WO2017188195A1 - Antibacterial agent and antibacterial treatment method - Google Patents
Antibacterial agent and antibacterial treatment method Download PDFInfo
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- WO2017188195A1 WO2017188195A1 PCT/JP2017/016251 JP2017016251W WO2017188195A1 WO 2017188195 A1 WO2017188195 A1 WO 2017188195A1 JP 2017016251 W JP2017016251 W JP 2017016251W WO 2017188195 A1 WO2017188195 A1 WO 2017188195A1
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
Definitions
- the present invention relates to an antibacterial agent and an antibacterial method, and particularly to an antibacterial agent capable of releasing an antibacterial component and an antibacterial method using the antibacterial agent.
- aldehyde compounds having 6 carbon atoms such as hexanal, 2-hexenal, and 3-hexenal have attracted attention as natural products having antibacterial activity (see, for example, Non-Patent Document 1).
- Non-Patent Document 1 the above-mentioned aldehyde compound having 6 carbon atoms and the inclusion complex in which the aldehyde compound having 6 carbon atoms is included in the pore portion of ⁇ -cyclodextrin exhibit excellent antibacterial effects. Is disclosed.
- the antibacterial agent containing hexanal, 2-hexenal or 3-hexenal as it is as an antibacterial component has a problem in that it has a strong odor and is difficult to use.
- an antibacterial agent containing hexanal, 2-hexenal or 3-hexenal as it is, and an antibacterial agent using an inclusion complex formed by inclusion of hexanal, 2-hexenal or 3-hexenal with ⁇ -cyclodextrin there was room for improvement in that the antimicrobial effect was not sufficiently durable.
- the present inventors have intensively studied to achieve the above object.
- the inventors of the present invention can release hexanal, 2-hexenal or 3-hexenal as an antibacterial component by an antibacterial agent containing a predetermined acetal compound, and further, the odor is suppressed and the antibacterial effect is sustained.
- the present invention was completed.
- the antibacterial agent of this invention is the following general formula (I):
- R 1 is an n-pentyl group, 1-pentenyl group or 2-pentenyl group
- R 2 is a divalent organic group.
- the acetal compound represented by the general formula (I) generates R 1 CHO and R 2 (OH) 2 when hydrolyzed. Therefore, when the acetal compound represented by the above general formula (I) is contained, the antibacterial effect is sustained by gradually releasing hexanal, 2-hexenal or 3-hexenal by hydrolysis of the acetal compound while suppressing odor. Can be obtained.
- R 2 is glycerin, pentyl glyceryl ether, 2-ethylhexyl glyceryl ether, ethylene glycol, butanediol, pentanediol, hexanediol, heptanediol, octanediol, nonanediol, decanediol.
- R 2 is preferably a residue obtained by removing two hydroxyl groups from a water-soluble compound containing two or more hydroxyl groups. If R 2 is the above-mentioned residue, R 2 (OH) 2 produced by hydrolysis of the acetal compound is water-soluble, so that components remaining after use of the antibacterial agent can be easily removed by washing with water. Because.
- water-soluble compound refers to a compound having a solubility in water of 10 g / 100 g-H 2 O or more at 25 ° C.
- the antibacterial method of this invention includes the process of hydrolyzing the said acetal compound using any of the antibacterial agents mentioned above. It is characterized by that. If the acetal compound represented by the general formula (I) is hydrolyzed, the antibacterial effect can be continuously obtained by gradually releasing hexanal, 2-hexenal or 3-hexenal while suppressing odor.
- an antibacterial agent capable of releasing hexanal, 2-hexenal, or 3-hexenal as an antibacterial component, further suppressing odor, and having excellent antibacterial effects.
- the antibacterial effect can be continuously obtained by gradually releasing hexanal, 2-hexenal or 3-hexenal while suppressing odor.
- the acetal compound contained in the antibacterial agent of this invention can emit a suitable fragrance by the sustained release of an aldehyde, it can also be utilized as a fragrance
- R 2 which is an arbitrary divalent organic group is not particularly limited, and examples thereof include a residue obtained by removing two hydroxyl groups from a compound containing two or more hydroxyl groups (—OH). Specifically, examples of R 2 include a residue obtained by removing two hydroxyl groups from a polyhydric alcohol or a derivative thereof, or a residue obtained by removing two hydroxyl groups from a saccharide or a derivative thereof.
- examples of R 2 include divalent alcohols such as ethylene glycol, butanediol, pentanediol, hexanediol, cyclohexanediol, heptanediol, octanediol, nonanediol, decanediol, and dodecanediol, and glycerin.
- divalent alcohols such as ethylene glycol, butanediol, pentanediol, hexanediol, cyclohexanediol, heptanediol, octanediol, nonanediol, decanediol, and dodecanediol, and glycerin.
- Trivalent alcohols such as butanetriol, pentanetriol, hexanetriol, heptanetriol, octanetriol, nonanetriol, decanetriol and dodecanetriol, pentylglyceryl ether, 2-ethylhexylglyceryl ether and 3-methoxy-1,2-propane Trivalent alcohol derivatives such as diols, glucose, galactose, mannose, xylose, fructose, N-acetylglucosamine, etc.
- R 2 represents the following general formula (II) or (III):
- R 3 , R 4 and R 5 are hydrogen atoms or organic groups, which may be the same or different from each other, and two or more are bonded to each other to form a ring. A structure may be formed, and “*” indicates a bond.
- it is group represented by these. That is, the residue obtained by removing two hydroxyl groups from the compound described above preferably has a structure represented by the general formula (II) or (III).
- R 2 is a residue obtained by removing two hydroxyl groups from a water-soluble compound containing two or more hydroxyl groups. preferable. If R 2 is a residue obtained by removing two hydroxyl groups from a water-soluble compound, R 2 (OH) 2 produced by hydrolysis of the acetal compound becomes a water-soluble compound, and the components remaining after use of the antibacterial agent are washed with water. It can be easily removed. From the viewpoint of facilitating washing of the components remaining after the use of the antibacterial agent, the solubility of the water-soluble compound in water is preferably 10 g / 100 g-H 2 O or more at 25 ° C.
- the solubility of the water-soluble compound in water is preferably 200 g / 100 g-H 2 O or less at 25 ° C., more preferably 180 g / 100 g-H 2 O or less.
- the water-soluble compound containing two or more hydroxyl groups is not particularly limited, and examples thereof include D-glucose (91), D-lactose (21), arbutin (13), and gluconolactone (50). (Numerical values in parentheses are solubility in 100 g of water at a temperature of 25 ° C. [unit: g / 100 g-H 2 O]).
- the carbon number of R 2 is preferably 2 or more, and more preferably 6 or more. If the carbon number of R 2 is not less than the above lower limit, the volatility of the acetal compound can be reduced and the generation of odor can be sufficiently suppressed. From the viewpoint of increasing the water solubility of R 2 (OH) 2 produced by hydrolysis of the acetal compound and the acetal compound, the carbon number of R 2 is preferably 60 or less, and more preferably 30 or less. preferable.
- R 2 preferably does not have an unsubstituted amino group (—NH 2 ). This is because an acetal compound in which R 2 has an unsubstituted amino group (—NH 2 ) is prone to side reactions during synthesis and is difficult to synthesize.
- the following acetal compounds (1) to (6) are preferable as the acetal compound contained in the antibacterial agent of the present invention.
- These acetal compounds are excellent in sustained release of hexanal, 2-hexenal or 3-hexenal, have low odor, and have high water solubility and a high component (R 2 (OH) 2 ) remaining after hydrolysis. It is because it becomes a component of low environmental impact.
- the acetal compound itself since the acetal compound itself has a hydroxyl group, the water-solubility of the acetal compound can be secured, and the acetal compound can exist stably without being hydrolyzed in a neutral aqueous solution.
- the antibacterial agent of the present invention containing the acetal compound described above has a MIC (minimum growth inhibitory concentration) of 800 ⁇ g / mL or less for two or more bacteria selected from the group consisting of Escherichia coli, Staphylococcus aureus, MRSA and Salmonella. It is preferable that it is 700 ⁇ g / mL or less.
- the antibacterial agent of the present invention containing the acetal compound described above preferably has an inactivation ability higher than that of ethanol against non-enveloped viruses.
- the amount of the acetal compound contained in the antibacterial agent of the present invention is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, and 1% by mass or more. More preferably, it is preferably 90% by mass or less, and more preferably 50% by mass or less. This is because if the content of the acetal compound in the antibacterial agent is not less than the above lower limit value, the antibacterial effect can be exhibited over a sufficiently long time. In addition, if the content of the acetal compound in the antibacterial agent is not more than the above upper limit, the amount of hexanal, 2-hexenal or 3-hexenal released by hydrolysis is set to an appropriate amount, and the generation of odor is sufficiently suppressed. Because it can be done.
- the acetal compound described above is not particularly limited.
- the aldehyde hexanal, cis-2-hexenal, trans-2-hexenal, cis-3-hexenal represented by the general formula: R 1 CHO described above is used.
- trans-3-hexenal or a derivative thereof in the presence of an acid catalyst by condensing the compound represented by the above general formula: R 2 (OH) 2 .
- examples of the aldehyde derivatives described above include 2-hexenal dialkyl acetals obtained by condensing 2-hexenal or 3-hexenal, which are oxidative and unstable aldehydes, and a monohydric alcohol, and 3- Examples include hexenal dialkyl acetal.
- the acid catalyst described above is not particularly limited, and examples thereof include 10-camphorsulfonic acid.
- the condensation reaction described above can be performed in a solvent such as N, N-dimethylformamide.
- any solvent that can dissolve or disperse the acetal compound described above can be used.
- the solvent is not particularly limited, and examples thereof include water and organic solvents such as ethanol. Among these, water is preferable as the solvent from the viewpoint of improving the safety and handling properties of the antibacterial agent.
- the carrier that can be optionally contained in the antibacterial agent of the present invention any carrier capable of supporting the acetal compound described above can be used.
- the carrier is not particularly limited, and for example, porous materials such as zeolite and activated carbon, gel materials such as agar and gelatin, paper such as filter paper, nonwoven fabrics and woven fabrics can be used.
- a method for supporting the acetal compound on the carrier a known method such as impregnation or mixed dispersion can be used.
- the additive that the antibacterial agent of the present invention can optionally contain is not particularly limited, and examples thereof include a surfactant, a colorant, a viscosity modifier, an antioxidant, and a pH adjuster.
- the antibacterial method of this invention includes the process (hydrolysis process) which hydrolyzes the acetal compound represented by the general formula (I) mentioned above, hydrolyzes the acetal compound contained in the antibacterial agent, An antibacterial effect is obtained by producing R 1 CHO (hexanal, 2-hexenal or 3-hexenal) as an antibacterial component.
- the antibacterial object can be antibacterial.
- the method of bringing the antibacterial agent of the present invention into direct contact with the antibacterial object is not particularly limited.
- a liquid antibacterial agent obtained by dissolving or dispersing an acetal compound in a solvent is applied to the antibacterial object.
- a method of spraying and drying the antibacterial agent optionally applied or sprayed and a method of bringing a solid antibacterial agent having an acetal compound supported on a carrier into contact with an antibacterial object are included.
- the method for disposing the antibacterial agent of the present invention around the antibacterial object is not particularly limited.
- a liquid antibacterial agent obtained by dissolving or dispersing an acetal compound in a solvent is used around the antibacterial object.
- a method of drying an antibacterial agent that is optionally applied or spread, and a method of disposing a solid antibacterial agent having an acetal compound supported on a carrier around an antibacterial object is not particularly limited.
- a known hydrolysis method can be used. Specifically, the hydrolysis of the acetal compound may naturally proceed, for example, with water contained in the antibacterial agent or water present in the surrounding environment, or a solution containing water with respect to the antibacterial agent. You may make it progress by adding. Further, the acetal compound may be hydrolyzed in the presence of a hydrolyzing bacterium. In addition, hydrolysis of an acetal compound can be accelerated
- Example 2 A filter paper carrying compound 2 was prepared in the same manner as in Example 1 except that compound 2 was used in place of compound 1, and the growth of mycelia was observed. As a result, no mycelium growth was observed. In addition, when the strength of the odor was confirmed before and after the culture, the odor was not observed before the culture, and after the culture, the odor was moderately aromatic as compared with the aldehyde alone.
- the antibacterial and odor confirmation results are summarized in Table 1.
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Abstract
The present invention addresses the problem of providing an antibacterial agent which can release hexanal, 2-hexenal or 3-hexenal therefrom as an antibacterial component, has a reduced odor, and has excellent sustainability of the antibacterial effect thereof. The antibacterial agent according to the present invention contains an acetal compound represented by general formula (I). In formula (I), R1 represents an n-pentyl group, a 1-pentenyl group or a 2-pentenyl group, and R2 represents a bivalent organic group.
Description
本発明は、抗菌剤および抗菌方法に関し、特には、抗菌成分の放出が可能な抗菌剤および当該抗菌剤を用いた抗菌方法に関するものである。
The present invention relates to an antibacterial agent and an antibacterial method, and particularly to an antibacterial agent capable of releasing an antibacterial component and an antibacterial method using the antibacterial agent.
近年、抗菌作用を有する天然物として、ヘキサナール、２－ヘキセナール、３－ヘキセナールなどの炭素数６のアルデヒド化合物が注目されている（例えば、非特許文献１参照）。
Recently, aldehyde compounds having 6 carbon atoms such as hexanal, 2-hexenal, and 3-hexenal have attracted attention as natural products having antibacterial activity (see, for example, Non-Patent Document 1).
そして、非特許文献１には、上記炭素数６のアルデヒド化合物、および、α－シクロデキストリンの空孔部分に上記炭素数６のアルデヒド化合物を包接してなる包接錯体が優れた抗菌効果を発揮することが開示されている。
In Non-Patent Document 1, the above-mentioned aldehyde compound having 6 carbon atoms and the inclusion complex in which the aldehyde compound having 6 carbon atoms is included in the pore portion of α-cyclodextrin exhibit excellent antibacterial effects. Is disclosed.
しかし、抗菌成分としてヘキサナール、２－ヘキセナールまたは３－ヘキセナールをそのままの状態で含む抗菌剤には、臭気が強く、使用し難いという点において問題があった。
また、ヘキサナール、２－ヘキセナールまたは３－ヘキセナールをそのままの状態で含む抗菌剤、並びに、ヘキサナール、２－ヘキセナールまたは３－ヘキセナールをα－シクロデキストリンで包接してなる包接錯体を用いた抗菌剤には、抗菌効果の持続性が十分ではないという点において改善の余地があった。 However, the antibacterial agent containing hexanal, 2-hexenal or 3-hexenal as it is as an antibacterial component has a problem in that it has a strong odor and is difficult to use.
In addition, an antibacterial agent containing hexanal, 2-hexenal or 3-hexenal as it is, and an antibacterial agent using an inclusion complex formed by inclusion of hexanal, 2-hexenal or 3-hexenal with α-cyclodextrin However, there was room for improvement in that the antimicrobial effect was not sufficiently durable.
また、ヘキサナール、２－ヘキセナールまたは３－ヘキセナールをそのままの状態で含む抗菌剤、並びに、ヘキサナール、２－ヘキセナールまたは３－ヘキセナールをα－シクロデキストリンで包接してなる包接錯体を用いた抗菌剤には、抗菌効果の持続性が十分ではないという点において改善の余地があった。 However, the antibacterial agent containing hexanal, 2-hexenal or 3-hexenal as it is as an antibacterial component has a problem in that it has a strong odor and is difficult to use.
In addition, an antibacterial agent containing hexanal, 2-hexenal or 3-hexenal as it is, and an antibacterial agent using an inclusion complex formed by inclusion of hexanal, 2-hexenal or 3-hexenal with α-cyclodextrin However, there was room for improvement in that the antimicrobial effect was not sufficiently durable.
そこで、本発明は、抗菌成分としてヘキサナール、２－ヘキセナールまたは３－ヘキセナールを放出可能な抗菌剤であって、臭気が抑制され、且つ、抗菌効果の持続性に優れた抗菌剤を提供することを目的とする。
また、本発明は、上記抗菌剤を用いた抗菌方法を提供することを目的とする。 Therefore, the present invention provides an antibacterial agent capable of releasing hexanal, 2-hexenal or 3-hexenal as an antibacterial component, which is capable of suppressing odor and having an excellent antibacterial effect. Objective.
Another object of the present invention is to provide an antibacterial method using the antibacterial agent.
また、本発明は、上記抗菌剤を用いた抗菌方法を提供することを目的とする。 Therefore, the present invention provides an antibacterial agent capable of releasing hexanal, 2-hexenal or 3-hexenal as an antibacterial component, which is capable of suppressing odor and having an excellent antibacterial effect. Objective.
Another object of the present invention is to provide an antibacterial method using the antibacterial agent.
本発明者らは、上記目的を達成するために鋭意検討を行った。そして、本発明者らは、所定のアセタール化合物を含む抗菌剤が、抗菌成分としてヘキサナール、２－ヘキセナールまたは３－ヘキセナールを放出可能であり、更に、臭気が抑制されていると共に抗菌効果の持続性に優れていることを見出し、本発明を完成させた。
The present inventors have intensively studied to achieve the above object. The inventors of the present invention can release hexanal, 2-hexenal or 3-hexenal as an antibacterial component by an antibacterial agent containing a predetermined acetal compound, and further, the odor is suppressed and the antibacterial effect is sustained. The present invention was completed.
即ち、この発明は、上記課題を有利に解決することを目的とするものであり、本発明の抗菌剤は、下記一般式（Ｉ）：
［式（Ｉ）中、Ｒ1は、ｎ－ペンチル基、１－ペンテニル基または２－ペンテニル基であり、Ｒ2は、２価の有機基である。］で表されるアセタール化合物を含むことを特徴とする。上記一般式（Ｉ）で表されるアセタール化合物は、加水分解すると、Ｒ1ＣＨＯと、Ｒ2（ＯＨ）2とを生成する。従って、上記一般式（Ｉ）で表されるアセタール化合物を含有させれば、臭気を抑制しつつ、アセタール化合物の加水分解によりヘキサナール、２－ヘキセナールまたは３－ヘキセナールを徐放させて抗菌効果を持続的に得ることができる。
That is, this invention aims at solving the said subject advantageously, and the antibacterial agent of this invention is the following general formula (I):
[In the formula (I), R 1 is an n-pentyl group, 1-pentenyl group or 2-pentenyl group, and R 2 is a divalent organic group. An acetal compound represented by the formula: The acetal compound represented by the general formula (I) generates R 1 CHO and R 2 (OH) 2 when hydrolyzed. Therefore, when the acetal compound represented by the above general formula (I) is contained, the antibacterial effect is sustained by gradually releasing hexanal, 2-hexenal or 3-hexenal by hydrolysis of the acetal compound while suppressing odor. Can be obtained.
ここで、本発明の抗菌剤は、前記Ｒ2が、グリセリン、ペンチルグリセリルエーテル、２－エチルヘキシルグリセリルエーテル、エチレングリコール、ブタンジオール、ペンタンジオール、ヘキサンジオール、ヘプタンジオール、オクタンジオール、ノナンジオール、デカンジオール、ドデカンジオール、ブタントリオール、ペンタントリオール、ヘキサントリオール、ヘプタントリオール、オクタントリオール、ノナントリオール、デカントリオール、ドデカントリオール、マンニトール、ソルビトール、キシリトール、３－メトキシ－１，２－プロパンジオール、シクロヘキサンジオール、グリセリン酸、イノシトール、トレイトール、アラビニトール、アルブチン、サリシン、グルコース、ガラクトース、マンノース、キシロース、フルクトース、Ｎ－アセチルグルコサミン、グルコノラクトン、マルトース、セロビオース、スクロース、ラクトースおよびラクトビオン酸からなる群より選択される化合物から水酸基を２つ除いた残基であることが好ましい。Ｒ2が上述した残基であれば、臭気の発生を十分に抑制しつつ、加水分解によるヘキサナール、２－ヘキセナールまたは３－ヘキセナールの放出を容易に行うことができるからである。
Here, in the antibacterial agent of the present invention, R 2 is glycerin, pentyl glyceryl ether, 2-ethylhexyl glyceryl ether, ethylene glycol, butanediol, pentanediol, hexanediol, heptanediol, octanediol, nonanediol, decanediol. , Dodecanediol, butanetriol, pentanetriol, hexanetriol, heptanetriol, octanetriol, nonanetriol, decanetriol, dodecanetriol, mannitol, sorbitol, xylitol, 3-methoxy-1,2-propanediol, cyclohexanediol, glyceric acid , Inositol, threitol, arabinitol, arbutin, salicin, glucose, galactose, mannose, xylose, fur Kutosu, N- acetylglucosamine, gluconolactone, maltose, cellobiose, sucrose, be two a residue obtained by removing hydroxyl groups from lactose and consisting lactobionic acid compound selected from the group preferred. This is because when R 2 is the above-described residue, the release of hexanal, 2-hexenal or 3-hexenal by hydrolysis can be easily performed while sufficiently suppressing the generation of odor.
また、本発明の抗菌剤は、前記Ｒ2が、水酸基を２つ以上含有する天然物から水酸基を２つ除いた残基であることが好ましい。Ｒ2が上述した残基であれば、アセタール化合物の加水分解により生成するＲ1ＣＨＯおよびＲ2（ＯＨ）2の双方が天然物になるため、抗菌剤の使用時に環境に与える負荷を低減することができるからである。なお、本発明において、「天然物」とは、生物が産生可能な化合物を指す。従って、「天然物」には、生物が産生可能な化合物であれば、全合成された化合物も含まれる。
In the antibacterial agent of the present invention, R 2 is preferably a residue obtained by removing two hydroxyl groups from a natural product containing two or more hydroxyl groups. If R 2 is the above-mentioned residue, both R 1 CHO and R 2 (OH) 2 produced by hydrolysis of the acetal compound are natural products, so the load on the environment when using antibacterial agents is reduced. Because it can. In the present invention, “natural product” refers to a compound that can be produced by an organism. Therefore, the “natural product” includes a compound that is totally synthesized as long as it is a compound that can be produced by an organism.
更に、本発明の抗菌剤は、前記Ｒ2が、水酸基を２つ以上含有する水溶性化合物から水酸基を２つ除いた残基であることが好ましい。Ｒ2が上述した残基であれば、アセタール化合物の加水分解により生成するＲ2（ＯＨ）2が水溶性を有するため、抗菌剤の使用後に残留する成分を水洗により容易に除去することができるからである。なお、本発明において、「水溶性化合物」とは、水に対する溶解度が、２５℃において１０ｇ／１００ｇ－Ｈ2Ｏ以上である化合物を指す。
Furthermore, in the antibacterial agent of the present invention, R 2 is preferably a residue obtained by removing two hydroxyl groups from a water-soluble compound containing two or more hydroxyl groups. If R 2 is the above-mentioned residue, R 2 (OH) 2 produced by hydrolysis of the acetal compound is water-soluble, so that components remaining after use of the antibacterial agent can be easily removed by washing with water. Because. In the present invention, “water-soluble compound” refers to a compound having a solubility in water of 10 g / 100 g-H 2 O or more at 25 ° C.
また、本発明の抗菌剤は、前記Ｒ2の炭素数が２以上であることが好ましい。Ｒ2の炭素数が２以上であれば、臭気の発生を十分に抑制することができるからである。
In the antibacterial agent of the present invention, R 2 preferably has 2 or more carbon atoms. This is because if the carbon number of R 2 is 2 or more, the generation of odor can be sufficiently suppressed.
更に、本発明の抗菌剤は、前記Ｒ2が非置換のアミノ基を有さないことが好ましい。Ｒ2が非置換のアミノ基（－ＮＨ2）を有さないアセタール化合物は、合成が容易だからである。
Furthermore, in the antibacterial agent of the present invention, it is preferable that R 2 does not have an unsubstituted amino group. This is because an acetal compound in which R 2 does not have an unsubstituted amino group (—NH 2 ) is easy to synthesize.
また、この発明は、上記課題を有利に解決することを目的とするものであり、本発明の抗菌方法は、上述した抗菌剤の何れかを使用し、前記アセタール化合物を加水分解する工程を含むことを特徴とする。上記一般式（Ｉ）で表されるアセタール化合物を加水分解すれば、臭気を抑制しつつ、ヘキサナール、２－ヘキセナールまたは３－ヘキセナールを徐放させて抗菌効果を持続的に得ることができる。
Moreover, this invention aims at solving the said subject advantageously, The antibacterial method of this invention includes the process of hydrolyzing the said acetal compound using any of the antibacterial agents mentioned above. It is characterized by that. If the acetal compound represented by the general formula (I) is hydrolyzed, the antibacterial effect can be continuously obtained by gradually releasing hexanal, 2-hexenal or 3-hexenal while suppressing odor.
本発明によれば、抗菌成分としてヘキサナール、２－ヘキセナールまたは３－ヘキセナールを放出可能であり、更に、臭気が抑制され、且つ、抗菌効果の持続性にも優れた抗菌剤を提供することができる。
また、本発明によれば、臭気を抑制しつつ、ヘキサナール、２－ヘキセナールまたは３－ヘキセナールを徐放させて抗菌効果を持続的に得ることができる。 According to the present invention, it is possible to provide an antibacterial agent capable of releasing hexanal, 2-hexenal, or 3-hexenal as an antibacterial component, further suppressing odor, and having excellent antibacterial effects. .
Furthermore, according to the present invention, the antibacterial effect can be continuously obtained by gradually releasing hexanal, 2-hexenal or 3-hexenal while suppressing odor.
また、本発明によれば、臭気を抑制しつつ、ヘキサナール、２－ヘキセナールまたは３－ヘキセナールを徐放させて抗菌効果を持続的に得ることができる。 According to the present invention, it is possible to provide an antibacterial agent capable of releasing hexanal, 2-hexenal, or 3-hexenal as an antibacterial component, further suppressing odor, and having excellent antibacterial effects. .
Furthermore, according to the present invention, the antibacterial effect can be continuously obtained by gradually releasing hexanal, 2-hexenal or 3-hexenal while suppressing odor.
以下、本発明の実施形態について詳細に説明する。
ここで、本発明の抗菌剤は、微生物（カビおよび／または細菌）の発生、生育または増殖を抑制し得る抗菌成分として、ヘキサナール（ＣＨ3ＣＨ2ＣＨ2ＣＨ2ＣＨ2ＣＨＯ）、２－ヘキセナール（ＣＨ3ＣＨ2ＣＨ2ＣＨ＝ＣＨＣＨＯ）または３－ヘキセナール（ＣＨ3ＣＨ2ＣＨ＝ＣＨＣＨ2ＣＨＯ）を放出可能なものである。そして、本発明の抗菌剤は、特に限定されることなく、例えば、抗菌加工製品を製造する際や、病院、介護施設、保育施設、食品工場、一般家庭内などにおいて各種製品に抗菌機能を付与する際に、製品の表面に塗布または散布して使用することができる。なお、本発明の抗菌剤は、抗ウィルス活性を更に有していてもよい。
また、本発明の抗菌方法は、本発明の抗菌剤を使用することを特徴とする。 Hereinafter, embodiments of the present invention will be described in detail.
Here, the antibacterial agent of the present invention has hexanal (CH 3 CH 2 CH 2 CH 2 CH 2 CHO), 2-hexenal as an antibacterial component capable of suppressing the generation, growth or proliferation of microorganisms (mold and / or bacteria). (CH 3 CH 2 CH 2 CH═CHCHO) or 3-hexenal (CH 3 CH 2 CH═CHCH 2 CHO) can be released. The antibacterial agent of the present invention is not particularly limited. For example, when an antibacterial processed product is manufactured, and an antibacterial function is imparted to various products in hospitals, nursing homes, childcare facilities, food factories, general homes, etc. When applied, it can be applied or sprayed on the surface of the product. The antibacterial agent of the present invention may further have antiviral activity.
The antibacterial method of the present invention is characterized by using the antibacterial agent of the present invention.
ここで、本発明の抗菌剤は、微生物（カビおよび／または細菌）の発生、生育または増殖を抑制し得る抗菌成分として、ヘキサナール（ＣＨ3ＣＨ2ＣＨ2ＣＨ2ＣＨ2ＣＨＯ）、２－ヘキセナール（ＣＨ3ＣＨ2ＣＨ2ＣＨ＝ＣＨＣＨＯ）または３－ヘキセナール（ＣＨ3ＣＨ2ＣＨ＝ＣＨＣＨ2ＣＨＯ）を放出可能なものである。そして、本発明の抗菌剤は、特に限定されることなく、例えば、抗菌加工製品を製造する際や、病院、介護施設、保育施設、食品工場、一般家庭内などにおいて各種製品に抗菌機能を付与する際に、製品の表面に塗布または散布して使用することができる。なお、本発明の抗菌剤は、抗ウィルス活性を更に有していてもよい。
また、本発明の抗菌方法は、本発明の抗菌剤を使用することを特徴とする。 Hereinafter, embodiments of the present invention will be described in detail.
Here, the antibacterial agent of the present invention has hexanal (CH 3 CH 2 CH 2 CH 2 CH 2 CHO), 2-hexenal as an antibacterial component capable of suppressing the generation, growth or proliferation of microorganisms (mold and / or bacteria). (CH 3 CH 2 CH 2 CH═CHCHO) or 3-hexenal (CH 3 CH 2 CH═CHCH 2 CHO) can be released. The antibacterial agent of the present invention is not particularly limited. For example, when an antibacterial processed product is manufactured, and an antibacterial function is imparted to various products in hospitals, nursing homes, childcare facilities, food factories, general homes, etc. When applied, it can be applied or sprayed on the surface of the product. The antibacterial agent of the present invention may further have antiviral activity.
The antibacterial method of the present invention is characterized by using the antibacterial agent of the present invention.
（抗菌剤）
本発明の抗菌剤は、下記の一般式（Ｉ）：
［式（Ｉ）中、Ｒ1は、ｎ－ペンチル基（－ＣＨ2ＣＨ2ＣＨ2ＣＨ2ＣＨ3）、１－ペンテニル基（－ＣＨ＝ＣＨＣＨ2ＣＨ2ＣＨ3）または２－ペンテニル基（－ＣＨ2ＣＨ＝ＣＨＣＨ2ＣＨ3）であり、Ｒ2は、２価の有機基である。］で表されるアセタール化合物を含有する。なお、本発明の抗菌剤は、任意に、アセタール化合物を溶解または分散する溶媒、アセタール化合物を担持する担体および添加剤からなる群より選択される少なくとも一つを更に含有していてもよい。
(Antimicrobial agent)
The antibacterial agent of the present invention has the following general formula (I):
[In the formula (I), R 1 represents an n-pentyl group (—CH 2 CH 2 CH 2 CH 2 CH 3 ), a 1-pentenyl group (—CH═CHCH 2 CH 2 CH 3 ) or a 2-pentenyl group ( —CH 2 CH═CHCH 2 CH 3 ), and R 2 is a divalent organic group. An acetal compound represented by the formula: The antibacterial agent of the present invention may optionally further contain at least one selected from the group consisting of a solvent for dissolving or dispersing the acetal compound, a carrier supporting the acetal compound, and an additive.
本発明の抗菌剤は、下記の一般式（Ｉ）：
The antibacterial agent of the present invention has the following general formula (I):
＜アセタール化合物＞
本発明の抗菌剤に含まれるアセタール化合物は、上記一般式（Ｉ）で表される、環状構造を有するアセタール化合物である。そして、上記一般式（Ｉ）で表されるアセタール化合物は、加水分解により、一般式：Ｒ1ＣＨＯで表されるアルデヒド（ヘキサナール、ｃｉｓ－２－ヘキセナール、ｔｒａｎｓ－２－ヘキセナール、ｃｉｓ－３－ヘキセナールまたはｔｒａｎｓ－３－ヘキセナール）と、一般式：Ｒ2（ＯＨ）2で表される化合物（水酸基を２つ以上含有する化合物）とを生成し得る。従って、本発明の抗菌剤によれば、アセタール化合物の加水分解により抗菌成分としてヘキサナール、２－ヘキセナール（ｃｉｓ－２－ヘキセナールまたはｔｒａｎｓ－２－ヘキセナール）、或いは、３－ヘキセナール（ｃｉｓ－３－ヘキセナールまたはｔｒａｎｓ－３－ヘキセナール）を徐放することができるので、抗菌効果を持続的に得ることができる。また、本発明の抗菌剤によれば、臭気の強いヘキサナール、２－ヘキセナールまたは３－ヘキセナールをそのまま使用する場合と比較して、臭気を抑制することができる。なお、本発明の抗菌剤に含まれているアセタール化合物は、アルデヒドの徐放により適度な芳香を発し得るため、香料として利用することも可能である。即ち、上記一般式（Ｉ）で表されるアセタール化合物を使用すれば、当該アセタール化合物と、任意の溶媒および／または添加剤などとを含有する芳香性組成物を提供することができる。 <Acetal compound>
The acetal compound contained in the antibacterial agent of the present invention is an acetal compound having a cyclic structure represented by the above general formula (I). The acetal compound represented by the general formula (I) is converted into an aldehyde represented by the general formula: R 1 CHO (hexanal, cis-2-hexenal, trans-2-hexenal, cis-3- Hexenal or trans-3-hexenal) and a compound represented by the general formula: R 2 (OH) 2 (compound containing two or more hydroxyl groups) can be produced. Therefore, according to the antibacterial agent of the present invention, hexanal, 2-hexenal (cis-2-hexenal or trans-2-hexenal), or 3-hexenal (cis-3-hexenal) as an antibacterial component by hydrolysis of the acetal compound. Or trans-3-hexenal) can be gradually released, so that the antibacterial effect can be continuously obtained. Further, according to the antibacterial agent of the present invention, odor can be suppressed as compared with the case where hexanal, 2-hexenal or 3-hexenal having strong odor is used as it is. In addition, since the acetal compound contained in the antibacterial agent of this invention can emit a suitable fragrance by the sustained release of an aldehyde, it can also be utilized as a fragrance | flavor. That is, if the acetal compound represented by the general formula (I) is used, an aromatic composition containing the acetal compound and any solvent and / or additive can be provided.
本発明の抗菌剤に含まれるアセタール化合物は、上記一般式（Ｉ）で表される、環状構造を有するアセタール化合物である。そして、上記一般式（Ｉ）で表されるアセタール化合物は、加水分解により、一般式：Ｒ1ＣＨＯで表されるアルデヒド（ヘキサナール、ｃｉｓ－２－ヘキセナール、ｔｒａｎｓ－２－ヘキセナール、ｃｉｓ－３－ヘキセナールまたはｔｒａｎｓ－３－ヘキセナール）と、一般式：Ｒ2（ＯＨ）2で表される化合物（水酸基を２つ以上含有する化合物）とを生成し得る。従って、本発明の抗菌剤によれば、アセタール化合物の加水分解により抗菌成分としてヘキサナール、２－ヘキセナール（ｃｉｓ－２－ヘキセナールまたはｔｒａｎｓ－２－ヘキセナール）、或いは、３－ヘキセナール（ｃｉｓ－３－ヘキセナールまたはｔｒａｎｓ－３－ヘキセナール）を徐放することができるので、抗菌効果を持続的に得ることができる。また、本発明の抗菌剤によれば、臭気の強いヘキサナール、２－ヘキセナールまたは３－ヘキセナールをそのまま使用する場合と比較して、臭気を抑制することができる。なお、本発明の抗菌剤に含まれているアセタール化合物は、アルデヒドの徐放により適度な芳香を発し得るため、香料として利用することも可能である。即ち、上記一般式（Ｉ）で表されるアセタール化合物を使用すれば、当該アセタール化合物と、任意の溶媒および／または添加剤などとを含有する芳香性組成物を提供することができる。 <Acetal compound>
The acetal compound contained in the antibacterial agent of the present invention is an acetal compound having a cyclic structure represented by the above general formula (I). The acetal compound represented by the general formula (I) is converted into an aldehyde represented by the general formula: R 1 CHO (hexanal, cis-2-hexenal, trans-2-hexenal, cis-3- Hexenal or trans-3-hexenal) and a compound represented by the general formula: R 2 (OH) 2 (compound containing two or more hydroxyl groups) can be produced. Therefore, according to the antibacterial agent of the present invention, hexanal, 2-hexenal (cis-2-hexenal or trans-2-hexenal), or 3-hexenal (cis-3-hexenal) as an antibacterial component by hydrolysis of the acetal compound. Or trans-3-hexenal) can be gradually released, so that the antibacterial effect can be continuously obtained. Further, according to the antibacterial agent of the present invention, odor can be suppressed as compared with the case where hexanal, 2-hexenal or 3-hexenal having strong odor is used as it is. In addition, since the acetal compound contained in the antibacterial agent of this invention can emit a suitable fragrance by the sustained release of an aldehyde, it can also be utilized as a fragrance | flavor. That is, if the acetal compound represented by the general formula (I) is used, an aromatic composition containing the acetal compound and any solvent and / or additive can be provided.
［アセタール化合物の構造］
ここで、任意の２価の有機基であるＲ2としては、特に限定されることなく、水酸基（－ＯＨ）を２つ以上含有する化合物から水酸基を２つ除いた残基が挙げられる。具体的には、Ｒ2としては、例えば、多価アルコール若しくはその誘導体から水酸基を２つ除いた残基、または、糖類若しくはその誘導体から水酸基を２つ除いた残基が挙げられる。より具体的には、Ｒ2としては、例えば、エチレングリコール、ブタンジオール、ペンタンジオール、ヘキサンジオール、シクロヘキサンジオール、ヘプタンジオール、オクタンジオール、ノナンジオール、デカンジオールおよびドデカンジオール等の２価のアルコール、グリセリン、ブタントリオール、ペンタントリオール、ヘキサントリオール、ヘプタントリオール、オクタントリオール、ノナントリオール、デカントリオールおよびドデカントリオール等の３価のアルコール、ペンチルグリセリルエーテル、２－エチルヘキシルグリセリルエーテルおよび３－メトキシ－１，２－プロパンジオール等の３価のアルコールの誘導体、グルコース、ガラクトース、マンノース、キシロース、フルクトースおよびＮ－アセチルグルコサミン等の単糖、マルトース、セロビオース、スクロースおよびラクトース等の二糖、アルブチンおよびサリシン等の配糖体、マンニトール、ソルビトール、キシリトール、イノシトール、トレイトールおよびアラビニトール等の糖アルコール、グリセリン酸およびラクトビオン酸等の糖酸、並びに、グルコノラクトンからなる群より選択される化合物から水酸基を２つ除いた残基が挙げられる。そして、Ｒ2が上述した化合物から水酸基を２つ除いた残基であれば、臭気の発生を十分に抑制しつつ、加水分解によるヘキサナール、２－ヘキセナールまたは３－ヘキセナールの放出を容易に行うことができる。 [Structure of acetal compound]
Here, R 2 which is an arbitrary divalent organic group is not particularly limited, and examples thereof include a residue obtained by removing two hydroxyl groups from a compound containing two or more hydroxyl groups (—OH). Specifically, examples of R 2 include a residue obtained by removing two hydroxyl groups from a polyhydric alcohol or a derivative thereof, or a residue obtained by removing two hydroxyl groups from a saccharide or a derivative thereof. More specifically, examples of R 2 include divalent alcohols such as ethylene glycol, butanediol, pentanediol, hexanediol, cyclohexanediol, heptanediol, octanediol, nonanediol, decanediol, and dodecanediol, and glycerin. , Trivalent alcohols such as butanetriol, pentanetriol, hexanetriol, heptanetriol, octanetriol, nonanetriol, decanetriol and dodecanetriol, pentylglyceryl ether, 2-ethylhexylglyceryl ether and 3-methoxy-1,2-propane Trivalent alcohol derivatives such as diols, glucose, galactose, mannose, xylose, fructose, N-acetylglucosamine, etc. Monosaccharides, disaccharides such as maltose, cellobiose, sucrose and lactose, glycosides such as arbutin and salicin, sugar alcohols such as mannitol, sorbitol, xylitol, inositol, threitol and arabinitol, sugar acids such as glyceric acid and lactobionic acid And a residue obtained by removing two hydroxyl groups from a compound selected from the group consisting of gluconolactone. If R 2 is a residue obtained by removing two hydroxyl groups from the above compound, the release of hexanal, 2-hexenal or 3-hexenal by hydrolysis can be easily performed while sufficiently suppressing the generation of odor. Can do.
ここで、任意の２価の有機基であるＲ2としては、特に限定されることなく、水酸基（－ＯＨ）を２つ以上含有する化合物から水酸基を２つ除いた残基が挙げられる。具体的には、Ｒ2としては、例えば、多価アルコール若しくはその誘導体から水酸基を２つ除いた残基、または、糖類若しくはその誘導体から水酸基を２つ除いた残基が挙げられる。より具体的には、Ｒ2としては、例えば、エチレングリコール、ブタンジオール、ペンタンジオール、ヘキサンジオール、シクロヘキサンジオール、ヘプタンジオール、オクタンジオール、ノナンジオール、デカンジオールおよびドデカンジオール等の２価のアルコール、グリセリン、ブタントリオール、ペンタントリオール、ヘキサントリオール、ヘプタントリオール、オクタントリオール、ノナントリオール、デカントリオールおよびドデカントリオール等の３価のアルコール、ペンチルグリセリルエーテル、２－エチルヘキシルグリセリルエーテルおよび３－メトキシ－１，２－プロパンジオール等の３価のアルコールの誘導体、グルコース、ガラクトース、マンノース、キシロース、フルクトースおよびＮ－アセチルグルコサミン等の単糖、マルトース、セロビオース、スクロースおよびラクトース等の二糖、アルブチンおよびサリシン等の配糖体、マンニトール、ソルビトール、キシリトール、イノシトール、トレイトールおよびアラビニトール等の糖アルコール、グリセリン酸およびラクトビオン酸等の糖酸、並びに、グルコノラクトンからなる群より選択される化合物から水酸基を２つ除いた残基が挙げられる。そして、Ｒ2が上述した化合物から水酸基を２つ除いた残基であれば、臭気の発生を十分に抑制しつつ、加水分解によるヘキサナール、２－ヘキセナールまたは３－ヘキセナールの放出を容易に行うことができる。 [Structure of acetal compound]
Here, R 2 which is an arbitrary divalent organic group is not particularly limited, and examples thereof include a residue obtained by removing two hydroxyl groups from a compound containing two or more hydroxyl groups (—OH). Specifically, examples of R 2 include a residue obtained by removing two hydroxyl groups from a polyhydric alcohol or a derivative thereof, or a residue obtained by removing two hydroxyl groups from a saccharide or a derivative thereof. More specifically, examples of R 2 include divalent alcohols such as ethylene glycol, butanediol, pentanediol, hexanediol, cyclohexanediol, heptanediol, octanediol, nonanediol, decanediol, and dodecanediol, and glycerin. , Trivalent alcohols such as butanetriol, pentanetriol, hexanetriol, heptanetriol, octanetriol, nonanetriol, decanetriol and dodecanetriol, pentylglyceryl ether, 2-ethylhexylglyceryl ether and 3-methoxy-1,2-propane Trivalent alcohol derivatives such as diols, glucose, galactose, mannose, xylose, fructose, N-acetylglucosamine, etc. Monosaccharides, disaccharides such as maltose, cellobiose, sucrose and lactose, glycosides such as arbutin and salicin, sugar alcohols such as mannitol, sorbitol, xylitol, inositol, threitol and arabinitol, sugar acids such as glyceric acid and lactobionic acid And a residue obtained by removing two hydroxyl groups from a compound selected from the group consisting of gluconolactone. If R 2 is a residue obtained by removing two hydroxyl groups from the above compound, the release of hexanal, 2-hexenal or 3-hexenal by hydrolysis can be easily performed while sufficiently suppressing the generation of odor. Can do.
ここで、アセタール化合物の合成時およびアセタール化合物の加水分解時の立体障害を小さくする観点からは、Ｒ2は、下記の一般式（ＩＩ）または（ＩＩＩ）：
［式（ＩＩ）および式（ＩＩＩ）中、Ｒ3、Ｒ4およびＲ5は、水素原子または有機基であり、互いに同一でも異なっていてもよく、また、２つ以上が互いに結合して環構造を形成していてもよく、「＊」は結合手であることを示す。］
で表される基であることが好ましい。即ち、上述した化合物から水酸基を２つ除いた残基は、上記一般式（ＩＩ）または（ＩＩＩ）で表される構造を有することが好ましい。 Here, from the viewpoint of reducing the steric hindrance during the synthesis of the acetal compound and during the hydrolysis of the acetal compound, R 2 represents the following general formula (II) or (III):
[In the formulas (II) and (III), R 3 , R 4 and R 5 are hydrogen atoms or organic groups, which may be the same or different from each other, and two or more are bonded to each other to form a ring. A structure may be formed, and “*” indicates a bond. ]
It is preferable that it is group represented by these. That is, the residue obtained by removing two hydroxyl groups from the compound described above preferably has a structure represented by the general formula (II) or (III).
で表される基であることが好ましい。即ち、上述した化合物から水酸基を２つ除いた残基は、上記一般式（ＩＩ）または（ＩＩＩ）で表される構造を有することが好ましい。 Here, from the viewpoint of reducing the steric hindrance during the synthesis of the acetal compound and during the hydrolysis of the acetal compound, R 2 represents the following general formula (II) or (III):
It is preferable that it is group represented by these. That is, the residue obtained by removing two hydroxyl groups from the compound described above preferably has a structure represented by the general formula (II) or (III).
また、抗菌剤の使用時に環境に与える負荷を低減する観点からは、Ｒ2は、水酸基を２つ以上含有する天然物から水酸基を２つ除いた残基であることが好ましい。Ｒ2が天然物から水酸基を２つ除いた残基であれば、アセタール化合物の加水分解により生成するＲ1ＣＨＯ（ヘキサナール、２－ヘキセナールまたは３－ヘキセナール）とＲ2（ＯＨ）2との双方が天然物になるので、抗菌剤の使用後に残留する成分が環境に与える負荷を低減することができる。
ここで、水酸基を２つ以上含有する天然物としては、特に限定されることなく、例えば、マンニトール、ソルビトール、キシリトール、グリセリン酸、イノシトール、アラビニトール、アルブチン、サリシン、Ｄ－グルコース、Ｌ－グルコース、Ｄ－ガラクトース、Ｄ－マンノース、Ｄ－キシロース、Ｄ－フルクトース、Ｎ－アセチル－Ｄ－グルコサミン、グルコノラクトン、Ｄ－マルトース、Ｄ－セロビオース、Ｄ－スクロース、Ｄ－ラクトース、ラクトビオン酸などが挙げられる。 From the viewpoint of reducing the load on the environment when using the antibacterial agent, R 2 is preferably a residue obtained by removing two hydroxyl groups from a natural product containing two or more hydroxyl groups. If R 2 is a residue obtained by removing two hydroxyl groups from a natural product, both R 1 CHO (hexanal, 2-hexenal or 3-hexenal) produced by hydrolysis of an acetal compound and R 2 (OH) 2 Since this becomes a natural product, it is possible to reduce the burden on the environment of components remaining after the use of the antibacterial agent.
Here, the natural product containing two or more hydroxyl groups is not particularly limited. For example, mannitol, sorbitol, xylitol, glyceric acid, inositol, arabinitol, arbutin, salicin, D-glucose, L-glucose, D -Galactose, D-mannose, D-xylose, D-fructose, N-acetyl-D-glucosamine, gluconolactone, D-maltose, D-cellobiose, D-sucrose, D-lactose, lactobionic acid and the like.
ここで、水酸基を２つ以上含有する天然物としては、特に限定されることなく、例えば、マンニトール、ソルビトール、キシリトール、グリセリン酸、イノシトール、アラビニトール、アルブチン、サリシン、Ｄ－グルコース、Ｌ－グルコース、Ｄ－ガラクトース、Ｄ－マンノース、Ｄ－キシロース、Ｄ－フルクトース、Ｎ－アセチル－Ｄ－グルコサミン、グルコノラクトン、Ｄ－マルトース、Ｄ－セロビオース、Ｄ－スクロース、Ｄ－ラクトース、ラクトビオン酸などが挙げられる。 From the viewpoint of reducing the load on the environment when using the antibacterial agent, R 2 is preferably a residue obtained by removing two hydroxyl groups from a natural product containing two or more hydroxyl groups. If R 2 is a residue obtained by removing two hydroxyl groups from a natural product, both R 1 CHO (hexanal, 2-hexenal or 3-hexenal) produced by hydrolysis of an acetal compound and R 2 (OH) 2 Since this becomes a natural product, it is possible to reduce the burden on the environment of components remaining after the use of the antibacterial agent.
Here, the natural product containing two or more hydroxyl groups is not particularly limited. For example, mannitol, sorbitol, xylitol, glyceric acid, inositol, arabinitol, arbutin, salicin, D-glucose, L-glucose, D -Galactose, D-mannose, D-xylose, D-fructose, N-acetyl-D-glucosamine, gluconolactone, D-maltose, D-cellobiose, D-sucrose, D-lactose, lactobionic acid and the like.
更に、抗菌剤の使用後に残留する成分を容易に除去し得るようにする観点からは、Ｒ2は、水酸基を２つ以上含有する水溶性化合物から水酸基を２つ除いた残基であることが好ましい。Ｒ2が水溶性化合物から水酸基を２つ除いた残基であれば、アセタール化合物の加水分解により生成するＲ2（ＯＨ）2が水溶性化合物となり、抗菌剤の使用後に残留する成分を水洗により容易に除去することが可能となる。
なお、抗菌剤の使用後に残留する成分を更に容易に水洗し得るようにする観点からは、上記水溶性化合物の水に対する溶解度は、２５℃において１０ｇ／１００ｇ－Ｈ2Ｏ以上であることが好ましく、１５ｇ／１００ｇ－Ｈ2Ｏ以上であることがより好ましい。また、上記水溶性化合物の水に対する溶解度は、２５℃において２００ｇ／１００ｇ－Ｈ2Ｏ以下であることが好ましく、１８０ｇ／１００ｇ－Ｈ2Ｏ以下であることがより好ましい。
ここで、水酸基を２つ以上含有する水溶性化合物としては、特に限定されることなく、例えば、Ｄ－グルコース（９１）、Ｄ－ラクトース（２１）、アルブチン（１３）、グルコノラクトン（５０）（カッコ内の数値は水１００ｇに対する温度２５℃での溶解度［単位：ｇ／１００ｇ－Ｈ2Ｏ］である。）などが挙げられる。 Furthermore, from the viewpoint of easily removing components remaining after use of the antibacterial agent, R 2 is a residue obtained by removing two hydroxyl groups from a water-soluble compound containing two or more hydroxyl groups. preferable. If R 2 is a residue obtained by removing two hydroxyl groups from a water-soluble compound, R 2 (OH) 2 produced by hydrolysis of the acetal compound becomes a water-soluble compound, and the components remaining after use of the antibacterial agent are washed with water. It can be easily removed.
From the viewpoint of facilitating washing of the components remaining after the use of the antibacterial agent, the solubility of the water-soluble compound in water is preferably 10 g / 100 g-H 2 O or more at 25 ° C. 15 g / 100 g-H 2 O or more is more preferable. The solubility of the water-soluble compound in water is preferably 200 g / 100 g-H 2 O or less at 25 ° C., more preferably 180 g / 100 g-H 2 O or less.
Here, the water-soluble compound containing two or more hydroxyl groups is not particularly limited, and examples thereof include D-glucose (91), D-lactose (21), arbutin (13), and gluconolactone (50). (Numerical values in parentheses are solubility in 100 g of water at a temperature of 25 ° C. [unit: g / 100 g-H 2 O]).
なお、抗菌剤の使用後に残留する成分を更に容易に水洗し得るようにする観点からは、上記水溶性化合物の水に対する溶解度は、２５℃において１０ｇ／１００ｇ－Ｈ2Ｏ以上であることが好ましく、１５ｇ／１００ｇ－Ｈ2Ｏ以上であることがより好ましい。また、上記水溶性化合物の水に対する溶解度は、２５℃において２００ｇ／１００ｇ－Ｈ2Ｏ以下であることが好ましく、１８０ｇ／１００ｇ－Ｈ2Ｏ以下であることがより好ましい。
ここで、水酸基を２つ以上含有する水溶性化合物としては、特に限定されることなく、例えば、Ｄ－グルコース（９１）、Ｄ－ラクトース（２１）、アルブチン（１３）、グルコノラクトン（５０）（カッコ内の数値は水１００ｇに対する温度２５℃での溶解度［単位：ｇ／１００ｇ－Ｈ2Ｏ］である。）などが挙げられる。 Furthermore, from the viewpoint of easily removing components remaining after use of the antibacterial agent, R 2 is a residue obtained by removing two hydroxyl groups from a water-soluble compound containing two or more hydroxyl groups. preferable. If R 2 is a residue obtained by removing two hydroxyl groups from a water-soluble compound, R 2 (OH) 2 produced by hydrolysis of the acetal compound becomes a water-soluble compound, and the components remaining after use of the antibacterial agent are washed with water. It can be easily removed.
From the viewpoint of facilitating washing of the components remaining after the use of the antibacterial agent, the solubility of the water-soluble compound in water is preferably 10 g / 100 g-H 2 O or more at 25 ° C. 15 g / 100 g-H 2 O or more is more preferable. The solubility of the water-soluble compound in water is preferably 200 g / 100 g-H 2 O or less at 25 ° C., more preferably 180 g / 100 g-H 2 O or less.
Here, the water-soluble compound containing two or more hydroxyl groups is not particularly limited, and examples thereof include D-glucose (91), D-lactose (21), arbutin (13), and gluconolactone (50). (Numerical values in parentheses are solubility in 100 g of water at a temperature of 25 ° C. [unit: g / 100 g-H 2 O]).
また、臭気の発生を十分に抑制する観点からは、Ｒ2の炭素数は、２以上であることが好ましく、６以上であることがより好ましい。Ｒ2の炭素数が上記下限値以上であれば、アセタール化合物の揮発性を低下させて、臭気の発生を十分に抑制することができる。なお、アセタール化合物およびアセタール化合物の加水分解により生成するＲ2（ＯＨ）2の水溶性を高める観点からは、Ｒ2の炭素数は、６０以下であることが好ましく、３０以下であることがより好ましい。
Further, from the viewpoint of sufficiently suppressing the generation of odor, the carbon number of R 2 is preferably 2 or more, and more preferably 6 or more. If the carbon number of R 2 is not less than the above lower limit, the volatility of the acetal compound can be reduced and the generation of odor can be sufficiently suppressed. From the viewpoint of increasing the water solubility of R 2 (OH) 2 produced by hydrolysis of the acetal compound and the acetal compound, the carbon number of R 2 is preferably 60 or less, and more preferably 30 or less. preferable.
更に、Ｒ2は、非置換のアミノ基（－ＮＨ2）を有さないことが好ましい。Ｒ2が非置換のアミノ基（－ＮＨ2）を有するアセタール化合物は、合成時に副反応が起こり易く、合成し難いからである。
Further, R 2 preferably does not have an unsubstituted amino group (—NH 2 ). This is because an acetal compound in which R 2 has an unsubstituted amino group (—NH 2 ) is prone to side reactions during synthesis and is difficult to synthesize.
上述した中でも、本発明の抗菌剤に含まれるアセタール化合物としては、下記のアセタール化合物（１）～（６）が好ましい。これらのアセタール化合物は、ヘキサナール、２－ヘキセナールまたは３－ヘキセナールの徐放性に優れていると共に、臭気が少なく、更に、加水分解後に残留する成分（Ｒ2（ＯＨ）2）が高い水溶性および低い環境負荷の成分となるからである。また、アセタール化合物自体が水酸基を有していることでアセタール化合物の水溶性を確保できると共に、中性の水溶液中において加水分解せずに安定的に存在し得るからである。
Among the above-mentioned compounds, the following acetal compounds (1) to (6) are preferable as the acetal compound contained in the antibacterial agent of the present invention. These acetal compounds are excellent in sustained release of hexanal, 2-hexenal or 3-hexenal, have low odor, and have high water solubility and a high component (R 2 (OH) 2 ) remaining after hydrolysis. It is because it becomes a component of low environmental impact. In addition, since the acetal compound itself has a hydroxyl group, the water-solubility of the acetal compound can be secured, and the acetal compound can exist stably without being hydrolyzed in a neutral aqueous solution.
［アセタール化合物の物性］
そして、上述したアセタール化合物は、水に対する溶解度が、２５℃において０．１ｍｇ／１００ｇ－Ｈ2Ｏ以上であることが好ましく、１ｍｇ／１００ｇ－Ｈ2Ｏ以上であることがより好ましく、１ｇ／１００ｇ－Ｈ2Ｏ以上であることが更に好ましい。アセタール化合物の水に対する溶解度が上記下限値以上であれば、溶媒として水を用いた、安全性およびハンドリング性に優れる液状の抗菌剤として使用することができるからである。 [Physical properties of acetal compounds]
The acetal compound described above has a solubility in water of preferably 0.1 mg / 100 g-H 2 O or more at 25 ° C., more preferably 1 mg / 100 g-H 2 O or more, and 1 g / 100 g. More preferably, it is at least -H 2 O. This is because if the solubility of the acetal compound in water is equal to or higher than the above lower limit value, it can be used as a liquid antibacterial agent using water as a solvent and excellent in safety and handling properties.
そして、上述したアセタール化合物は、水に対する溶解度が、２５℃において０．１ｍｇ／１００ｇ－Ｈ2Ｏ以上であることが好ましく、１ｍｇ／１００ｇ－Ｈ2Ｏ以上であることがより好ましく、１ｇ／１００ｇ－Ｈ2Ｏ以上であることが更に好ましい。アセタール化合物の水に対する溶解度が上記下限値以上であれば、溶媒として水を用いた、安全性およびハンドリング性に優れる液状の抗菌剤として使用することができるからである。 [Physical properties of acetal compounds]
The acetal compound described above has a solubility in water of preferably 0.1 mg / 100 g-H 2 O or more at 25 ° C., more preferably 1 mg / 100 g-H 2 O or more, and 1 g / 100 g. More preferably, it is at least -H 2 O. This is because if the solubility of the acetal compound in water is equal to or higher than the above lower limit value, it can be used as a liquid antibacterial agent using water as a solvent and excellent in safety and handling properties.
また、上述したアセタール化合物を含む本発明の抗菌剤は、大腸菌、黄色ブドウ球菌、ＭＲＳＡおよびサルモネラ菌からなる群より選択される２つ以上の菌に対するＭＩＣ（最小発育阻止濃度）が８００μｇ／ｍＬ以下であることが好ましく、７００μｇ／ｍＬ以下であることがより好ましい。
In addition, the antibacterial agent of the present invention containing the acetal compound described above has a MIC (minimum growth inhibitory concentration) of 800 μg / mL or less for two or more bacteria selected from the group consisting of Escherichia coli, Staphylococcus aureus, MRSA and Salmonella. It is preferable that it is 700 μg / mL or less.
更に、上述したアセタール化合物を含む本発明の抗菌剤は、ノンエンベロームウィルスに対して、エタノール以上の不活性化能力を有することが好ましい。
Furthermore, the antibacterial agent of the present invention containing the acetal compound described above preferably has an inactivation ability higher than that of ethanol against non-enveloped viruses.
そして、上述したアセタール化合物は、温度２５℃、湿度６０％ＲＨの条件下におけるモル半減期が、１０時間以上２０００時間以下であることが好ましい。
The acetal compound described above preferably has a molar half-life of 10 hours or more and 2000 hours or less under conditions of a temperature of 25 ° C. and a humidity of 60% RH.
［アセタール化合物の含有量］
なお、本発明の抗菌剤中に含まれている上記アセタール化合物の量は、０．１質量％以上であることが好ましく、０．５質量％以上であることがより好ましく、１質量％以上であることが更に好ましく、９０質量％以下であることが好ましく、５０質量％以下であることがより好ましい。抗菌剤中のアセタール化合物の含有量が上記下限値以上であれば、十分に長い時間に亘って抗菌効果を発揮させることができるからである。また、抗菌剤中のアセタール化合物の含有量が上記上限値以下であれば、加水分解により放出されるヘキサナール、２－ヘキセナールまたは３－ヘキセナールの量を適度な量とし、臭気の発生を十分に抑制することができるからである。 [Content of acetal compound]
The amount of the acetal compound contained in the antibacterial agent of the present invention is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, and 1% by mass or more. More preferably, it is preferably 90% by mass or less, and more preferably 50% by mass or less. This is because if the content of the acetal compound in the antibacterial agent is not less than the above lower limit value, the antibacterial effect can be exhibited over a sufficiently long time. In addition, if the content of the acetal compound in the antibacterial agent is not more than the above upper limit, the amount of hexanal, 2-hexenal or 3-hexenal released by hydrolysis is set to an appropriate amount, and the generation of odor is sufficiently suppressed. Because it can be done.
なお、本発明の抗菌剤中に含まれている上記アセタール化合物の量は、０．１質量％以上であることが好ましく、０．５質量％以上であることがより好ましく、１質量％以上であることが更に好ましく、９０質量％以下であることが好ましく、５０質量％以下であることがより好ましい。抗菌剤中のアセタール化合物の含有量が上記下限値以上であれば、十分に長い時間に亘って抗菌効果を発揮させることができるからである。また、抗菌剤中のアセタール化合物の含有量が上記上限値以下であれば、加水分解により放出されるヘキサナール、２－ヘキセナールまたは３－ヘキセナールの量を適度な量とし、臭気の発生を十分に抑制することができるからである。 [Content of acetal compound]
The amount of the acetal compound contained in the antibacterial agent of the present invention is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, and 1% by mass or more. More preferably, it is preferably 90% by mass or less, and more preferably 50% by mass or less. This is because if the content of the acetal compound in the antibacterial agent is not less than the above lower limit value, the antibacterial effect can be exhibited over a sufficiently long time. In addition, if the content of the acetal compound in the antibacterial agent is not more than the above upper limit, the amount of hexanal, 2-hexenal or 3-hexenal released by hydrolysis is set to an appropriate amount, and the generation of odor is sufficiently suppressed. Because it can be done.
［アセタール化合物の製造方法］
そして、上述したアセタール化合物は、特に限定されることなく、例えば、上述した一般式：Ｒ1ＣＨＯで表されるアルデヒド（ヘキサナール、ｃｉｓ－２－ヘキセナール、ｔｒａｎｓ－２－ヘキセナール、ｃｉｓ－３－ヘキセナールまたはｔｒａｎｓ－３－ヘキセナール）またはその誘導体に、酸触媒の存在下で、上述した一般式：Ｒ2（ＯＨ）2で表される化合物を縮合させることにより、調製することができる。 [Method for producing acetal compound]
The acetal compound described above is not particularly limited. For example, the aldehyde (hexanal, cis-2-hexenal, trans-2-hexenal, cis-3-hexenal represented by the general formula: R 1 CHO described above is used. Or trans-3-hexenal) or a derivative thereof in the presence of an acid catalyst by condensing the compound represented by the above general formula: R 2 (OH) 2 .
そして、上述したアセタール化合物は、特に限定されることなく、例えば、上述した一般式：Ｒ1ＣＨＯで表されるアルデヒド（ヘキサナール、ｃｉｓ－２－ヘキセナール、ｔｒａｎｓ－２－ヘキセナール、ｃｉｓ－３－ヘキセナールまたはｔｒａｎｓ－３－ヘキセナール）またはその誘導体に、酸触媒の存在下で、上述した一般式：Ｒ2（ＯＨ）2で表される化合物を縮合させることにより、調製することができる。 [Method for producing acetal compound]
The acetal compound described above is not particularly limited. For example, the aldehyde (hexanal, cis-2-hexenal, trans-2-hexenal, cis-3-hexenal represented by the general formula: R 1 CHO described above is used. Or trans-3-hexenal) or a derivative thereof in the presence of an acid catalyst by condensing the compound represented by the above general formula: R 2 (OH) 2 .
ここで、上述したアルデヒドの誘導体としては、例えば、酸化され易く、不安定なアルデヒドである２－ヘキセナールや３－ヘキセナールと、１価のアルコールとを縮合させてなる２－ヘキセナールジアルキルアセタールおよび３－ヘキセナールジアルキルアセタールなどが挙げられる。
また、上述した酸触媒としては、特に限定されることなく、例えば１０－カンファースルホン酸などが挙げられる。
更に、上述した縮合反応は、例えばＮ，Ｎ－ジメチルホルムアミドなどの溶媒中で行うことができる。 Here, examples of the aldehyde derivatives described above include 2-hexenal dialkyl acetals obtained by condensing 2-hexenal or 3-hexenal, which are oxidative and unstable aldehydes, and a monohydric alcohol, and 3- Examples include hexenal dialkyl acetal.
Further, the acid catalyst described above is not particularly limited, and examples thereof include 10-camphorsulfonic acid.
Furthermore, the condensation reaction described above can be performed in a solvent such as N, N-dimethylformamide.
また、上述した酸触媒としては、特に限定されることなく、例えば１０－カンファースルホン酸などが挙げられる。
更に、上述した縮合反応は、例えばＮ，Ｎ－ジメチルホルムアミドなどの溶媒中で行うことができる。 Here, examples of the aldehyde derivatives described above include 2-hexenal dialkyl acetals obtained by condensing 2-hexenal or 3-hexenal, which are oxidative and unstable aldehydes, and a monohydric alcohol, and 3- Examples include hexenal dialkyl acetal.
Further, the acid catalyst described above is not particularly limited, and examples thereof include 10-camphorsulfonic acid.
Furthermore, the condensation reaction described above can be performed in a solvent such as N, N-dimethylformamide.
＜溶媒＞
本発明の抗菌剤が任意に含有し得る溶媒としては、上述したアセタール化合物を溶解または分散可能な任意の溶媒を用いることができる。ここで、溶媒としては、特に限定されることなく、例えば、水や、エタノール等の有機溶媒が挙げられる。中でも、抗菌剤の安全性およびハンドリング性を向上させる観点からは、溶媒としては、水が好ましい。 <Solvent>
As a solvent that can be optionally contained in the antibacterial agent of the present invention, any solvent that can dissolve or disperse the acetal compound described above can be used. Here, the solvent is not particularly limited, and examples thereof include water and organic solvents such as ethanol. Among these, water is preferable as the solvent from the viewpoint of improving the safety and handling properties of the antibacterial agent.
本発明の抗菌剤が任意に含有し得る溶媒としては、上述したアセタール化合物を溶解または分散可能な任意の溶媒を用いることができる。ここで、溶媒としては、特に限定されることなく、例えば、水や、エタノール等の有機溶媒が挙げられる。中でも、抗菌剤の安全性およびハンドリング性を向上させる観点からは、溶媒としては、水が好ましい。 <Solvent>
As a solvent that can be optionally contained in the antibacterial agent of the present invention, any solvent that can dissolve or disperse the acetal compound described above can be used. Here, the solvent is not particularly limited, and examples thereof include water and organic solvents such as ethanol. Among these, water is preferable as the solvent from the viewpoint of improving the safety and handling properties of the antibacterial agent.
＜担体＞
本発明の抗菌剤が任意に含有し得る担体としては、上述したアセタール化合物を担持可能な任意の担体を用いることができる。具体的には、担体としては、特に限定されることなく、例えば、ゼオライトや活性炭などの多孔性物質、寒天やゼラチンなどのゲル状物質、濾紙等の紙、不織布および織布を用いることができる。
なお、アセタール化合物を担体に担持させる方法としては、含浸または混合分散などの既知の方法を用いることができる。 <Carrier>
As the carrier that can be optionally contained in the antibacterial agent of the present invention, any carrier capable of supporting the acetal compound described above can be used. Specifically, the carrier is not particularly limited, and for example, porous materials such as zeolite and activated carbon, gel materials such as agar and gelatin, paper such as filter paper, nonwoven fabrics and woven fabrics can be used. .
As a method for supporting the acetal compound on the carrier, a known method such as impregnation or mixed dispersion can be used.
本発明の抗菌剤が任意に含有し得る担体としては、上述したアセタール化合物を担持可能な任意の担体を用いることができる。具体的には、担体としては、特に限定されることなく、例えば、ゼオライトや活性炭などの多孔性物質、寒天やゼラチンなどのゲル状物質、濾紙等の紙、不織布および織布を用いることができる。
なお、アセタール化合物を担体に担持させる方法としては、含浸または混合分散などの既知の方法を用いることができる。 <Carrier>
As the carrier that can be optionally contained in the antibacterial agent of the present invention, any carrier capable of supporting the acetal compound described above can be used. Specifically, the carrier is not particularly limited, and for example, porous materials such as zeolite and activated carbon, gel materials such as agar and gelatin, paper such as filter paper, nonwoven fabrics and woven fabrics can be used. .
As a method for supporting the acetal compound on the carrier, a known method such as impregnation or mixed dispersion can be used.
＜添加剤＞
本発明の抗菌剤が任意に含有し得る添加剤としては、特に限定されることなく、例えば、界面活性剤、着色剤、粘度調整剤、酸化防止剤、ｐＨ調整剤等を挙げることができる。 <Additives>
The additive that the antibacterial agent of the present invention can optionally contain is not particularly limited, and examples thereof include a surfactant, a colorant, a viscosity modifier, an antioxidant, and a pH adjuster.
本発明の抗菌剤が任意に含有し得る添加剤としては、特に限定されることなく、例えば、界面活性剤、着色剤、粘度調整剤、酸化防止剤、ｐＨ調整剤等を挙げることができる。 <Additives>
The additive that the antibacterial agent of the present invention can optionally contain is not particularly limited, and examples thereof include a surfactant, a colorant, a viscosity modifier, an antioxidant, and a pH adjuster.
（抗菌方法）
本発明の抗菌方法は、上述した本発明の抗菌剤を用いることを特徴とし、例えば、本発明の抗菌剤に抗菌効果を発揮させて抗菌対象物を抗菌処理する際に用いられる。
なお、本発明の抗菌方法で抗菌処理される抗菌対象物は、通常はヒト以外の物であり、好ましくはヒト以外の動植物または非生物（例えば、製品）であり、より好ましくは非生物（例えば、製品）である。 (Antimicrobial method)
The antibacterial method of the present invention is characterized by using the above-described antibacterial agent of the present invention. For example, the antibacterial method of the present invention is used when an antibacterial object is subjected to an antibacterial treatment by exerting an antibacterial effect.
The antibacterial target to be antibacterial treated by the antibacterial method of the present invention is usually a non-human thing, preferably a non-human animal or plant or a non-living object (for example, a product), more preferably a non-living object (for example, a non-human object). , Product).
本発明の抗菌方法は、上述した本発明の抗菌剤を用いることを特徴とし、例えば、本発明の抗菌剤に抗菌効果を発揮させて抗菌対象物を抗菌処理する際に用いられる。
なお、本発明の抗菌方法で抗菌処理される抗菌対象物は、通常はヒト以外の物であり、好ましくはヒト以外の動植物または非生物（例えば、製品）であり、より好ましくは非生物（例えば、製品）である。 (Antimicrobial method)
The antibacterial method of the present invention is characterized by using the above-described antibacterial agent of the present invention. For example, the antibacterial method of the present invention is used when an antibacterial object is subjected to an antibacterial treatment by exerting an antibacterial effect.
The antibacterial target to be antibacterial treated by the antibacterial method of the present invention is usually a non-human thing, preferably a non-human animal or plant or a non-living object (for example, a product), more preferably a non-living object (for example, a non-human object). , Product).
そして、本発明の抗菌方法は、上述した一般式（Ｉ）で表されるアセタール化合物を加水分解する工程（加水分解工程）を含み、抗菌剤中に含まれているアセタール化合物を加水分解し、抗菌成分として上記Ｒ1ＣＨＯ（ヘキサナール、２－ヘキセナールまたは３－ヘキセナール）を生成させることにより、抗菌効果を得る。
And the antibacterial method of this invention includes the process (hydrolysis process) which hydrolyzes the acetal compound represented by the general formula (I) mentioned above, hydrolyzes the acetal compound contained in the antibacterial agent, An antibacterial effect is obtained by producing R 1 CHO (hexanal, 2-hexenal or 3-hexenal) as an antibacterial component.
なお、ヘキサナール、２－ヘキセナールおよび３－ヘキセナールは、揮発性を有する化合物であるため、本発明の抗菌方法では、例えば、抗菌対象物に本発明の抗菌剤を直接接触させた後、或いは、抗菌対象物の周囲に本発明の抗菌剤を配置した後に加水分解工程を実施することで、抗菌対象物を抗菌することができる。
Since hexanal, 2-hexenal and 3-hexenal are volatile compounds, in the antibacterial method of the present invention, for example, after the antibacterial agent of the present invention is brought into direct contact with the antibacterial object, By carrying out the hydrolysis step after disposing the antibacterial agent of the present invention around the object, the antibacterial object can be antibacterial.
ここで、抗菌対象物に本発明の抗菌剤を直接接触させる方法としては、特に限定されることなく、例えば、アセタール化合物を溶媒に溶解または分散させてなる液状の抗菌剤を抗菌対象物に塗布または散布し、任意に塗布または散布した抗菌剤を乾燥させる方法、および、アセタール化合物を担体に担持してなる固体状の抗菌剤を抗菌対象物に接触させる方法などが挙げられる。
また、抗菌対象物の周囲に本発明の抗菌剤を配置する方法としては、特に限定されることなく、例えば、アセタール化合物を溶媒に溶解または分散させてなる液状の抗菌剤を抗菌対象物の周囲に塗布または散布し、任意に塗布または散布した抗菌剤を乾燥させる方法、および、アセタール化合物を担体に担持してなる固体状の抗菌剤を抗菌対象物の周囲に配置する方法などが挙げられる。 Here, the method of bringing the antibacterial agent of the present invention into direct contact with the antibacterial object is not particularly limited. For example, a liquid antibacterial agent obtained by dissolving or dispersing an acetal compound in a solvent is applied to the antibacterial object. Alternatively, a method of spraying and drying the antibacterial agent optionally applied or sprayed and a method of bringing a solid antibacterial agent having an acetal compound supported on a carrier into contact with an antibacterial object are included.
Further, the method for disposing the antibacterial agent of the present invention around the antibacterial object is not particularly limited. For example, a liquid antibacterial agent obtained by dissolving or dispersing an acetal compound in a solvent is used around the antibacterial object. And a method of drying an antibacterial agent that is optionally applied or spread, and a method of disposing a solid antibacterial agent having an acetal compound supported on a carrier around an antibacterial object.
また、抗菌対象物の周囲に本発明の抗菌剤を配置する方法としては、特に限定されることなく、例えば、アセタール化合物を溶媒に溶解または分散させてなる液状の抗菌剤を抗菌対象物の周囲に塗布または散布し、任意に塗布または散布した抗菌剤を乾燥させる方法、および、アセタール化合物を担体に担持してなる固体状の抗菌剤を抗菌対象物の周囲に配置する方法などが挙げられる。 Here, the method of bringing the antibacterial agent of the present invention into direct contact with the antibacterial object is not particularly limited. For example, a liquid antibacterial agent obtained by dissolving or dispersing an acetal compound in a solvent is applied to the antibacterial object. Alternatively, a method of spraying and drying the antibacterial agent optionally applied or sprayed and a method of bringing a solid antibacterial agent having an acetal compound supported on a carrier into contact with an antibacterial object are included.
Further, the method for disposing the antibacterial agent of the present invention around the antibacterial object is not particularly limited. For example, a liquid antibacterial agent obtained by dissolving or dispersing an acetal compound in a solvent is used around the antibacterial object. And a method of drying an antibacterial agent that is optionally applied or spread, and a method of disposing a solid antibacterial agent having an acetal compound supported on a carrier around an antibacterial object.
また、アセタール化合物を加水分解する方法としては、特に限定されることなく、既知の加水分解方法を用いることができる。具体的には、アセタール化合物の加水分解は、例えば、抗菌剤中に含まれている水分または周囲環境中に存在する水分により自然に進行させてもよいし、抗菌剤に対して水を含む溶液を添加することにより進行させてもよい。また、アセタール化合物は、加水分解菌の存在下で加水分解させてもよい。
なお、アセタール化合物の加水分解は、必要に応じ、抗菌剤に対する酸の添加または抗菌剤のｐＨの調整により促進することができる。 Moreover, it does not specifically limit as a method to hydrolyze an acetal compound, A known hydrolysis method can be used. Specifically, the hydrolysis of the acetal compound may naturally proceed, for example, with water contained in the antibacterial agent or water present in the surrounding environment, or a solution containing water with respect to the antibacterial agent. You may make it progress by adding. Further, the acetal compound may be hydrolyzed in the presence of a hydrolyzing bacterium.
In addition, hydrolysis of an acetal compound can be accelerated | stimulated by the addition of the acid with respect to an antibacterial agent, or adjustment of the pH of an antibacterial agent as needed.
なお、アセタール化合物の加水分解は、必要に応じ、抗菌剤に対する酸の添加または抗菌剤のｐＨの調整により促進することができる。 Moreover, it does not specifically limit as a method to hydrolyze an acetal compound, A known hydrolysis method can be used. Specifically, the hydrolysis of the acetal compound may naturally proceed, for example, with water contained in the antibacterial agent or water present in the surrounding environment, or a solution containing water with respect to the antibacterial agent. You may make it progress by adding. Further, the acetal compound may be hydrolyzed in the presence of a hydrolyzing bacterium.
In addition, hydrolysis of an acetal compound can be accelerated | stimulated by the addition of the acid with respect to an antibacterial agent, or adjustment of the pH of an antibacterial agent as needed.
以下、本発明について実施例に基づき具体的に説明するが、本発明はこれら実施例に限定されるものではない。
Hereinafter, the present invention will be specifically described based on examples, but the present invention is not limited to these examples.
（化合物１の合成）
２つ口反応器に一般式：Ｒ2（ＯＨ）2で表される化合物としてのアルブチン１．０ｇ（３．６７ｍｍｏｌ）を加え、溶媒としてのＮ，Ｎ－ジメチルホルムアミド（ＤＭＦ）４０ｍＬに溶解させた。次いで、得られた溶液に対し、一般式：Ｒ1ＣＨＯで表されるアルデヒドとしてのヘキサナール３．６７ｇ（３６．７ｍｍｏｌ）および酸触媒としての１０－カンファースルホン酸０．１７１ｇ（０．７３４ｍｍｏｌ）を加え、５０℃にて２時間反応させた。
そして、反応終了後、飽和重曹水８０ｍＬを加え、酢酸エチル１００ｍＬで有機層を抽出した。また、抽出した有機層を無水硫酸ナトリウムで乾燥させた後、ロータリーエバポレーターで濃縮し、シリカゲルカラムクロマトグラフィー（酢酸エチル： ヘキサン＝１：１（体積比））により精製することで、０．７８２ｇの白色固体を得た（収率：６２．９ｍｏｌ％）。
なお、白色固体を核磁気共鳴（ＮＭＲ）法で分析したところ、以下のアセタール化合物（化合物１）であることが確認された。
(Synthesis of Compound 1)
Arbutin 1.0 g (3.67 mmol) as a compound represented by the general formula: R 2 (OH) 2 was added to a two-necked reactor, and dissolved in 40 mL of N, N-dimethylformamide (DMF) as a solvent. It was. Next, 3.67 g (36.7 mmol) of hexanal as an aldehyde represented by the general formula: R 1 CHO and 0.171 g (0.734 mmol) of 10-camphorsulfonic acid as an acid catalyst were added to the obtained solution. In addition, the mixture was reacted at 50 ° C. for 2 hours.
And after completion | finish of reaction, 80 mL of saturated sodium hydrogen carbonate solution was added, and the organic layer was extracted with 100 mL of ethyl acetate. The extracted organic layer was dried over anhydrous sodium sulfate, concentrated with a rotary evaporator, and purified by silica gel column chromatography (ethyl acetate: hexane = 1: 1 (volume ratio)). A white solid was obtained (yield: 62.9 mol%).
In addition, when white solid was analyzed by the nuclear magnetic resonance (NMR) method, it was confirmed that it was the following acetal compound (compound 1).
２つ口反応器に一般式：Ｒ2（ＯＨ）2で表される化合物としてのアルブチン１．０ｇ（３．６７ｍｍｏｌ）を加え、溶媒としてのＮ，Ｎ－ジメチルホルムアミド（ＤＭＦ）４０ｍＬに溶解させた。次いで、得られた溶液に対し、一般式：Ｒ1ＣＨＯで表されるアルデヒドとしてのヘキサナール３．６７ｇ（３６．７ｍｍｏｌ）および酸触媒としての１０－カンファースルホン酸０．１７１ｇ（０．７３４ｍｍｏｌ）を加え、５０℃にて２時間反応させた。
そして、反応終了後、飽和重曹水８０ｍＬを加え、酢酸エチル１００ｍＬで有機層を抽出した。また、抽出した有機層を無水硫酸ナトリウムで乾燥させた後、ロータリーエバポレーターで濃縮し、シリカゲルカラムクロマトグラフィー（酢酸エチル： ヘキサン＝１：１（体積比））により精製することで、０．７８２ｇの白色固体を得た（収率：６２．９ｍｏｌ％）。
なお、白色固体を核磁気共鳴（ＮＭＲ）法で分析したところ、以下のアセタール化合物（化合物１）であることが確認された。
Arbutin 1.0 g (3.67 mmol) as a compound represented by the general formula: R 2 (OH) 2 was added to a two-necked reactor, and dissolved in 40 mL of N, N-dimethylformamide (DMF) as a solvent. It was. Next, 3.67 g (36.7 mmol) of hexanal as an aldehyde represented by the general formula: R 1 CHO and 0.171 g (0.734 mmol) of 10-camphorsulfonic acid as an acid catalyst were added to the obtained solution. In addition, the mixture was reacted at 50 ° C. for 2 hours.
And after completion | finish of reaction, 80 mL of saturated sodium hydrogen carbonate solution was added, and the organic layer was extracted with 100 mL of ethyl acetate. The extracted organic layer was dried over anhydrous sodium sulfate, concentrated with a rotary evaporator, and purified by silica gel column chromatography (ethyl acetate: hexane = 1: 1 (volume ratio)). A white solid was obtained (yield: 62.9 mol%).
In addition, when white solid was analyzed by the nuclear magnetic resonance (NMR) method, it was confirmed that it was the following acetal compound (compound 1).
（化合物２の合成）
２つ口反応器に一般式：Ｒ2（ＯＨ）2で表される化合物としてのアルブチン１．０ｇ（３．６７ｍｍｏｌ）を加え、溶媒としてのＮ，Ｎ－ジメチルホルムアミド（ＤＭＦ）１０ｍＬに溶解させた。次いで、得られた溶液に対し、一般式：Ｒ1ＣＨＯで表されるアルデヒドであるｃｉｓ－３－ヘキセナールの誘導体としてのｃｉｓ－３－ヘキセナールジエチルアセタール１．２６ｇ（７．３１ｍｍｏｌ）および酸触媒としての１０－カンファースルホン酸０．１７１ｇ（０．７３４ｍｍｏｌ）を加え、５０℃にて１時間反応させた。
そして、反応終了後、飽和重曹水８０ｍＬを加え、酢酸エチル１００ｍＬで有機層を抽出した。また、抽出した有機層を無水硫酸ナトリウムで乾燥させた後、ロータリーエバポレーターで濃縮し、シリカゲルカラムクロマトグラフィー（酢酸エチル： ヘキサン＝１：１（体積比））により精製することで、０．１８５ｇの白色固体を得た（収率：１３．６ｍｏｌ％）。
なお、白色固体を核磁気共鳴（ＮＭＲ）法で分析したところ、以下のアセタール化合物（化合物２）であることが確認された。
(Synthesis of Compound 2)
Arbutin 1.0 g (3.67 mmol) as a compound represented by the general formula: R 2 (OH) 2 was added to a two-necked reactor, and dissolved in 10 mL of N, N-dimethylformamide (DMF) as a solvent. It was. Next, 1.26 g (7.31 mmol) of cis-3-hexenal diethyl acetal as a derivative of cis-3-hexenal, which is an aldehyde represented by the general formula: R 1 CHO, and an acid catalyst are added to the obtained solution. 10-camphorsulfonic acid (0.171 g, 0.734 mmol) was added and reacted at 50 ° C. for 1 hour.
And after completion | finish of reaction, 80 mL of saturated sodium hydrogen carbonate solution was added, and the organic layer was extracted with 100 mL of ethyl acetate. The extracted organic layer was dried over anhydrous sodium sulfate, concentrated with a rotary evaporator, and purified by silica gel column chromatography (ethyl acetate: hexane = 1: 1 (volume ratio)). A white solid was obtained (yield: 13.6 mol%).
In addition, when white solid was analyzed by the nuclear magnetic resonance (NMR) method, it was confirmed that it was the following acetal compound (compound 2).
２つ口反応器に一般式：Ｒ2（ＯＨ）2で表される化合物としてのアルブチン１．０ｇ（３．６７ｍｍｏｌ）を加え、溶媒としてのＮ，Ｎ－ジメチルホルムアミド（ＤＭＦ）１０ｍＬに溶解させた。次いで、得られた溶液に対し、一般式：Ｒ1ＣＨＯで表されるアルデヒドであるｃｉｓ－３－ヘキセナールの誘導体としてのｃｉｓ－３－ヘキセナールジエチルアセタール１．２６ｇ（７．３１ｍｍｏｌ）および酸触媒としての１０－カンファースルホン酸０．１７１ｇ（０．７３４ｍｍｏｌ）を加え、５０℃にて１時間反応させた。
そして、反応終了後、飽和重曹水８０ｍＬを加え、酢酸エチル１００ｍＬで有機層を抽出した。また、抽出した有機層を無水硫酸ナトリウムで乾燥させた後、ロータリーエバポレーターで濃縮し、シリカゲルカラムクロマトグラフィー（酢酸エチル： ヘキサン＝１：１（体積比））により精製することで、０．１８５ｇの白色固体を得た（収率：１３．６ｍｏｌ％）。
なお、白色固体を核磁気共鳴（ＮＭＲ）法で分析したところ、以下のアセタール化合物（化合物２）であることが確認された。
Arbutin 1.0 g (3.67 mmol) as a compound represented by the general formula: R 2 (OH) 2 was added to a two-necked reactor, and dissolved in 10 mL of N, N-dimethylformamide (DMF) as a solvent. It was. Next, 1.26 g (7.31 mmol) of cis-3-hexenal diethyl acetal as a derivative of cis-3-hexenal, which is an aldehyde represented by the general formula: R 1 CHO, and an acid catalyst are added to the obtained solution. 10-camphorsulfonic acid (0.171 g, 0.734 mmol) was added and reacted at 50 ° C. for 1 hour.
And after completion | finish of reaction, 80 mL of saturated sodium hydrogen carbonate solution was added, and the organic layer was extracted with 100 mL of ethyl acetate. The extracted organic layer was dried over anhydrous sodium sulfate, concentrated with a rotary evaporator, and purified by silica gel column chromatography (ethyl acetate: hexane = 1: 1 (volume ratio)). A white solid was obtained (yield: 13.6 mol%).
In addition, when white solid was analyzed by the nuclear magnetic resonance (NMR) method, it was confirmed that it was the following acetal compound (compound 2).
（実施例１）
サンプル瓶に化合物１を０．０５ｇ量りとり、エタノールを４．９５ｇ加えて溶解させた。直径４０ｍｍのろ紙（０．１４ｇ）を準備し、得られた溶液（濃度：１質量％）にろ紙を含浸させた後に乾燥する操作を繰り返し、ろ紙に化合物１を０．０５ｇ担持させた。次に、化合物１を担持させたろ紙を、直径９０ｍｍのシャーレに調製したポテトデキストロース寒天培地に密着させ、その後、クロコウジカビ、アオカビ、ケトミウム、ミロテシウムの混合胞子懸濁液を吹き付けた。そして、温度２６±２℃で２週間培養し、菌糸の発育の様子を観察したところ、菌糸の発育は認められなかった。
なお、培養の前後で臭気の強さを確認したところ、培養前は臭気が認められず、培養後はアルデヒド単体と比較して程よい芳香性を発する程度であった。
抗菌性および臭気の確認結果を表１に纏めて示す。 Example 1
0.05 g of Compound 1 was weighed into a sample bottle, and 4.95 g of ethanol was added and dissolved. A filter paper (0.14 g) having a diameter of 40 mm was prepared, and the obtained solution (concentration: 1% by mass) was impregnated with the filter paper and then dried, and 0.05 g of Compound 1 was supported on the filter paper. Next, the filter paper carrying Compound 1 was brought into close contact with a potato dextrose agar medium prepared in a petri dish having a diameter of 90 mm, and then a mixed spore suspension of Aspergillus niger, Blue mold, Ketomium, and Milotesium was sprayed. And when it culture | cultivated for 2 weeks at the temperature of 26 +/- 2 degreeC and observed the mode of the growth of a mycelia, the growth of the mycelium was not recognized.
In addition, when the strength of the odor was confirmed before and after the culture, the odor was not observed before the culture, and after the culture, the odor was moderately aromatic as compared with the aldehyde alone.
The antibacterial and odor confirmation results are summarized in Table 1.
サンプル瓶に化合物１を０．０５ｇ量りとり、エタノールを４．９５ｇ加えて溶解させた。直径４０ｍｍのろ紙（０．１４ｇ）を準備し、得られた溶液（濃度：１質量％）にろ紙を含浸させた後に乾燥する操作を繰り返し、ろ紙に化合物１を０．０５ｇ担持させた。次に、化合物１を担持させたろ紙を、直径９０ｍｍのシャーレに調製したポテトデキストロース寒天培地に密着させ、その後、クロコウジカビ、アオカビ、ケトミウム、ミロテシウムの混合胞子懸濁液を吹き付けた。そして、温度２６±２℃で２週間培養し、菌糸の発育の様子を観察したところ、菌糸の発育は認められなかった。
なお、培養の前後で臭気の強さを確認したところ、培養前は臭気が認められず、培養後はアルデヒド単体と比較して程よい芳香性を発する程度であった。
抗菌性および臭気の確認結果を表１に纏めて示す。 Example 1
0.05 g of Compound 1 was weighed into a sample bottle, and 4.95 g of ethanol was added and dissolved. A filter paper (0.14 g) having a diameter of 40 mm was prepared, and the obtained solution (concentration: 1% by mass) was impregnated with the filter paper and then dried, and 0.05 g of Compound 1 was supported on the filter paper. Next, the filter paper carrying Compound 1 was brought into close contact with a potato dextrose agar medium prepared in a petri dish having a diameter of 90 mm, and then a mixed spore suspension of Aspergillus niger, Blue mold, Ketomium, and Milotesium was sprayed. And when it culture | cultivated for 2 weeks at the temperature of 26 +/- 2 degreeC and observed the mode of the growth of a mycelia, the growth of the mycelium was not recognized.
In addition, when the strength of the odor was confirmed before and after the culture, the odor was not observed before the culture, and after the culture, the odor was moderately aromatic as compared with the aldehyde alone.
The antibacterial and odor confirmation results are summarized in Table 1.
（実施例２）
化合物１に替えて化合物２を用いた以外は実施例１と同様にして化合物２を担持させたろ紙を調製し、菌糸の発育の様子を観察したところ、菌糸の発育は認められなかった。
なお、培養の前後で臭気の強さを確認したところ、培養前は臭気が認められず、培養後はアルデヒド単体と比較して程よい芳香性を発する程度であった。
抗菌性および臭気の確認結果を表１に纏めて示す。 (Example 2)
A filter paper carrying compound 2 was prepared in the same manner as in Example 1 except that compound 2 was used in place of compound 1, and the growth of mycelia was observed. As a result, no mycelium growth was observed.
In addition, when the strength of the odor was confirmed before and after the culture, the odor was not observed before the culture, and after the culture, the odor was moderately aromatic as compared with the aldehyde alone.
The antibacterial and odor confirmation results are summarized in Table 1.
化合物１に替えて化合物２を用いた以外は実施例１と同様にして化合物２を担持させたろ紙を調製し、菌糸の発育の様子を観察したところ、菌糸の発育は認められなかった。
なお、培養の前後で臭気の強さを確認したところ、培養前は臭気が認められず、培養後はアルデヒド単体と比較して程よい芳香性を発する程度であった。
抗菌性および臭気の確認結果を表１に纏めて示す。 (Example 2)
A filter paper carrying compound 2 was prepared in the same manner as in Example 1 except that compound 2 was used in place of compound 1, and the growth of mycelia was observed. As a result, no mycelium growth was observed.
In addition, when the strength of the odor was confirmed before and after the culture, the odor was not observed before the culture, and after the culture, the odor was moderately aromatic as compared with the aldehyde alone.
The antibacterial and odor confirmation results are summarized in Table 1.
（比較例１）
化合物１を使用せず、エタノールにろ紙を含浸させた後に乾燥する操作を繰り返して得たろ紙を使用した以外は実施例１と同様にして菌糸の発育の様子を観察したところ、ろ紙面積の１／３を超える範囲で菌糸の発育が観察された。
なお、培養の前後で臭気の強さを確認したところ、培養前および培養後の双方で臭気が認められなかった。
抗菌性および臭気の確認結果を表１に纏めて示す。 (Comparative Example 1)
The growth of mycelia was observed in the same manner as in Example 1 except that the filter paper obtained by repeating the drying operation after impregnating ethanol with filter paper without using Compound 1 was used. Mycelium growth was observed in a range exceeding / 3.
In addition, when the strength of the odor was confirmed before and after the culture, no odor was observed both before and after the culture.
The antibacterial and odor confirmation results are summarized in Table 1.
化合物１を使用せず、エタノールにろ紙を含浸させた後に乾燥する操作を繰り返して得たろ紙を使用した以外は実施例１と同様にして菌糸の発育の様子を観察したところ、ろ紙面積の１／３を超える範囲で菌糸の発育が観察された。
なお、培養の前後で臭気の強さを確認したところ、培養前および培養後の双方で臭気が認められなかった。
抗菌性および臭気の確認結果を表１に纏めて示す。 (Comparative Example 1)
The growth of mycelia was observed in the same manner as in Example 1 except that the filter paper obtained by repeating the drying operation after impregnating ethanol with filter paper without using Compound 1 was used. Mycelium growth was observed in a range exceeding / 3.
In addition, when the strength of the odor was confirmed before and after the culture, no odor was observed both before and after the culture.
The antibacterial and odor confirmation results are summarized in Table 1.
実施例１～２および比較例１より、本発明の抗菌剤によれば、臭気を抑制しつつ、抗菌効果を持続的に得ることが可能であることが分かる。
From Examples 1-2 and Comparative Example 1, it can be seen that according to the antibacterial agent of the present invention, the antibacterial effect can be continuously obtained while the odor is suppressed.
本発明によれば、抗菌成分としてヘキサナール、２－ヘキセナールまたは３－ヘキセナールを放出可能であり、更に、臭気が抑制され、且つ、抗菌効果の持続性にも優れた抗菌剤を提供することができる。
また、本発明によれば、臭気を抑制しつつ、ヘキサナール、２－ヘキセナールまたは３－ヘキセナールを徐放させて抗菌効果を持続的に得ることができる。 According to the present invention, it is possible to provide an antibacterial agent capable of releasing hexanal, 2-hexenal, or 3-hexenal as an antibacterial component, further suppressing odor, and having excellent antibacterial effects. .
Furthermore, according to the present invention, the antibacterial effect can be continuously obtained by gradually releasing hexanal, 2-hexenal or 3-hexenal while suppressing odor.
また、本発明によれば、臭気を抑制しつつ、ヘキサナール、２－ヘキセナールまたは３－ヘキセナールを徐放させて抗菌効果を持続的に得ることができる。 According to the present invention, it is possible to provide an antibacterial agent capable of releasing hexanal, 2-hexenal, or 3-hexenal as an antibacterial component, further suppressing odor, and having excellent antibacterial effects. .
Furthermore, according to the present invention, the antibacterial effect can be continuously obtained by gradually releasing hexanal, 2-hexenal or 3-hexenal while suppressing odor.
Claims (7)
- 下記一般式（Ｉ）：
で表されるアセタール化合物を含む、抗菌剤。 The following general formula (I):
The antibacterial agent containing the acetal compound represented by these. - 前記Ｒ2が、グリセリン、ペンチルグリセリルエーテル、２－エチルヘキシルグリセリルエーテル、エチレングリコール、ブタンジオール、ペンタンジオール、ヘキサンジオール、ヘプタンジオール、オクタンジオール、ノナンジオール、デカンジオール、ドデカンジオール、ブタントリオール、ペンタントリオール、ヘキサントリオール、ヘプタントリオール、オクタントリオール、ノナントリオール、デカントリオール、ドデカントリオール、マンニトール、ソルビトール、キシリトール、３－メトキシ－１，２－プロパンジオール、シクロヘキサンジオール、グリセリン酸、イノシトール、トレイトール、アラビニトール、アルブチン、サリシン、グルコース、ガラクトース、マンノース、キシロース、フルクトース、Ｎ－アセチルグルコサミン、グルコノラクトン、マルトース、セロビオース、スクロース、ラクトースおよびラクトビオン酸からなる群より選択される化合物から水酸基を２つ除いた残基である、請求項１に記載の抗菌剤。 R 2 is glycerin, pentyl glyceryl ether, 2-ethylhexyl glyceryl ether, ethylene glycol, butanediol, pentanediol, hexanediol, heptanediol, octanediol, nonanediol, decanediol, dodecanediol, butanetriol, pentanetriol, Hexanetriol, heptanetriol, octanetriol, nonanetriol, decantriol, dodecanetriol, mannitol, sorbitol, xylitol, 3-methoxy-1,2-propanediol, cyclohexanediol, glyceric acid, inositol, threitol, arabinitol, arbutin, Salicin, glucose, galactose, mannose, xylose, fructose, N-acetyl group Kosamin, gluconolactone, maltose, cellobiose, sucrose, two a residue obtained by removing hydroxyl groups from lactose and consisting lactobionic acid compound selected from the group antimicrobial agent according to claim 1.
- 前記Ｒ2が、水酸基を２つ以上含有する天然物から水酸基を２つ除いた残基である、請求項１または２に記載の抗菌剤。 The antibacterial agent according to claim 1 or 2, wherein R 2 is a residue obtained by removing two hydroxyl groups from a natural product containing two or more hydroxyl groups.
- 前記Ｒ2が、水酸基を２つ以上含有する水溶性化合物から水酸基を２つ除いた残基である、請求項１～３の何れかに記載の抗菌剤。 The antibacterial agent according to any one of claims 1 to 3, wherein R 2 is a residue obtained by removing two hydroxyl groups from a water-soluble compound containing two or more hydroxyl groups.
- 前記Ｒ2の炭素数が２以上である、請求項１～４の何れかに記載の抗菌剤。 The antibacterial agent according to any one of claims 1 to 4, wherein R 2 has 2 or more carbon atoms.
- 前記Ｒ2が非置換のアミノ基を有さない、請求項１～５の何れかに記載の抗菌剤。 The antibacterial agent according to any one of claims 1 to 5, wherein R 2 does not have an unsubstituted amino group.
- 前記アセタール化合物を加水分解する工程を含む、請求項１～６の何れかに記載の抗菌剤を用いた抗菌方法。 An antibacterial method using the antibacterial agent according to any one of claims 1 to 6, comprising a step of hydrolyzing the acetal compound.
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| KR102090101B1 (en) * | 2019-06-18 | 2020-03-17 | 주식회사 테코자임 | Oral composition for preventation or treatment of oral disease |
| JP7547785B2 (en) | 2020-05-25 | 2024-09-10 | Ｔｏｐｐａｎホールディングス株式会社 | Antibacterial Films and Packaging Materials |
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| WO2020256348A1 (en) * | 2019-06-18 | 2020-12-24 | 주식회사 테코자임 | Composition for preventing or treating oral diseases |
| JP7547785B2 (en) | 2020-05-25 | 2024-09-10 | Ｔｏｐｐａｎホールディングス株式会社 | Antibacterial Films and Packaging Materials |
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