JPH0680002B2 - Antibacterial agent - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION Industrial Application Field Recently, an antibacterial agent containing a dicarboxylic acid or an alkali metal salt thereof as an active ingredient has been proposed (JP-A-53-124622).
issue). This antibacterial agent utilizes a dicarboxylic acid having 8 to 20 carbon atoms or its alkali metal salt as an active ingredient, and although the antibacterial properties of these compounds are recognized, all of these compounds dissolve in oils and fats. Since its solubility (fat solubility) is extremely low, there are restrictions in its use. For example, when the above-mentioned antibacterial agent is applied to the storage of oil-and-fat-containing foods and oil-and-fat-containing cosmetics that are easily denatured, the dicarboxylic acid and its alkali metal salt, which are active ingredients, are crystallized with time so that the antibacterial activity is significantly reduced. Become.

DISCLOSURE OF THE INVENTION Problems to be Solved by the Invention The present invention has led to the present invention as a result of examining the form of dicarboxylic acid exhibiting good lipophilicity without impairing the original antibacterial property of dicarboxylic acid.

That is, the present invention is to provide an antibacterial agent exhibiting good fat-solubility while exhibiting antibacterial / antifungal activity having an active ingredient of a dicarboxylic acid having 10 or more carbon atoms in the form of a diester. And

The present invention will be described in detail below.

Structure of the Invention A feature of the present invention is an antibacterial agent for bacteria, yeasts and fungi, which comprises a diester of a dicarboxylic acid represented by the following general formula (I) as an active ingredient.

(Wherein R represents an alkyl group having 11 or more carbon atoms or a cholesteryl group, and n represents an integer of 8 or more) The compound represented by the general formula (I) is a known substance per se, and is colorless. It is to a pale yellow and shows good lipophilicity. Moreover, no toxicity is observed. The carbon number of R in general formula (I) and the upper limit of n are not particularly specified, but about 20 is preferable for each.

Means for Solving the Problems In the present invention, dicarboxylic acid diesters used as active ingredients are exemplified by 1,11-undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, and hexadecanedioic acid. Acid, octadecanedioic acid,
These are esters of nonadecanedioic acid and eicosanedioic acid such as didodecyl, ditetradecyl, dihexadecyl, and dioctadecyl.

Next, the results of testing the antibacterial activity of the active ingredient of the present invention are shown below.

Test method: The following 10 types of test bacteria were used, and broth medium (abbreviated as B medium) and Tuapetsk medium (abbreviated as Cz medium) having the following compositions were used as the medium, and each active ingredient as a sample was tested. The minimum effective concentration required to suppress the growth of the test bacteria was measured and used as their antibacterial activity.

Bacteria: Bacillus subtilis IFO-3134 (abbreviated as Bacillus subtilis, Bs) Escherichia coli IFO-3806 (abbreviated as Escherichia coli, Ec) Aerobic aerogenes IFO-3319 (abbreviated as Aerobacter aerogenes, Aa) ) Syudomonas aeruginosa IFO-12689 (abbreviated as Pseudomonas aeruginosa, Pa) Micrococcus pyogenes FDA-2099 (abbreviated as Micrococcus pyogenes, Mp) Filamentous fungi: Aspergillus niger IFO-6341 (abbreviated as Aspergillus niger, Anni) -Citrinum IFO-6352 (abbreviated as Penicillum citrinum, Pc) Yeast: Trichoderma T-1 IFO-6355 (abbreviated as Trichoderma T-1, T-T-1) Torlopsis canandida IFO-1084 (Torulopsis candida, Tc) Abbreviated as “) Geotritium candeidum IFO-4985 (abbreviated as“ Geotrichum candidum, Gc ”) medium set Bacteriological broth (B medium) agar powder 18.0g broth 5.0g peptone 10.0g saline 5.0g distilled water 100ml filamentous fungi, yeast for Tsuapetsuku medium (Cz medium) agar powder 20.0g sucrose 30.0g NaNO ₃ 2.0g K ₂ HPO _{4 1.0g KCl 0.5g MgSO 4 · 7H} 2 O 0.5g FeSO 4 0.01g density of the density adjustment each active ingredient distilled water 1000ml test active ingredient, the upper limit is 10,000ppm to a medium 10ml in Shiyare a lower limit of 1ppm Prepared and added to the above-mentioned range by adjusting the concentration to the following concentrations.

Unit (ppm) 1,5,10,33,66,100,330,660,1000,3300,6600,10,000 Measurement of minimum inhibitory concentration (MIC) of sample bacteria (a) Bacterial ear volume of bacteria grown in slope culture medium Was inoculated into 10 ml of broth liquid culture medium and cultured at about 37 ° C. for 24 hours, and then the culture solution was diluted to 10 ⁻² with sterilized distilled water to obtain a test bacterial solution.

Next, each platinum agar culture medium of 10 ml of broth medium to which the active ingredient of the sample was added so as to have each of the above concentrations was smeared with 1 platinum loop of the test bacterial solution, and incubated at 37 ° C for 24 hours or 48 hours. After that, the minimum inhibitory concentration was examined by the presence or absence of colonies formed in each culture medium to determine the antibacterial activity.

(B) Yeast One platinum loop amount was inoculated into 10 ml of Sabouraud liquid culture medium on yeast grown in a slant culture medium and cultured at 28 ° C. for 24 hours, and the culture solution was directly used as a test bacterial solution.

Next, 1 platinum loop amount of the test bacterial solution was smeared on each plate culture medium of 10 ml of Tuapetsk agar medium to which the active ingredient of the sample was added so as to have the above respective concentrations, and after culturing at 28 ° C for 7 days, The minimum inhibitory concentration was examined by the presence or absence of colonies formed in the culture medium to determine the antibacterial activity.

(C) Filamentous fungus Pour 10 ml of sterile distilled water into the slant culture medium of the filamentous fungus grown in the slant, use platinum fishing to disperse the spores and hyphae sufficiently, and further shake vigorously to vibrate the spores and The hyphae were well dispersed.

Then, the contents of the culture medium dispersed as described above were rubbed with sterile gauze, and the filtrate was used as a test bacterial solution. The test bacterial solution was cultured at 28 ° C. for 7 days by the same method as in the case of yeast, and the growth state was observed to determine the antibacterial activity. The hyphae of which growth is not inhibited are sufficiently grown, the hyphae of which are inhibited to some extent are incomplete, and the hyphae of which are completely inhibited do not grow at all.

The test results are shown in Tables 1 and 2. The numbers of the active ingredients in each table indicate the compounds of the following formulas.

As seen in Table 1 and Table 2, the active ingredient used in the present invention has antibacterial activity against many microorganisms such as bacteria, yeast and filamentous fungi at a concentration of about 1% by weight.
As described above, these active ingredients are colorless to pale yellow and transparent, have almost no odor, and show good lipophilicity, and are therefore effective as preservatives for various fat-containing foods and oily cosmetics. .

The antibacterial agent according to the present invention has the general formula (I) as an active ingredient.
The dicarboxylic acid diester represented by the above can be used alone or in combination of two or more, and the mixture can be used as it is, so that it is easy to handle. Further, the above-mentioned active ingredients can be used in combination with food additives and cosmetic additives.

Although the amount of the antibacterial agent of the present invention used varies depending on the type of the active ingredient and the object to be preserved, considering the antibacterial activity shown in Tables 1 and 2, it can be said that an excellent preservation effect is exhibited at about 1% by weight. .

 ─────────────────────────────────────────────────── ─── Continued Front Page (72) Inventor Takuo Uejima 7-15-24 Maebaru Nishi, Funabashi City, Chiba Prefecture (72) Inventor Ken Ono 2-38-25 Nishi Nishinuma City, Sagamihara City, Kanagawa Prefecture (72) Inventor Ei Taoka 1-12-32 Akasaka, Minato-ku, Tokyo Within Japan Mining Industry Co., Ltd. (72) Inventor Akio Watanabe 3-17-35, Shinzonan, Toda City, Saitama Prefecture Within Japan Mining Co., Ltd.

Claims (1)

[Claims] 1. A general formula (Wherein R represents an alkyl group having 11 or more carbon atoms or a cholesteryl group, and n represents an integer of 8 or more), and an antibacterial agent containing a dicarboxylic acid diester as an active ingredient.