Cosmetic composition for antioxidation

Abstract

The present invention relates to a cosmetic composition having antioxidant activity. Provided according to the present invention is a cosmetic composition that has 2,2-diphenyl-1-picrylhydrazyl radical scavenging ability and thus exhibits an excellent antioxidant effect.

Description

Antioxidant cosmetic composition

[0001] Cross-citation with related applications

[0002] This application claims the benefit of priority to Republic of Korea Patent Application No. 10-2023-0120961, filed September 12, 2023, Republic of Korea Patent Application No. 10-2024-0099303, filed July 26, 2024, and Republic of Korea Patent Application No. 10-2024-0099304, filed July 26, 2024, the entire contents of which are incorporated herein by reference.

[0003]

[0004] The present invention relates to a cosmetic composition having antioxidant activity.

[0005]

[0006] Oxygen is absolutely necessary for the survival of all living organisms on Earth.

[0007] However, ground state triplet oxygen, a stable molecular state, is converted into highly reactive reactive oxygen species such as superoxide radicals, hydroxyl radicals, hydrogen peroxide, and singlet oxygen by various factors such as reductive metabolism, body enzymes, chemicals, photochemical reactions, and pollutants. Reactive oxygen species cause oxygen toxicity that is fatal to living organisms.

[0008] Active oxygen species are known to cause non-selective and irreversible destruction of cellular components such as proteins, lipids, sugars, and DNA, and cause aging and various diseases.

[0009] Even normal cells generate some free radicals and reactive oxygen species during metabolic processes. However, antioxidant enzymes such as superoxide dismutase exist within the body as defense mechanisms against reactive oxygen species. Furthermore, substances such as vitamin C and vitamin E are known to exert antioxidant effects within the body. However, when these defense mechanisms malfunction or the production of reactive oxygen species exceeds the capacity of the body's defense system, oxidative stress occurs.

[0010] The discovery of superoxide dismutase sparked a wave of research into antioxidants. Furthermore, with the growing recognition that reactive oxygen species contribute to aging and other diseases, research on antioxidants is now actively underway.

[0011] However, various commercial antioxidants have various problems such as human toxicity, low activity, and limited use, and there is still a great demand for antioxidant compositions free from these problems.

[0012]

[0013] The present invention provides an antioxidant cosmetic composition.

[0014] And, the present invention is to provide a pharmaceutical composition for antioxidant.

[0015]

[0016] According to one embodiment of the invention, an antioxidant cosmetic composition comprising 3-hydroxypropionic acid or a derivative thereof as an active ingredient is provided.

[0017] According to another embodiment of the invention, the use of 3-hydroxypropionic acid or a derivative thereof for the manufacture of an antioxidant cosmetic is provided.

[0018] According to another embodiment of the invention, a method for protecting skin from oxidative stress is provided using a cosmetic composition comprising 3-hydroxypropionic acid or a derivative thereof as an active ingredient.

[0019] According to another embodiment of the invention, an antioxidant pharmaceutical composition comprising 3-hydroxypropionic acid or a derivative thereof as an active ingredient is provided.

[0020] According to another embodiment of the invention, there is provided the use of 3-hydroxypropionic acid or a derivative thereof for the manufacture of an antioxidant agent.

[0021] According to another embodiment of the invention, a method for protecting a body from oxidative stress is provided using a pharmaceutical composition comprising 3-hydroxypropionic acid or a derivative thereof as an active ingredient.

[0022]

[0023] Hereinafter, the antioxidant cosmetic composition and the antioxidant pharmaceutical composition according to an embodiment of the invention will be described in more detail.

[0024]

[0025] The terms and words used in this specification and claims should not be interpreted as limited to their usual or dictionary meanings, but should be interpreted with meanings and concepts that conform to the technical idea of ​​the invention, based on the principle that the inventor can appropriately define the concept of the term to explain his or her own invention in the best way.

[0026] Unless otherwise defined herein, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. The terminology used herein is for the purpose of describing specific embodiments only and is not intended to be limiting.

[0027] The present invention is susceptible to various modifications and takes various forms. Specific embodiments are illustrated and described in detail below. However, this is not intended to limit the present invention to specific disclosed forms, but rather to encompass all modifications, equivalents, and alternatives falling within the spirit and scope of the invention.

[0028] As used herein, the singular forms also include the plural forms unless the context clearly dictates otherwise.

[0029] As used herein, the term "including" means specifying a particular characteristic, region, integer, step, operation, element and / or component, but does not exclude the presence or addition of other particular characteristics, regions, integers, steps, operations, elements, components and / or groups.

[0030] In this specification, when a temporal relationship is described as, for example, ‘after’, ‘following’, ‘next to’, or ‘before’, it may also include cases where it is not continuous, unless the expression ‘immediately’ or ‘directly’ is used.

[0031] In this specification, “derivative” means a compound that has been changed by a reaction such as introduction of a functional group, oxidation, reduction, or substitution of atoms in a parent compound of an organic compound, without significantly changing the structure and properties of the parent compound.

[0032] The term "comprising as an active ingredient" in this specification means that the composition according to an embodiment of the invention comprises 3-hydroxypropionic acid or a derivative thereof in an amount sufficient to achieve an antioxidant effect.

[0033] In this specification, "antioxidant" refers to protecting the body (e.g., skin) from oxidative stress. Oxidative stress occurs naturally during normal metabolic processes, but if excessively generated or accumulated, it can damage DNA and cells, leading to aging and chronic diseases. While the body possesses an antioxidant system that removes oxidizing substances, consuming antioxidants can prevent or inhibit the oxidation process.

[0034] As used herein, the term "prevention" refers to the suppression of symptoms caused by reactive oxygen species. As used herein, the term "treatment" refers to the alleviation or elimination of symptoms caused by reactive oxygen species that have already occurred. Furthermore, the term "improvement" as used herein refers to the alleviation or relief of symptoms caused by reactive oxygen species.

[0035]

[0036] As a result of the inventors' continued research, it was confirmed that 3-hydroxypropionic acid can exhibit excellent antioxidant effects, such as preventing, alleviating, or improving symptoms caused by active oxygen.

[0037] In particular, 3-hydroxypropionic acid has 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity, so a cosmetic composition containing 3-hydroxypropionic acid or a derivative thereof as an active ingredient can exhibit excellent antioxidant effects.

[0038]

[0039] According to one embodiment of the invention, an antioxidant cosmetic composition comprising 3-hydroxypropionic acid or a derivative thereof as an active ingredient is provided.

[0040]

[0041] The above-mentioned antioxidant cosmetic composition comprises 3-hydroxypropionic acid or a derivative thereof as an active ingredient. Preferably, the above-mentioned antioxidant cosmetic composition comprises 3-hydroxypropionic acid as an active ingredient.

[0042]

[0043] 3-Hydroxypropionic acid can be applied as an active ingredient by being synthesized by chemical or biological methods.

[0044] According to one embodiment, 3-hydroxypropionic acid obtained through a biological process such as fermentation of a strain having 3-hydroxypropionic acid production ability may be preferably used as the effective ingredient. 3-hydroxypropionic acid obtained by the above method is radioactive carbon isotope ( 14 C) may be included.

[0045] Preferably, the active ingredient may have a radioactive carbon isotope content of 20 pMC (percent modern carbon) or more as measured by ASTM D6866-21, and a biocarbon content of 20 wt% or more. Specifically, the active ingredient may have a radioactive carbon isotope content of 20 pMC or more as measured by ASTM D6866-21, or 50 pMC or more, or 90 pMC or more, or 100 pMC or more, or 90 to 110 pMC; and a biocarbon content of 20 wt% or more, or 50 wt% or more, or 80 wt% or more, or 90 wt% or more, or 95 wt% or more, or 90 to 100 wt%.

[0046] The above radiocarbon isotope content (pMC) is the radiocarbon isotope contained in 3-hydroxypropionic acid ( 14 C) and radiocarbon isotopes of modern reference materials ( 14C) refers to the ratio of radiocarbon isotope content. Note that the effects of the nuclear testing program in the 1950s are still ongoing and have not been dissipated, so the radioactive carbon isotope content (pMC) may be greater than 100%.

[0047] The above biocarbon content represents the content of biocarbon relative to the total carbon content contained in 3-hydroxypropionic acid, and a larger value may indicate that the compound is more environmentally friendly.

[0048] If the content of radioactive carbon isotopes (pMC) and biocarbon content of the above 3-hydroxypropionic acid is too low, the environmental friendliness is reduced and it may not be considered as a bio-derived material.

[0049] Radioactive carbon isotopes ( 14 C) 1X10 carbon atoms in the Earth's atmosphere 12 It is about 1 per 100, has a half-life of about 5700 years, and is oxidized by cosmic rays and ordinary nitrogen ( 14 N) can be abundant in the upper atmosphere due to nuclear reactions involving it.

[0050] Fossil fuels contain radioactive carbon isotopes that have decayed long ago. 14 The C ratio can be virtually zero. When using bio-derived materials as a raw material for 3-hydroxypropionic acid, or when using fossil fuels in combination with them, the content of radiocarbon isotopes (pMC) and biocarbon content in 3-hydroxypropionic acid can be measured using ASTM D6866-21.

[0051] The measurement method can be, for example, by making the carbon atoms contained in the target compound into the form of graphite or carbon dioxide gas and measuring them using a mass spectrometer, or by measuring them according to liquid scintillation spectrometry. In this case, 14 C ion 12An accelerator can be used to separate the C ions, and the two isotopes can be separated and their contents and content ratios can be measured using a mass spectrometer.

[0052]

[0053] The above-described antioxidant cosmetic composition can exhibit DPPH radical scavenging activity due to the action of the active ingredient. The DPPH radical exhibits a deep purple color. The DPPH radical is reduced by the antioxidant active ingredient, thereby discoloring the deep purple color. Using this characteristic, the performance of the antioxidant active ingredient can be measured.

[0054]

[0055] According to one embodiment, the cosmetic composition may contain 0.5 wt% to 80 wt% of the active ingredient based on the total weight of the cosmetic composition.

[0056] Specifically, the cosmetic composition may contain the effective ingredient in an amount of 0.5 wt% or more, or 1 wt% or more, and 80 wt% or less, or 75 wt% or less, or 70 wt% or less, based on the total weight of the cosmetic composition.

[0057] In order to ensure that the antioxidant effect can be sufficiently achieved by the action of the above-mentioned effective ingredient, it is preferable that the above-mentioned cosmetic composition contains 0.5 wt% or more or 1 wt% or more of the above-mentioned effective ingredient.

[0058] However, if the above-mentioned effective ingredient is included in excessive amounts, the antioxidant effect may be reduced or side effects may occur. Therefore, it is preferable that the above-mentioned cosmetic composition contain no more than 80% by weight, no more than 75% by weight, or no more than 70% by weight of the above-mentioned effective ingredient.

[0059] Preferably, the cosmetic composition may contain the effective ingredient in an amount of 0.5 wt% to 80 wt%, or 0.5 wt% to 75 wt%, or 1 wt% to 75 wt%, or 1 wt% to 70 wt% based on the total weight of the cosmetic composition.

[0060]

[0061] According to one embodiment, the cosmetic composition may have a cosmetic formulation conventional in the art to which the present invention pertains. For example, the cosmetic composition may have a formulation that is a solution, suspension, emulsion, paste, gel, cream, lotion, powder, oil, foam, pack, spray, aerosol, balm, solid soap, liquid soap, powder foundation, emulsion foundation, or wax foundation.

[0062] According to one embodiment, the cosmetic composition may include, in addition to the active ingredient, an organic solvent, a fatty substance, a solubilizer, a thickener, a gelling agent, an emollient, an antioxidant, a suspending agent, a stabilizer, a foaming agent, a fragrance, a surfactant, water, an emulsifier, a filler, a chelating agent, a preservative, a vitamin, a humectant, a dye, a pigment, a hydrophilic or lipophilic active agent, and the like. In addition, the cosmetic composition may contain an adjuvant commonly used in the field of cosmetology or dermatology.

[0063]

[0064] The cosmetic composition may further comprise a physiologically acceptable medium comprising water or a mixture of water and an organic solvent.

[0065] For example, the organic solvent may be applied as a lower alcohol having C1-C4 such as acetone, ethanol, and isopropyl alcohol, an alkylene glycol such as ethylene glycol and propylene glycol, ethylene glycol monomethyl ether, monoethyl ether, monobutyl ether, propylene glycol, etc. The physiologically acceptable medium may be applied in an amount of 1 to 90 wt% based on the total weight of the cosmetic composition.

[0066] The above medium can be thickened using a thickener commonly used in the cosmetics or pharmaceutical industries. The thickener can be applied in an amount of 0.1 to 5 wt% based on the total weight of the composition.

[0067] Additionally, depending on the various embodiments of the cosmetic composition, a person skilled in the art can select excipients generally required for preparing such compositions. For example, excipients may include preservatives, stabilizers, pH regulators, osmotic pressure modifiers, emulsifiers, sunscreens, antioxidants, fragrances, dyes, anionic surfactants, cationic surfactants, nonionic surfactants, and amphoteric surfactants.

[0068]

[0069] According to one embodiment, when the formulation of the cosmetic composition is a powder or spray, it may include a carrier component such as lactose, talc, silica, aluminum hydroxide, calcium silicate, polyamide powder, etc.

[0070] According to one embodiment, when the formulation of the cosmetic composition is a paste, gel, or cream, it may include a carrier component such as animal oil, vegetable oil, wax, paraffin, starch, tragacanth, cellulose derivative, polyethylene glycol, silicone, bentonite, silica, talc, zinc oxide, etc.

[0071] In one embodiment, when the formulation of the cosmetic composition is a solution or emulsion, it may include a carrier component such as a solvent, a solubilizer, or an emulsifier. For example, the formulation of the solution or emulsion may include water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1,3-butyl glycol oil, glycerol aliphatic ester, polyethylene glycol, or fatty acid ester of sorbitan.

[0072] According to one embodiment, when the formulation of the cosmetic composition is a suspension, a liquid diluent such as water, ethanol or propylene glycol; a suspending agent such as ethoxylated isostearyl alcohol, polyoxyethylene sorbitol ester and polyoxyethylene sorbitan ester; microcrystalline cellulose, aluminum metahydroxide, bentonite, etc. may be applied.

[0073] According to one embodiment, when the formulation of the cosmetic composition is a cleansing agent containing a surfactant, it may include a carrier component such as an aliphatic alcohol sulfate, an aliphatic alcohol ether sulfate, a sulfosuccinic acid monoester, an isethionate, an imidazolinium derivative, sodium methyl cocoyl taurate, sodium lauroyl 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, an ethoxylated glycerol fatty acid ester, and the like.

[0074]

[0075] According to another embodiment of the invention, the use of 3-hydroxypropionic acid or a derivative thereof for the manufacture of an antioxidant cosmetic is provided.

[0076] Preferably, the use of 3-hydroxypropionic acid or a derivative thereof for the preparation of the above-described antioxidant cosmetic composition is provided.

[0077] 3-Hydroxypropionic acid has DPPH radical scavenging activity, so a cosmetic composition containing 3-hydroxypropionic acid or a derivative thereof as an active ingredient can be used for antioxidant purposes.

[0078] In the above use, the active ingredient 3-hydroxypropionic acid or a derivative thereof can be used in an amount of 0.5 wt% to 80 wt% based on the total weight of the cosmetic composition.

[0079] In order to sufficiently achieve the antioxidant effect by the action of the above-mentioned effective ingredient, the above-mentioned effective ingredient is preferably used in an amount of 0.5 wt% or more or 1 wt% or more based on the total weight of the cosmetic composition. However, if the above-mentioned effective ingredient is used in an excessive amount, the antioxidant effect may be reduced or side effects may occur. Therefore, the above-mentioned effective ingredient is preferably used in an amount of 80 wt% or less, or 75 wt% or less, or 70 wt% or less based on the total weight of the cosmetic composition. Preferably, the above-mentioned effective ingredient may be used in an amount of 0.5 wt% to 80 wt%, or 0.5 wt% to 75 wt%, or 1 wt% to 75 wt%, or 1 wt% to 70 wt% based on the total weight of the cosmetic composition.

[0080]

[0081] According to another embodiment of the invention, a method for protecting skin from oxidative stress is provided using a cosmetic composition comprising 3-hydroxypropionic acid or a derivative thereof as an active ingredient. Specifically, a method for scavenging 2,2-diphenyl-1-picrylhydrazyl radicals is provided using a cosmetic composition comprising 3-hydroxypropionic acid or a derivative thereof as an active ingredient.

[0082] Preferably, the method for protecting the skin from oxidative stress can be performed using the aforementioned antioxidant cosmetic composition. The method can be performed by applying the cosmetic composition to a body part requiring antioxidant protection. The method can be performed at a frequency of application of one to several times per day (e.g., one to five times or one to three times), once to seven days per week, for one to six months.

[0083]

[0084] According to another embodiment of the invention, an antioxidant pharmaceutical composition comprising 3-hydroxypropionic acid or a derivative thereof as an active ingredient is provided.

[0085] As a result of the inventors' continued research, it was confirmed that 3-hydroxypropionic acid can exhibit excellent antioxidant effects, such as preventing or treating symptoms caused by active oxygen.

[0086] In particular, 3-hydroxypropionic acid has 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity, and thus a pharmaceutical composition containing 3-hydroxypropionic acid or a derivative thereof as an active ingredient can exhibit excellent antioxidant effects.

[0087] The above-mentioned antioxidant pharmaceutical composition comprises 3-hydroxypropionic acid or a derivative thereof as an active ingredient. Preferably, the above-mentioned antioxidant pharmaceutical composition comprises 3-hydroxypropionic acid as an active ingredient.

[0088]

[0089] 3-Hydroxypropionic acid can be applied as an active ingredient by being synthesized by chemical or biological methods.

[0090] According to one embodiment, 3-hydroxypropionic acid obtained through a biological process such as fermentation of a strain having 3-hydroxypropionic acid production ability may be preferably used as the effective ingredient. 3-hydroxypropionic acid obtained by the above method is radioactive carbon isotope ( 14 C) may be included.

[0091] Preferably, the active ingredient may have a radioactive carbon isotope content of 20 pMC (percent modern carbon) or more as measured by ASTM D6866-21, and a biocarbon content of 20 wt% or more. Specifically, the active ingredient may have a radioactive carbon isotope content of 20 pMC or more as measured by ASTM D6866-21, or 50 pMC or more, or 90 pMC or more, or 100 pMC or more, or 90 to 110 pMC; and a biocarbon content of 20 wt% or more, or 50 wt% or more, or 80 wt% or more, or 90 wt% or more, or 95 wt% or more, or 90 to 100 wt%.

[0092]

[0093] The above-mentioned antioxidant pharmaceutical composition can exhibit DPPH radical scavenging activity due to the action of the above-mentioned active ingredient. The DPPH radical exhibits a deep purple color. The DPPH radical is reduced by the antioxidant active ingredient, thereby discoloring the deep purple color. Using this characteristic, the performance of the antioxidant active ingredient can be measured.

[0094]

[0095] According to one embodiment, the pharmaceutical composition may comprise 0.5 wt% to 80 wt% of the active ingredient based on the total weight of the pharmaceutical composition.

[0096] Specifically, the pharmaceutical composition may contain the active ingredient in an amount of 0.5 wt% or more, or 1 wt% or more, and 80 wt% or less, or 75 wt% or less, or 70 wt% or less, based on the total weight of the pharmaceutical composition.

[0097] In order to ensure that the antioxidant effect can be sufficiently achieved by the action of the above-mentioned effective ingredient, it is preferable that the above-mentioned pharmaceutical composition contains 0.5 wt% or more or 1 wt% or more of the above-mentioned effective ingredient.

[0098] However, if the above-mentioned effective ingredient is included in excessive amounts, the antioxidant effect may be reduced or side effects may occur. Therefore, it is preferable that the above-mentioned pharmaceutical composition contain no more than 80% by weight, no more than 75% by weight, or no more than 70% by weight of the above-mentioned effective ingredient.

[0099] Preferably, the pharmaceutical composition may contain the active ingredient in an amount of 0.5 wt% to 80 wt%, or 0.5 wt% to 75 wt%, or 1 wt% to 75 wt%, or 1 wt% to 70 wt%, based on the total weight of the pharmaceutical composition.

[0100]

[0101] The pharmaceutical composition may further comprise a pharmaceutically acceptable carrier.

[0102] Any carrier commonly used in the formulation of pharmaceutical compositions may be used without particular limitation. For example, the carrier may be sucrose, sorbitol, mannitol, lactose, dextrose, starch, gum acacia, calcium phosphate, alginate, gelatin, calcium silicate, microcrystalline cellulose, polyvinylpyrrolidone, cellulose, water, syrup, methyl cellulose, propyl 4-hydroxybenzoate, talc, magnesium stearate, mineral oil, etc. Pharmaceutically acceptable carriers and formulations are described in detail in Remington's The Science and Practice of Pharmacy (23rd Edition, 2020).

[0103]

[0104] The above pharmaceutical composition may be administered orally or parenterally. When administered parenterally, methods such as skin application, subcutaneous injection, intravenous injection, intramuscular injection, intraperitoneal injection, and transdermal administration may be used.

[0105] The appropriate dosage of the above pharmaceutical composition can be determined by comprehensively considering factors such as the patient's age, weight, sex, formulation method, administration method, administration time, etc.

[0106] The pharmaceutical composition may be formulated using a pharmaceutically acceptable carrier and / or excipient. The formulation of the pharmaceutical composition may be a solution, suspension, emulsion, ointment, powder, granule, tablet, or capsule in an aqueous medium or oil.

[0107]

[0108] According to another embodiment of the invention, there is provided the use of 3-hydroxypropionic acid or a derivative thereof for the manufacture of an antioxidant agent.

[0109] Preferably, the use of 3-hydroxypropionic acid or a derivative thereof for the preparation of the above-described antioxidant pharmaceutical composition is provided.

[0110] 3-Hydroxypropionic acid has DPPH radical scavenging activity, so a pharmaceutical composition containing 3-hydroxypropionic acid or a derivative thereof as an active ingredient can be used for antioxidant purposes.

[0111] In the above use, the active ingredient, 3-hydroxypropionic acid or a derivative thereof, can be used in an amount of 0.5 wt% to 80 wt% based on the total weight of the pharmaceutical composition.

[0112] In order to sufficiently achieve the antioxidant effect by the action of the above-mentioned active ingredient, the above-mentioned active ingredient is preferably used in an amount of 0.5 wt% or more or 1 wt% or more based on the total weight of the pharmaceutical composition. However, if the above-mentioned active ingredient is used in an excessive amount, the antioxidant effect may be reduced or side effects may occur. Therefore, the above-mentioned active ingredient is preferably used in an amount of 80 wt% or less, or 75 wt% or less, or 70 wt% or less based on the total weight of the pharmaceutical composition. Preferably, the above-mentioned active ingredient may be used in an amount of 0.5 wt% to 80 wt%, or 0.5 wt% to 75 wt%, or 1 wt% to 75 wt%, or 1 wt% to 70 wt% based on the total weight of the pharmaceutical composition.

[0113]

[0114] According to another embodiment of the invention, a method for protecting the body from oxidative stress is provided using a pharmaceutical composition comprising 3-hydroxypropionic acid or a derivative thereof as an active ingredient. Specifically, a method for scavenging 2,2-diphenyl-1-picrylhydrazyl radicals is provided using a pharmaceutical composition comprising 3-hydroxypropionic acid or a derivative thereof as an active ingredient.

[0115] Preferably, the method for protecting the body from the above-described oxidative stress can be performed using the above-described antioxidant pharmaceutical composition. The method can be performed orally or parenterally. The method can be performed for 1 to 6 months, 1 to 7 days a week, 1 to several times a day (e.g., 1 to 5 times or 1 to 3 times). The method can be performed according to conventional procedures, comprehensively considering factors such as the patient's age, weight, sex, formulation of 3-hydroxypropionic acid or a derivative thereof, administration method, administration time, etc.

[0116]

[0117] According to the present invention, a cosmetic composition and a pharmaceutical composition are provided that have 2,2-diphenyl-1-picrylhydrazyl radical scavenging ability and can exhibit an excellent antioxidant effect.

[0118]

[0119] Figure 1 is an image showing the results of a skin tissue cell stability experiment according to Experimental Example 2.

[0120]

[0121] The following specific examples of the invention will illustrate its functions and effects in greater detail. However, these examples are provided solely to aid understanding of the invention. The following examples are not intended to limit the scope of the invention in any way, and it will be apparent to those skilled in the art that various modifications and variations are possible within the scope and spirit of the invention.

[0122]

[0123] Manufacturing Example 1

[0124] A recombinant vector was constructed by introducing genes encoding glycerol dehydratase and aldehyde dehydrogenase, which are known to produce 3-hydroxypropionic acid using glycerol as a substrate. The recombinant vector was introduced into the E. coli W3110 strain to construct a strain for producing 3-hydroxypropionic acid.

[0125] Specifically, the BtuR gene encoding adenosyltransferase was cloned into the plasmid pCDF, which contains the gene encoding glycerol dehydratase (dhaB), the gene encoding aldehyde dehydrogenase (aldH), and the gene encoding glycerol dehydratase reactivase (gdrAB), to obtain the pCDF_J23101_dhaB_gdrAB_J23100_aldH_btuR vector. The vector was introduced into the W3110 strain (KCCM 40219) by electroporation using an electroporation device (Bio-Rad, Gene Pulser Xcell), to construct a strain for producing 3-hydroxypropionic acid.

[0126] The above 3-hydroxypropionic acid producing strain was fermented at 35°C in a 5 L fermenter using unpurified glycerol as a carbon source to produce 3-hydroxypropionic acid. To prevent a decrease in pH due to the production of 3-hydroxypropionic acid, calcium hydroxide (Ca(OH)2), an alkali metal salt, was added to maintain the pH at neutral during fermentation.

[0127] After fermentation culture, cells were removed by centrifugation (4000 rpm, 10 min, 4 ℃), and primary purification was performed using activated carbon. The concentration of 3-hydroxypropionic acid in the fermented liquid after the primary purification was 50 to 100 g / L, and it was concentrated to 600 g / L using a rotary evaporator (50 ℃, 50 mbar), and stirred at room temperature (300 rpm) to produce Ca(3HP)2 crystals.

[0128] The crystals were washed three times with ethanol and dried in an oven at 50°C to finally recover them. The weight of the crystals was measured, and the crystals were dissolved in water to obtain 3-hydroxypropionic acid (3HP) using high-performance liquid chromatography (HPLC).

[0129]

[0130] Manufacturing Example 2

[0131] 3-Hydroxypropionic acid (3HP) was obtained in substantially the same manner as in Preparation Example 1, except that Mg(OH)2 was used instead of Ca(OH)2 as the alkali metal salt.

[0132]

[0133] Example 1

[0134] A lotion was prepared by mixing 1 wt% of 3-hydroxypropionic acid obtained in the above manufacturing example 1, 0.5 wt% of hydroxyethyl cellulose, 2 wt% of cetostearyl alcohol, 2 wt% of stearyl triethyl ammonium chloride, and the remaining amount of purified water (total 100 wt%).

[0135]

[0136] Example 2

[0137] A lotion was prepared by mixing 5 wt% of 3-hydroxypropionic acid obtained in the above manufacturing example 1, 0.5 wt% of hydroxyethyl cellulose, 2 wt% of cetostearyl alcohol, 2 wt% of stearyl triethyl ammonium chloride, and the remaining amount of purified water (total 100 wt%).

[0138]

[0139] Example 3

[0140] A toner emulsion was prepared by mixing 1 wt% of 3-hydroxypropionic acid obtained in the above manufacturing example 1, 55 wt% of ethanol, 3 wt% of glycerin, 5 wt% of castor oil, and the remaining amount of purified water (total 100 wt%).

[0141]

[0142] Example 4

[0143] A toner emulsion was prepared by mixing 5 wt% of 3-hydroxypropionic acid obtained in the above manufacturing example 1, 55 wt% of ethanol, 3 wt% of glycerin, 5 wt% of castor oil, and the remaining amount of purified water (total 100 wt%).

[0144]

[0145] Example 5

[0146] A toner emulsion was prepared by mixing 10 wt% of 3-hydroxypropionic acid obtained in the above manufacturing example 1, 55 wt% of ethanol, 3 wt% of glycerin, 5 wt% of castor oil, and the remaining amount of purified water (total 100 wt%).

[0147]

[0148] Example 6

[0149] A pharmaceutical composition in the form of an ointment was prepared by mixing 1 wt% of 3-hydroxypropionic acid obtained in the above manufacturing example 1, 0.5 wt% of hydroxyethyl cellulose, 2 wt% of cetostearyl alcohol, 2 wt% of stearyl triethyl ammonium chloride, and the remainder of purified water (total 100 wt%).

[0150]

[0151] Example 7

[0152] A pharmaceutical composition in the form of an ointment was prepared by mixing 5 wt% of 3-hydroxypropionic acid obtained in the above manufacturing example 1, 0.5 wt% of hydroxyethyl cellulose, 2 wt% of cetostearyl alcohol, 2 wt% of stearyl triethyl ammonium chloride, and the remainder of purified water (total 100 wt%).

[0153]

[0154] Example 8

[0155] A pharmaceutical composition in the form of an emulsion was prepared by mixing 1 wt% of 3-hydroxypropionic acid obtained in the above manufacturing example 1, 55 wt% of ethanol, 3 wt% of glycerin, 5 wt% of castor oil, and the remaining amount of purified water (total 100 wt%).

[0156]

[0157] Example 9

[0158] A pharmaceutical composition in the form of an emulsion was prepared by mixing 5 wt% of 3-hydroxypropionic acid obtained in the above manufacturing example 1, 55 wt% of ethanol, 3 wt% of glycerin, 5 wt% of castor oil, and the remaining amount of purified water (total 100 wt%).

[0159]

[0160] Example 10

[0161] A pharmaceutical composition in the form of an emulsion was prepared by mixing 10 wt% of 3-hydroxypropionic acid obtained in the above manufacturing example 1, 55 wt% of ethanol, 3 wt% of glycerin, 5 wt% of castor oil, and the remaining amount of purified water (total 100 wt%).

[0162]

[0163] Experimental Example 1

[0164] (Measurement of radiocarbon isotope and biocarbon content)

[0165] The radiocarbon isotope content (pMC) and biocarbon content of 3-hydroxypropionic acid obtained in Manufacturing Examples 1 and 2 were measured using ASTM D6866-21 (Method B).

[0166] The above biocarbon content refers to the content of biocarbon contained in the 3-hydroxypropionate crystals obtained in the above manufacturing examples 1 and 2, and the radiocarbon isotope ratio (pMC) refers to the radiocarbon isotope contained in the 3-hydroxypropionate crystals ( 14 C) and radiocarbon isotopes of modern reference materials ( 14 C) refers to the ratio.

[0167]

[0168] Concentration (g / L) Radiocarbon isotope ratio (pMC) Biocarbon content (wt%) Manufacturing example 1600 101.52 100 Manufacturing example 2800 102.23 100

[0169] Referring to Table 1 above, it was confirmed that both the 3HP salt crystals of Manufacturing Examples 1 and 2 had a radioactive carbon isotope ratio of 101 pMC or more and a biocarbon content of 100 wt%.

[0170]

[0171] Experimental Example 2

[0172] (Skin tissue cell stability experiment)

[0173] 1) Explant tissue culture

[0174] Human skin tissues provided for research purposes (IRB No. 4-2023-0054; Yonsei University College of Medicine, Severance Medical Center Institutional Review Board) were free of fat and washed several times with PBS (phosphate-buffered saline; Lonza) to remove residual impurities. 1 cm × 1 cm was prepared for each test group, and the test composition was applied to the prepared skin tissues, while PBS was applied to the negative control group. The skin tissues, after absorption of the test composition, were cultured in a dedicated medium at 37°C and 5% CO2.

[0175] 2) HE (Hematoxylin eosin) staining

[0176] Tissues obtained 24 hours after application of the test composition were fixed with 10% formalin, and paraffin blocks and paraffin-embedded slides were prepared. The deparaffinized tissues were stained for nuclei with hematoxylin (S3309; dako) solution and then washed in running water. The cytoplasm was stained with eosin (318906; sigma) solution, followed by a washing process. The tissues were completely dehydrated and fixed using a mounting solution. The epidermis and papillary dermis of the fixed tissues were photographed at 400x using an optical microscope (BX43F; OLYMPUS).

[0177] Referring to Figure 1, it was confirmed that no damage to the epidermis and dermis or separation between tissues was observed in skin tissues to which 3HP was applied at concentrations of 1%, 5%, and 10%.

[0178]

[0179] Experimental Example 3 (Control Group)

[0180] The 3HP aqueous solution obtained in the above Manufacturing Example 1 was prepared in five concentrations (0 wt%, 1 wt%, 5 wt%, 10 wt%, 70 wt%), and 50 μl of each 3HP aqueous solution and 150 μl of methanol were dispensed into a 96-well plate and reacted at room temperature for 30 minutes. The absorbance (OD) for this 대조군 , wavelength 520 nm) was measured three times.

[0181]

[0182] Experimental Example 4 (negative control)

[0183] A DPPH aqueous solution containing 0.5 mM DPPH (free radical, 95%, Alfa Aesar) was prepared. 50 μl of methanol and 150 μl of the DPPH aqueous solution were dispensed into a 96-well plate and reacted at room temperature for 30 minutes. The absorbance (OD 음성대조군, wavelength 520 nm) was measured three times.

[0184]

[0185] Experimental Example 5 (Experimental Group)

[0186] A DPPH aqueous solution containing 0.5 mM DPPH (free radical, 95%, Alfa Aesar) was prepared. The 3HP aqueous solution obtained in the above Preparation Example 1 was prepared in five concentrations (0 wt%, 1 wt%, 5 wt%, 10 wt%, 70 wt%), and 50 μl of each 3HP aqueous solution and 150 μl of the DPPH aqueous solution were dispensed into a 96-well plate and reacted at room temperature for 30 minutes. The absorbance (OD) for this 실험군 , wavelength 520 nm) was measured three times.

[0187]

[0188] Absorbance at a wavelength of 520 nm was measured using a microreader.

[0189] The DPPH radical scavenging activity (antioxidant power) of 3HP was calculated according to Equation 1 below, and the results are shown in the tables below.

[0190] [Formula 1]

[0191] Antioxidant power (%) = {[(OD 음성대조군 - OD 대조군 ) - (OD 실험군 - OD 대조군 ) ] / (OD 음성대조군 - OD 대조군 )} X 100

[0192]

[0193] OD 대조군 3HP Treatment Concentration 1 time 2 times 3 times Average Standard Deviation 0 % 0.039 0.039 0.039 0.039 0.039 0.0001 % 0.039 0.039 0.039 0.039 0.0005 % 0.041 0.042 0.043 0.042 0.00110 % 0.040 0.040 0.040 0.040 0.040 0.00070 % 0.037 0.036 0.037 0.037 0.000

[0194] OD 실험군 3HP Treatment Concentration 1 time 2 times 3 times Average Standard Deviation 0 % 0.616 0.614 0.613 0.614 0.0011 % 0.610 0.609 0.608 0.609 0.0015 % 0.602 0.600 0.599 0.600 0.00110 % 0.586 0.585 0.584 0.585 0.00170 % 0.495 0.492 0.492 0.493 0.002

[0195] OD 음성대조군 3HP treatment concentration 1 time 2 times 3 times average standard deviation 0 % 0.6160.6140.6130.6140.001

[0196] Antioxidant power (%) 3HP Treatment concentration 1 time 2 times 3 times Mean standard deviation 3HP 0% Significance probability (p-value) 0 % 0.0000.0000.0000.0000.000-1 % 0.8501.0420.8190.9040.1210.0065 % 2.4522.5522.4192.4740.0690.00010 % 5.2095.2055.1115.1750.0560.00070 % 20.88821.14221.00221.0110.1270.000

[0197] Referring to the above experimental results, it was confirmed that significant DPPH radical scavenging activity was exhibited under the treatment concentration of the above 3-hydroxypropionic acid.

[0198]

[0199] Formulation Example 1

[0200] A flexible toner (skin lotion) is prepared by mixing 0.2 wt% of 3-hydroxypropionic acid according to the above Preparation Example 1, 3.0 wt% of glycerin, 2.0 wt% of butylene glycol, 2.0 wt% of propylene glycol, 0.1 wt% of polyacrylic acid, 0.2 wt% of polyethylene glycol-12 nonylphenyl ether, 0.4 wt% of polysorbate-80, 10.0 wt% of ethanol, 0.1 wt% of triethanolamine, and the remainder of purified water.

[0201]

[0202] Formulation Example 2

[0203] A nourishing toner (milk lotion) is prepared by mixing 1.0 wt% of 3-hydroxypropionic acid according to the above Preparation Example 1, 3.0 wt% of glycerin, 3.0 wt% of butylene glycol, 0.5 wt% of liquid paraffin, 4.0 wt% of beeswax, 5.0 wt% of caprylic / capric triglyceride, 5.0 wt% of squalene, 1.5 wt% of polysorbate-60, 1.0 wt% of cetearyl alcohol, 1.5 wt% of sorbitan sesquioleate, 0.1 wt% of polyacrylic acid, 0.2 wt% of triethanol amine, and the remainder of purified water.

[0204]

[0205] Formulation Example 3

[0206] A nourishing cream is prepared by mixing 2.0 wt% of 3-hydroxypropionic acid according to Preparation Example 1, 3.0 wt% of glycerin, 3.0 wt% of butylene glycol, 7.0 wt% of liquid paraffin, 7.0 wt% of beta-glucan, 3.0 wt% of caprylic / capric triglyceride, 5.0 wt% of squalene, 1.5 wt% of cetearyl glucoside, 1.2 wt% of polysorbate-60, 0.4 wt% of sorbitan stearate, 0.1 wt% of polyacrylic acid, 0.1 wt% of triethanolamine, and the remainder of purified water.

[0207]

[0208] Formulation Example 4

[0209] 8 mg of 3-hydroxypropionic acid, 9 mg of vitamin C, 9 mg of vitamin E, 200 mg of lactose, and 200 mg of galactooligosaccharide according to the above Manufacturing Example 1 are mixed, granulated using a fluidized bed dryer, and 5 mg of sugar ester is added to prepare a tablet composition. 500 mg of the above tablet composition is pressed into tablets to prepare tablets.

[0210]

[0211] Formulation Example 5

[0212] A soft capsule filling liquid is prepared by mixing 8 mg of 3-hydroxypropionic acid, 9 mg of vitamin C, 9 mg of vitamin E, 10 mg of hydrogenated vegetable oil, and 9 mg of lecithin according to the above Manufacturing Example 1. Separately, a soft capsule sheet is prepared by mixing 65 wt% of gelatin, 25 wt% of glycerin, and 10 wt% of sorbitol solution. 400 mg of the above soft capsule filling liquid is filled into each capsule to prepare a soft capsule.

[0213]

[0214] Formulation Example 6

[0215] 8 mg of 3-hydroxypropionic acid, 9 mg of vitamin C, 9 mg of vitamin E, 500 mg of starch, and 200 mg of anhydrous crystalline glucose according to the above manufacturing example 1 are mixed, formed into granules using a fluidized bed granulator, and then filled into a bag to manufacture a granule preparation.

[0216]

[0217] Formulation Example 7

[0218] A drink composition is prepared by mixing 8 mg of 3-hydroxypropionic acid, 9 mg of vitamin C, 9 mg of vitamin E, 0.7 g of citric acid, 10 g of glucose, and 25 g of liquid oligosaccharide according to the above manufacturing example 1, and then adding 300 ml of purified water. 200 ml of the drink composition is filled into bottles and sterilized at 130°C for about 5 seconds to prepare a drink.

[0219]

[0220] Formulation Example 8

[0221] An injection is prepared by mixing 30 mg of 3-hydroxypropionic acid according to Manufacturing Example 1, an appropriate amount of sterile distilled water for injection, and an appropriate amount of a pH regulator.

[0222]

[0223] Although the present invention has been described above through limited embodiments, the present invention is not limited thereto, and it is obvious that various modifications and variations are possible within the scope of the technical idea of ​​the present invention and the equivalent scope of the patent claims to be described below by a person having ordinary skill in the art to which the present invention pertains.

Claims

An antioxidant cosmetic composition comprising 1.3-hydroxypropionic acid or a derivative thereof as an active ingredient.

2. In paragraph 1, The above cosmetic composition is an antioxidant cosmetic composition having 2,2-diphenyl-1-picrylhydrazyl radical scavenging ability.

3. In paragraph 1, An antioxidant cosmetic composition comprising 0.5 wt% to 80 wt% of the effective ingredient based on the total weight of the composition.

4. In paragraph 1, An antioxidant cosmetic composition wherein the above effective ingredient has a radioactive carbon isotope content of 20 pMC (percent modern carbon) or more as measured according to ASTM D6866-21 and a biocarbon content of 20 wt% or more.

5. In paragraph 1, An antioxidant cosmetic composition, wherein the cosmetic composition further comprises a physiologically acceptable medium.

6. In paragraph 1, The cosmetic composition has an antioxidant formulation that is a solution, suspension, emulsion, paste, gel, cream, lotion, powder, oil, foam, pack, spray, aerosol, balm, solid soap, liquid soap, powder foundation, emulsion foundation, or wax foundation. A pharmaceutical composition for antioxidant action, comprising 7.3-hydroxypropionic acid or a derivative thereof as an active ingredient.

8. In paragraph 7, The above pharmaceutical composition is an antioxidant pharmaceutical composition having 2,2-diphenyl-1-picrylhydrazyl radical scavenging activity.

9. In paragraph 7, An antioxidant pharmaceutical composition comprising 0.5 wt% to 80 wt% of the active ingredient based on the total weight of the composition.

10. In paragraph 7, The above-mentioned effective ingredient is an antioxidant pharmaceutical composition having a radioactive carbon isotope content of 20 pMC (percent modern carbon) or more as measured according to ASTM D6866-21 standard and a biocarbon content of 20 wt% or more.

11. In paragraph 7, An antioxidant pharmaceutical composition, wherein the pharmaceutical composition further comprises a pharmaceutically acceptable carrier.

12. In paragraph 7, The above pharmaceutical composition is an antioxidant pharmaceutical composition for oral or parenteral use.

13. Use of 3-hydroxypropionic acid or a derivative thereof for the manufacture of antioxidant cosmetics or antioxidant drugs. A method for protecting the body from oxidative stress using a cosmetic composition or pharmaceutical composition containing 14.3-hydroxypropionic acid or a derivative thereof as an active ingredient.

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