JPS6330409A - Agent for inhibiting growth of cariogenic bacteria - Google Patents
Agent for inhibiting growth of cariogenic bacteriaInfo
- Publication number
- JPS6330409A JPS6330409A JP61171683A JP17168386A JPS6330409A JP S6330409 A JPS6330409 A JP S6330409A JP 61171683 A JP61171683 A JP 61171683A JP 17168386 A JP17168386 A JP 17168386A JP S6330409 A JPS6330409 A JP S6330409A
- Authority
- JP
- Japan
- Prior art keywords
- formation
- growth
- streptococcus mutans
- glucan
- agent
- 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.)
- Granted
Links
- 241000894006 Bacteria Species 0.000 title claims description 9
- 230000001013 cariogenic effect Effects 0.000 title claims 2
- 230000002401 inhibitory effect Effects 0.000 title abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 claims abstract description 10
- LCYXQUJDODZYIJ-UHFFFAOYSA-N pinocarveol Chemical compound C1C2C(C)(C)C1CC(O)C2=C LCYXQUJDODZYIJ-UHFFFAOYSA-N 0.000 claims abstract description 10
- IFYYFLINQYPWGJ-UHFFFAOYSA-N gamma-decalactone Chemical compound CCCCCCC1CCC(=O)O1 IFYYFLINQYPWGJ-UHFFFAOYSA-N 0.000 claims abstract description 8
- PHXATPHONSXBIL-UHFFFAOYSA-N xi-gamma-Undecalactone Chemical compound CCCCCCCC1CCC(=O)O1 PHXATPHONSXBIL-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 claims abstract description 5
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 claims abstract description 5
- 229930007744 linalool Natural products 0.000 claims abstract description 5
- LCYXQUJDODZYIJ-VGMNWLOBSA-N trans-Pinocarveol Natural products C1[C@@H]2C(C)(C)[C@H]1C[C@H](O)C2=C LCYXQUJDODZYIJ-VGMNWLOBSA-N 0.000 claims abstract description 5
- IFYYFLINQYPWGJ-VIFPVBQESA-N gamma-Decalactone Natural products CCCCCC[C@H]1CCC(=O)O1 IFYYFLINQYPWGJ-VIFPVBQESA-N 0.000 claims abstract description 4
- PHXATPHONSXBIL-JTQLQIEISA-N gamma-Undecalactone Natural products CCCCCCC[C@H]1CCC(=O)O1 PHXATPHONSXBIL-JTQLQIEISA-N 0.000 claims abstract description 4
- 229940020436 gamma-undecalactone Drugs 0.000 claims abstract description 4
- 239000003966 growth inhibitor Substances 0.000 claims description 7
- OGCGGWYLHSJRFY-SECBINFHSA-N (+)-alpha-Campholenal Natural products CC1=CC[C@H](CC=O)C1(C)C OGCGGWYLHSJRFY-SECBINFHSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- OGCGGWYLHSJRFY-UHFFFAOYSA-N alpha-campholenaldehyde Chemical compound CC1=CCC(CC=O)C1(C)C OGCGGWYLHSJRFY-UHFFFAOYSA-N 0.000 claims description 2
- 241000194019 Streptococcus mutans Species 0.000 abstract description 14
- 230000015572 biosynthetic process Effects 0.000 abstract description 13
- 229920001503 Glucan Polymers 0.000 abstract description 11
- 239000003205 fragrance Substances 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 abstract description 3
- DKKRDMLKVSKFMJ-UHFFFAOYSA-N 4-propan-2-ylcyclohexan-1-ol Chemical compound CC(C)C1CCC(O)CC1 DKKRDMLKVSKFMJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 208000002925 dental caries Diseases 0.000 description 9
- 230000000844 anti-bacterial effect Effects 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 6
- 239000002609 medium Substances 0.000 description 5
- 208000002064 Dental Plaque Diseases 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 235000000346 sugar Nutrition 0.000 description 4
- 229920002307 Dextran Polymers 0.000 description 3
- 235000014655 lactic acid Nutrition 0.000 description 3
- 239000004310 lactic acid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 210000000214 mouth Anatomy 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 102000000340 Glucosyltransferases Human genes 0.000 description 1
- 108010055629 Glucosyltransferases Proteins 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 239000004098 Tetracycline Substances 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- LFVVNPBBFUSSHL-UHFFFAOYSA-N alexidine Chemical compound CCCCC(CC)CNC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NCC(CC)CCCC LFVVNPBBFUSSHL-UHFFFAOYSA-N 0.000 description 1
- 229950010221 alexidine Drugs 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 229940112822 chewing gum Drugs 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 229960003260 chlorhexidine Drugs 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 230000003412 degenerative effect Effects 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 229940051866 mouthwash Drugs 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 230000007505 plaque formation Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
Landscapes
- Confectionery (AREA)
- Furan Compounds (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Description
【発明の詳細な説明】
〈産業上の利用分野〉
本発明は虫歯（うｔｋ）の形成に大きく関与しているス
トレプトコッカス・ミュータンス（Ｓｔｒｅｐｔｏ−ｃ
ｏｃｃｕｓ ＋５ｕｔａｎｓ）に代表される口腔内細菌
に対して優れた抗菌活性を示し、且つ口腔内微生物が関
与するグルカン形成を阻止しうる、う真菌生育阻害剤に
関する。Detailed Description of the Invention <Industrial Application Field> The present invention is directed to the use of Streptococcus mutans (Streptococcus mutans), which is greatly involved in the formation of dental caries.
The present invention relates to a caries growth inhibitor that exhibits excellent antibacterial activity against oral bacteria such as S. occus +5utans) and is capable of inhibiting glucan formation involving oral microorganisms.
〈従来の技術〉
従来、口腔内細菌の生育を阻害する薬剤としてはクロル
ヘキシジン、アレキシジン等の殺菌剤及びペニシリン、
テトラサイクリン等の抗生物質等の使用が知られている
他、多くの合成品、天然品が報告されている。<Prior art> Conventionally, as drugs that inhibit the growth of oral bacteria, disinfectants such as chlorhexidine and alexidine, penicillin,
In addition to the known use of antibiotics such as tetracycline, many synthetic and natural products have been reported.
〈発明が解決しようとする問題点〉
しかしながら、これら公知の口腔内細菌の生育阻害剤は
投与方法、投与量によっては人体に対する安全性に問題
があったり、安定性に問題があったり、安定性が確認さ
れているものは抗菌性が低かったり、また投与した際、
不快な臭いがするなどの欠点があった。<Problems to be solved by the invention> However, these known oral bacteria growth inhibitors may have safety problems for the human body depending on the administration method and dosage, or may have stability problems. Those that have been confirmed to have low antibacterial properties, or when administered,
There were drawbacks such as an unpleasant odor.
〈発明の目的〉
本発明の目的は、虫歯菌であるストレプトコッカス・ミ
ュータンス菌の生育阻害に非常に有効で、且つ歯垢の原
因となるデキストラン（グルカン）形成抑制にも有効で
あっても快い芳香を有するう力菌生育阻害剤を提供する
ことにある。<Objective of the Invention> The object of the present invention is to provide a compound that is very effective in inhibiting the growth of Streptococcus mutans, which is a cavity-causing bacterium, and is also effective in inhibiting the formation of dextran (glucan), which causes dental plaque. An object of the present invention is to provide a growth inhibitor of steric fungi that has an aroma.
く問題点を解決するための手段〉
本発明によれば、リナロール、トランス−ピノカルベオ
ール、バラ−イソプロピルシクロヘキサノール、カンホ
レニックアルデヒド、γ−デカラクトン及びγ−ウンデ
カラクトンから成る群から選ばれた少くとも一種を有効
成分として含有する。Means for Solving the Problems> According to the present invention, a compound selected from the group consisting of linalool, trans-pinocarveol, para-isopropylcyclohexanol, camphorenic aldehyde, γ-decalactone and γ-undecalactone. Contains at least one type of active ingredient.
う負菌生育阻害剤が提供される。A caries growth inhibitor is provided.
以下本発明につき更に詳細に説明する。The present invention will be explained in more detail below.
一般的に虫歯（う１）ｋ）形成の原因としては歯質（Ｔ
ａｅｔｈ）と基質（Ｓｕｂｓｔｒａｔｅ）とミュータン
ス菌（Ｓｔ、ｍｕｔａｎｓ）とを挙げることができ、こ
の３つの要因が同時に存在するとき、虫歯（う負）が発
生するとされている。虫歯（う負）形成のメカニズムは
１例えば糖類の中で砂糖を基質（Ｓｕｂｓｔｒａｔａ）
とした場合、この砂糖がミュータンス菌（Ｓｔ。In general, the cause of dental caries (cavity 1) formation is the tooth structure (T
aeth), Substrate, and Streptococcus mutans (St, mutans), and it is said that tooth decay occurs when these three factors exist simultaneously. The mechanism of caries formation is 1. For example, among sugars, sugar is used as a substrate.
In this case, this sugar is Streptococcus mutans (St.
ｍｕｔａｎｓ）の産出するグルコシルトランスフェラー
ゼ（酵素）によって水に不溶性で粘着性のデキストラン
（グルカン）に変化し、歯質（Ｔｅｅｔｈ）の表面に歯
垢を形成する。この歯垢の中では嫌気状態となり乳酸菌
等により醗酵が進み乳酸が生成してｐＨが低下し、この
乳酸が歯のエナメル質を脱灰し虫歯（う負）を形成する
とされている。It is converted into water-insoluble and sticky dextran (glucan) by glucosyltransferase (enzyme) produced by S. mutans, forming dental plaque on the surface of teeth. This plaque becomes anaerobic, and fermentation proceeds by lactic acid bacteria and the like, producing lactic acid, which lowers the pH. It is said that this lactic acid demineralizes tooth enamel and forms cavities.
従って、ストレプトコッカス・ミュータンス（Ｓｔ、ｍ
ｕｔａｎｓ）に代表される口腔内細菌の増殖を抑え歯垢
の形成を阻止することは虫歯（う負）の形成を予防する
有効な方法である。Therefore, Streptococcus mutans (St, m
Suppressing the growth of oral bacteria such as S. utans and inhibiting the formation of dental plaque is an effective method for preventing the formation of cavities.
本発明者等は歯垢の原因となるデキストラン（グルカン
）の形成に大きく関与している虫歯菌であるストレプト
コッカス・ミュータンス菌の生育を阻害する物質を探索
した結果、リナロール。The present inventors searched for a substance that inhibits the growth of Streptococcus mutans, a caries bacterium that is largely involved in the formation of dextran (glucan), which causes dental plaque, and found linalool.
トランス−ピノカルベオール、パラ−イソプロピルシク
ロヘキサノール、カンホレニックアルデヒド、γ−デカ
ラクトン及びγ−ウンデカラクトンから成る群から選ば
れた化合物の１種若しくは２種以上が非常に有効である
ことが判明した。これらの化合物は既に人体に安全であ
ることが確認されている公知香料物質であるが、この様
に口腔内で快い芳香を漂わせる香料物質がストレプトコ
ッカス・ミュータンス菌の育成を有効に阻害し得ること
はこれまで全く知られていない。One or more compounds selected from the group consisting of trans-pinocarveol, para-isopropylcyclohexanol, campholenic aldehyde, γ-decalactone and γ-undecalactone have been found to be highly effective. did. These compounds are known fragrance substances that have already been confirmed to be safe for the human body, but these fragrance substances that emit a pleasant aroma in the oral cavity can effectively inhibit the growth of Streptococcus mutans bacteria. This was completely unknown until now.
本発明のう負菌生育阻害剤の投与形態としては口腔中で
比較的滞留時間の長い錠菓、チューインガム、キャンデ
ー及びトローチ等に配合させることによりその効果が期
待できるほか、界面活性剤による抗菌活性の低下も殆ど
無いので歯磨及びマウスウォッシュ等の口腔清浄剤に配
合しても使用できる。その配合量は対象製品の形態、種
類等によって必ずしも一様でないが通常用いられる口腔
用組成物中ｏ、ｏｏｓ〜１０重量％、好ましくは０．０
５〜５重量％配合するのが一般的であり、この配合にて
有効にう負防止効果を発現する。As for the administration form of the caries growth inhibitor of the present invention, the effect can be expected by incorporating it into tablets, chewing gum, candies, troches, etc., which have a relatively long residence time in the oral cavity, and the antibacterial activity due to the surfactant. Since there is almost no decrease in the amount of water, it can be used even when added to oral cleansers such as toothpaste and mouthwash. The blending amount is not necessarily uniform depending on the form, type, etc. of the target product, but is in the range of o, oos to 10% by weight, preferably 0.0% by weight in the commonly used oral composition.
Generally, it is blended in an amount of 5 to 5% by weight, and this blend effectively exhibits the cavities prevention effect.
〈発明の効果〉 本発明のう負菌生育阻害剤は快い芳香を有し。<Effect of the invention> The caries growth inhibitor of the present invention has a pleasant aroma.
しかもう像画の生育を有効に阻害するのでその利用価値
は高いものである。Moreover, since it effectively inhibits the growth of degenerative images, its utility value is high.
〈実施例〉
以下に本発明につき抗菌活性効果を実施例により詳細に
説明する。<Example> The antibacterial activity effect of the present invention will be explained in detail below with reference to Examples.
（実施例−１）
ショ糖２％添加のハートインフュージョンブイヨンの液
体培地に５％−アルコール溶液とした試料化合物を試料
化合物濃度が０．１％（１／１０００濃度）となる様に
添加し、これに前培養しておいたストレプトコッカス・
ミュータンス（Ｓｔｒｅｐｔｏｃｏｃｃｕｓｍｕｔａｎ
ｓ） ３１２５００１株を白金耳により接種し、３７℃
にて２４時間培養した６次に培養液を攪拌し、沈澱物を
分散させた後、５５０ｎｍにおける吸光度（濁度）を測
定し、ミュータンス菌によるグルカン形成量をチェック
した。又、グルカン形成時にミュータンス菌による糖発
酵が生起し培地が酸性となることから、培養液のｐＨも
測定した。(Example-1) A sample compound made into a 5% alcohol solution was added to a heart infusion broth liquid medium supplemented with 2% sucrose so that the sample compound concentration was 0.1% (1/1000 concentration). , Streptococcus precultured on this
Streptococcus mutans
s) Inoculate the 3125001 strain with a platinum loop and keep at 37°C.
After culturing for 24 hours, the culture solution was stirred to disperse the precipitate, and the absorbance (turbidity) at 550 nm was measured to check the amount of glucan formed by Streptococcus mutans. Furthermore, since sugar fermentation by Streptococcus mutans occurs during glucan formation and the medium becomes acidic, the pH of the culture solution was also measured.
結果を表１に示す。The results are shown in Table 1.
尚、歯垢形成量は、コントロール（滅菌水）を１００％
とした場合の百分率で表わした。In addition, the amount of plaque formation is 100% of the control (sterilized water).
Expressed as a percentage.
表−１に示される様に、培地のＰＨ低下及びグルカン形
成は見られず、ミュータンス菌の生育を阻止するのに有
効であることが明白である。As shown in Table 1, no decrease in the pH of the medium and no glucan formation were observed, and it is clear that the method is effective in inhibiting the growth of S. mutans.
（実施例−２）
実施例−１に於いて培地のＰＨの低下及びグルカン形成
が全く認められなかった表−１の化合物について、実施
例−１と同じ培地及び同じ方法で、試料化合物を希釈し
て抗菌試験を実施し、各々化合物の最低有効阻止濃度を
測定した。最低有効阻止濃度試験の評価は、実施例−１
と同じく培地のｐＨの変化、及びグルカン形成量で判定
した０判定の結果、培地のｐＨの低下及びグルカン形成
が全く認められなかったものは抗菌活性があるとし、そ
の試験試料の最低有効濃度の逆数でもって抗ミュータン
ス菌活性値とした。その結果を表−２に示す。(Example-2) For the compounds in Table-1 for which no decrease in medium pH or glucan formation was observed in Example-1, the sample compound was diluted using the same medium and the same method as Example-1. An antibacterial test was conducted to determine the minimum effective inhibitory concentration of each compound. The evaluation of the minimum effective inhibitory concentration test is carried out in Example-1.
Similarly, as a result of the 0 judgment, which was determined based on the change in the pH of the culture medium and the amount of glucan formed, if no decrease in the pH of the culture medium and no glucan formation were observed, it is considered to have antibacterial activity, and the lowest effective concentration of the test sample is determined. The reciprocal number was used as the anti-Streptococcus mutans activity value. The results are shown in Table-2.
表−２より明らかなように、本発明の化合物はいずれも
高活性を示すことが明らかである。As is clear from Table 2, it is clear that all the compounds of the present invention exhibit high activity.
Claims (1)
プロピルシクロヘキサノール、カンホレニックアルデヒ
ド、γ−デカラクトン及びγ−ウンデカラクトンより成
る群から選ばれた化合物の少なくとも一種を有効成分と
して含有することを特徴とするう蝕菌生育阻害剤。It is characterized by containing as an active ingredient at least one compound selected from the group consisting of linalool, trans-pinocarveol, para-isopropylcyclohexanol, campholenic aldehyde, γ-decalactone, and γ-undecalactone. Cariogenic bacteria growth inhibitor.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61171683A JPH0717499B2 (en) | 1986-07-23 | 1986-07-23 | Caries fungus growth inhibitor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61171683A JPH0717499B2 (en) | 1986-07-23 | 1986-07-23 | Caries fungus growth inhibitor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6330409A true JPS6330409A (en) | 1988-02-09 |
| JPH0717499B2 JPH0717499B2 (en) | 1995-03-01 |
Family
ID=15927759
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61171683A Expired - Lifetime JPH0717499B2 (en) | 1986-07-23 | 1986-07-23 | Caries fungus growth inhibitor |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0717499B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012072179A (en) * | 2005-08-30 | 2012-04-12 | Kao Corp | Biofilm inhibitor |
| JP2012246234A (en) * | 2011-05-26 | 2012-12-13 | Kao Corp | Autoinducer-2 inhibitor |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5163970A (en) * | 1974-10-15 | 1976-06-02 | Int Flavors & Fragrances Inc |
-
1986
- 1986-07-23 JP JP61171683A patent/JPH0717499B2/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5163970A (en) * | 1974-10-15 | 1976-06-02 | Int Flavors & Fragrances Inc |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012072179A (en) * | 2005-08-30 | 2012-04-12 | Kao Corp | Biofilm inhibitor |
| JP2012246234A (en) * | 2011-05-26 | 2012-12-13 | Kao Corp | Autoinducer-2 inhibitor |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0717499B2 (en) | 1995-03-01 |
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