cosmetics

Abstract

The present application relates to cosmetic compositions containing resveratron for improving skin health.

Description

[Technical field]

[0001] The present application relates to cosmetic compositions containing resveratron for improving skin health. [Background technology]

[0002] Resveratrone is a compound derived from the natural product resveratrol, and the compound structure and its manufacturing method have been patented (Korea Patent Publication No. 1294993, U.S. Patent Publication No. 10787607). In addition, the anti-cancer effects of resveratrone have been reported (Korea Patent Publication No. 2169585), but its effects on skin health are not yet known. Summary of the Invention [Problem to be solved by the invention]

[0003] The present application aims to provide a cosmetic composition containing resveratron for improving skin health.

[0004] However, the problems to be solved by the present application are not limited to those mentioned above, and other problems not mentioned will be clearly understood by those of ordinary skill in the art from the following description. [Means for solving the problem]

[0005] A first aspect of the present application provides a cosmetic composition comprising a compound represented by the following chemical formula 1 as an active ingredient: [ka] In the above Chemical Formula 1, R 1 is hydrogen; halogen; linear or branched C 1-6 Alkyl group; C 3-6 Cycloalkyl groups; linear or branched C 1-6 Alkoxy groups; C containing N, O, or S as heteroatoms 2-6Heterocycloalkyl group; or halogen atom, amino group, nitrile group, nitro group, C 1-10 Alkyl group, C 2-10 Alkenyl group, C 1-10 Alkoxy group, C 3-6 Cycloalkyl groups, C containing N, O, or S as heteroatoms 2-6 Heterocycloalkyl groups, C 6-16 C containing aryl groups and N, O, or S as heteroatoms 5-15 a phenyl group substituted or unsubstituted with one or more substituents selected from among heteroaryl groups; R 2 and R 3 each independently represents a hydroxy group, a linear or branched C 1-6 It is selected from among an alkoxy group and a benzoyl group.

[0006] A second aspect of the present application provides a single- or multi-functional cosmetic product comprising the cosmetic composition according to the first aspect. Effect of the Invention

[0007] The cosmetic composition containing the resveratron compound according to the embodiment of the present application has the characteristics of having a skin regeneration effect by inducing cell proliferation, an antioxidant effect by removing active oxygen, and a skin whitening effect by inhibiting melanin synthesis and tyrosinase activity.

[0008] The cosmetic composition containing the resveratron compound according to the embodiment of the present application has the characteristics of improving skin elasticity and wrinkles by promoting collagen synthesis, inhibiting the growth of acne-causing bacteria, thereby having antibacterial (anti-acne) effects on the skin, and blocking ultraviolet rays. [Brief description of the drawings]

[0009] [Figure 1] 1 is a graph showing the results of evaluating the cell proliferation activity of resveratron compounds in one example of the present application. [Diagram 2]1 is a graph showing the results of an antioxidant activity assay (DPPH assay) of resveratron compounds in one example of the present application. [Diagram 3] 1 is a graph showing the results of an evaluation of the skin-whitening efficacy of resveratron compounds (ability to inhibit melanin synthesis in B16F10 cells) in one example of the present application. [Figure 4] 1 is a graph showing the results of an evaluation of the skin-whitening efficacy of resveratron compounds (ability to inhibit extracellular melanin synthesis in B15F10 cells) in one example of the present application. [Diagram 5] 2 is a graph showing the results of an evaluation of the whitening efficacy (tyrosinase activity inhibitory ability) of resveratron compounds in one example of the present application. [Figure 6] 2 is a graph showing the results of evaluating the wrinkle improving efficacy (collagen synthesis ability) of a resveratron compound in one example of the present application. [Figure 7] 1 is a graph showing the results of evaluating the anti-acne efficacy (anti-Propionibacterium acnes antibacterial efficacy) of resveratron compounds in one example of the present application. [Figure 8] 1 is an absorbance spectrum of a resveratron compound in one embodiment of the present application. [Figure 9] 1 is a photograph showing the measurement of the UV protection index of a cream containing a resveratron compound in one embodiment of the present application. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0010] Hereinafter, the present invention will be described in detail with reference to the accompanying drawings so that those skilled in the art can easily carry out the present invention. However, the present invention may be embodied in various different forms and is not limited to the embodiments and examples described herein. In the drawings, in order to clearly explain the present invention, parts that are not related to the description are omitted, and similar parts are designated by similar reference numerals throughout the specification.

[0011] Throughout the specification of this application, when a part is said to be "connected" to another part, this includes not only "directly connected" but also "electrically connected" with another element therebetween.

[0012] Throughout this specification, when a member is said to be "on" another member, this includes not only when the member is in contact with the other member, but also when there is another member between the two members.

[0013] Throughout the specification of this application, when a part is said to "comprise" a certain element, this means that it may further include other elements, but not to the exclusion of other elements, unless specifically stated to the contrary.

[0014] As used herein, terms of degree such as "about," "substantially," and the like are used to mean a numerical value or close to a numerical value when the manufacturing and material tolerances inherent in the recited value are given, and are used to prevent unscrupulous infringers from unfairly taking advantage of the disclosure in which precise or absolute numerical values ​​are recited to aid in the understanding of the present application.

[0015] As used throughout the specification of this application, the terms "a step of" or "a step of" do not mean "a step for."

[0016] Throughout the specification of this application, the term "combination(s) thereof" contained in a Markush form expression means a mixture or combination of one or more selected from the group of elements set forth in the Markush form expression, and is meant to include one or more selected from the group of elements.

[0017] Throughout the specification of this application, the statement "A and / or B" means "A or B, or A and B."

[0018] Hereinafter, specific examples of the present application will be described in detail, but the present application is not limited thereto.

[0019] A first aspect of the present application provides a cosmetic composition comprising a compound represented by the following chemical formula 1 as an active ingredient: [ka] In the above Chemical Formula 1, R 1 is hydrogen; halogen; linear or branched C 1-6 Alkyl group; C 3-6 Cycloalkyl groups; linear or branched C 1-6 Alkoxy groups; C containing N, O, or S as heteroatoms 2-6 Heterocycloalkyl group; or halogen atom, amino group, nitrile group, nitro group, C 1-10 Alkyl group, C 2-10 Alkenyl group, C 1-10 Alkoxy group, C 3-6 Cycloalkyl groups, C containing N, O, or S as heteroatoms 2-6 Heterocycloalkyl groups, C 6-16 C containing aryl groups and N, O, or S as heteroatoms 5-15 a phenyl group substituted or unsubstituted with one or more substituents selected from among heteroaryl groups; R 2 and R 3 each independently represents a hydroxy group, a linear or branched C 1-6 It is selected from among an alkoxy group and a benzoyl group.

[0020] In an embodiment of the present application, the compound represented by Formula 1 may be represented by Formula 2 below. [ka] In the above Chemical Formula 2, R 1 is hydrogen; halogen; linear or branched C 1-6 Alkyl group; C 3-6 Cycloalkyl groups; linear or branched C 1-6 Alkoxy groups; C containing N, O, or S as heteroatoms 2-6Heterocycloalkyl group; or halogen atom, amino group, nitrile group, nitro group, C 1-10 Alkyl group, C 2-10 Alkenyl group, C 1-10 Alkoxy group, C 3-6 Cycloalkyl groups, C containing N, O, or S as heteroatoms 2-6 Heterocycloalkyl groups, C 6-16 C containing aryl groups and N, O, or S as heteroatoms 5-15 a phenyl group substituted or unsubstituted with one or more substituents selected from among heteroaryl groups; R 2 and R 3 each independently represents a hydroxy group, a linear or branched C 1-6 It is selected from among an alkoxy group and a benzoyl group.

[0021] In one embodiment of the present application, the compound represented by Formula 1 is [ka] It may be selected from, but is not limited to, the above.

[0022] In one embodiment of the present application, the compound represented by Chemical Formula 1 may be in the form of a cosmetically acceptable salt. In one embodiment of the present application, the salt may be an acid addition salt formed using an inorganic acid or an organic acid, the inorganic acid may include at least one selected from hydrochloric acid, phosphoric acid, bromic acid, nitric acid, carbonic acid, tartaric acid, boric acid, and carbonic acid, and the organic acid may include at least one selected from formic acid, acetic acid, lactic acid, butyric acid, citric acid, propionic acid, isobutyric acid, trifluoroacetic acid, malic acid, maleic acid, malonic acid, fumaric acid, succinic acid monoamide, glutamic acid, dichloroacetic acid, aminooxyacetic acid, tartaric acid, oxalic acid, citronic acid, glycolic acid, glucuronic acid, galacturonic acid, ascorbic acid, benzoic acid, phthalic acid, salicylic acid, anthranilic acid, benzenesulfonic acid, p-toluenesulfonic acid, and methanesulfonic acid, but is not limited thereto. In one embodiment of the present application, the acid addition salt may be prepared by a general salt preparation method in which the compound represented by Formula 1 and an acid are mixed directly or in the presence of a solvent.

[0023] A second aspect of the present application provides a single- or multi-functional cosmetic product comprising the cosmetic composition according to the first aspect.

[0024] In one embodiment of the present application, the multifunctionality may include one or more selected from skin regeneration, skin whitening, skin wrinkle improvement, anti-acne, UV protection, and anti-oxidation.

[0025] In one embodiment of the present application, the skin regeneration means that skin tissue damaged by inflammation and wounds is restored by regenerating skin cells, and the cosmetic for skin regeneration may have the effect of rapidly regenerating skin cells by promoting cell proliferation with the compound represented by Chemical Formula 1.

[0026] In one embodiment of the present application, the skin whitening refers to lightening the skin color and improving skin pigmentation such as age spots and freckles, and the skin whitening cosmetic may have the skin whitening effect by the compound represented by Chemical Formula 1 inhibiting the synthesis of melanin pigment in the skin and inhibiting the activity of melanin synthesis enzyme.

[0027] In one embodiment of the present application, the improvement of skin wrinkles means improving skin wrinkles or inhibiting the formation of wrinkles by increasing skin elasticity, and the cosmetic for improving skin wrinkles may have the effect of improving skin wrinkles by increasing the elasticity of the skin as the compound represented by Chemical Formula 1 helps synthesize collagen in the skin.

[0028] In one embodiment of the present application, the anti-acne (antibacterial) skin property means suppressing or inhibiting the growth of bacteria on the skin, and the antibacterial skin function may be that the compound represented by Chemical Formula 1 has the antibacterial skin effect by inhibiting the growth of bacteria that cause acne on the skin.

[0029] In one embodiment of the present application, the antioxidant effect may be achieved by the compound represented by Formula 1 scavenging active oxygen in the skin.

[0030] In one embodiment of the present application, the cosmetic may simultaneously have effects of skin regeneration, skin whitening, wrinkle improvement, antibacterial properties, skin antioxidant properties, and UV protection by including the cosmetic composition, and the degree of each functionality may vary depending on the content of the compound represented by Chemical Formula 1, and various products can be made by varying the content according to the purpose. In one embodiment of the present application, the cosmetic may be a cosmetic for skin regeneration, skin whitening, wrinkle improvement, antibacterial properties (anti-acne), skin antioxidant properties, and UV protection.

[0031] In one embodiment of the present application, the formulation of the cosmetic product may be selected from, but is not limited to, lotion, essence, milky lotion, cream, gel, powder, pack, soap or shampoo surfactant, rinse, oil, foundation, hair dye, and wax. In one embodiment of the present application, the cosmetic product may further include, but is not limited to, a cosmetically acceptable auxiliary selected from, but is not limited to, a surfactant, water, an emulsifier, a filler, a fragrance, a stabilizer, a dissolving agent, a gelling agent, a fatty substance, alcohol, and a thickener.

[0032] In one embodiment of the present application, the cosmetic formulation may be an external skin preparation selected from the group consisting of ointments, gels, creams, sprays, and patches, but is not limited thereto.

[0033] Hereinafter, the present application will be described in more detail with reference to examples. However, the following examples are merely illustrative to aid in understanding the present application, and the contents of the present application are not limited to the following examples. EXAMPLES

[0034] Example 1: Synthesis of resveratrone With reference to the prior art [Korean Patent Publication No. 1294993], resveratron represented by the following formula 3 was synthesized by the following method.

[0035] 1) Resveratrol was dissolved in methanol at a concentration of 0.1 g / L to 1.0 g / L. 2) UV-B lamp (λ max The resveratron solution was irradiated with UV light using a special UV reactor equipped with a UV ray (=306 nm). 3) After the reaction, the solution was concentrated and resveratron was separated using Prep-HPLC equipment.

[0036] [ka]

[0037] <Experimental Example 1: Evaluation of cell proliferation ability of resveratron> 1) Normal human fibroblasts were cultured. 2) Cells were seeded at an appropriate number and 24 hours later, starvation was carried out for 24 hours. 3) Cells were cultured for 72 hours in medium containing various concentrations of each sample. 4) Cell activity was measured and analyzed using the MTT method.

[0038] Referring to FIG. 1, the cell number in the test group treated with 10 μM resveratron increased by 20%, confirming the cell proliferation ability.

[0039] <Experimental Example 2: Evaluation of the antioxidant activity of resveratron (DPPH assay)> 1) 115 μL of 70% ethanol was dispensed into each of the 96 wells. 2) 5 μL of each sample and the positive control group was dispensed, and the absorbance was measured at 517 nm to determine the absorbance value before the reaction. 3) DPPH solution was dispensed in 80 μL portions. 4) The absorbance after the reaction was measured at 517 nm, and the results were analyzed using the absorbance values ​​before and after the reaction.

[0040] Referring to FIG. 2, radical scavenging ability was confirmed in the resveratron test group at concentrations of 1 μM to 50 μM.

[0041] <Experimental Example 3: Evaluation of the whitening effect of resveratron (inhibitory effect on melanin synthesis in B16F10 cells)> 1) B16F10 cells were cultured. 2) Appropriate numbers of cells were inoculated, and 24 hours later, all groups except the blank were treated with α-MSH or samples. 3) Cells were cultured in the culture medium containing each sample for 72 hours. 4) The cells were lysed, the supernatant was separated, and the absorbance value of the supernatant was measured. 5) The protein content of each supernatant was measured and analyzed using the BCA method. 6) The amount of melanin synthesis per unit cell was calculated by correcting the melanin synthesis value measured in the supernatant by the protein amount.

[0042] Referring to FIG. 3, inhibition of melanin synthesis was confirmed in the test groups treated with resveratron at concentrations of 10 μM to 50 μM (Arbutin: positive control group).

[0043] <Experimental Example 4: Evaluation of the whitening effect of resveratron (B15F10 extracellular melanin synthesis inhibitory effect)> 1) B16F10 cells were cultured. 2) Appropriate numbers of cells were inoculated, and 24 hours later, all groups except the blank were treated with α-MSH or samples. 3) Cells were cultured in the culture medium containing each sample for 72 hours. 4) The absorbance value of the cell culture medium was measured. 5) The cells were lysed, and the supernatant was separated. The protein content was measured by the BCA method and corrected for the amount of melanin synthesis. 6) The amount of melanin synthesis per unit cell was calculated by correcting the measured melanin synthesis value by the protein amount.

[0044] Referring to FIG. 4, inhibition of melanin synthesis was confirmed in the test groups treated with resveratron at concentrations of 10 μM to 50 μM (Arbutin: positive control group).

[0045] <Experimental Example 5: Evaluation of the whitening effect of resveratron (tyrosinase activity inhibitory activity)> 1) An appropriate amount of normal human pigment cells was inoculated and cultured for one day. 2) The culture medium was replaced with the treated medium for each sample and cultured for 72 hours. 3) The cells were lysed and the supernatant was separated. The supernatant was reacted with the reaction substrate, dopa, at 37° C. while measuring the absorbance at 475 nm at 30-minute intervals. 4) The protein content of the cell lysate supernatant was measured using the BCA method, and the tyrosinase (melanin synthesis enzyme) measurement value was corrected based on this.

[0046] Referring to FIG. 5, inhibition of tyrosinase activity was confirmed in the test groups treated with resveratron at concentrations of 1 μM to 50 μM.

[0047] <Experimental Example 6: Evaluation of the wrinkle improvement efficacy of resveratron (collagen synthesis ability)> 1) 2 x 10 normal human fibroblasts 5 The cells were inoculated in 6 wells and cultured. 2) The cells were cultured under starvation conditions for one day. 3) The samples were treated with the substances at different concentrations and then cultured for 24 hours. 4) The cells were washed with water, irradiated with UV light, and then cultured for 48 hours. 5) The expression level of collagen in cell culture medium was measured and analyzed.

[0048] Referring to FIG. 6, an increase in collagen synthesis was confirmed in the test groups treated with resveratron at concentrations of 10 μM to 20 μM.

[0049] <Experimental Example 7: Evaluation of the anti-acne efficacy of resveratron (antibacterial efficacy against propionibacterium acnes)> 1) The anaerobic acne bacterium Propionibacterium acnes strain was cultured under anaerobic culture conditions. 2) The turbidity of the strain was adjusted to McFarland standard No. 1, and then diluted 1 / 20 in liquid culture medium. 3) The samples were treated at different concentrations in liquid nutrient medium. 4) The liquid nutrient medium in which the samples had been treated was dispensed in 100 μL portions, and then 10 μL of each of the prepared strains was inoculated. 5) After culturing the strains under anaerobic culture conditions for 72 hours, the bacterial counts were measured and analyzed.

[0050] Referring to FIG. 7, inhibition of bacterial growth was confirmed in the test groups treated with resveratron at concentrations of 20 μM to 200 μM.

[0051] <Experimental Example 8: Resveratron absorbance measurement> 1) Resveratron was dissolved in an organic solvent at a concentration of 10 μM to 50 μM. 2) The absorbance of resveratron was measured using a spectrophotometer.

[0052] Referring to FIG. 8, absorption was confirmed in the entire ultraviolet region, including UV-A (320 to 400 nm), UV-B (280 to 320 nm), and UV-C (200 to 280 nm).

[0053] <Experimental Example 9: Measurement of UV protection index of resveratron-containing cream> 1) A resveratron-containing cream was produced by mixing purified water (65%), glycerol (7%), olive emulsifying wax (5%), jojoba oil (20%), and resveratron (3%) while heating to above 75°C. 2) Apply the cream to the back at 2.0 mg / cm 2 After applying the formula evenly, the sun protection factor (SPF, UV-B protection effect index) and the protection factor of UVA (PFA, UV-A protection effect index) were measured according to the measurement method announced by the Ministry of Food and Drug Safety.

[0054] Referring to FIG. 9, the results of clinical trials showed that the predicted SPF index was 4.0 and the predicted PFA index was 4.8, confirming the UV blocking effect.

[0055] The above description of the present application is for illustrative purposes only, and a person having ordinary skill in the art to which the present application pertains should understand that the present application can be easily modified into other specific forms without changing the technical idea or essential features of the present application. Therefore, it should be understood that the above-described embodiments are illustrative in all respects and are not limiting. For example, each component described as a single type may be implemented in a distributed form, and similarly, each component described as a distributed type may be implemented in a combined form.

[0056] The scope of the present application is indicated by the claims set forth below rather than by the above detailed description, and all modifications and variations derived from the meaning and scope of the claims, as well as their equivalent concepts, should be construed as being included within the scope of the present application.

Claims

1. A cosmetic product comprising a cosmetic composition, The cosmetic composition contains a compound represented by the following formula 1 as an active ingredient: The cosmetic is a cosmetic for skin regeneration, a cosmetic for skin whitening, a cosmetic for improving skin wrinkles, an anti-acne cosmetic, or an antioxidant cosmetic. 【Chemistry 1】 In the above Chemical Formula 1, R １ is hydrogen or a linear or branched C １－６ is an alkoxy group, R ２ and R ３ each independently represents a hydroxy group or a linear or branched C １－６ It is an alkoxy group.

2. The compound represented by the formula 1 is 【Chemistry 2】 The cosmetic product according to claim 1, selected from the group consisting of

3. The cosmetic product according to claim 1 , wherein the cosmetic product has a formulation selected from the group consisting of lotion, essence, milky lotion, cream, gel, powder, pack, soap, shampoo, rinse, oil, foundation, hair dye, and wax.

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