KR20160081161A - Skin external composition for moisturizing or whitening the skin comprising compound K and acetic acid 16-hydroxy-octadeca-9,17-diene-12,14-diynyl ester - Google Patents

Abstract

The present invention relates to a skin composition for moisturizing or whitening skin. More particularly, the skin composition recovers a damaged skin barrier function by comprising compound K and acetic acid 16-hydroxy-octadeca-9,17-diene-12,14-diynyl ester as effective components, and has enhanced skin moisturizing ability. Also, the skin composition can alleviate symptoms of pigmentation such as melasma and freckles, or dullness of the skin, and can make the color of the skin look uniform and bright.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a skin external composition for skin moisturizing or whitening comprising a compound K and 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester acetic acid. acid 16-hydroxy-octadeca-9,17-diene-12,14-diynyl ester}

More particularly, the present invention relates to a composition for skin moisturizing or whitening, which comprises Compound K and 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester acetic acid as an active ingredient, The present invention relates to a composition for external application for skin which not only improves barrier function and increases skin moisturizing power but also improves pigmentation symptoms such as spots and freckles or dullness of skin and makes skin color uniform and bright.

Skin plays a very important role as a barrier function to protect individuals from the outside. The barrier function is a protection function for protecting against various stimuli (chemicals, air pollutants, dry environment, ultraviolet rays, etc.) from the outside and excessive divergence of water in the body through the skin. Such protection function is a function of protecting the stratum corneum The function can be maintained only when it is normally formed.

The outermost stratum corneum (horney layer) of the epidermis is formed from keratinocytes, and consists of keratinocytes with complete differentiation and a surrounding lipid layer (Marcelo CL et al . , J. Invest. Dermatol . 80 , pp 37-44, 1983).

The keratinocyte is a characteristic cell in which basal cells continuously proliferating in the lowest epidermis undergo a stepwise change in morphology and function and are elevated to the surface of the skin. After a certain period of time, And the new keratinocyte replaces its function. This repetitive sequence of changes is called "epidermal cell differentiation" or "keratinization".

In addition, during keratinization, keratinocytes form natural moisturizing factors (NMF) and intercellular lipids (ceramides, cholesterol, fatty acids) and form stratum corneum, which gives firmness and flexibility to the stratum corneum, barrier function.

Such stratum corneum can easily lose its function due to environmental factors such as excessive washing, bathing and other lifestyle factors, dry air pollutants, and endogenous diseases such as atopic skin and senile skin. In fact, Due to the increasing number of factors, dry skin symptoms and their complaints have been increasing recently.

Therefore, in order to maintain proper skin moisture, various studies have been made to supply water from the outside or to prevent water loss from the body. Various moisturizers having moisture retention ability have been developed. As a skin moisturizing agent, it is common to use a substance capable of increasing water retention in the stratum corneum such as ceramide and essential fatty acid and lipid complex (Rawlings AV et al . , J. Invest. Dermatol. , 5, pp731- 741, 1994).

However, recently, the risk factors for skin are increasing, and changes in dietary patterns slow down the generation and decline of the stratum corneum, and the function of the keratinocyte is reduced, so that the amount of the moisturizing factor and lipid in the stratum corneum is decreased, There is an increasing trend in people with skin that can not function as a skin barrier. Such breakdown of the skin barrier function causes various skin diseases such as dry skin, atopic dermatitis, contact dermatitis and psoriasis. Such diseases can be expected to be alleviated by moisturizing agents having a conventional moisture retention function but it is difficult to achieve fundamental healing.

In addition, human skin color is determined by various factors such as the activity of melanocyte making melanocyte, the distribution of blood vessels, the thickness of skin, and the presence or absence of pigment inside and outside the body, such as carotenoids and bilirubin. In particular, melanin, which is produced by the action of various enzymes such as tyrosinase in melanocytes, is the most important factor. The formation of melanin pigment is affected by environmental factors such as genetic factors, hormonal secretion, physiological factors such as stress, and ultraviolet irradiation. Melanin is present in the skin and protects the body from ultraviolet rays, but it is known that melanin is overproduced, thereby promoting pigmentation and aging of the skin and leading to skin cancer induction. (Ascorbic acid), kojicadcid, arbutin, hudroquinone, and hyaluronic acid to treat or relieve excessive melanin pigmentation caused by skin pigmentation abnormalities and ultraviolet exposure. Glutathione or a derivative thereof and a substance having inhibitory activity against tyrosinase have been used in cosmetics or medicines and they have been used in the fields of inadequate whitening effect, safety of skin, and stability in formulations And its use is limited due to problems.

On the other hand, interest in the components extracted from ginseng, particularly polyyne, has been increasing as a component separated from natural materials in recent years. Among them, paracinol, paraxidol, paraxyltriol and the like as polyacetylene components have cytotoxicity against cancer cells and thus have anticancer effects.

However, the research on the polyacetylene component is still insignificant. In particular, there has not been reported remarkable research results on the efficacy shown in relation to the skin condition improvement besides the anticancer effect and the synergistic effect by the combination with other ingredients.

Korean Patent Laid-Open No. 10-2012-0083943 (published on July 27, 2012)

The present invention relates to a composition having improved skin moisturizing ability and a skin barrier improvement effect as well as excellent skin whitening effect by containing Compound K in combination with 16-hydroxy-octadeca-9,17-dien-12,14-dienyl ester acetic acid And to provide the above objects.

In order to accomplish the above object, the present invention provides a compound K represented by the following formula 1: And a 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester acetic acid represented by the following formula (2) as an active ingredient.

The composition of the present invention not only exhibits an effect of restoring damaged skin barrier function and increasing skin moisturizing power but also exhibits excellent skin regeneration effect, and is a composition for moisturizing skin, strengthening skin barrier function and inducing differentiation of dermal keratinocyte. , Atopic dermatitis, contact dermatitis, psoriasis, and the like. In addition, the composition of the present invention provides excellent skin whitening effect, thereby reducing pigmentation symptoms such as stain and freckles, improving skin dullness, and making skin color uniform and bright.

The composition according to the present invention can effectively improve skin moisturizing power and skin whitening by containing Compound K and 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester acetic acid as an active ingredient.

The compound K used in the present invention is a compound having a structure of the following formula 1 and a molecular weight of 622.88.

[Chemical Formula 1]

The compound K used in the present invention may be extracted from plants or may be synthesized according to methods known in the art or commercially available ones may be used. Compound K can also be obtained from ginseng extract. The type of ginseng to be used at this time is not particularly limited, and ginseng, red ginseng, white ginseng, taegeuk ginseng and ginseng can be used. In addition, the ginseng extract is not only contained in the leached liquid obtained by leaching and transferring from ginseng but also contained in the concentrate obtained by partially or completely concentrating the leach solution or in the slump, premix, regular season, liquid extract and ginseng prepared by drying the concentrate again It contains all of the plant itself as well as chemicals that exert the main effect. Extracts from all parts of ginseng such as stem, root, leaf, flower, and fruit are available and are not limited to any particular part of the extract. Also, a known method can be used as a method of extracting the compound K from the ginseng extract.

Specifically, the compound K can be isolated from ginseng after preparing ginseng extract from water or an organic solvent by a method well known in the art. The organic solvent used in the present invention may be selected from the group consisting of ethanol, methanol, butanol, ether, ethyl acetate, chloroform and a mixed solvent of these organic solvents and water, preferably 80% ethanol. At this time, the extraction temperature is preferably 10 to 80 ° C, and the extraction can be performed for 3 to 24 hours. If the extraction temperature and the extraction time are exceeded, the extraction efficiency may be deteriorated or the component may be changed.

The 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester acetic acid used in the present invention has a molecular weight of 316, a (Z) -16- It is also referred to as Roxy-9,17-octadecadien-12,14-dienyl acetate ((Z) -16-hydroxy-9,17-octadecadiene-12,14-diynyl acetate).

(2)

The composition according to the present invention may contain the compound K in an amount of 0.001 to 20% by weight, preferably 0.1 to 10% by weight, based on the total weight of the composition. The composition according to the present invention may further contain 0.001 to 20% by weight, preferably 0.1 to 10% by weight, of 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester acetic acid, By weight. If the content of the active ingredient is less than the above-mentioned range, it is difficult to expect the efficacy and the effect of the above-mentioned ingredients. If the content exceeds the above content range, there is a problem of skin stability or shape.

Also preferably, the composition of the present invention contains compound K and 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester acetic acid in a weight ratio of 1: 1 to 1: 4.

The composition according to the present invention can be used for enhancing the skin barrier function and inducing the differentiation of dermal keratinocytes, and is a composition for preventing or improving skin dryness, atopic dermatitis, contact dermatitis or psoriasis caused by imperfections of epidermal differentiation Can be usefully used.

Also, the composition according to the present invention is excellent in the ability to recover damaged skin barrier and increase skin moisture content, and can be used as a composition for skin regeneration.

In addition, the composition according to the present invention effectively inhibits the production of melanin, thereby providing an excellent whitening effect, thereby improving pigmentation symptoms such as spots and freckles or dullness of the skin, and making the skin color uniform and bright.

The composition of the present invention may be formulated as an external preparation for skin, in particular as a cosmetic composition, and may be formulated containing a cosmetically or dermatologically acceptable medium or base. In addition, the composition of the present invention can be provided in all formulations suitable for topical application, for example, as a solution, an emulsion obtained by dispersing an oil phase in an aqueous phase, an emulsion obtained by dispersing a water phase in an oil phase, a suspension, a microemulsion, Gels, powders, pastes, foams or aerosol compositions of the present invention may be provided in the form of microgranules or ionic (liposomes) and non-ionic follicular dispersants, solids, gels, powders, pastes, foams or aerosol compositions. Specifically, the composition of the present invention may be provided in the form of a cream, a skin, a lotion, a powder, an ointment, a spray or a cone stick. Compositions of such formulations may be prepared according to conventional methods in the art.

In addition, the composition of the present invention may contain a skin absorption promoting substance to increase the skin improving effect.

In addition, the composition according to the present invention may contain, in addition to the above-mentioned substances, other ingredients which can give a synergistic effect to the main effect, to the extent that the main effect is not impaired. The composition according to the present invention may further comprise a humectant, an emollient, an ultraviolet absorber, an antiseptic, a bactericide, an antioxidant, a pH adjuster, an organic or inorganic pigment, a perfume, a cold agent or a limiting agent. The compounding amount of the above components can be easily selected by a person skilled in the art within the range not impairing the object and effect of the present invention, and the amount thereof may be from 0.01 to 5% by weight, specifically from 0.01 to 3% by weight based on the total weight of the composition .

In addition, the composition of the present invention can be formulated as a pharmaceutical composition. When the composition according to the present invention is applied to medicines, it may be formulated into oral, parenteral or parenteral dosage forms in solid, semi-solid or liquid form by adding an inorganic or organic carrier compatible with the active ingredient used in the present invention , The pharmaceutical composition according to the present invention may be administered orally, parenterally, rectally, topically, transdermally, intravenously, intramuscularly, intraperitoneally, subcutaneously, and the like.

Examples of the formulations for oral administration include tablets, pills, granules, capsules, powders, fine granules, powders, emulsions, syrups and pellets. In addition, the formulations for parenteral administration include injections, drops, ointments, lotions, sprays, suspensions, emulsions, suppositories, and the like. The composition according to the present invention can be easily formulated into an active ingredient by carrying out the composition according to a conventional method. In this case, a surfactant, excipient, coloring agent, spice, preservative, stabilizer, buffer, suspending agent, have.

The dosage of the active ingredient of the pharmaceutical composition of the present invention will vary depending on the age, sex, body weight, pathological condition and severity of the subject to be treated, route of administration, or judgment of the prescriber. Determination of the appropriate dose based on these factors is well within the level of ordinary skill in the art and its daily dose is, for example, from 0.1 mg / kg / day to 100 mg / kg / day, more specifically from 5 mg / kg / day to 50 mg / / Day, but is not limited thereto.

Hereinafter, the present invention will be described in more detail with reference to Examples. It is to be understood by those skilled in the art that these embodiments are only for illustrating the present invention and that the scope of the present invention is not construed as being limited by these embodiments.

[Reference Example 1] Preparation of compound K

Compound K for testing the efficacy of the composition of the present invention was purchased from Ambo Research Institute (Korea).

Referential Example 2 Preparation of 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester acetic acid

The 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester acetic acid used to test the efficacy of the composition of the present invention was purchased from Cosvision (Korea).

[Test Example 1] Measurement of promoting effect of keratinocyte differentiation

In order to examine the differentiation promoting effect of the keratinocytes of the components used in the present invention, the amount of corned envelope (CE) generated upon differentiation of keratinocytes was measured by absorbance as described below.

First, horny cells (HEK; Lonza, NHEK-Neonatal Normal Human Epidermal Keratinocytes, Pooled) isolated from the epidermis of a newborn baby were placed in a culture flask and adhered to the bottom. After compound K of Reference Example 1 and 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester acetic acid of Reference Example 2 were treated at the concentrations shown in the following Table 1, Lt; RTI ID = 0.0 > 70-80% < / RTI > At this time, low calcium (0.03 mM) and high calcium (1.2 mM) treatment groups were negative control and positive control, respectively. Then, the cultured cells were harvested, washed with PBS (Phosphate buffered saline), and then suspended in 10 mM Tris-HCl buffer (Tris-HCl, pH 7.4) containing 2% SDS (sodium dodecyl sulfate) and 20 mM DTT (Dithiothreitol) pH 7.4) was added, sonication, boiling, and centrifugation. The precipitate was suspended again in 1 ml of PBS and the absorbance at 340 nm was measured. Separately, a part of the solution after the sonication was taken to measure the protein content and used as a standard in evaluating the degree of cell differentiation. The results are shown in Table 1 below.

Test substance The ability to differentiate in keratinocytes (%) Low calcium (0.03 mM) solution
(Negative control) 100 High calcium (1.2 mM) solution
(Positive control group) 210 Compound K (3 ppm)
Dien-12,14-dienyl ester acetic acid (2 ppm) 242 Compound K (2.5 ppm)
Diene-12,14-dienyl ester acetic acid (2.5 ppm) 304 Compound K (1.7 ppm)
Diene-12,14-dienyl ester acetic acid (3.3 ppm) 300 Compound K (1.25 ppm)
Diene-12,14-dienyl ester acetic acid (3.75 ppm) 298 Compound K (1 ppm)
Dien-12,14-dienyl ester acetic acid (4 ppm) 295 Compound K (5 ppm) 295 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester acetic acid (5 ppm) 212

As shown in Table 1, when the compound K and 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester acetic acid were treated together, the compound K or It can be confirmed that it exhibits remarkably excellent differentiation-promoting ability of keratinocytes as compared with the case of treating with 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester acetic acid alone.

Further, from the above results, it was found that when Compound K and 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester acetic acid were used in combination at a ratio of 1: 1 to 1: 4, It can be confirmed that synergistic effect can be shown in the promotion of differentiation.

[Test Example 2] Measurement of skin barrier function recovery effect

In order to measure the effect of the components used in the composition of the present invention on the recovery of damaged skin barrier function due to skin damage, the following experiment was conducted. Ten adult males and females were divided into six groups of Formulation Examples 1 and 2 and Comparative Formulation Examples 1 to 4, which were prepared by using the tape stripping method to damage the skin barrier, (TWEL) was measured and compared with Vapometer (Delfin, Finland) once a day for 7 days. Comparative Formulation Example 1 is a vehicle as a negative control, Comparative Formulation Example 2 is a comparative control containing only Compound K of Reference Example 1, Comparative Formulation Example 3 is 16-hydroxy- Diene-12,14-dienyl ester acetic acid. Comparative Formulation Example 4 is a comparative control containing compound K and 16-hydroxy-octadec-9,17-diene-12,14- Dienyl ester acetic acid in a weight ratio of 3: 2. The experimental results are shown in Table 3 below. The results in Table 3 were compared before treatment before barrier damage and after treatment before barrier damage on the basis of 100%.

Compounding ingredient Formulation Example 1 Formulation Example 2 Comparative Formulation Example 1 Comparative Formulation Example 2 Comparative Formulation Example 3 Comparative Formulation Example 4 Purified water 69 69 70 69 69 69 Propylene glycol 30 30 30 30 30 30 Compound K 0.5 0.2 - One - 0.6 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester Acetic acid 0.5 0.8 - - One 0.4

Test group TWEL Change (%) Before processing 1 day 2 days 3 days 4 days 5 days 6 days Formulation Example 1 100 130 129 124 120 114 110 Formulation Example 2 100 128 127 122 118 113 108 Comparative Formulation Example 1 100 121 112 98 70 62 43 Comparative Formulation Example 2 100 127 129 123 117 111 109 Comparative Formulation Example 3 100 123 118 111 110 108 105 Comparative Formulation Example 4 100 124 123 114 111 108 105

As can be seen from the above Table 3, when the compound K and the 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester acetic acid were treated together, K or 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester acetic acid, the rate of transdermal water loss returned to normal and the barrier damage was recovered at a rapid rate have.

[Referential Example 3] Formulation Examples 3 to 4 and Comparative Formulation Examples 5 to 8

Nutritive creams were prepared according to the composition of Table 4 below in a conventional manner (unit: wt%).

Compounding ingredient Formulation Example 3 Formulation Example 4 Comparative Formulation Example 5 Comparative Formulation Example 6 Comparative Formulation Example 7 Comparative Formulation Example 8 Purified water To 100 To 100 To 100 To 100 To 100 To 100 Compound K 0.25 0.1 - 0.5 - 0.3 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester Acetic acid 0.25 0.4 - - 0.5 0.2 Vegetable hydrogenated oil 1.50 1.50 1.50 1.50 1.50 1.50 Stearic acid 0.60 0.60 0.60 0.60 0.60 0.60 Glycerol stearate 1.00 1.00 1.00 1.00 1.00 1.00 Stearyl alcohol 2.00 2.00 2.00 2.00 2.00 2.00 Polyglyceryl-10pentastearate and behenyl alcohol and sodium stearoyl lactylate 1.00 1.00 1.00 1.00 1.00 1.00 Arachidyl behenyl alcohol & arachidyl glucoside 1.00 1.00 1.00 1.00 1.00 1.00 Cetylaryl Alcohol and Cetearyl Glucoside 2.00 2.00 2.00 2.00 2.00 2.00 PEG-100 Stearate & Glycerololate & Propylene Glycol 1.50 1.50 1.50 1.50 1.50 1.50 Caprylic / Carrick Triglyceride 11.00 11.00 11.00 11.00 11.00 11.00 Cyclomedicone 6.00 6.00 6.00 6.00 6.00 6.00 Preservative, incense Suitable amount Suitable amount Suitable amount Suitable amount Suitable amount Suitable amount Triethanolamine 0.1 0.1 0.1 0.1 0.1 0.1

[Test Example 3] Measurement of skin moisturizing effect

In order to measure the effect of the ingredients used in the composition of the present invention on the skin moisturizing effect, Formulations 3 to 4 and Comparative Formulations 5 to 8 were used and evaluated as follows.

Sixty male and female adults in the 40s and 50s classified as dry skin were divided into 6 groups of 10 persons for each of the six groups of Formulation Examples 3 to 4 and Comparative Formulation Examples 5 to 8, and the nutritional cream was applied twice daily for 4 weeks to the face . (24 ° C, relative humidity 40%) after 1 week, 2 weeks, and 4 weeks after application, and after 2 weeks (total 6 weeks) (Corneometer CM825, C + K Electronic Co., Germany). The results are shown in Table 5 below. The results in Table 5 are based on the skin moisture meter measured just before the start of the test, and the increase in the measured value after a certain period of treatment is expressed as a percentage.

Test group Moisture growth rate (%) 1 week Two weeks 4 weeks 6 weeks Formulation Example 3 33 36 39 36 Formulation Example 4 34 37 40 37 Comparative Formulation Example 5 30 32 32 15 Comparative Formulation Example 6 31 33 36 33 Comparative Formulation Example 7 32 35 34 32 Comparative Formulation Example 8 31 34 35 32

The results of Table 5 indicate that when Comparative Formulation Example 5 was applied, the moisture increase rate was about 30% until 4 weeks of application, but after the application was stopped, the amount of skin water decreased sharply and the compound K Comparative Formulation Containing Independently Comparative Formulation Example 6 containing only 6 or 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester acetic acid had a skin moisture increase rate It stayed at 30%. On the other hand, when Formulation Examples 3 and 4 containing both Compound K and 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester acetic acid were applied, by the synergistic effect of these two components It can be confirmed that the skin moisture increase rate is 35% or more even after the application is stopped. Thus, it can be seen that the composition of the present invention containing the compound K and 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester acetic acid has excellent skin moisturizing effect.

[Test Example 4] Inhibitory effect on melanin formation by B16 / F10 melanoma cells

The B16 / F10 melanoma used in this test example is a mouse-derived cell line, and is a cancer cell caused by malignant cell which secretes a melanin pigment called melanin. During the artificial incubation of these cells, the test material was treated to compare the degree of decrease in melanin production. The B16 / F10 melanoma used in this test was purchased from Korean Cell Line Bank (KCLB No: 8008).

Melanin biosynthesis inhibitory effect of B16 / F10 melanoma was measured as follows. B16 / F10 melanoma cells were seeded in a 6-well plate at 5 × 10 ⁵ cells / well and cultured in DMEM containing 10% FBS (fetal bovine serum) for 24 hours in a 5% CO ₂ incubator (MCO-20AIC, Dulbecco ' s Modified Eagle ' s Medium). The compound K of Reference Example 1 and the 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester acetic acid of Reference Example 2 as the test substance are added to a fresh DMEM medium without FBS in the following Table 6 And added for 72 hours. After treatment with trypsin-EDTA, the cells were separated by centrifugation, and melanin was dissolved at 95 ° C in 1N NaOH containing DMSO. Absorbance was measured at 405 nm using an ELISA reader (DIbiotech, Korea). Cells to which the test substance was not added were used as a control group, and the melanin formation inhibition degree of each test substance was measured by comparing with the melanin content in the control group. The inhibition rate of melanin production was calculated according to Equation (1) and the results are shown in Table 6.

Test substance Melanin inhibition rate (%) Control group (no addition) 0 Kojic acid 53 Compound K (0.05 wt%) + 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester acetic acid (0.05 wt% 48 Compound K (0.02 wt%) + 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester acetic acid (0.08 wt% 46 Compound K (0.1% by weight) 44 Dien-12,14-dienyl ester acetic acid (0.1% by weight) was added to a solution of 16-hydroxy-octadeca- 42 Compound K (0.06 wt.%) + 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester acetic acid (0.04 wt.%) 43

The results in Table 6 show that Compound K or 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester acetic acid, when treated with Compound K, , And 17-diene-12,14-dienyl ester acetic acid, the melanin production inhibition rate is higher than that in the case of using only 17-diene-12,14-dienyl ester acetic acid. In particular, when the combination ratio is used according to the present invention, It can be confirmed that it represents the generation effect.

[Test Example 5] Skin tone improvement effect

In order to examine the effect of the ingredients used in the composition of the present invention on the improvement of skin tone, 60 subjects were divided into 6 groups of 10 persons, and the subjects of each group were given Formulations 3 to 4 and Comparative Formulations 5 to 8 (1 week / day application, total 1 week), and the degree of skin tone improvement was evaluated using Facial Stage DM-3 (Moritex, Japan). The improvement rate of the skin tone was determined by determining the brightness and color change value of the skin from the brightness and color measurement values of the skin, and the average value of the results was obtained and is shown in Table 7 below. The larger the change in brightness and color, the better the skin tone.

Test substance Skin tone improvement rate (%) brightness Color Formulation Example 3 17 16 Formulation Example 4 16 15 Comparative Formulation Example 5 5 5 Comparative Formulation Example 6 15 12 Comparative Formulation Example 7 13 12 Comparative Formulation Example 8 14 13

The results in Table 7 show that Compound K or 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester acetic acid, when treated with Compound K, , And 17-diene-12,14-dienyl ester acetic acid alone, the skin tone improvement rate is increased. In particular, when the combination ratio is used according to the present invention, melanin production Effect can be confirmed.

Hereinafter, formulation examples of the composition according to the present invention will be described. However, the pharmaceutical composition and the cosmetic composition can be applied to various formulations, and the present invention is not limited thereto but is specifically described.

[Formulation Example 1] Lotion

Lotions are prepared according to a conventional method with the composition shown in Table 8 below.

Content (% by weight) Compound K 1.0 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester Acetic acid 1.0 glycerin 3.0 Butylene glycol 2.0 Propylene glycol 2.0 Carboxyvinyl polymer 0.1 PEG 12 nonyl phenyl ether 0.2 Polysorbate 80 0.4 ethanol 10.0 Triethanolamine 0.1 Preservative, coloring, fragrance Suitable amount Purified water Balance

[Formulation Example 2] Nourishing cream

Nutrition cream is prepared according to a conventional method with the composition shown in Table 9 below.

Content (% by weight) Compound K 1.0 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester Acetic acid 1.0 Polysorbate 60 1.5 Sorbitan sesquioleate 0.5 PEG 60 hardened castor oil 2.0 Liquid paraffin 10.0 Squalane 5.0 Caprylic / caproic triglyceride 5.0 glycerin 5.0 Butylene glycol 3.0 Propylene glycol 3.0 Triethanolamine 0.2 Preservative, coloring, fragrance Suitable amount Purified water Balance

[Formulation Example 3] Massage cream

A massage cream is prepared according to a conventional method with the composition shown in Table 10 below.

Content (% by weight) Compound K 0.5 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester Acetic acid 0.5 Wax 10.0 Polysorbate 60 1.5 PEG 60 hardened castor oil 2.0 Sorbitan sesquioleate 0.8 Liquid paraffin 40.0 Squalane 5.0 Caprylic / capric triglyceride 4.0 glycerin 5.0 Butylene glycol 3.0 Propylene glycol 3.0 Triethanolamine 0.2 Preservative, coloring, fragrance Suitable amount Purified water Balance

[Formulation Example 4] Pack

A pack is prepared according to a conventional method with the composition shown in Table 11 below.

Content (% by weight) Compound K 0.5 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester Acetic acid 0.5 Polyvinyl alcohol 13.0 Sodium carboxymethylcellulose 0.2 glycerin 5.0 Allantoin 0.1 ethanol 6.0 PEG 12 nonyl phenyl ether 0.3 Polysorbate 60 0.3 Preservative, coloring, fragrance Suitable amount Purified water Balance

[Formulation Example 5] Gel

A gel is prepared according to a conventional method with the composition shown in Table 12 below.

Content (% by weight) Compound K 0.25 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester Acetic acid 0.25 Ethylenediamine sodium acetate 0.05 glycerin 5.0 Carboxyvinyl polymer 0.3 ethanol 5.0 PEG 60 hardened castor oil 0.5 Triethanolamine 0.3 Preservative, coloring, fragrance Suitable amount Purified water Balance

[Formulation Example 6] Ointment

Ointment was prepared by a conventional method with the composition shown in Table 13 below.

Content (% by weight) Compound K 0.05 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester Acetic acid 0.05 glycerin 8.0 Butylene glycol 4.0 Liquid paraffin 15.0 Beta Glucan 7.0 Carbomer 0.1 Caprylic / capric triglyceride 3.0 Squalane 1.0 Cetearyl glucoside 1.5 Sorbitan stearate 0.4 Cetearyl alcohol 1.0 Wax 4.0 Preservative, coloring, fragrance Suitable amount Purified water Balance

[Formulation Example 7] Soft capsule

0.0013 g of Compound K, 0.0013 g of 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester acetic acid, 0.0025 g of vitamin C, 2 mg of palm oil, 8 mg of palm kernel oil, , And 400 mg / capsule was filled according to a conventional method to prepare a soft capsule.

[Formulation Example 8] Tablets

0.0013 g of Compound K, 0.0013 g of 16-hydroxy-octadec-9,17-diene-12,14-dienyl ester acetic acid, 0.0025 g of vitamin C, 100 mg of glucose, 96 mg of starch and 4 mg of magnesium stearate, 40 mg of ethanol was added to form granules, which were then dried at 60 ° C and tableted by a tablet machine.

[Formulation Example 9]

75 mg of Compound K, 75 mg of 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester acetic acid, 150 mg of vitamin C, 100 mg of glucose and 600 mg of starch were mixed and 100 mg of 30% And dried at 60 DEG C to form granules, which were filled in a capsule. The final weight of the contents was 1 g.

[Formulation Example 10]

0.0013 g of Compound K, 0.0013 g of 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester acetic acid, 0.0025 g of vitamin C, 10 g of glucose, 2 g of citric acid and 187.8 g of purified water, Respectively. The final volume of the contents was adjusted to 200 ml.

While the present invention has been particularly shown and described with reference to specific embodiments thereof, those skilled in the art will readily appreciate that many modifications are possible in the exemplary embodiments without materially departing from the novel teachings and advantages of this invention. something to do. Accordingly, the actual scope of the present invention will be defined by the appended claims and their equivalents.

Claims (8)

A compound K represented by the following formula 1; And 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester acetic acid represented by the following formula (2) as an active ingredient.
[Chemical Formula 1]

(2)

The composition for external application for skin according to claim 1, wherein the compound K is contained in an amount of 0.001 to 20% by weight based on the total weight of the composition. The skin external preparation according to claim 1, wherein the 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester acetic acid is contained in an amount of 0.001 to 20% Composition. The composition according to claim 1, wherein the compound K and 16-hydroxy-octadeca-9,17-diene-12,14-dienyl ester acetic acid are contained in a weight ratio of 1: 1 to 1: 4. Composition. The composition for external application for skin according to claim 1, wherein the composition is for enhancing skin barrier function. The composition for external application for skin according to claim 1, wherein the composition is for inducing differentiation of dermal keratinocytes. The composition for external application for skin according to claim 1, wherein the composition is for improving color and skin tone. The composition of claim 1, wherein the composition is a cosmetic composition.