JP2015124194A - External preparation for skin - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an external preparation for skin which has a good feeling to the skin such as good compatibility to the skin, and also has an excellent skin improving effect by porphyrin production inhibition, as well as has a long-lasting moisturizing effect, a wrinkle-improving effect, and a skin texture-uniforming 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 formula [I], or a salt thereof; (b) 1-10 mass% of alkanediol of carbon number 5-8; and (c) 0.01-5 mass% of polyoxyethylene sorbitan fatty acid ester or polyoxyethylene hardened castor oil. (where R represents an acyl group of carbon number 10-22.)

Description

  The present invention relates to an external preparation for skin having good skin feel, excellent moisturizing effect persistence, wrinkle improving effect, skin smoothing effect and skin improving effect by suppressing porphyrin production.

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.
Under such circumstances, 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, but also an insufficient sustainability of the effect, In some cases, the effect varies.

In addition, there is a problem of photosensitivity, which is a disease that causes skin symptoms such as papules, erythema, and blisters at the irradiated site by irradiation of light such as sunlight. One of the causes of photosensitivity is porphyrin, a photosensitive substance produced by P. acnes. If the production of porphyrin can be suppressed, the above skin symptoms can also be suppressed. Therefore, an external preparation for skin having a porphyrin production inhibitory effect is desired.
For example, Patent Document 1 discloses that tocopheryl phosphate and / or a salt thereof suppresses skin inflammation by antibacterial acne bacteria, but the effect has not yet been satisfactory.

On the other hand, various external preparations for skin containing 1-acyl-2,3-cyclic phosphatidic acid (or a salt thereof) have been proposed as active ingredients for suppressing the skin aging phenomenon. For example, Patent Document 2 suggests that an external preparation for skin containing 1-acyl-2,3-cyclic phosphatidic acid (or a salt thereof) can be expected to have an anti-wrinkle effect.
Patent Document 3 discloses that an external composition for skin utilizing hyaluronic acid production enhancing action by 1-acyl-2,3-cyclic phosphatidic acid (or a salt thereof) is useful for improving skin atrophy. Is described.
Furthermore, in Patent Document 4, cosmetics formulated with 1-acyl-2,3-cyclic phosphatidic acid (or a salt thereof) as a component of liposomes have an effect of smoothing the skin and an effect of giving the skin firmness. In addition, there is no sticky feeling and a moist feeling can be imparted.
However, since the external preparations for skin containing 1-acyl-2,3-cyclic phosphatidic acid (or a salt thereof) described in Patent Documents 2 to 4 do not have a porphyrin production inhibitory effect, photosensitivity It was not expected to improve the skin symptoms caused by.

In addition, 1-acyl-2,3-cyclic phosphatidic acid (or a salt thereof) has low solubility in water and may cause precipitation, etc., and when it is added to a skin external preparation, the moisturizing effect is sustained. In some cases, the wrinkle improvement effect was not sufficient.
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 is excellent in the effect and the effect of adjusting the texture of the skin and excellent in the effect of improving the skin by suppressing porphyrin production has not been developed yet.

JP 2006-213633 A US Pat. No. 5,238,965 JP 2002-363081 A JP 2008-222463 A

  The object of the present invention is to improve the skin by suppressing the porphyrin production while having good skin feel such as conformability to the skin and excellent moisturizing effect, wrinkle improving effect, skin smoothing effect. It is to provide an external preparation for skin that is also excellent in effect.

  As a result of intensive studies by the present inventors in order to solve the above problems, (a) 1-acyl-2,3-cyclic phosphatidic acid represented by the formula [I] or a salt thereof, (b) a carbon number of 5 The present invention was completed by finding that a skin external preparation capable of solving the above-mentioned problems can be obtained by combining 8 alkanediols, (c) polyoxyethylene sorbitan fatty acid ester or polyoxyethylene hydrogenated castor oil in a specific ratio. I came to let you.

（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 1-acyl-2,3-cyclic phosphatidic acid represented by the formula [I] or a salt thereof, and (b) 5 carbon atoms. It is an external preparation for skin containing 1 to 10% by mass of -8 alkanediol and 0.01 to 5% by mass of (c) polyoxyethylene sorbitan fatty acid ester or polyoxyethylene hydrogenated castor oil.

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

  The external preparation for skin of the present invention has a good feel to the skin, such as familiarity with the skin, and is excellent in the durability of the moisturizing effect, the effect of improving wrinkles, and the effect of adjusting the texture of the skin. Moreover, since the skin external preparation of this invention has a porphyrin production inhibitory effect, it suppresses the skin symptom of photosensitivity and is excellent also in the effect which improves skin.

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) 1-acyl-2,3-cyclic phosphatidic acid represented by the formula [I] or a salt thereof]
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].

（式中、Ｒは炭素数１０〜２２のアシル基を表し、Ｍ^＋はカチオンを表す。）

(In the formula, R represents an acyl group having 10 to 22 carbon atoms, and M ⁺ represents a cation.)

  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) include a method in which lysophosphatidylcholine is treated with phospholipase D, a method in which it is prepared by chemical synthesis (see JP-A-6-228169, etc.), and the like.

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 fatty acid derived from soybean phospholipid. The fatty acid composition of the fatty acid derived from soybean phospholipid is as follows: 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, Others are 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%. If it is less than 0.0001% by mass, the durability of the moisturizing effect and the effect of improving wrinkles may be reduced. If it exceeds 5% by mass, it may become sticky after use or the stability over time may be reduced.

[(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, the skin may be irritated, and if the alkanediol exceeds 8, the wrinkle 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%. If the amount is less than 1% by mass, the conformability to the skin may be reduced, or the effect of improving wrinkles and the texture of the skin may be reduced. If it exceeds 10% by mass, it may become sticky after use.

[(C) Polyoxyethylene sorbitan fatty acid ester or polyoxyethylene hydrogenated castor oil]
The component (c) used in the skin external preparation of the present invention is polyoxyethylene sorbitan fatty acid ester or polyoxyethylene hydrogenated castor oil.
The polyoxyethylene sorbitan fatty acid ester is obtained by adding ethylene oxide to sorbitan fatty acid ester which is an ester of sorbitol or sorbitan and a fatty acid. The number of moles of ethylene oxide added is preferably 15 to 30 moles, more preferably 20 to 30 moles from the viewpoint of stability.

  As the fatty acid forming the ester, a saturated or unsaturated fatty acid having 8 to 24 carbon atoms is suitable, for example, a single fatty acid such as lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, coconut oil fatty acid, beef tallow Mixed fatty acids derived from animal and vegetable oils such as fatty acids can be used. The number of carbon atoms of the fatty acid is preferably 8 to 22 and more preferably 12 to 18 from the viewpoint of stability. From the viewpoint of stability, the number of fatty acid esters is preferably 1 to 3, and more preferably 1 (that is, a monoester).

  Specific examples of the polyoxyethylene sorbitan fatty acid ester include polyoxyethylene (20 mol) sorbitan monolaurate, polyoxyethylene (20 mol) sorbitan monostearate, polyoxyethylene (20 mol) sorbitan monooleate, and the like. Can be mentioned. These components may be used alone or in combination of two or more.

  Polyoxyethylene hydrogenated castor oil is obtained by adding ethylene oxide to hydrogenated castor oil. The number of moles of ethylene oxide added is preferably 10 to 80, more preferably 20 to 60, from the viewpoint of stability. Specifically, polyoxyethylene (20 mol) hydrogenated castor oil, polyoxyethylene (40 mol) hydrogenated castor oil, polyoxyethylene (60 mol) hydrogenated castor oil, polyoxyethylene (80 mol) hydrogenated castor oil, etc. Can be mentioned. These components may be used alone or in combination of two or more.

  In the present invention, as the component (c), polyoxyethylene sorbitan fatty acid ester alone, polyoxyethylene hydrogenated castor oil alone, or an appropriate combination thereof can be used.

  (C) A component is 0.01-5 mass% with respect to skin external preparation, Preferably it is 0.1-3 mass%, More preferably, it contains in the ratio of 0.3-1 mass%. If the amount is less than 0.01% by mass, there is a possibility that the conformability to the skin, the porphyrin production inhibitory effect, and the stability may be reduced, and if it exceeds 5% by mass, stickiness may occur.

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 and 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, the following 5 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.
(Double-circle): The panelist who determined that the total score is 35 points or more and 0 points is zero. : Skin external preparation with very good compatibility with the skin.
○: The total score is 25 or more and less than 35, or the total score is 35 or more and the number of panelists determined to be 0 is 1 or more and 2 or less. : It is a skin external preparation with good compatibility with the skin.
Δ: The total score is 15 points or more and less than 25 points. : Skin external preparation with slightly better fit to the skin.
X: The total score is less than 15 points. : An external preparation for skin that is not well-familiar with 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.
(Double-circle): The panelist who determined that the total score is 35 points or more and 0 points is zero. : A skin external preparation with a very high moisturizing effect.
○: The total score is 25 or more and less than 35, or the total score is 35 or more and the number of panelists determined to be 0 is 1 or more and 2 or less. : A skin external preparation with a high moisturizing effect.
Δ: The total score is 15 points or more and less than 25 points. : A skin external preparation with a slightly high moisturizing effect.
X: The total score is less than 15 points. : A skin external preparation with a low moisturizing effect.

(3) Wrinkle improvement effect (wrinkle improvement rate)
Panels consisted of 22 women (30 to 65 years old) with wrinkles in the corners of the eyes, and each paneler used the topical skin preparation twice a day for 3 consecutive months, and the wrinkles in the corners of the eyes after 3 months. 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 20% or more and less than 35%: An external preparation for skin having an excellent wrinkle improvement effect.
Δ: Wrinkle improvement rate of 5% or more and less than 20%: a skin external preparation having a slight wrinkle improvement effect.
X: Wrinkle improvement rate of less than 5%: 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.
(Double-circle): The panelist who determined that the total score is 35 points or more and 0 points is zero. : An external preparation for skin that has an excellent effect of adjusting the texture of the skin.
○: The total score is 25 or more and less than 35, or the total score is 35 or more and the number of panelists determined to be 0 is 1 or more and 2 or less. : It is an external preparation for skin having an excellent effect of adjusting skin texture.
Δ: The total score is 15 points or more and less than 25 points. : An external preparation for skin that has a slight effect of adjusting skin texture.
X: The total score is less than 15 points. : An external preparation for skin that does not have the effect of adjusting the texture of the skin.

(5) Porphyrin production inhibitory effect (porphyrin reduction rate)
Twenty women (30 to 48 years old) were used as the panelists, and after each panel was washed, 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 a cosmetic full face photographing device (Facical Stage DM-3, manufactured by Schott Moritex Co., Ltd.). The state of porphyrin was evaluated. Porphyrin-derived fluorescence (number of red fluorescent spots) was measured by an image analysis method, and the porphyrin reduction rate was calculated from the following equation. In addition, the porphyrin reduction rate in Table 1 and Table 2 is an average value of 20 panelists.

Porphyrin reduction rate (%) = (1−number of red fluorescent points after continuous application of skin external preparation for 4 weeks / number of red fluorescent points before start of use of external preparation for skin) × 100
A: Porphyrin reduction rate of 30% or more: An external preparation for skin having a very excellent porphyrin production inhibitory effect.
○: Porphyrin reduction rate of 15% or more and less than 30%: It is an external preparation for skin having an excellent porphyrin production inhibitory effect.
(Triangle | delta): Porphyrin reduction rate 6% or more and less than 15%: It is a skin external preparation which has a porphyrin production suppression effect slightly.
X: Porphyrin reduction rate of less than 6%: It is an external preparation for skin having no porphyrin production inhibitory 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 density | concentration of "CyPA-ET" 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. The numerical value of (Product) in the table represents the concentration of “CyPA-PW” as 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. The numerical value of (Product) in the table represents the concentration of “CyPA-PW” as a product.

From the results of Examples 1 to 6 shown in Table 1, 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 is excellent and the effect of suppressing porphyrin production 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 durability of the moisturizing effect and the effect of improving wrinkles are only slightly obtained, and the conformability to the skin is poor. And the effect of adjusting skin texture and the effect of suppressing porphyrin production are not obtained.
In Comparative Example 2, since the component (a) is not included, the familiarity to the skin is recognized, but the porphyrin production inhibitory effect is only slightly obtained, the durability of the moisturizing effect, the wrinkle improving effect, the skin The effect of adjusting the texture is not obtained.
In Comparative Example 3, since the component (b) is not included, only a slight degree of familiarity with the skin, durability of the moisturizing effect, wrinkle improvement effect, skin texture adjustment effect, and porphyrin production suppression effect are obtained. .
In Comparative Example 4, since the component (c) is not included, the familiarity to the skin, the persistence of the moisturizing effect, and the wrinkle improving effect are recognized, but the effect of adjusting the texture of the skin and the effect of suppressing porphyrin production are only slight. Not obtained.
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 adjusting the texture and the effect of suppressing porphyrin production are only slightly 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 skin external preparation, five items were evaluated in the same manner 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. The numerical value of (Product) in the table represents the concentration of “CyPA-PW” as a product.
2) “Eco Garm” manufactured by Dainippon Pharmaceutical Co., Ltd.
3) “Carbopol 940” manufactured by BF-Goodrich

  From the results of Example 7 shown in Table 3, the emulsion according to the external preparation for skin of the present invention has good conformability to the skin, excellent moisturizing effect, wrinkle improving effect, and effect of adjusting skin texture, It can be understood that the porphyrin production inhibitory effect 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 skin external preparation, five items were evaluated in the same manner 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. The numerical value of (Product) in the table represents the concentration of “CyPA-PW” as a product.

  From the results of Example 8 shown in Table 4, the cream according to the external preparation for skin of the present invention has good compatibility with the skin, has excellent moisturizing effect, wrinkle improvement effect, and excellent skin texture effect, It can be understood that the porphyrin production inhibitory effect 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) 0.01-5 mass% of polyoxyethylene sorbitan fatty acid ester or polyoxyethylene hydrogenated castor oil
Contains a topical skin preparation.

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