Classifications

• • 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
  • C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring

Definitions

• This invention relates to aryl-cycloalkanes, in particular phenyl-cycloalkanes, having spicy and anisic odour notes and to flavour and fragrance compositions containing one or more of the compounds.
• flavour or fragrance composition comprising a compound of formula (I)
• R 1 is hydrogen, OH, or alkoxy having 1 to 3 carbon atoms
• R 2 is hydrogen, OH, or alkoxy having 1 to 3 carbon atoms, with the proviso that compounds of formula (I), wherein R 1 and R 2 are both hydrogen are excluded, or
• R 1 and R 2 taken together is a divalent radical -O-CH 2 -O-, R 3 is hydrogen, or -CH 3 ,
• R 4 is hydrogen, or -CH 3 , or
• R 3 and R 4 taken together is a divalent radical (CH 2 ) n , C(CH 3 ) 2 , or CH(CH 3 ) which forms a cycloalkane ring together with the carbon atoms to which it is attached,
• R 5 is hydrogen, or -CH 3
• R 6 is hydrogen, or -CH 3 , or
• R 5 and R 6 taken together is a divalent radical (CH 2 ) n , (CH 2 ) n-1 CH(CH 3 ), or
• n is an integer 1 , 2, or 3, and wherein at least one cycloalkane ring is present.
• Compounds of the formula (I) employed in a composition according to the invention show good diffusion and high substantivity, leading to persistence of odour.
• 1 -cyclopropyl methyl-4-methoxy-benzene has an olfactometer odour threshold value 80 times lower than estragol, measured by analogy disclosed in the Journal of Agr. Food Chem., Vol. 19, No. 6, 1971 , 1049 - 1056.
• a particularly preferred composition according to the invention may comprise a compound of formula (I) selected from l-Cyclopropylmethyl-4-methoxy-benzene, 4-Cyclopropylmethyl-2-methoxy-phenol, 4-Cyclopropylmethyl-1 ,2-dimethoxy-benzene, 2-Methoxy-4-(2-methyl-cyclopropyl)-phenol, 1-Cyclobutylmethyl-4-methoxy-benzene and 1-Cyclopentylmethyl-4-methoxy-benzne.
• a most preferred composition comprises 1 - Cyclopropylmethyl-4-methoxy-benzene.
• R 1 is hydrogen, OH, or alkoxy having 1 to 3 carbon atoms
• R 2 is hydrogen, OH, or alkoxy having 1 to 3 carbon atoms, with the proviso that compounds of formula (I) wherein, i) R 1 , R 2 is hydrogen, ii) R 1 is hydrogen and R 2 is methoxy, iii) R 1 is hydrogen and R 2 is hydroxy are excluded, or
• R 1 and R 2 taken together is a divalent radical -O-CH 2 -O-,
• R 3 is hydrogen, R 4 is hydrogen, or
• R 3 and R 4 taken together is a divalent radical - CH 2 - which forms a cycloalkane ring together with the carbon atoms to which it is attached,
• R 5 is hydrogen
• R 6 is hydrogen, or R 5 and R 6 taken together is a divalent radical - CH 2 - which forms a cycloalkane ring together with the carbon atoms to which it is attached, and wherein at least one cycloalkane ring is present.
• Particularly preferred compounds of formula (I) are 4-Cyclopropylmethyl-2-methoxy- phenol, 4-Cyclopropylmethyl-1 ,2-dimethoxy-benzene and 2-Methoxy-4-(2-methyl- cyclopropyl)-phenol.
• the compounds of formula (I) may be synthesised from commonly available starting materials and reagents according to synthetic protocols known in the art.
• Benzene-(2-alkyl-cyclopropyl) compounds of the formula (I) may be synthesised from the corresponding (l-propenyl)-benzene, e.g. 1- methoxy-4-(1-propenyl)-benzene using the reagents described above according to an analogous synthetic protocol.
• Benzene-alkyl-cycloalkyl compounds of the formula (I) may be synthesised by analogy to those methods disclosed in J. Organomet. Chem. (1986), 302(1), 5-17, which is hereby incorporated by reference.
• Compounds of formula (I) may be used alone or as a mixture in a composition according to the present invention.
• the compounds may be used in combination with other known flavourant or odourant molecules selected from the extensive range of natural and synthetic molecules currently available and/or in admixture with one or more ingredients or excipients conventionally used in conjugation with odourants or flavourants in fragrance or flavour compositions, for example carrier materials, and other auxiliary agents commonly used in the art.
• the compounds of formula (I) may be used in fragrance applications, e.g. in any field of fine and functionary perfumery, such as perfumes, household products, laundry products, body care products and cosmetics.
• fragrance applications e.g. in any field of fine and functionary perfumery, such as perfumes, household products, laundry products, body care products and cosmetics.
• the high diffusion and substantivity of compounds of formula (I) is well perceived on fabrics washed with detergent or treated with a softener comprising them.
• the typical spicy anisic odour is already perceived on wet fabric and lingers for long periods, e.g. 2 - 4 days on the dry fabric.
• the compounds of formula (I) may be used in flavour applications and are useful in modifying for example, spicy flavours and seasonings for condiments and meats. They may be used in aromatic, herbal and spicy flavourings, heavy fruit flavours (e.g. raisin, prune) and in flavours for Root beer.
• the compounds of formula (I) are also well
• the compounds of the formula (I) may be present in compositions in amounts ranging from 0.001 to 1000 mg/kg, more preferably from 0.05 to 500 mg/kg.
• compounds of the formula (I) can be employed in wide ranging amounts depending upon the specific application. For example, from about 0.001 to about 10 weight percent.
• One application may be a fabric softener comprising about 0.001 to 0.05 weight percent.
• An other application may an alcoholic solution comprising about 0.1 to 10 weight percent.
• the preferred concentrations vary between about 0.1 and 5 weight percent. However, the values should not be limiting on the present invention, since the experienced perfumer may also achieve effects with even lower concentrations or may create novel accords with even higher amounts.
• CH 2 Br 2 (220g) was added to a slurry of zinc powder (340g) and CuCI (54g) in diethyl ether (450 ml).
• the reaction was started by the addition of acetyl chloride (8g).
• the reaction mixture was heated to 45°C and a solution of estragol (192g) in ether (150ml) was added during 25 minutes.
• Additional CH 2 Br 2 (456g) dissolved in ether (150ml) was dropped into the grey-red suspension during 45 minutes. Afterwards, the mixture was stirred at 50°C for 12 hours. The suspension was cooled to room temperature and MTBE (900ml) was added.
• the compound has useful odourant properties having an anisic, estragol, anethole, cresolic, strong odor.
• the compound has useful odourant properties having fruity, coriander, anisic, estragol, pear, hesperidic, verdyle odor.
• the compound has useful odourant properties having eugenol, spicy, peppery, phenolic, thymol odour.
• the compound has useful odourant properties having estragon, anisic, spicy, animalic odour.
• a solution of AICI 3 (13.4g) in nitroethane (25ml) was added to a solution of cyclobutane carboxylic acid (10.0g) and anisole (10.8g) in nitroethane (75 ml) at 10 C C.
• the mixture was stirred for 5hours at room temperature, was than poured on ice and extracted with MTBE.
• the organic phase was washed with aqueous sodium hydroxide, water and brine, dried (MgSO ) and concentrated in vacuo.
• the essentially clean ketone (10.8g) was used in the next step.
• the compound has useful odourant properties having anisic, spicy, slightly cuminic, fresh odour.
• the compound has useful odourant properties having anisic, spicy, slightly cuminic, herbaceous odour.
• Example 7 A fougere spicy aromatic masculine fragrance was made with the following ingredients
• 1-cyclopropylmethyl-4-methoxy-benzene blends excellently with the anisic and spicy notes of the fragrance.
• the above fragrance has more character, is fresher and blends much better with the minty note of the top but also with the animalic notes of the dry down.

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

Priority Applications (8)

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Publications (2)

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• 2001
  • 2001-06-30 EP EP01115991A patent/EP1269982A1/en not_active Withdrawn
• 2002
  • 2002-06-28 AT AT02740179T patent/ATE471142T1/de not_active IP Right Cessation
  • 2002-06-28 DE DE60236729T patent/DE60236729D1/de not_active Expired - Lifetime
  • 2002-06-28 US US10/481,733 patent/US7704942B2/en not_active Expired - Lifetime
  • 2002-06-28 BR BRPI0210749-0B1A patent/BR0210749B1/pt active IP Right Grant
  • 2002-06-28 MX MXPA03010821A patent/MXPA03010821A/es active IP Right Grant
  • 2002-06-28 WO PCT/CH2002/000352 patent/WO2003002084A2/en not_active Ceased
  • 2002-06-28 ES ES02740179T patent/ES2346741T3/es not_active Expired - Lifetime
  • 2002-06-28 AU AU2002315612A patent/AU2002315612A1/en not_active Abandoned
  • 2002-06-28 JP JP2003508324A patent/JP4088250B2/ja not_active Expired - Lifetime
  • 2002-06-28 EP EP02740179A patent/EP1401388B1/en not_active Expired - Lifetime
  • 2002-06-28 CN CNB028117107A patent/CN1245934C/zh not_active Expired - Lifetime

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