JP2022088563A - 抗微生物組成物 - Google Patents
抗微生物組成物 Download PDFInfo
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- JP2022088563A JP2022088563A JP2022055989A JP2022055989A JP2022088563A JP 2022088563 A JP2022088563 A JP 2022088563A JP 2022055989 A JP2022055989 A JP 2022055989A JP 2022055989 A JP2022055989 A JP 2022055989A JP 2022088563 A JP2022088563 A JP 2022088563A
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- methoxybenzaldehyde
- gamma
- Prior art date
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- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 claims abstract description 112
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Abstract
Description
本出願は、2016年8月5日に出願された米国仮特許出願番号第62/371,462号(U.S. Provisional Patent Application Serial No. 62/371,462)、及び2016年8月31日に出願された欧州特許出願番号第16186681.9号(European Patent Application Serial No. 16186681.9)に対して優先権を主張し、その全記載内容は参照をもってその全体を本明細書に組み込まれたものとする。
本開示は、抗微生物組成物及び抗菌薬としてのそれらの使用、又は抗微生物活性のある付香組成物及び消費者製品の製造のためのそれらの使用の分野に関する。より詳述すれば、本開示は、(i)3-ネオペンチルピリジン、2-メチルヘキサン-3-オンオキシム、テルピネオール及び2-イソプロピル-5-メチルフェノールからなる群から選択される少なくとも1つの成分と組み合わせてノナ-2,6-ジエン-1-オール、(ii)1-メチル-4-(1-メチルエテニル)-シクロヘキセン、4-メトキシベンズアルデヒド、及び1,3-ベンゾジオキソール-5-カルバルデヒドからなる群から選択される少なくとも1つの成分と組み合わせてガンマ-ドデカラクトン、(iii)(Z)-3,7-ジメチル-2,6-オクタジエン-1-オール及びガンマ-ドデカラクトン、(iv)シス-4(イソプロピル)シクロヘキサンメタノール及び4-メトキシベンズアルデヒド、並びに(v)1,3-ベンゾジオキソール-5-カルバルデヒド及び4-メトキシベンズアルデヒドからなる群から選択される組成物に関し、前記成分は、抗微生物効果を提供するために十分な量で存在し、かつ抗微生物効果は、黄色ブドウ球菌(S. aureus)(スタフィロコッカス・アウレウス)及び大腸菌(E. coli)(エシェリキア・コリー)からなる群から選択される細菌株の成長の阻害である。
衛生は、広義の主題であり、その最も完全な意味において、製品、プロセス及び装置に加えて、安全で健康的な環境を生じ、促進するための全ての事情及び慣習、生活習慣、並びに施設を含む。特に、衛生は、健康を維持し、病気の拡大を防ぐために役立つ条件及び慣習をいい、したがって、この健康の保存に関連する具体的な一連の慣習、例えば環境清掃、機器の滅菌、手指衛生、水及び下水処理、又は医療廃棄物の安全な処分を含む。
一態様において、本開示は、(i)3-ネオペンチルピリジン、2-メチルヘキサン-3-オンオキシム、テルピネオール及び2-イソプロピル-5-メチルフェノールからなる群から選択される少なくとも1つの成分と組み合わせてノナ-2,6-ジエン-1-オール、(ii)1-メチル-4-(1-メチルエテニル)-シクロヘキセン、4-メトキシベンズアルデヒド、及び1,3-ベンゾジオキソール-5-カルバルデヒドからなる群から選択される少なくとも1つの成分と組み合わせてガンマ-ドデカラクトン、(iii)(Z)-3,7-ジメチル-2,6-オクタジエン-1-オール及びガンマ-ドデカラクトン、(iv)シス-4(イソプロピル)シクロヘキサンメタノール及び4-メトキシベンズアルデヒド、並びに(v)1,3-ベンゾジオキソール-5-カルバルデヒド及び4-メトキシベンズアルデヒドからなる群から選択される成分を含む組成物を提供し、その際、前記成分は、抗微生物効果を提供するために十分な量で存在する。
いくつかの態様において、本開示は、(i)3-ネオペンチルピリジン、2-メチルヘキサン-3-オンオキシム、テルピネオール及び2-イソプロピル-5-メチルフェノールからなる群から選択される少なくとも1つの成分と組み合わせてノナ-2,6-ジエン-1-オール、(ii)1-メチル-4-(1-メチルエテニル)-シクロヘキセン、4-メトキシベンズアルデヒド、及び1,3-ベンゾジオキソール-5-カルバルデヒドからなる群から選択される少なくとも1つの成分と組み合わせてガンマ-ドデカラクトン、(iii)(Z)-3,7-ジメチル-2,6-オクタジエン-1-オール及びガンマ-ドデカラクトン、(iv)シス-4(イソプロピル)シクロヘキサンメタノール及び4-メトキシベンズアルデヒド、並びに(v)1,3-ベンゾジオキソール-5-カルバルデヒド及び4-メトキシベンズアルデヒドからなる群から選択される成分を含む組成物を提供し、その際、前記成分は、抗微生物効果を提供するために十分な量で存在する。いくつかの態様において、抗微生物効果は予想外である。
a)ノナ-2,6-ジエン-1-オールと、3-ネオペンチルピリジン、2-メチルヘキサン-3-オンオキシム、テルピネオール、及び2-イソプロピル-5-メチルフェノールからなる群から選択される少なくとも1つの化合物とを含む組成物、ここで該組成物は抗微生物効果を提供するために十分な量で存在するものとする、
b)香料キャリヤー、付香補助成分及びそれらの混合物からなる群から選択される少なくとも1つの成分、並びに
c)任意に、少なくとも1つの香料補助剤
を含む付香組成物を提供する。
a)少なくともガンマ-ドデカラクトンを1-メチル-4-(1-メチルエテニル)-シクロヘキセン、4-メトキシベンズアルデヒド及び1,3-ベンゾジオキソール-5-カルバルデヒドからなる群から選択される少なくとも1つの成分と組み合わせて含む組成物、ここで該組成物は抗微生物効果を提供するために十分な量で存在するものとする、
b)香料キャリヤー、付香補助成分及びそれらの混合物からなる群から選択される少なくとも1つの成分、並びに
c)任意に、少なくとも1つの香料補助剤
を含む付香組成物を提供する。
a)少なくとも1,3-ベンゾジオキソール-5-カルバルデヒドとガンマ-ドデカラクトンとを含む組成物、ここで該組成物は抗微生物効果を提供するために十分な量で存在するものとする、
b)香料キャリヤー、付香補助成分及びそれらの混合物からなる群から選択される少なくとも1つの成分、並びに
c)任意に、少なくとも1つの香料補助剤
を含む付香組成物を提供する。
a)少なくともシス-4(イソプロピル)シクロヘキサンメタノールと4-メトキシベンズアルデヒドとを含む組成物、ここで該組成物は抗微生物効果を提供するために十分な量で存在するものとする、
b)香料キャリヤー、付香補助成分及びそれらの混合物からなる群から選択される少なくとも1つの成分、並びに
c)任意に、少なくとも1つの香料補助剤
を含む付香組成物を提供する。
a)少なくとも1,3-ベンゾジオキソール-5-カルバルデヒドと4-メトキシベンズアルデヒドとを含む組成物、ここで該組成物は抗微生物効果を提供するために十分な量で存在するものとする、
b)香料キャリヤー、付香補助成分及びそれらの混合物からなる群から選択される少なくとも1つの成分、並びに
c)任意に、少なくとも1つの香料補助剤
を含む付香組成物を提供する。
- アルデヒド成分:デカナール、ドデカナール、2-メチル-ウンデカナール、10-ウンデカナール、オクタナール及び/又はノネナール;
- 芳香性ハーブ成分:ユーカリ油、樟脳、オイカリプトール、メントール及び/又はアルファ-ピネン;
- バルサム成分:クマリン、エチルバニリン及び/又はバニリン;
- シトラス成分、ジヒドロミリセノール、シトラール、オレンジ油、リナリルアセテート、シトロネリルニトリル、オレンジテルペン、リモネン、1-P-メンテン-8-イルアセテート及び/又は1,4(8)-P-メンタジエン;
- フローラル成分:メチルジヒドロジャスモネート、リナロール、シトロネロール、フェニルエタノール、3-(4-tert-ブチルフェニル)-2-メチルプロパナール、ヘキシルシンナムアルデヒド、ベンジルアセテート、ベンジルサリチレート、テトラヒドロ-2-イソブチル-4-メチル-4(2H)-ピラノール、ベータイオノン、メチル2-(メチルアミノ)ベンゾエート、(E)-3-メチル-4-(2,6,6-トリメチル-2-シクロヘキセン-1-イル)-3-ブテン-2-オン、ヘキシルサリチレート、3,7-ジメチル-1,6-ノナジエン-3-オール、3-(4-イソプロピルフェニル)-2-メチルプロパナール、バージルアセテート、ゲラニオール、P-メンタ-1-エン-8-オール、4-(1,1-ジメチルエチル)-1-シクロヘキシルアセテート、1,1-ジメチル-2-フェニルエチルアセテート、4-シクロヘキシル-2-メチル-2-ブタノール、アミルサリチレート、高シスメチルジヒドロジャスモネート、3-メチル-5-フェニル-1-ペンタノール、バージルプロピオネート、ゲラニルアセテート、テトラヒドロリナロール、シス-7-P-メタノール、プロピル(S)-2-(1,1-ジメチルプロポキシ)プロパノエート、2-メトキシナフタレン、2,2,2-トリクロロ-1-フェニルエチルアセテート、4/3-(4-ヒドロキシ-4-メチルペンチル)-3-シクロヘキセン-1-カルバルデヒド、アミルシンナムアルデヒド、4-フェニル-2-ブタノン、イソノニルアセテート、4-(1,1-ジメチルエチル)-1-シクロヘキシルアセテート、バージルイソブチレート及び/又はメチルイオノン異性体の混合物;
- フルーティー成分:ガンマウンガンマ-ドデカラクトンアセトン、4-デカノリド、エチル2-メチル-ペンタノエート、ヘキシルアセテート、エチル2-メチルブタノエート、ガンマノナラクトン、アリルヘプタノエート、2-フェノキシエチルイソブチレート、エチル2-メチル-1,3-ジオキソラン-2-アセテート及び/又はジエチル1,4-シクロヘキサンジカルボキシレート;
- グリーン成分:2,4-ジメチル-3-シクロヘキセン-1-カルバルデヒド、2-tert-ブチル-1-シクロヘキシルアセテート、スチラリルアセテート、アリル(2-メチルブトキシ)アセテート、4-メチル-3-デセン-5-オール、ジフェニルエーテル、(Z)-3-ヘキセン-1-オール及び/又は1-(5,5-ジメチル-1-シクロヘキセン-1-イル)-4-ペンテン-1-オン;
- ムスク成分:1,4-ジオキサ-5,17-シクロヘプタデカンジオン、ペンタデカノリド、3-メチル-5-シクロペンタデセン-1-オン、1,3,4,6,7,8-ヘキサヒドロ-4,6,6,7,8,8-ヘキサメチル-シクロペンタ-g-2-ベンゾピラン、(1S,1’R)-2-[1-(3’,3’-ジメチル-1’-シクロヘキシル)エトキシ]-2-メチルプロピルプロパノエート、ペンタデカノリド及び/又は(1S,1’R)-[1-(3’,3’-ジメチル-1’-シクロヘキシル)エトキシカルボニル]メチルプロパノエート;
- ウッディー成分:1-(オクタヒドロ-2,3,8,8-テトラメチル-2-ナフタレニル)-1-エタノン、パチュリ油、パチュリ油のテルペン画分、(1’R,E)-2-エチル-4-(2’,2’,3’-トリメチル-3’-シクロペンテン-1’-イル)-2-ブテン-1-オール、2-エチル-4-(2,2,3-トリメチル-3-シクロペンテン-1-イル)-2-ブテン-1-オール、メチルセドリルケトン、5-(2,2,3-トリメチル-3-シクロペンテニル)-3-メチルペンタン-2-オール、1-(2,3,8,8-テトラメチル-1,2,3,4,6,7,8,8a-オクタヒドロナフタレン-2-イル)エタン-1-オン及び/又はイソボルニルアセテート;
- 他の成分(例えばアンバー、パウダリースパイシー又はウォータリー):ドデカヒドロ-3a,6,6,9a-テトラメチル-ナフト[2,1-b]フラン及び任意のその立体異性体、ヘリオトロピン、アニスアルデヒド、オイゲノール、シンナムアルデヒド、チョウジ油、3-(1,3-ベンゾジオキソール-5-イル)-2-メチルプロパナール及び/又は3-(3-イソプロピル-1-フェニル)ブタナール。
本開示は、次の実施例によってさらに詳細に記載され、その際略語は、当該技術分野において通常の意味を有し、温度は、摂氏度(℃)で示される。
本開示による組成物の抗微生物活性の測定
抗微生物活性の評価方法
以下の方法は、異なる原料の抗微生物活性を組み合わせて評価することを可能にする。分画阻止濃度指数(FIC指数)は活性の測定であり(Garcia L.S.、Clinical Microbiology Procedures Handbook、140~162頁、第3版(2010年)、ASM Press、Washington DC)、以下の式に従って算出される:
大腸菌DSMZ 1103及び黄色ブドウ球菌DSMZ 1104の細菌懸濁液を、以下のように製造した:凍結させたストックのアリコートを、トリプチックソイ寒天(Tryptic Soy Agar)プレート上にストリークし、そして37℃で24時間インキュベートした。シングル細菌コロニーを選び取り、そして100mlフラスコ中に含んだミューラーヒントンブロス(Mueller Hinton Broth)50ml中に植え付けた。撹拌(160rpm)下で、37℃で一晩インキュベーションを実施した。翌日、一晩培養物を、新鮮なミューラーヒントンブロス50ml中にそれぞれ黄色ブドウ球菌について1:50及び大腸菌について1:100で希釈した。37℃での生育を、600nmで測定した吸光度がそれぞれ黄色ブドウ球菌について0.7~0.9及び大腸菌について0.3~0.45に達するまで、前記したように続けた。この時点で、細胞を、遠心分離(10分-500×g-4℃)により採取し、そして1×108CFU/mlの濃度で新鮮なミューラーヒントンブロス中で懸濁した。
評価中の原料(成分A及びB)の溶液をエタノール中で製造し、そして96ウェルマイクロタイタープレート(1ウェル毎に10μl)中に所望の濃度で段階希釈した。1列目、10列目、11列目及び12列目には、あらゆる試験材料なしでエタノール10μlのみを入れた。エタノールの最終濃度は、全てのウェルについて5%(w/v)であった。
前記試験に基づいて、原料の次の組み合わせが、大腸菌DSMZ 1103に対する抗微生物活性を示すことを見出した。
液体石鹸ベースにおける本明細書において示したいくつかの態様に従った組成物の抗菌効果
細菌溶液の製造
2つの株、大腸菌DSMZ 1103及び黄色ブドウ球菌DSMZ 1104の細菌溶液を、次のようにBCT試験のために製造した。-80℃で貯蔵したストック培養物を、トリプチックソイ寒天(TSA)の寒天プレート培地上で継代培養し、そして24時間37℃でインキュベートして、シングルコロニーを得た。初代培養物のシングルコロニーを、TSA斜面上にストリークし、そして24時間37℃のインキュベーターでインキュベートした。斜面培養の細菌叢を、PBS緩衝液中に採取し、標的レベル1~5×108CFU/mLを有する懸濁液を作った。それぞれの細胞懸濁液のPBS緩衝液中での1:100希釈物を、BCT試験のための細菌溶液として使用した。
相乗的二成分混合物を有するベースの試験試料を以下のように製造した。相乗的二成分混合物の原料(表17)を、液体石鹸ベースPGK-10-003(表18)と混合した。それぞれの混合物のアリコート(2.5g)を、撹拌棒と一緒に20mlガラス管に秤量し、そして等量のMilliQ水を添加して、BCT試験のための試験試料として50%懸濁液を作った。
BCT試験を20mlサンプルチューブで実施した。50%試料懸濁液5gを有するそれぞれのサンプルチューブを、磁気撹拌機上に置き、そして細菌溶液のアリコート(100μl)を試料に添加して、混合しながら45秒間接触させた。そして、混合物のアリコート(0.5ml)を、PBS5ml中に移し、そしてさらに段階希釈液をPBS4.5ml中で作った。PBS希釈液のアリコート(0.5ml)を、混釈平板法を使用してTSAプレートの複製プレート上に置いた。TSAプレートを37℃で48時間インキュベートした。インキュベート後に、TSAプレート上のコロニーを数え、それぞれの試料の対数減少を、対照試料(MilliQ水)のCFU数に対して算出した。
ロールオンデオドラントベースにおける本明細書において示したいくつかの態様に従った組成物の抗菌効果
細菌溶液の製造
C.ゼロシースATCC 373株の細菌溶液を、次のようにBCT試験のために製造した。-80℃で貯蔵したストック培養物を、0.5%Tween80を加えたトリプチックソイ寒天培地(TSA-TW80)上で継代培養し、そして48時間37℃でインキュベートした。初代培養物を、再度TSA-TW80上に継代培養して、二次培養物を製造した。二次培養物のシングルコロニーを、0.5%Tween80を加えたブレインハートインフュージョン(BHI)培地(BHI-TW80)30ml中に植え付け、そして37℃180rpmで24時間インキュベートした。24時間培養物のアリコート(1ml)を新鮮なBHI-TW80培地30mlに植え付け、そして37℃180rpmで48時間インキュベートした。48時間培養物のアリコート(2~3ml)を4つの新鮮なBHI-TW80培地50mlに植え付け、そして37℃180rpmで4~6時間インキュベートした。ODが標的値1.6に達したら、細胞を、10分間5000rpmで遠心分離によって採取し、そして標的濃度109~1010cfu/mLまで同一の新鮮な培地中に再懸濁させた。この懸濁液を、BCT試験のための細菌溶液として使用した。
相乗的二成分混合物を有するベースの試験試料を以下のように製造した。相乗的二成分混合物の原料を秤量し(表22)、そしてPEG-40硬化ヒマシ油0.3g及びデオドラントロールオンベース(表23)9.57gと混合した。
BCT試験を15mlサンプルチューブで実施した。それぞれの試料のアリコート(0.9g)を、チューブに秤量し、そして細菌溶液のアリコート(100μl)を試料に添加し、一定に混合しながら120秒間接触させた。接触時間の終わりに、BHI培地のアリコート(9ml)をチューブに添加した。その懸濁液をボルテックスにより十分に混合し、そしてさらに1:10の段階希釈液をBHI9.9ml中で作った。BHI希釈液のアリコート(1ml)を、混釈平板法を使用してTSA-TW80の複製プレート上に置いた。TSA-TW80プレートを37℃で2~3日間インキュベートした。インキュベート後に、TSA-TW80プレート上のコロニーを数え、それぞれの試料の対数減少を、対照試料(BHI)のCFU計数に対して算出した。
Claims (15)
- (i)3-ネオペンチルピリジン、2-メチルヘキサン-3-オンオキシム、テルピネオール及び2-イソプロピル-5-メチルフェノールからなる群から選択される少なくとも1つの成分と組み合わせてノナ-2,6-ジエン-1-オール、(ii)1-メチル-4-(1-メチルエテニル)-シクロヘキセン、4-メトキシベンズアルデヒド及び1,3-ベンゾジオキソール-5-カルバルデヒドからなる群から選択される少なくとも1つの成分と組み合わせてガンマ-ドデカラクトン、(iii)(Z)-3,7-ジメチル-2,6-オクタジエン-1-オール及びガンマ-ドデカラクトン、(iv)シス-4(イソプロピル)シクロヘキサンメタノール及び4-メトキシベンズアルデヒド、並びに(v)1,3-ベンゾジオキソール-5-カルバルデヒド及び4-メトキシベンズアルデヒドからなる群から選択される成分を含有する組成物であって、前記成分が、抗微生物効果を提供するために十分な量で存在し、前記抗微生物効果が、C.ゼロシース(C. xerosis)、黄色ブドウ球菌(S. aureus)及び大腸菌(E. coli)からなる群から選択される細菌株の成長の阻害である、前記組成物。
- さらに、香料キャリヤー、付香補助成分及びそれらの混合物からなる群から選択される少なくとも1つの成分、並びに任意に少なくとも1つの香料補助剤を含有する、請求項1に記載の組成物。
- 消費者製品として配合される請求項2に記載の組成物であって、消費者製品が、香水、布地ケア製品、ボディケア製品、化粧品調製物、スキンケア製品、エアケア製品又はホームケア製品である、前記組成物。
- ノナ-2,6-ジエン-1-オールと、3-ネオペンチルピリジン、テルピネオール及び2-メチルヘキサン-3-オンオキシムからなる群から選択される少なくとも1つの化合物とを含む、請求項1に記載の組成物。
- ノナ-2,6-ジエン-1-オールの十分な量が75~300ppmであり、3-ネオペンチルピリジンの十分な量が75~150ppmであり、テルピネオールの十分な量が300~600ppmであり、かつ2-メチルヘキサン-3-オンオキシムの十分な量が1000~1200ppmである、請求項4に記載の組成物。
- ノナ-2,6-ジエン-1-オールと、2-イソプロピル-5-メチルフェノール及び3-ネオペンチルピリジンからなる群から選択される少なくとも1つの化合物とを含む、請求項1に記載の組成物。
- ノナ-2,6-ジエン-1-オールの十分な量が75~300ppmであり、2-イソプロピル-5-メチルフェノールの十分な量が100~200ppmであり、かつ3-ネオペンチルピリジンの十分な量が75~150ppmである、請求項6に記載の組成物。
- ガンマ-ドデカラクトンと、4-メトキシベンズアルデヒド及び1,3-ベンゾジオキソール-5-カルバルデヒドからなる群から選択される少なくとも1つの化合物とを含む、請求項1に記載の組成物。
- ガンマ-ドデカラクトンの十分な量が150~600ppmであり、4-メトキシベンズアルデヒドの十分な量が300~600ppmであり、かつ1,3-ベンゾジオキソール-5-カルバルデヒドの十分な量が300~600ppmである、請求項8に記載の組成物。
- (Z)-3,7-ジメチル-2,6-オクタジエン-1-オールとガンマ-ドデカラクトンとを含む、請求項1に記載の組成物。
- (Z)-3,7-ジメチル-2,6-オクタジエン-1-オールの十分な量が150~300ppmであり、かつガンマ-ドデカラクトンの十分な量が150~600ppmである、請求項10に記載の組成物。
- シス-4(イソプロピル)シクロヘキサンメタノールと4-メトキシベンズアルデヒドとを含む、請求項1に記載の組成物。
- シス-4(イソプロピル)シクロヘキサンメタノールの十分な量が600~2400ppmであり、かつ4-メトキシベンズアルデヒドの十分な量が150~300ppmである、請求項12に記載の組成物。
- 1,3-ベンゾジオキソール-5-カルバルデヒドと4-メトキシベンズアルデヒドとを含む、請求項1に記載の組成物。
- 1,3-ベンゾジオキソール-5-カルバルデヒドの十分な量が75~300ppmであり、かつ4-メトキシベンズアルデヒドの十分な量が150~300ppmである、請求項14に記載の組成物。
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CN114794101A (zh) | 2022-07-29 |
US20190201300A1 (en) | 2019-07-04 |
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