Compositions for suppressing sebum secretion containing thymol ester based compound

Abstract

To provide a sebum secretion-inhibiting composition containing, as an effective ingredient, 3, 4, 5-trimethoxycinnamate thymol ester, or a stereoisomer, pharmaceutically acceptable salt, hydrate or solvate thereof.SOLUTION: The disclosed compositions can inhibit sebum secretion of skin or scalp exerting useful effects such as prevention or amelioration of seborrheic dermatitis, seborrheic scalp inflammation, prevention or amelioration of acne, or pore-shrinking.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] Disclosed herein is a composition for suppressing sebum secretion, which comprises, as an active ingredient, 3,4,5-trimethoxycinnamate thymol ester or a stereoisomer, pharmaceutically acceptable salt, hydrate, or solvate thereof. [Background technology]

[0002] Sebum, secreted from the sebaceous glands, plays an important role in keeping the skin moisturized and hydrated, as well as protecting it from external microorganisms. However, excessive sebum secretion can also cause various skin diseases, such as acne and seborrheic scalp.

[0003] To solve this problem, much research has been conducted and various substances have been developed as sebum-inhibiting substances, but no substance that meets all needs has been found to date. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Korean Patent No. 10-2006954 Summary of the Invention [Problem to be solved by the invention]

[0005] One aspect of the present disclosure aims to provide a composition that can suppress or prevent sebum-related diseases such as seborrheic dermatitis by suppressing sebum secretion from the skin or scalp. [Means for solving the problem]

[0006] In one aspect, the present disclosure provides a composition for suppressing sebum secretion, comprising 3,4,5-trimethoxycinnamate thymol ester, a stereoisomer, a pharmaceutically acceptable salt, a hydrate, or a solvate thereof as an active ingredient. [Effects of the Invention]

[0007] In one aspect, the compositions according to the present disclosure can suppress sebum secretion on the skin or scalp.

[0008] In one aspect, the composition according to the present disclosure can care for oily skin or an oily scalp.

[0009] In one aspect, the compositions according to the present disclosure can prevent or improve seborrheic dermatitis, seborrheic scalp, or acne.

[0010] In one aspect, the compositions according to the present disclosure can promote pore contraction in the skin. [Brief explanation of the drawings]

[0011] [Figure 1] FIG. 1 is a graph showing the results of observing the sebum secretion suppression effect of a composition according to an example of the present disclosure. [Figure 2] FIG. 1 is a graph showing the results of observing the sebum secretion suppression effect of a composition according to an example of the present disclosure. DETAILED DESCRIPTION OF THE INVENTION

[0012] The present disclosure will be described in more detail below with reference to the following examples. However, the following examples are merely illustrative examples to aid in understanding the present disclosure, and are not intended to limit the scope of the present disclosure.

[0013] In an exemplary embodiment of the present disclosure, there is provided a composition for suppressing sebum secretion, comprising 3,4,5-trimethoxycinnamate thymol ester, a stereoisomer thereof, a pharmaceutically acceptable salt, a hydrate, or a solvate thereof as an active ingredient.

[0014] Another exemplary implementation of the present disclosure provides a method for suppressing sebum secretion, comprising administering a composition comprising 3,4,5-trimethoxycinnamate thymol ester, a stereoisomer, a pharmaceutically acceptable salt, a hydrate, or a solvate thereof as an active ingredient.

[0015] Another exemplary embodiment of the present disclosure provides a use of 3,4,5-trimethoxycinnamate thymol ester, its stereoisomers, pharmaceutically acceptable salts, hydrates, or solvates for preparing a composition for suppressing sebum secretion.

[0016] Another exemplary implementation of the present disclosure provides a non-therapeutic use of 3,4,5-trimethoxycinnamate thymol ester, its stereoisomers, pharmaceutically acceptable salts, hydrates or solvates for suppressing sebum secretion.

[0017] Another exemplary implementation of the present disclosure provides 3,4,5-trimethoxycinnamate thymol ester, its stereoisomers, pharmaceutically acceptable salts, hydrates or solvates for suppressing sebum secretion.

[0018] In one embodiment, the 3,4,5-trimethoxycinnamic acid thymol ester is (5-methyl-2-propan-2-ylphenyl)(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate, represented by the following general formula (1):

[0019] [ka]

[0020] As used herein, the term "isomer" includes in particular optical isomers (e.g., essentially pure enantiomers, essentially pure diastereomers or mixtures thereof), but also conformation isomers (i.e., isomers that differ only in the angle of at least one chemical bond), position isomers (especially tautomers) or geometric isomers (e.g., cis-trans isomers).

[0021] As used herein, the term "essentially pure," when used in connection with, for example, an enantiomer or diastereomer, means that the specific compound, exemplified by the enantiomer or diastereomer, is present in an amount of about 90% or more, preferably about 95% or more, more preferably about 97% or more or about 98% or more, even more preferably about 99% or more, and most preferably about 99.5% or more (w / w).

[0022] As used herein, the term "pharmaceutically acceptable" means capable of being approved by, or approved by, a governmental or equivalent regulatory body for use in animals, and more particularly in humans, by avoiding significant toxic effects when used in normal medicinal dosages, or is listed in a pharmacopoeia or other generally recognized pharmacopoeia.

[0023] The term "pharmaceutically acceptable salt" as used herein refers to a salt according to one embodiment of the present disclosure that is pharmaceutically acceptable and possesses the desired pharmacological activity of the parent compound. The salt may be formed from (1) an inorganic acid such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid, or the like; or from an acid such as acetic acid, propionic acid, hexanoic acid, cyclopentenepropionic acid, glycolic acid, pyruvic acid, lactic acid, malonic acid, succinic acid, malic acid, maleic acid, fumaric acid, tartaric acid, citric acid, benzoic acid, 3-(4-hydroxybenzoyl)benzoic acid, cinnamic acid, mandelic acid, methanesulfonic acid, ethanesulfonic acid, 1,2-ethanedisulfonic acid, 2-hydroxyethanesulfonic acid, or the like. or (2) salts formed when an acidic proton present in the parent compound is replaced by another acid.

[0024] As used herein, the term "hydrate" refers to a compound in which water is bound, and is a broad concept that includes an endocrine compound in which there is no chemical bonding between the water and the compound.

[0025] As used herein, the term "solvate" refers to a higher-order compound formed between molecules or ions of a solute and molecules or ions of a solvent.

[0026] In one implementation, the composition may be for preventing or ameliorating seborrheic dermatitis, seborrheic scalp, folliculitis, acne, or seborrheic eczema.

[0027] In one implementation, the composition may be for the care of oily skin or an oily scalp.

[0028] In one implementation, the composition may be for pore shrinkage.

[0029] In one implementation, the composition may suppress sebum secretion due to linoleic acid.

[0030] In one implementation, the composition may reduce sebum secretion caused by the linoleic acid by 40% or more.

[0031] For example, the composition may reduce sebum secretion caused by the linoleic acid by 40% or more, 45% or more, 50% or more, 55% or more, or 60% or more, or 99% or less.

[0032] In one embodiment, the concentration of the active ingredient may be 0.01 to 5% by weight based on the total weight of the composition.

[0033] For example, the concentration of the active ingredient may be 0.01% by weight or more, 0.05% by weight or more, 0.1% by weight or more, 0.5% by weight or more, 1% by weight or more, 2% by weight or more, 3% by weight or more, or 4% by weight or more, and may be 5% by weight or less, 4% by weight or less, 3% by weight or less, 2% by weight or less, 1% by weight or less, 0.5% by weight or less, 0.1% by weight or less, or 0.05% by weight or less, based on the total weight of the composition.

[0034] In one implementation, the composition may be a topical skin composition.

[0035] In one embodiment, the composition may be a non-therapeutic transdermal composition.

[0036] The topical skin preparation or transdermal composition is a general term that may include anything that is applied to the outer skin, and may include cosmetics of various formulations.

[0037] In one implementation, the composition may be a cosmetic composition.

[0038] The cosmetic composition may comprise a cosmetically or dermatologically acceptable vehicle or base. This may be any formulation suitable for topical application, such as a solution, gel, solid, anhydrous product, emulsion obtained by dispersing an oily phase in an aqueous phase, suspension, microemulsion, microcapsule, microgranule, or ionic (liposomal) and non-ionic vesicular dispersion, or in the form of a cream, lotion, emulsion, powder, ointment, spray, or stick concealer. These compositions may be prepared according to conventional methods in the art. The compositions according to the present disclosure may also be used in the form of foam or in the form of an aerosol composition further comprising a compressed propellant.

[0039] The cosmetic composition according to one embodiment of the present disclosure is not particularly limited in its formulation, and may be formulated into cosmetics such as, for example, a softening lotion, an astringent lotion, a nourishing lotion, a nourishing cream, a massage cream, a serum, an eye cream, an eye essence, a cleansing cream, a cleansing foam, a cleansing water, a face mask, a powder, a body lotion, a body cream, a body oil, or a body essence.

[0040] When the cosmetic composition of the present disclosure is formulated as a paste, cream, or gel, animal fibers, plant fibers, wax, paraffin, starch, tragacanth, cellulose derivatives, polyethylene glycol, silicone, bentonite, silica, talc, zinc oxide, or the like may be used as a carrier component.

[0041] When the cosmetic composition of the present disclosure is formulated as a powder or spray, lactose, talc, silica, aluminum hydroxide, calcium silicate, or polyamide powder may be used as a carrier component, and particularly in the case of a spray, a propellant such as hydrochlorofluorocarbon, propane / butane, or dimethyl ether may be further included.

[0042] When the cosmetic composition of the present disclosure is formulated as a solution or emulsion, a solvent, solvating agent, or emulsifier is used as a carrier component, and examples thereof include water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1,3-butyl glycol oil, glycerin fatty acid esters, polyethylene glycol, and fatty acid esters of sorbitan.

[0043] When the cosmetic composition of the present disclosure is formulated as a suspension, a liquid diluent such as water, ethanol, or propylene glycol, a suspending agent such as ethoxylated stearyl alcohol, polyoxyethylene sorbitol ester, or polyoxyethylene sorbitan ester, or microcrystalline cellulose, aluminum metahydroxide, bentonite, agar, or tragacanth may be used as a carrier component.

[0044] When the formulation of the cosmetic composition of the present disclosure is a surfactant-containing cleanser, the carrier component may be a fatty alcohol sulfate, a fatty alcohol ether sulfate, a sulfosuccinate monoester, an isethionate, an imidazolium derivative, a methyl taurate, a sarcosinate, a fatty acid amide ether sulfate, an alkylamidobetaine, a fatty alcohol, a fatty acid glyceride, a fatty acid diethanolamide, a vegetable oil, a lanolin derivative, or an ethoxylated glycerin fatty acid ester.

[0045] In addition to the active ingredient, the cosmetic composition of the present disclosure may further include functional additives and ingredients commonly found in cosmetic compositions. The functional additives may include ingredients selected from the group consisting of water-soluble vitamins, oil-soluble vitamins, polymeric peptides, polymeric polysaccharides, sphingolipids, and seaweed extracts.

[0046] The cosmetic composition of the present disclosure may further contain, in addition to the functional additives, ingredients typically found in cosmetic compositions, as needed. Examples of other ingredients include oils and fats, moisturizers, emollients, surfactants, organic and inorganic pigments, organic powders, UV absorbers, preservatives, disinfectants, antioxidants, plant extracts, pH adjusters, alcohols, colorants, fragrances, blood circulation enhancers, cooling agents, antiperspirants, purified water, etc.

[0047] In one embodiment, the composition may be a food composition.

[0048] In one embodiment, the composition may be a non-therapeutic oral composition.

[0049] The food composition or non-therapeutic oral composition according to the present disclosure may be a liquid or solid formulation, and may be a tablet, capsule, soft capsule, pill, granule, beverage (drinkable), diet bar, chocolate, caramel formulation or confectionery formulation, and the formulation is not particularly limited.

[0050] The food composition or non-therapeutic oral composition according to the present disclosure may further contain excipients, sugars, flavorings, colorants, oils and fats, proteins, etc., as needed, in addition to the active ingredient.

[0051] In one embodiment, the 3,4,5-trimethoxycinnamate thymol ester, its stereoisomer, pharmaceutically acceptable salt, hydrate or solvate may be applied or ingested at a dose of 0.01 to 10 mg / kg.

[0052] In one implementation, the composition may be a pharmaceutical composition.

[0053] The pharmaceutical composition according to one embodiment of the present disclosure may further contain pharmaceutical adjuvants such as preservatives, stabilizers, hydrating agents or emulsifying agents, salts for adjusting osmotic pressure and / or buffering agents, and other therapeutically useful substances, and may be formulated into various oral or parenteral dosage forms according to conventional methods.

[0054] The oral dosage forms include, for example, tablets, pills, hard and soft capsules, liquids, suspensions, emulsions, syrups, powders, fine granules, granules, and pellets. These preparations may contain, in addition to the active ingredient, surfactants, diluents (e.g., lactose, dextrose, sucrose, mannitol, sorbitol, cellulose, and glycine), and lubricants (e.g., silica, talc, stearic acid and its magnesium or calcium salt, and polyethylene glycol). Tablets may further contain binders such as magnesium aluminum silicate, starch paste, gelatin, tragacanth, methylcellulose, sodium carboxymethylcellulose, and polyvinylpyrrolidine, and, in some cases, pharmaceutical additives such as disintegrants (e.g., starch, agar, alginic acid or its sodium salt), absorbents, colorants, flavorings, and sweeteners. The tablets may be prepared by conventional mixing, granulating, or coating methods.

[0055] Furthermore, the parenteral administration form may be a transdermal administration preparation, such as an injection, drip infusion, ointment, lotion, gel, cream, spray, suspension, emulsion, suppository, patch, etc., but is not limited to these.

[0056] In one embodiment, the daily dosage of the active ingredient may be 0.01 to 10 mg / kg of 3,4,5-trimethoxycinnamate thymol ester, its stereoisomer, pharmaceutically acceptable salt, hydrate, or solvate.

[0057] The present disclosure will be described in more detail below with reference to the following examples. However, the following examples are merely illustrative examples to aid in understanding the present disclosure, and are not intended to limit the scope of the present disclosure.

[0058] [Example] Preparation of 3,4,5-Trimethoxycinnamate Thymol Ester Thymol trimethoxycinnamate thymol ester (Melasolv) with CAS number 504394-57-4 was obtained from COSMANN Co., Ltd. (Hwaseong, Gyeonggi-do).

[0059] [Experimental Example] 1. Testing the sebum secretion inhibitory effect using human sebocytes Human sebocytes were cultured in Sebocyte Complete Culture Media (Celprogen) at 37°C in a 5% CO2 environment for 24 hours, and then treated with 100 μM linoleic acid and 0.1, 0.5, 1, or 2 ppm Melasorb, and cultured for a further 48 hours.

[0060] Then, formaldehyde-fixed cells were stained with 2 μM Bodipy for lipids, and the fluorescence intensity was measured at specific wavelengths (Excitation / Emission: 485 / 528 nm) using a fluorescent plate reader.

[0061] Data are presented as percentages compared to the control group (100%) in which no samples were treated.

[0062] Referring to Figure 1 (in vitro sebum secretion inhibitory effect test), when sebocytes were treated with 100 μM linoleic acid, a significant increase in sebum production (142%) was observed. Based on the amount of sebum production induced by linoleic acid, when the inducer and Melasorb were treated together, sebum production decreased in proportion to the concentration when Melasorb was treated at 0.1, 0.5, 1, or 2 ppm, and at a maximum of 2 ppm, Melasorb demonstrated a sebum production inhibitory effect of approximately 60.3%. These results confirmed that Melasorb has the ability to inhibit sebum production.

[0063] The fluorescence intensity results in Figure 1 can be visually confirmed from the fluorescence photograph in Figure 2, and it was confirmed that sebum production was most suppressed at 2 ppm of Melasorb.

Claims

1. A composition for inhibiting sebum secretion, comprising 3,4,5-trimethoxycinnamate thymol ester, or a stereoisomer, pharmaceutically acceptable salt, hydrate, or solvate thereof as an active ingredient.

2. The composition according to claim 1, wherein the composition is for preventing or improving seborrheic dermatitis, seborrheic scalp inflammation, folliculitis, acne or seborrheic eczema.

3. The composition according to claim 1, wherein the composition is for the care of oily skin or oily scalp.

4. The composition of claim 1 , wherein the composition is for shrinking pores.

5. 2. The composition according to claim 1, wherein the concentration of the active ingredient is from 0.01 to 5% by weight relative to the total weight of the composition.

6. The composition according to claim 1 , wherein the composition is a topical skin preparation.

7. The composition of claim 1 , wherein the composition is a cosmetic composition.

8. The composition of claim 1 , wherein the composition is a food composition.

9. The composition of claim 1 , wherein the composition is a pharmaceutical composition.

10. The composition according to claim 1, wherein the daily dose of the active ingredient is 0.01 to 10 mg / kg.

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