US20190048285A1 - Stimulating agent - Google Patents

Stimulating agent Download PDF

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Publication number
US20190048285A1
US20190048285A1 US16/078,228 US201716078228A US2019048285A1 US 20190048285 A1 US20190048285 A1 US 20190048285A1 US 201716078228 A US201716078228 A US 201716078228A US 2019048285 A1 US2019048285 A1 US 2019048285A1
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Prior art keywords
isopulegol
product
fragrance composition
methyl
fragrance
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Inventor
Jonathan Warr
Johan PONCELET
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Takasago International Corp
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Takasago International Corp
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Assigned to TAKASAGO INTERNATIONAL CORPORATION reassignment TAKASAGO INTERNATIONAL CORPORATION ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: PONCELET, Johan, WARR, JONATHAN
Publication of US20190048285A1 publication Critical patent/US20190048285A1/en
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L9/00—Disinfection, sterilisation or deodorisation of air
    • A61L9/015—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone
    • A61L9/02—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone using substances evaporated in the air by heating or combustion
    • A61L9/03—Apparatus therefor
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L9/00—Disinfection, sterilisation or deodorisation of air
    • A61L9/015—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone
    • A61L9/04—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone using substances evaporated in the air without heating
    • A61L9/042—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone using substances evaporated in the air without heating with the help of a macromolecular compound as a carrier or diluent
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L9/00—Disinfection, sterilisation or deodorisation of air
    • A61L9/015—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone
    • A61L9/04—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone using substances evaporated in the air without heating
    • A61L9/044—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone using substances evaporated in the air without heating with the help of an organic compound other than a macromolecular compound
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L9/00—Disinfection, sterilisation or deodorisation of air
    • A61L9/015—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone
    • A61L9/04—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone using substances evaporated in the air without heating
    • A61L9/048—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone using substances evaporated in the air without heating air treating gels
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L9/00—Disinfection, sterilisation or deodorisation of air
    • A61L9/015—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone
    • A61L9/04—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone using substances evaporated in the air without heating
    • A61L9/12—Apparatus, e.g. holders, therefor
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L9/00—Disinfection, sterilisation or deodorisation of air
    • A61L9/14—Disinfection, sterilisation or deodorisation of air using sprayed or atomised substances including air-liquid contact processes
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/10—General cosmetic use

Definitions

  • the present invention relates to a stimulating agent comprising isopulegol.
  • the invention also relates to a method for imparting a stimulating effect to a consumer product.
  • the invention further relates to a method of giving a stimulative effect to a person by the evaporation and inhalation of a stimulating agent as defined above.
  • EP-A-2 716 303 (PTL 1) describes a psychic energizer agent and composition, the effects of which are assessed by a method called Contingent Negative Variation (CNV). Fragrance materials which have a stimulant effect are also described e.g. in JP-A-63-199293 (PTL 2) and EP-A-1 875 902 (PTL 3), the former application also describes a CNV method of measuring a stimulating effect.
  • CNV is a well-known method of indexing gradual potential changes in human brain, which was first described in 1964 in an article published in Nature.
  • CNV relates to changes of mental processes and arousal levels such as attention, expectation, and anticipation. It is known that when the arousal level is high, an early component of CNV increases compared to normal state and when the arousal level is low, an early component of CNV decreases. For example, it was reported that when subjects smelled a jasmine oil, which is empirically known to have a stimulant effect, an early component of CNV increased whereas when subjects smelled a lavender type fragrance, which is empirically known to have a calming effect, an early component of CNV decreased (see for example Torii et al., 19 th Symposium of Taste and Smell, Sep. 11, 1985 (NPL 1)).
  • An object of the present invention is to provide a method for imparting a stimulating effect to a consumer product.
  • the present invention relates to a method for imparting a stimulating effect to a non-ingestible consumer product, which comprises adding a fragrance composition to said consumer product, wherein the fragrance composition comprises from about 0.2 wt % to less than 10 wt % of isopulegol, based on the total weight of the fragrance composition.
  • the present invention relates to a method of giving a stimulative effect to a person by the evaporation and inhalation of a fragrance composition comprising from about 0.2 wt % to less than 10 wt % of isopulegol, based on the total weight of the fragrance composition.
  • the present invention relates to the (non-therapeutic) use of isopulegol, or of a fragrance composition comprising from about 0.2 wt % to less than 10 wt % of isopulegol, based on the total weight of the fragrance composition, as a stimulating agent.
  • FIG. 1 is a schematic representation of the CNV technique.
  • FIG. 2 represents a typical CNV recording, where potential changes in human brain are detected in the focus area.
  • FIG. 3 represents the difference between the area under the curve of (fragrance A+isopulegol) and the area under the curve of fragrance A alone, as calculated from CNV recording (not shown).
  • FIG. 4 represents the difference between the area under the curve of fragrance B and the area under the curve of air as calculated from CNV recording (shown in FIG. 5 ).
  • FIG. 5 is a CNV recording of Fragrance B (gray line) compared to air (black line).
  • FIG. 6 is a CNV recording of Fragrance C (gray line) compared to air (black line).
  • FIG. 7 represents the difference between the area under the curve of fragrance C and the area under the curve of air as calculated from CNV recording (shown in FIG. 6 ).
  • the area under the curve is calculated for values between the dashed lines in FIGS. 5 and 6 .
  • the present invention relates to a method for imparting a stimulating effect to a household, laundry, personal care, or cosmetic product, which comprises adding a fragrance composition to said product, wherein the fragrance composition comprises from about 0.2 wt % to less than 10 wt % of isopulegol, preferably ( ⁇ ) isopulegol, based on the total weight of the fragrance composition.
  • the term “stimulating effect” refers to an effect uplifting the arousal level of a human subject, as determined by Contingent Negative Variation (CNV).
  • CNV Contingent Negative Variation
  • the terms “stimulating”, “energizing”, “invigorating”, “amusing” and “awakening” may be interchangeably used.
  • the term “stimulating agent” is to be understood in the context of the present invention as an agent providing a stimulating effect.
  • Isopulegol is available either as a racemic mixture (CAS 7786-67-6), or as the ( ⁇ )-isomer (CAS 89-79-2).
  • isopulegol is available as Coolact (registered trademark) P, a product from Takasago.
  • the isopulegol of the invention may have an optical isomer and chemical purity of greater than 90%, preferably greater than 95%, more preferably greater than 97.5%, and even more preferably greater than 99%. Isopulegol purity is determined by gas chromatography using the method described in U.S. Pat. No. 5,773,410 by summing the area percent of impurity peaks and subtracting these from the total measured area which is taken to be 100%.
  • isopulegol Whilst isopulegol is known as a cooling agent that provides a cooling effect to the skin when applied thereto, the inventors have now surprisingly found that isopulegol also produces a stimulating effect, notably when formulated into a fragrance composition that is distributed and then evaporates in the air.
  • isopulegol is present in a fragrance composition.
  • the fragrance composition advantageously comprises from about 0.2 to less than 10 wt %, about 0.2 to about 9 wt %, about 0.2 to about 8 wt %, about 0.2 to about 7 wt %, about 0.2 to about 6 wt %, about 0.2 to about 5 wt %, about 0.2 to about 4 wt % or about 0.2 to about 3 wt % of isopulegol, based on the total weight of the fragrance composition.
  • the fragrance composition may comprise from about 1 to about 9 wt %, about 1 to about 8 wt %, about 1 to about 7 wt %, about 1 to about 6 wt %, about 1 to about 5 wt %, about 1 to about 4 wt % or about 1 to about 3 wt % of isopulegol, based on the total weight of the fragrance composition.
  • the fragrance composition may also comprise from about 2 to about 9 wt %, about 2 to about 8 wt %, about 2 to about 7 wt %, about 2 to about 6 wt %, about 2 to about 5 wt %, or about 2 to about 4 wt % of isopulegol, based on the total weight of the fragrance composition.
  • the fragrance composition does not comprise any of 1-methoxy-propanediol, 1-menthol and p-menthane-3,8-diol. In another embodiment, the fragrance composition does not comprise a diester of the following formula.
  • A represents CH 2 or CH ⁇ CH
  • n represents an integer of 0 to 4 when A is CH 2 or 1 when A is CH ⁇ CH
  • B is an alcohol residue having 10 to 18 carbon atoms and containing a para-menthane skeleton, which may be substituted
  • C is an alcohol residue having 6 to 18 carbon atoms, which may be substituted.
  • the fragrance composition does not comprise a salicylic ester of the following formula.
  • R represents a hydrocarbon group having 1 to 18 carbon atoms which may be substituted.
  • the fragrance composition typically comprises, in addition to isopulegol, a perfume ingredient, and preferably at least two, such as at least five, or at least eight distinct perfume ingredients. It can comprise highly complex mixtures of perfume ingredients, chosen to provide any desired odour.
  • the perfume ingredient typically is an olfactively active material acting as a malodour counteractant, which do not necessarily provide a pleasant smell.
  • Perfume ingredients typically used in the field of perfumery and suitable for the purposes of the present invention are described more fully in S. Arctander, Perfume Flavors and Chemicals 1969, Vols. I and II, Montclair, N.J. and in The Merck Index, 8 th edition, Merck & Co., Inc. Rahway, N.J.
  • perfume ingredient encompasses naturally occurring as well as synthetic perfume materials known for use in perfumes, as well as animal oils.
  • a perfume ingredient can also be any natural oil or extract, or chemical compound used in a fragrance composition. Natural oils and extracts are described in The Essential Oils by E Guenther published in 1949 by Van Nostrand and may include extracts, pressings, collection of exudates, and distillates from any part of suitable plants: roots, rhizomes, bulbs, corms, stem, bark, heartwood, leaves, flowers, seeds and fruit.
  • extracts and distillates examples include citrus fruit oils such as orange, mandarin, grapefruit, lime or lemon oils, tree oils such as pine, or cedarwood, herb oils such as peppermint, thyme, lavender, basil, rosemary, clove or flower extracts such as rose, jasmine, muguet, or geranium oil.
  • each perfume ingredient has a molecular weight greater than 100 g/mol, preferably greater than 120 g/mol and lower than 325 g/mol, preferably lower than 300 g/mol. It may further be preferred that each perfume ingredient has a boiling point in the range 80-400° C., such as in the range 100-350° C., when measured at 760 mm Hg.
  • the perfume ingredient is selected from the following list.
  • C 2 -C 18 hydrocarbons preferably delta-3-carene, alpha-pinene, beta-pinene, alpha-terpinene, gamma-terpinene, p-cymene, bisabolene, camphene, caryophyllene, cedrene, farnesene, limonene, longifolene, myrcene, ocimene, valencene, and (E,Z)-1,3,5-undecatriene.
  • C 2 -C 18 aliphatic alcohols preferably hexanol, octanol, 3-octanol, 2,6-dimethylheptanol, 2-methylheptanol, 2-methyloctanol, (E)-3-hexenol, (E) and (Z)-3-hexenol, 1-octen-3-ol, mixtures of 3,4,5,6,6-pentamethyl-3/4-hepten-2-ol and 3,5,6,6-tetramethyl-4-methyleneheptan-2-ol, (E,Z)-2,6-nonadienol, 3,7-dimethyl-7-methoxyoctan-2-ol, 9-decenol, 10-undecenol, and 4-methyl-3-decen-5-ol.
  • C 2 -C 18 aliphatic aldehydes and their acetals preferably hexanal, heptanal, octanal, nonanal, decanal, undecanal, dodecanal, tridecanal, 2-methyloctanal, 2-methylnonanal, (E)-2-hexenal, (Z)-4-heptenal, 2,6-dimethyl-5-heptenal, 10-undecenal, (E)-4-decenal, 2-dodecenal, 2,6,10-trimethyl-5,9-undecadienal, heptanal diethyl acetal, 1,1-dimethoxy-2,2,5-trimethyl-4-hexene, and citronellyl oxyacetaldehyde.
  • C 3 -C 18 aliphatic ketones and oximes thereof preferably 2-heptanone, 2-octanone, 3-octanone, 2-nonanone, 5-methyl-3-heptanone, 5-methyl-3-heptanone oxime, and 2,4,4,7-tetramethyl-6-octen-3-one.
  • C 2 -C 18 aliphatic sulphur-containing compounds preferably 3-methylthiohexanol, 3-methylthiohexyl acetate, 3-mercaptohexanol, 3-mercaptohexyl acetate, 3-mercaptohexyl butyrate, 3-acetylthiohexyl acetate, and 1-menthene-8-thiol.
  • C 2 -C 18 aliphatic nitrile-containing compounds preferably 2-nonenenitrile, 2-tridecenenenitrile, 2,12-tridecenene-nitrile, 3,7-dimethyl-2,6-octadienenitrile, and 3,7-dimethyl-6-octenenitrile.
  • C 2 -C 18 aliphatic carboxylic acids and esters thereof preferably (E)- and (Z)-3-hexenyl formate, ethyl acetoacetate, isoamyl acetate, hexyl acetate.
  • C 4 -C 18 acyclic terpene alcohols preferably citronellol, geraniol, nerol, linalool, lavandulol, nerolidol, farnesol, tetrahydrolinalool, tetrahydrogeraniol, 2,6-dimethyl-7-octen-2-ol, 2,6-dimethyloctan-2-ol, 2-methyl-6-methylene-7-octen-2-ol, 2,6-dimethyl-5,7-octadien-2-ol, 2,6-dimethyl-3,5-octadien-2-ol, 3,7-dimethyl-4,6-octadien-3-ol, 3,7-dimethyl-1,5,7-octatrien-3-ol, and 2,6-dimethyl-2,5,7-octatrien-1-ol.
  • C 4 -C 18 acyclic terpene aldehydes and ketones preferably geranial, neral, citronellal, 7-hydroxy-3,7-dimethyloctanal, 7-methoxy-3,7-dimethyloctanal, 2,6,10-trimethyl-9-undecenal, geranylacetone, and the dimethyl and diethyl acetals of geranial, neral, and 7-hydroxy-3,7-dimethyloctanal.
  • C 4 -C 18 cyclic terpene alcohols preferably alpha-terpineol, terpineol-4, menthan-8-ol, menthan-1-ol, menthan-7-ol, borneol, isoborneol, linalool oxide, nopol, cedrol, ambrinol, vetiverol, and guaiol.
  • C 4 -C 18 cyclic terpene aldehydes and ketones preferably fenchone, alpha-ionone, beta-ionone, alpha-n-methylionone, beta-n-methylionone, alpha-isomethylionone, beta-isomethylionone, alpha-irone, alpha-damascone, beta-damascone, beta-damascenone, delta-damascone, gamma-damascone, 1-(2,4,4-trimethyl-2-cyclohexen-1-yl)-2-buten-1-one, 1,3,4,6,7,8a-hexahydro-1,1,5,5-tetramethyl-2H-2.4a-methanonaphthalen-8(5H)-one, nootkatone, dihydronootkatone, alpha-sinensal, beta-sinensal, and methyl cedryl ketone.
  • C 4 -C 18 cyclic alcohols preferably 4-tert-butylcyclohexanol, 3,3,5-trimethylcyclohexanol, 3-isocamphylcyclohexanol, 2,6,9-trimethyl-Z2,Z5,E9-cyclododecatrien-1-ol, and 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol.
  • C 4 -C 18 cycloaliphatic alcohols preferably alpha-3,3-trimethylcyclohexylmethanol, 2-methyl-4-(2,2,3-trimethyl-3-cyclopent-1-yl)butanol, 2-methyl-4-(2,2,3-trimethyl-3-cyclopent-1-yl)-2-buten-1-ol, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopent-1-yl)-2-buten-1-ol, 3-methyl-5-(2,2,3-trimethyl-3-cyclopent-1-yl)-pentan-2-ol, 3-methyl-5-(2,2,3-trimethyl-3-cyclopent-1-yl)-4-penten-2-ol, 3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopent-1-yl)-4-penten-2-ol, 1-(2,2,6-trimethylcyclohexyl)pentan-3-ol, and 1-(2,2,6-trimethylcyclohexyl
  • C 4 -C 18 cyclic and cycloaliphatic ethers preferably cedryl methyl ether, cyclododecyl methyl ether, (ethoxymethoxy)cyclododecane, alpha-cedrene epoxide, 3a,6,6,9a-tetramethyl-dodecahydronaphtho[2,1-b]furan, 3a-ethyl-6,6,9a-trimethyldodecahydro-naphtho[2,1-b]furan, 1,5,9-trimethyl-13-oxabicyclo[10.10.0]trideca-4,8-diene, rose oxide, and 2-(2,4-dimethyl-3-cyclohexen-1-yl)-5-methyl-5-(1-methylpropyl)-1,3-dioxane.
  • C 4 -C 18 cyclic ketones preferably 4-tert-butylcyclohexanone, 2,2,5-trimethyl-5-pentylcyclopentanone, 2-heptylcyclopentanone, 2-pentylcyclopentanone, 2-hydroxy-3-methyl-2-cyclopenten-1-one, 3-methyl-cis-2-penten-1-yl-2-cyclopenten-1-one, 3-methyl-2-pentyl-2-cyclopenten-1-one, 3-methyl-4-cyclopentadecenone, 3-methyl-5-cyclopentadecenone, 3-methylcyclopentadecanone, 4-(1-ethoxyvinyl)-3,3,5,5-tetramethylcyclohexanone, 4-tert-pentylcyclohexanone, 5-cyclohexadecen-1-one, 6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone, 9-cycloheptadecen-1-one,
  • C 4 -C 18 cycloaliphatic aldehydes preferably 2,4-dimethyl-3-cyclohexenecarbaldehyde, 2-methyl-4-(2,2,6-trimethyl-cyclohexen-1-yl)-2-butenal, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenecarbaldehyde, and 4-(4-methyl-3-penten-1-yl)-3-cyclohexenecarbaldehyde.
  • C 4 -C 18 cycloaliphatic ketones preferably 1-(3,3-dimethylcyclohexyl)-4-penten-1-one, 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one, 2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydro-2-naphthalenyl methyl ketone, methyl-2,6,10-trimethyl-2,5,9-cyclododecatrienyl ketone, and tert-butyl(2,4-dimethyl-3-cyclohexen-1-yl)ketone.
  • Esters of cyclic alcohols in C 4 -C 18 preferably 2-tert-butylcyclohexyl acetate, 4-tert-butyl-cyclohexyl acetate, 2-tert-pentylcyclohexyl acetate, 4-tert-pentylcyclohexyl acetate, decahydro-2-naphthyl acetate, 3-pentyltetrahydro-2H-pyran-4-yl acetate, decahydro-2,5,5,8a-tetramethyl-2-naphthyl acetate, 4,7-methano-3a,4,5,6,7,7a-hexahydro-5 or 6-indenyl acetate, 4,7-methano-3a,4,5,6,7,7a-hexahydro-5 or 6-indenyl propionate, 4,7-methano-3a,4,5,6,7,7a-hexahydro-5 or 6-indenyl iso
  • Esters of cycloaliphatic carboxylic acids in C 4 -C 18 preferably allyl 3-cyclohexylpropionate, allyl cyclohexyloxyacetate, methyl dihydrojasmonate, methyl jasmonate, methyl 2-hexyl-3-oxocyclopentanecarboxylate, ethyl 2-ethyl-6,6-dimethyl-2-cyclohexenecarboxylate, ethyl 2,3,6,6-tetramethyl-2-cyclohexenecarboxylate, and ethyl 2-methyl-1,3-dioxolane-2-acetate.
  • C 4 -C 18 aromatic hydrocarbons preferably styrene and diphenylmethane.
  • C 4 -C 18 araliphatic alcohols preferably benzyl alcohol, 1-phenylethyl alcohol, 2-phenylethyl alcohol, 3-phenylpropanol, 2-phenylpropanol, 2-phenoxyethanol, 2,2-dimethyl-3-phenylpropanol, 2,2-dimethyl-3-(3-methylphenyl)propanol, 1,1-dimethyl-2-phenylethyl alcohol, 1,1-dimethyl-3-phenylpropanol, 1-ethyl-1-methyl-3-phenylpropanol, 2-methyl-5-phenylpentanol, 3-methyl-5-phenylpentanol, 3-phenyl-2-propen-1-ol, 4-methoxybenzyl alcohol, and 1-(4-isopropylphenyl)ethanol.
  • Esters of araliphatic alcohols in C 4 -C 18 and aliphatic carboxylic acids in C 4 -C 18 preferably benzyl acetate, benzyl propionate, benzyl isobutyrate, benzyl isovalerate, 2-phenylethyl acetate, 2-phenylethyl propionate, 2-phenylethyl isobutyrate, 2-phenylethyl isovalerate, 1-phenylethyl acetate, alpha-trichloromethylbenzyl acetate, alpha,alpha-dimethylphenylethyl acetate, alpha,alpha-dimethylphenylethyl butyrate, cinnamyl acetate, 2-phenoxyethyl isobutyrate, and 4-methoxybenzyl acetate.
  • C 2 -C 18 araliphatic ethers preferably 2-phenylethyl methyl ether, 2-phenylethyl isoamyl ether, 2-phenylethyl 1-ethoxyethyl ether, phenylacetaldehyde dimethyl acetal, phenylacetaldehyde diethyl acetal, hydratropaldehyde dimethyl acetal, phenylacetaldehyde glycerol acetal, 2,4,6-trimethyl-4-phenyl-1,3-dioxane, 4,4a,5,9b-tetrahydroindeno[1,2-d]-m-dioxin, and 4.4a,5,9b-tetrahydro-2,4-dimethylindeno[1,2-d]-m-dioxin.
  • C 4 -C 18 aromatic and araliphatic aldehydes preferably benzaldehyde, phenylacetaldehyde, 3-phenylpropanal, hydratropaldehyde, 4-methylbenzaldehyde, 4-methylphenylacetaldehyde, 3-(4-ethylphenyl)-2,2-dimethylpropanal, 2-methyl-3-(4-isopropylphenyl)propanal, 2-methyl-3-(4-tert-butylphenyl)propanal, 3-(4-tert-butylphenyl)propanal, cinnamaldehyde, alpha-butylcinnamaldehyde, alpha-amylcinnamaldehyde, alpha-hexylcinnamaldehyde, 3-methyl-5-phenylpentanal, 4-methoxybenzaldehyde, 4-hydroxy-3-methoxybenzaldehyde, 4-hydroxy-3-e
  • C 4 -C 18 aromatic and araliphatic ketones preferably acetophenone, 4-methylacetophenone, 4-methoxyacetophenone, 4-tert-butyl-2,6-dimethylacetophenone, 4-phenyl-2-butanone, 4-(4-hydroxyphenyl)-2-butanone, 1-(2-naphthalenyl)ethanone, benzophenone, 1,1,2,3,3,6-hexamethyl-5-indanyl methyl ketone, 6-tert-butyl-1,1-dimethyl-4-indanyl methyl ketone, 1-[2,3-dihydro-1,1,2,6-tetramethyl-3-(1-methylethyl)-1H-5-indenyl]ethanone, and 5′,6′,7′,8′-tetrahydro-3′,5′,5′,6′,8′,8′-hexamethyl-2-acetonaphthone.
  • C 4 -C 18 aromatic and araliphatic carboxylic acids and esters thereof preferably phenylacetic acid, methyl benzoate, ethyl benzoate, hexyl benzoate, benzyl benzoate, methyl phenylacetate, ethyl phenylacetate, geranyl phenylacetate, phenylethyl phenylacetate, methyl cinnamate, ethyl cinnamate, benzyl cinnamate, phenylethyl cinnamate, cinnamyl cinnamate, allyl phenoxyacetate, methyl salicylate, isoamyl salicylate, hexyl salicylate, cyclohexyl salicylate, cis-3-hexenyl salicylate, benzyl salicylate, phenylethyl salicylate, methyl 2,4-dihydroxy-3,6-dimethylbenzoate,
  • Nitrogen-containing aromatic compounds in C 4 -C 18 preferably 2,4,6-trinitro-1,3-dimethyl-5-tert-butylbenzene, 3,5-dinitro-2,6-dimethyl-4-tert-butylacetophenone, cinnamonitrile, 5-phenyl-3-methyl-2-pentenenitrile, 5-phenyl-3-methylpentanenitrile, methyl anthranilate, methyl N-methylanthranilate, Schiff bases of methyl anthranilate with 7-hydroxy-3,7-dimethyloctanal, 2-methyl-3-(4-tert-butylphenyl)propanal, 2,4-dimethyl-3-cyclohexene-carbaldehyde, 6-isopropylquinoline, 6-isobutylquinoline, 6-sec-butylquinoline, indole, skatole, 2-methoxy-3-isopropylpyrazine, and 2-isobutyl-3-methoxypyra
  • Phenols, phenyl ethers and phenyl esters preferably estragole, anethole, eugenol, eugenyl methyl ether, isoeugenol, isoeugenyl methyl ether, thymol, carvacrol, diphenyl ether, beta-naphthyl methyl ether, beta-naphthyl ethyl ether, beta-naphthyl isobutyl ether, 1,4-dimethoxybenzene, eugenyl acetate, 2-methoxy-4-methylphenol, 2-ethoxy-5-(1-propenyl)phenol, and p-cresyl phenylacetate.
  • Heterocyclic compounds in C 4 -C 12 preferably 2,5-dimethyl-4-hydroxy-2H-furan-3-one, 2-ethyl-4-hydroxy-5-methyl-2H-furan-3-one, 3-hydroxy-2-methyl-4H-pyran-4-one, and 2-ethyl-3-hydroxy-4H-pyran-4-one.
  • Lactones in C 4 -C 18 preferably 1,4-octanolide, 3-methyl-1,4-octanolide, 1,4-nonanolide, 1,4-decanolide, 8-decen-1,4-olide, 1,4-undecanolide, 1,4-dodecanolide, 1,5-decanolide, 1,5-dodecanolide, 1,15-pentadecanolide, cis and trans-11-pentadecen-1,15-olide, cis- and trans-12-pentadecen-1,15-olide, 1,16-hexadecanolide, 9-hexadecen-1,16-olide, 10-oxa-1,16-hexadecanolide, 11-oxa-1,16-hexadecanolide, 12-oxa-1,16-hexadecanolide, ethylene 1,12-dodecanedioate, ethylene 1,13-tridecanedio
  • the perfume ingredient present in the fragrance composition preferably does not contain ionizing functional groups, such as sulfonates, sulphates, phosphates or quaternary ammonium ions.
  • the fragrance composition of the invention may include one or more support materials, such as solvents or UV stabilizers.
  • suitable solvents include hydrocarbons such as those sold under the trade name Isopar (registered trademark); ethers such as those sold under the Dowanol (registered trademark) trade name: benzyl benzoate; isopropyl myristate; dialkyl adipates; dialkyl succinates; dialkyl glutarates such as the dimethyl esters sold under the trade name Flexisolv (registered trademark); citrate esters, such as triethyl citrate and acetyl tributyl citrate; soybean methyl ester such as ME-S 1885 (sold by Peter Cremer NA); diethyl phthalate; diethylene glycol monoethyl ether, 3-methoxy-3-methyl-1-butanol; dipropylene glycol; and iso-propylidene glycerol sold under the Augeo (registered trademark) Clean Multi brand name
  • UV stabilisers examples include butyl methoxy dibenzoyl methane; bis ethyl-hexyloxyphenolmethoxyphenyl triazine; those sold under the Uvinol (registered trademark) trade name such as Uvinul D50 [bis(2,4-dihydroxyphenyl)-methanone], Uvinul MC80 (ethylhexyl methoxycinnamate) and Uvinul M40 (benzophenone-3); those sold under the Parsol (registered trademark) trade name, such as Parsol (registered trademark) MCX (same product as Uvinul MC80) and Parsol (registered trademark) 1789 (butyl methoxydibenzoylmethane); and those sold under the Tinogard (registered trademark) trade name, such as Tinogard (registered trademark) TT (pentaerythrityl tetra di-t-butyl hydroxyhydrocinnamate).
  • fragrances compositions of the present invention impart a stimulating effect to non-ingestible consumer products into which they are incorporated.
  • a non ingestible consumer product means a product or device for domestic use generally in the form in which it is sold but which excludes products which may be ingested either those which are deliberately ingested such as foodstuffs, snacks and pharmaceutical products and also those which may be accidentally ingested because they are used in the mouth such as toothpastes and mouthwashes.
  • Such non ingestible consumer products include but are not limited to products for and/or methods relating to cleaning or treating hair, including bleaching, colouring, conditioning, shampooing, and styling products; products for cleaning or treating skin including bar soaps, liquid soaps, wet wipes, shower gels, bath foams, body washes, make up removers and exfoliating products, topically applied skin treatment products such as deodorants and antiperspirants, moisturizing creams, lotions, colour cosmetics, depillatory products, talcum powders, body sprays, eau de toilette and other fine fragrances; shaving products such as shaving gels, shaving foams and after shave balms, products for and/or methods relating to cleaning garments, soft furnishings, dishwashing, hard surfaces and any other surfaces in the home and domestic environment such as motor vehicle interiors, including: air care including air fresheners and scent delivery systems, car care products, hand and machine dishwashing products, fabric conditioning products including fabric softeners and/or fragrancing products, laundry detergent products and tumble drier additive
  • the non-ingestible consumer product is selected from household products, laundry products, personal care products and cosmetic products.
  • Non-limiting examples of household products include air freshener dispenser devices, floor cleaners, kitchen or bathroom surface cleaners, and solid or liquid toilet rim blocks.
  • the air freshener dispenser device can be:
  • the household product of the invention is a kitchen or bathroom surface cleaner or a floor cleaner.
  • Floor cleaners also known as general purpose cleaner, also include carpet cleaner. They may be in several forms: isotropic liquids, thickened liquids with or without abrasive, pastes, gels, foams or sprays. They can be used directly from the bottle or after dilution in water.
  • Various delivery methods have been devised for the convenience of the users, some are sprayed onto surfaces from trigger spray bottles, or alternatively they can be poured directly onto surfaces. They may contain additional ingredients such as acids for limescale removal, biocides for hygiene, or bleaching agents.
  • a standard floor cleaner composition is given in Table 1 below, which summarises the main ingredients and their quantities (taken from Surfactant Science Series Vol. 67 Liquid Detergents chapter on Specialty Liquid Household Surface Cleaners p. 479, Table 4).
  • Solid toilet rim blocks are intended to be located under the rim of a lavatory bowl or urinal such that, during a flushing cycle, water from the cistern flows over the block thereby dissolving a portion of the toilet rim block.
  • the invention also relates to cageless rim blocks which adhere directly to the surface of the lavatory pan, and to solid toilet cistern blocks which are placed in the cistern and dissolve slowly in the water contained therein. It will be appreciated that the solubility characteristics of these two products are quite different, since one is constantly under water while the other has intermittent short term contact with water. However, they both contain a surfactant, fillers, and a fragrance composition as defined according to the invention, and optionally bleaching agents, germicides and anti-limescale agents. Typical formulations are described in EP 0 462 643, GB 2 178 442, U.S. Pat. No. 4,874,536 and U.S. Pat. No. 8,658,588, which are incorporated herein by reference.
  • the liquid toilet rim blocks are devices that dispense liquid compositions directly into a lavatory bowl from under the rim of said bowl. Such liquid toilet rim blocks are usually attached by various means, such as hooks and the like, to the rim of the lavatory bowl. Every time a toilet equipped with a liquid toilet rim block is flushed, an amount of composition is dispensed into the lavatory bowl. Examples of liquid toilet rim blocks are given in WO 02/40792, EP 0 775 741, WO 01/94520 and US 2008/086801, which are incorporated herein by reference.
  • Personal care products may include products that can be applied to the skin, hair and nails either as leave on or rinse off product.
  • Non-limiting examples of personal care products include shaving aids, shampoos, hair-conditioner products, leave-on-skin-care products, skin cleansing or washing products (such as a rinse-off skin cleansing or washing product), moist tissues, body sprays, deodorants or antiperspirants, eau de toilette and other fine fragrances.
  • the personal care product is an eau de toilette or a fine fragrance.
  • Shaving aids specifically include foams, gels, creams and bars (reference can be made for example to U.S. Pat. No. 7,069,658, U.S. Pat. No. 6,944,952, U.S. Pat. No. 6,594,904, U.S. Pat. No. 6,182,365. U.S. Pat. No. 6,185,822, U.S. Pat. No. 6,298,558 and U.S. Pat. No. 5,113,585).
  • Shampoos and hair conditioners specifically include two-in-one shampoos and shampoos especially formulated for dry or greasy hair or containing additives such as antidandruff agents. Hair conditioners may be rinse off or leave on hair conditioners also included are hair tonics, bleaches colorants, setting and styling products.
  • hair conditioners may be rinse off or leave on hair conditioners also included are hair tonics, bleaches colorants, setting and styling products.
  • Leave-on-skin-care products comprise skin washing products, moist tissues, body sprays, deodorants and antiperspirants.
  • Skin washing products specifically include beauty and hygiene bar soaps, shower gels, liquid soaps, body washes, exfoliating gels and pastes (reference can be made for example to U.S. Pat. No. 3,697,644; U.S. Pat. No. 4,065,398; U.S. Pat. No. 4,387,040).
  • Moist tissues specifically include skin cleansing wipes, baby wipes, make-up removal wipes and skin refreshing wipes (reference can be made for example to U.S. Pat. No. 4,775,582; WO02/07701; WO2007/069214 and WO95/16474).
  • Body sprays, deodorants and antiperspirants specifically include sticks, liquid roll-on applicators and pressurized sprays.
  • Eau de toilette formulations typically comprise (% by weight) from about 75% to about 80% ethanol, about 10% fragrance, less than about 1% UV filter, optionally less than about 1% colourants, optionally less than about 1% metal sequestrant, the balance to 100% being water.
  • Non-limiting examples of laundry products include powdered and liquid laundry detergents, detergent tablets and bars, and fabric softeners.
  • the laundry product is a fabric softener, a fabric conditioner or a laundry detergent.
  • Fabric softeners and conditioners specifically include both conventional diluted (e.g. 2% to 8% by weight) liquid active concentration softeners and concentrated (e.g. 10% to 40% by weight) liquid active concentration softeners as well as fabric conditioners which may contain ingredients to protect colors or garment shape and appearance (reference can be made for 30 example to U.S. Pat. No. 6,335,315, U.S. Pat. No. 5,674,832, U.S. Pat. No. 5,759,990. U.S. Pat. No. 5,877,145, U.S. Pat. No. 5,574,179).
  • Laundry detergents particularly liquid laundry detergents, specifically include light duty liquid detergents and heavy duty liquid detergents which may be structured multi-phase liquids or isotropic liquids and which may be aqueous or non-aqueous liquids. These liquids may be in 35 bottles or unit dose sachets and they may optionally contain bleaching agents or enzymes (reference can be made for example to U.S. Pat. No. 5,929,022, U.S. Pat. No. 5,916,862, U.S. Pat. No. 5,731,278, U.S. Pat. No. 5,470,507, U.S. Pat. No. 5,466,802, U.S. Pat. No. 5,460,752, and U.S. Pat. No. 5,458,810).
  • the present invention relates to a method of giving a stimulating effect to a person by the evaporation and inhalation of a fragrance composition
  • a fragrance composition comprising from about 0.2 wt % to less than 10 wt % of isopulegol, preferably ( ⁇ ) isopulegol, based on the total weight of the fragrance composition.
  • the present invention relates to the (non-therapeutic) use of isopulegol, or of a fragrance composition comprising from about 0.2 wt % to less than 10 wt % of isopulegol, based on the total weight of the fragrance composition, as a stimulating agent.
  • the isopulegol is preferably ( ⁇ ) isopulegol.
  • the stimulating effect of isopulegol was determined by the CNV (Contingent Negative Variation) method as described below and briefly summarized in FIGS. 1 and
  • the CNV was measured using a digital electroencephalograph BIOSEMi (registered trademark). Electrodes for the CNV measurement were placed at Fp1, Fp2, F4, Fz, F3, T7, C3, Cz, C4, T8, P4, Pz, P3, O1, Oz, O2 according to the international 10-20 system, electrodes for ear lobes were set to indifferent electrodes, and brain waves were recorded at a time constant of 5.0 seconds referenced to the linked earlobes. In order to check artifacts of eye movement to a brain wave, vertical and horizontal movements of the left eye were also recorded.
  • BIOSEMi registered trademark
  • the evaluation of the CNV waveform was conducted according to the method of Torii et al. (op. cit.), in which CNV was evaluated by the area (unit: ms ⁇ mH) of an early component between 400 ms to 1.000 ms after the warning sound stimulus (S1).
  • a fragrance composition having the following composition shown in Table 2 was prepared.
  • fragrance A to which 2 wt % isopulegol was added, was determined by the CNV method as described above, using a panel of 7 subjects. Fragrance A was used as a control. It can be seen from FIG. 3 that isopulegol enhances the CNV activity of fragrance A; this enhancement is characteristic of a stimulating effect imparted by the inclusion of isopulegol.
  • a fragrance composition having the following composition shown in Table 3 was prepared.
  • fragrance B was determined by the CNV method as described above, using a panel of 17 subjects. Air was used as a control. It can be seen from FIG. 4 that the CNV activity of fragrance B is significantly greater than that of air (mean ratio of +21%; t-test p ⁇ 0.05). This effect is characteristic of a stimulating effect imparted by the inclusion of isopulegol.
  • a fragrance composition having the following composition shown in Table 4 was prepared.
  • fragrance C was determined by the CNV method as described above, using a panel of 8 subjects. It can be seen from FIG. 7 that the CNV activity of fragrance C is significantly greater than that of air (mean ratio+31.9%). This effect is characteristic of a stimulating effect imparted by the inclusion of isopulegol.
  • Eau de Toilette formulation can be used in the context of the invention (amounts are in percent by weight).

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