JP6486590B2 - Anti-aging agent - Google Patents

Description

  The present invention relates to an anti-aging agent, particularly an anti-skin aging agent.

The skin is one organ that plays an important role in maintaining the internal environment of the living body as the forefront that is directly affected by the external environment. For this reason, the function does not stop completely, but the function gradually decreases with age, and signs of aging such as wrinkles, spots, dullness, and tarmi become obvious.
The skin has an antioxidant mechanism as a self-protection mechanism against reactive oxygen species, but when its function decreases with aging, active oxygen exceeding the protective ability becomes a factor that disturbs the internal environment of the skin, and it causes skin aging. Make it progress. In particular, since the skin exposure site is exposed to strong oxidative stress due to ultraviolet irradiation in daily life, the progress of aging becomes remarkable. In aging skin, the amount of water is reduced, the skin becomes inflexible, the collagen, which is the constituent component of the majority of the dermis, is reduced, and the elasticity of the skin is reduced, resulting in wrinkles on the skin surface. And becomes unfavorable in terms of beauty.

  In order to prevent and improve skin aging, the use of various active ingredients (anti-aging ingredients) has been proposed. For example, the use of antioxidants such as vitamin C, vitamin E, superoxide dismutase, and catalase has been proposed (for example, Patent Document 1). Antioxidants having the ability to scavenge free radicals can suppress and stop the radical chain reaction, and therefore can be expected to be effective in preventing skin aging caused by photooxidative stress, such as spots, wrinkles, and tarmi. Moreover, in order to protect the skin where moisture content fell from drying and to make a stratum corneum flexible, it is also generally performed to apply a moisturizing agent continuously. Examples of moisturizers used in cosmetics for such purposes include polyhydric alcohols such as glycerin, 1,3-butylene glycol and dipropylene glycol, and sugar alcohols such as xylitol and erythritol. Furthermore, a substance having an effect of improving wrinkles, for example, a vitamin A derivative (Non-patent Document 1), arjunoleic acid (Patent Document 2), and paritene (Patent Document 3) are used as active ingredients, and a skin external preparation containing these is used. It has been proposed.

  However, the above-mentioned anti-aging ingredient is not always satisfactory in all aspects of safety, stability in the preparation, and action and effect. For example, in a method of continuously applying a moisturizing agent, the moisturizing performance largely depends on the characteristics of individual components such as hygroscopicity and water retention, and in some cases, the expected effect may not be obtained. It was.

  Pentaerythritol is a kind of sugar alcohol, and in the cosmetics field, it has been proposed to have a function as a moisturizer (Non-patent Document 2) and to be blended in a liquid cosmetic (Patent Document 4). It was not known to be an anti-aging active ingredient.

JP-A-8-333260 JP 2005-89311 A JP 7-41419 A Japanese Patent Laid-Open No. 6-48914

Yoshio Hamada, Gen Fukuse, “Vitamin A and its derivatives as an anti-wrinkle material”, Fragrance Journal, Fragrance Journal, published April 15, 1998, Vol. 26, No. 4, pp. 75-77 International Cosmetic Ingredient Dictionary and Handbook Thirteenth Edition 2010

  In view of such a current situation, an object of the present invention is to provide an anti-aging agent having an excellent effect in terms of safety, stability in a preparation, and action effect.

As a result of diligent studies in view of the above circumstances, the present inventors have found that, although pentaerythritol generally exhibits little moisturizing action as expected for sugar alcohols, it has a wrinkle improvement effect, a skin elasticity recovery effect, It was found that it has an antioxidant effect and is useful as an active ingredient of an anti-aging agent, and the present invention has been completed.
That is, the present invention provides an anti-aging agent containing pentaerythritol as an active ingredient.
Moreover, the aging skin improving agent, wrinkle improving agent, skin tension recovery agent, and skin sagging improving agent which use the pentaerythritol of this invention as an active ingredient are provided.
Furthermore, this invention provides the skin external composition for wrinkle improvement containing a pentaerythritol.

  Pentaerythritol can be used as an anti-aging agent that is excellent in wrinkle improvement effect, skin elasticity increase effect and antioxidant effect, and has high safety and stability. Therefore, the external composition for skin containing pentaerythritol has an aging skin improvement effect such as wrinkle improvement for aging skin, recovery of skin tension, improvement of skin sagging, and skin aging prevention effect.

The continuous test result which uses centerline average roughness (Ra) as a parameter | index is shown [(a) Example 1, (b) Comparative example 1]. (*: P <0.05 t-test vs before continuous use) The continuous test result which uses 10-point average roughness (Rz) as an index is shown [(a) Example 1, (b) Comparative Example 1]. (**: p <0.01 t-test vs before continuous use) The continuous test result using the maximum height (Rmax) of the surface roughness as an index is shown [(a) Example 1, (b) Comparative Example 1]. (*: P <0.05 t-test vs before continuous use)

  The active ingredient of the anti-aging agent of the present invention is pentaerythritol. Pentaerythritol is a kind of sugar alcohol represented by the following structural formula (1), and is a known compound that is industrially used as a rosin ester raw material, an alkyd resin raw material, a synthetic lubricant raw material, or the like.

  Pentaerythritol can be chemically synthesized from formaldehyde and acetaldehyde, and is supplied as pentalit (registered trademark) by Guangei Chemical Industry Co., Ltd.

  Pentaerythritol has a wrinkle improving effect, a skin elasticity increasing effect, and an antioxidant effect, as shown in Examples below, and can be used as an anti-aging agent for the purpose of improving and preventing skin aging. it can. Especially as an aging skin improvement agent, such as a wrinkle improving agent for wrinkles made by aging, a skin tension recovery agent lost by aging, and a skin sag improving agent caused by aging etc. Useful.

  Pentaerythritol is an anti-aging active ingredient that prevents and ameliorates the symptoms of skin aging manifested by aging and photoaging. It is possible to mix | blend with the skin external composition for wrinkle improvement. Examples of the external composition for skin include cosmetics, quasi-drugs, pharmaceuticals and the like, and cosmetics are particularly preferable.

  Examples of the external composition for skin of the present invention include basic cosmetics such as emulsions, creams, lotions, essences and packs, makeup cosmetics such as lipsticks, foundations, liquid foundations, makeup press powders, hair shampoos, hair rinses, Hair treatments, conditioners, hair dyes, hair cosmetics such as hair styling agents, cleansing cosmetics such as facial cleansers, body shampoos, and soaps, as well as bathing agents, of course, but are not limited thereto. The form is preferably a water-in-oil emulsion composition, an oil-in-water emulsion composition, an aqueous composition, a gel-like composition, or the like from the viewpoint of causing pentaerythritol to act on the skin.

  In the composition for external use of the skin of the present invention, when pentaerythritol is blended as an active ingredient for anti-aging, the content of pentaerythritol may be appropriately determined according to the form and cannot be generally defined. Is preferably 0.001% by mass (hereinafter simply referred to as “%”) or more, more preferably 0.01% or more, and still more preferably 0.1% or more, based on the total amount of the external composition for skin. Moreover, 50% or less is preferable, 10% or less is more preferable, and 5% or less is further more preferable. As a specific range, 0.001-50% is preferable, More preferably, it is 0.01-10%, More preferably, it is 0.1-5%. Within these ranges, the excellent effect of pentaerythritol can be exhibited.

  In addition, in addition to the above, a dye, a fragrance, an antiseptic, a surfactant, a pigment, and the like can be appropriately blended in the composition for external use of the present invention within a range in which the object of the present invention is achieved.

  In the composition for external use of the skin of the present invention, in addition to the essential components described above, optional components that are usually used can be used as long as they do not impair the effects of the present invention. Examples of these components include various surfactants such as anionic surfactants, cationic surfactants, and nonionic surfactants, oil components, ultraviolet absorbers, preservatives, moisturizers, polymers, and amino acid derivatives. , Sugar derivatives, fragrances, water, alcohol, thickeners, colorants, sequestering agents, antioxidants, drugs, extracts derived from animals and plants, pH adjusters, and the like.

  In relation to the above-described embodiments, the present invention further discloses the following embodiments.

<1> An anti-aging agent comprising pentaerythritol as an active ingredient.

<2> An aging skin improving agent containing pentaerythritol as an active ingredient.
<3> A wrinkle improving agent containing pentaerythritol as an active ingredient.
<4> A skin tension recovery agent containing pentaerythritol as an active ingredient.
<5> An agent for improving skin sagging comprising pentaerythritol as an active ingredient.
<6> An agent for preventing skin aging comprising pentaerythritol as an active ingredient.
<7> An antioxidant containing pentaerythritol as an active ingredient.
<8> Use of pentaerythritol as an anti-aging agent.
<9> Use of <8>, wherein the anti-aging agent is either an aging skin improving agent or a skin aging preventing agent.
<10> Use of <8>, wherein the anti-aging agent is any of a wrinkle improving agent, a skin tension restoring agent, or a skin sagging improving agent.
<11> Use of pentaerythritol as an antioxidant.
<12> Use of pentaerythritol for the production of an anti-aging agent.
<13> Use of <12>, wherein the anti-aging agent is either an aging skin improving agent or a skin aging preventing agent.
<14> Use of <12>, wherein the anti-aging agent is any of a wrinkle improving agent, a skin tension restoring agent, or a skin sagging improving agent.
<15> Use of pentaerythritol for the production of antioxidants.
<16> Use of pentaerythritol for non-therapeutic improvement method of wrinkles.
<17> Use of pentaerythritol for a non-therapeutic method of restoring skin tension.
<18> Use of pentaerythritol for a non-therapeutic method of improving skin sagging.
<19> The use according to any one of <16> to <18>, wherein the non-therapeutic method is external use in the form of a cosmetic or quasi-drug of pentaerythritol.
<20> A method for improving aging skin by topically applying pentaerythritol to the skin.
<21> The method according to <20>, wherein the improvement of aging skin is any one of improvement of wrinkles, restoration of skin tension, and improvement of skin sagging.
<22> The method according to <20>, wherein the application to the skin is a non-therapeutic application.
<23> The method according to <22>, wherein the non-therapeutic application is a cosmetic or quasi-drug application.
<24> An anti-aging skin external composition containing pentaerythritol.
<25> A composition for external application to the skin for improving wrinkles, comprising pentaerythritol.
<26> A composition for external application for skin tension recovery containing pentaerythritol.
<27> A composition for external use for skin sagging improvement containing pentaerythritol.
<28> The content of pentaerythritol as an active ingredient is preferably 0.001% or more, more preferably 0.01% or more, and still more preferably 0.1% or more, based on the total amount of the composition for external use on the skin. In addition, the composition for external use in skin according to any one of <24> to <27>, which is preferably 50% or less, more preferably 10% or less, and still more preferably 5% or less.
<29> The content of pentaerythritol is preferably 0.001 to 50%, more preferably 0.01 to 10%, still more preferably 0.1 to 5%, based on the total amount of the composition for external use on the skin. <24>-<28> The skin external composition in any one.
<30> The external composition for skin according to any one of <24> to <29>, wherein the dosage form is a water-in-oil emulsion composition, an oil-in-water emulsion composition, an aqueous composition, or a gel composition.
<31> The external composition for skin according to any one of <24> to <30>, wherein the external composition for skin is a cosmetic.

  Hereinafter, although this invention is explained in full detail based on a test example and an Example, the technical scope of this invention is not restrict | limited by them.

  With respect to the moisture retention performance that sugar alcohols generally have, pentaerythritol was evaluated by the following hygroscopicity test and moisture retention test. As a comparative control, erythritol, which is a sugar alcohol having four hydroxyl groups in the molecule as in pentaerythritol, was used.

Test Example 1 (Hygroscopic test)
The hygroscopicity test was carried out as follows by partially modifying the method described in Cosmetic Society Journal, Vol. 8, No. 2, page 131 (1984). About 100 mg of the dried sample was precisely weighed into a plastic cup (Sanko Plastic Co., Ltd.) having an inner diameter of 1.2 cm. A dry sample precisely weighed was placed in a desiccator (relative humidity 91%) containing a saturated aqueous ammonium sulfate solution stored in a constant temperature room at 25 ° C., and the desiccator was left in the constant temperature room at 25 ° C. to absorb moisture. The weight of the sample was measured 1, 2, 3, and 7 days after standing, and the moisture absorption rate was determined according to the following formula. The results are shown in Table 1.

Moisture absorption (%) = [(Wt−W0) / W0] × 100
(W0: Weight before standing, Wt: Weight at each measurement)

  As shown in Table 1, it can be seen that the control erythritol has hygroscopicity, whereas pentaerythritol has almost no hygroscopicity and has a very low potential as a humectant. In order to further confirm this result, the following moisture retention test was conducted.

Test example 2 (humidity retention test)
A 5.0 mass% aqueous solution of the evaluation sample was prepared and used as a test sample. After the subject's forearm was washed with a face-washing foam, it was acclimated for 20 minutes in a constant temperature and humidity chamber (25 ° C., 55%). After acclimatization, the stratum corneum moisture content of the forearm was measured using SKICON-200 (manufactured by IBI S). The test sample was applied to the forearm of the subject at 20 μL / cm ² and allowed to stand for 20 minutes until the test sample was dry. The stratum corneum moisture content was measured 60 minutes and 120 minutes after application of the test sample in the same manner as described above. The measurement results are shown in Table 2.

  As shown in Table 2, it is clear that erythritol having hygroscopicity significantly increases the stratum corneum moisture content when applied to the skin and functions as a moisturizing agent. On the other hand, pentaerythritol shows no increase in the stratum corneum moisture content due to coating, and conversely, the stratum corneum moisture content decreases after 120 minutes, indicating that it hardly has a function as a humectant.

Evaluation Example 3 (Evaluation of antioxidant power)
According to the following method, the antioxidant power of pentaerythritol was evaluated using hydroxy radical scavenging ability as an index.
(1) KH ₂ PO ₄ aqueous solution (50 mmol / L) 0.4 mL, test compound 0.1 mL, EDTA aqueous solution (1.04 mmol / L) 0.1 mL, iron chloride aqueous solution (1 mmol / L) 0.1 mL, ascorbic acid Aqueous solution (1 mmol / L) 0.1 mL, deoxyribose aqueous solution (28 mmol / L) 0.1 mL, and hydrogen peroxide (10 mmol / L) 0.1 mL were mixed and kept at 37 ° C. for 1 hour.
(2) After 1 hour, 1 mL of a 20% trichloroacetic acid aqueous solution and 0.5 mL of a 0.67% thiobarbituric acid aqueous solution were added and held in a boiling water bath for 10 minutes.
(3) After 10 minutes, the mixture was allowed to cool, the absorbance (532 nm) was measured, and the hydroxy radical elimination rate was calculated from the following formula. The evaluation results are shown in Table 3.

Hydroxy radical elimination rate (%) = [1- (A−B) / (C−D)] × 100
A: Absorbance when test compound is added B: Absorbance when hydrogen peroxide is changed to water C: Absorbance when test compound is changed to water D: Absorbance when test compound and hydrogen peroxide are changed to water

  From the results of this test, it was found that pentaerythritol has significantly superior hydroxy radical scavenging ability than erythritol. Therefore, pentaerythritol functions as an effective skin aging preventive agent against the deterioration of the antioxidant mechanism due to aging and the progress of skin aging due to oxidative stress caused by ultraviolet irradiation in daily life.

Test Example 4 (Continuous human test)
Twelve healthy men aged 35 to 51 (average age 44.0 years) were used as panelists. The pentaerythritol-containing gel preparation shown in Table 4 (Example 1) and a placebo gel preparation (Comparative Example 1) excluding only pentaerythritol were used as evaluation samples. Two kinds of evaluation samples were applied to the half face continuously for one month, and the following two items were evaluated before continuous use and after one month of continuous use. In order to keep the measurement conditions the same as much as possible, the measurement was carried out after washing with a face-washing foam and then resting and acclimatizing for 20 minutes in a constant temperature and humidity room (25 ° C., 30%).

[Evaluation item 1: Evaluation of skin elasticity (skin wrinkles, sagging, and elasticity)]
The elasticity of the cheek skin was measured using a cut meter (MPA580; Courage + Khazaka electronic). The evaluation results are shown as relative values when the value before continuous use is set to 100. The results are shown in Table 5.

[Evaluation Item 2: Wrinkle Replica Analysis of Eyes]
Wrinkle replicas were collected with SILFLO (registered trademark) (manufactured by FLEXICO DEVELOPMENTS) from around the left and right eyes, with their eyes closed on their back. The three-dimensional shape of the collected replica was measured by PRIMOS Compact (manufactured by GF Messtechnik), and the line roughness at the corner of the eye corner was image-analyzed using the attached software. As parameters for analyzing the line roughness, centerline average roughness (Ra), ten-point average roughness (Rz), and maximum height of surface roughness (Rmax) were used.

  As shown in Table 5, it can be seen that the gel preparation of Example 1 containing pentaerythritol as an anti-aging active ingredient significantly increased skin elasticity compared to Comparative Example 1. The value of skin elasticity is lowered due to loss of skin tension or sagging of the skin due to aging or the like. Therefore, it can be seen that pentaerythritol exhibits a function of restoring skin tension or improving skin sagging by increasing skin elasticity.

  1 to 3 show the evaluation results of the wrinkle improvement effect based on the line roughness analyzed from the three-dimensional shape of the wrinkle replica. As shown in the figure, the gel preparation containing pentaerythritol has a significantly higher line roughness than that before continuous use, regardless of the analysis parameters of Ra value, Rz value, and Rmax value. It had the effect of reducing and improving wrinkles.

  From the results of Test Example 4, it was confirmed that pentaerythritol functions effectively for restoring skin tension, improving skin sagging, and improving wrinkles. As shown in the results of Test Examples 1 and 2, since pentaerythritol has almost no moisturizing property, these effective functions are not due to the moisturizing performance that sugar alcohols generally have. It is based on another mechanism and can be said to be a remarkably excellent effect that cannot be predicted from the moisture retention ability of pentaerythritol.

  In addition, during the test period, the gel preparation of Example 1 is stable, and there is no subject in whom the skin irritation reaction and the skin sensitization reaction are observed in the applied site, and it is excellent in terms of safety. It could be confirmed.

  Various external compositions for skin containing pentaerythritol as an active ingredient for anti-aging (wrinkle improvement) were produced by conventional methods (Examples 2 to 6). In any case, no problem was found in the blending characteristics. In addition, all compounding quantities are the mass%.

Example 2 (milky lotion)

Example 3 (skin lotion)

Example 4 (Cream)

Example 5 (cream)

Example 6 (Sunscreen)

  Pentaerythritol functions effectively in improving wrinkles, increasing skin elasticity, and anti-oxidation, and improves aging skin improving agents such as wrinkle improving agents, skin tension recovery agents, skin sagging improving agents for aging skin, and prevention of skin aging. It can be used as an active ingredient of an agent. In addition, it is possible to provide various skin external compositions containing pentaerythritol as an active ingredient for the purpose of improving wrinkles, restoring skin tension and improving skin sagging.

Claims (4)

An agent for restoring skin tension containing pentaerythritol as an active ingredient (except when used together with a peptide containing the sequence of Glu-Glu-Met-Gln-Arg-Arg or a pomegranate (Punica granatum) flower extract). . An agent for improving skin sagging containing pentaerythritol as an active ingredient (except when used together with a peptide containing the sequence of Glu-Glu-Met-Gln-Arg-Arg or a flower extract of pomegranate (Punica granatum)). .   Skin external composition for recovery of skin tension containing pentaerythritol (except when used with a peptide containing the sequence of Glu-Glu-Met-Gln-Arg-Arg or a flower extract of pomegranate (Punica granatum)) .)   An external composition for skin sagging improvement containing pentaerythritol (except when used with a peptide containing the sequence of Glu-Glu-Met-Gln-Arg-Arg or a pomegranate (Punica granatum) flower extract) .)

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