JPH0733649A - Anticarious agent - Google Patents

Anticarious agent

Info

Publication number
JPH0733649A
JPH0733649A JP20045393A JP20045393A JPH0733649A JP H0733649 A JPH0733649 A JP H0733649A JP 20045393 A JP20045393 A JP 20045393A JP 20045393 A JP20045393 A JP 20045393A JP H0733649 A JPH0733649 A JP H0733649A
Authority
JP
Japan
Prior art keywords
agent
tooth
oral composition
blended
mutans
Prior art date
Legal status (The legal status 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 status listed.)
Pending
Application number
JP20045393A
Other languages
Japanese (ja)
Inventor
Takeshi Ikemoto
毅 池本
Hiroko Nakatsugawa
弘子 中津川
Keiko Takahashi
啓子 高橋
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kanebo Ltd
Original Assignee
Kanebo Ltd
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 Kanebo Ltd filed Critical Kanebo Ltd
Priority to JP20045393A priority Critical patent/JPH0733649A/en
Publication of JPH0733649A publication Critical patent/JPH0733649A/en
Pending legal-status Critical Current

Links

Landscapes

  • Cosmetics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

PURPOSE:To obtain an anticarious agent, having strong antimicrobial actions on Streptococcus mutans and capable of being blended in an oral composition, etc., capable of avoiding or preventing the dental caries. CONSTITUTION:This anticarious agent is composed of a biphenyl compound expressed by the formula (R is H or 1-8C linear or branched chainlike saturated hydrocarbon group). This compound has antimicrobial actions on Streptococcus mutans in a concentration-dependent manner, manifests effects at a low concentration and can be blended in an oral composition such as a tooth paste, a tooth powder, a tooth wash, a mouthwash or a troche and further a chewing gum, a candy, a thick malt syrup, etc.

Description

【発明の詳細な説明】Detailed Description of the Invention

【0001】[0001]

【産業上の利用分野】本発明は、う蝕を誘発する病原菌
であるストレプトコッカス・ミュータンス(Streptococ
cus mutans、以下S.mutansと略記する)に対し強い抗菌
性及び発育阻害を有するビフェニル化合物に関するもの
である。
TECHNICAL FIELD The present invention relates to Streptococcus mutans which is a pathogenic bacterium that induces dental caries.
cus mutans, hereinafter abbreviated as S. mutans) to a biphenyl compound having strong antibacterial properties and growth inhibition.

【0002】[0002]

【従来の技術】[Prior art]

【0003】う蝕の防止及び予防の一つとしてう蝕原因
菌を撲滅もしくは生育を防止する方法が従来より知られ
ている。例えば、ペニシリンやエリスルマイシン等の抗
生物質、う蝕原因菌であるS.mutansの細胞壁を溶解する
細胞壁溶解酵素やシクロヘキシウジン等の殺菌剤の使用
が試みられている。
As one of the prevention and prevention of caries, a method of eradicating caries-causing bacteria or preventing growth thereof has been conventionally known. For example, attempts have been made to use antibiotics such as penicillin and erythromycin, cell wall lytic enzymes that dissolve the cell wall of S. mutans, which is a causative bacterium, and bactericides such as cyclohexidine.

【0004】また、植物抽出物を用いたう蝕予防剤とし
て、ニクズク等の抽出物(特開昭59−134729号
公報)や柿の葉,ケンポナシの果実の抽出物を用いた口
腔用組成物(特開平2−78609号公報)等が提案さ
れている。
Further, as a caries preventive agent using a plant extract, an oral composition using an extract of Japanese nutmeg (Japanese Patent Laid-Open No. 59-134729), an extract of persimmon leaves, and fruits of Japanese quince (Japanese Patent Laid-Open No. 2-78609) and the like have been proposed.

【0005】さらに、特定のカルボン酸やラクトン構造
を有する合成香料を抗う蝕剤として用いる方法(特開昭
59−175423号公報)やマグノロール、ホオノキ
オールをう蝕予防剤として用いる方法(特開平1−15
1512号公報)等が提案されている。
Further, a method of using a synthetic fragrance having a specific carboxylic acid or lactone structure as an anti-caries agent (Japanese Patent Laid-Open No. 175423/1984) or a method of using magnolol or honokiol as a caries preventive agent (Japanese Patent Laid-Open No. Hei 9 (1999) -58,091) 1-15
No. 1512) has been proposed.

【0006】しかしながら、抗生物質には副作用の問
題、合成香料には特異臭の問題、マグノロールやホオノ
キオールには安定性に問題があるなど、何れも改善の必
要性があった。
However, antibiotics have side effects, synthetic fragrances have a peculiar odor problem, and magnolol and honokiol have stability problems.

【0007】[0007]

【発明が解決しようとする課題】本発明者等は、上記事
情を鑑み鋭意検討した結果、特定のビフェニル化合物
が、う蝕原因菌であるS.mutansに対して強い抗菌作用を
有していることを見いだした。
DISCLOSURE OF THE INVENTION As a result of intensive studies made by the present inventors in view of the above circumstances, a specific biphenyl compound has a strong antibacterial action against S. mutans which is a cariogenic bacterium. I found a thing.

【0008】したがって、本発明者の目的は、う蝕原因
菌であるS.mutansに対して強い抗菌作用を有する化合物
を提供することにある。
[0008] Therefore, an object of the present inventor is to provide a compound having a strong antibacterial action against S. mutans which is a cariogenic bacterium.

【0009】[0009]

【課題を解決するための手段】即ち、本発明は下記一般
Means for Solving the Problems That is, the present invention has the following general formula:

【0010】[0010]

【化2】 [Chemical 2]

【0011】(但しRは水素原子もしくは炭素数1から
8の直鎖及び分岐鎖状の飽和炭化水素基)で表されるビ
フェニル化合物からなる抗う蝕剤に関するものである。
(Wherein R is a hydrogen atom or a linear or branched saturated hydrocarbon group having 1 to 8 carbon atoms) and relates to an anticaries agent comprising a biphenyl compound.

【0012】本発明に使用されるビフェニル化合物の一
部は公知の物質が含まれ、その合成方法について報告さ
れている(日本化学雑誌第87巻、第6号、603頁、
1966年)。また、公知以外の化合物も同様の合成方
法によって得ることが出来る。
A part of the biphenyl compound used in the present invention includes known substances, and a method for synthesizing the same has been reported (Japan Chemical Journal Vol. 87, No. 6, p. 603,
1966). Also, compounds other than known compounds can be obtained by the same synthetic method.

【0013】本発明の抗う蝕剤は、例えば練り歯磨き、
粉歯磨き、水歯磨き、マウスウォッシュ、トローチ等の
口腔用組成物やチューインガム、キャンディー、飴等に
配合することが出来る。
The anti-caries agent of the present invention is, for example, a toothpaste,
It can be added to oral compositions such as toothpaste, toothpaste, mouthwash, troche, etc., chewing gum, candy, candy and the like.

【0014】その配合量は使用する系によって異なり、
一概には言えないが、以下の実施例から明らかなよう
に、既存のこの種の物質と同等でよい。
The blending amount depends on the system used,
Although it cannot be generally stated, as is clear from the following examples, it may be equivalent to the existing substances of this type.

【0015】次に、本発明のビフェニル化合物によるS.
mutansに対する抗菌作用の効果を明らかにするための実
施例を示す。
Next, S.
An example for clarifying the effect of antibacterial action against mutans will be shown.

【0016】[0016]

【実施例】 以下実施
例により本発明を更に詳細に説明する。尚、以下におけ
る%表示は、特に指定しない限り、容量%を示す。実施
例におけるビフェニル化合物の名称を前記一般式のRの
違いにより以下の如く略記する。ビフェニル化合物1
(R=CH3 )、ビフェニル化合物2(R=C
2 5 )、ビフェニル化合物3(R=C3 7 )、ビフ
ェニル化合物4(R=iso−C37 )、ビフェニル
化合物5(R=C8 17)、ビフェニル化合物6(R=
H)。また、構造の異なるビフェニル化合物であるデヒ
ドロジオイゲノール、デヒドロジクレオソールを対照と
して用いた。
EXAMPLES The present invention will be described in more detail with reference to the following examples. In addition, unless otherwise specified, the percentage display in the following shows the percentage by volume. The names of the biphenyl compounds in the examples are abbreviated as follows depending on the difference in R in the general formula. Biphenyl compound 1
(R = CH 3 ), biphenyl compound 2 (R = C
2 H 5), biphenyl compounds 3 (R = C 3 H 7 ), biphenyl compounds 4 (R = iso-C 3 H 7), biphenyl compounds 5 (R = C 8 H 17 ), biphenyl compounds 6 (R =
H). In addition, dehydrodioigenol and dehydrodicresol, which are biphenyl compounds having different structures, were used as controls.

【0017】〔抗菌作用試験方法〕ストレプトコッカス
・ミュータンスに対する抗菌作用を試験する方法として
ペーパーディスク法を用いて行った。寒天培地に、別に
同液体培地で培養しておいたS.mutans培養液を混合
(0.1ml/100ml培地)し、10mlをシャー
レに分注固化した。シャーレの中央にペーパーディスク
を置き、試料の無水エタノール溶液50μlを滴下し
た。5℃にて24時間静置した後、32℃にて48時間
培養した。ペーパーディスクのまわりに形成された阻止
円の直径を測定する事により、抗菌力を調べた。測定に
用いたサンプル濃度は1.25、0.625、0.31
3および0.156%で行った。
[Test Method for Antibacterial Action] As a method for testing the antibacterial action against Streptococcus mutans, a paper disk method was used. The agar medium was mixed with the S. mutans culture solution that had been separately cultured in the same liquid medium (0.1 ml / 100 ml medium), and 10 ml was dispensed and solidified in a petri dish. A paper disk was placed in the center of the petri dish, and 50 μl of an absolute ethanol solution of the sample was dropped. After standing at 5 ° C. for 24 hours, it was cultured at 32 ° C. for 48 hours. The antibacterial activity was investigated by measuring the diameter of the inhibition circle formed around the paper disc. The sample concentrations used for measurement are 1.25, 0.625, 0.31.
3 and 0.156%.

【0018】[0018]

【表1】 [Table 1]

【0019】表1の結果から、本発明のビフェニル化合
物は、濃度依存的にS.mutansに対して抗菌作用を有し、
しかも低濃度で効果のあることがわかった。
From the results shown in Table 1, the biphenyl compound of the present invention has an antibacterial action against S. mutans in a concentration-dependent manner,
Moreover, it was found that it was effective at low concentrations.

【0020】[0020]

【発明の効果】以上記載の如く、本発明が低濃度でS.mu
tansに対して強い抗菌作用を有することから、う蝕を防
止もしくは予防するための口腔用組成物やチューインガ
ム、キャンディー、飴等への配合が可能な抗う蝕剤を提
供することは明かである。
INDUSTRIAL APPLICABILITY As described above, according to the present invention, S.mu
Since it has a strong antibacterial action against tans, it is obvious to provide an anti-caries agent which can be incorporated into an oral composition for preventing or preventing dental caries and chewing gum, candy, candy and the like.

Claims (1)

【特許請求の範囲】[Claims] 【請求項1】 下記一般式で表されるビフェニル化合物
からなる抗う蝕剤。 【化1】 (但しRは水素原子もしくは炭素数1から8の直鎖及び
分岐鎖状の飽和炭化水素基)
1. An anticaries agent comprising a biphenyl compound represented by the following general formula. [Chemical 1] (However, R is a hydrogen atom or a linear or branched saturated hydrocarbon group having 1 to 8 carbon atoms)
JP20045393A 1993-07-19 1993-07-19 Anticarious agent Pending JPH0733649A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP20045393A JPH0733649A (en) 1993-07-19 1993-07-19 Anticarious agent

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP20045393A JPH0733649A (en) 1993-07-19 1993-07-19 Anticarious agent

Publications (1)

Publication Number Publication Date
JPH0733649A true JPH0733649A (en) 1995-02-03

Family

ID=16424560

Family Applications (1)

Application Number Title Priority Date Filing Date
JP20045393A Pending JPH0733649A (en) 1993-07-19 1993-07-19 Anticarious agent

Country Status (1)

Country Link
JP (1) JPH0733649A (en)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09165727A (en) * 1995-04-18 1997-06-24 Tadashi Ito Wave-absorbing block with pierced hole, seawater exchanging type breakwater, and seawater genetration type wave-absorbing block embankment
WO2006071654A1 (en) 2004-12-29 2006-07-06 Colgate-Palmolive Company Oral compositions containing biphenol antibacterial compounds
US7211700B2 (en) * 2000-12-20 2007-05-01 Mcneil-Ppc, Inc. Non-halogenated phenyl substituted phenols, antimicrobial compositions containing the same, and methods of using the same
US8313733B2 (en) 2005-03-18 2012-11-20 Colgate-Palmolive Company Antibacterial 5,5′-disubstituted 3,3′ dialkoxy-2,2′-dihydroxy-1,1′-biphenyl
US8425881B2 (en) 2005-03-18 2013-04-23 Colgate-Palmolive Company Antibacterial 3′,5-disubstituted 2,4′-dihydroxybiphenyl compounds, derivatives and related methods
JP2013520518A (en) * 2010-02-24 2013-06-06 コルゲート・パーモリブ・カンパニー Oral care composition
JP2014062097A (en) * 2007-10-01 2014-04-10 Colgate Palmolive Co Anti-bacterial pyrocatechols and related methods
US20140314688A1 (en) * 2011-12-02 2014-10-23 Colgate-Palmolive Company Oral care compositions
US20140328772A1 (en) * 2011-12-15 2014-11-06 Colgate-Palmolive Company Solubilized magnolol analogs
US20140341818A1 (en) * 2011-12-15 2014-11-20 Colgate-Palmolive Company Solubilized magnolol analogs
US20150004104A1 (en) * 2012-03-02 2015-01-01 Colgate-Palmolive Company Oral care compositions
US9439843B2 (en) 2011-12-02 2016-09-13 Colgate-Palmolive Company Oral care compositions
CN110668981A (en) * 2019-09-20 2020-01-10 广东省禾基生物科技有限公司 Magnolol derivative and preparation method and application thereof

Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09165727A (en) * 1995-04-18 1997-06-24 Tadashi Ito Wave-absorbing block with pierced hole, seawater exchanging type breakwater, and seawater genetration type wave-absorbing block embankment
US7211700B2 (en) * 2000-12-20 2007-05-01 Mcneil-Ppc, Inc. Non-halogenated phenyl substituted phenols, antimicrobial compositions containing the same, and methods of using the same
WO2006071654A1 (en) 2004-12-29 2006-07-06 Colgate-Palmolive Company Oral compositions containing biphenol antibacterial compounds
AU2005322192B2 (en) * 2004-12-29 2009-07-23 Colgate-Palmolive Company Oral compositions containing biphenol antibacterial compounds
EP2266666A1 (en) * 2004-12-29 2010-12-29 Colgate-Palmolive Company Oral compositions containing biphenol antibacterial compounds
US8071077B2 (en) 2004-12-29 2011-12-06 Colgate-Palmolive Company Oral compositions containing biphenol antibacterial compounds
CN103720678B (en) * 2004-12-29 2016-08-31 高露洁-棕榄公司 Oral cavity composition containing biphenol antibacterial compounds
US8652444B2 (en) 2004-12-29 2014-02-18 Colgate-Palmolive Company Oral compositions containing biphenol antibacterial compounds
CN103720678A (en) * 2004-12-29 2014-04-16 高露洁-棕榄公司 Oral compositions containing biphenol antibacterial compounds
US8313733B2 (en) 2005-03-18 2012-11-20 Colgate-Palmolive Company Antibacterial 5,5′-disubstituted 3,3′ dialkoxy-2,2′-dihydroxy-1,1′-biphenyl
US8425881B2 (en) 2005-03-18 2013-04-23 Colgate-Palmolive Company Antibacterial 3′,5-disubstituted 2,4′-dihydroxybiphenyl compounds, derivatives and related methods
JP2014062097A (en) * 2007-10-01 2014-04-10 Colgate Palmolive Co Anti-bacterial pyrocatechols and related methods
JP2015212274A (en) * 2010-02-24 2015-11-26 コルゲート・パーモリブ・カンパニーColgate−Palmolive Company Oral care composition
US8956592B2 (en) 2010-02-24 2015-02-17 Colgate-Palmolive Company Oral care compositions
JP2013520518A (en) * 2010-02-24 2013-06-06 コルゲート・パーモリブ・カンパニー Oral care composition
JP2015500233A (en) * 2011-12-02 2015-01-05 コルゲート・パーモリブ・カンパニーColgate−Palmolive Company Oral care composition
US20140314688A1 (en) * 2011-12-02 2014-10-23 Colgate-Palmolive Company Oral care compositions
US9370475B2 (en) * 2011-12-02 2016-06-21 Colgate-Palmolive Company Oral care compositions
US9439843B2 (en) 2011-12-02 2016-09-13 Colgate-Palmolive Company Oral care compositions
US20140328772A1 (en) * 2011-12-15 2014-11-06 Colgate-Palmolive Company Solubilized magnolol analogs
US20140341818A1 (en) * 2011-12-15 2014-11-20 Colgate-Palmolive Company Solubilized magnolol analogs
US9414587B2 (en) * 2011-12-15 2016-08-16 Cologne-Palmolive Company Solubilized magnolol analogs
US20150004104A1 (en) * 2012-03-02 2015-01-01 Colgate-Palmolive Company Oral care compositions
US9795548B2 (en) 2012-03-02 2017-10-24 Colgate-Palmolive Company Oral care compositions
CN110668981A (en) * 2019-09-20 2020-01-10 广东省禾基生物科技有限公司 Magnolol derivative and preparation method and application thereof

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