KR100483113B1 - Kojyl Benzoate derivatives and Preparation method thereof, and cosmetic composition containing thereof - Google Patents

Abstract

The present invention relates to a co-benzoic acid derivative represented by the following formula (1) or (2), a preparation method thereof, and a cosmetic composition containing the same. The co-benzoic acid derivative may be obtained by reacting benzoic acid and kojic acid in an organic solvent in an equivalent ratio of 1: 1 to 1: 2.

(In the _{formula, R 1, R 2, R} 3, R 4, R 5 are each _{H, OH, C 1 ~ C} 8 alkyl group, C ₁ ~ C ₈ alkoxy group or NX ₂ (X = H or C Alkyl group of ₁ to C ₈ , except that R ₁ , R ₂ , R ₃ , R ₄ , and R ₅ are all H.)

(In the formula, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ is H, OH, C ₁ ~ C ₈ alkyl group, C ₁ ~ C ₈ alkoxy group or NX ₂ (X = H or C ₁ Alkyl group of C ₈ , except that R ₁ , R ₂ , R ₃ , R ₄ and R ₅ consist of H; and one or two OH;

Description

Kojyl-benzoic acid derivatives and preparation methods thereof, and cosmetic compositions containing the same

The present invention relates to a co-benzoic acid derivative represented by the following formula (1) or (2), a preparation method thereof, and a cosmetic composition containing the same.

[Formula 1]

(In the _{formula, R 1, R 2, R} 3, R 4, R 5 are each _{H, OH, C 1 ~ C} 8 alkyl group, C ₁ ~ C ₈ alkoxy group or NX ₂ (X = H or C Alkyl group of ₁ to C ₈ , except that R ₁ , R ₂ , R ₃ , R ₄ , and R ₅ are all H.)

[Formula 2]

(In the formula, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ is H, OH, C ₁ ~ C ₈ alkyl group, C ₁ ~ C ₈ alkoxy group or NX ₂ (X = H or C ₁ Alkyl group of C ₈ , except that R ₁ , R ₂ , R ₃ , R ₄ and R ₅ consist of H; and one or two OH;

Skin aging is closely related to the increase in wrinkles, sagging and relaxation, and environmental factors such as physiological natural aging and UV exposure are mentioned as the cause of this phenomenon. In particular, most of the causes of skin aging associated with cosmetics can be said to be a continuous exposure to ultraviolet light. This causes deep wrinkles, sagging skin, and uneven spots that spoil the appearance.

Histologically, the epidermis becomes thinner, the thickness of the dermis decreases, and the elastin, a major component of the elastic fibers present in the skin, is severely deformed to accumulate "Elastotic" substances that form macromolecules in the upper and middle layers of the dermis. This inhibits the normal function of elastic fibers, leading to loss of collagen due to the activity of matrix metalloproteinases (MMPs) and wrinkled skin types that lack elasticity. Many cosmetic researches have been conducted to inhibit or delay such skin aging. Typically, a skin moisturizer reduces the dryness of the skin or a sunscreen that damages the skin. There is a way to reduce penetration. In addition, there is a method of using an antioxidant capable of scavenging free radicals, which is a major mediator for skin aging, or a metabolic promoter that stimulates the skin or activates skin cells.

In particular, a study is being conducted to prevent various skin-related aging causes resulting from hormone reduction by paying attention to the effects of hormone reduction such as estrogen, which is one of the most important physiological phenomena, with age, on skin aging. have. In particular, studies on the effects of estrogen on skin aging are being actively conducted, and it has been reported to directly affect many indices related to skin aging. It has also been confirmed that estrogen receptors are also present in the skin (epidermis and dermis) and have been reported to be found in skin structures associated with skin aging. Symptoms of skin aging experienced by postmenopausal women include changes in collagenous and elastic fibers due to estrogen deficiency. Estrogens promote the synthesis and growth of collagen, increase the synthesis of hyaluronic acid, and increase water retention ( Maturitas, 39, 43-55, 2001).

As a result, estrogens improve most of the indicators associated with skin aging, such as epidermal skin moisture, elasticity, skin thickness, and skin surface lipids. In order to achieve this effect, a lot of plant extracts that can produce a hormone replacement effect have been used, and there are representative flavonoids of natural origin known as phytoestrogens. However, since these plant extracts are always obtained in a mixture with other ingredients, they are not high in activity, and in addition to the desired efficacy, various side effects may be caused by other mixtures, and it is also difficult to establish an accurate mechanism of action. . Many synthetics have been developed using organic chemical methods to solve this problem of extracts ( Chemistry & Biology , 6 (4), 205-219, 1999). none.

Because kojic acid has a strong inhibitory effect on tyrosinase, an important enzyme of skin pigmentation, it has been mainly used for the purpose of showing whitening effect, and many stable derivatives have been developed due to the instability of the substance. Rarely, the anti-aging effect of the lipid oxidation inhibition of kojic acid was reported, but the effect was very small. The inventors have noticed that although one of the two hydroxy groups of kojic acid having excellent physiological activity is used to make a substituent, one remaining hydroxy group can be used to make hydrogen bonds important in the association with various enzymes. Through derivatization, we tried to develop a safe ligand material that can best bind to the estrogen receptor. In order to achieve the above object, it has been found that a benzoic acid compound having a hydroxyl group, an amino group, an alkoxy, or an alkyl group capable of hydrogen bonding with various substituents, in particular, an estrogen receptor and having a peroxidation inhibiting ability through radical scavenging ability, is suitable. Through the esterification of the co-benzoic acid derivatives were developed.

In addition, the inventors of the present invention have been patented by inventing kojic acid-derivative, which has less side effects to the human body than the conventional kojic acid and its derivatives, strongly inhibits the activity of tyrosinase, and has excellent skin anti-aging effect. Patent 111689). However, the above materials are not stable due to the position 5 of kojic acid and the hydroxyl groups present at benzoic acid. In order to overcome this, it was found that the presence of other substituents besides hydroxyl groups in benzoic acid not only improves stability but also shows good results in efficacy. This seems to be because the effect on aging is not only dependent on the radical scavenging ability but also due to the binding capacity of the estrogen receptor, which is the core of the present invention.

The present inventors have completed the present invention by focusing on the above points.

Accordingly, it is an object of the present invention to provide a co-benzoic acid derivative represented by the following formula (1) or (2).

[Formula 1]

(In the _{formula, R 1, R 2, R} 3, R 4, R 5 are each _{H, OH, C 1 ~ C} 8 alkyl group, C ₁ ~ C ₈ alkoxy group or NX ₂ (X = H or C Alkyl group of ₁ to C ₈ , except that R ₁ , R ₂ , R ₃ , R ₄ , and R ₅ are all H.)

[Formula 2]

(In the formula, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ is H, OH, C ₁ ~ C ₈ alkyl group, C ₁ ~ C ₈ alkoxy group or NX ₂ (X = H or C ₁ Alkyl group of C ₈ , except that R ₁ , R ₂ , R ₃ , R ₄ and R ₅ consist of H; and one or two OH;

Furthermore, another object of the present invention is to provide a method for producing the above-mentioned co-benzoic acid derivative.

The above object can be achieved by reacting benzoic acid with thionyl chloride in the presence of an organic solvent to form benzoyl chloride and then reacting with kojic acid in the presence of an organic base.

Still another object of the present invention is to provide a cosmetic composition containing a co-benzoic acid derivative.

The present invention provides a novel coryl-benzoic acid derivative compound represented by the following general formula (1) or (2).

[Formula 1]

(In the _{formula, R 1, R 2, R} 3, R 4, R 5 are each _{H, OH, C 1 ~ C} 8 alkyl group, C ₁ ~ C ₈ alkoxy group or NX ₂ (X = H or C Alkyl group of ₁ to C ₈ , except that R ₁ , R ₂ , R ₃ , R ₄ , and R ₅ are all H.)

[Formula 2]

(In the formula, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ is H, OH, C ₁ ~ C ₈ alkyl group, C ₁ ~ C ₈ alkoxy group or NX ₂ (X = H or C ₁ Alkyl group of C ₈ , except that R ₁ , R ₂ , R ₃ , R ₄ and R ₅ consist of H; and one or two OH;

The co-benzoic acid derivative of Formula 1 or Formula 2 above inhibits the oxidative action by active oxygen that appears in vivo when applied to the skin, inhibits the production of peroxides, and promotes the effect of preventing aging of the biofilm and collagen biosynthesis. As a material having an effect, there is no irritation to the skin, and it can provide an excellent effect on the elasticity of the skin, prevention and improvement of skin aging.

On the other hand, the cosmetic composition of the present invention by increasing the skin elasticity and anti-aging effect by containing the above-mentioned co-benzoic acid derivative in an amount of 0.001 to 20%, preferably 0.05 to 5% by weight based on the total weight of the composition Could confirm.

The cosmetic composition of the present invention is not particularly limited in its formulation, and may have, for example, a formulation such as a flexible lotion, a nourishing lotion, a massage cream or a nourishing cream.

In addition, the co-benzoic acid derivative constituting the cosmetic composition of the present invention can be appropriately selected and blended by those skilled in the art according to the dosage form and the desired effect without difficulty.

The cosyl-benzoic acid derivative represented by Formula 1 or 2 provided in the present invention may preferably be prepared by the following two methods as specific examples below.

As a first example (method A), there is a method in which benzoic acid is reacted with thionyl chloride in the presence of an organic solvent to form benzoyl chloride, and then reacted with kojic acid in the presence of an organic solvent and an organic base to produce a cozyl-benzoic acid derivative. This can be illustrated by Scheme 1 below.

As a second example (method B), there is a method in which benzoic acid is reacted with an inorganic base in alcohol to make a benzoate, and then reacted with cosyl chloride to produce a cosyl-benzoic acid derivative. This can be illustrated by Scheme 2 below.

Referring to the preparation method of the co-benzoic acid derivatives according to the present invention in detail.

Method A: A method of reacting benzoic acid with thionyl chloride in the presence of an organic solvent to form benzoyl chloride, followed by reaction with kojic acid in the presence of an organic solvent and an organic base to produce a cosyl-benzoic acid derivative.

It is preferable to make thionyl chloride react with benzoic acid in the said method by the equivalent ratio of 1: 1: 1. If the equivalence ratio is less than 1: 1, unreacted benzoic acid is obtained in addition to the desired product. If the ratio is 1: 2 or more, the desired product can be obtained. However, an excess of unreacted thionyl chloride is obtained, which is difficult to purify.

In addition, the organic solvent used in the step of producing benzoyl chloride is preferably reacted in an equivalent ratio of 1: 2-5. If it is 1: 2 or less, unreacted benzoic acid is obtained in addition to the desired product, and if it is 1: 5 or more, there will be no problem in reaction but it will have difficulty in purification.

In the above step, the organic base is preferably reacted at an equivalent ratio of 1: 1 to 1.3. If the equivalent ratio is less than 1: 1, unreacted benzoyl chloride is obtained in addition to the desired product. If the ratio is 1: 1.3 or more, the desired product can be obtained. However, an excess of unreacted organic base is obtained, which is difficult to purify. Triethylamine, pyridine and the like may be used for the organic base used at this time, but triethylamine is preferably used.

In the above method, the kojic acid is preferably reacted in an equivalent ratio of 1: 1 to 2. If the equivalence ratio is less than 1: 1, unreacted benzoyl chloride is obtained in addition to the desired product. If the ratio is 1: 2 or more, the desired product can be obtained, but an excess of unreacted kojic acid is obtained, which is difficult to purify.

Dimethylformamide, tetrahydrofuran, dichloromethane and the like can be used as the organic solvent in the method (A) in the production method of the present invention, but tetrahydrofuran is preferably used.

In addition, other reaction conditions, that is, reaction temperature, reaction time can be easily selected and applied by those skilled in the art.

Method B: A method of reacting benzoic acid with an inorganic base in alcohol to form a benzoate and then reacting with cosyl chloride to produce a cosyl-benzoic acid derivative.

In the above method, the inorganic base is preferably reacted in an equivalent ratio of 1: 1 to 1.3. If the equivalence ratio is less than 1: 1, unreacted benzoic acid is obtained in addition to the desired product. If the ratio is 1: 1.3 or more, the desired product can be obtained, but other by-products are obtained and it is difficult to purify.

As the inorganic base, sodium hydroxide, potassium hydroxide, sodium carbonate, magnesium carbonate, magnesium oxide, and the like can be used, but potassium hydroxide is preferably used.

In the above method, it is preferable that the benzoate and the cosyl chloride are reacted at an equivalent ratio of 1: 1 to 1.2. If the equivalent ratio is less than 1: 1, an unreacted benzoate is obtained in addition to the desired product. If the ratio is 1: 1.2 or more, the desired product can be obtained.

Dimethylformamide, tetrahydrofuran, dichloromethane and the like can be used as the organic solvent in the method (B) in the preparation method of the present invention, but dimethylformamide is preferably used.

Other reaction conditions, such as reaction temperature, reaction time, etc., may be appropriate to those skilled in the art to find an appropriate temperature or reaction time during implementation.

Hereinafter, the preparation method of the co-benzoic acid derivative according to the present invention will be described in more detail with reference to the following examples. However, the present invention is not limited to these examples.

[Comparative Example 1] Method for preparing 2- (4-hydroxybenzoyl) oxymethyl-5-hydroxy-4H-pyran-4one (Formula 2, R ₁ , R ₂ , R ₄ , R ₅ = H, R ₃ = OH).

1.39 g (10.1 mmol) of 4-hydroxybenzoic acid and 0.4 g (10.1 mmol) of sodium hydroxide were dissolved in 40 ml of methanol. Methanol was distilled off and the remaining residue was dissolved in 70 ml of dimethylformamide. 1.46 g (9.1 mmol) of cosyl chloride were added and stirred for 2 hours in a 110 ° C. oil bath. The solvent was distilled off and the residue was taken up in 300 ml of ethyl acetate. The ethyl acetate solution was washed with 5% hydrochloric acid and distilled water, dried over magnesium sulfate and activated carbon, and decolorized. The insolubles were filtered off and the filtrate was evaporated under reduced pressure to yield 1.64 g (69%) of the reaction product 2- (4-hydroxybenzoyl) oxymethyl-5-hydroxy-4H-pyran-4one as a solid. ¹ H-NMR (DMSO-d ₆ , δ): 5.19 (s, 2H), 6.51 (s, 1H), 6.8 to 7.85 (m, 4H), 8.08 (s, 1H), 9.25 (s, 1H), 10.27 (s, 1 H).

Example 1 Synthesis of Cozy 2,4-dimethoxybenzoic acid ester (Formula 1, R ₁ , R ₃ = OMe, R ₂ , R ₄ , R ₅ = H).

3 mL of dimethylformamide is dissolved in tetrahydrofuran, and then 1.55 g (13 mmol) of thionyl chloride is slowly added dropwise and stirred for 10 minutes. 1.82 g (10 mmol) of 2,4-dimethoxybenzoic acid was added dropwise thereto to give 2,4-dimethoxybenzoyl chloride. A solution obtained by dissolving 1.42 g (10 mmol) of kojic acid and 1.21 g (12 mmol) of triethylamine in 30 mL of tetrahydrofuran was slowly added dropwise to produce a cosy 2,4-dimethoxybenzoic acid ester. After completion of the reaction by dropwise addition of water, the organic layer is separated, dehydrated with anhydrous magnesium sulfate, and the solvent is removed under reduced pressure. Recrystallization from dichloromethane affords 2.29 g (75%) of pure white solid, cozy 2,4-dimethoxybenzoic acid ester. 1 H NMR (300 MHz, DMSO) δ 3.90 (s, 3H), 3.95 (s, 3H), 4.42 (d, J = 2 Hz, 2H, -CH ₂ O-), 5.88 (t, J = 2 Hz, 1H, OH), 6.52 (s, 1H), 6.72-6.78 (m, 2H), 8.00 (d, J = 7 Hz, 1H), 8.60 (s, 1H)

Example 2 Synthesis of Cozy 2,4-dihydroxybenzoic acid ester (Formula 1, R ₁ , R ₃ = OH, R ₂ , R ₄ , R ₅ = H).

The procedure of this example was the same as that of Example 1, except that 1.54 g (10 mmol) of 2,4-dihydroxybenzoic acid was used instead of 2,4-dimethoxybenzoic acid, and a pure white, pure, cozy 2,4-di 1.53 g (55%) of hydroxybenzoic acid ester were obtained. 1 H NMR (300 MHz, DMSO) δ 5.25 (s, 2H), 6.40 (s, 1H), 6.43 (d, J = 7 Hz, 1H), 6.60 (s, 1H), 7.75 (d, J = 7 Hz , 1H), 8.18 (s, 1H), 9.90 (s, 1H), 10.51 (s, 1H), 10.78 (s, 1H)

Example 3 Synthesis of Cozy 2,4-dimethoxybenzoic acid ester (Formula 2, R ₁ , R ₃ = MeO, R ₂ , R ₄ , R ₅ = H).

1.82 g (10 mmol) of 2,4-dimethoxybenzoic acid was dissolved in 20 mL of ethanol, and 0.56 g (10 mmol) of sodium hydroxide was added dropwise to form a benzoate. The resulting benzoate solid was filtered off and dissolved in 20 mL of dimethylformamide, followed by the dropwise addition of cosyl chloride (11 mmol) to produce cosly 2,4-dimethoxybenzoic acid. Dimethylformamide is distilled off, and water is added dropwise to precipitate a white, cosy 2,4-dimethoxybenzoic acid ester which is then filtered to give 2.11 g (66%). 1 H NMR (300 MHz, DMSO) δ 3.91 (s, 3H), 3.94 (s, 3H), 5.42 (s, 2H, -CH ₂ O-), 6.32 (s, 1H), 6.52-6.60 (m, 2H ), 7.98 (d, J = 7 Hz, 1H), 8.43 (s, 1H)

Example 4 Synthesis of Cozy 4-amino-2-hydroxybenzoic acid ester (Formula 2, R ₁ = OH, R ₃ = NH ₂ , R ₂ , R ₄ , R ₅ = H).

The procedure of this example was the same as that of Example 3, except that 1.53 g (10 mmol) of 4-amino-2-hydroxybenzoic acid was used instead of 2,4-dimethoxybenzoic acid, and a pure yellow 4-amino pure pure amino was obtained. 2.25 g (81%) of 2-hydroxybenzoic acid ester were obtained. 1 H NMR (300 MHz, DMSO) δ 5.21 (s, 2H), 6.08 (s, 1H), 6.12 (d, J = 7 Hz, 1H), 6.35 (s, 1H), 6.58 (d, J = 7 Hz , 1H), 8.18 (s, 1H), 9.35 (s, 1H), 10.55 (s, 1H)

[Test Example 1]

After epilating the back part of the guinea pig, 120 ml of a solution obtained by diluting the compound prepared in Comparative Example and Example to 1% concentration in a solvent (1,3-BG: EtOH = 5: 1) was subjected to patching for 24 hours. An ultraviolet (UVB) of 500 mJ / cm ² was irradiated. The skin is biopsied 18 hours after UV irradiation. The skin was ground and centrifuged to obtain a supernatant and used for the experiment. Quantification of lipid peroxide was carried out by reacting the tissue supernatant with 1% thiobarbituric acid (TBA) and then using a fluorescence spectrophotometer for excitation at a wavelength of 515 nm and emission at 553 nm. Fluorescence was measured at wavelength, and a standard curve was prepared using 1,1,3,3-tetraethoxy propane (TEP) as a standard to compare and quantify lipid peroxide ( Biochem. Med. , 15 , 212-216, 1976). The experimental results are shown in Table 1 below.

matter % Inhibition of lipid peroxide production Control 0 Example 1 30 Example 2 35 Example 3 28 Example 4 37 Comparative Example 1 31

As shown in the above results, the co-benzoic acid derivative has an excellent lipid peroxidation inhibitory effect in vivo, and thus the skin aging prevention effect is excellent.

[Test Example 2]

In the hairless mice, a solution of the compound prepared in Comparative Examples and Examples was diluted to 1% concentration in a solvent (1,3-BG: EtOH = 5: 1) at 100% in the morning and 100 mJ / cm ² in the afternoon. UV irradiation was continued for 10 weeks. The control group was irradiated with ultraviolet light only without applying the example. Each group used 10 animals. Two months later, biopsies were taken, and immunostaining was performed using type 1 pN collagen. This staining method can be used to determine the amount of newly synthesized collagen. Each sample was judged to be 1-5 grade (1 is the highest, 5 is the lowest), and the collagen production rate was calculated ( N Engl. J. Med. , 329, 530-535, 1993, Eur. J. Biochem. , 134, 183-189, 1983). The experimental results are shown in Table 2 below.

matter Collagen production rate (%) Control 15 Example 1 40 Example 2 32 Example 3 38 Example 4 30 Comparative Example 1 29

Estrogen-like substances are known to improve many indicators related to skin aging, such as increased collagen production. From the above results, it can be seen that the co-benzoic acid derivative is an effective substance for preventing skin aging by increasing the production of collagen which decreases with age in vivo.

Experimental Example 3 Stability of the Cozylic-Benzoic Acid Derivative

In the stability test, 3 g each of the co-benzoic acid derivative compound of Example and Comparative Example 1 were weighed, and dissolved in 100 ml of dimethyl sulfoxide. After storage in a 60 ° C. thermostat, the change in residual rate was observed for 6 months.

1 month 2 months 3 months 4 months 5 months 6 months Example 1 100 100 99 99 99 98 Example 2 100 100 98 97 97 96 Example 3 100 99 99 97 96 95 Example 4 100 100 98 96 96 94 Comparative Example 1 95 92 91 86 82 76

As can be seen in Table 3, the anti-aging effect of Comparative Example 1 is similar to the embodiments of the present invention, but the stability is not good due to the hydroxyl groups present in koji acid and benzoic acid. On the other hand, it can be seen that the embodiments of Formula 1 as well as the embodiments of Formula 2 of the present invention are very stable materials.

[Test Example 4] Safety of Cozy 2,4-dimethoxybenzoic acid ester

Since raw materials for cosmetics are used in the human body, safety for the human body is important above all. The present inventors through the following experiment to determine the presence or absence of toxicity and irritation to the human body of the co-benzoic acid derivatives, it was confirmed that the raw material without toxicity and irritation as a cosmetic. Safety experiments were carried out with a solution made of 10% concentration of cosyl 2,4-dimethoxybenzoic acid ester in 1,3-butylene glycol / ethanol (5/1).

4-1) Acute oral toxicity test in mice: Oral administration of 1 mL / kg of the cozyl-benzoic acid derivative to 10 rats of 5 males and females showed no death and no change in body weight before and after administration. No significant difference was observed.

4-2) Acute dermal toxicity test in mice and rabbits: 0.2 mL / kg of the cozyl-benzoic acid derivative is administered once percutaneously to 10 rats of 5 males and 5 females. As a result of the observation, no abnormal symptoms were observed in all groups. No abnormalities were observed in the rabbits in the same manner.

4-3) Primary skin irritation test: The hairs of 12 rabbits were removed 24 hours before application of test substance, and 2.5 mL × 2.5 cm wide with 0.1 mL of the cozyl-benzoic acid derivative for 24 hours. Was applied and observed. Observation determined that there was no stimulus.

4-4) Eye irritation test: Nine rabbits were dosed with saline at 2% concentration of the cosyl-benzoic acid derivative and administered to the eye by 0.1 mL per animal. Experimental results showed no specific eye mucosal irritation to cornea, iris and conjunctiva.

Skin sensitization test: Skin sensitization test was performed by using three coarse-benzoic acid derivatives in each of three male and female guinea pigs according to the test method of Magnusson and Kligman. Skin abnormalities such as skin formation could not be observed.

4-6) Human patch test: Thirty healthy women aged 20 to 28 years were tested according to CTFA Guideline (The Cosmetic Toiletry and Fragrance Association, INC, Washington, D. C. 20036, 1991). As a result, no skin primary irritation response was observed.

4-7) Repeat Insult Human Patch Test: As a result of the CTFA guideline, the human patch test subjects did not show cumulative stimulus response and sensitization response.

In the above toxicity and safety experiments on the skin, it was confirmed that the co-benzoic acid derivative is a safe substance as an external preparation for skin.

The cosmetic composition of the present invention is not particularly limited in its formulation, and may have, for example, a formulation such as a flexible lotion, a nourishing lotion, a massage cream or a nourishing cream. Representative formulations are shown below, but the present invention is not limited to these formulations, and the following formulations can be readily prepared by those skilled in the art.

Formulation Example 1 Cream Formulation

ingredient content (%) Cosyl-benzoic Acid Derivatives 0.1 Liquid paraffin 15.0 Cetostearyl alcohol 3.0 Beeswax 2.0 Methylpolysiloxane 0.5 Lipophilic Monostearic Acid Stearate 2.0 Stearic acid 2.0 Sorbitan Sesquioleate 0.8 Monostearic acid 1.0 Polyoxyethylene sorbitan 1.2 Methylparaben 0.2 Propylparaben 0.1 Spices 0.2 EDTA.2Na 0.02 glycerin 5.0 Propylene glycol 5.0 Triethanolamine 0.2 Imidazolidinylurea 0.3 Purified water to 100

Formulation Example 2-Lotion

ingredient content (%) Cosyl-benzoic Acid Derivatives 0.1 Multi Wax 3.5 Stearic acid 0.5 Liquid paraffin 5.0 Dihidegwax 0.8 Bee wax 17 0.05 Nicole MGS-B 1.9 Arasel 165 0.7 glycerin 7.0 Methylparaben 0.12 Propylparaben 0.03 Liquid paraben 5.0 Twin 60 0.5 Carbomer 0.12 Purified water to 100

As described above, the co-benzoic acid derivative according to the present invention is a safe substance, and is an excellent substance for inhibiting skin aging and UV protection.

Claims (9)

A novel cozyl-benzoic acid derivative compound represented by the following formula (1). [Formula 1] (In the _{formula, R 1, R 2, R} 3, R 4, R 5 are each _{H, OH, C 1 ~ C} 8 alkyl group, C ₁ ~ C ₈ alkoxy group or NX ₂ (X = H or C Alkyl group of ₁ to C ₈ , except that R ₁ , R ₂ , R ₃ , R ₄ , and R ₅ are all H.) delete The benzoic acid derivative represented by the following Chemical Formula 1, characterized in that benzoic acid is reacted with thionyl chloride in the presence of an organic solvent to form benzoyl chloride, and then reacted with kojic acid in the presence of an organic solvent and an organic base to produce a cozylic-benzoic acid derivative. How to prepare. [Formula 1] (In the _{formula, R 1, R 2, R} 3, R 4, R 5 are each _{H, OH, C 1 ~ C} 8 alkyl group, C ₁ ~ C ₈ alkoxy group or NX ₂ (X = H or C Alkyl group of ₁ to C ₈ , except that R ₁ , R ₂ , R ₃ , R ₄ , and R ₅ are all H.) delete The cosmetic composition according to claim 1, wherein the co-benzoic acid derivative of Formula 1 is contained in an amount of 0.001 to 20% by weight based on the total weight of the composition. Cosmetic composition for inhibiting lipid peroxidation, characterized in that containing the compound of formula (1). Cosmetic composition for promoting skin collagen production, characterized in that it contains a compound of the formula (1). Cosmetic composition for inhibiting skin aging, characterized in that containing the compound of formula (1). delete