JPH06192032A - Sebum-secretion suppressing agent - 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] Sebum secretion characterized by containing at least one selected from the group consisting of a carboxylic acid represented by the following general formula [Formula 1] or a salt thereof, and an ester derivative and an amide derivative thereof as an active ingredient. Inhibitor. [Chemical 1]

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 has been made based on the above findings, and is at least selected from the group consisting of carboxylic acids represented by the following general formula [Chemical Formula 2] or salts thereof, and ester derivatives and amide derivatives thereof. It is intended to provide a sebum secretion inhibitor characterized by containing one kind as an active ingredient.

[0011]

[Chemical 2]

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 one selected from the group consisting of the carboxylic acid represented by the general formula [Chemical Formula 2] or a salt thereof, and an ester derivative and an amide derivative thereof. Here, examples of X in the general formula [Chemical Formula 2] include a hydrogen atom or a metal ion such as calcium, sodium, potassium, magnesium, aluminum, or zinc.

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. Examples thereof include esters with polyhydric alcohols. As the amide derivative of the carboxylic acid, an amide obtained by a reaction with ammonia; an alkylamide obtained by a reaction with methylamine, ethylamine, propylamine, etc .; a reaction with monoethanolamine, diethanolamine, etc. Alkyl amides substituted by a hydroxy group; amides obtained by reaction with amino acids such as glycine and phenylalanine.

Y in the general formula [Chemical formula 2] is
The carbon number thereof is preferably 1 to 5, and specific examples thereof include hydroxymethyl, 2-hydroxyethyl, 1-hydroxyethyl, 1,2-dihydroxyethyl and 1-hydroxy-1-methylethyl. Can be mentioned.

As the compound represented by the general formula [Chemical Formula 2], n is 7 to 9, further n is 8 and Y is 2-
Hydroxyethyl group, 1-2-dihydroxyethyl group,
Particularly preferred are carboxylic acids, salts thereof, ester derivatives and amide derivatives thereof, which are 1-hydroxyethyl groups and 1-hydroxy-1-methylethyl groups.

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-
Hydroxyundecanoic acid (10-Hydroxyundecanoic acid
) 10-Hydroxy-10-methylundecanoic acid (1
0-Hydroxy-10-methylundecanoic acid), 11-hydroxyundecanoic acid (11-Hydroxyundecanoic acid),
Sodium 11-hydroxyundecanoate
hydroxyundecanate), 11-hydroxyundecanoate (11-Hydroxyundecanamide), ethyl 11-hydroxyundecanoate (Ethyl 11-hydroxyundecanoate), 1
2-Hydroxydodecanoic aci
d), 13-hydroxytridecanoic acid (13-Hydroxytrid
ecanoic acid), 14-hydroxytetradecanoic acid (12
-Hydroxytetradecanoic acid), N- (2-hydroxyethyl) -11-hydroxyundecane amide [N- (2-Hy
droxyethyl) -11-hydroxyundecanamide], N- (11-
Hydroxy undecanoyl) -glycine [N- (11-hydroxy
undecanoyl) glycine] and the like, and commercially available products can be used as they are. The compounds can be used alone or in combination of two or more.

The sebum secretion inhibitor of the present invention preferably contains, as an active ingredient, a compound represented by the general formula [Chem. 2] as a main component, and the compound may be used alone, but if necessary, Within the range that does not impair the effects of the present invention, surfactants, oils, moisturizers, astringents, cooling agents, antioxidants, alcohols, chelating agents, pH adjusters, preservatives, thickeners, dyes. In addition to fragrances and fragrances and medicinal agents such as anti-inflammatory agents, keratolytic agents, antibacterial agents, bactericides and the like, well-known ingredients generally used in pharmaceuticals, cosmetics, quasi drugs and the like can be appropriately mixed. At this time, the compounding amount of the active ingredient of the sebum secretion inhibitor of the present invention is usually,
It is 0.05 to 20 weight percent (hereinafter, simply indicated by "%"), and preferably 0.1% to 10%.

The sebum secretion inhibitor of the present invention can be usually used by blending with external skin cosmetics, hair nourishing / hair-growth cosmetics and the like. At this time, the dosage forms of the external cosmetic for skin and the hair-growth / hair-growth cosmetic are liquid, emulsion, ointment, cream,
Lotion, gel, aerosol, etc. are optional, for example, W /
It can be an O-type emulsified cosmetic, an O / W-type emulsified cosmetic, a cream, a cosmetic emulsion, a lotion, an oil-based cosmetic, a pack, a foundation, a hair nick, a shampoo and the like.

[0019]

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

[0020]

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 was Krebes-containing the sebum secretion inhibitor shown in Table 1 at a concentration of 100 μM. An experiment was conducted in Ringer 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

[0022]

[Table 1]

As is clear from the results shown in Table 1, 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.

[0024]

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

[0025]

[Table 2]

As is clear from the results shown in Table 2, when the sebum secretion inhibitor of the present invention was applied to the sebaceous glands of animals,
It is found that the sebum synthesis ability in the sebaceous gland tissue is suppressed. 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.

[0028]

[Example 3] The ingredients shown in Tables 3 to 9 were blended, and sebum-secretion-suppressing lotion (Table 3), sebum-secretion-suppressing emollient cream (Table 4), sebum-secretion-suppressing pack (Table 5), and anti-dandruff hair were prepared. Tonic (Table 6), anti-dandruff shampoo (Table 7) and anti-dandruff rinse (Table 8) were produced by a conventional method.
All of them showed excellent stability.

[0029]

[Table 3]

[0030]

[Table 4]

[0031]

[Table 5]

[0032]

[Table 6]

[0033]

[Table 7]

[0034]

[Table 8]

[0035]

INDUSTRIAL APPLICABILITY According to the present invention, there is provided a sebum secretion inhibitor which suppresses the secretion of sebum in the skin and scalp continuously and locally, and has no side effects and good safety. 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.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁵ Identification number Reference number in the agency FI Technical indication location A61K 31/20 9283-4C (72) Inventor Kimihiko Hori 1348-2 Esojima-cho, Utsunomiya-shi, Tochigi Prefecture (72) ) Inventor Akira Sakaguchi 4-15-11 Fujimigaoka, Utsunomiya City, Tochigi Prefecture (72) Inventor Yasuto Suzuki 2166 Kamamomo, Kamimikawa Town, Kawachi District, Tochigi Prefecture (72) Inventor Shinya Amano 2606 Akabane, Kai Town, Haga District, Tochigi Prefecture 6

Claims (1)

[Claims] 1. A carboxylic acid represented by the following general formula [Chemical Formula 1] or a salt thereof, and at least one selected from the group consisting of ester derivatives and amide derivatives thereof as an active ingredient. Sebum secretion inhibitor. [Chemical 1]