Novel compounds and uses thereof

Abstract

The present invention relates to novel compounds having antioxidant and whitening activity, wherein the present invention is a compound represented by the following chemical formula 1, an isomer thereof, or a cosmetically acceptable salt. [Chemical Formula 1]

Description

Technology Field

[0001] The present invention relates to a novel compound having antioxidant and whitening activity and its uses. Background Technology

[0002] The rapid growth of the cosmetics market can actually be attributed to the rapid growth of the functional cosmetics market. Six years after the Functional Cosmetics Act of the Korea Food and Drug Administration came into effect and related products were approved, approximately 5,000 products have been approved, representing a tenfold increase compared to the 477 products approved in the first year. According to statistics by the Korea Cosmetic Association, functional cosmetics accounted for over 13% of the total cosmetics market as of 2004, serving as evidence that the domestic functional cosmetics market is expanding rapidly.

[0003] Meanwhile, interest in skin whitening is steadily increasing, influenced by the growing focus on health and beauty. As the preference for white skin rises due to skin damage caused by ultraviolet rays and people seek clearer, cleaner skin through transparent makeup, interest in methods to achieve skin whitening effects is intensifying.

[0004] Accordingly, the inventors of the present invention made diligent research efforts to discover a novel compound that ensures safety and exhibits enhanced whitening activity, and as a result, confirmed that a compound represented by Chemical Formula 1 not only has excellent whitening activity but also exhibits antioxidant activity, thereby completing the present invention. The problem to be solved

[0005] The problem that the present invention aims to solve is to provide a novel compound exhibiting excellent antioxidant and whitening activity, its isomer, or a cosmetically acceptable salt thereof.

[0006] Another objective of the present invention is to provide a novel compound exhibiting excellent antioxidant and whitening activity, its isomer, or a pharmaceutically acceptable salt thereof.

[0007] Another objective of the present invention is to provide a cosmetic composition comprising, as an active ingredient, a novel compound exhibiting excellent antioxidant and whitening activity, an isomer thereof, or a cosmetically acceptable salt thereof.

[0008] Another objective of the present invention is to provide a pharmaceutical composition comprising, as an active ingredient, a novel compound exhibiting excellent antioxidant and whitening activity, an isomer thereof, or a pharmaceutically acceptable salt thereof. means of solving the problem

[0009] One embodiment of the present invention is a compound represented by the following chemical formula 1, an isomer thereof, or a cosmetically acceptable salt.

[0010] [Chemical Formula 1]

[0011]

[0012] In the present invention, the compound may have antioxidant activity.

[0013] In the present invention, the compound may have whitening activity.

[0014] Another aspect of the present invention is a compound represented by the following chemical formula 1, an isomer thereof, or a pharmaceutically acceptable salt.

[0015] [Chemical Formula 1]

[0016]

[0017] In the present invention, the compound may have antioxidant activity.

[0018] In the present invention, the compound may have whitening activity.

[0019] Another aspect of the present invention is a cosmetic composition comprising, as an active ingredient, a compound represented by the following chemical formula 1, an isomer thereof, or a cosmetically acceptable salt thereof.

[0020] [Chemical Formula 1]

[0021]

[0022] In the present invention, the cosmetic composition may have antioxidant activity.

[0023] In the present invention, the cosmetic composition may have whitening activity.

[0024] Another aspect of the present invention is a quasi-drug composition comprising, as an active ingredient, a compound represented by the following chemical formula 1, an isomer thereof, or a pharmaceutically acceptable salt thereof.

[0025] [Chemical Formula 1]

[0026]

[0027] In the present invention, the quasi-drug composition may have antioxidant activity.

[0028] In the present invention, the quasi-drug composition may have whitening activity. Effects of the invention

[0029] The novel compound according to the present invention can exhibit excellent whitening and antioxidant activity. Brief explanation of the drawing

[0030] Figure 1 is a diagram showing the reaction scheme for the preparation of 3,4-dihydroxyphenethyl (E)-3-(3,4-dihydroxyphenyl)acrylate according to one embodiment of the present invention. Figure 2 is a diagram showing the antioxidant activity of a novel compound (ATO-002). Figure 3 is a graph evaluating the cell viability of the novel compound (ATO-002). Figure 4 is a graph evaluating the whitening activity of the novel compound (ATO-002). Specific details for implementing the invention

[0031] Hereinafter, embodiments of the present invention will be described in detail with reference to the attached drawings so that those skilled in the art can easily implement the present invention. However, the present invention may be embodied in various different forms and is not limited to the embodiments described herein.

[0033] In this specification, the term "containing as an active ingredient" means containing an amount sufficient to achieve the efficacy or activity of a novel compound. The quantitative upper limit of the compound included in the composition of the present invention may be selected and implemented within an appropriate range by a person skilled in the art.

[0034] The term "whitening" as used in the present invention encompasses methods for increasing the brightness of skin whose brightness has decreased due to an excess of pigments such as melanin, or for maintaining the brightness of the skin at a certain level, as well as skin with increased brightness formed by said method; specifically, it may refer to skin whitening. "Skin whitening" is understood as a result of inhibiting the production of melanin; specifically, it may be understood as the improvement of symptoms resulting from an increase in melanin, such as melasma, freckles, and skin aging, as a result of inhibiting melanin production.

[0035] Therefore, by including the compound of the present invention in cosmetics or quasi-drugs, a whitening effect can be achieved, thereby contributing to skin care and the like.

[0036] As used in this specification, the term "antioxidant" refers to the action of inhibiting oxidation. Although the human body maintains a balance between pro-oxidants and antioxidants, if this balance becomes unbalanced due to various factors and shifts toward oxidation promotion, oxidative stress is induced, leading to potential cell damage and pathological diseases. Reactive oxygen species, which are the direct cause of such oxidative stress, are unstable and highly reactive, easily reacting with various biomaterials and attacking macromolecules in the body to cause irreversible damage to cells and tissues, or to lead to mutations, cytotoxicity, and carcinogenesis. NO, HNO2, ONOO - Reactive nitrogen species (RNS), such as those mentioned above, are produced in large quantities due to the immune responses of macrophages, neutrophils, and other immune cells during inflammatory reactions, and ROS are also generated at this time. These reactive oxygen species oxidize and destroy cells in the body, leading to exposure to various diseases.

[0037] Therefore, by including the compound of the present invention in cosmetics or quasi-drugs, an antioxidant effect can be achieved, thereby contributing to health promotion.

[0039] One embodiment of the present invention is a compound represented by the following chemical formula 1, an isomer thereof, or a cosmetically acceptable salt.

[0040] [Chemical Formula 1]

[0041]

[0042] In addition, the novel compound according to Formula 1 of the present invention is as a starting material ( E )-3-(3,4-dihydroxyphenyl)acrylic acid(( E It can be manufactured through a step of reacting )-3-(3,4-dihydroxyphenyl)acrylic acid).

[0043] In the present invention, the compound represented by the above chemical formula 1 has a molecular weight of 317.12.

[0044] In the present invention, the compound may have whitening or antioxidant activity.

[0045] In the present invention, antioxidant activity was confirmed through a DPPH assay, and whitening activity was confirmed through a Melanin Contents Assay method that measures melanin production induced by α-MSH.

[0046] Another aspect of the present invention is a compound represented by the following chemical formula 1, an isomer thereof, or a pharmaceutically acceptable salt.

[0047] [Chemical Formula 1]

[0048]

[0049] In the present invention, the compound may have whitening or antioxidant activity.

[0050] In the present invention, antioxidant activity was confirmed through a DPPH assay, and whitening activity was confirmed through a Melanin Contents Assay method that measures melanin production induced by α-MSH.

[0051] Another aspect of the present invention is a cosmetic composition comprising, as an active ingredient, a compound represented by the following chemical formula 1, an isomer thereof, or a cosmetically acceptable salt thereof.

[0052] [Chemical Formula 1]

[0053]

[0054] In the cosmetic composition according to the present invention, the compound represented by Chemical Formula 1 is preferably 0.0001 to 20 weight% based on the total weight of the cosmetic composition.

[0055] In the present invention, the cosmetic composition may have whitening or antioxidant activity.

[0056] The cosmetic composition of the present invention may include, without limitation, commonly accepted ingredients in addition to the compound represented by Formula 1, and may include, for example, conventional auxiliary agents such as antioxidants, stabilizers, solubilizers, vitamins, pigments and fragrances, and carriers.

[0057] The cosmetic composition according to the present invention may be prepared in one or more formulations selected from the group consisting of solutions, topical ointments, creams, foams, nourishing lotions, softening lotions, packs, softening waters, emulsions, makeup bases, essences, soaps, liquid cleansers, bath additives, sunscreen creams, sun oils, suspensions, emulsions, pastes, gels, lotions, powders, soaps, surfactant-containing cleansing products, oils, powder foundations, emulsion foundations, wax foundations, patches, and sprays, but is not limited thereto.

[0058] In addition, the cosmetic composition of the present invention may further include one or more cosmetically acceptable carriers that are incorporated into general skin cosmetics, and may appropriately incorporate, for example, oils, water, surfactants, moisturizers, lower alcohols, thickeners, chelating agents, pigments, preservatives, fragrances, etc., as conventional ingredients, but are not limited thereto. The cosmetically acceptable carriers included in the cosmetic composition of the present invention vary depending on the formulation.

[0059] In the case where the formulation of the present invention is an ointment, paste, cream, or gel, animal oil, vegetable oil, wax, paraffin, starch, tracanth, cellulose derivative, polyethylene glycol, silicone, bentonite, silica, talc, zinc oxide, or a mixture thereof may be used as a carrier component.

[0060] In the case where the formulation of the present invention is a powder or a spray, lactose, talc, silica, aluminum hydroxide, calcium silicate, polyamide powder, or a mixture thereof may be used as a carrier component, and in particular, in the case of a spray, it may additionally include a propellant such as chlorofluorohydrocarbon, propane / butane, or dimethyl ether.

[0061] When the formulation of the present invention is a solution or an emulsion, a solvent, a solubilizing agent, or an emulsifying agent is used as a carrier component, such as water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1,3-butyl glycol oil, and in particular, cottonseed oil, peanut oil, corn germ oil, olive oil, castor oil and sesame oil, glycerol aliphatic ester, polyethylene glycol or fatty acid ester of sorbitan may be used.

[0062] In the case where the formulation of the present invention is a suspension, liquid diluents such as water, ethanol, or propylene glycol, ethoxylated isostearyl alcohol, polyoxyethylene sorbitol ester, and polyoxyethylene sorbitan ester, microcrystalline cellulose, aluminum metahydroxide, bentonite, agar, or tracant, etc. may be used as carrier components.

[0063] In the case where the formulation of the present invention is soap, alkali metal salts of fatty acids, fatty acid hemiester salts, fatty acid protein hydrolyzates, isethionates, lanolin derivatives, aliphatic alcohols, vegetable oils, glycerol, sugars, etc. may be used as carrier components.

[0064] In the case where the formulation of the present invention is a surfactant-containing cleansing agent, aliphatic alcohol sulfate, aliphatic alcohol ether sulfate, sulfosuccinic acid monoester, isethionate, imidazolinium derivative, methyl taurate, sarcocitate, fatty acid amide ether sulfate, alkylamidobetaine, aliphatic alcohol, fatty acid glyceride, fatty acid diethanolamide, vegetable oil, lanolin derivative, or ethoxylated glycerol fatty acid ester, etc. may be used as a carrier component.

[0065] Another aspect of the present invention is a quasi-drug composition comprising, as an active ingredient, a compound represented by the following chemical formula 1, an isomer thereof, or a pharmaceutically acceptable salt thereof.

[0066] [Chemical Formula 1]

[0067]

[0068] In the quasi-drug composition according to the present invention, the compound represented by Chemical Formula 1 is preferably 0.0001 to 20 weight% of the total weight of the quasi-drug composition.

[0069] In the present invention, the quasi-drug composition may have whitening or antioxidant activity.

[0070] The quasi-drug composition of the present invention may further include, in addition to the compound represented by Chemical Formula 1, a pharmaceutically acceptable salt as needed.

[0071] The quasi-drug composition of the present invention may further include, in addition to the above components, a pharmaceutically acceptable carrier, excipient, or diluent as needed. The pharmaceutically acceptable carrier, excipient, or diluent is not limited as long as it does not impair the effects of the present invention, and may include, for example, fillers, extenders, binders, wetting agents, disintegrants, surfactants, lubricants, sweeteners, fragrances, preservatives, etc.

[0072] Representative examples of pharmaceutically acceptable carriers, excipients, or diluents of the present invention include lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, maltitol, starch, gelatin, glycerin, acacia gum, alginate, calcium phosphate, calcium carbonate, calcium silicate, cellulose, methyl cellulose, microcrystalline cellulose, polyvinylpyrrolidone, water, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate, mineral oil, propylene glycol, polyethylene glycol, vegetable oil, injectable esters, Witepsol, macrogol, Tween 61, cocoa dough, laurize, etc.

[0073] Examples of the quasi-drug composition of the present invention include, but are not limited to, disinfectant cleansers, shower foams, ointment liquids, wet wipes, coating agents, etc., and the formulation method, dosage, method of use, components, etc. of the quasi-drug may be appropriately selected from ordinary techniques known in the technical field.

[0075] The present invention will be explained in more detail below through examples. However, the following examples are merely illustrative of the present invention, and the scope of the present invention is not limited to the following examples.

[0077] Preparation Example 1: (E)-3-(3,4- diacetoxyphenyl Preparation of acrylic acid

[0078] (E)-3-(3,4-dihydroxyphenyl)acrylic acid (3.0 g, 1.0 eq) and pyridine (1.97 ml, 1.5 eq) were placed in a reactor and cooled to 0–5°C at room temperature. Acetic anhydride (8.5 g, 5.0 eq) was slowly added over 10–20 minutes at the same temperature, followed by stirring at room temperature for more than 18 hours. Methylene chloride (10 ml) and n-Heptane (30 ml) was added and stirred at room temperature for more than 1 hour. The solid compound was filtered and then vacuum dried at 40°C for more than 12 hours to obtain a compound represented by the following chemical formula 2 (3.5 g, yield 79.7%).

[0079] [Chemical Formula 2]

[0080]

[0082] Preparation Example 2: (E)-4-(3-(3,4- dihydroxyphenethoxy )-3- oxoprop -1-en-1- yl )-1,2-phenylene diacetate manufacturing

[0083] (E)-3-(3,4-diacetoxyphenyl)acrylic acid (2.0 g, 1.0 eq) prepared in Preparation Example 1 above was placed in a reactor and cooled to 0–5°C under a nitrogen atmosphere. SOCl2 (1.3 g, 1.5 eq) was slowly added, and the mixture was stirred at room temperature for at least 1 hour. After concentrating the SOCl2 under reduced pressure, anhydrous methylene chloride (10 ml) was added under a nitrogen atmosphere (Reactor A). 4-(2-hydroxyethyl)benzene-1,2-diol (1.2 g, 1.05 eq), anhydrous methylene chloride (5 ml), and triethylamine (0.9 g, 1.2 eq) were added to Reactor B and stirred at room temperature for at least 30 minutes. After the materials from Reactor A were slowly added to Reactor B over 10–20 minutes at room temperature, the mixture was refluxed and stirred for at least 2 hours. After the reaction was completed, the reaction solution was concentrated under reduced pressure and separated by column chromatography using ethyl acetate / n-heptane as the developing solvent to obtain a compound according to Chemical Formula 3 below (1.9 g, yield 62.4%).

[0084] [Chemical Formula 3]

[0085]

[0087] Examples

[0088] Figure 1 is a diagram showing the reaction scheme for the preparation of 3,4-dihydroxyphenethyl (E)-3-(3,4-dihydroxyphenyl)acrylate.

[0089] (E)-4-(3-(3,4-dihydroxyphenethoxy)-3-oxoprop-1-en-1-yl)-1,2-phenylenediacetate (1.0 g, 1.0 eq) prepared in Preparation Example 2 above and 1,4-dioxane (10 ml) were placed in a reactor, 2N NaOH (3.7 ml, 3.0 eq) was added, and the mixture was stirred at 50°C for at least 3 hours. After the reaction was completed, the mixture was cooled to room temperature, 10% HCl (10 ml) and ethyl acetate (15 ml) were added, and the mixture was stirred for at least 30 minutes. The organic layer was extracted, dehydrated with MgSO4, and concentrated under reduced pressure. The compound according to Chemical Formula 1 below (0.54 g, yield 68.2%) was obtained by column chromatography separation using ethyl acetate / n-heptane as the developing solvent.

[0090] [Chemical Formula 1]

[0091]

[0092] 1 H-NMR (400 MHz, DMSO-d6) δ 7.46 (d, 1H), 7.06 (s, 1H), 6.81 (d, 1H), 6.65-6.50 (m, 4H), 6.29 (d, 1H), 4.48 (t, 2H), 2.96 (t, 2H)

[0093] MS (ESI+): m / z 317.12 [M+H] + .

[0095] Experimental Example 1: Antioxidant

[0096] The antioxidant activity of the novel compound (ATO-002) synthesized in the example was measured as follows.

[0097] Specifically, a 1 mM stock solution was prepared using ethanol under light-shielded conditions and then diluted 10-fold with ethanol to a final concentration of 100 μM. The sample was prepared using DMSO Hybri-Max to a concentration 100 times that of the final solution. As a positive control, 10 ppm ascorbic acid prepared using DMSO Hybri-Max as a solvent was used; a 1,000 ppm stock solution was prepared, diluted 100-fold with DPPH solution, and then treated.

[0098] The substance groups were divided into a total of six groups: a control, four compound concentrations (1 ppm, 10 ppm, 100 ppm, and 1000 ppm), and a positive control. 250 μL of 100 μM DPPH solution was dispensed into each well. Subsequently, 2.5 μL was withdrawn from each well, and 2.5 μL of the sample was added. For the samples, DMSO Hybri-Max was used for the control, a substance prepared at 100 times the final concentration was used for the substance groups, and 1,000 ppm ascorbic acid was used for the positive control. After treatment with the samples, the mixtures were reacted for 0, 15, 30, 60, and 180 minutes at room temperature under light-blocking aluminum foil, and the absorbance was measured at 517 nm. The results are shown in Figure 2. 250 μL of ethanol was used as the blank.

[0100] Referring to FIG. 2, it can be seen that the novel compound (ATO-002) according to the present invention exhibits antioxidant activity in a concentration-dependent manner.

[0102] Experimental Example 2: Cell viability experiment

[0103] The cell viability of the novel compound (ATO-002) synthesized in the example was measured as follows.

[0104] For MTT, a 5 mg / mL stock solution was prepared using clear media (basal media) free of FBS and antibiotics (Penicillin / Streptomycin) under light-shielded conditions, and this was diluted 25-fold to 0.2 mg / mL for use. To adjust the volume, 1 / 200 of the required amount of clear full media in DMSO was added to the Control and NC wells, while 1 / 200 of the required amount of the substance and 10,000 ppm of arbutin were added to the substance group and PC wells. Under light-shielded conditions, 250 μL of MTT solution was added to each well, and the samples were incubated for 2 hours and 10 minutes. After 2 hours and 10 minutes, to dissolve the generated formazan, each well was suctioned, 300 μL of DMSO was added, and the samples were shaken in a heating block at 25°C and 300 rpm for 30 minutes. Afterwards, 150 μL of the supernatant from each well was taken and transferred to a 96-well plate, and the absorbance was measured at 540 nm. 150 μL of DMSO was used as a blank, and the results are shown in Figure 3.

[0106] Referring to Figure 3, it can be seen that the new compound has a high cell viability at low concentrations of 2.5 ppm or less.

[0108] Experimental Example 3

[0109] The whitening activity of the novel compound (ATO-002) synthesized in the example was measured as follows.

[0110] Specifically, 2 × 10⁶ B16F10 melanoma cells in a 48-well plate 4The samples were added at the specified concentrations and treated for 24 hours in DMEM medium containing 10% FBS and 1% penicillin / streptomycin. There were a total of 6 sample groups: a control, a negative control, three sample concentrations (1 ppm, 2.5 ppm, 5 ppm), and a positive control. Only clear full media was used for the control, while for the NC, sample groups, and PC, 40 μM α-MSH was added to clear full media diluted 200-fold to 0.2 μM.

[0111] To adjust the volume, 1 / 200 of the required amount of clear full media (DMSO) was added to the control and NC, while 1 / 200 of the required amount of the substance and 10,000 ppm of arbutin were added to the substance group and PC. Cells were treated with 600 μL aliquots, as in seeding, and incubated for 48 hours. Afterward, the supernatant was removed, and the cells were washed twice with 1xPBS. Then, 200 μL of RIPA buffer (1% inhibitor cocktail) was added, and the mixture was incubated at 4°C for 30 minutes before the cells were collected into 1.5 ml e-tubes. The cells were centrifuged in a deep freezer centrifuge at 15,000 rpm at -8°C for 20 minutes to remove the supernatant, and the pellet was collected. Then, 500 µl of 1N NaOH was added and the pellet was dissolved at 70°C for 1 hour. Afterward, 100 µl of the dissolved pellet was placed in each well of a 96-well plate, and the absorbance was measured at 475 nm using a microplate reader. The results are shown in Figure 4.

[0113] Referring to Figure 4, it can be seen that the melanin content of the novel compound gradually decreases significantly with increasing treatment concentration at concentrations of 1 ppm, 2.5 ppm, and 5 ppm.

[0115] As such, a composition containing the novel compound according to the present invention can exhibit excellent antioxidant and whitening activity.

Claims

Claim 1 A cosmetic composition for skin whitening comprising a compound represented by the following chemical formula 1 as an active ingredient, wherein the compound represented by chemical formula 1 is 3,4-dihydroxyphenethyl (E)-3-(3,4-dihydroxyphenyl)acrylate, the compound represented by chemical formula 1 is included in an amount of 1 to 2.5 ppm based on the total weight of the cosmetic composition, and wherein, in the concentration range of 1 to 2.5 ppm, the compound represented by chemical formula 1 results in a higher cell viability of B16F10 melanoma cells than when treated with 5 ppm of the compound represented by chemical formula 1, inhibits α-MSH-induced melanin production, and exhibits antioxidant activity in a DPPH assay. [Chemical Formula 1] Claim 2 A quasi-drug composition for skin whitening comprising a compound represented by the following chemical formula 1 as an active ingredient, wherein the compound represented by chemical formula 1 is 3,4-dihydroxyphenethyl (E)-3-(3,4-dihydroxyphenyl)acrylate, the compound represented by chemical formula 1 is included in an amount of 1 to 2.5 ppm based on the total weight of the quasi-drug composition, and wherein, in the concentration range of 1 to 2.5 ppm, the compound represented by chemical formula 1 results in a higher cell viability of B16F10 melanoma cells than when treated with 5 ppm of the compound represented by chemical formula 1, inhibits α-MSH-induced melanin production, and exhibits antioxidant activity in a DPPH assay. [Chemical Formula 1] Claim 3 A method for preparing a compound represented by the following chemical formula 1, comprising the steps of: introducing (E)-3-(3,4-dihydroxyphenyl)acrylic acid and pyridine into a reactor, adding acetic anhydride for 10 to 20 minutes while cooled to 0 to 5°C, and reacting at room temperature for at least 18 hours to produce (E)-3-(3,4-diacetoxyphenyl)acrylic acid represented by the following chemical formula 2; reacting (E)-3-(3,4-diacetoxyphenyl)acrylic acid represented by the chemical formula 2 with SOCl₂ under a nitrogen atmosphere at 0 to 5°C, concentrating the SOCl₂ under reduced pressure, and adding anhydrous methylene chloride to prepare a reaction solution of reactor A; preparing a reaction solution of reactor B comprising 4-(2-hydroxyethyl)benzene-1,2-diol, anhydrous methylene chloride, and triethylamine, and adding 10 to the reaction solution of reactor A to the reaction solution of reactor B A step of preparing (E)-4-(3-(3,4-dihydroxyphenethoxy)-3-oxoprop-1-en-1-yl)-1,2-phenylene diacetate represented by the following chemical formula 3 by adding for 20 minutes and then refluxing and stirring for more than 2 hours; and a step comprising introducing (E)-4-(3-(3,4-dihydroxyphenethoxy)-3-oxoprop-1-en-1-yl)-1,2-phenylene diacetate represented by Chemical Formula 3 and 1,4-dioxane into a reactor, adding 2N NaOH and reacting at 50°C for at least 3 hours, then acid treating with 10% HCl, and separating by column chromatography using ethyl acetate / n-heptane as the developing solvent to prepare a compound represented by Chemical Formula 1 below; wherein the compound represented by Chemical Formula 1 is 3,4-dihydroxyphenethyl (E)-3-(3,4-dihydroxyphenyl)acrylate and has an MS(ESI+) value of m / z 317.A method for preparing a compound represented by Chemical Formula 1, wherein the compound represented by Chemical Formula 1 exhibits a [M+H]+ peak, and in a concentration range of 1 to 2.5 ppm, the cell viability of B16F10 melanoma cells is higher than when treated with 5 ppm of the compound represented by Chemical Formula 1, and α-MSH-induced melanin production is inhibited. [Chemical Formula 1]. [Chemical Formula 2] [Chemical Formula 3] Claim 4 delete Claim 5 delete Claim 6 delete Claim 7 delete Claim 8 delete Claim 9 delete Claim 10 delete Claim 11 delete Claim 12 delete

Images