Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
  • C07C49/29—Saturated compounds containing keto groups bound to rings
  • C07C49/297—Saturated compounds containing keto groups bound to rings to a five-membered ring
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
  • C07C31/13—Monohydroxylic alcohols containing saturated rings
  • C07C31/133—Monohydroxylic alcohols containing saturated rings monocyclic
  • C07C31/135—Monohydroxylic alcohols containing saturated rings monocyclic with a five or six-membered rings; Naphthenic alcohols
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
  • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
• • 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
  • C11B9/003—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing less than six carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C2601/00—Systems containing only non-condensed rings
  • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
  • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated

Definitions

• the present invention relates to 3-isopropyl-1-methylcyclopentyl derivatives, namely (3- isopropyl-1-methylcyclopentyl)ethanol, (3-isopropyl-1-methylcyclopentyi)ethanone and (3-isopropyl-1-methylcyclopentyl)methanol and their use as fragrances.
• This invention relates furthermore to a method for their production and to fragrance compositions comprising them.
• the present invention refers in one of its aspects to the use of a compound of formula la and the enantiomer, namely ⁇ " ⁇ S,3R)- enantiomer, thereof as fragrance
• R 1 is hydrogen or methyl;
• R 2 is hydrogen; and
• R 3 is hydroxyl; or
• R 2 and R 3 form together with the carbon atom to which they are attached a carbonyl group.
• enriched is used herein to describe a compound having an enantiomeric purity greater than 1 :1 in favour of the selected enantiomer.
• Compounds are preferred having a purity of about 1 :3 or greater, e.g. 1 :4.
• Particularly preferred are compounds having an enantiomeric purity of 1 :9 or greater, such as 5:95 or 1 :99.
• Particularly preferred compounds of the present invention are [(1f?,3S)-3-isopropyl-1- methylcyclopentyl]methanol, 1-[(1f?,3S)-3-isopropyl-1-methylcyclopentyl]ethanone, and 1 -[(1 f?,3S)-3-isopropyl-1 -methylcyclopentyl]ethanol.
• the compounds according to the present invention may be used alone or in combination with a base material.
• the "base material” includes all known odourant molecules selected from the extensive range of natural products and synthetic molecules currently available, such as essential oils, alcohols, aldehydes and ketones, ethers and acetals, esters and lactones, macrocycles and heterocycles, and/or in admixture with one or more ingredients or excipients conventionally used in conjunction with odourants in fragrance compositions, for example, carrier materials, and other auxiliary agents commonly used in the art.
• oils and extracts e.g. tree moss absolute, basil oil, castoreum, costus root oil, myrtle oil, oak moss absolute, geranium oil, jasmin absolute, patchouli oil, rose oil, sandalwood oil, wormwood oil, lavender oil or ylang-ylang oil;
• aldehydes and ketones e.g. ⁇ -amylcinnamaldehyde, Georgywood T I MM hydroxycitronellal, Iso E Super, Isoraldeine , Hedione , maltol, Methyl cedryl ketone, methylionone or vanillin;
• ethers and acetals e.g. AmbroxTM, geranyl methyl ether, rose oxide or SpirambreneTM.
• esters and lactones e.g. benzyl acetate, Cedryl acetate, ⁇ -decalactone, Helvetolide ® , ⁇ -undecalactone or Vetivenyl acetate.
• heterocycles e.g. isobutylchinoline.
• the compounds of the present invention may be used in a broad range of fragrance applications, e.g. in any field of fine and functional perfumery, such as perfumes, household products, laundry products, body care products and cosmetics.
• the compounds can be employed in widely varying amounts, depending upon the specific application and on the nature and quantity of other odourant ingredients.
• the proportion is typically from O.001 to 20 weight percent of the application.
• compounds of the present invention may be employed in a fabric softener in an amount of from 0.001 to O.05 weight percent.
• compounds of the present invention may be used in fine perfumery in amounts of from 0.1 to 20 weight percent, more preferably between 0.1 and 5 weight percent.
• these values are given only by way of example, since the experienced perfumer may also achieve effects or may create novel accords with lower or higher concentrations.
• the compounds of the present invention may be employed into the fragrance application simply by directly mixing the fragrance composition with the fragrance application, or they may, in an earlier step be entrapped with an entrapment material, for example, polymers, capsules, microcapsules and nanocapsules, liposomes, film formers, absorbents such as carbon or zeolites, cyclic oligosaccharides and mixtures thereof, or they may be chemically bonded to substrates, which are adapted to release the fragrance molecule upon application of an external stimulus such as light, enzyme, or the like, and then mixed with the application.
• an entrapment material for example, polymers, capsules, microcapsules and nanocapsules, liposomes, film formers, absorbents such as carbon or zeolites, cyclic oligosaccharides and mixtures thereof, or they may be chemically bonded to substrates, which are adapted to release the fragrance molecule upon application of an external stimulus such as light, enzyme, or the like, and then mixed with the application.
• the invention additionally provides a method of manufacturing a fragrance application, comprising the incorporation of a compound of formula I enriched in one of their enantiomers, as a fragrance ingredient, either by directly admixing the compound to the application or by admixing a fragrance composition comprising a compound of formula I enriched in one of their enantiomers, which may then be mixed to a fragrance application, using conventional techniques and methods.
• fragment application means any product, such as fine perfumery, e.g. perfume and eau de toilette; household products, e.g. detergents for dishwasher, surface cleaner; laundry products, e.g. softener, bleach, detergent; body care products, e.g. shampoo, shower gel; and cosmetics, e.g. deodorant, vanishing creme, comprising an odourant.
• household products e.g. detergents for dishwasher, surface cleaner
• laundry products e.g. softener, bleach, detergent
• body care products e.g. shampoo, shower gel
• cosmetics e.g. deodorant, vanishing creme
• (3-lsopropyl-1-methylcyclopentyl)methanol may be prepared by reduction of 3- isopropyl-1-methylcyclopentanecarboxylic acid (A), which has been prepared by rearrangement of fenchone, in the presence of LAH to the corresponding alcohol, as shown in scheme 1.
• Scheme 1 3- isopropyl-1-methylcyclopentanecarboxylic acid (A), which has been prepared by rearrangement of fenchone, in the presence of LAH to the corresponding alcohol, as shown in scheme 1.
• Optically pure compounds of formula la and lb and enantiomeric mixtures of a compound of formula l enriched in one of the enantiomers may be synthesised, starting from optically pure fenchone or an enantiomeric mixture enriched in either (1f?)-(-)-fenchone or (1 S)-(+)-fenchone.
• Example 1 f(1r?,3S)-3-lsopropyl-1-methylcyclopentvnmethanol
• (1 ,3S)-3-lsopropyl-1-methylcyclopentanecarboxylic acid 70.0 g, 0.41 mol
• (1R)-(-)-fenchone V. Braun, J.; Jacob, A. Chem. Ber. 1933, 66, 1461
• diethyl ether 100 ml
• Odour description floral, green, jasmine, lily-of-the-valley, fresh, clean.
• Odour description floral, fruity, green, rosy, hesperidic (grapefruit).
• Example 3 1-[(1R,3S )-3-lsopropyl-1-methylcvclopentv ⁇ ethanone A 1.6M solution of methyllithium in diethyl ether (200 ml, 0.32 mol) was added dropwise during 25 min. into a solution of (1R,3S)-3-lsopropyl-1-methylcyclopentanecarboxylic acid (25.5 g, 0.15 rnol) in THF (250 ml) at 0°C.
• chlorotrimethylsilane 151 ml, 1.2 mol was added with cooling and the reaction mixture was allowed to warm up to room temperature, poured on ice-cold water (200 ml), stirred for 0.5 h and extracted with MTBE (2 x 250 ml).
• Odour description floral, agrestic, fruity, green.
• Example 5 1-I ⁇ 1 .3S) -3-lsopropyl-1-methylcvclopentv ⁇ ethanol
• a solution of 1-[(1R,3S)-3-isopropyl-1-methylcyclopentyl]ethanone from Example 3 (3.0 g, 18 mmol) in ethanol (8 ml) was added to a cold (ice-bath) solution of sodium borohydride (0.42 g, 10.7 mmol) in the same solvent (17 ml). After 1.5 h stirring at room temperature, the reaction mixture was poured on ice-cold 2M HCI (100 ml) and extracted with MTBE (2 x 100 ml).
• Odour description hesperidic/citrus, fruity, green, fresh (grapefruit, rhubarb).
• DPG Dipropylene glycol
• DPG Dipropylene glycol

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Wood Science & Technology (AREA)
• Fats And Perfumes (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Cosmetics (AREA)

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• 2003
  • 2003-09-30 GB GBGB0322750.1A patent/GB0322750D0/en not_active Ceased
• 2004
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  • 2004-09-29 DE DE602004009814T patent/DE602004009814T2/de not_active Expired - Lifetime
  • 2004-09-29 US US10/572,804 patent/US20070054836A1/en not_active Abandoned
  • 2004-09-29 JP JP2006529545A patent/JP2007507434A/ja active Pending
  • 2004-09-29 EP EP04761944A patent/EP1668102B1/en not_active Expired - Lifetime
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