process, KOH, which is a polar substance, is transferred to the water layer, and decusin and decosinol are transferred to the organic solvent layer. The obtained organic solvent layer is concentrated under reduced pressure to obtain an organic solvent fraction. As the organic solvent layer used in the fractionation process, various organic solvents can be used without limitation, but ethyl acetate (EtOAc) is preferably used.

Next, the desired decosinol can be separated from the organic solvent fraction, and examples of the separation method that can be used include column chromatography, and silica gel chromatography is preferable. Since the isolate may also contain other impurities, it is purified by removing the impurities by a method such as this separation process several times to obtain a high purity decosinol.

The high purity decosinol obtained at high efficiency may be added to the cosmetic composition as an active ingredient, and includes components commonly used in cosmetic compositions in addition to the decosinol, such as stabilizers, solubilizers, vitamins, pigments and flavorings. Conventional adjuvants such as, and carriers.

Cosmetic compositions comprising such decosinol as an active ingredient may have a variety of physiological activities, for example, it may exhibit an anti-wrinkle effect by preventing skin aging. In this case, the content of the decosinol in the cosmetic composition may be used in an amount of 0.003 to 0.015% by weight based on the total weight, preferably 0.004 to 0.012% by weight, most preferably 0.004 to 0.008% by weight.

Cosmetic compositions according to the invention, in particular cosmetic compositions for improving wrinkles may be prepared in any formulation commonly prepared in the art, for example, solutions, suspensions, emulsions, pastes, gels, creams, lotions, powders , Soaps, surfactant-containing cleansing, oils, powder foundations, emulsion foundations, wax foundations, sprays, and the like, but are not limited thereto. More specifically, it can be manufactured in the form of a soft lotion, a nutritional lotion, a nutritional cream, a massage cream, an essence, an eye cream, a cleansing cream, a cleansing foam, a cleansing water, a pack, a spray or a powder.

When the formulation of the present invention is a paste, cream or gel, an animal oil, vegetable oil, wax, paraffin, starch, tracant, cellulose derivative, polyethylene glycol, silicone, bentonite, silica, talc or zinc oxide may be used as the carrier component .

In the case where the formulation of the present invention is a powder or a spray, lactose, talc, silica, aluminum hydroxide, calcium silicate or polyamide powder may be used as a carrier component. Especially, in the case of a spray, a mixture of chlorofluorohydrocarbons, propane / Propane or dimethyl ether.

When the formulation of the present invention is a solution or an emulsion, a solvent, a dissolving agent or an emulsifying agent is used as a carrier component, and examples thereof include water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, , 3-butyl glycol oil, glycerol aliphatic ester, polyethylene glycol or sorbitan fatty acid esters.

In the case where the formulation of the present invention is a suspension, a carrier such as water, a liquid diluent such as ethanol or propylene glycol, a suspending agent such as ethoxylated isostearyl alcohol, polyoxyethylene sorbitol ester and polyoxyethylene sorbitan ester, Cellulose, aluminum metahydroxide, bentonite, agar or tracant, etc. may be used.

When the formulation of the present invention is an interfacial active agent-containing cleansing, the carrier component may include aliphatic alcohol sulfate, aliphatic alcohol ether sulfate, sulfosuccinic acid monoester, isethionate, imidazolinium derivative, methyltaurate, sarcosinate, fatty acid amide Ether sulfates, alkylamidobetaines, aliphatic alcohols, fatty acid glycerides, fatty acid diethanolamides, vegetable oils, lanolin derivatives, or ethoxylated glycerol fatty acid esters.

Hereinafter, the present invention will be described in more detail with reference to Examples. It is to be understood that the scope of the present invention is not limited by these examples in accordance with the gist of the present invention, and it is to be understood by those skilled in the art that the present invention is not limited thereto It will be obvious.

Example 1

3Kg of dried Angelica pulverized about 2mm in length and put into the container, the temperature in the container is maintained at 50 ℃, supercritical pressure is maintained at 300Kg _f / cm ² , carbon dioxide for 6 hours at a rate of 6.7kg per hour Extraction was performed three times to obtain 400 g of supercritical extract. The supercritical extract (400 g) was dissolved by adding methanol and CHCl ₃ , and then hydrolyzed by refluxing at 85 ° C. for 3 days by adding 10% KOH (1200 ml). From time to time, TLC was checked (normal hexane: EtOAc = 1: 1, R _f value of decosinol = 0.2) to confirm the degree of decosinol production. The obtained hydrolyzate was partitioned between water (2000 ml) and EtOAc (2000 ml X 4 times), and then the EtOAc layer was concentrated under reduced pressure to give EtOAc fraction (270 g).

Silica gel column chromatography (SiO ₂ : 800g, n -Hexane: EtOAc = 1: 1) was performed from the EtOAc fraction. The obtained eluate was confirmed by TLC ( n- Hexane: EtOAc = 1: 1), at which time fractions showing fluorescence absorption in blue at 254 and 365 nm in a UV lamp were concentrated under reduced pressure. The extract was purified several times (SiO ₂ cc, n -Hexane: EtOAc = 3: 1-> 2: 1-> 1: 1) to obtain high purity decosinol (50 g).

The compound was dark purple when colored with 10% aqueous sulfuric acid solution. Four olefine methine protons in the ¹ H-NMR spectrum [δ 6.07 (1H, d, J = 9.6 Hz), 6.64 (1H, s), 7.08 (1H, s), 7.48 (1H, d, J = 9.6 Hz)] signal and one oxidized methine signal was observed at δ 3.79 (1H, d, J = 4.8 Hz, J = 5.6 Hz). Allyl methylene and δ 1.29 (3H, s), δ 1.31 (at δ 2.75 (1H, dd, J = 5.6 Hz, J = 16.4 Hz), δ 3.01 (1H, dd, J = 4.8 Hz, J = 16.4 Hz) At 3H, s) two single methyl signals were observed. Therefore, this compound was assumed to be a coumarin series compound. ¹³ C-NMR spectra confirmed that the compound had 14 carbons, and 4 olefin quaternary carbons (δ 156.4, 153.7, 116.8, including olefin ketone carbon at δ 161.4). , 112.5) and four olefine methine carbons (δ 143.2, 128.8, 112.6, 104.3), two oxidized methine carbons (δ 78.2, 68.7), allyl methylene carbon ) (δ 30.5) and two single methyl carbons (δ 25.1, 21.9). Therefore, as a result of comparative analysis by combining ¹ H and ¹³ C-NMR, it was identified as decusinol.

Decosinol: white powder (CD ₃ OD); mp 178 [deg.] C; [α] _D +173.1 Hz (CHCl ₃ ); LC / MS m / z : 246.27 [M] ⁺ ; ¹ H-NMR (400 MHz, CD ₃ OD, δ) 1.29 (3H, s, CH3), 1.31 (3H, s, CH3), 2.75 (1H, dd, J = 5.6 Hz, J = 16.4 Hz, H- 4a '), 3.01 (1H, dd, J = 4.8 Hz, J = 16.4 Hz, H-4b'), 3.79 (1H, d, J = 4.8 Hz, J = 5.6 Hz, H-3 '), 6.07 ( 1H, d, J = 9.6 Hz, H-3), 6.64 (1H, s, H-8), 7.08 (1H, s, H-5), 7.48 (1H, d, J = 9.6 Hz, H-4 ); ¹³ C-NMR (100 MHz, CD ₃ OD, δ _C ) 161.40 (C-2), 156.44 (C-7), 153.70 (C-8a), 143.21 (C-4), 128.81 (C-5), 116.80 (C-6), 112.61 (C-3 ), 112.54 (C-4a), 104.36 (C-8), 78.26 (C-2 '), 68.75 (C-3'), 30.57 (C-4 '), 25.12 (CH ₃ ), 21.93 (CH ₃₎ )

Experimental Example 1: Evaluation of cell cytotoxicity against human dermal fibroblast (HDF)

Experimental cell preparation

Fibroblasts (human dermal fibroblast) were incubated for 24 hours in a T 75 culture flask using 5% DMEM medium, the cells were washed with PBS and removed from the culture dish using trypsin-EDTA to use as experimental cells. Cell counts were checked using a hemocytometer and cells were seeded at 1 × 10 ⁵ cells / well in 96 well plates and stabilized for 24 hours.

-Sample processing

Decacinol did not dissolve well in water, dissolved in 50% DMSO, and refrigerated. Dilution of the decosinol was carried out by diluting the sample dissolved in 50% DMSO in the DEME containing 5% FBS to each concentration, sufficiently dissolved using a vortex mixer, and then disinfected using a 0.2 μm syringe filter. It was. In order to evaluate the effect of DMSO on fibroblasts, a comparison was made with the same concentration of DMSO contained in the evaluation sample. The cytotoxicity was evaluated by diluting the decosinol to the concentration as shown in Table 1 below. The control group was compared by administering only PBS buffer.

Sample concentration / DMSO 1.000 /
0.500 0.500 /
0.250 0.250 /
0.125 0.125 /
0.064 0.064 /
0.032 0.032 /
0.016 0.016 /
0.008 0.008 /
0.004 0.004 /
0.002 0.002 /
0.001 DMSO 0.500 0.250 0.125 0.064 0.032 0.016 0.008 0.004 0.002 0.001

-Survival rate assessment

After performing the experiment, the existing medium was removed, and 90 μl fresh medium + 10 μl MTT solution (5 mg / ml) was added to each well, followed by incubation in a CO ₂ incubator at 37 ° C. for 2 hours. 100 μl of isopropanol-HCl (0.04 N) was added and shaken for 5 minutes to lyse the cells. Then, the OD ₅₆₅ value was measured at 565 nm of a microplate reader, and the degree of cell death by the test sample was obtained. The concentration of the sample and the concentration of the sample killing 50% of cells were determined.

Experimental Example 2: Evaluation of Cell Growth for Human Dermal Fibroblast (HDF)

- Sample Preparation

Decacinol did not dissolve well in water, dissolved in 50% DMSO, diluted to 100% viability obtained through cytotoxicity evaluation, and then used for refrigeration. Dilution of the decosinol was diluted to each concentration in DMEM (growth 0%) containing 0.5% FBS as shown in Table 2, dissolved sufficiently using a vortex mixer and then disinfected using a 0.2 μm syringe filter. It was.

Experimental cell preparation

Fibroblasts (human dermal fibroblast) were cultured for 24 hours in a T 75 culture flask using 5% DMEM medium, washed with PBS, and then removed from the culture dish using trypsin-EDTA to use as experimental cells. The number of cells was checked using a hemocytometer, and the cells were dispensed at 1 × 10 ⁵ cells / well in 12 well plates using 0.5% FBS DMEM (growth 0%) and stabilized for 24 hours.

-Sample processing

Treatment was performed at concentrations representing 100% survival rate obtained through cytotoxicity evaluation experiments, and survival rate was evaluated by setting DMEM medium containing 0.5% FBS as a control to evaluate only the effect by the sample.

Sample concentration
(Concentration of decosinol / DMSO concentration) 0.016 / 0.008 0.008 / 0.004 0.004 / 0.002 0.002 / 0.001

-Survival rate assessment

48 hours after the evaluation sample was processed, the existing medium was removed, 500 μl fresh medium + 60 μl MTT solution (5 mg / ml) was added to each well, and then cultured in a CO ₂ incubator at 37 ° C. for 2 hours. 100 μl of isopropanol-HCl (0.04 N) was added and shaken for 5 minutes to lyse the cells, and cell proliferation was evaluated by measuring the OD ₅₆₅ value at 565 nm of the microplate reader.

Result: Cell cytotoxicity assessment

Decacinol did not dissolve well in water and dissolved in 50% DMSO, but at concentrations of 0.032% or higher, 1.000%, 0.500%, 0.250%, 0.125%, 0.064%, this sample was not able to develop MTT and SR reagents. It was not possible to obtain a quantitative toxicological result, so the IC ₅₀ of decosinol was observed to be 0.250% in the microscope. This is because the IC ₅₀ of the safest raw material in the cosmetic material is formed at 1.000 to 0.500%, the cytotoxicity is stronger than this material, but it does not show the toxicity enough to cause irritation. As a result of the quantitative toxicity evaluation using the MTT assay, as shown in FIG. 1, the concentration indicating 100% cell survival of the evaluation sample was 0.016%.

-Result: cell growth evaluation

As shown in FIG. 2, no significant activity was observed on the cells at concentrations of 0.016%, which are non-toxic to Decacinol, and at 0.002%, which is low. The reason for this is that at 0.016%, the cells induced stress at 5% FBS DMEM, that is, at 0.5% FBS, where the concentration determined at the optimal state for cell growth was 0%. It is presumed that the percentage is due to the low concentration that does not affect cell proliferation. However, at 0.008% and 0.004%, they showed significant cell proliferation of 115% (+ 15%), respectively.

As described above, the cytotoxicity test and the cell proliferation evaluation showed that the wrinkle improvement effect was significant. Therefore, it can be seen that when decosinol is effectively formulated into a product, it can be used as a natural material of a new functional cosmetic having an important function in inducing cell proliferation and maintaining wrinkles and maintaining skin homeostasis.

In order to confirm that the decousinol has a skin wrinkle improvement effect, a cosmetic composition of various solubilizing and emulsifying formulations containing decosinol was prepared. The following prescription examples are for illustrating the cosmetic composition of the present invention, the composition of the present invention is not limited thereto.

The decosinol used in the preparation of the cosmetic composition of the following formulation example used the extract prepared in Example 1.

Preparation Example 1 Preparation of Soft Cosmetics (Skin Lotion)

According to the composition of Table 3 below, decocinol-containing softening water was prepared according to a conventional method.

ingredient Content (% by weight) Dekersinol 0.004 glycerin 5.0 1,3-butylene glycol 3.0 PEG 1500 1.0 Allantoin 0.1 DL-Panthenol 0.3 EDTA-2Na 0.02 Benzophenone-9 0.04 Sodium hyaluronate 5.0 ethanol 10.0 Octidodeces-16 0.2 Polysorbate 60 0.2 Preservative, fragrance, pigment a very small amount Distilled water Balance Sum 100

Preparation Example 2 Preparation of Converging Cosmetic Water

According to the composition of Table 4, a convergent longevity-containing decosinol was prepared according to a conventional method.

ingredient Content (% by weight) Dekersinol 0.004 glycerin 2.0 1,3-butylene glycol 2.0 Allantoin 0.2 DL-Panthenol 0.2 EDTA-2Na 0.02 Benzophenone-9 0.04 Sodium hyaluronate 3.0 ethanol 15.0 Polysorbate 60 0.3 Location Hagel extract 2.0 Citric acid a very small amount Preservative, fragrance, pigment a very small amount Distilled water Balance Sum 100

Preparation Example 3 Preparation of Nutrients

According to the composition of Table 5, decosinol-containing nutrient longevity was prepared according to a conventional method.

ingredient Content (% by weight) Dekersinol 0.004 Glyceryl Stearate SE 1.5 Stearyl alcohol 1.5 lanolin 1.5 Polysorbate 60 1.3 Sorbitan stearate 0.5 Hardened vegetable oil 1.0 Mineral oil 5.0 Squalane 3.0 Trooctanoin 2.0 Dimethicone 0.8 Tocopheryl acetate 0.5 Carboxyvinyl Polymer 0.12 glycerin 5.0 1,3-butylene glycol 3.0 Sodium hyaluronate 5.0 Triethanolamine 0.12 Preservative, fragrance, pigment a very small amount Distilled water Balance Sum 100

Preparation Example 4 Preparation of Nutritional Cream

According to the composition of Table 6, nutrition cream containing decosinol was prepared according to a conventional method.

ingredient Content (% by weight) Dekersinol 0.004 Lipophilic monostearate 2.0 Stearyl alcohol 2.2 Stearic acid 1.5 Wax 1.0 Polysorbate 60 1.5 Sorbitan stearate 0.6 Hardened vegetable oil 1.0 Squalane 3.0 Mineral oil 5.0 Trioctanoine 5.0 Dimethicone 1.0 Sodium magnesium silicate 0.1 glycerin 5.0 Betaine 3.0 Triethanolamine 1.0 Sodium hyaluronate 4.0 Preservative, fragrance, pigment a very small amount Distilled water Balance Sum 100

Preparation Example 5 Preparation of Massage Cream

Massage creams containing deckusinol according to the composition of Table 7 were prepared according to a conventional method.

ingredient Content (% by weight) Dekersinol 0.004 Lipophilic Monostearineglycerin 1.5 Stearyl alcohol 1.5 Stearic acid 1.0 Polysorbate 60 1.5 Sorbitan stearate 0.6 Isostearyl isostearate 5.0 Squalane 5.0 Mineral oil 35.0 Dimethicone 0.5 Hydroxyethylcellulose 0.12 glycerin 6.0 Triethanolamine 0.7 Preservative, fragrance, pigment a very small amount Distilled water Balance Sum 100

Preparation Example 6 Preparation of Essence

According to the composition of Table 8 below, an essence containing decosinol was prepared according to a conventional method.

ingredient Content (% by weight) Dekersinol 0.004 glycerin 10.0 Betaine 5.0 PEG 1500 2.0 Allantoin 0.1 EL-panthenol 0.3 EDTA-2Na 0.02 Benzophenone-9 0.04 Hydroxyethylcellulose 0.1 Sodium hyaluronate 8.0 Carboxy vinyl polymer 0.2 Triethanolamine 0.2 Octyldodecanol 0.3 Octyldodec-16 0.4 ethanol 6.0 Preservative, fragrance, pigment a very small amount Distilled water Balance Sum 100

Comparative Production Example 1

In order to confirm the skin wrinkle improvement effect of the composition of this invention more reliably, the cosmetic composition of the comparative manufacture example 1 was manufactured. According to the composition of Table 9, Comparative Formulation Example 1 of the additive-free composition containing no decosinol in the composition of the nutrition cream of Table 6 was prepared according to a conventional method.

ingredient Content (% by weight) Lipophilic monostearate 2.0 Stearyl alcohol 2.2 Stearic acid 1.5 Wax 1.0 Polysorbate 60 1.5 Sorbitan stearate 0.6 Hardened vegetable oil 1.0 Squalane 3.0 Mineral oil 5.0 Trioctanoine 5.0 Dimethicone 1.0 Sodium magnesium silicate 0.1 glycerin 5.0 Betaine 3.0 Triethanolamine 1.0 Sodium hyaluronate 4.0 Preservative, fragrance, pigment a very small amount Distilled water Balance Sum 100

Experimental Example 3:

In order to confirm the wrinkle improvement effect of the cosmetics containing the decosinol according to the present invention, 60 healthy Korean women (age distribution 30-40 years old) were evaluated through actual use test. After dividing the subjects randomly into three groups of 20 people each day, the nutrition cream of Preparation Example 4 containing decosinol, and the nutrition cream of Decocinol except the composition of Preparation Example 4 (Comparative Preparation Example 1) daily After washing twice in the morning and evening, the appropriate amount of cream was applied continuously for two months centering around the eyes. Wrinkle improvement effect of each subject was evaluated through visual observation and the results are shown in Table 10 below.

division Excellent wrinkle improvement Wrinkle improvement effect slightly No wrinkle improvement Effective rate (%) Production Example 4 15 5 0 95.0 Comparative Preparation Example 1 4 3 13 35.0

According to the results of the experiment, Preparation Example 4 containing the decosinol was much higher wrinkle improvement than Comparative Preparation Example 1. In addition, skin irritation could not be observed in the subjects coated with the cosmetic composition of the present invention.

Claims (6)

Preparing a donkey dry matter;
Supercritical extraction of the Angelica dry matter at a flow rate of 0.5 to 2 L / min;
Dissolving the Angelica supercritical extract in an organic solvent which is a lower alcohol selected from the group consisting of methanol and ethanol, or a mixture of the lower alcohol and a halogenated hydrocarbon;
Hydrolyzing by adding a base to the Angelica supercritical extract dissolved in the organic solvent;
Removing the polar material from the hydrolyzate to obtain a fraction; and
Method for producing a cosmetic composition for improving skin wrinkles comprising the step of separating and purifying decosinol from the fraction using column chromatography.
The method of claim 1,
Wherein the supercritical extraction step is performed at a flow rate of 0.5 to 2 L / min (at room temperature) at a temperature of 40 to 100 ° C. and a pressure of 3,000 to 7,000 psi.
The method of claim 1,
In the supercritical extraction step, the fluid containing carbon dioxide in a supercritical state uses pure carbon dioxide, or 70 to 97 parts of carbon dioxide and 3 to 30 parts of cosolvent; Or a mixed fluid comprising 70 to 97 parts of carbon dioxide, 1 to 28 parts of lower alcohol, and 2 to 10 parts of water.
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