JP2005035929A - Antimicrobial agent and antimicrobial product using the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To obtain an antimicrobial agent useful for various uses for controlling reproduction of a dandruff causative being an indigenous fungus in the skin, especially an antimicrobial agent suitable for a safe hair cosmetic having prevention effect on dandruff development and a hair cosmetic containing the antimicrobial agent and having a pleasant aroma. <P>SOLUTION: The antimicrobial agent comprises a γ-lactone represented by the general formula (R is a 1-11C alkyl group; the broken lines are each a single bond or a double bond present in either one of the broken-line positions) as an active ingredient. <P>COPYRIGHT: (C)2005,JPO&NCIPI

Description

  The present invention relates to a prophylactic or therapeutic agent for dandruff, which suppresses dandruff by suppressing the growth of skin resident fungi, and a cosmetic for hair containing the same.

  The scalp is inhabited with normal skin bacteria that exist in normal skin, such as Acne gonorrhoeae that causes acne. Similarly, a dandruff-causing fungus, Malassezia furfur, is also inhabited. The occurrence of dandruff is largely related to the resident skin fungus that likes fat, and the scalp, which has a large amount of sebaceous glands and a large amount of sebum, is an excellent place to live and grow. Dandruff is a substance that has been exfoliated due to metabolism, and is physiologically generated by anyone. However, when the amount of dandruff is abnormally high, it is called dandruff. If left untreated, it may be itchy, it may be scratched with nails, and the scalp may be inflamed. In addition, dandruff has dryness and sticky wetness, and generally, many dandruffs are considered to have excessive wetness of sebum secretion. Many of these are considered to be predecessor or mild forms of seborrheic dermatitis and are said to occur more often in men than in women. Thus, it is known that a dandruff-causing bacterium, Malassezia furfur, grows and increases in activity on the scalp with a lot of sebum, thereby deteriorating dandruff and itching. Furthermore, the occurrence of dandruff is also known as a cause of hair loss.

  Conventionally, it is effective to wash the hair with a shampoo containing antibacterial and bacteriostatic zinc pyrithione, octopirox, piroctone olamine, etc. as a countermeasure. However, zinc pyrithione has been reported by the National Institute for Environmental Studies as being suspected of being an environmental hormone, and future trends are drawing attention.

  In order to solve the above problems, some antibacterial agents using natural extracts have been proposed. For example, in Patent Document 1, an antibacterial composition containing a ginkgo endoderm extract as an active ingredient is included, and in Patent Document 2, one or more of the Orchidaceae genus Ebine or Ganzekilan is included as an active ingredient. According to Patent Document 3, the anti-dandruff effect, the blood circulation promoting effect, the antipruritic effect, and the hair growth effect on the scalp are obtained by ashing seaweed raw materials, for example, brown algae such as seaweed, kombu and honda walla. Anti-dandruff agent containing seaweed ash or extract thereof as an active ingredient, and further, in Patent Document 4, a coumarin analog mixture obtained from the peel of citrus fruit, particularly a coumarin analog mixture obtained from citrus cold press oil An antibacterial agent containing as an active ingredient has been proposed.

  However, these naturally-derived antibacterial agents have problems such as affecting the scent of the target to be added.

On the other hand, it has been reported in Patent Documents 5 and 6 that some lactones exhibit growth inhibitory activity against specific Gram-positive bacteria. However, the dandruff-causing fungus, Malassezia fluflu ( No antimicrobial activity against Malassezia furfur) has been proposed. In addition, although fragrance compounds are used for the purpose of giving a pleasant scent to hair washing cosmetics, hair restorers, hair finishing cosmetics, permanent waving agents, hair dyes and hair bleaches, these compounds can be used against skin resident fungi. There is no mention of antibacterial properties.
Japanese Patent Laid-Open No. 10-27316 Japanese Patent Laid-Open No. 11-279033 JP 2000-344678 A JP 2002-275007 A Japanese Patent Application No. 2003-123893 Japanese Patent Application No. 2003-139466

  An object of the present invention is to provide an antibacterial agent that can be used in various applications for suppressing the growth of dandruff-causing fungi that are skin resident fungi, and particularly suitable for safe hair cosmetics that are effective in preventing the occurrence of dandruff. It is to provide.

  Another object of the present invention is to provide a cosmetic for hair having a pleasant fragrance containing the antibacterial agent.

  As a result of intensive studies to solve the above-mentioned problems, the present inventors have demonstrated that specific γ-lactones, which are lactone-based synthetic fragrances, exhibit antibacterial properties against skin resident fungi among fragrance compounds. As a result, the present invention was reached.

  That is, the present invention achieves the above object, and has the following general formula:

（式中、Ｒは炭素数１〜１１のアルキル基を示し、破線は単結合もしくはいずれか一方が二重結合であることを示す）で示されるγ−ラクトン類を有効成分とする、抗真菌剤またはふけ症の予防剤または治療剤である。

(Wherein R represents an alkyl group having 1 to 11 carbon atoms, and the broken line represents a single bond or one of them is a double bond), and an antifungal comprising an γ-lactone as an active ingredient It is an agent or an agent for preventing or treating dandruff.

  More preferably, 4-pentanolide, 4-hexanolide, 4-heptanolide, 4-octanolide, 4-nonanolide, 4-decanolide, 4-undecanolide, 4-dodecanolide, 4-tridecanolide, 4-tetradecanolide, 4-pentadecanolide, 5- An antifungal agent or a prophylactic or therapeutic agent for dandruff comprising at least one selected from methyl-2 (3H) -furanone and 5-methyl-2 (5H) -furanone as an active ingredient.

  Furthermore, the other aspect of this invention is the cosmetics for hair formed by mix | blending the said antifungal agent, the preventive agent or therapeutic agent of a dandruff.

  The γ-lactones of the present invention obtained an excellent antibacterial action against dandruff-causing bacteria. By blending these γ-lactones, it is possible to obtain hair cosmetics and the like that suppress dandruff and itch caused by dandruff.

  The present invention includes the following general formula of the present invention:

（式中、Ｒは炭素数１〜１１のアルキル基を示し、破線は単結合もしくはいずれか一方が二重結合であることを示す）で示されるγ−ラクトン類を有効成分として含有するふけ症の予防剤または治療剤である。本発明のラクトン類は、皮膚常在真菌である、ふけ原因菌のマラセチア属フルフル（Ｍａｌａｓｓｅｚｉａ ｆｕｒｆｕｒ）に対して強い抗菌性を示し、これらの菌の増殖を抑制することによりふけの発生を抑えるものである。しかも、本発明で用いられる選択された上記一般式で示されるγ−ラクトン類は、ふけの発生を抑えることから、抜け毛予防も期待できる。

(Wherein R represents an alkyl group having 1 to 11 carbon atoms, and the broken line represents a single bond or one of them is a double bond). It is a preventive or therapeutic agent. The lactones of the present invention exhibit strong antibacterial activity against the dandruff-causing fungus, Malassezia furfur, which suppresses the occurrence of dandruff by suppressing the growth of these fungi. It is. Moreover, since the selected γ-lactones represented by the above general formula used in the present invention suppress the occurrence of dandruff, hair loss prevention can also be expected.

  Examples of γ-lactones in the present invention include 4-pentanolide, 4-hexanolide, 4-heptanolide, 4-octanolide, 4-nonanolide, 4-decanolide, 4-undecanolide, 4-dodecanolide, 4-tridecanolide, 4-tetradecanolide, Examples include 4-pentadecanolide, 5-methyl-2 (3H) -furanone, and 5-methyl-2 (5H) -furanone.

  These γ-lactones are preferably used because they are commercially available as perfume compounds and are extremely easy to obtain.

  Furthermore, since γ-lactones used in the present invention have good biodegradability and no toxicity, they are not adversely affected even when released into the environment, and are safe for the human body. is there.

  As the γ-lactones in the present invention, commercially available products can be used. Moreover, the manufacturing method of these compounds is established, and it can also synthesize | combine according to a well-known method.

  The antifungal agent of the present invention is preferably used in cosmetics for hair because it acts on skin resident fungi and exhibits the ability to suppress the growth of dandruff-causing bacteria. Examples of the cosmetics for hair of the present invention include cosmetics for washing hair, hair growth agents, cosmetic agents for hair finishing, permanent wave agents, hair dyes, and hair bleaches. More specifically, shampoos, rinses, conditioners, rinse-in shampoos, treatments and the like are mentioned as cosmetics for washing hair. The cosmetics for hair finishing include hair foam, hair mousse, hair spray, hair mist, hair gel, water grease, set lotion, color lotion, hair liquid, pomade, tics, hair cream, hair blow, split hair coat, hair oil, hair Examples of tonics and hair dyes include color sticks, color sprays, liquid types, gel types, and oxidative hair dyes. The amount of these hair washing cosmetics, hair restorer, hair finish cosmetic agent, permanent wave agent, hair dye, and hair bleach may vary depending on the type of product and the purpose of use, etc. It is 0.01-5 mass%, More preferably, it is 0.025-1 mass%.

  In addition, the antifungal agent of the present invention can be blended with synthetic resin molded products such as shower caps and hair bands, antibacterial fibers, antibacterial paper, and coloring materials to obtain antibacterial products.

  Further, the antifungal agent of the present invention is an active ingredient such as another antibacterial agent, bactericidal agent, analgesic anti-inflammatory agent, cooling agent, etc., surfactant, thickener, pigment, and the like within the range not impairing the effects of the present invention. It can be used in combination with auxiliary ingredients such as perfumes and alcohol.

  Next, the present invention will be described based on test examples and examples.

(Test Example 1)
The antifungal test was conducted using the following (a) fragrance compound, (b) one strain and (c) one medium.
(A) Perfume compound:
4-Pentanolide, 4-hexanolide, 4-heptanolide, 4-octanolide, 4-nonanolide, 4-decanolide, 4-undecanolide, 4-dodecanolide, 4-tridecanolide, 4-tetradecanolide, 4-pentadecanolide (b)
Malassezia fluflu NBRC 0656 (Malassezia furfur)
(Obtained from Biological Resource Center)
(C) Medium used:
Biological Genetic Resource Center (NBRC) Restoration Culture Medium 103

In a 500 ml Erlenmeyer flask, 100 ml of the above medium is put, and the bacterial cell suspension is inoculated so as to be 10 ⁵ CFU / ml, and added therein so that the concentration of each fragrance compound is 250 ppm. After making the vent plug, culturing at 28 ° C. for 48 hours and reciprocal shaking at 80 rpm was performed, and the turbidity (absorbance at 660 nm) of the culture solution was measured. As a result, as shown in Table 1, all of the tested γ-lactones showed a strong growth inhibitory effect.

(Test Example 2)
The antifungal test was conducted using the following (a) fragrance compound, (b) one strain and (c) one medium.
(A) Perfume compound:
-Strain using 5-methyl-2 (3H) -furanone (b):
Malassezia fluflu NBRC 0656 (Malassezia furfur)
(Obtained from Biological Resource Center)
(C) Medium used:
Biological Genetic Resource Center (NBRC) Restoration Culture Medium 103

Put 100 ml of the above medium in a 500 ml Erlenmeyer flask, inoculate the cell suspension to 10 ⁵ CFU / ml, add the fragrance compound concentration to 250 ppm therein, and ventilate the silicon After stoppering, reciprocal shaking culture was performed at 28 ° C. for 48 hours at 80 rpm, and the turbidity (absorbance at 660 nm) of the culture solution was measured. As a result, as shown in Table 2, a strong growth inhibitory effect was observed on the tested 5-methyl-2 (3H) -furanone.

Transparent shampoo 1). Laurylpolyethylene (3) Sulfate sodium salt (30% aqueous solution) 30.0 (mass%)
2). Lauryl sulfate sodium salt (30% aqueous solution) 10.0
3). Palm oil fatty acid diethanolamide 4.0
4). Glycerin 1.0
5). 4-Undecanolide 0.025
6). Fragrance 0.375
7). Dye 0.01
8). Metal ion sequestering agent, pH adjuster 0.01
9). Purified water 54.58
Production method: (1) to (8) are sequentially added to (9) and uniformly mixed and dissolved.

Rinse 1). Silicone oil 3.0 (mass%)
2). Liquid paraffin 1.0
3). Cetyl alcohol 1.5
4). Stearyl alcohol 1.0
5). Stearyltrimethylammonium chloride 0.7
6). Glycerin 3.0
7). 4-Undecanolide 0.025
8). Fragrance 0.375
9). Dye 0.01
10). Purified water 89.39
Production method: (1) to (9) are sequentially added to (10) and uniformly mixed and dissolved.

  A formulation not containing 4-undecanolide in the formulations of Example 1 and Example 2 was prepared and used as Comparative Example 1 and Comparative Example 2.

Antidandruff evaluation and itch suppression evaluation Using Example 1, Example 2, Comparative Example 1, and Comparative Example 2, a group of 10 adult males with dandruff and itch associated with dandruff, usually for one month every morning We had you use instead of shampoo and rinse which we used and performed dandruff control and itch control test. The evaluation criteria are as shown below, and the number of people who answered each evaluation is shown in Table 3.

Anti-dandruff effect and itching suppression effect Effective: Suppressed, Slightly effective: Slightly suppressed, Invalid: No effect

  As shown in Table 3, 70% of panelists answered that they were effective in Example 1 and Example 2 of this experiment as a result of the anti-dandruff evaluation, and in Examples 1 and 2 of this experiment, as a result of itching suppression evaluation. The panel responding as effective was 80%, showing suppression of dandruff and improvement of itchiness, and very good results were obtained as compared with Comparative Example 1 and Comparative Example 2.

  The antifungal agent of the present invention is preferably used in hair cosmetics because it acts on skin-resident fungi and suppresses its growth. In addition, it can be blended with synthetic resin molded products such as shower caps and hair bands, antibacterial fibers, antibacterial paper, and coloring materials to form antibacterial products.

Claims (5)

General formula

(Wherein R represents an alkyl group having 1 to 11 carbon atoms, and the broken line represents a single bond or one of them is a double bond). . General formula

(Wherein R represents an alkyl group having 1 to 11 carbon atoms, and the broken line represents a single bond or one of them is a double bond). Preventive or therapeutic agent. 4-pentanolide, 4-hexanolide, 4-heptanolide, 4-octanolide, 4-nonanolide, 4-decanolide, 4-undecanolide, 4-dodecanolide, 4-tridecanolide, 4-tetradecanolide, 4-pentadecanolide, 5-methyl-2 ( An antifungal agent comprising at least one selected from 3H) -furanone and 5-methyl-2 (5H) -furanone as an active ingredient. 4-pentanolide, 4-hexanolide, 4-heptanolide, 4-octanolide, 4-nonanolide, 4-decanolide, 4-undecanolide, 4-dodecanolide, 4-tridecanolide, 4-tetradecanolide, 4-pentadecanolide, 5-methyl-2 ( A prophylactic or therapeutic agent for dandruff, comprising at least one selected from 3H) -furanone and 5-methyl-2 (5H) -furanone as an active ingredient. A cosmetic for hair comprising the antifungal agent according to any one of claims 1 to 4 and a preventive or therapeutic agent for dandruff.