JPH0848625A - Sebum secretion inhibitor - Google Patents

Abstract

(57) [Summary] [Purpose] To provide a sebum secretion inhibitor which suppresses the secretion of sebum in the skin and scalp continuously and locally and has no side effects and which is good in safety. [Structure] The number of carbon atoms represented by the following general formula [Chemical formula 1] is 6 to
20. A sebum secretion inhibitor, which comprises as an active ingredient at least one selected from the group consisting of carboxylic acid of 20 and salts, ester derivatives and amide derivatives thereof. Embedded image

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention has a persistent and topical sebum secretion inhibitory effect on the skin, and is a cosmetic, pack, external preparation for skin, shampoo, hair tonic, hair-growth / hair-growth cosmetic. And a sebum secretion inhibitor that can be added to

[0002]

2. Description of the Related Art Sebum secreted by the sebaceous glands of the skin and scalp keeps the skin soft and smooth, and supplies necessary and appropriate oil to the hair in order to maintain its suppleness and beauty. is necessary. In addition, sebum plays an important role in preventing various irritants from outside the body from mixing in from the skin and the surface of the scalp, while preventing the loss of water from the skin and the stratum corneum of the scalp.

However, if the activity of the sebaceous glands is excessively increased and the secretion of sebum increases too much, it may cause dermatitis such as acne and seborrheic skin diseases, and increase dandruff in the scalp and seborrheic skin. May cause flames and accompanying hair loss. In addition, excessive sebum causes a cosmetically unfavorable condition (hair and skin become oily) on the skin and scalp, and promotes the growth of microorganisms and pathogenic bacteria to cause various skin troubles.

[0004] For the purpose of improving or preventing such dermatitis, skin troubles, and cosmetic problems caused by excessive secretion of sebum, sebum has conventionally been removed by washing with soap or the like. Attempts have been made to use sebum secretion inhibitors in order to suppress the increase in skin inflammation. As the sebum secretion inhibitor, an antiandrogen agent is known. The anti-androgen agent inhibits either or both of the activity of the 5α-reductase enzyme involved in the reduction of testosterone from dihydrotestosterone and the binding of dihydrotestosterone with the receptor. Other sebum secretion inhibitors include vitamin A acid,
Royal jelly extract, royal jelly acid and the like are known.

[0005]

However, the effect of removing excess sebum by washing the skin or scalp with the above-mentioned soap or the like is temporary, and it is possible to suppress the excess secretion of sebum and There is a problem that dermatitis, skin troubles, etc. due to excessive secretion of sebum cannot be improved.

On the other hand, the anti-androgen is a substance involved in hormone metabolism, and the vitamin A acid also has a hormone-like action. Since these act on organs other than the sebaceous glands, there is a problem that systemic side effects are larger than local effects.

The royal jelly acid is known as a sebum secretion inhibitory active ingredient of royal jelly extract ( Nippon Kaihatsu, 98 (4) , 469-475, 198 ) .
8) However, the royal jelly acid is a trace component and it is difficult to mix it in a high concentration as a sebum secretion inhibitor to the extent that it effectively exhibits a sebum secretion inhibitory effect. On the other hand, a method for obtaining royal jelly acid itself by synthesis has been proposed (JP-A-54-88216), but in this method, the yield is poor and the isomer of the double bond site is formed, so that the royal jelly acid having high purity is produced. Is difficult to produce industrially at low cost. Further, royal jelly acid has a double bond in the molecule and thus has a problem in stability. In addition, other compounds have a problem that they are insufficient in safety and effect.

[0008] Therefore, an object of the present invention is to provide a sebum secretion inhibitor which suppresses the secretion of sebum in the skin and scalp continuously and locally and has no side effects and which is excellent in safety.

[0009]

Means for Solving the Problems As a result of intensive studies, the present inventors have found that a sebum secretion inhibitor containing a specific compound as an active ingredient can achieve the above object.

The present invention was made on the basis of the above findings, and has the following general formula [Chemical formula 2] (the same as the above [Chemical formula 1]).
A sebaceous secretion inhibitor characterized by containing as an active ingredient at least one selected from the group consisting of carboxylic acids having 6 to 20 carbon atoms represented by and their salts, ester derivatives and amide derivatives. It is provided.

[0011]

Embedded image

The sebum secretion inhibitor of the present invention will be described in detail below. The active ingredient in the sebum secretion inhibitor of the present invention is at least selected from the group consisting of carboxylic acids having 6 to 20 carbon atoms represented by the general formula [Chemical Formula 2], and salts, ester derivatives and amide derivatives thereof. It is one kind.

Examples of the carboxylic acid salts include alkali metal salts and alkaline earth metal salts such as sodium salts, potassium salts and calcium salts; ammonium salts; alkylamine salts such as triethylamine salts; triethanolamine salts,
One or more selected from the group consisting of alkanolamine salts such as triisopropanolamine salts; amino acid salts such as lysine salts and arginine salts; guanidine salts; and sugar amine salts such as glucosamine salts, among which ammonium can be mentioned. Particularly preferred is one or more selected from the group consisting of salts, alkanolamine salts and amino acid salts. As the salt of the carboxylic acid, a salt prepared in advance by a known method can be used, or a salt produced when the carboxylic acid is blended in a cosmetic or the like described later may be used as it is.

Examples of the ester derivative of carboxylic acid include alkyl esters such as methyl and ethyl, branched alkyl esters such as 2-ethylhexyl, aryl esters containing an aromatic ring such as benzyl, glycerin, propylene glycol and polyethylene glycol. And one or more kinds selected from the group consisting of esters with polyhydric alcohols.

The amide derivative of the above-mentioned carboxylic acid is an amide obtained by reaction with ammonia;
Alkylamides obtained by reaction with methylamine, ethylamine, propylamine, etc .; Alkylamides substituted by hydroxy groups obtained by reaction with monoethanolamine, diethanolamine, etc .;
And one or more selected from the group consisting of amides obtained by reaction with amino acids such as glycine and phenylalanine.

As Y in the general formula [Chemical Formula 2], a linear alkyl group in which a hydroxyl group is substituted at the ω-6 position from the terminal (ω position) is preferable. N is 7 to 10
Is preferred.

As a specific combination of Y and n,
The total number of carbon atoms of the carboxylic acid may be 6 to 20, but n
= 7, Y is a 1-hydroxypropyl group, n =
When Y is 8, Y is a hydroxymethyl group, 1-hydroxyethyl group, 1-hydroxy-1-methylethyl group, n
= 9, Y is a hydroxymethyl group, and when n = 10, Y is preferably a hydroxymethyl group or 1-hydroxyheptyl group. Particularly, when n = 8, Y is 1-hydroxy. Ethyl group, Y when n = 9
Is more preferably a hydroxymethyl group.

Examples of the compound represented by the general formula [Chemical Formula 2] include 6-hydroxyhexanoic acid (6-Hydroxyh
exanoic acid), 8-hydroxyoctanoic acid (8-Hydrox
yoctanoic acid), 9-hydroxynonanoic acid (9-Hydrox
ynonanoic acid), 10-hydroxydecanoic acid (10-Hyd
roxydecanoic acid), 10,11-dihydroxyundecanoic acid (10,11-Dihydroxyundecanoic acid), 9-hydroxyundecanoic acid (9-Hydroxyundecanoic acid),
10-Hydroxyundecanoic
acid), sodium 10-hydroxyundecanoate (So
dium 10-Hydroxyundecanoate), 10-hydroxy-1
0-Methylundecanoic acid (10-Hydroxy-10-methylundeca
noic acid), 11-hydroxyundecanoic acid (11-Hyd
roxyundecanoic acid), sodium 11-hydroxyundecanoate (Sodium 11-hydroxyundecanoate), 11
-Hydroxyundecanami (11-Hydroxyundecanami
de), ethyl 11-hydroxyundecanoate (Ethyl 11
-hydroxyundecanoate), 12-Hydroxydodecanoic acid (12-Hydroxydodecanoic acid), 13-Hydroxytridecanoic acid (13-Hydroxytridecanoic acid), 14-Hydroxytetradecanoic acid (14-Hydroxytetradecanoic ac)
id), N- (2-Hydroxyethyl) -11-hydroxyun
decanamide], N- (11-hydroxyundecanoyl) -glycine [N- (11-hydroxyundecanoyl) glycine],
9-hydroxyundecanoic acid triisopropanolamine (Triisopropanolamine 9-hydroxyundecanoate), 9
-Hydroxyundecanoic acid arginine salt (Arginine 9-
10-hydroxyundecanoate Triethanolamine 10-hydroxyun
decanoate), 10-hydroxyundecanoic acid triisopropanolamine (Triisopropanolamine 10-hydroxyu)
ndecanoate), 10-hydroxyundecanoic acid arginine salt (Arginine 10-hydroxyundecanoate), 10-hydroxyundecanoic acid ammonium (Ammonium 10-hydrox
yundecanoate), Triethanolamine 11-hydroxyundecano
ate), 11-hydroxyundecanoic acid triisopropanolamine (Triisopropanolamine 11-hydroxyundecan)
oate), 11-hydroxyundecanoic acid arginine salt (Arginine 11-hydroxyundecanoate), 11-hydroxyundecanoic acid ammonium (Ammonium 11-hydroxyund)
ecanoate) 12-hydroxydodecanoate triethanolamine (Triethanolamine 12-hydroxydodecanoate), 1
2-hydroxystearic aci
d), Triisopropanolamine 12-hydroxystearat
e), 12-hydroxystearic acid arginine salt (Arg
inine 12-hydroxystearate), etc.,
A commercially available product can be used as it is. The compounds can be used alone or in combination of two or more.

In the sebum secretion inhibitor of the present invention, the compound represented by the general formula [Chemical Formula 2] may be used alone as an active ingredient, but if necessary, the compound of the present invention may be used as a main component. Surfactants, oils, moisturizers, astringents, cooling agents, antioxidants, alcohols, chelating agents, pH adjusters, preservatives, thickeners, pigments, fragrances, as long as the effect is not impaired.
In addition to anti-inflammatory agents, keratolytic agents, antibacterial agents, bactericidal agents, and other medicinal agents, known ingredients generally used in pharmaceuticals, cosmetics, quasi-drugs, and the like can be appropriately mixed. On this occasion,
The above-mentioned active ingredient in the sebum secretion inhibitor of the present invention has a compounding amount of usually 0.0
5 to 20 weight percent (hereinafter, simply referred to as "%"),
It is desirable that the content is preferably 0.1% to 10%.

The sebum secretion inhibitor of the present invention can be usually used by blending it with various cosmetics such as external skin cosmetics, hair-growth and hair-growth cosmetics. At this time, the dosage form of the external skin cosmetics and the hair-growth / hair-growth cosmetics may be liquid, emulsion, ointment, cream, lotion, gel, aerosol, or the like. For example, W / O type emulsified cosmetics, O / W type emulsified cosmetics, creams, cosmetic emulsions, lotions, oily cosmetics, packs, foundations, hair tonics, shampoos and the like can be used.

[0021]

The present invention will be described in more detail with reference to examples, but the present invention is not limited thereto.

[0022]

Example 1 The following test was conducted to evaluate the sebum synthesis inhibitory activity of the sebum secretion inhibitor of the present invention. The method for measuring sebum synthesis is
The method was performed according to the method of Hall et al. (See Arch Dermatol Res. 275: 1-7. 1983). That is, skin tissue (diameter 3 mm) containing the sebaceous glands of the auricle of a male hamster was cultured in Krebes-Ringer phosphate buffer containing radioactive sodium acetate for 3 hours, and the obtained tissue was hydrolyzed and extracted with hexane. Then, the amount of radiolabeled lipid in the hexane fraction was measured with a liquid scintillation counter to determine the amount of synthetic sebum in the sebaceous glands. At this time, the skin tissue obtained from the left auricle of the same hamster was in Krebes-Ringer phosphate buffer, while the skin tissue obtained from the right auricle contained a sebum secretion inhibitor shown in [Table 1] at a concentration of 100 μM. Krebes-Ringer
The experiment was conducted in a phosphate buffer, and the sebum synthesis inhibition rate was calculated by the following formula. The results are shown in [Table 1]. The sebum synthesis inhibition rate of each compound is the average value of 6 animals.

Sebum synthesis inhibition rate (%) = 100-(sebum synthesis amount in the presence of inhibitor / sebum synthesis amount in the absence of inhibitor) × 100

[0024]

[Table 1]

As is clear from the results shown in [Table 1],
It is understood that the sebum secretion inhibitor of the present invention shows a high sebum synthesis inhibitory activity at a concentration of 100 μM, and has an excellent sebum synthesis inhibitory effect.

[0026]

Example 2 The following test was carried out to evaluate the sebum synthesis inhibitory activity of the sebum secretion inhibitor of the present invention. Male hamsters aged 5 to 6 weeks were divided into 6 groups, and then an ethanol solution containing 10% by weight of the known sebum secretion inhibitor (royal jelly acid) and the sebum secretion inhibitor of the present invention shown in Table 2 was added. An ethanol solution containing no sebum secretion inhibitor was applied to the right auricle of each animal once a day to the left auricle of the same hamster. 5 per week
After application for 2 weeks, the auricle of the hamster was excised, the skin tissue containing sebaceous glands with a diameter of 3 mm was taken out from the center of the left and right auricle, and the amount of sebum synthesis was measured by the same method as in Example 1. The sebum synthesis amount obtained was introduced into the following formula to determine the sebum synthesis inhibition rate. The results are shown in [Table 2]. The value of the sebum synthesis inhibition rate in each group is the average of 6 animals. Sebum synthesis inhibition rate (%) = 100− (sebum synthesis amount on ethanol solution application side containing inhibitor / sebum synthesis amount on ethanol solution application side without inhibitor) × 100

[0027]

[Table 2]

As is clear from the results shown in [Table 2],
It can be seen that when the sebum secretion inhibitor of the present invention is applied to the sebaceous glands of animals, it suppresses the sebum synthesis ability in the sebaceous gland tissue. It was also found that the sebum secretion inhibitor of the present invention has a higher sebum synthesis inhibitory effect than royal jelly acid, which is a known sebum secretion inhibitor.

As described above, the sebum secretion inhibitor of the present invention is
It has an unprecedented sebum secretion inhibitory effect and is highly safe even if it is continuously applied externally for a long period of time.

[0030]

Example 3 Ingredients shown in [Table 3] to [Table 8] are blended, and sebum-secretion-suppressing lotion [Table 3], sebum-secretion-preventing emollient cream [Table 4], sebum-secretion-suppressing pack [Table 5] ], An anti-dandruff hair tonic [Table 6], an anti-dandruff shampoo [Table 7], and an anti-dandruff rinse [Table 8] were produced by a conventional method. All of them showed excellent stability.

[0031]

[Table 3]

[0032]

[Table 4]

[0033]

[Table 5]

[0034]

[Table 6]

[0035]

[Table 7]

[0036]

[Table 8]

[0037]

EFFECTS OF THE INVENTION The sebum secretion inhibitor of the present invention suppresses the secretion of sebum in the skin and scalp continuously and locally, and has no side effect and is highly safe. And, the sebum secretion inhibitor of the present invention has almost no irritation to the skin or scalp, and has no hormone-like action, so no systemic side effects are observed and it is safe to use externally for a long period of time. There is no problem with sex.

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Claims (4)

[Claims] 1. An active ingredient comprising at least one selected from the group consisting of carboxylic acids having 6 to 20 carbon atoms represented by the following general formula [Chemical Formula 1], and salts, ester derivatives and amide derivatives thereof. An agent for suppressing sebum secretion, which comprises: Embedded image 2. The carboxylic acid salt selected from the group consisting of alkali metal salts, alkaline earth metal salts, ammonium salts, alkylamine salts, alkanolamine salts, amino acid salts, guanidine salts and sugar amine salts. The sebaceous secretion inhibitor according to claim 1, which is one or more kinds. 3. The sebum secretion inhibitor according to claim 1, wherein the carboxylic acid salt is one or more selected from the group consisting of ammonium salts, alkanolamine salts and amino acid salts. 4. The sebum secretion inhibitor according to claim 1, wherein the ester derivative of carboxylic acid is one or more selected from the group consisting of alkyl ester, branched alkyl ester, aryl ester and polyhydric alcohol ester.