KR20230145741A - New composition for soothing sensitive skin - Google Patents

Abstract

The present invention provides an antioxidant and anti-inflammatory composition containing as an active ingredient at least one derivative of a compound represented by the following general formula (I).
(I)
In the above formula, R _1, R _2, R ₃ are C1 to C3 saturated or unsaturated straight-chain or branched alkyl groups, R ₄ is selected from R ₅ , saturated or unsaturated straight-chain or branched alkoxy, and R ₅ Is or structure, and R ₆ is hydrogen, C1 to C5 saturated or unsaturated straight-chain or branched alkyl.

Description

Composition for soothing sensitive skin {New composition for soothing sensitive skin}

The present invention relates to an anti-inflammatory and/or antioxidant composition, and more specifically, an external skin preparation, specifically a cosmetic or pharmaceutical composition, which is safe for the human body with few side effects and has excellent anti-inflammatory and antioxidant effects.

Active oxygen introduced from outside the body or generated within the body causes many problems, such as accelerating aging of the body or causing cancer. Therefore, development and research on antioxidant substances that inhibit oxidation by active oxygen are being actively conducted. Antioxidants are widely distributed in nature, and fruits and vegetables contain many phenolic compounds, flavonoids, tocopherols, vitamin C, and selenium. However, antioxidant substances that exist in nature cannot be expected to have a substantially sufficient effect when applied to the skin. Therefore, synthetic antioxidants that have excellent antioxidant power and are inexpensive are widely used, but their use is limited due to safety concerns such as side effects on the human body.

In addition, inflammation is the body's immune response to wounds or diseases, and oxidative stress such as ultraviolet rays or active oxygen activates inflammatory factors, causing various diseases and aging. Anti-inflammatory drugs are called anti-inflammatory drugs that act to remove inflammation sources and reduce biological reactions and symptoms. Non-steroidal anti-inflammatory drugs include ibuprofen and indomethacin, while steroid anti-inflammatory drugs include prednisolone, Examples include dexamethasone. The amount of use of these substances is limited due to safety issues on the skin, or their effectiveness is minimal, so there is a problem in that they cannot be expected to relieve inflammation in the human body.

Therefore, there is an urgent need for the development of materials that are safe for the living body, stable over time, and, above all, have superior antioxidant and anti-inflammatory effects than existing materials.

The object of the present invention is to provide a composition for external skin application that has no side effects on the skin and has excellent antioxidant and anti-inflammatory effects.

The above objective is achieved by a compound having the chemical structure of general formula (I) as shown below or a pharmacologically acceptable salt thereof.

(I)

In the above formula, R _1, R _2, R ₃ are C1 to C3 saturated or unsaturated straight-chain or branched alkyl groups, R ₄ is selected from R ₅ , saturated or unsaturated straight-chain or branched alkoxy, and R ₅ Is or structure, and R ₆ is hydrogen, C1 to C5 saturated or unsaturated straight-chain or branched alkyl.

The compound according to the present invention not only has no side effects on the skin, but also exhibits antioxidant and anti-inflammatory effects, so a composition containing it can be used as a composition for antioxidant and anti-inflammatory purposes.

The present invention provides a compound having the chemical structure of general formula (I), which has excellent antioxidant and anti-inflammatory effects:

(I)

In the above formula, R _1, R _2, R ₃ are C1 to C3 saturated or unsaturated straight-chain or branched alkyl groups, R ₄ is selected from R ₅ , saturated or unsaturated straight-chain or branched alkoxy, and R ₅ Is or structure, and R ₆ is hydrogen, C1 to C5 saturated or unsaturated straight-chain or branched alkyl.

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

The compound of the present invention is prepared by dissolving an aromatic compound in an appropriate organic solvent as shown in the following reaction formula, then mixing one or two or more alkyl halides and slowly adding them dropwise at an appropriate equivalent ratio to produce an ester reaction or an ether reaction. It can be obtained through or by performing hydrogenation on this reactant again. At this time, the organic solvent usable for the reaction is not particularly limited, and examples include dichloromethane, chloroform, tetrahydrofuran, acetonitrile, dimethylformamide, dimethylsuloxide, pyridine, dimethylformamide, etc. In particular, sodium hydride (NaH) or potassium carbonate (K ₂ CO ₃ ) can be used as a reaction catalyst.

[Scheme 1]

In Scheme 1, R _1, R _{2, and} R ₃ are C1 to C3 saturated or unsaturated straight or branched alkyl groups, and R ₇ is C1 to _C3 saturated or unsaturated alkyl, which can be either straight or branched. do.

[Scheme 2]

In Scheme 2, R _{1 ,} R _{2 , and} R ₃ are C1 to C3 saturated or unsaturated straight-chain or branched alkyl groups, and R ₇ is _C1-5 saturated or unsaturated alkyl, which can be either straight-chain or branched. do.

As a more specific example of the compound of general formula (I) according to the present invention, when R _{1 ,} R _{2 , and} R ₃ are methyl, the names of the substances produced are as follows.

For example, methyl 3,4,5-trimethoxycinnamate, ethyl 3,4,5-trimethoxycinnamate, propyl 3,4,5-trimethoxycinnamate, butyl 3,4,5-trimethoxycinnamate. Trimethoxycinnamate, pentyl 3,4,5-trimethoxycinnamate, etc., but is not limited thereto.

In addition, among the substances produced through Scheme 2, the names of substances produced when R _{1 ,} R _{2 , and} R ₃ are methyl are exemplified as follows.

For example, methyl 3,4,5-trimethoxybenzoate, ethyl 3,4,5-trimethoxybenzoate, propyl 3,4,5-trimethoxybenzoate, butyl 3,4,5- Trimethoxybenzoate, pentyl, etc., but are not limited thereto.

The present invention also provides an antioxidant and anti-inflammatory skin external composition comprising the compound of the general formula (I) as an active ingredient.

A composition containing the compound of the present invention may further include an appropriate carrier, excipient, or diluent according to conventional methods.

Carriers, excipients and diluents that may be included in the composition of the present invention include lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starch, gum acacia, alginate, gelatin, calcium phosphate, calcium silicate, Cellulose, methyl cellulose, microcrystalline cellulose, polyvinyl pyrrolidone, water, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate and mineral oil.

The composition containing the compound of the present invention is formulated in the form of oral dosage forms such as powders, granules, tablets, capsules, suspensions, emulsions, syrups, aerosols, external preparations, suppositories, or sterile injection solutions, respectively, according to conventional methods. It can be used.

In detail, when formulating, it can be prepared using diluents or excipients such as commonly used fillers, extenders, binders, wetting agents, disintegrants, and surfactants. Solid preparations for oral administration include tablets, pills, powders, granules, capsules, etc., and these solid preparations contain at least one excipient, such as starch, calcium carbonate, or sucrose, in the extract. ), lactose, gelatin, etc. can be mixed. Additionally, in addition to simple excipients, lubricants such as magnesium stearate and talc can also be used. Liquid preparations for oral use include suspensions, oral solutions, emulsions, and syrups. In addition to the commonly used simple diluents such as water and liquid paraffin, they contain various excipients such as wetting agents, sweeteners, fragrances, and preservatives. You can. Preparations for parenteral administration include sterile aqueous solutions, non-aqueous solutions, suspensions, emulsions, lyophilized preparations, and suppositories. Non-aqueous solvents and suspensions include propylene glycol, polyethylene glycol, vegetable oil such as olive oil, and injectable ester such as ethyl oleate. As a base for suppositories, witepsol, macrogol, tween 61, cacao, laurel, glycerogelatin, etc. can be used.

The antioxidant and anti-inflammatory composition containing the compound of general formula (I) of the present invention as an active ingredient is a skin external preparation that can be applied to the skin and is used in the form of creams, gels, patches, sprays, ointments, warning agents, lotions, and linies. It can be prepared and used as a pharmaceutical composition in the form of an external skin preparation such as ment, pasta, or cataplasma, but is not limited to this.

The preferred dosage of the compound of formula (I) of the present invention or a pharmacologically acceptable salt thereof varies depending on the patient's condition and weight, degree of disease, drug form, administration route and period, but may be appropriately selected by a person skilled in the art. You can. However, for desirable effects, the compound of the present invention is preferably administered at 0.0001 to 100 mg/kg per day, preferably at 0.001 to 10 mg/kg. Administration may be administered once a day, or may be administered several times. The above dosage does not limit the scope of the present invention in any way.

In the pharmaceutical composition for external use on the skin, the mixing amount of the compounds according to the present invention is preferably 0.0001 to 20% by weight, more preferably 0.001 to 10% by weight, based on the total weight of the composition. If it is less than 0.001% by weight, the whitening effect is reduced. This is because it is difficult to expect an increase in effectiveness even if mixed in amounts exceeding 20% by weight.

In addition, the pharmaceutical dosage form of the compounds of the present invention can be used in the form of their pharmaceutically acceptable salts, and can be used alone or in combination with other pharmaceutically active compounds, as well as in appropriate combinations.

The present invention provides a composition for external skin application for antioxidant and anti-inflammatory purposes, comprising the compound of the general formula (I) as an active ingredient.

The composition containing the compound of general formula (I) of the present invention as an active ingredient can be used in various ways such as cosmetics and facial cleansers for antioxidant and anti-inflammatory effects. Products to which this composition can be added include, for example, cosmetics such as various creams, lotions, skins, etc., cleansing products, face washes, soaps, treatments, and beauty essences.

The cosmetic of the present invention includes a composition selected from the group consisting of water-soluble vitamins, oil-soluble vitamins, high molecular weight peptides, high molecular weight polysaccharides, sphingolipids, and seaweed extract.

Water-soluble vitamins may be any that can be mixed into cosmetics, but preferably include vitamin B1, vitamin B2, vitamin B6, pyridoxine, pyridoxine hydrochloride, vitamin B12, pantothenic acid, nicotinic acid, nicotinic acid amide, folic acid, vitamin C, and vitamin H. and their salts (thiamine hydrochloride, sodium ascorbate, etc.) or derivatives (sodium ascorbic acid-2-phosphate, magnesium ascorbic acid-2-phosphate, etc.) are also water-soluble vitamins that can be used in the present invention. Included. Water-soluble vitamins can be obtained by conventional methods such as microbial transformation, purification from microbial cultures, enzymatic methods, or chemical synthesis.

Oil-soluble vitamins may be any that can be mixed into cosmetics, but preferably include vitamin A, carotene, vitamin D2, vitamin D3, vitamin E (d1-alpha tocopherol, d-alpha tocopherol, d-alpha tocopherol), etc. , their derivatives (ascorbic palmitate, ascorbic stearate, ascorbic acid dipalmitate, dl-alpha tocopherol acetate, dl-alpha tocopherol nicotinic acid, vitamin E, DL-pantothenyl alcohol, D-pantothenyl alcohol, pantothenyl ethyl ether, etc.) are also included in the oil-soluble vitamins used in the present invention. Oil-soluble vitamins can be obtained by conventional methods such as microbial transformation, purification from microbial cultures, enzymatic or chemical synthesis.

The polymer peptide may be any peptide that can be blended into cosmetics, but preferably includes collagen, hydrolyzed collagen, gelatin, elastin, hydrolyzed elastin, and keratin. High molecular weight peptides can be purified and obtained by conventional methods such as purification from microbial culture media, enzymatic methods, or chemical synthesis, or they can usually be purified and used from natural products such as dermis of pigs or cows or silk fiber of silkworms.

The high molecular polysaccharide may be any one that can be blended into cosmetics, but preferably includes hydroxyethyl cellulose, xanthan gum, sodium hyaluronate, chondroitin sulfate or its salts (sodium salt, etc.). For example, chondroitin sulfate or its salt can usually be purified and used from mammals or fish.

The sphingolipid may be any one that can be incorporated into cosmetics, but preferably includes ceramide, phytosphingosine, and sphingolipid. Sphingolipids can usually be purified by conventional methods from mammals, fish, shellfish, yeast, or plants, or obtained by chemical synthesis.

The seaweed extract can be anything that can be mixed into cosmetics, but preferably includes brown algae extract, red algae extract, green algae extract, etc., and calrageenan, arginic acid, sodium alginate, etc. purified from these seaweed extracts. Potassium arginate and the like are also included in the seaweed extract used in the present invention. Seaweed extract can be obtained by purifying seaweed by a conventional method.

In addition to the above-mentioned essential ingredients, the cosmetic of the present invention may contain other ingredients usually blended in cosmetics as needed.

Other ingredients that may be added include oils and fats, moisturizers, emollients, surfactants, organic and inorganic pigments, organic powders, ultraviolet absorbers, preservatives, disinfectants, antioxidants, plant extracts, pH adjusters, alcohol, colorants, fragrances, Examples include blood circulation promoters, cooling agents, antiperspirants, and purified water.

Examples of oil and fat components include ester-based fats and oils, hydrocarbon-based fats and oils, silicone-based fats and oils, fluorine-based fats and oils, animal fats and oils, and vegetable fats and oils.

Ester oils include glyceryl tri2-ethylhexanoate, cetyl 2-ethylhexanoate, isopropyl myristate, butyl myristate, isopropyl palmitate, ethyl stearate, octyl palmitate, isocetyl isostearate, and stearic acid. Butyl, ethyl linoleate, isopropyl linoleate, ethyl oleate, isocetyl myristate, isostearyl myristate, isostearyl palmitate, octyldodecyl myristate, isocetyl isostearate, diethyl sebacate, adipine. Diisopropyl acid, isoalkyl neopentanoate, tri(caprylic, capric acid)glyceryl, trimethylolpropane tri2-ethylhexanoate, trimethylolpropane triisostearate, pentaelislitol tetra2-ethylhexanoate , cetyl caprylate, decyl laurate, hexyl laurate, decyl myristate, myristyl myristate, cetyl myristate, stearyl stearate, decyl oleate, cetyl ricinooleate, isostear laurate. Reyl, isotridecyl myristate, isocetyl palmitate, octyl stearate, isocetyl stearate, isodecyl oleate, octyldodecyl oleate, octyldodecyl linoleate, isopropyl isostearate, cetoester 2-ethylhexanoate Aryl, 2-ethylhexanoate stearyl, hexyl isostearate, ethylene glycol dioctanate, ethylene glycol dioleate, propylene glycol dicapric acid, di(capryl, capric acid) propylene glycol, propylene glycol dicaprylate, dicapric acid Neopentyl glycol prinate, neopentyl glycol dioctanate, glyceryl tricaprylate, glyceryl triundecylate, glyceryl triisopalmitate, glyceryl triisostearate, octyldodecyl neopentanoate, isostearyl octanoate. , octyl isononanoate, hexyldecyl neodecanoate, octyldodecyl neodecanoate, isocetyl isostearate, isostearyl isostearate, octyldecyl isostearate, polyglycerol oleic acid ester, polyglycerol isostearic acid ester, Triisocetyl citrate, triisoalkyl citrate, triisooctyl citrate, lauryl lactate, myristyl lactate, cetyl lactate, octyldecyl lactate, triethyl citrate, acetyltriethyl citrate, acetyltributyl citrate, trioctyl citrate, dimalate Isostearyl, 2-ethylhexyl hydroxystearate, di2-ethylhexyl succinate, diisobutyl adipate, diisopropyl sebacate, dioctyl sebacate, cholesteryl stearate, cholesteryl isostearate, Cholesteryl hydroxystearate, cholesteryl oleate, dihydrocholesteryl oleate, phytsteryl isostearate, phytsteryl oleate, 12-stealoyl hydroxystearate isocetyl, 12-stealoyl hydride. Ester systems such as stearyl hydroxystearate and isostearyl 12-stealoylhydroxystearate can be mentioned.

Hydrocarbon-based fats and oils include squalene, liquid paraffin, alpha-olefin oligomer, isoparaffin, ceresin, paraffin, liquid isoparaffin, polybudene, microcrystalline wax, and petroleum jelly.

Silicone oils include polymethyl silicone, methylphenyl silicone, methylcyclopolysiloxane, octamethylpolysiloxane, decamethylpolysiloxane, dodecamethylcyclosiloxane, dimethylsiloxane/methylcetyloxysiloxane copolymer, dimethylsiloxane/methylstealoxysiloxane copolymer, and alkyl. Modified silicone oil, amino-modified silicone oil, etc. can be mentioned.

Examples of fluorine-based fats and oils include perfluoropolyether.

Animal or plant oils include avocado oil, almond oil, olive oil, sesame oil, rice bran oil, birdflower oil, soybean oil, corn oil, rapeseed oil, apricot oil, palm kernel oil, palm oil, castor oil, sunflower oil, and grape seed oil. , cottonseed oil, palm oil, cucumber nut oil, wheat germ oil, rice germ oil, shea butter, walnut colostrum oil, marker damia nut oil, meadow oil, egg yolk oil, beef tallow, horse oil, mink oil, orange rape oil, jojoba oil. , animal or plant oils such as candelier wax, carnaba wax, liquid lanolin, and hydrogenated castor oil.

Moisturizers include water-soluble low-molecular-weight moisturizers, oil-soluble molecular moisturizers, water-soluble polymers, and fat-soluble polymers.

Water-soluble low-molecular-weight moisturizers include serine, glutamine, sorbitol, mannitol, sodium pyrrolidone-carboxylate, glycerin, propylene glycol, 1,3-butylene glycol, ethylene glycol, polyethylene glycol B (degree of polymerization n = 2 or more), and polypropylene. Examples include glycol (degree of polymerization n = 2 or more), polyglycerin B (degree of polymerization n = 2 or more), lactic acid, lactate, etc.

Examples of fat-soluble low-molecular-weight moisturizers include cholesterol and cholesterol esters.

Water-soluble polymers include carboxyvinyl polymer, polyaspartate, tragacanth, xanthan gum, methyl cellulose, hydroxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, carboxymethyl cellulose, water-soluble chitin, chitosan, and dextrin. You can.

Examples of oil-soluble polymers include polyvinylpyrrolidone/eicosene copolymer, polyvinylpyrrolidone/hexadecene copolymer, nitrocellulose, dextrin fatty acid ester, and polymer silicone.

Examples of emollients include long-chain acyl glutamic acid cholesteryl ester, hydroxystearic acid cholesteryl, 12-hydroxystearic acid, stearic acid, rosin acid, and lanolin fatty acid cholesteryl ester.

Examples of surfactants include nonionic surfactants, anionic surfactants, cationic surfactants, and amphoteric surfactants.

Nonionic surfactants include self-emulsifying glycerin monostearate, propylene glycol fatty acid ester, glycerin fatty acid ester, polyglycerin fatty acid ester, sorbitan fatty acid ester, POE (polyoxyethylene) sorbitan fatty acid ester, POE sorbitan fatty acid ester, POE. Glycerin fatty acid ester, POE alkyl ether, POE fatty acid ester, POE hydrogenated castor oil, POE castor oil, POEㆍPOP (polyoxyethyleneㆍpolyoxypropylene) copolymer, POEㆍPOP alkyl ether, polyether modified silicone, lauric acid Examples include alkanolamide, alkylamine oxide, and hydrogenated soybean phospholipid.

Anionic surfactants include fatty acid soap, alpha-acyl sulfonate, alkyl sulfonate, alkyl allyl sulfonate, alkyl naphthalene sulfonate, alkyl sulfate, POE alkyl ether sulfate, alkyl amide sulfate, alkyl phosphate, POE alkyl phosphate, and alkyl amide phosphate. , alkyloyl alkyl taurine salt, N-acylamino acid salt, POE alkyl ether carboxylate, alkyl sulfosuccinate, sodium alkyl sulfoacetate, acylated hydrolyzed collagen peptide salt, perfluoroalkyl phosphate ester, etc. .

Cationic surfactants include alkyltrimethylammonium chloride, stearyltrimethylammonium chloride, stearyltrimethylammonium bromide, cetostearyltrimethylammonium chloride, distearyldimethylammonium chloride, stearyldimethylbenzylammonium chloride, behenyltrimethylammonium bromide, and cationic surfactant. Benzalkonium, diethylaminoethylamide stearate, dimethylaminopropylamide stearate, quaternary ammonium salt of lanolin derivative, etc. are mentioned.

Amphoteric surfactants include carboxy beta type, amide beta type, sulfo beta type, hydroxy sulfo beta type, amide sulfo beta type, phosphobeta type, aminocarboxylate type, imidazoline derivative type, and amide amine type. Amphoteric surfactants, etc. can be mentioned.

Organic and inorganic pigments include silicic acid, anhydrous silicic acid, magnesium silicate, talc, sericite, mica, kaolin, bengala, clay, bentonite, titanium-coated mica, bismuth oxychloride, zirconium oxide, magnesium oxide, zinc oxide, titanium oxide, and aluminum oxide. Inorganic pigments such as calcium sulfate, barium sulfate, magnesium sulfate, calcium carbonate, magnesium carbonate, iron oxide, ultramarine blue, chromium oxide, chromium hydroxide, calamine and complexes thereof; Polyamide, polyester, polypropylene, polystyrene, polyurethane, vinyl resin, urea resin, phenol resin, fluorine resin, silicon resin, acrylic resin, melamine resin, epoxy resin, polycarbonate resin, divinylbenzene/styrene copolymer, Examples include organic pigments such as silk powder, cellulose, CI pigment yellow, and CI pigment orange, and complex pigments of these inorganic pigments and organic pigments.

Examples of organic powder include metal soap such as calcium stearate; Alkyl phosphate metal salts such as sodium zinc cetilate, zinc laurylate, and calcium laurylate; Acyl amino acid polyvalent metal salts such as N-lauroyl-beta-alanine calcium, N-lauroyl-beta-alanine zinc, and N-lauroyl glycine calcium; Amidesulfonic acid polyvalent metal salts such as N-lauroyl-taurine calcium and N-palmitoyl-taurine calcium; N such as N-epsilon-lauroyl-L-lysine, N-epsilon-palmitoylizine, N-alpha-paritoylolnithine, N-alpha-lauroylarginine, N-alpha-hydrogenated beef tallow fatty acid acylarginine, etc. -Acyl basic amino acid; N-acyl polypeptides such as N-lauroylglycylglycine; Alpha-amino fatty acids such as alpha-aminocaprylic acid and alpha-aminolauric acid; Examples include polyethylene, polypropylene, nylon, polymethyl methacrylate, polystyrene, divinylbenzene/styrene copolymer, and ethylene tetrafluoride.

UV absorbers include para-aminobenzoic acid, ethyl para-aminobenzoate, amyl para-aminobenzoate, octyl para-aminobenzoate, ethylene glycol salicylate, phenyl salicylate, octyl salicylate, benzyl salicylate, butylphenyl salicylate, homomenthyl salicylate, and benzyl cinnamate. , paramethoxycinnamic acid-2-ethoxyethyl, paramethoxycinnamic acid octyl, diparamethoxycinnamic acid mono-2-ethylhexane glyceryl, paramethoxycinnamic acid isopropyl, diisopropylㆍdiisopropylcinnamic acid ester mixture, uro Kaninic acid, ethyl urocanate, hydroxymethoxybenzophenone, hydroxymethoxybenzophenone sulfonic acid and its salts, dihydroxymethoxybenzophenone, dihydroxymethoxybenzophenone disulfonate sodium, dihydroxybenzophenone , tetrahydroxybenzophenone, 4- tert -butyl-4'-methoxydibenzoylmethane, 2,4,6-trianilino- p -(carbo-2'-ethylhexyl-1'-oxy)-1 , 3,5-triazine, 2-(2-hydroxy-5-methylphenyl)benzotriazole, etc.

Disinfectants include hinokitiol, triclosan, trichlorohydroxydiphenyl ether, chlorhexidine gluconate, phenoxyethanol, resorcin, isopropylmethylphenol, azulene, salicylic acid, zincphyllithione, benzalkonium chloride, and photosensitive. Sub-No. 301, mononitroguaiacol sodium, undecirenic acid, etc. can be mentioned.

Antioxidants include butylhydroxyanisole, propyl gallate, and elisorbic acid.

Examples of pH adjusters include citric acid, sodium citrate, malic acid, sodium malate, fumal acid, sodium fumalate, succinic acid, sodium succinate, sodium hydroxide, and sodium monohydrogen phosphate.

Examples of alcohol include higher alcohols such as cetyl alcohol.

In addition, the mixing ingredients that may be added are not limited to this, and any of the above ingredients can be mixed within a range that does not impair the purpose and effect of the present invention, but is preferably 0.01 to 5% weight percentage based on the total weight, More preferably, it is formulated at a weight percentage of 0.01 - 3%.

The cosmetic of the present invention may take the form of a solution, emulsion, viscous mixture, etc.

Ingredients included in the cosmetic composition of the present invention may include ingredients commonly used in cosmetic compositions in addition to the compounds of the general formula (I) as active ingredients, such as stabilizers, solubilizers, vitamins, and pigments. and conventional auxiliaries and carriers such as flavorings.

The cosmetic composition of the present invention can be manufactured in any formulation commonly manufactured in the art, and examples include emulsions, creams, lotions, packs, foundations, lotions, beauty essences, hair cosmetics, etc.

Specifically, the cosmetic composition of the present invention includes skin lotion, skin softener, skin toner, astringent, lotion, milk lotion, moisture lotion, nutritional lotion, massage cream, nutritional cream, moisture cream, hand cream, foundation, essence, nutritional essence, It includes formulations of packs, soaps, cleansing foams, cleansing lotions, cleansing creams, body lotions, and body cleansers.

When the formulation of the present invention is a paste, cream or gel, animal fiber, plant fiber, wax, paraffin, starch, tracant, cellulose derivative, polyethylene glycol, silicone, bentonite, silica, talc or zinc oxide may be used as the carrier ingredient. You can.

When the formulation of the present invention is a powder or spray, lactose, talc, silica, aluminum hydroxide, calcium silicate, or polyamide powder can be used as the carrier ingredient. In particular, when the formulation is a spray, chlorofluorohydrocarbon and propane may be used as carrier ingredients. /May contain propellants such as butane or dimethyl ether.

When the formulation of the present invention is a solution or emulsion, a solvent, solvating agent or 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, glycerol aliphatic esters, polyethylene glycol or fatty acid esters of sorbitan.

When the formulation of the present invention is a suspension, the carrier ingredients include 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, and microcrystalline Cellulose, aluminum metahydroxide, bentonite, agar, or tracant may be used.

When the formulation of the present invention is a surfactant-containing cleansing agent, the carrier ingredients include aliphatic alcohol sulfate, aliphatic alcohol ether sulfate, sulfosuccinic acid monoester, isethionate, imidazolinium derivative, methyl taurate, sarcosinate, and fatty acid amide. Ether sulfate, alkylamidobetaine, fatty alcohol, fatty acid glyceride, fatty acid diethanolamide, vegetable oil, linoline derivative, or ethoxylated glycerol fatty acid ester can be used.

Hereinafter, the present invention will be described in detail through the following examples and experimental examples.

However, the following examples and experimental examples are merely illustrative of the present invention, and the content of the present invention is not limited by the following examples and experimental examples.

Example 1. Preparation of methyl 3,4,5-trimethoxybenzoate

Add 10 mmol of 3,4,5-trimethoxybenzoic acid to a two-necked round flask at room temperature, then add 50 ml of dimethylformamide. After adding 24 mmol of potassium carbonate (K2CO3) as a catalyst, 24 mmol of bromo methane was slowly added dropwise. After the dropwise addition was completed, the reaction was performed at room temperature for 6 hours. 500 ml of purified water was added to the reaction material, and extraction was performed using 100 ml of n-hexane. After drying the hexane layer under reduced pressure, silica gel column chromatography was performed using a mixed solvent of n-hexane and ethyl acetate as a developing solvent to obtain methyl 3,4,5-trimethoxy benzoate, and fast atom impact mass spectrometry (hereinafter referred to as , FAB-MS) was used to identify it.

FAB mass: 227 [M+H] ⁺

Example 2. Preparation of ethyl 3,4,5-trimethoxybenzoate

Ethyl 3,4,5-trimethoxy benzoate having the following physical properties was obtained by synthesizing in the same manner as in Example 1, except that bromo ethane was used instead of bromo methane.

FAB mass: 241 [M+H] ⁺

Example 3. Preparation of propyl 3,4,5-trimethoxybenzoate

Propyl 3,4,5-trimethoxy benzoate having the following physical properties was obtained by synthesizing in the same manner as in Example 1, except that bromopropane was used instead of bromomethane.

FAB mass: 255 [M+H] ⁺

Example 4. Preparation of butyl 3,4,5-trimethoxybenzoate

Butyl 3,4,5-trimethoxy benzoate having the following physical properties was obtained by synthesis in the same manner as in Example 1, except that bromobutane was used instead of bromomethane.

FAB mass: 269 [M+H] ⁺

Example 5. Preparation of pentyl 3,4,5-trimethoxybenzoate

Pentyl 3,4,5-trimethoxy benzoate having the following physical properties was obtained by synthesis in the same manner as in Example 1, except that bromopentane was used instead of bromomethane.

FAB mass: 283 [M+H] ⁺

Example 6. Preparation of methyl 3,4,5-trimethoxycinnamate

It was synthesized in the same manner as in Example 1, except that 3,4,5-trimethoxycinnamic acid was used instead of 3,4,5-trimethoxy benzoic acid, and the following physical properties were obtained. Methyl 3,4,5-trimethoxy cinnamate having was obtained.

FAB mass: 253 [M+H] ⁺

Example 7. Preparation of ethyl 3,4,5-trimethoxycinnamate

Ethyl 3,4,5-trimethoxy cinnamate having the following physical properties was obtained by synthesis in the same manner as in Example 6 except that bromo ethane was used instead of bromo methane, and the characteristics are shown below.

FAB mass: 267 [M+H] ⁺

Example 8. Preparation of propyl 3,4,5-trimethoxy cinnamate

Propyl 3,4,5-trimethoxy cinnamate having the following physical properties was obtained by synthesizing in the same manner as in Example 6, except that bromopropane was used instead of bromomethane.

FAB mass: 281 [M+H] ⁺

Example 9. Preparation of butyl 3,4,5-trimethoxy cinnamate

Butyl 3,4,5-trimethoxy cinnamate having the following physical properties was obtained by synthesis in the same manner as in Example 6, except that bromobutane was used instead of bromomethane.

FAB mass: 295 [M+H] ⁺

Example 10. Preparation of pentyl 3,4,5-trimethoxy cinnamate

Pentyl 3,4,5-trimethoxy cinnamate having the following physical properties was obtained by synthesizing in the same manner as in Example 6, except that bromopentane was used instead of bromomethane.

FAB mass: 309 [M+H] ⁺

Experimental Example 1. Antioxidant effect - free radical scavenging rate

Free radical scavenging activity was measured to confirm the antioxidant activity of the compounds prepared according to the methods described in Examples 1 to 10. Free radical scavenging activity was measured using DPPH. DPPH was purchased and used from Sigma. First, a 1.5mM standard DPPH ethanol solution was prepared. Then, ethanol was added to the compounds of Examples 1 to 34 and the antioxidant ascorbic acid as a reference material, respectively, to prepare samples at concentrations of 50ppm, 25ppm, 12.5ppm, 6.25ppm, and 3.125ppm. Next, the above sample and the standard DPPH solution were added in the same ratio and stirred, reacted at 37 ^o C for 30 minutes, and absorbance was measured at 520 nm. At this time, ethanol was added instead of the above sample as a control. The free radical scavenging ability was determined by calculating IC ₅₀ , which is the half maximal inhibitory concentration (median inhibition value), and the results are shown in Table 2 below. IC ₅₀ is a general method of expressing free radical scavenging ability as the concentration of ascorbic acid and the compounds of Examples 1 to 10 required to remove 50% of free radicals in the no-added control group.

Free radical scavenging rate (IC ₅₀ ) sample Free radical scavenging rate (ppm) Ascorbic acid 7 Material of Example 1 8 Material of Example 2 9 Material of Example 3 8 Material of Example 4 8 Material of Example 5 9 Material of Example 6 9 Material of Example 7 9 Material of Example 8 10 Material of Example 9 8 Material of Example 10 8

As shown in Table 1, the compounds of Examples 1 to 10 can be confirmed to have antioxidant effects.

Experimental Example 2. Anti-inflammatory effect - NO production inhibition effect

In order to confirm the anti-inflammatory effect and skin trouble alleviating effect of the compounds prepared according to the methods described in Examples 1 to 10, a nitric oxide (NO) formation inhibition test was performed by the GRISS method using the RAW264.7 cell line. Specifically, RAW264.7 cells, which are mouse macrophages, were subcultured several times, placed in a 24-well plate with 3x10 ⁵ cells per well, and cultured for 24 hours. Next, the cells were replaced with cell medium containing the compounds of Examples 1 to 34 diluted to the concentrations shown in Table 3 below. The concentration refers to the concentration of the compound dissolved in the medium used for evaluation, meaning 0.01% = 0.1 mg/ml, 0.001% = 0.01 mg/ml. Meanwhile, L-NMMA (L-NG-Monomethylarginine), an NO-production inhibitor, was treated as a positive control and cultured for 30 minutes, and 1 μg of LPS (Lipopolysaccharide) was treated as a stimulant and cultured for 24 hours. 100 μl of the supernatant was taken and transferred to a 96-well plate, 100 μl of GRIESS solution was added, reacted at room temperature for 10 minutes, and absorbance was measured at 540 nm. The NO inhibition effect of the compounds of Examples 1 to 10 was determined compared to the negative control group treated with only LPS and no NO inhibitor material, and the results are shown in Table 3 below.

NO production inhibition effect sample density(%) NO production inhibition rate (%) L-NMMA 0.001 38.6 Example 1 Compound 0.01 56.7 0.001 15.7 Example 2 Compound 0.01 49.7 0.001 13.4 Example 3 Compound 0.01 48.4 0.001 12.7 Example 4 Compound 0.01 39.8 0.001 11.8 Example 5 Compound 0.01 41.2 0.001 9.8 Example 6 Compound 0.01 38.9 0.001 7.6 Example 7 Compound 0.01 29.7 0.001 5.8 Example 8 Compound 0.01 26.8 0.001 6.2 Example 9 Compound 0.01 49.8 0.001 16.2 Example 10 Compound 0.01 39.8 0.001 14.8

Preparation Example 1. Preparation of flexible lotion

Formulation 1 and Comparative Formulation 1 were prepared with the compositions shown in Table 3 below.

Composition (% by weight) Formulation 1 Comparative formulation 1 a b c d Material of Example 2 0.5 - - - - Material of Example 4 - 0.5 - - - Material of Example 6 - - 0.5 - - Material of Example 8 - - - 0.5 - ethanol 10.0 10.0 10.0 10.0 10.0 Polyoxyethylene hydrogenated castor oil 1.0 1.0 1.0 1.0 1.0 Methyl paraoxybenzoate 0.2 0.2 0.2 0.2 0.2 glycerin 5.0 5.0 5.0 5.0 5.0 1,3-butylene glycol 6.0 6.0 6.0 6.0 6.0 incense Appropriate amount Appropriate amount Appropriate amount Appropriate amount Appropriate amount Purified water to 100 to 100 to 100 to 100 to 100

Preparation Example 2. Preparation of nutritional lotion

Formulation 2 and Comparative Formulation 2 were prepared with the compositions shown in Table 4 below.

Composition (% by weight) Formulation 2 Comparative formulation 2 a b c d Material of Example 2 0.5 - - - - Material of Example 4 - 0.5 - - - Material of Example 6 - - 0.5 - - Material of Example 8 - - - 0.5 - Polyoxyethylene hydrogenated castor oil 1.0 1.0 1.0 1.0 1.0 Methyl paraoxybenzoate 0.2 0.2 0.2 0.2 0.2 glycerin 6.0 6.0 6.0 6.0 6.0 1,3-butylene glycol 5.0 5.0 5.0 5.0 5.0 carbomer 0.2 0.2 0.2 0.2 0.2 Triethanolamine 0.3 0.3 0.3 0.3 0.3 propylene glycol 5.0 5.0 5.0 5.0 5.0 ethanol 3.2 3.2 3.2 3.2 3.2 Carboxy vinyl polymer 0.1 0.1 0.1 0.1 0.1 incense Appropriate amount Appropriate amount Appropriate amount Appropriate amount Appropriate amount Purified water to 100 to 100 to 100 to 100 to 100

Preparation Example 3. Preparation of cream

Formulation 3 and Comparative Formulation 3 were prepared with the compositions shown in Table 5 below.

Composition (% by weight) Formulation 3 Comparative formulation 3 a b c d Material of Example 2 0.5 - - - - Material of Example 4 - 0.5 - - - Material of Example 6 - - 0.5 - - Material of Example 8 - - - 0.5 - Cetanol 2.0 2.0 2.0 2.0 2.0 PEG-20 1.0 1.0 1.0 1.0 1.0 sorbitan monostearate 1.0 1.0 1.0 1.0 1.0 mineral oil 10.0 10.0 10.0 10.0 10.0 Trioctanoate 5.0 5.0 5.0 5.0 5.0 Triethanolamine 0.5 0.5 0.5 0.5 0.5 carbomer 0.2 0.2 0.2 0.2 0.2 glycerin 5.0 5.0 5.0 5.0 5.0 propylene glycol 3.0 3.0 3.0 3.0 3.0 antiseptic Appropriate amount Appropriate amount Appropriate amount Appropriate amount Appropriate amount incense Appropriate amount Appropriate amount Appropriate amount Appropriate amount Appropriate amount Purified water to 100 to 100 to 100 to 100 to 100

Preparation Example 4. Preparation of external skin ointment

Formulation 4 and Comparative Formulation 4 were prepared with the compositions shown in Table 6 below.

Composition (% by weight) Formulation 4 Comparative formulation 4 a b c d Material of Example 2 0.5 - - - - Material of Example 4 - 0.5 - - - Material of Example 6 - - 0.5 - - Material of Example 8 - - - 0.5 - diethyl sebacate 8.0 8.0 8.0 8.0 8.0 Gyeongap 5.0 5.0 5.0 5.0 5.0 Polyoxyethylene oleyl ether phosphate 6.0 6.0 6.0 6.0 6.0 sodium benzoate Appropriate amount Appropriate amount Appropriate amount Appropriate amount Appropriate amount vaseline to 100 to 100 to 100 to 100 to 100

Preparation Example 5. Preparation of essence

Formulation 5 and Comparative Formulation 5 were prepared with the compositions shown in Table 7 below.

Composition (% by weight) Formulation 5 Comparative formulation 5 a b c d Material of Example 2 0.5 - - - - Material of Example 4 - 0.5 - - - Material of Example 6 - - 0.5 - - Material of Example 8 - - - 0.5 - propylene glycol 10.0 10.0 10.0 10.0 10.0 glycerin 10.0 10.0 10.0 10.0 10.0 Sodium hyaluronate aqueous solution (1%) 5.0 5.0 5.0 5.0 5.0 ethanol 5.0 5.0 5.0 5.0 5.0 Polyoxyethylene hydrogenated castor oil 1.0 1.0 1.0 1.0 1.0 Methyl paraoxybenzoate 0.1 0.1 0.1 0.1 0.1 carbomer 0.4 0.4 0.4 0.4 0.4 incense Appropriate amount Appropriate amount Appropriate amount Appropriate amount Appropriate amount Purified water to 100 to 100 to 100 to 100 to 100

Preparation Example 6. Preparation of pack

Formulation 6 and Comparative Formulation 6 were prepared with the compositions shown in Table 8 below.

Composition (% by weight) Formulation 6 Comparative formulation 6 a b c d Material of Example 2 0.5 - - - - Material of Example 4 - 0.5 - - - Material of Example 6 - - 0.5 - - Material of Example 8 - - - 0.5 - glycerin 5.0 5.0 5.0 5.0 5.0 propylene glycol 4.0 4.0 4.0 4.0 4.0 polyvinyl alcohol 15.0 15.0 15.0 15.0 15.0 ethanol 8.0 8.0 8.0 8.0 8.0 Polyoxyethylene hydrogenated castor oil 1.0 1.0 1.0 1.0 1.0 Polyoxyethylene oleyl ether phosphate 1.0 1.0 1.0 1.0 1.0 Methyl paraoxybenzoate 0.2 0.2 0.2 0.2 0.2 incense Appropriate amount Appropriate amount Appropriate amount Appropriate amount Appropriate amount Purified water to 100 to 100 to 100 to 100 to 100

Claims (5)

A derivative of a compound represented by the following general formula (I) or a pharmacologically acceptable salt thereof.
(I)
In the above formula, R _1, R _2, R ₃ are C1 to C3 saturated or unsaturated straight-chain or branched alkyl groups, R ₄ is selected from R ₅ , saturated or unsaturated straight-chain or branched alkoxy, and R ₅ Is or structure, and R ₆ is hydrogen, C1 to C5 saturated or unsaturated straight-chain or branched alkyl.
An antioxidant and anti-inflammatory composition containing as an active ingredient at least one derivative of a compound represented by the following general formula (I).
(I)
In the above formula, R _1, R _2, R ₃ are C1 to C3 saturated or unsaturated straight-chain or branched alkyl groups, R ₄ is selected from R ₅ , saturated or unsaturated straight-chain or branched alkoxy, and R ₅ Is or structure, and R ₆ is hydrogen, C1 to C5 saturated or unsaturated straight-chain or branched alkyl. The method of claim 1 or 2, wherein the compound is methyl 3,4,5-trimethoxy benzoate, ethyl 3,4,5-trimethoxy benzoate, propyl 3,4,5-trimethoxy benzoate. ate, butyl 3,4,5-trimethoxy benzoate, pentyl 3,4,5-trimethoxy benzoate, methyl 3,4,5-trimethoxy cinnamate, ethyl 3,4,5-trime Compounds that are toxy cinnamate, propyl 3,4,5-trimethoxy cinnamate, butyl 3,4,5-trimethoxy cinnamate, and pentyl 3,4,5-trimethoxy cinnamate. An antioxidant and/or anti-inflammatory composition comprising the compound according to any one of claims 1 to 3 or a pharmacologically acceptable salt thereof as an active ingredient.
An antioxidant and anti-inflammatory composition, characterized in that the compound according to any one of claims 1 to 4 is contained in an amount of 0.0001 to 10% by weight based on the total weight of the composition.