Antimicrobially active 4-methyl-4-aryl-2-pentanols, their preparation and use
View Patent ↗Antimicrobially active 4-methyl-4-aryl-2-pentanols of the Formula 1 below, methods for the preparation of these compounds and their use as antimicrobial active compounds are described. Surprisingly, compounds of the Formula 1 for which: R=hydrogen, hydroxyl, alkoxy group with up to 10 C atoms, straight-chain or branched, saturated or unsaturated alkyl with up to 10 C atoms, alkylthioether group with up to 10 C atoms, the alkylthioether group being bonded to the aromatic ring via a thioether bridge, fluorine, chlorine, bromine, iodine, or alkyl with up to 10 C atoms that is interrupted by one or more oxygen and/or sulphur atoms, have proved to be antimicrobially active.
1. Method for the cosmetic and/or therapeutic treatment of (a) microorganisms causing dandruff, (b) microorganisms causing body odour, (c) microorganisms causing acne and/or (d) microorganisms causing mycoses, comprising:
topically applying to a human or animal body suffering from (a) microorganisms causing dandruff, (b) microorganisms causing body odour, (c) microorganisms causing acne and/or (d) microorganisms causing mycoses, an antimicrobially active amount of one or more compounds of the Formula 1
wherein R=hydrogen, hydroxyl, alkoxy group with up to 10 C atoms, straight-chain or branched, saturated or unsaturated alkyl with up to 10 C atoms, alkylthioether group with up to 10 C atoms, the alkylthioether group being bonded to the aromatic ring via a thioether bridge, fluorine, chlorine, bromine, iodine, or alkyl with up to 10 C atoms that is interrupted by one or more oxygen and/or sulphur atoms.
2. A method for controlling microorganisms by applying to a microbial population comprising microorganisms that cause dandruff an antimicrobially active composition that comprises a compound according to Formula 1
where R=
hydrogen,
hydroxyl,
alkoxy group with up to 10 C atoms,
straight-chain or branched, saturated or unsaturated alkyl with up to 10 C atoms,
alkylthioether group with up to 10 C atoms, the alkylthioether group being bonded to the aromatic ring via a thioether bridge,
fluorine, chlorine, bromine, iodine, or
alkyl with up to 10 C atoms that is interrupted by one or more oxygen and/or sulphur atoms.
3. A method for controlling microorganisms by applying to a microbial population comprising microorganisms that cause body odour an antimicrobially active composition that comprises a compound according to Formula 1
where R=
hydrogen,
hydroxyl,
alkoxy group with up to 10 C atoms,
straight-chain or branched, saturated or unsaturated alkyl with up to 10 C atoms,
alkylthioether group with up to 10 C atoms, the alkylthioether group being bonded to the aromatic ring via a thioether bridge,
fluorine, chlorine, bromine, iodine, or
alkyl with up to 10 C atoms that is interrupted by one or more oxygen and/or sulphur atoms.
4. A method for controlling microorganisms according to claim 3 by applying said antimicrobially active compound to a microbial population comprising microorganisms that grow aerobically.
5. A method for controlling microorganisms by applying to a microbial population that comprises Propionibacterium acnes an antimicrobially active composition that comprises a compound according to Formula 1
where R=
hydrogen,
hydroxyl,
alkoxy group with up to 10 C atoms,
straight-chain or branched, saturated or unsaturated alkyl with up to 10 C atoms,
alkylthioether group with up to 10 C atoms, the alkylthioether group being bonded to the aromatic ring via a thioether bridge,
fluorine, chlorine, bromine, iodine, or
alkyl with up to 10 C atoms that is interrupted by one or more oxygen and/or sulphur atoms.
6. A method for controlling microorganisms by applying said to a microbial population comprising microorganisms that cause mycoses an antimicrobially active composition that comprises a compound according to Formula 1
where R=
hydrogen,
hydroxyl,
alkoxy group with up to 10 C atoms,
straight-chain or branched, saturated or unsaturated alkyl with up to 10 C atoms,
alkylthioether group with up to 10 C atoms, the alkylthioether group being bonded to the aromatic ring via a thioether bridge,
fluorine, chlorine, bromine, iodine, or
alkyl with up to 10 C atoms that is interrupted by one or more oxygen and/or sulphur atoms.
7. A method according to claim 3 wherein R=hydrogen.
8. A method according to claim 1 wherein R=hydrogen.
9. A deodorant comprising the following components:
(a) an antimicrobially active amount of one or more compounds of the Formula 1
where R=
hydrogen,
hydroxyl,
alkoxy group with up to 10 C atoms,
straight-chain or branched, saturated or unsaturated alkyl with up to 10 C atoms,
alkylthioether group with up to 10 C atoms, the alkylthioether group being bonded to the aromatic ring via a thioether bridge,
fluorine, chlorine, bromine, iodine, or
alkyl with up to 10 C atoms that is interrupted by one or more oxygen and/or sulphur atoms as well as
(b) a carrier substance compatible with component (a).
10. A deodorant comprising a composition which is present in an amount sufficient to suppress growth of odor-causing bacteria on human skin, said composition comprising the following components:
(a) an antimicrobially active amount of one or more compounds of the Formula 1
where R=
hydrogen,
hydroxyl,
alkoxy group with up to 10 C atoms,
straight-chain or branched, saturated or unsaturated alkyl with up to 10 C atoms,
alkylthioether group with up to 10 C atoms, the alkylthioether group being bonded to the aromatic ring via a thioether bridge,
fluorine, chlorine, bromine, iodine, or
alkyl with up to 10 C atoms that is interrupted by one or more oxygen and/or sulphur atoms as well as
(b) a carrier substance compatible with component (a).
11. A method according to claim 3 wherein said microorganism population includes a bacteria.
12. A deodorant according to claim 9 wherein said carrier comprises water, an aqueous gel, an aqueous cream, or an oil-in-water emulsion.
13. A deodorant according to claim 9 in the form of a topically applied cosmetic formulation.
14. A method according to claim 11 wherein said bacteria causes underarm or foot odor.
15. A method according to claim 14 wherein said bacteria causes underarm odor.
16. A deodorant according to claim 9 wherein said compound is present in an amount sufficient to control odor-causing bacteria on underarm human skin.
17. A deodorant according to claim 9 wherein said compound is present in an amount between 0.0069 and 20 wt % based on total weight.
18. A deodorant according to claim 9 wherein said compound is present in an amount between 0.05 and 5 wt % based on total weight.
19. A deodorant according to claim 9 wherein R=hydrogen.
20. A deodorant according to claim 9 wherein R=hydroxyl.
21. A deodorant according to claim 9 wherein
R=alkoxy group with up to C atoms, or straight-chain or branched, saturated or unsaturated alkyl with up to 10 C atoms.
22. A deodorant according to claim 9 wherein said carrier comprises water, an aqueous gel, an aqueous cream, or an oil-in-water emulsion.
23. A deodorant according to claim 10 wherein said compound is present in an amount between 0.0069 and 20 wt % based on total weight.
24. A deodorant according to claim 10 wherein said compound is present in an amount between 0.05 and 5 wt % based on total weight.
25. A deodorant according to claim 10 wherein R=hydrogen.
26. A deodorant according to claim 10 wherein R=hydroxyl.
27. A deodorant according to claim 10 wherein
R=alkoxy group with up to 10 C atoms, or straight-chain or branched, saturated or unsaturated alkyl with up to 10 C atoms.
28. A deodorant according to claim 10 wherein said carrier comprises water, an aqueous gel, an aqueous cream, or an oil-in-water emulsion.
29. A method according to claim 14 wherein said microorganism population comprises Staphylococcus epidermidis, Corynebacterium xerosis or Brevibacterium epidermidis.