WO2018024886A2 - Antimicrobial composition - Google Patents
Antimicrobial composition Download PDFInfo
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- WO2018024886A2 WO2018024886A2 PCT/EP2017/069804 EP2017069804W WO2018024886A2 WO 2018024886 A2 WO2018024886 A2 WO 2018024886A2 EP 2017069804 W EP2017069804 W EP 2017069804W WO 2018024886 A2 WO2018024886 A2 WO 2018024886A2
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- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000162 poly(ureaurethane) Polymers 0.000 description 1
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- 229920000768 polyamine Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- GWFJURKHPPFFMD-UHFFFAOYSA-N prop-2-enyl 2-(2-methylbutoxy)acetate Chemical compound CCC(C)COCC(=O)OCC=C GWFJURKHPPFFMD-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 239000002884 skin cream Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 1
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 1
- ICUTUKXCWQYESQ-UHFFFAOYSA-N triclocarban Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC1=CC=C(Cl)C(Cl)=C1 ICUTUKXCWQYESQ-UHFFFAOYSA-N 0.000 description 1
- 229960001325 triclocarban Drugs 0.000 description 1
- 239000001069 triethyl citrate Substances 0.000 description 1
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- 150000004043 trisaccharides Chemical class 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- RGVQNSFGUOIKFF-UHFFFAOYSA-N verdyl acetate Chemical compound C12CC=CC2C2CC(OC(=O)C)C1C2 RGVQNSFGUOIKFF-UHFFFAOYSA-N 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
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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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/02—Acyclic compounds
-
- 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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals
-
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/31—Hydrocarbons
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/342—Alcohols having more than seven atoms in an unbroken chain
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/347—Phenols
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/35—Ketones, e.g. benzophenone
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/005—Antimicrobial preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
Definitions
- the present disclosure relates to the field of antimicrobial compositions and their use as antibacterial agents, or their use for the preparation of antimicrobially active perfuming compositions and consumer products. More particularly, the present disclosure relates to compositions selected from the group consisting of: (i) nona-2,6-dien-l-ol in combination with at least one ingredient selected from the group consisting of 3-neopentylpyridine, 2- methylhexan-3-one oxime, terpineol and 2-isopropyl-5-methylphenol; (ii) gamma- dodecalactonein combination with at least one ingredient selected from the group consisting of l-Methyl-4-(l-methylethenyl)-cyclohexene, 4-Methoxybenzaldehyde, and 1,3- Benzodioxole-5-carbaldehyde; (iii) (Z)-3,7-Dimethyl-2,6-octadien-l-ol and
- Hygiene is a vast subject, which in its fullest meaning goes beyond simple 'cleanliness' to include, in addition to products, processes and devices, all circumstances and practices, lifestyle habits and premises that engender and foster a safe and healthy environment.
- hygiene refers to conditions and practices that help to maintain health and prevent the spread of diseases and therefore includes a specific set of practices associated with this preservation of health, for example environmental cleaning, sterilization of equipment, hand hygiene, water and sanitation or safe disposal of medical waste.
- U.S. Patent No. 7,759,058 discloses an antimicrobial composition containing at least 30% by weight of one or more perfuming ingredients including nona-2,6- dien-l-ol.
- WO2005079573 reports a fragrance composition providing, as expected, an organoleptic effect but also an antifungal activity in a vapor phase.
- the antifungal composition comprises at least 50% by weight of the total composition of at least two perfuming ingredients selected from several lists of ingredients comprising among others 2,6-nonadienol and thymol.
- perfuming ingredients selected from several lists of ingredients comprising among others 2,6-nonadienol and thymol.
- a large amount of perfuming ingredients is required to deliver antimicrobial properties, which strongly influences the odor profile of the end-product containing those compositions, therefore limiting their use as an antimicrobial agent.
- U.S. Patent No. 9,339,477 discloses an antimicrobial composition for personal cleaning, oral care or hard surface cleaning applications. Wherein, it was found that compositions comprising thymol, selected propen-2-yl-methyl- cyclohexanols, and a carrier provide synergistic antimicrobial action.
- U.S. Patent No. 5,453,276 discloses antimicrobial compositions for controlling P. aeruginosa or P. acnes which contains indole and a naturally occurring substance selected from the group consisting of anacardic acid, limonene, beta-pinene, farnesol, beta -citronellol, pine resin, hinokitiol, longifolene, and beta -caryophyllene.
- compositions having an antimicrobial effect comprising ingredients having a minor impact on the overall perfume profile of the product in which the composition is added while maintaining or even improving the efficacy of the compositions in order to shorter contact time required for effective antimicrobial action.
- compositions selected from the group consisting of: (i) nona-2,6- dien-l-ol in combination with at least one ingredient selected from the group consisting of 3- neopentylpyridine, 2-methylhexan-3-one oxime, terpineol and 2-isopropyl-5-methylphenol; (ii) gamma-dodecalactone in combination with at least one ingredient selected from the group consisting of l-Methyl-4-(l-methylethenyl)-cyclohexene, 4-Methoxybenzaldehyde, and l,3-Benzodioxole-5-carbaldehyde; (iii) (Z)-3,7-Dimethyl-2,6-octadien-l-ol and gamma- dodecalactone; (iv) cis-4(Isopropyl)cyclohexa
- the present disclosure provides a composition
- a composition comprising ingredients selected from the group consisting of: (i) nona-2,6-dien-l-ol in combination with at least one ingredient selected from the group consisting of 3-neopentylpyridine, 2-methylhexan-3-one oxime, terpineol and 2-isopropyl-5-methylphenol; (ii) gamma-dodecalactone in combination with at least one ingredient selected from the group consisting of l-Methyl-4-(l- methylethenyl)-cyclohexene, 4-Methoxybenzaldehyde, and l,3-Benzodioxole-5- carbaldehyde; (iii) (Z)-3,7-Dimethyl-2,6-octadien-l-ol and gamma-dodecalactone; (iv) cis- 4(Isopropyl)cyclohexanemethanol and 4-Met
- the composition provides the antimicrobial effect by inhibiting the growth of bacteria.
- the antimicrobial effect is an inhibition of growth of a bacterial strain selected from the group consisting of: C. xerosis, S. aureus and E. coli.
- the present invention provides a method, comprising treating a substrate comprising microbes with a composition according to some aspects of the present disclosure, in an amount effective to provide an antimicrobial effect.
- the composition comprises nona-2,6-dien-l-ol and at least one compound selected from the group consisting of 3-neopentylpyridine, terpineol, and 2- methylhexan-3-one oxime.
- the amount sufficient of the nona-2,6-dien-l-ol is from 75 to 300 ppm
- the amount sufficient of the 3-neopentylpyridine is from 75 to 150 ppm
- the amount sufficient of the terpineol is from 300 to 600 ppm
- the amount sufficient of the 2-methylhexan-3-one oxime is from 1000 to 1200 ppm.
- the composition comprises nona-2,6-dien-l-ol and at least one compound selected from the group consisting of 2-isopropyl-5-methylphenol, and 3- neopentylpyridine.
- the amount sufficient of the nona-2,6-dien-l-ol is from 75 to 300 ppm
- the amount sufficient of the 2-isopropyl-5-methylphenol is from 100 to 200 ppm
- the amount sufficient of the 3-neopentylpyridine is from 75 to 150 ppm.
- the composition comprises gamma-dodecalactone and at least one compound selected from the group consisting of 4-Methoxybenzaldehyde, and 1,3- Benzodioxole-5-carbaldehyde.
- the amount sufficient of the gamma- dodecalactone is from 150 to 600 ppm
- the amount sufficient of the 4-Methoxybenzaldehyde is from 300 to 600 ppm
- the amount sufficient of the l,3-Benzodioxole-5-carbaldehyde is from 300 to 600 ppm.
- the composition comprises (Z)-3,7-Dimethyl-2,6-octadien-l-ol and gamma-dodecalactone. In one aspect, the amount sufficient of the (Z)-3,7-Dimethyl-2,6- octadien-l-ol is from 150 to 300 ppm, and the amount sufficient of the gamma-dodecalactone is from 150 to 600 ppm. In one aspect, the composition comprises cis-4(Isopropyl)cyclohexanemethanol and 4-Methoxybenzaldehyde.
- the amount sufficient of the cis- 4(Isopropyl)cyclohexanemethanol is from 600 to 2400 ppm, and the amount sufficient of the 4-Methoxybenzaldehyde is from 150 to 300 ppm.
- the composition comprises l,3-Benzodioxole-5-carbaldehyde and 4-
- the amount sufficient of the l,3-Benzodioxole-5- carbaldehyde is from 75 to 300 ppm, and the amount sufficient of the 4- Methoxybenzaldehyde is from 150 to 300 ppm.
- the composition further comprises at least one ingredient selected from the group consisting of a perfumery carrier, a perfuming co-ingredient and mixtures thereof; and optionally at least one perfumery adjuvant.
- the composition is formulated as a consumer product, wherein the consumer product is a perfume, a fabric care product, a body-care product, a cosmetic preparation, a skin-care product, an air care product or a home care product.
- the consumer product is a fine perfume, a splash or eau de perfume, a cologne, an shave or after-shave lotion, a liquid or solid detergent, a fabric softener, a fabric refresher, an ironing water, a paper, a bleach, a carpet cleaners, curtain-care products a shampoo, a coloring preparation, a color care product, a hair shaping product, a dental care product, a disinfectant, an intimate care product, a hair spray, a vanishing cream, a deodorant or antiperspirant, hair remover, tanning or sun product, nail products, skin cleansing, a makeup, a perfumed soap, shower or bath mousse, oil or gel, or a foot/hand care products, a hygiene product, an air freshness, a fine
- the present disclosure provides a composition comprising ingredients selected from the group consisting of: (i) nona-2,6-dien-l-ol in combination with at least one ingredient selected from the group consisting of 3-neopentylpyridine, 2-methylhexan-3-one oxime, terpineol and 2-isopropyl-5-methylphenol; (ii) gamma-dodecalactone in combination with at least one ingredient selected from the group consisting of l-Methyl-4-(l- methylethenyl)-cyclohexene, 4-Methoxybenzaldehyde, and l,3-Benzodioxole-5- carbaldehyde; (iii) (Z)-3,7-Dimethyl-2,6-octadien-l-ol and gamma-dodecalactone; (iv) cis- 4(Isopropyl)cyclohexanemethanol and 4-Methoxy
- the composition provides the antimicrobial effect by inhibiting the growth of bacteria.
- the antimicrobial effect is an inhibition of growth of a bacterial strain selected from the group consisting of: C. xerosis, S. aureus and E. coli.
- the individual ingredients themselves possess an antimicrobial activity; however, the amount sufficient to provide the antimicrobial effect for the individual ingredient when combined in the composition is less than the amount sufficient to provide the antimicrobial effect of a given individual ingredient used separately.
- the amount sufficient to provide an antimicrobial effect has no impact on the overall odour profile of the composition.
- composition of the present disclosure enables the amount of other bioactive ingredients such as, for example, triclosan, to be reduced, without impacting the overall perfume profile as the antimicrobial effect of the composition is obtained at low dosages.
- the present disclosure provides a use, or a method of use of a composition
- a composition comprising ingredients selected from the group consisting of: (i) nona-2,6-dien- l-ol in combination with at least one ingredient selected from the group consisting of 3- neopentylpyridine, 2-methylhexan-3-one oxime, terpineol and 2-isopropyl-5-methylphenol; (ii) gamma-dodecalactone in combination with at least one ingredient selected from the group consisting of l-Methyl-4-(l-methylethenyl)-cyclohexene, 4-Methoxybenzaldehyde, and l,3-Benzodioxole-5-carbaldehyde; (iii) (Z)-3,7-Dimethyl-2,6-octadien-l-ol and gamma- dodecalactone; (iv) cis-4(Isopropyl)
- terpineol it is meant the normal meaning in the art; i.e. or-terpineol, ?-terpineol, ⁇ terpineol, terpinen-4-ol or mixture thereof.
- the terpineol presents in the composition is Qf-terpineol or terpinen-4-ol.
- terpineol presents in the composition is or-terpineol.
- the compound has the following structure:
- Nona-2,6-dien-l-ol may be in a form of any one of its stereoisomers or a mixture thereof.
- Nona-2,6-dien-l-ol has two carbon-carbon double bonds.
- Each carbon-carbon double bond of the compound, independently from each other can be in a configuration Z or E or a mixture thereof.
- each carbon-carbon double bond of the compound, independently from each other can be in a configuration Z or E or a mixture thereof it is meant also a composition of matter comprising the various ( ⁇ , ⁇ ), (E,Z), (Z,E) and (Z,Z) isomers of nona-2,6-dien-l-ol.
- (2E, 6Z)- nona-2,6-dien-l-ol is used.
- nona-2,6-dien-l-ol has the following structure:
- the ingredient 2-isopropyl-5-methylphenol is also known under the name Thymol, or the compound having the following structure:
- the ingredient 2-methylhexan-3-one oxime is also known as vertoxime, compound having the s
- the ingredient 3-neopentylpyridine is also known as fructopyridine, or the compound having the structure:
- the ingredient 2-isopropyl-5-metylpolyphenol is also known as limonene, decomposed Portugal.
- the ingredient 4-methoxybenzaldehyde is also known as anisic aldeyhde, or compound havin the structure:
- the ingredient l,3-benzodioxole-5-carbaldehyde is also known as heliotropine, or the compound having the structure:
- the ingredient (Z)-3,7-dimethyl-2,6-octadien-l-ol is also known as geraniol, or the compound having the s
- the ingredient cis-4(isopropyl)cyclohexanemethanol is also known as mayol, or the compound having the structure:
- the ingredient gamma-dodecalactone is also known as decal, or the compound having the structure:
- the composition is used as an antibacterial agent.
- a non-limiting list of bacteria for which the composition are particularly effective includes Escherichia coli, DSMZ 1103 (origin: DSMZ - Deutsche Sammlung von Mikroorganismen und Zellkulturen GmbH) or Staphylococcus aureus, DSMZ 1104 (origin : DSMZ - Deutsche Sammlung von Mikroorganismen und Zellkulturen GmbH), or Corynebacterium xerosis, ATCC 373 (origin: ATCC - American Type Culture Collection).
- the present disclosure provides an antimicrobial composition comprising nona-2,6-dien-l-ol and at least one compound selected from the group consisting of 3-neopentylpyridine, terpineol, and 2-methylhexan-3-one oxime.
- the present disclosure provides the use of a composition comprising nona-2,6-dien-l- ol and at least one compound selected from the group consisting of 3-neopentylpyridine, terpineol, and 2-methylhexan-3-one oxime as an antimicrobial agent.
- the present disclosure provides an antimicrobial composition comprising nona-2,6-dien-l-ol and at least one compound selected from the group consisting of 2-isopropyl-5-methylphenol, and 3-neopentylpyridine.
- the present disclosure provides the use of a composition comprising nona-2,6-dien-l-ol and at least one compound selected from the group consisting of 2-isopropyl-5-methylphenol, and 3-neopentylpyridine as an antimicrobial agent.
- the present disclosure provides an antimicrobial composition comprising gamma-dodecalactone and at least one compound selected from the group consisting of 4-Methoxybenzaldehyde, and l,3-Benzodioxole-5-carbaldehyde.
- the present disclosure provides the use of a composition comprising gamma- dodecalactone and at least one compound selected from the group consisting of 4- Methoxybenzaldehyde, and l,3-Benzodioxole-5-carbaldehyde as an antimicrobial agent.
- the present disclosure provides an antimicrobial composition comprising gamma-dodecalactone and l-Methyl-4-(l-methylethenyl)-cyclohexene.
- the present disclosure provides the use of a composition comprising gamma-dodecalactone and l-Methyl-4-(l-methylethenyl)-cyclohexene as an antimicrobial agent.
- the present disclosure provides an antimicrobial composition comprising (Z)-3,7-Dimethyl-2,6-octadien-l-ol and gamma-dodecalactone.
- the present disclosure provides the use of a composition comprising (Z)-3,7- Dimethyl-2,6-octadien-l-ol and gamma-dodecalactone as an antimicrobial agent.
- the present disclosure provides an antimicrobial composition comprising cis-4(Isopropyl)cyclohexanemethanol and 4-Methoxybenzaldehyde.
- the present disclosure provides the use of a composition comprising cis-4(Isopropyl)cyclohexanemethanol and 4-Methoxybenzaldehyde as an antimicrobial agent.
- the present disclosure provides an antimicrobial composition comprising l,3-Benzodioxole-5-carbaldehyde and 4-Methoxybenzaldehyde.
- the present disclosure provides the use of a composition comprising 1,3- Benzodioxole-5-carbaldehyde and 4-Methoxybenzaldehyde as an antimicrobial agent.
- the composition used in the present disclosure comprises nona- 2,6-dien-l-ol in an amount above 25 ppm, alternatively in an amount between 25 ppm and 2000 ppm, alternatively in an amount between 50 ppm and 1500 ppm.
- the composition comprises nona-2,6-dien-l-ol in an amount between 50 ppm and 800 ppm; or in an amount between 200 ppm and 1500 ppm.
- the composition comprises nona- 2,6-dien-l-ol in an amount between 50 ppm and 500 ppm, alternatively in an amount between 50 ppm and 200 ppm.
- the composition comprises 75 ppm, 150 ppm, 300 ppm or 600 ppm of nona-2,6-dien-l-ol.
- composition used in the present disclosure comprises nona-
- the composition comprises at least 25 ppm, alternatively at least 75 ppm of nona-2,6-dien-l-ol and at least 25 ppm, alternatively at least 75 ppm of 3-neopentylpyridine.
- the composition comprises nona-2,6- dien-l-ol in an amount between 25 and 450 ppm, alternatively between 75 and 300 ppm and alternatively between 75 and 150 ppm and 3-neopentylpyridine in an amount between 25 and 450 ppm, alternatively 75 and 300 ppm and alternatively between 75 and 150 ppm.
- the composition comprises nona-2,6-dien-l-ol in an amount between 25 and 250 ppm, alternatively between 50 and 200 ppm and alternatively between 75 and 150 ppm and 3-neopentylpyridine in an amount between 25 and 125 ppm, alternatively between 50 and 100 ppm and alternatively between 65 and 85 ppm; or the composition comprises nona- 2,6-dien-l-ol in an amount between 25 and 125 ppm, alternatively between 50 and 100 ppm and alternatively between 65 and 85 ppm and 3-neopentylpyridine in an amount between 25 and 250 ppm, alternatively between 50 and 200 ppm and alternatively between 75 and 150 ppm.
- the composition comprises (2E,6Z)-nona-2,6-dien-l-ol in an amount between 75 and 150 ppm and 75 ppm of 3-neopentylpyridine; or the composition comprises 75 ppm of (2E,6Z)-nona-2,6-dien-l-ol and 3-neopentylpyridine in an amount between 75 and 150 ppm.
- the composition used in the present disclosure comprises nona-2,6- dien-l-ol and 2-methylhexan-3-one oxime.
- the composition comprises at least 400 ppm, alternatively at least 600 ppm of nona-2,6-dien-l-ol and at least 100 ppm, alternatively at least 150 ppm of methylhexan-3-one oxime; or at least 200 ppm, alternatively at least 300 ppm of nona-2,6-dien-l-ol and at least 700 ppm, alternatively at least 1200 ppm of methylhexan-3-one oxime; or at least 25 ppm, alternatively at least 75 ppm of nona-2,6- dien-l-ol and at least 1800 ppm, alternatively at least 2400 ppm of methylhexan-3-one oxime.
- the composition comprises nona-2,6-dien-l-ol in an amount between 25 and 225 ppm and alternatively between 75 and 150 ppm and 2-methylhexan-3-one oxime in an amount between 1800 and 3600 ppm and alternatively between 2100 and 2700 ppm; or nona-2,6-dien-l-ol in an amount between 400 and 1000 ppm, alternatively between 500 and 800 ppm and alternatively between 550 and 650 ppm and 2-methylhexan-3-one oxime in an amount between 100 and 800 ppm and alternatively between 150 and 600 ppm; or nona-2,6- dien-l-ol in an amount between 200 and 500 ppm, alternatively between 250 and 450 ppm and alternatively between 250 and 350 ppm and 2-methylhexan-3-one oxime in an amount between 700 and 2000 ppm, alternatively between 800 and 1600 ppm, and alternatively between 1000 and 1400 ppm.
- the composition comprises 300 ppm
- the composition used in the present disclosure comprises nona-2,6- dien-l-ol and terpineol.
- the composition comprises at least 200 ppm, alternatively at least 300 ppm of nona-2,6-dien-l-ol and at least 400 ppm, alternatively at least 600 ppm of terpineol; or at least 400 ppm, alternatively at least 600 ppm of nona-2,6- dien-l-ol and at least 200 ppm, alternatively at least 300 ppm of terpineol; or at least 700 ppm, alternatively at least 1200 ppm of nona-2,6-dien-l-ol and at least 25 ppm, alternatively at least 75 ppm of terpineol.
- the composition comprises nona-2,6-dien-l-ol in an amount between 200 and 400 ppm and alternatively between 250 and 350 ppm and terpineol in an amount between 400 and 1000 ppm, alternatively between 500 and 800 ppm and alternatively between 550 and 650 ppm; or nona-2,6-dien-l-ol in an amount between 700 and 2000 ppm, alternatively between 800 and 1600 ppm, and alternatively between 1000 and 1400 ppm and terpineol in an amount between 25 and 250 ppm and alternatively between 75 and 150 ppm; or nona-2,6-dien-l-ol in an amount between 400 and 1000 ppm, alternatively between 500 and 800 ppm and alternatively between 550 and 650 ppm and terpineol in an amount between 200 and 500 ppm, alternatively between 250 and 450 ppm and alternatively between 250 and 350 ppm.
- the composition comprises 600 ppm of nona-2,6-dien-
- the composition used in the present disclosure comprises nona-2,6- dien-l-ol and 2-isopropyl-5-methylphenol.
- the composition comprises at least 25 ppm, alternatively at least 75 ppm of nona-2,6-dien-l-ol and at least 200 ppm, alternatively at least 300 ppm of 2-isopropyl-5-methylphenol; or at least 100 ppm, alternatively at least 150 ppm of nona-2,6-dien-l-ol and at least 100 ppm, alternatively at least 150 ppm of 2-isopropyl-5-methylphenol.
- the composition comprises nona-2,6-dien-l-ol in an amount between 25 and 125 ppm and alternatively between 50 and 100 ppm and 2-isopropyl-5-methylphenol in an amount between 200 and 500 ppm, alternatively between 250 and 450 ppm and alternatively between 250 and 350 ppm; or nona- 2,6-dien-l-ol in an amount between 100 and 400 ppm, alternatively between 150 and 300 ppm and alternatively between 130 and 170 ppm and 2-isopropyl-5-methylphenol in an amount between 100 and 225 ppm and alternatively between 130 and 170 ppm.
- the composition comprises 150 ppm of nona-2,6-dien-l-ol and 150 ppm of 2- isopropyl-5-methylphenol.
- the composition used in the present disclosure comprises gamma- dodecalactone in an amount above 25 ppm, alternatively in an amount between 25 ppm and 2000 ppm, alternatively in an amount between 50 ppm and 1500 ppm.
- the composition comprises gamma-dodecalactone in an amount between 50 ppm and 800 ppm; or in an amount between 200 ppm and 1500 ppm.
- the composition comprises gamma-dodecalactone in an amount between 50 ppm and 500 ppm, alternatively in an amount between 50 ppm and 200 ppm.
- the composition comprises 75 ppm, 150 ppm, 300 ppm, 600 ppm, or 700 ppm of gamma-dodecalactone.
- the composition used in the present disclosure comprises gamma- dodecalactone and l-Methyl-4-(l-methylethenyl)-cyclohexene.
- the composition comprises at least 150 ppm, or, alternatively at least 200 ppm, alternatively at least 250 ppm, alternatively at least 300 ppm, alternatively at least 350 ppm, alternatively at least 400 ppm, alternatively at least 450 ppm, alternatively at least 500 ppm, alternatively at least 550 ppm, alternatively at least 600 ppm, alternatively at least 650 ppm, alternatively at least 700 ppm of gamma-dodecalactone and at least 150 ppm, or, alternatively at least 200 ppm, alternatively at least 250 ppm, alternatively at least 300 ppm, alternatively at least 350 ppm, alternatively at least 400 ppm, alternatively at least 450 ppm, or alternatively at least 500 ppm of
- the composition comprises gamma-dodecalactone in an amount between 200 and 700 ppm, alternatively between 200 and 600 ppm and alternatively between 300 and 600 ppm and l-Methyl-4-(l- methylethenyl)-cyclohexene in an amount between 150 and 500 ppm, alternatively 150 and 500 ppm, alternatively 200 and 400 ppm, alternatively 250 and 400 ppm, and alternatively 300 and 400 ppm.
- the composition comprises gamma-dodecalactone in an amount between 300 and 600 ppm and 300 ppm of l-Methyl-4-(l-methylethenyl)-cyclohexene; or the composition comprises 300 ppm of gamma-dodecalactone and l-Methyl-4-(l- methylethenyl)-cyclohexene in an amount between 200 and 400 ppm.
- the composition comprises 600 ppm of gamma-dodecalactone and l-Methyl-4-(l- methylethenyl)-cyclohexene in an amount between 200 and 400 ppm.
- the composition comprises 300 ppm of gamma-dodecalactone and 300 ppm l-Methyl-4-(l-methylethenyl)-cyclohexene. In some aspects, the composition comprises 600 ppm of gamma-dodecalactone and 300 ppm l-Methyl-4-(l-methylethenyl)- cyclohexene.
- the composition used in the present disclosure comprises gamma- dodecalactone and 4-Methoxybenzaldehyde.
- the composition comprises at least 50 ppm, or alternatively at least 100 ppm, or alternatively at least 150 ppm, or alternatively at least 200 ppm, alternatively at least 250 ppm, alternatively at least 300 ppm, alternatively at least 350 ppm, alternatively at least 400 ppm, alternatively at least 450 ppm, alternatively at least 500 ppm, alternatively at least 550 ppm, alternatively at least 600 ppm, alternatively at least 650 ppm, alternatively at least 700 ppm of gamma-dodecalactone and at least 150 ppm, or, alternatively at least 200 ppm, alternatively at least 250 ppm, alternatively at least 300 ppm, alternatively at least 350 ppm, alternatively at least 400 ppm, alternatively at least 450 ppm, or alternatively at least 500 ppm, or, alternative
- the composition comprises gamma-dodecalactone in an amount between 200 and 700 ppm, alternatively between 200 and 600 ppm and alternatively between 300 and 600 ppm and 4-Methoxybenzaldehyde in an amount between 50 and 500 ppm, alternatively 100 and 500 ppm, alternatively 150 and 400 ppm, alternatively 150 and 350 ppm, and alternatively 150 and 300 ppm.
- the composition comprises gamma-dodecalactone in an amount between 300 and 600 ppm and 150 ppm of 4-Methoxybenzaldehyde; or the composition comprises 300 ppm of gamma-dodecalactone and 4-Methoxybenzaldehyde in an amount between 150 and 300 ppm.
- the composition comprises 600 ppm of gamma- dodecalactone and 4-Methoxybenzaldehyde in an amount between 150 and 300 ppm.
- the composition comprises 300 ppm of gamma-dodecalactone and
- the composition comprises 600 ppm of gamma- dodecalactone and 150 ppm, or alternatively 200 ppm, alternatively 250 ppm, alternatively 300 ppm 4-Methoxybenzaldehyde.
- the composition used in the present disclosure comprises gamma- dodecalactone and l,3-Benzodioxole-5-carbaldehyde.
- the composition comprises at least 150 ppm, or, alternatively at least 200 ppm, alternatively at least 250 ppm, alternatively at least 300 ppm, alternatively at least 350 ppm, alternatively at least 400 ppm, alternatively at least 450 ppm, alternatively at least 500 ppm, alternatively at least 550 ppm, alternatively at least 600 ppm, alternatively at least 650 ppm, alternatively at least 700 ppm of gamma-dodecalactone and at least 150 ppm, or, alternatively at least 200 ppm, alternatively at least 250 ppm, alternatively at least 300 ppm, alternatively at least 350 ppm, alternatively at least 400 ppm, alternatively at least 450 ppm, alternatively at least 500 ppm, alternatively at least 550
- the composition comprises gamma-dodecalactone in an amount between 200 and 700 ppm, alternatively between 200 and 600 ppm and alternatively between 300 and 600 ppm and 1,3- Benzodioxole-5-carbaldehyde in an amount between 150 and 700 ppm, alternatively 150 and 600 ppm, alternatively 200 and 600 ppm, alternatively 250 and 600 ppm, and alternatively 300 and 600 ppm.
- the composition comprises gamma-dodecalactone in an amount between 300 and 600 ppm and 600 ppm of l,3-Benzodioxole-5-carbaldehyde; or the composition comprises 300 ppm of gamma-dodecalactone and l,3-Benzodioxole-5- carbaldehyde in an amount between 300 and 600 ppm.
- the composition comprises 600 ppm of gamma-dodecalactone and l,3-Benzodioxole-5-carbaldehyde in an amount between 300 and 600 ppm.
- the composition comprises 300 ppm of gamma-dodecalactone and 300 ppm l,3-Benzodioxole-5-carbaldehyde. In some aspects, the composition comprises 600 ppm of gamma-dodecalactone and 300 ppm l,3-Benzodioxole-5-carbaldehyde. In some aspects, the composition comprises 300 ppm of gamma-dodecalactone and 600 ppm 1,3- Benzodioxole-5-carbaldehyde. In some aspects, the composition comprises 600 ppm of gamma-dodecalactone and 600 ppm l,3-Benzodioxole-5-carbaldehyde.
- the composition used in the present disclosure comprises (Z)-3,7- Dimethyl-2,6-octadien-l-ol in an amount above 25 ppm, alternatively in an amount between 25 ppm and 2000 ppm, alternatively in an amount between 50 ppm and 1500 ppm.
- the composition comprises (Z)-3,7-Dimethyl-2,6-octadien-l-ol in an amount between 50 ppm and 800 ppm; or in an amount between 200 ppm and 1500 ppm.
- the composition comprises (Z)-3,7-Dimethyl-2,6-octadien-l-ol in an amount between 50 ppm and 500 ppm, alternatively in an amount between 50 ppm and 200 ppm.
- the composition comprises 75 ppm, 150 ppm, 300 ppm, 600 ppm, or 700 ppm of (Z)-3,7-Dimethyl-2,6-octadien-l-ol.
- the composition used in the present disclosure comprises (Z)-3,7- Dimethyl-2,6-octadien-l-ol and gamma-dodecalactone.
- the composition comprises at least 50 ppm, or, alternatively at least 100 ppm, alternatively at least 150 ppm, alternatively at least 200 ppm, alternatively at least 250 ppm, alternatively at least 300 ppm, alternatively at least 350 ppm, or alternatively at least 400 ppm of (Z)-3,7-Dimethyl-2,6- octadien-l-ol and at least 150 ppm, or, alternatively at least 200 ppm, alternatively at least 250 ppm, alternatively at least 300 ppm, alternatively at least 350 ppm, alternatively at least 400 ppm, alternatively at least 450 ppm, or alternatively at least 500 ppm of gamma- dodecalactone.
- the composition comprises (Z)-3,7-Dimethyl-2,6-octadien-l-ol in an amount between 50 and 500 ppm, alternatively between 100 and 500 ppm and alternatively between 1500 and 5000 ppm and gamma-dodecalactone in an amount between 150 and 500 ppm, alternatively 150 and 500 ppm, alternatively 200 and 400 ppm, alternatively 250 and 400 ppm, and alternatively 300 and 400 ppm.
- the composition comprises (Z)-3,7-Dimethyl-2,6-octadien-l-ol in an amount between 150 and 300 ppm and 300 ppm of gamma-dodecalactone; or the composition comprises 150 ppm of (Z)-3,7-Dimethyl-2,6-octadien-l-ol and gamma- dodecalactone in an amount between 200 and 400 ppm.
- the composition comprises 300 ppm of (Z)-3,7-Dimethyl-2,6-octadien-l-ol and gamma-dodecalactone in an amount between 200 and 400 ppm.
- the composition used in the present disclosure comprises cis- 4(Isopropyl)cyclohexanemethanol in an amount above 25 ppm, alternatively in an amount between 25 ppm and 4000 ppm, alternatively in an amount between 50 ppm and 1500 ppm.
- the composition comprises cis-4(Isopropyl)cyclohexanemethanol in an amount between 50 ppm and 800 ppm; or in an amount between 500 ppm and 3000 ppm.
- the composition comprises cis-4(Isopropyl)cyclohexanemethanol in an amount between 300 ppm and 2500 ppm, alternatively in an amount between 600 ppm and 2400 ppm.
- the composition comprises 300 ppm, 400 ppm, 500 ppm, 600 ppm, 700 ppm, 800 ppm, 900 ppm, 1000 ppm, 1100 ppm, 1200 ppm, 1300 ppm, 1400 ppm, 1500 ppm, 1600 ppm, 1700 ppm, 1800 ppm, 1900 ppm, 2000 ppm, 2100 ppm, 2200 ppm, 2300 ppm, or 2400 ppm of cis-4(Isopropyl)cyclohexanemethanol.
- the composition used in the present disclosure comprises cis- 4(Isopropyl)cyclohexanemethanol and 4-Methoxybenzaldehyde.
- the composition comprises at least 300 ppm, 400 ppm, 500 ppm, 600 ppm, 700 ppm, 800 ppm, 900 ppm, 1000 ppm, 1100 ppm, 1200 ppm, 1300 ppm, 1400 ppm, 1500 ppm, 1600 ppm, 1700 ppm, 1800 ppm, 1900 ppm, 2000 ppm, 2100 ppm, 2200 ppm, 2300 ppm, or 2400 ppm of cis-4(Isopropyl)cyclohexanemethanol and at least 150 ppm, or, alternatively at least 200 ppm, alternatively at least 250 ppm, alternatively at least 300 ppm, alternatively at least 350 ppm, alternatively at least 400 ppm, alternatively at least 450
- the composition comprises cis- 4(Isopropyl)cyclohexanemethanol in an amount between 50 and 500 ppm, alternatively between 100 and 500 ppm and alternatively between 1500 and 5000 ppm and 4- Methoxybenzaldehyde in an amount between 150 and 500 ppm, alternatively 150 and 500 ppm, alternatively 200 and 400 ppm, alternatively 250 and 400 ppm, and alternatively 300 and 400 ppm.
- the composition comprises cis-4(Isopropyl)cyclohexanemethanol in an amount between 600 and 2400 ppm and 300 ppm of 4-Methoxybenzaldehyde; or the composition comprises 600 ppm of cis-4(Isopropyl)cyclohexanemethanol and 4- Methoxybenzaldehyde in an amount between 150 and 300 ppm.
- the composition comprises 1200 ppm of cis-4(Isopropyl)cyclohexanemethanol and 4- Methoxybenzaldehyde in an amount between 150 and 300 ppm.
- the composition comprises 2400 ppm of cis-4(Isopropyl)cyclohexanemethanol and 4- Methoxybenzaldehyde in an amount between 150 and 300 ppm.
- the composition used in the present disclosure comprises 1,3- Benzodioxole-5-carbaldehyde in an amount above 25 ppm, alternatively in an amount between 25 ppm and 2000 ppm, alternatively in an amount between 50 ppm and 1500 ppm.
- the composition comprises l,3-Benzodioxole-5-carbaldehyde in an amount between 50 ppm and 800 ppm; or in an amount between 50 ppm and 3000 ppm.
- the composition comprises l,3-Benzodioxole-5-carbaldehyde in an amount between 25 ppm and 600 ppm, alternatively in an amount between 50 ppm and 600 ppm.
- the composition comprises 50 ppm, 60 ppm, 70 ppm, 80 ppm, 90 ppm, 100 ppm, 110 ppm, 120 ppm, 130 ppm, 140 ppm, 150 ppm, 160 ppm, 170 ppm, 180 ppm, 190 ppm, 200 ppm, 250 ppm, or 300 ppm of l,3-Benzodioxole-5-carbaldehyde .
- the composition used in the present disclosure comprises 1,3- Benzodioxole-5-carbaldehyde and 4-Methoxybenzaldehyde.
- the composition comprises at least 50 ppm, or, alternatively at least 100 ppm, alternatively at least 150 ppm, alternatively at least 200 ppm, alternatively at least 250 ppm, alternatively at least 300 ppm, alternatively at least 350 ppm, or alternatively at least 400 ppm of 1,3- Benzodioxole-5-carbaldehyde and at least 150 ppm, or, alternatively at least 200 ppm, alternatively at least 250 ppm, alternatively at least 300 ppm, alternatively at least 350 ppm, alternatively at least 400 ppm, alternatively at least 450 ppm, or alternatively at least 500 ppm of 4-Methoxybenzaldehyde.
- the composition comprises 1,3- Benzodioxole-5-carbaldehyde in an amount between 50 and 500 ppm, alternatively between 75 and 300 ppm and 4-Methoxybenzaldehyde in an amount between 150 and 500 ppm, alternatively 150 and 500 ppm, alternatively 200 and 400 ppm, alternatively 250 and 400 ppm, and alternatively 300 and 400 ppm.
- the composition comprises l,3-Benzodioxole-5-carbaldehyde in an amount between 75 and 300 ppm and 300 ppm of 4-Methoxybenzaldehyde; or the composition comprises 75 ppm of l,3-Benzodioxole-5-carbaldehyde and 4- Methoxybenzaldehyde in an amount between 150 and 300 ppm.
- the composition comprises 300 ppm of l,3-Benzodioxole-5-carbaldehyde and 4- Methoxybenzaldehyde in an amount between 150 and 300 ppm.
- the compositions presented herein demonstrate an antimicrobial effect.
- the compositions even provide a synergistic antimicrobial effect; i.e. an effect which is superior to the simple sum or addition of the antimicrobial effect expected when the two ingredients of the composition would have been admixed in the desired concentration.
- antibacterial activity of the combination of both ingredients is greater than the sum of activities of the individual ingredients.
- the synergistic effect may be determined firstly by measuring the Minimal Inhibitory Concentration (MIC) for each ingredient in isolation and in the combination.
- MIC Minimal Inhibitory Concentration
- FIC Fractional Inhibitory Index
- compositions as defined here-in is particularly advantageous to limit or control the growth of microorganism such as bacteria.
- the antimicrobial effect is one of the main requirements of hygiene products such as body care or home care products.
- compositions as defined above as an antimicrobial agent.
- the present disclosure provides a non-therapeutic method of affecting microbial activity, the method comprising treating a substrate comprising microbes with a composition comprising nona-2,6-dien-l-ol and at least one compound selected from the group consisting of 3-neopentylpyridine, 2-methylhexan-3-one oxime, terpineol and 2- isopropyl-5-methylphenol, wherein the substrate is treated with the composition in an amount sufficient to provide an antimicrobial effect.
- the present disclosure provides a non-therapeutic method of affecting microbial activity, the method comprising treating a substrate comprising microbes with a composition comprising gamma-dodecalactone in combination with at least one ingredient selected from the group consisting of l-Methyl-4-(l-methylethenyl)-cyclohexene, 4-Methoxybenzaldehyde, and l,3-Benzodioxole-5-carbaldehyde, wherein the substrate is treated with the composition in an amount sufficient to provide an antimicrobial effect.
- the present disclosure provides a non-therapeutic method of affecting microbial activity, the method comprising treating a substrate comprising microbes with a composition comprising l,3-Benzodioxole-5-carbaldehyde and gamma- dodecalactone, wherein the substrate is treated with the composition in an amount sufficient to provide an antimicrobial effect.
- the present disclosure provides a non-therapeutic method of affecting microbial activity, the method comprising treating a substrate comprising microbes with a composition comprising l,3-Benzodioxole-5-carbaldehyde and 4-
- Methoxybenzaldehyde wherein the composition is present in an amount sufficient to provide an antimicrobial effect.
- the present disclosure provides a non-therapeutic method of affecting microbial activity, the method comprising treating a substrate comprising microbes with a composition comprising a composition comprising l,3-Benzodioxole-5-carbaldehyde and 4-Methoxybenzaldehyde, wherein the composition is present in an amount sufficient to provide an antimicrobial effect.
- affecting it is meant the inhibition of growth of microorganisms or the killing of microorganisms.
- the present disclosure provides an antimicrobial composition
- an antimicrobial composition comprising nona-2,6-dien-l-ol and at least one compound selected from the group consisting of 3-neopentylpyridine, terpineol, and 2-methylhexan-3-one oxime.
- the present disclosure provides an antimicrobial composition comprising nona-2,6-dien-l-ol and at least one compound selected from the group consisting of 2-isopropyl-5-methylphenol, and 3-neopentylpyridine.
- the present disclosure provides an antimicrobial composition
- an antimicrobial composition comprising gamma-dodecalactone and at least one compound selected from the group consisting of 4-Methoxybenzaldehyde, and l,3-Benzodioxole-5-carbaldehyde.
- the present disclosure provides an antimicrobial composition comprising gamma-dodecalactone and l-Methyl-4-(l-methylethenyl)-cyclohexene.
- the present disclosure provides an antimicrobial composition comprising l,3-Benzodioxole-5-carbaldehyde and gamma-dodecalactone.
- the present disclosure provides an antimicrobial composition comprising l,3-Benzodioxole-5-carbaldehyde and 4-Methoxybenzaldehyde.
- the present disclosure provides an antimicrobial composition comprising l,3-Benzodioxole-5-carbaldehyde and 4-Methoxybenzaldehyde.
- the present disclosure provides a perfuming composition
- a perfuming composition comprising: a) a composition comprising nona-2,6-dien-l-ol and a least one compound selected from the group consisting of 3-neopentylpyridine, 2-methylhexan-3- one oxime, terpineol and 2-isopropyl-5-methylphenol, wherein the composition is present in an amount sufficient to provide an antimicrobial effect; b) at least one ingredient selected from the group consisting of a perfumery carrier, a perfuming co-ingredient and mixtures thereof; and
- the present disclosure provides a perfuming composition
- a perfuming composition comprising: a) a composition comprising at least gamma-dodecalactone in combination with at least one ingredient selected from the group consisting of l-Methyl-4-(l- methylethenyl)-cyclohexene, 4-Methoxybenzaldehyde, and 1,3-Benzodioxole- 5-carbaldehyde, wherein the composition is present in an amount sufficient to provide an antimicrobial effect;
- the present disclosure provides a perfuming composition
- a perfuming composition comprising: a) a composition comprising at least l,3-Benzodioxole-5-carbaldehyde and gamma-dodecalactone, wherein the composition is present in an amount sufficient to provide an antimicrobial effect;
- the present disclosure provides a perfuming composition
- a perfuming composition comprising: a) a composition comprising at least cis-4(Isopropyl)cyclohexanemethanol and 4-Methoxybenzaldehyde, wherein the composition is present in an amount sufficient to provide an antimicrobial effect;
- the present disclosure provides a perfuming composition
- a perfuming composition comprising: a) a composition comprising at least l,3-Benzodioxole-5-carbaldehyde and 4- Methoxybenzaldehyde, wherein the composition is present in an amount sufficient to provide an antimicrobial effect; b) at least one ingredient selected from the group consisting of a perfumery carrier, a perfuming co-ingredient and mixtures thereof; and
- the present disclosure provides a perfuming consumer product comprising a composition comprising nona-2,6-dien-l-ol and a least one compound selected from the group consisting of 3-neopentylpyridine, 2-methylhexan-3-one oxime, terpineol and 2-isopropyl-5-methylphenol, wherein the composition is present in an amount sufficient to provide an antimicrobial effect.
- the present disclosure provides a perfuming consumer product comprising a composition comprising gamma-dodecalactone in combination with at least one ingredient selected from the group consisting of l-Methyl-4-(l-methylethenyl)-cyclohexene, 4-Methoxybenzaldehyde, and l,3-Benzodioxole-5-carbaldehyde, wherein the composition is present in an amount sufficient to provide an antimicrobial effect.
- the present disclosure provides a perfuming consumer product comprising a composition comprising l,3-Benzodioxole-5-carbaldehyde in combination and gamma-dodecalactone, wherein the composition is present in an amount sufficient to provide an antimicrobial effect.
- the present disclosure provides a perfuming consumer product comprising a composition comprising cis-4(Isopropyl)cyclohexanemethanol and 4- Methoxybenzaldehyde, wherein the composition is present in an amount sufficient to provide an antimicrobial effect.
- the present disclosure provides a perfuming consumer product comprising a composition comprising l,3-Benzodioxole-5-carbaldehyde and 4- Methoxybenzaldehyde, wherein the composition is present in an amount sufficient to provide an antimicrobial effect.
- the amounts of each ingredient in the antimicrobial composition are as defined above.
- perfumery carrier we mean here a material which is practically neutral from a perfumery point of view, i.e. which does not significantly alter the organoleptic properties of perfuming ingredients.
- the carrier may be a liquid or a solid.
- liquid carrier one may cite, as non-limiting examples, an emulsifying system, i.e. a solvent and a surfactant system, or a solvent commonly used in perfumery. A detailed description of the nature and type of solvents commonly used in perfumery cannot be exhaustive.
- solvents such as butylene or propylene glycols, glycerol, dipropyleneglycol and its monoether, 1,2,3-propanetriyl triacetate, dimethyl glutarate, dimethyl adipate l,3-diacetyloxypropan-2-yl acetate, diethyl phthalate, isopropyl myristate, benzyl benzoate, benzyl alcohol, 2-(2-ethoxyethoxy)-l- ethano, tri-ethyl citrate or mixtures thereof, which are the most commonly used.
- solvents such as butylene or propylene glycols, glycerol, dipropyleneglycol and its monoether, 1,2,3-propanetriyl triacetate, dimethyl glutarate, dimethyl adipate l,3-diacetyloxypropan-2-yl acetate, diethyl phthalate, isopropyl myristate, benz
- compositions which comprise both a perfumery carrier and a perfumery co-ingredient can be also ethanol, water/ethanol mixtures, limonene or other terpenes, isoparaffins such as those known under the trademark Isopar (origin: Exxon Chemical) or glycol ethers and glycol ether esters such as those known under the trademark Dowanol (origin: Dow Chemical Company), or hydrogenated castors oils such as those known under the trademark Cremophor RH 40 (origin: BASF).
- solid carrier it is meant a material where the perfuming composition or some element of the perfuming composition can be chemically or physically bound. In general such solid carrier are employed either to stabilize the composition, either to control the rate of evaporation of the compositions or of some ingredients.
- solid carrier is of current use in the art and a person skilled in the art knows how to reach the desired effect.
- solid carrier one may cite encapsulating materials.
- examples of such materials may comprise wall-forming and plasticizing materials, such as mono, di- or trisaccharides, natural or modified starches, hydrocolloids, cellulose derivatives, polyvinyl acetates, polyvinylalcohols, proteins or pectins, or yet the materials cited in reference texts such as H. Scherz, Hydrokolloide: Stabilisatoren, Dickungs- und Gelierstoff in Strukturn, Band 2 der committee Strukturchemie, claritat, Behr's Verlag GmbH & Co., Hamburg, 1996.
- the encapsulation is a well-known process to a person skilled in the art, and may be performed, for instance, using techniques such as spray- drying, agglomeration or yet extrusion; or consists of a coating encapsulation, including coacervation and complex coacervation technique.
- resins one may cite the ones produced by the polycondensation of an aldehyde (e.g. formaldehyde, 2,2-dimethoxyethanal, glyoxal, glyoxylic acid or glycolaldehyde and mixtures thereof) with an amine, namely urea, benzoguanamine, glycoluryl, melamine, methylol melamine, methylated methylol melamine, guanazole and the like, as well as mixtures thereof.
- aldehyde e.g. formaldehyde, 2,2-dimethoxyethanal, glyoxal, glyoxylic acid or glycolaldehyde and mixtures thereof
- an amine namely urea, benzoguanamine, glycoluryl, melamine, methylol melamine, methylated methylol melamine, guanazole and the like, as well as mixtures thereof.
- alkylolated polyamines such as those commercially available under the trademark Urac ® (origin: Cytec Technology Corp.), Cymel ® (origin: Cytec Technology Corp.), Urecoll ® or Luracoll ® (origin: BASF).
- a polyol like glycerol
- a polyisocyanate like a trimer of hexamethylene diisocyanate
- a trimer of isophorone diisocyanate or xylylene diisocyanate or a Biuret of hexamethylene diisocyanate or a trimer of xylylene diisocyanate with trimethylolpropane known with the tradename of Takenate ® , origin: Mitsui Chemicals
- Perfuming co-ingredients when present in the perfuming composition, are other than nona-2,6-dien-l-ol, 3-neopentylpyridine, 2-methylhexan-3-one oxime, terpineol or 2- isopropyl-5-methylphenol.
- perfuming co-ingredient it is meant here a compound, which is used in a perfuming preparation or a composition to impart a hedonic effect.
- perfuming co-ingredients do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of his general knowledge and according to intended use or application and the desired organoleptic effect.
- these perfuming co- ingredients belong to chemical classes as varied as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogenous or sulphurous heterocyclic compounds and essential oils, and the perfuming co-ingredients can be of natural or synthetic origin.
- perfuming co-ingredients which are commonly used in perfume formulations, such as:
- Aromatic-herbal ingredients eucalyptus oil, camphor, eucalyptol, menthol and/or alpha- pinene;
- Fruity ingredients gamma ungamma-dodecalactoneactone, 4-decanolide, ethyl 2-methyl- pentanoate, hexyl acetate, ethyl 2-methylbutanoate, gamma nonalactone, allyl heptanoate, 2-phenoxyethyl isobutyrate, ethyl 2-methyl- 1, 3 -dioxolane-2-acetate and/or diethyl 1,4- cyclohexane dicarboxylate;
- Green ingredients 2,4-Dimethyl-3-cyclohexene-l -carbaldehyde, 2-tert-butyl-l-cyclohexyl acetate, styrallyl acetate, allyl (2-methylbutoxy)acetate, 4-methyl-3-decen-5-ol, diphenyl ether, (Z)-3-hexen-l-ol and/or l-(5,5-dimethyl-l-cyclohexen-l-yl)-4-penten-l-one;
- Woody ingredients l-(octahydro-2,3,8,8-tetramethyl-2-naphtalenyl)-l-ethanone, patchouli oil, terpenes fractions of patchouli oil, (rR,E)-2-ethyl-4-(2',2',3'-trimethyl-3'- cyclopenten- l'-yl)-2-buten- 1 -ol, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten- 1 -yl)-2-buten- 1 - ol, Methyl cedryl ketone, 5-(2,2,3-trimethyl-3-cyclopentenyl)-3-methylpentan-2-ol, 1- (2,3, 8, 8-tetramethyl-l, 2,3,4,6,7, 8, 8a-octahydronaphthalen-2-yl)ethan-l-one and/or isobornyl acetate;
- ingredients e.g. amber, powdery spicy or watery: dodecahydro-3a,6,6,9a- tetramethyl-naphtho[2,l-b]furan and any of its stereoisomers, heliotropin, anisic aldehyde, eugenol, cinnamic aldehyde, clove oil, 3-(l,3-benzodioxol-5-yl)-2-methylpropanal and/or 3-(3 -isopropyl- 1 -phenyl)butanal.
- Perfuming co-ingredients may not be limited to the above mentioned, and many other of these co-ingredients are in any case listed in reference texts such as the book by S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA, or its more recent versions, or in other works of a similar nature, as well as in the abundant patent literature in the field of perfumery. It is also understood that the co-ingredients may also be compounds known to release in a controlled manner various types of perfuming compounds.
- perfumery adjuvant is an ingredient capable of imparting additional added benefit such as a color, a particular light resistance, chemical stability, etc.
- viscosity agents e.g. surfactants, thickeners, gelling and/or rheology modifiers
- stabilizing agents e.g. preservatives, antioxidant, heat/light and or buffers or chelating agents, such as BHT
- color agents e.g. dyes and/or pigments
- preservative e.g. antibacterial or antimicrobial or antifungi or anti irritant agents
- abrasives skin cooling agents, fixatives, insect repellants, ointments, vitamins and mixture thereof.
- a perfuming composition consisting of at least one antimicrobial composition as defined above and at least one perfumery carrier represents a particular aspect of the disclosure as well as a perfuming composition comprising at least one antimicrobial composition as defined above, at least one perfumery carrier, at least one perfumery co- ingredient, and optionally at least one perfumery adjuvant.
- any mixture resulting directly from a chemical synthesis e.g. a reaction medium without an adequate purification, in which the compound of the present disclosure would be involved as a starting, intermediate or end- product could not be considered as a perfuming composition according to the disclosure as far as the mixture does not provide the inventive compound in a suitable form for perfumery.
- unpurified reaction mixtures are generally excluded from the present disclosure unless otherwise specified.
- the antimicrobial composition can also be advantageously used in all the fields of modern perfumery, i.e. fine or functional perfumery, to positively impart or modify the odor of a consumer product into which the compound (I) is added. Consequently, another object of the present disclosure is represented by a perfuming consumer product comprising, at least one antimicrobial composition comprising nona-2,6- dien-l-ol and a least a compound selected from the group consisting of 3-neopentylpyridine, 2-methylhexan-3-one oxime, terpineol and 2-isopropyl-5-methylphenol.
- the perfuming consumer product comprises at least one antimicrobial composition comprising nona-2,6-dien-l-ol and a least a compound selected from the group consisting of 3- neopentylpyridine and 2-methylhexan-3-one oxime.
- composition can be added as such or as part of the present disclosure's perfuming composition.
- perfuming consumer product it is meant a consumer product which is expected to deliver at least a pleasant perfuming effect to the surface to which it is applied (e.g. skin, hair, textile, or home surface) or in the air.
- a perfuming consumer product according to the disclosure is a perfumed consumer product which comprises the functional formulation, as well as optionally additional benefit agents, corresponding to the desired consumer product, e.g. a detergent or an air freshener, and an olfactive effective amount of at least one disclosure's compound.
- the perfuming consumer product is a non-edible product.
- Non-limiting examples of suitable perfuming consumer product can be a perfume, such as a fine perfume, a splash or eau de perfume, a cologne or a shave or after-shave lotion; a fabric care product, such as a liquid or solid detergent, a fabric softener, a fabric refresher, an ironing water, a paper, or a bleach, carpet cleaners, curtain-care products; a body-care product, such as a hair care product (e.g. a shampoo, a coloring preparation or a hair spray, a color care product, hair shaping product, a dental care product), a disinfectant, an intimate care product; a cosmetic preparation (e.g.
- a skin cream or lotion e.g. a skin cream or lotion, a vanishing cream or a deodorant or antiperspirant (e.g. a spray or roll on), hair remover, tanning or sun or after sun product, nail products, skin cleansing, a makeup); or a skin-care product (e.g.
- a perfumed soap, shower or bath mousse, oil or gel, or a hygiene product or a foot/hand care products an air care product, such as an air freshener or a "ready to use" powdered air freshener which can be used in the home space (rooms, refrigerators, cupboards, shoes or car) and/or in a public space (halls, hotels, malls, etc.); or a home care product, such as a mold remover, furnisher care, wipe, a dish detergent or hard-surface (e.g. a floor, bath, sanitary or a windows) detergent; a leather care product; a car care product, such as a polish, waxes or a plastic cleaners.
- the consumer products are body care or home care products.
- Some of the above-mentioned perfuming consumer products may represent an aggressive medium for the disclosure's composition, so that it may be necessary to protect the latter from premature decomposition, for example by encapsulation or by chemically binding it to another chemical which is suitable to release the disclosure's ingredient upon a suitable external stimulus, such as an enzyme, light, heat or a change of pH.
- a suitable external stimulus such as an enzyme, light, heat or a change of pH.
- composition according to the disclosure can be incorporated into the various aforementioned products or compositions vary within a wide range of values. These values are dependent on the nature of the article to be perfumed and on the desired organoleptic effect as well as on the nature of the co-ingredients when the compounds according to the disclosure are mixed with perfuming co-ingredients, solvents or additives commonly used in the art.
- concentrations are in the order of 0.001 % to 10 % by weight, or even more, of the disclosure's composition based on the weight of the composition into which they are incorporated. Concentrations lower than these, such as in the order of 0.01% to 1% by weight, can be used when these compounds are incorporated into perfuming consumer products, percentage being relative to the weight of the article.
- the present disclosure provides the use or a method of using a composition comprising nona-2,6-dien-l-ol and at least one compound selected from the group consisting of 3-neopentylpyridine, 2-methylhexan-3-one oxime, terpineol and 2- isopropyl-5-methylphenol, wherein the composition is present in an amount sufficient to provide an antimicrobial effect, for the preparation of an antimicrobially active consumer product.
- the present disclosure provides the use or a method of using a composition comprising gamma-dodecalactone in combination with at least one ingredient selected from the group consisting of l-Methyl-4-(l-methylethenyl)-cyclohexene, 4- Methoxybenzaldehyde, and l,3-Benzodioxole-5-carbaldehyde, wherein the composition is present in an amount sufficient to provide an antimicrobial effect, for the preparation of an antimicrobially active consumer product.
- the present disclosure provides the use or a method of using a composition comprising l,3-Benzodioxole-5-carbaldehyde and gamma-dodecalactone, wherein the composition is present in an amount sufficient to provide an antimicrobial effect, for the preparation of an antimicrobially active consumer product.
- the present disclosure provides the use or a method of using a composition comprising l,3-Benzodioxole-5-carbaldehyde and 4-Methoxybenzaldehyde, wherein the composition is present in an amount sufficient to provide an antimicrobial effect, for the preparation of an antimicrobially active consumer product.
- the present disclosure provides the use or a method of using a composition comprising a composition comprising l,3-Benzodioxole-5-carbaldehyde and 4- Methoxybenzaldehyde, wherein the composition is present in an amount sufficient to provide an antimicrobial effect, for the preparation of an antimicrobially active consumer product.
- an antimicrobially active consumer product it is meant the normal meaning in the art: i.e. a consumer product which is expected to inhibit the growth of microorganism or to kill the microorganism present on the surface to which it is applied (e.g. skin, hair, textile, or home surface).
- the disclosure also provides particular methods of use including counteracting microbial activity in a perfuming or consumer product in particular by circumventing the presence of chlorinated biocides in such products.
- These methods comprise adding to or incorporating in such products a composition selected from the group consisting of: (i) a composition comprising at least nona-2,6-dien-l-ol in combination with at least one ingredient selected from the group consisting of 3-neopentylpyridine, 2-methylhexan-3-one oxime, terpineol and 2-isopropyl-5-methylphenol; (ii) a composition comprising at least gamma-dodecalactone in combination with at least one ingredient selected from the group consisting of l-Methyl-4-(l-methylethenyl)-cyclohexene, 4-Methoxybenzaldehyde, and 1,3- Benzodioxole-5-carbaldehyde; (iii) a composition comprising at least
- Fractional Inhibitory Concentration Index is a measure of activity (Garcia L.S., Clinical Microbiology Procedures Handbook, pg. 140- 162, 3 rd Edition (2010), ASM Press, Washington DC) and is calculated according to the formula below:
- ⁇ FIC Index MIC A combination + MIC B combination
- MIC A alone MIC B alone where (MIC A alone) and (MIC B alone) are the Minimal Inhibitory Concentrations (MIC) of individual ingredients A and B when used in isolation, respectively; whereas (MIC A combination) and (MIC B combination) are the Minimal Inhibitory Concentrations of materials A and B when tested in combination.
- Ingredient A corresponds to nona-2,6-dien-l- ol and ingredient B stands for 3-neopentylpyridine, 2-methylhexan-3-one oxime, terpineol or 2-isopropyl-5-methylphenol.
- the Minimal Inhibitory Concentration of a material is defined as the lowest concentration of an agent which can inhibit visible bacterial growth (CLSI M08-A8 Methods for dilution Antimicrobial Susceptibility Test for Bacteria That Grow Aerobically; Approved Standard-Eighth Edition).
- a combination of raw materials is considered to exert a partially synergistic antimicrobial effect (or also called antimicrobial additive effect) if the FIC Index is inferior to 1 and a synergistic antimicrobial effect if the FIC Index is inferior or equal to 0.5.
- FIC Index values inferior or equal to 4 but superior or equal to 1 indicate indifference, whereas FIC index values superior to 4 indicate antagonism (Garcia L.S., Clinical Microbiology Procedures Handbook, pg. 140- 162, 3 rd Edition (2010), ASM Press, Washington DC).
- Bacterial suspensions of E. coli DSMZ 1103 and S. aureus DSMZ 1104 were prepared as follows: a frozen stock aliquot was streaked on a Tryptic Soy Agar plate, which was then incubated at 37°C for 24 hours. A single bacterial colony was picked and inoculated into 50 ml of Mueller Hinton Broth contained in a 100 ml-flask. Incubation was performed overnight at 37°C, under agitation (160 rpm). The following day, the overnight culture was diluted into 50 ml of fresh Mueller Hinton Broth at 1:50 and 1 :100 for S. aureus and E. coli, respectively.
- Table 1 FIC of a composition comprising (2E,6Z)-nona-2,6-dien-l-ol as ingredient A and 2- isopropyl-5-methylphenol as ingredient B.
- Table 2 FIC of a composition comprising (2E,6Z)-nona-2,6-dien-l-ol as ingredient A and 2- isopropyl-5-methylphenol as ingredient B.
- Table 3 FIC of a composition comprising (2E,6Z)-nona-2,6-dien-l-ol as ingredient A and 3- neopentylpyridine as ingredient B.
- Table 4 FIC of a composition comprising (2E,6Z)-nona-2,6-dien-l-ol as ingredient A and 3- neopentylpyridine as ingredient B.
- Table 5 FIC of a composition comprising gamma-dodecalactone as ingredient A and 1,3-
- Table 6 FIC of a composition comprising gamma-dodecalactone as ingredient A and 4- Methoxybenzaldehyde as ingredient B.
- Table 7 FIC of a composition comprising (Z)-3,7-Dimethyl-2,6-octadien-l-ol as ingredient
- Table 8 FIC of a composition comprising cis-4(Isopropyl)cyclohexanemethanol as ingredient A and 4-Methoxybenzaldehyde as ingredient B.
- Table 9 FIC of a composition comprising (2E,6Z)-nona-2,6-dien-l-ol as ingredient A and 3- neopentylpyridine as ingredient B.
- Table 11 FIC of a composition comprising (2E,6Z)-nona-2,6-dien-l-ol as ingredient 2-methylhexan-3-one oxime as ingredient B.
- Table 12 FIC of a composition comprising (2E,6Z)-nona-2,6-dien-l-ol as ingredient A and
- Table 13 FIC of a composition comprising (2E,6Z)-nona-2,6-dien-l-ol as ingredient OC-terpineol as ingredient B.
- Table 14 FIC of a composition comprising (2E,6Z)-nona-2,6-dien-l-ol as ingredient A and
- Table 15 FIC of a composition comprising gamma-dodecalactone as ingredient A and 4- Methoxybenzaldehyde as ingredient B.
- compositions present an antimicrobial synergistic effect as the FIC of those compositions are below or equal to 1.
- Test samples of base with synergistic binary mixtures were prepared as follows. Raw materials of the synergistic binary mixtures (Table 17) were mixed with the liquid soap base PGK-10-003 (Table 18). Aliquots (2.5 g) of each mixture were weighed into 20 ml glass tube with a stirrer bar, and added with equal amount of MilliQ water to make 50% suspension as the test samples for the BCT test.
- Table 17 Compositions tested.
- BCT tests were performed in the 20 ml sample tubes. Each sample tube with 5 g of 50% sample suspension was placed onto a magnetic stirrer, and an aliquot of bacterial solution (100 ⁇ ) was added to the sample and allowed for a contact of 45 sec during mixing. Then aliquots (0.5 ml) of the mixture were transferred into 5 ml PBS, and further serial dilutions were made in 4.5 ml PBS. Aliquots (0.5 ml) of PBS dilutions were plated onto duplicate plates of TSA plates using the pour plate method. TSA plates were incubated at 37°C for 48 h. After incubation, colonies on TSA plates were enumerated and log reduction of each sample were calculated against the CFU counts of the control sample (MilliQ water).
- Table 19 indicates that binary mixtures of (2E,6Z)-nona-2,6-dien-l-ol: 2-isopropyl-5- methylphenol (1: 1) at 0.5% and 0.6% and (2E,6Z)-nona-2,6-dien-l-ol: 3-neopentylpyridine (1: 1) at 0.5% and 0.6% had 1.1, 1.8,0.6, and 1.4 log reduction against E. coli DSMZ 1103, respectively, in 50% liquid soap base after a contact time of 45 sec.
- Table 19 Antibacterial efficacy of compositions according to some aspects presented herein against E. coli DSMZ 1103 in 50% liquid soap base
- Table 20 shows that binary mixtures of (2E,6Z)-nona-2,6-dien-l-ol: 2-isopropyl-5- methylphenol (2: 1) at 0.3% and 0.45%, (2E,6Z)-nona-2,6-dien-l-ol: 2-methylhexan-3-one oxime (1 :4) at 0.45% and 0.75%, and (2E,6Z)-nona-2,6-dien-l-ol: 3-neopentylpyridine (1: 1) at 0.36% had 1.4 to 3.2 log reduction against S. aureus DSMZ 1104 in 50% liquid soap base after a contact time of 45 sec.
- Table 20 Antibacterial efficacy of compositions according to some aspects presented herein against S. aureus DSMZ 1104 in 50% liquid soap base
- Table 21 showed that the measured bacterial log reduction observed using of mixtures of 0.3% (2E,6Z)-nona-2,6-dien-l-ol + 0.3% 3 -neopentylpyridine is greater than the sum of the measured bacterial log reduction observed either 0.3% (2E,6Z)-nona-2,6-dien-l-ol or 0.3% 3-neopentylpyridine in isolation.
- Table 21 Comparison of the antibacterial efficacy of synergistic binary mixture with that of single materials against E. coli DSMZ 1103 in 50% liquid soap base
- Bacterial solution of C. xerosis ATCC 373 strain was prepared for BCT test as follows. Stock cultures stored at -80°C were subcultured onto Tryptic Soy Agar media with 0.5% Tween 80 (TSA-TW80), and incubated at 37°C for 48 h. The primary cultures were subcultured onto TSA-TW80 again to prepare the secondary cultures. Single colonies of secondary culture were inoculated into 30 ml of Brain Heart Infusion (BHI) broth with 0.5% Tween 80 (BHI-TW80), and incubated at 37°C 180 rpm for 24 h.
- BHI Brain Heart Infusion
- Test samples of base with synergistic binary mixtures were prepared as follows. Raw materials of the synergistic binary mixtures were weighed (Table 22), and mixed with 0.3 g PEG-40 Hydrogenated Castor Oil and 9.57g deodorant roll on base (Table 23).
- BCT tests were performed in 15 ml sample tubes. Aliquots (0.9 g) of each sample were weighed into the tube, and an aliquot of bacterial solution (100 ⁇ ) was added to the sample and allowed for a contact time of 120 sec with constant mixing. At the end of the contact time, aliquots (9 ml) of BHI broth were added to the tube. The suspensions were mixed well by vortexing, and further 1: 10 serial dilutions were made in 9.9 ml BHI. Aliquots (1 ml) of BHI dilutions were plated onto duplicate plates of TSA-TW80 using pour plate methods. TSA-TW80 plates were incubated at 37°C for 2-3 days. After incubation, colonies on TSA-TW80 plates were enumerated and log reduction of each sample were calculated against the CFU counts of the control sample (BHI).
- Table 24 indicates that the addition of binary mixtures of (2E,6Z)-nona-2,6-dien-l- ol: 2-isopropyl-5-methylphenol (1:2) at 0.54%, (2E,6Z)-nona-2,6-dien-l-ol: 2-isopropyl-5- methylphenol (1:1) at 0.432%, (2E,6Z)-nona-2,6-dien-l-ol: 2-methylhexan-3-one oxime (1:4) at 0.54%, (2E,6Z)-nona-2,6-dien-l-ol: Terpineol (1:4) at 0.54%, (2E,6Z)-nona-2,6- dien-l-ol: 3-neopentylpyridine (1: 1) at 0.432% in the 90% deodorant roll-on base improve the antimicrobial effect of base against C. xerosis ATCC 373 after a contact time of 120 sec.
- Table 24 Antibacterial efficacy of synergistic binary mixtures against C. xerosis ATCC 373 in 90% roll-on deodorant base
- Table 25 shows that mixture of (0.216% (2E,6Z)-nona-2,6-dien-l-ol + 0.216% 2- isopropyl-5-methylphenol) had greater log reduction than that of 0.216% (2E,6Z)-nona-2,6- dien-l-ol or 0.216% 2-isopropyl-5-methylphenol.
- a mixture of (0.216% (2E,6Z)- nona-2,6-dien-l-ol + 0.216% 3-neopentylpyridine had similar log reduction as that of 0.216% (2E,6Z)-nona-2,6-dien-l-ol or 0.216% 3-neopentylpyridine.
- Table 25 Comparison of the antibacterial efficacy of synergistic binary mixtures with that of single materials against C. xerosis ATCC 373 in 90% roll-on deodorant base
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Abstract
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CN202210230565.3A CN114794101B (en) | 2016-08-05 | 2017-08-04 | Antimicrobial compositions |
US16/323,070 US11666517B2 (en) | 2016-08-05 | 2017-08-04 | Antimicrobial composition |
ES17745366T ES3021217T3 (en) | 2016-08-05 | 2017-08-04 | Antimicrobial composition comprising nona-2,6-dienol |
BR112019002285A BR112019002285A2 (en) | 2016-08-05 | 2017-08-04 | antimicrobial composition |
IL284723A IL284723B2 (en) | 2016-08-05 | 2017-08-04 | Antimicrobial preparation |
EP25153004.4A EP4541427A3 (en) | 2016-08-05 | 2017-08-04 | Antimicrobial composition |
EP17745366.9A EP3493674B1 (en) | 2016-08-05 | 2017-08-04 | Antimicrobial composition comprising nona-2,6-dienol |
CN201780047414.1A CN110022680B (en) | 2016-08-05 | 2017-08-04 | Antimicrobial composition |
IL264442A IL264442B (en) | 2016-08-05 | 2019-01-23 | Antimicrobial preparation |
JP2022055989A JP7405893B2 (en) | 2016-08-05 | 2022-03-30 | antimicrobial composition |
US18/138,493 US20230310288A1 (en) | 2016-08-05 | 2023-04-24 | Antimicrobial composition |
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JP2021516659A (en) * | 2018-03-20 | 2021-07-08 | フイルメニツヒ ソシエテ アノニムFirmenich Sa | Antibacterial composition |
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