WO2017188195A1 - Agent antibactérien et procédé de traitement antibactérien - Google Patents

Agent antibactérien et procédé de traitement antibactérien Download PDF

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Publication number
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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WO
WIPO (PCT)
Prior art keywords
antibacterial
antibacterial agent
hexenal
hydroxyl groups
group
Prior art date
Application number
PCT/JP2017/016251
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English (en)
Japanese (ja)
Inventor
孝則 美馬
加奈子 佐貫
菅原　充
智史 桐木
Original Assignee
日本ゼオン株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 日本ゼオン株式会社 filed Critical 日本ゼオン株式会社
Priority to JP2018514590A priority Critical patent/JP6996498B2/ja
Publication of WO2017188195A1 publication Critical patent/WO2017188195A1/fr

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Classifications

    • 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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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention a pour objet de fournir un agent antibactérien qui peut libérer de l'hexanal, du 2-hexénal ou du 3-hexénal à partir de celui-ci en tant que constituant antibactérien, et qui présente une odeur réduite et une action antibactérienne d'excellente durabilité. L'agent antibactérien de l'invention contient un composé acétal représenté par la formule générale (I). Dans ladite formule, R 1 représente un groupe n-pentyle, un groupe 1-pentényle ou un groupe 2-pentényle; et R 2 représente un groupe organique bivalent.
PCT/JP2017/016251 2016-04-28 2017-04-24 Agent antibactérien et procédé de traitement antibactérien WO2017188195A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2018514590A JP6996498B2 (ja) 2016-04-28 2017-04-24 抗菌剤および抗菌方法

Applications Claiming Priority (2)

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JP2016-091706 2016-04-28
JP2016091706 2016-04-28

Publications (1)

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WO2017188195A1 true WO2017188195A1 (fr) 2017-11-02

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102090101B1 (ko) * 2019-06-18 2020-03-17 주식회사 테코자임 구강 질환 예방 또는 치료용 조성물
JP7547785B2 (ja) 2020-05-25 2024-09-10 Ｔｏｐｐａｎホールディングス株式会社 抗菌フィルムおよび包装材

Citations (6)

* Cited by examiner, † Cited by third party
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JP2001302475A (ja) * 2000-04-24 2001-10-31 Lion Corp 口腔用組成物
JP2002128610A (ja) * 2000-10-17 2002-05-09 Kao Corp 抗菌抗カビ剤
JP2008037858A (ja) * 2006-07-12 2008-02-21 Institute Of National Colleges Of Technology Japan 徐放剤
JP2009544632A (ja) * 2006-07-28 2009-12-17 ジボダン エス エー 有機化合物の使用方法
JP2013526604A (ja) * 2010-05-23 2013-06-24 高砂香料工業株式会社 抗菌組成物
JP2014534967A (ja) * 2011-10-20 2014-12-25 アニトックス コーポレーション ペラルゴン酸を含む抗微生物処方剤

Family Cites Families (3)

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DD130907A1 (de) * 1977-04-25 1978-05-17 Horst Lyr Mittel zur schaderregerbekaempfung im pflanzenschutz und vorratsschutz
WO1995011899A1 (fr) * 1993-10-25 1995-05-04 Shell Internationale Research Maatschappij B.V. Derives de pyrimidine
JPH07187977A (ja) * 1993-12-24 1995-07-25 Lion Corp 口腔用組成物

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001302475A (ja) * 2000-04-24 2001-10-31 Lion Corp 口腔用組成物
JP2002128610A (ja) * 2000-10-17 2002-05-09 Kao Corp 抗菌抗カビ剤
JP2008037858A (ja) * 2006-07-12 2008-02-21 Institute Of National Colleges Of Technology Japan 徐放剤
JP2009544632A (ja) * 2006-07-28 2009-12-17 ジボダン エス エー 有機化合物の使用方法
JP2013526604A (ja) * 2010-05-23 2013-06-24 高砂香料工業株式会社 抗菌組成物
JP2014534967A (ja) * 2011-10-20 2014-12-25 アニトックス コーポレーション ペラルゴン酸を含む抗微生物処方剤

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102090101B1 (ko) * 2019-06-18 2020-03-17 주식회사 테코자임 구강 질환 예방 또는 치료용 조성물
WO2020256348A1 (fr) * 2019-06-18 2020-12-24 주식회사 테코자임 Composition visant à prévenir ou à traiter des maladies bucco-dentaires
JP7547785B2 (ja) 2020-05-25 2024-09-10 Ｔｏｐｐａｎホールディングス株式会社 抗菌フィルムおよび包装材

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JP6996498B2 (ja) 2022-01-17
JPWO2017188195A1 (ja) 2019-03-07

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