JP2015063469A - External preparation for skin - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an external preparation for skin which has good skin compatibility, is excellent in persistence of a moisturizing effect, a wrinkle-improving effect, a skin texture-uniforming effect, and a stains-improving effect, as well as is excellent in a rash-improving effect.SOLUTION: The invention provides an external preparation for skin containing (a) 0.0001-5 mass% of 1-acyl-2,3-cyclic phosphatidic acid represented by the formula [I] or a salt thereof; (b) 1-10 mass% of alkanediol of carbon numbers 5-8; (c) 0.001-5 mass% of α-hydroxy acid or a salt thereof. (In the formula, R represents acyl group of carbon numbers 10-22.)

Description

  The present invention relates to an external preparation for skin that has good conformability to the skin, is excellent in durability of moisturizing effect, wrinkle-improving effect, skin-texturing effect, stain-improving effect, and rash-improving effect.

With the rapid arrival of an aging society in recent years, an increasing number of people have various skin problems. A typical problem is skin aging. Skin aging progresses with aging, ultraviolet rays, etc., and appears as spots, dullness, freckles, decreased skin elasticity, wrinkles, texture irregularities, pore enlargement, and the like. In particular, the increase in wrinkles, which is a remarkable change in appearance, is regarded as a symbol of the skin aging phenomenon.
There are stains that are visible to the surface of the skin with the naked eye and hidden stains that are hidden with the naked eye and are hidden inside the skin. Hidden stains will eventually appear on the skin surface as time passes, so there are cases where the whitening effect cannot be realized only with care for normal spots visible to the naked eye.

  In addition, an increasing number of people are suffering from rash caused by an obstructive environment in which excrement, sweat, etc. remain on the skin surface by wearing diapers and underwear. Specific examples include diaper rashes in the elderly and babies wearing diapers, as well as rashes in the wearing area of underwear (bras, girdles, etc.) such as correction and correction underwear. An increasing number of people suffer from rashes, and there is a strong demand for external preparations for skin that improve rashes.

  However, various external preparations for skin containing ingredients that are expected to be anti-aging have been proposed, but they have not only an anti-aging effect that is not sufficient, but also the durability of the effect is insufficient or the effects vary. May occur. In addition, various external preparations for skin containing ingredients for improving rash have been proposed, but they focus on the rash improvement effect, do not have wrinkle improvement effect, stain improvement effect, etc., and The feeling of use such as familiarity with the skin was not satisfactory.

On the other hand, various skin external preparations in which 1-acyl-2,3-cyclic phosphatidic acid (or a salt thereof) is blended as an active ingredient for suppressing the skin aging phenomenon have been proposed. For example, Patent Document 1 suggests that an anti-wrinkle effect can be expected from an external preparation for skin containing 1-acyl-2,3-cyclic phosphatidic acid (or a salt thereof).
Patent Document 2 describes that a composition for external use of skin utilizing the hyaluronic acid production enhancing action of 1-acyl-2,3-cyclic phosphatidic acid (or a salt thereof) is useful for improving skin atrophy. Has been.
In Patent Document 3, a cosmetic containing 1-acyl-2,3-cyclic phosphatidic acid (or a salt thereof) as a constituent of liposomes provides an effect of smoothing the skin and firmness of the skin. It describes that it has an effect, has no stickiness, and can provide a moist feeling.
However, 1-acyl-2,3-cyclic phosphatidic acid (or a salt thereof) has low solubility in water and may cause precipitation and the like. In some cases, the wrinkle improvement effect was not sufficient.

Patent Document 4 discloses a therapeutic agent for atopic dermatitis containing 1-acyl-2,3-cyclic phosphatidic acid (or a salt thereof) as an active ingredient. However, this therapeutic agent for dermatitis did not improve rash caused by occlusion, which has a different cause from atopic dermatitis.
That is, in a skin external preparation containing 1-acyl-2,3-cyclic phosphatidic acid (or a salt thereof), the skin feel such as the familiarity with the skin is good, and the durability of the moisturizing effect is improved. An external preparation for skin that has excellent effects on improving skin, such as an effect, an effect of improving skin texture, an effect of improving spots, and an effect of improving rash has not been developed yet.

US Pat. No. 5,238,965 JP 2002-363081 A JP 2008-222463 A JP 2010-202585 A

  In view of the above circumstances, the present invention is an external preparation for skin that has good conformability to the skin, excellent moisturizing effect, wrinkle improving effect, skin texture adjusting effect, stain improving effect, and rash improving effect The purpose is to provide.

  The inventors of the present invention have made extensive studies in order to solve the above problems. As a result, (a) a compound represented by the formula [I] or a salt thereof, (b) an alkanediol having 5 to 8 carbon atoms, (c) It has been found that by combining α-hydroxy acid or a salt thereof in a specific ratio, the intended external preparation for skin can be obtained, and the present invention has been completed.

（式中、Ｒは炭素数１０〜２２のアシル基を表す。） That is, the skin external preparation of the present invention comprises (a) 0.0001 to 5% by mass of a compound represented by the formula [I] or a salt thereof, and (b) 1 to 10% by mass of an alkanediol having 5 to 8 carbon atoms. %, (C) an external preparation for skin containing 0.001 to 5% by mass of α-hydroxy acid or a salt thereof.

(In the formula, R represents an acyl group having 10 to 22 carbon atoms.)

  The external preparation for skin of the present invention has good compatibility with the skin, has a long-lasting moisturizing effect, an improvement effect on wrinkles, an effect of adjusting the texture of the skin, an effect of improving the stain, particularly an effect of improving the hidden stain, and is caused in an obstructive environment. Excellent in improving rash.

  Hereinafter, embodiments of the present invention will be described. The skin external preparation of this invention contains the following (a)-(c) component. First, the component (a) will be described.

[(A) Compound represented by Formula [I]]
The component (a) used in the external preparation for skin of the present invention is 1-acyl-2,3-cyclic phosphatidic acid represented by the formula [I] or a salt thereof. Hereinafter, “1-acyl-2,3-cyclic phosphatidic acid or a salt thereof” is also referred to as “substituted cyclic phosphatidic acid (salt)”.
In the formula [I], R is an acyl group having 10 to 22 carbon atoms, preferably an acyl group derived from a linear or branched fatty acid having 12 to 20 carbon atoms.
Examples of fatty acids include saturated fatty acids such as capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, isostearic acid, palmitoleic acid, oleic acid, linoleic acid, linolenic acid, arachidonic acid, eicosapentaenoic acid, docosahexaenoic acid, etc. Of these fatty acids, and coconut oil fatty acid, palm kernel oil fatty acid, beef tallow fatty acid, hardened beef tallow fatty acid, soybean phospholipid-derived fatty acid, and egg yolk phospholipid-derived fatty acid. Among them, preferred are soybean phospholipid-derived fatty acids and egg yolk phospholipid-derived fatty acids, and more preferred are soybean phospholipid-derived fatty acids.

The 1-acyl-2,3-cyclic phosphatidate used in the skin external preparation of the present invention is represented by the following formula [II].

  Examples of M in the formula [II] include alkali metals, ammonium, and organic ammonium. Examples of the alkali metal include sodium and potassium. Examples of organic ammonium include butylammonium, triethylammonium, and tetramethylammonium. Among these, sodium and potassium are preferable from the viewpoint of easy availability and solubility.

Examples of the method for producing a substituted cyclic phosphatidic acid (salt) used in the external preparation for skin of the present invention include a method of enzymatic treatment of lysophosphatidylcholine with phospholipase D, and a method of chemical synthesis (Japanese Patent Laid-Open No. 6-228169). Etc.).
Moreover, the purity and form of the substituted cyclic phosphatidic acid (salt) used in the external preparation for skin of the present invention are not particularly limited. For example, pure products, those containing excipients, liquids, and powders can be used. Specifically, powder containing 1-acyl-2,3-cyclic phosphatidic acid obtained by lyophilization using cyclodextrin as an excipient can be mentioned. According to this freeze-drying method, it is possible to obtain a lipid that is easy to handle and is easy to handle with an excipient.
In addition, 1-acyl-2,3-cyclic phosphatidic acid can be obtained commercially as “CyPA-ET” and “CyPA-PW” manufactured by NOF Corporation. “CyPA-ET” and “CyPA-PW” both contain 1-acyl-2,3-cyclic phosphatidic acid, which is an acyl group of soybean phospholipid-derived fatty acid, and the fatty acid composition of soybean phospholipid-derived fatty acid is: Palmitic acid 20.4% by mass, stearic acid 3.2% by mass, oleic acid 11.3% by mass, linoleic acid 57.6% by mass, linolenic acid 6.1% by mass, and other 1.4% by mass.

  (A) A component is 0.0001-5 mass% with respect to skin external preparation, Preferably it is 0.001-2 mass%, More preferably, it contains in the ratio of 0.05-1 mass%. When it is less than 0.0001% by mass, the durability of the moisturizing effect and the wrinkle improving effect may be reduced. If it exceeds 5% by mass, it may become sticky after use or the stability over time may deteriorate.

[(B) Alkanediol having 5 to 8 carbon atoms]
The component (b) used in the external preparation for skin of the present invention is an alkanediol having 5 to 8 carbon atoms, and has a structure in which two hydroxyl groups are added to a linear or branched hydrocarbon. If the alkanediol has less than 5 carbon atoms, it may irritate the skin. If the alkanediol exceeds 8 carbon atoms, the wrinkle improving effect and the stain improving effect may be reduced.

  Specific examples of the alkanediol having 5 to 8 carbon atoms include isopentanediol, 1,2-pentanediol, 1,3-pentanediol, 1,4-pentanediol, 1,5-pentanediol, 1,2- Hexanediol, 1,3-hexanediol, 1,4-hexanediol, 1,5-hexanediol, 1,6-hexanediol, 3-methyl-1,5-pentanediol, 2-methyl-2,4- Pentanediol, 1,2-heptanediol, 1,3-heptanediol, 1,4-heptanediol, 1,5-heptanediol, 1,6-heptanediol, 1,7-heptanediol, 2,4-heptane Diol, 3,4-heptanediol, 1,2-octanediol, 2,3-octanediol, 2-ethyl-1,3-hexene Njioru, 2-butyl-2-ethyl-1,3-propanediol, 2,5-dimethyl-2,5-hexanediol, and the like. Among these, 1,2-pentanediol and 1,2-hexanediol are preferable from the viewpoint of easy availability, odor, ease of blending, and the like. In the present invention, one or more of these alkanediols can be used.

  (B) A component is contained in the ratio of 1-10 mass% with respect to skin external preparation, Preferably it is 2-8 mass%, More preferably, it is 3-6 mass%. When the amount is less than 1% by mass, the conformability to the skin may be deteriorated, the wrinkle improving effect, the effect of adjusting the texture of the skin, and the stain improving effect may be reduced. If it exceeds 10% by mass, it may become sticky after use.

[(C) α-hydroxy acid or salt thereof]
The component (c) used in the external preparation for skin of the present invention is an α-hydroxy acid or a salt thereof, which is a kind of organic acid that exists widely in nature, and is a compound having a hydroxyl group at the α-position of the carboxylic acid. Hereinafter, “α-hydroxy acid or a salt thereof” is also referred to as “AHA”. AHA is also called fruit acid because it is contained in a large amount in fruits. AHA is also present in the living body, and is known to be involved, for example, in the production of energy such as ATP (adenosine triphosphate) and biosynthetic substances such as amino acids in the citric acid cycle. Yes.

  Examples of the AHA used in the external preparation for skin of the present invention include α-hydroxy acids such as citric acid, lactic acid, malic acid, tartaric acid and glycolic acid, and alkali metal salts, alkaline earth metal salts and ammonium thereof. Examples include salts, amine salts, organic amine salts, basic amino acid salts, and the like, and the hydrates described above. In addition, you may use fruit juices, such as an apple containing AHA and citrus. Of these, citric acid, citric acid hydrate, sodium citrate, sodium citrate hydrate, lactic acid, sodium lactate, glycolic acid, and sodium glycolate are preferable in terms of feeling of use and the like. In the present invention, one or more of these AHAs can be used.

  (C) A component is 0.001-5 mass% with respect to a skin external preparation, Preferably it is 0.01-3 mass%, More preferably, it contains in the ratio of 0.1-2 mass%. If it is less than 0.001% by mass, the effect of adjusting the texture of the skin may be reduced. If it exceeds 5% by mass, the rash improvement effect may be reduced, skin irritation may appear, or it may become sticky after use.

The external preparation for skin of the present invention can be provided in various dosage forms and forms according to conventional methods. For example, it can be provided in a dosage form such as lotion, milky lotion, gel, cream, ointment, spray and the like, and can be provided in various forms such as a form impregnated in a nonwoven fabric.
In the external preparation for skin of the present invention, various additives commonly used in external preparations and pharmaceuticals can be blended depending on the provided dosage form and form, as long as the effects of the present invention are not impaired. .

Hereinafter, the present invention will be described more specifically with reference to examples and comparative examples.
[Examples 1-6, Comparative Examples 1-5]
A skin lotion preparation for skin lotion was prepared according to a conventional method at the blending ratios shown in Table 1 (Examples 1 to 6) and Table 2 (Comparative Examples 1 to 5).
Using the obtained skin external preparation, 6 items were evaluated by the following methods. The results are shown in Tables 1 and 2.

(1) Familiarity to the skin Twenty women (30 to 48 years old) were panelists, and each paneler determined the touch when the skin external preparation was used on the entire face as follows.
2 points: When the skin familiarity is clearly good.
1 point: When familiarity with skin is slightly good.
0 point: When it is felt that the familiarity with the skin is bad.

The total score of 20 people was calculated and evaluated as follows.
A: No. of people who have a total score of 35 or more and 0 points: A skin external preparation with very good skin adaptability.
○: Total score is 25 points or more and less than 35 points, or total score is 35 points or more, and 1 or more and 2 or less people are judged to be 0 points: skin external preparation with good skin adaptability is there.
(Triangle | delta): A total score is 15 points or more and less than 25 points | pieces: It is a skin external preparation with a slightly good adaptability to skin.
X: The total score is less than 15: It is an external preparation for skin having poor adaptability to the skin.

(2) Sustainability of moisturizing effect 20 women (30 to 48 years old) are panelists, and each paneler uses a topical skin preparation on the entire face in the morning of winter (February), and then the skin on the evening of that day. The state was determined as follows.
2 points: When feeling moisturized.
1 point: When a feeling of moisture retention is somewhat felt.
0 point: When there is no moisturizing feeling.

The total score of 20 people was calculated and evaluated as follows.
A: The total score is 35 points or more, and 0 people are determined to be 0 points: a skin external preparation having a very high moisturizing effect.
○: The total score is 25 or more and less than 35 points, or the total score is 35 or more and 1 or more and 2 or less people are determined: a skin external preparation having a high moisturizing effect.
(Triangle | delta): A total score is 15 points or more and less than 25 points: It is a skin external preparation with a high moisturizing effect.
X: The total score is less than 15: a skin external preparation having a low moisturizing effect.

(3) Wrinkle improvement effect 22 women (30-65 years old) with wrinkles in the corners of the eyes are used as panelists, and each paneler uses the topical skin preparation twice a day for 3 consecutive months for 3 months. The condition of wrinkles at the corners of the eyes was evaluated as follows.
For the wrinkles (same part) of the corner of the eye before the start of use of the external preparation for skin and after continuous application for 3 months, within a range of 10 × 10 mm or more from a part about 5 mm away from the eye when lightly closed A wrinkle replica (“Silicon ASB-01-W” manufactured by Asahi Biomed Co., Ltd.) was collected. Three-dimensional analysis ("PRIMOS (including attached software)" manufactured by GFM) is performed on the collected wrinkle replica, and the maximum wrinkle average depth (μm, average depth for wrinkles with the maximum volume existing in the analysis range) Was calculated.
The wrinkle replica before the start of use and the wrinkle replica after continuous application for 3 months were matched in shape by an automatic alignment function. From the obtained maximum wrinkle average depth, the wrinkle improvement rate was calculated from the following formula. In addition, the wrinkle improvement rate in Table 1 and Table 2 is an average value of 22 panelists.

Wrinkle improvement rate (%) = (maximum wrinkle average depth before start of use of skin external preparation-maximum wrinkle average depth after continuous application for 3 months of skin external preparation) / maximum wrinkle average depth before start of use of external preparation of skin X 100
A: Wrinkle improvement rate of 35% or more: An external preparation for skin having a very excellent wrinkle improvement effect.
○: Wrinkle improvement rate of 25% or more and less than 35%: an external preparation for skin having an excellent wrinkle improvement effect.
Δ: Wrinkle improvement rate of 15% or more and less than 25%: A skin external preparation having a slight wrinkle improvement effect.
X: Wrinkle improvement rate of less than 15%: It is a skin external preparation having no wrinkle improvement effect.

(4) Effect of adjusting skin texture 20 women (30 to 48 years old) are panelists, and each paneler uses the topical skin preparation twice a day for 1 month on all faces. The skin condition was determined as follows.
2 points: When the skin feels clearly clear.
1 point: When the skin feels somewhat smooth.
0 point: When it feels that the effect of adjusting the texture of the skin is not seen.

The total score of 20 people was calculated and evaluated as follows.
A: The total score is 35 points or more, and 0 people are determined to be 0 points: a skin external preparation having an effect of preparing a very excellent skin texture.
○: The total score is 25 or more and less than 35, or the total score is 35 or more and 1 or less and 2 or less people: The skin having the effect of adjusting the excellent skin texture It is an external preparation.
Δ: Total score of 15 points or more and less than 25 points: An external preparation for skin having an effect of slightly adjusting skin texture.
X: The total score is less than 15: It is an external preparation for skin that does not have an effect of adjusting the texture of the skin.

(5) Blemish improvement effect 20 women (30 to 48 years old) were used as the panelists, and after each panel washes, the topical skin preparation was used twice a day for 4 consecutive weeks on the entire face. Before and after the end of the test, the entire face was photographed with black light using a cosmetic full face photographing device (Facial Stage DM-3, manufactured by Schott Moritex Co., Ltd.), and the stains hidden inside the skin that cannot be seen with the naked eye The state of was evaluated. The average area of hidden spots was measured by the image analysis method, and the hidden spot improvement rate was calculated from the following formula. In addition, the hidden spot improvement rate in Table 1 and Table 2 is an average value of 20 panelists.

Hidden Blemish Improvement Rate (%) = (Hidden Blemish Area Before Starting Use of Skin Topic Agent−Hidden Blemish Area After Four Weeks of Skin Topical Application) / Hidden Blemish Area Before Starting Use of Skin Topical Agent × 100
：: Hidden spot improvement rate of 10% or more: It is a skin external preparation having a very excellent hidden spot improvement effect.
○: Hidden spots improvement rate of 5% or more and less than 10%: It is an external preparation for skin having an excellent effect of improving hidden spots.
(Triangle | delta): The hidden spot improvement rate 2% or more and less than 5%: It is a skin external preparation which has a slight hidden spot improvement effect.
X: Hidden spot improvement rate of less than 2%: It is a skin external preparation having no hidden spot improvement effect.

(6) Effect of rash improvement 20 elderly people suffering from diaper rash were panelists, and each paneler applied the topical skin preparation twice a day for 1 week continuously. The skin condition after one week was determined as follows.
2 points: When the rash is clearly improved.
1 point: When the rash feels somewhat improved.
0 points: When it is felt that the rash improvement effect is not seen.

The total score of 20 people was calculated and evaluated as follows.
A: The total score is 35 points or more and the number of people determined to be 0 points: 0: An external preparation for skin having a very excellent rash improvement effect.
○: Total score is 25 points or more and less than 35 points, or total score is 35 points or more, and 1 or more and 2 or less people are determined to be: 0 is a skin external preparation having an excellent rash improvement effect. is there.
Δ: Total score of 15 points or more and less than 25 points: A skin external preparation having a slight rash improvement effect.
X: The total score is less than 15: It is an external preparation for skin having no rash improvement effect.

1) “CyPA-ET” manufactured by NOF Corporation: An aqueous solution containing 4% by mass of 1-acyl-2,3-cyclic phosphatidic acid, which is an acyl group of soybean phospholipid-derived fatty acid, and 40% by mass of ethanol. In addition, the numerical value of (product) in a table | surface represents the "CyPA-ET" density | concentration which is a product.
2) “CyPA-PW” manufactured by NOF Corporation: Powder containing 10% by mass of 1-acyl-2,3-cyclic phosphatidic acid which is an acyl group of fatty acid derived from soybean phospholipid and 50% by mass of cyclodextrin. In addition, the numerical value of (Product) in the table represents the “CyPA-PW” concentration that is a product.

  1) “CyPA-PW” manufactured by NOF Corporation: Powder containing 10% by mass of 1-acyl-2,3-cyclic phosphatidic acid, which is an acyl group of soybean phospholipid-derived fatty acid, and 50% by mass of cyclodextrin. In addition, the numerical value of (Product) in the table represents the “CyPA-PW” concentration that is a product.

  As shown in the results of Examples 1 to 6, all of the lotions according to the external preparation for skin of the present invention have good compatibility with the skin, and maintain the moisturizing effect, the wrinkle improving effect, and the skin texture. It can be understood that the effect and the spot improvement effect, particularly the hidden spot improvement effect are excellent, and the effect of improving the rash caused in the blockage environment is excellent.

On the other hand, in Comparative Examples 1-5, sufficient performance is not obtained.
Specifically, in Comparative Example 1, since the components (b) and (c) are not included, the moisture retention effect, the wrinkle improvement effect, the stain improvement effect, and the rash improvement effect are only slightly obtained. There is no conformity to the skin, and the effect of adjusting the texture of the skin is not obtained.
In Comparative Example 2, since the component (a) is not included, the familiarity to the skin and the effect of adjusting the texture of the skin are recognized, but the effect of improving the stain is only slightly obtained and the durability of the moisturizing effect is maintained. No wrinkle improvement effect or rash improvement effect has been obtained.
In Comparative Example 3, since the component (b) is not included, the effect of adjusting the texture of the skin is recognized, but the familiarity to the skin, the persistence of the moisturizing effect, the wrinkle improving effect, the stain improving effect, the rash improving effect Has been obtained only slightly.
In Comparative Example 4, since the component (c) is not included, the familiarity to the skin, the persistence of the moisturizing effect, the wrinkle improving effect, and the wrinkle improving effect are recognized, but the effect of adjusting the texture of the skin, the rash improving effect Has been obtained only slightly.
In Comparative Example 5, 1,3-butanediol and dipropylene glycol are blended in place of the component (b), so that the familiarity to the skin is recognized, but the durability of the moisturizing effect, the wrinkle improving effect, the skin The effect of improving the texture of the skin and the effect of improving stains are obtained only slightly, and the effect of improving rash is not obtained.

Example 7
According to a conventional method, an oil-in-water emulsion external preparation for skin was prepared at the blending ratio shown in Table 3.
Using the obtained external preparation for skin, 6 items were evaluated by the same method as in the above Examples. The results are shown in Table 3.

1) “CyPA-PW” manufactured by NOF Corporation: Powder containing 10% by mass of 1-acyl-2,3-cyclic phosphatidic acid, which is an acyl group of soybean phospholipid-derived fatty acid, and 50% by mass of cyclodextrin. In addition, the numerical value of (Product) in the table represents the “CyPA-PW” concentration that is a product.
2) “Eco Garm” manufactured by Dainippon Pharmaceutical Co., Ltd.
3) “Carbopol 940” manufactured by BF-Goodrich

  As shown in the results of Example 7, the emulsion according to the external preparation for skin of the present invention has good skin conformability, long-lasting moisturizing effect, wrinkle improving effect, skin texture adjusting effect, stain improving effect It can be understood that, in particular, the effect of improving hidden spots is excellent, and the effect of improving the rash caused in an obstructive environment is excellent.

Example 8
With the blending ratio shown in Table 4, an oil-in-water cream external preparation for skin was prepared according to a conventional method.
Using the obtained external preparation for skin, 6 items were evaluated by the same method as in the above Examples. The results are shown in Table 4.

  1) “CyPA-PW” manufactured by NOF Corporation: Powder containing 10% by mass of 1-acyl-2,3-cyclic phosphatidic acid, which is an acyl group of soybean phospholipid-derived fatty acid, and 50% by mass of cyclodextrin. In addition, the numerical value of (Product) in the table represents the “CyPA-PW” concentration that is a product.

  As shown in the results of Example 8, the cream according to the external preparation for skin of the present invention has good conformability to the skin, long-lasting moisturizing effect, wrinkle-improving effect, skin-texturing effect, and stain-improving effect. It can be understood that, in particular, the effect of improving hidden spots is excellent, and the effect of improving the rash caused in an obstructive environment is excellent.

Claims (1)

(A) 0.0001-5 mass% of 1-acyl-2,3-cyclic phosphatidic acid represented by the formula [I] or a salt thereof,
(B) 1 to 10% by mass of an alkanediol having 5 to 8 carbon atoms,
(C) 0.001-5 mass% of α-hydroxy acid or a salt thereof
Contains a topical skin preparation.

(In the formula, R represents an acyl group having 10 to 22 carbon atoms.)