JP7744664B2 - Antibacterial agent, antibacterial oral composition, antibacterial topical preparation for skin, and method for inhibiting bacterial growth in food and drink - Google Patents

Description

The present invention relates to an antibacterial agent, an antibacterial oral composition, an antibacterial topical skin preparation, and a method for inhibiting bacterial growth in foods and beverages.

Antibacterial agents are widely used in cosmetics, pharmaceuticals, food and beverages, and other products to prevent microbial contamination and deterioration (spoilage and spoilage) of products, as well as to prevent infectious diseases, and are extremely useful in terms of quality control and public health.

Products such as cosmetics and food and beverages are susceptible to contamination and deterioration (spoilage and spoilage) caused by the proliferation of bacteria such as Escherichia (e.g., E. coli), Staphylococcus (e.g., Staphylococcus aureus), and Bacillus (e.g., Bacillus subtilis). Food and beverage products in particular pose a risk of food poisoning due to the proliferation of bacteria such as Escherichia (e.g., E. coli) and Staphylococcus (e.g., Staphylococcus aureus). For this reason, antibacterial agents are sometimes used to maintain product quality.

A rich and diverse range of bacteria inhabit the human intestine and skin, maintaining homeostasis by maintaining a balance among them. However, an imbalance in the microbiota can cause various diseases.
For example, Escherichia bacteria (e.g., Escherichia coli) are known to cause gastroenteritis, urinary tract infections, and food poisoning due to secondary contamination of food and water. Staphylococcus bacteria (e.g., Staphylococcus aureus) can also cause atopic dermatitis. In particular, S. aureus is known to produce various protein toxins. For example, the epidermal exfoliative toxin produced by S. aureus acts on the skin throughout the body via the bloodstream, cleaving desmoglein 1, a desmosome-forming protein, and causing intraepidermal blisters. Furthermore, toxic shock syndrome toxins act on T lymphocytes, causing severe inflammation and resulting in a systemic toxic disease characterized by sudden fever, hypotension, scarlet fever-like erythema, and multiple organ damage (Non-Patent Document 1). Enterotoxins produced by S. aureus during proliferation in food are known to cause food poisoning, the main symptom of which is emetic toxicity (Non-Patent Document 2). Furthermore, Staphylococcus aureus is known as a major causative bacterium of hospital-acquired pneumonia. Antibacterial agents may also be used to prevent, treat, or improve such diseases.

Patent Document 1 describes an antibacterial agent characterized by containing hydroxylated fullerene as an active ingredient. Patent Document 2 describes an antibacterial agent consisting of a glyceryl ascorbic acid derivative or its salt.

JP 2009-179615 A JP 2015-3894 A

Hiroshi Shimizu, "New Dermatology: 3rd Edition," Nakayama Shoten Publishing, February 15, 2018, pp. 514-531 Food Hygiene, Vol. 51, No. 4, 2005, pp. 81-90

However, frequent use of the same antibacterial agent can lead to the emergence of bacteria that are resistant to that agent, making it impossible to suppress bacterial growth. For this reason, there is a need for the development of new antibacterial agents.

The present invention aims to provide an antibacterial agent, an antibacterial oral composition, and an antibacterial topical skin preparation. It also aims to provide a method for inhibiting bacterial growth in food and beverages.

In order to solve the above problems, the antibacterial agent of the present invention is characterized by containing as an active ingredient a compound represented by the following formula (I). The antibacterial oral composition and antibacterial topical skin preparation of the present invention are characterized by incorporating a compound represented by the following formula (I). Furthermore, the method of the present invention for inhibiting bacterial growth in food and beverages is characterized by incorporating a compound represented by the following formula (I) into the food and beverage.

According to the present invention, by using the compound represented by formula (I) above as an active ingredient, it is possible to provide an antibacterial agent, an antibacterial oral composition, and an antibacterial topical skin preparation with excellent antibacterial activity. Furthermore, by incorporating the compound represented by formula (I) above into food and beverage products, it is possible to provide a method for inhibiting bacterial growth in food and beverage products.

Hereinafter, an embodiment of the present invention will be described.
The antibacterial agent according to this embodiment contains a compound represented by the following formula (I) as an active ingredient.

The compound represented by formula (I) above is a cinnamic acid derivative also known as 3-(4-hydroxy-3-methoxyphenyl)propionic acid. Hereinafter, in this specification, the compound represented by formula (I) above may be referred to as compound (I).

Compound (I) can be produced, for example, by isolating and purifying from a plant extract containing compound (I). In this case, such a plant extract containing compound (I) can be obtained by a method commonly used for plant extraction. Examples of plants containing compound (I) include rice, barley, wheat, soybeans, adzuki beans, and corn.

Compound (I) can also be produced by fermenting 3-(4-hydroxy-3-methoxyphenyl)propenoic acid or a derivative thereof, or a composition containing the same (e.g., crushed plant material or extract, etc.) with a microorganism having phenolic acid reductase, converting the 3-(4-hydroxy-3-methoxyphenyl)propenoic acid to compound (I), and then extracting, isolating, and purifying the resulting fermentation product. Examples of compositions containing 3-(4-hydroxy-3-methoxyphenyl)propenoic acid include crushed plant material and extracts from plants such as coffee, wheat, corn, tomato, yerba mate, mugwort, and burdock. Furthermore, because 3-(4-hydroxy-3-methoxyphenyl)propenoic acid is a component of lignin in woody and herbaceous plants, lignin or a composition containing it may also be used as the fermentation raw material. On the other hand, examples of microorganisms having phenolic acid reductase include lactic acid bacteria such as Lactobacillus plantarum, Lactobacillus fermentum, Lactobacillus gasseri, Lactobacillus johnsonii, Lactobacillus crispatus, Lactobacillus acidophilus, Lactobacillus amylovorus, Lactobacillus delbrueckii, Lactobacillus buchneri, Lactobacillus kefiranofaciens, Lactobacillus gallinarum, and Enterococcus faecalis.

The method for extracting, isolating, and purifying compound (I) from the above-mentioned plant or fermented product is not particularly limited, and can be carried out according to conventional methods. For example, the extraction process can be carried out by drying the above-mentioned plant or fermented product as the extraction raw material, and then subjecting it to extraction with an extraction solvent either directly or after pulverization using a crusher. Drying can be carried out in the sun or using a commonly used dryer. The raw material can also be used after pretreatment such as degreasing with a nonpolar solvent such as hexane. Pretreatment such as degreasing allows for efficient extraction with a polar solvent.

It is preferable to use a polar solvent as the extraction solvent, such as water or a hydrophilic organic solvent. These can be used alone or in combination of two or more, preferably at room temperature or a temperature below the boiling point of the solvent.

Water that can be used as an extraction solvent includes pure water, tap water, well water, mineral water, hot spring water, spring water, fresh water, etc., as well as water that has undergone various treatments. Treatments that can be applied to water include, for example, purification, heating, sterilization, filtration, ion exchange, osmotic pressure adjustment, buffering, etc. Therefore, water that can be used as an extraction solvent in this embodiment also includes purified water, hot water, ion-exchanged water, saline, phosphate buffer, phosphate-buffered saline, etc.

Hydrophilic organic solvents that can be used as extraction solvents include lower aliphatic alcohols with 1 to 5 carbon atoms, such as methanol, ethanol, propyl alcohol, and isopropyl alcohol; lower aliphatic ketones, such as acetone and methyl ethyl ketone; and polyhydric alcohols with 2 to 5 carbon atoms, such as 1,3-butylene glycol, propylene glycol, and glycerin.

When a mixture of two or more polar solvents is used as the extraction solvent, the mixing ratio may be any and can be adjusted appropriately. For example, when a mixture of water and a hydrophilic organic solvent is used as the extraction solvent, the mixture may be mixed at any ratio, i.e., between more than 0:100 and less than 100:0 (volume ratio, hereinafter the same), and can be adjusted appropriately.
For example, when a mixture of water and a lower aliphatic alcohol is used as the extraction solvent, the mixing ratio (volume ratio) of water to lower aliphatic alcohol can be 9:1 or more, or even 7:3 or more, or the mixing ratio of water to lower aliphatic alcohol can be 1:9 or less, or even 2:8 or less. When a mixture of water and a polyhydric alcohol is used, the mixing ratio of water to polyhydric alcohol can be 8:2 or more, or 1:9 or less, and when a mixture of water and a lower aliphatic ketone is used, the mixing ratio of water to lower aliphatic ketone can be 9:1 or more, or 2:8 or less.

The extraction process is not particularly limited as long as it allows the soluble components contained in the extraction raw material to be dissolved in the extraction solvent, and can be carried out according to conventional methods. For example, the extraction raw material is immersed in an extraction solvent in an amount (mass ratio) 5 to 15 times the amount of the extraction raw material, and the soluble components are extracted at room temperature or under reflux heating. The extract can then be obtained by filtering to remove the extraction residue. Distilling the solvent from the resulting extract yields a paste-like concentrate, which can then be further dried to obtain a dried product.

The method for isolating and purifying compound (I) from the extract, concentrate, or dried extract obtained as described above is not particularly limited and can be performed using conventional methods. For example, the extract may be dissolved in a developing solvent and subjected to column chromatography using a porous material such as silica gel or alumina, or a porous resin such as a styrene-divinylbenzene copolymer or polymethacrylate, to recover a fraction containing compound (I). In this case, the developing solvent may be selected appropriately depending on the stationary phase used. For example, when the extract is separated by normal-phase chromatography using silica gel as the stationary phase, the developing solvent may be chloroform:methanol=95:5. Furthermore, the fraction containing compound (I) obtained by column chromatography may be purified using any organic compound purification method, such as reverse-phase silica gel chromatography using ODS, recrystallization, liquid-liquid countercurrent extraction, or column chromatography using an ion exchange resin.

Compound (I) obtained in the manner described above has excellent antibacterial activity and can therefore be used as an active ingredient in antibacterial agents. Compound (I) can also be used to produce antibacterial agents. The antibacterial agent of this embodiment can be used in a wide range of applications, including pharmaceuticals, quasi-drugs, cosmetics, and food and beverage products.

In addition, a composition containing compound (I) may be used as the active ingredient of the antibacterial agent of this embodiment instead of isolated compound (I). Here, "composition containing compound (I)" in this embodiment includes an extract obtained using a plant containing compound (I) as the extraction raw material, a fermentation product containing compound (I), and an extract obtained using the fermentation product as the extraction raw material. Furthermore, "extract" includes an extract obtained by extraction treatment, a diluted or concentrated solution of the extract, or a dried product obtained by drying the extract.

When a composition containing compound (I) is used as the active ingredient of the antibacterial agent of this embodiment, the content of compound (I) in the composition is preferably 0.1% by mass or more, more preferably 5% by mass or more, and particularly preferably 50% by mass or more. By using compound (I) with a higher purity as the active ingredient, an antibacterial agent with even better action and effectiveness can be obtained.

The antibacterial agent of this embodiment may consist solely of compound (I) or a composition containing compound (I), or may be a formulation of compound (I) or a composition containing compound (I).

The antibacterial agent of this embodiment can be formulated into any dosage form, such as powder, granules, tablets, or liquid, using a pharmaceutically acceptable carrier such as dextrin or cyclodextrin, or any other auxiliary agent, according to standard methods. In this case, examples of auxiliary agents that can be used include excipients, binders, disintegrants, lubricants, stabilizers, and flavoring/flavoring agents. The antibacterial agent can be incorporated into other compositions (e.g., topical skin preparations, oral compositions, etc., as described below) and can also be used as ointments, topical liquid preparations, patches, etc.

When the antibacterial agent of this embodiment is formulated, the content of compound (I) or a composition containing compound (I) is not particularly limited and can be set appropriately depending on the purpose.

If necessary, the antibacterial agent of this embodiment can be used as an active ingredient by blending other natural extracts or the like having antibacterial activity with compound (I) or a composition containing compound (I).

The antibacterial agent of this embodiment can be administered to patients via transdermal administration, oral administration, etc., but a method suitable for prevention or treatment may be selected appropriately depending on the type of disease. Furthermore, the dosage of the antibacterial agent of this embodiment may be increased or decreased as appropriate depending on the type and severity of the disease, individual patient differences, administration method, administration period, etc.

The antibacterial agent of this embodiment can be used regardless of the type of bacteria to which it is applied. Gram-negative and Gram-positive bacteria are particularly preferred. Examples of Gram-negative bacteria include Escherichia (e.g., Escherichia coli), Salmonella, Pseudomonas (e.g., Pseudomonas aeruginosa), Helicobacter, and Neisseria (e.g., Neisseria gonorrhoeae and Neisseria meningitidis). Examples of Gram-positive bacteria include Staphylococcus (e.g., Staphylococcus aureus, Staphylococcus epidermidis), Enterococcus, Streptococcus (e.g., diplococcus, tetrastreptococcus, octastreptococcus, etc., Streptococcus pneumoniae, Streptococcus hemolyticus, and Clostridium mutans), Bacillus (e.g., Bacillus anthracis, Bacillus subtilis), Clostridium (e.g., Clostridium tetani, Clostridium botulinum), Micrococcus (e.g., Micrococcus luteus), Corynebacterium (e.g., Corynebacterium xerosis, Corynebacterium diphtheriae), and Propionibacterium (e.g., Propionibacterium acnes). Among these, bacteria of the genus Escherichia, Staphylococcus, and Bacillus are particularly preferred, with Escherichia coli, Staphylococcus aureus, and Bacillus subtilis being even more preferred, from the viewpoint of more effectively exerting the antibacterial effect of this embodiment.

The antibacterial agent of this embodiment can inhibit bacterial growth through the antibacterial action of compound (I), thereby preventing contamination and deterioration (putrefaction and deterioration) of compositions containing the antibacterial agent (for example, topical skin preparations and foods and beverages described below), and also enabling the antibacterial agent to be administered to humans and the like to prevent, treat, or ameliorate various infectious diseases.
More specifically, for example, by adding it to food and beverages, it is possible to inhibit the growth of bacteria that can cause contamination or deterioration (putrefaction or deterioration) of food and beverages, such as Bacillus (e.g., Bacillus subtilis), Escherichia (e.g., Escherichia coli) and Staphylococcus (e.g., Staphylococcus aureus), which can cause food poisoning, and thereby maintain the quality of the food and beverages.
Furthermore, by administering the compound to humans or the like, it is possible to prevent, treat, or ameliorate diseases (e.g., gastroenteritis, urinary tract infections, food poisoning, etc.) caused by bacteria of the genus Escherichia (e.g., Escherichia coli). It is also possible to prevent, treat, or ameliorate diseases (e.g., skin infections such as atopic dermatitis and blisters, systemic toxic diseases, food poisoning, pneumonia, etc.) caused by bacteria of the genus Staphylococcus (e.g., Staphylococcus aureus). However, the antibacterial agent of this embodiment can be used for all applications in which it is significant to exert the antibacterial activity of compound (I) in addition to these applications.

The antibacterial agent of this embodiment has excellent antibacterial activity and can therefore be suitably used as a reagent for research into the mechanisms of these actions.

Compound (I) has excellent antibacterial activity and is therefore suitable for incorporation into, for example, topical skin preparations and oral compositions, including foods and beverages. In this case, compound (I) may be incorporated as is, or an antibacterial agent formulated from compound (I) may be incorporated.

By incorporating compound (I) or an antibacterial agent formulated from compound (I) into a topical skin preparation, bacterial growth in the topical skin preparation can be inhibited, and contamination and deterioration (putrefaction and deterioration) of the topical skin preparation can be inhibited. Furthermore, by incorporating compound (I) or an antibacterial agent formulated from compound (I) into a topical skin preparation, the topical skin preparation can be made suitable for antibacterial applications, such as the prevention, treatment, or amelioration of skin infections caused by bacteria of the genus Staphylococcus (e.g., Staphylococcus aureus). The above-mentioned effects are advantageous because they are easily exerted when imparted to a topical skin preparation.

Here, topical skin preparations are not limited to specific categories and include a wide range of transdermal medicines, quasi-drugs, and skin cosmetics. Specific examples include ointments, creams, emulsions, serums, lotions, masks, foundations, lip balms, bath additives, hair tonics, hair lotions, soaps, and body shampoos.

The amount of compound (I) in a topical skin preparation can be adjusted as appropriate depending on the type of topical skin preparation, but a suitable blending ratio is 0.100% to 100% by mass, and a particularly suitable blending ratio is 0.125% to 100% by mass. In particular, when compound (I) is added to a topical skin preparation to inhibit bacterial growth, the amount of compound (I) added is not particularly limited as long as it is an amount that can inhibit bacterial growth, but is typically 0.100% to 50.0% by mass, and preferably 0.125% to 30.0% by mass, relative to the topical skin preparation.

By incorporating compound (I) or an antibacterial agent formulated from compound (I) into an oral composition, bacterial growth in the oral composition can be inhibited, and contamination and deterioration (putrefaction and deterioration) of the oral composition can be inhibited. Furthermore, by incorporating compound (I) or an antibacterial agent formulated from compound (I) into an oral composition, an oral composition suitable for antibacterial applications (e.g., for the prevention, treatment, or amelioration of various infectious diseases) can be obtained. The above-mentioned effects are advantageous because they are more easily exerted when imparted to an oral composition.

An oral composition refers to a composition that is resistant to harm to human health and is taken orally or by gastrointestinal administration in normal social life. It is not limited to administrative classifications such as food, medicine, or quasi-drug. Therefore, in this embodiment, "oral composition" broadly includes orally taken general foods, feed, health foods, health functional foods (foods for specified health uses, foods with nutrient functions, foods with functional claims), quasi-drugs, medicines, etc. The oral composition of this embodiment is preferably an oral composition that can display the favorable effects of compound (I) on the oral composition or its packaging, and is particularly preferably a health functional food (foods for specified health uses, foods with nutrient functions, foods with functional claims), quasi-drugs, or medicines.

When compound (I) is incorporated into an oral composition, the amount can be adjusted as appropriate, taking into account the intended use, symptoms, gender, etc. However, taking into account the general intake of the oral composition to which it is added, it is preferable to adjust the amount of extract to be ingested so that the daily intake amount for an adult is approximately 1 to 1,000 mg. Furthermore, when the oral composition to which compound (I) is added is in the form of granules, tablets, or capsules, the amount of compound (I) added is not particularly limited as long as it is an amount that can prevent, treat, or ameliorate various infectious diseases, but is usually 0.100% to 100% by mass, and preferably 0.125% to 100% by mass, of the oral composition to which it is added.

When producing the oral composition of this embodiment, any desired form of oral composition can be prepared by adding any desired auxiliary agent, such as sugars such as dextrin and starch; proteins such as gelatin, soy protein and corn protein; amino acids such as alanine, glutamine and isoleucine; polysaccharides such as cellulose and gum arabic; or fats and oils such as soybean oil and medium-chain fatty acid triglycerides.

The oral compositions that can contain compound (I) are not particularly limited, but specific examples include the foods and beverages exemplified below, as well as tablets, capsules, and drinks; various toothpastes, mouthwashes, lozenges, oral pastes, gum massage creams, gargles, mouth fresheners, and other oral preparations; and the like. When compound (I) is incorporated into these oral compositions, commonly used auxiliary ingredients and additives can be used in combination.

In particular, by incorporating compound (I) or an antibacterial agent formulated from compound (I) into food and beverages, it is possible to inhibit the growth of bacteria in the food and beverages, thereby preventing contamination and deterioration (putrefaction and deterioration) of the food and beverages and preserving their quality.

Foods and beverages that can incorporate compound (I) are not particularly limited, but specific examples include beverages such as soft drinks, carbonated drinks, nutritional drinks, fruit drinks, and lactic acid drinks (including concentrated concentrates and powders for adjusting these beverages); frozen desserts such as ice cream, ice sherbet, and shaved ice; noodles such as soba, udon, vermicelli, gyoza wrappers, shumai wrappers, Chinese noodles, and instant noodles; sweets such as candy, chewing gum, candy, chewing gum, chocolate, candy tablets, snacks, biscuits, jelly, jam, cream, and baked goods; processed seafood and livestock foods such as kamaboko, ham, and sausage; dairy products such as processed milk and fermented milk; oils and fats and oil-based foods such as salad oil, tempura oil, margarine, mayonnaise, shortening, whipped cream, and dressings; condiments such as sauces and dressings; soups, stews, salads, side dishes, and pickles; and various other forms of health functional foods. When compound (I) is formulated into these oral compositions, commonly used auxiliary ingredients and additives can be used in combination.

When compound (I) is added to foods and beverages to inhibit bacterial growth, the amount of compound (I) added is not particularly limited as long as it is an amount that can inhibit bacterial growth, but is typically 0.100% to 90.0% by mass, preferably 0.125% to 50.0% by mass, and more preferably 30.0% to 50.0% by mass, of the food or beverage to which it is added.

The antibacterial agent, topical skin preparation, and oral composition including food and beverage products of this embodiment can be appropriately formulated with, for example, moisturizers, antioxidants, stabilizers, inorganic salts, pH adjusters, plant extracts, etc., depending on their form and intended use, as long as the antibacterial effect is not inhibited.

The antibacterial agent, topical skin preparation, and oral composition including food and beverage products of this embodiment are preferably applied to humans, but can also be applied to animals other than humans (e.g., mice, rats, hamsters, dogs, cats, cows, pigs, monkeys, etc.) as long as their respective effects are achieved.

The present invention will be explained in detail below using test examples, but the present invention is not limited to the following examples. In these test examples, compound (I) (Tokyo Chemical Industry Co., Ltd., 3-(4-Hydroxy-3-methoxyphenyl)propionic Acid, Sample 1) was used as the test sample.

Test Example 1 Antibacterial Activity Test Against Escherichia coli Sample 1 was dissolved and diluted with distilled water to prepare a 10% (w/v) sample solution, which was then sterilized. After sterilization, the sample solution was dispensed into a petri dish, and 10 mL of standard agar medium (manufactured by Nissui Pharmaceutical Co., Ltd.) was added to adjust the concentration of Sample 1 to that shown in Table 1. The added sample solution and standard agar medium were mixed in the petri dish, and the medium was then solidified.

A suspension of Escherichia coli was applied to the surface of the prepared medium and allowed to stand at 37° C. for 1 to 2 days, after which the presence or absence of colony formation was visually determined.
The evaluation method is as follows.
+: Colony formation was observed. -: Colony formation was not observed. The results are shown in Table 1.

Test Example 2: Antibacterial Activity Test Against Staphylococcus aureus Sample 1 was dissolved and diluted with distilled water to prepare a 10% (w/v) sample solution, which was then sterilized. After sterilization, the sample solution was dispensed into a petri dish, and 10 mL of standard agar medium (manufactured by Nissui Pharmaceutical Co., Ltd.) was added to adjust the concentration of Sample 1 to that shown in Table 2. The added sample solution and standard agar medium were mixed in the petri dish, and the medium was then solidified.

A suspension of Staphylococcus aureus was applied to the surface of the prepared medium and allowed to stand at 37° C. for 1 to 2 days, after which the presence or absence of colony formation was determined with the naked eye.
The evaluation method is as follows.
+: Colony formation was observed. -: Colony formation was not observed. The results are shown in Table 2.

Test Example 3: Antibacterial Activity Test Against Bacillus subtilis Sample 1 was dissolved and diluted with distilled water to prepare a 10% (w/v) sample solution, which was then sterilized. After sterilization, the sample solution was dispensed into a petri dish, and 10 mL of standard agar medium (manufactured by Nissui Pharmaceutical Co., Ltd.) was added to adjust the concentration of Sample 1 to that shown in Table 3. The added sample solution and standard agar medium were mixed in the petri dish, and the medium was then solidified.

A suspension of Bacillus subtilis was applied to the surface of the prepared medium and allowed to stand at 37° C. for 1 to 2 days, after which the presence or absence of colony formation was determined with the naked eye.
The evaluation method is as follows.
+: Colony formation was observed. -: Colony formation was not observed. The results are shown in Table 3.

As shown in Tables 1 to 3, compound (I) (sample 1) was confirmed to exhibit excellent antibacterial activity.

[Formulation example 1]
A cream having the following composition was prepared by a conventional method.
Compound (I) 0.5g
Sophora root extract 0.1g
Scutellaria root extract 0.1g
Liquid paraffin 5.0g
White beeswax 4.0g
Squalane 10.0g
Cetanol 3.0g
Lanolin 2.0g
Stearic acid 1.0g
Polyoxyethylene sorbitan oleate (20E.O.) 1.5g
Glyceryl monostearate 3.0g
Oil-soluble licorice extract 0.1g
1,3-butylene glycol 6.0g
Methyl parahydroxybenzoate 1.5g
Fragrance 0.1g
Purified water Remainder (total amount is 100g)

[Formulation example 2]
An emulsion was prepared in a conventional manner according to the following composition.
Compound (I) 0.15g
Jojoba oil 4.00g
1,3-butylene glycol 3.00g
Arbutin 3.00g
Polyoxyethylene cetyl ether (20E.O.) 2.50g
2.00g olive oil
Squalane 2.00g
Cetanol 2.00g
Glyceryl monostearate 2.00g
Polyoxyethylene sorbitan oleate (20E.O.) 2.00g
Methyl parahydroxybenzoate 0.15g
Stearyl glycyrrhetinate 0.10g
Phellodendron bark extract 0.10g
Dipotassium glycyrrhizinate 0.10g
Ginkgo biloba extract 0.10g
Conchiolin 0.10g
Phellodendron bark extract 0.10g
Chamomile extract 0.10g
Fragrance 0.05g
Purified water Remainder (total amount is 100g)

[Formulation example 3]
A cosmetic essence having the following composition was prepared by a conventional method.
Compound (I) 1.0g
Chamomile extract 0.1g
Carrot extract 0.1g
Xanthan gum 0.3g
Hydroxyethyl cellulose 0.1g
Carboxyvinyl polymer 0.1g
1,3-butylene glycol 4.0g
Dipotassium glycyrrhizinate 0.1g
Glycerin 2.0g
Potassium hydroxide 0.25g
Fragrance 0.01g
Preservative (methyl parahydroxybenzoate) 0.15g
Ethanol 2.0g
Purified water Remainder (total amount is 100g)

[Formulation example 4]
Tablets having the following composition were prepared by a conventional method.
Compound (I) 5.0 mg
Dolomite (contains 20% calcium and 10% magnesium) 83.4 mg
Casein phosphopeptide 16.7mg
Vitamin C 33.4mg
Maltitol 136.8mg
Collagen 12.7mg
Sucrose fatty acid ester 12.0 mg

[Formulation example 5]
An oral liquid preparation having the following composition was prepared by a conventional method.
<Composition in 1 ampoule (100 mL each)>
Compound (I) 0.5% by mass
Sorbitol 12.0% by mass
Sodium benzoate 0.1% by mass
Fragrance 1.0% by mass
Calcium sulfate 0.5% by mass
Purified water remainder (100% by mass)

The antibacterial agent of the present invention can significantly contribute to, for example, the prevention, treatment, or amelioration of various infectious diseases, and the prevention of product contamination and deterioration (spoilage and spoilage).

Claims (4)

An antibacterial agent characterized by comprising a compound represented by the following formula (I) as an active ingredient:
A method for inhibiting bacterial growth in food and drink by adding a compound represented by the following formula (I) to the food and drink:
An antibacterial oral composition comprising a compound represented by the following formula (I):
An antibacterial skin preparation for external use, characterized by comprising a compound represented by the following formula (I):