WO2011020909A2 - Organic compounds - Google Patents
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- WO2011020909A2 WO2011020909A2 PCT/EP2010/062161 EP2010062161W WO2011020909A2 WO 2011020909 A2 WO2011020909 A2 WO 2011020909A2 EP 2010062161 W EP2010062161 W EP 2010062161W WO 2011020909 A2 WO2011020909 A2 WO 2011020909A2
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- cyclopentylcyclohexanol
- weight
- fragrance
- oil
- trans
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Classifications
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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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/21—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a non-condensed ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/09—Geometrical isomers
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Definitions
- the present invention refers to c/s-3-cyclopentylcyclohexanol having appreciable leathery, suede odor notes and its use as a fragrance ingredient.
- This invention relates furthermore to fragrance compositions comprising it.
- bases can include compounds such as substituted quinolines, phenols and derivatives thereof as well as other ingredients of which the main odor descriptor is not leathery, for example, tetrahydroionol.
- 3-CycloalkyIcyclohexanols are known in the fragrance industry and they are generally regarded as providing floral/muguet notes with citrus, rhubarb and sometimes herbal connotations.
- Rossiter et al. describes in WO 98/47842, c/s-methyl-3- cyclohexylcyclohexan-1-ol having a weak, floral, woody odor note.
- C/s-3-cyclopentylcyclohexanol may be used alone, as mixtures of cis- and trans-3- cyclopentylcyclohexanol enriched in c/s-3-cyclopentylcyclohexanol, and/or in combination with a base material.
- the "base material” includes all known odorant 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 odorants in fragrance compositions, for example, carrier materials, and other auxiliary agents commonly used in the art.
- fragment composition means any composition comprising at least c/s-3-cyclopentylcyclohexanol and a base material, e.g. a diluent conventionally used in conjunction with odorants, such as dipropyleneglycol (DPG), isopropylmyristate (IPM), triethylcitrate (TEC) and alcohol ⁇ e.g. ethanol).
- a base material e.g. a diluent conventionally used in conjunction with odorants, such as dipropyleneglycol (DPG), isopropylmyristate (IPM), triethylcitrate (TEC) and alcohol ⁇ e.g. ethanol).
- DPG dipropyleneglycol
- IPM isopropylmyristate
- TEC triethylcitrate
- alcohol ⁇ e.g. ethanol
- oils and extracts e.g. castoreum, costus root oil, oak moss absolute, geranium oil, tree moss absolute, basil oil, fruit oils such as bergamot oil and mandarine oil, myrtle oil, palmarose oil, patchouli oil, petitgrain oil, jasmine oil, rose oil, sandalwood oil, wormwood oil, lavender oil or ylang-ylang oil;
- - alcohols e.g. cinnamic alcohol, c/s-3-hexenol, citronellol, EbanolTM, eugenol, farnesol, geraniol, Super MuguetTM, linalool, menthol, nerol, phenylethyl alcohol, rhodinol, SandaloreTM, terpineol or TimberoiTM;
- aldehydes and ketones e.g. Azurone ® (7- ⁇ 3-methyIbutyl)-1 ,5-benzodioxepin-3-one), anisaldehyde, ⁇ -amylcinnamaldehyde, GeorgywoodTM, hydroxycitronellal, lso E ® Super, Isoraldeine ® , Hedione ® , Lilial ® , maltol, methyl cedryl ketone, methylionone, verbenone or vanillin;
- Azurone ® (7- ⁇ 3-methyIbutyl)-1 ,5-benzodioxepin-3-one
- anisaldehyde e.g. Azurone ® (7- ⁇ 3-methyIbutyl)-1 ,5-benzodioxepin-3-one
- anisaldehyde e.g. Azurone ® (7- ⁇ 3-methy
- esters and lactones e.g. benzyl acetate, Cedryl acetate, ⁇ -decalactone, Helvetolide ® , ⁇ -undecalactone or Vetivenyl acetate;
- C/s-3-cydopentylcyclohexanoI may be used in a broad range of fragrance applications, e.g. in any field of fine and functional perfumery, such as perfumes, air care products, household products, laundry products, body care products and cosmetics. It can be employed in widely varying amounts, depending upon the specific application and on the nature and quantity of other odorant ingredients.
- the proportion is typically from 0.001 to 20 weight percent of the application. In one embodiment, it may be employed in a fabric softener in an amount of from 0.001 to 0.05 weight percent.
- the compound of the present invention may be used in fine perfumery in amounts of from 0.1 to 20 weight percent (e.g. up to about 10 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.
- C/s-3-cyclopentylcyclohexanol may be employed in a consumer product base simply by directly mixing cis-3-cyclopentyicyclohexanol, or a fragrance composition with the consumer product base, or it 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 it 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 consumer product base.
- 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 it may be chemically bonded
- the invention additionally provides a method of manufacturing a fragrance application, comprising the incorporation of c/s-3-cyclopentylcyclohexanol as a fragrance ingredient, either by directly admixing the compound to the consumer product base or by admixing a fragrance composition comprising it, which may then be mixed with a consumer product base, using conventional techniques and methods.
- a fragrance application comprising the incorporation of c/s-3-cyclopentylcyclohexanol as a fragrance ingredient, either by directly admixing the compound to the consumer product base or by admixing a fragrance composition comprising it, which may then be mixed with a consumer product base, using conventional techniques and methods.
- the invention furthermore provides a method for improving, enhancing or modifying a consumer product base by means of the addition thereto of an olfactorily acceptable amount of c/s-3-cyclopentylcyclohexanol.
- the invention also provides a fragrance application comprising: a) as odorant c/s-3-cyclopentylcyc!ohexanol; and
- consumer product base means a composition for use as a consumer product to fulfill specific actions, such as cleaning, softening, and caring or the like.
- examples of such products include fine perfumery, e.g. perfume and eau de toilette; fabric care, household products and personal care products such as laundry care detergents, rinse conditioner, personal cleansing composition, detergent for dishwasher, surface cleaner; laundry products, e.g. softener, bleach, detergent; body- care products, e.g. shampoo, shower gel; air care products and cosmetics, e.g.
- deodorant vanishing creme. This list of products is given by way of illustration and is not to be regarded as being in any way limiting.
- C/s-3-cyc!opentylcyclohexanol may be prepared starting from the commerciaily- available cyclohex-2-enone (1) via 3-cyclopentylcycIohexanone (2) followed by reduction of the ketone function to the corresponding secondary alcohol as shown in Scheme 1. Separation or enrichment of the diastereomeric pairs of enantiomers is possible, for example, by chromatographic techniques, distillation or crystallization techniques.
- enrichment is meant a mixture of cis- and frans-3-cyclopentylcyclohexanol enriched in c/s-3-cylclo ⁇ entylcyclohexanol, preferably in the ratio from about 3:1 to about 99:1 (cis/trans), e.g. from about 4:1 to about 9:1.
- the present invention refers in a further aspect to 3-cyclopentylcyclohexanoI wherein 3-cycIopentylcyclohexanol comprises at least 75 weight % of c/s-3- cyclopentylcyclohexanol. Further particulars as to reaction conditions are provided in the examples.
- Odor description strong leathery, suede, animalic character with slight floral, green, Sassafras connotation.
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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)
- Cosmetics (AREA)
Abstract
Cis-3-cyclopentylcyclohexanol and its use as a fragrance ingredient.
Description
ORGANIC COMPOUNDS
The present invention refers to c/s-3-cyclopentylcyclohexanol having appreciable leathery, suede odor notes and its use as a fragrance ingredient. This invention relates furthermore to fragrance compositions comprising it.
In modern perfumery leathery notes are used to bring natural textures, such as suede, to fragrance compositions. They are found in the heart and base of many fragrances ranging from strong, seductive masculine to bold feminine perfumes as well as many home and personal care products. Thus there is an ongoing demand for new compounds possessing these odor notes.
Leathery, suede notes in fragrance compositions are usually obtained by addition of multiple component bases. These bases can include compounds such as substituted quinolines, phenols and derivatives thereof as well as other ingredients of which the main odor descriptor is not leathery, for example, tetrahydroionol.
Surprisingly, it has now been found that c/s-3-cyclopentylcyclohexanol possesses a strong leathery, suede, animalic type odor.
3-CycloalkyIcyclohexanols are known in the fragrance industry and they are generally regarded as providing floral/muguet notes with citrus, rhubarb and sometimes herbal connotations. For example, Rossiter et al. describes in WO 98/47842, c/s-methyl-3- cyclohexylcyclohexan-1-ol having a weak, floral, woody odor note.
In one aspects there is provided the use as fragrance of c/s-3-cyclopentylcyclohexanol.
C/s-3-cyclopentylcyclohexanol may be used alone, as mixtures of cis- and trans-3- cyclopentylcyclohexanol enriched in c/s-3-cyclopentylcyclohexanol, and/or in combination with a base material. As used herein, the "base material" includes all known odorant 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 odorants in fragrance compositions, for example, carrier materials, and other auxiliary agents commonly used in the art.
As used herein, "fragrance composition" means any composition comprising at least c/s-3-cyclopentylcyclohexanol and a base material, e.g. a diluent conventionally used in conjunction with odorants, such as dipropyleneglycol (DPG), isopropylmyristate (IPM), triethylcitrate (TEC) and alcohol {e.g. ethanol).
The following list comprises examples of known odorant molecules, which may be combined with the compounds of the present invention:
- essential oils and extracts, e.g. castoreum, costus root oil, oak moss absolute, geranium oil, tree moss absolute, basil oil, fruit oils such as bergamot oil and mandarine oil, myrtle oil, palmarose oil, patchouli oil, petitgrain oil, jasmine oil, rose oil, sandalwood oil, wormwood oil, lavender oil or ylang-ylang oil;
- alcohols, e.g. cinnamic alcohol, c/s-3-hexenol, citronellol, Ebanol™, eugenol, farnesol, geraniol, Super Muguet™, linalool, menthol, nerol, phenylethyl alcohol, rhodinol, Sandalore™, terpineol or Timberoi™;
- aldehydes and ketones, e.g. Azurone®(7-{3-methyIbutyl)-1 ,5-benzodioxepin-3-one), anisaldehyde, α-amylcinnamaldehyde, Georgywood™, hydroxycitronellal, lso E® Super, Isoraldeine®, Hedione®, Lilial®, maltol, methyl cedryl ketone, methylionone, verbenone or vanillin;
- ethers and acetals, e.g. Ambrox™, geranyl methyl ether, rose oxide or
Spirambrene™;
- esters and lactones, e.g. benzyl acetate, Cedryl acetate, γ-decalactone, Helvetolide®, γ-undecalactone or Vetivenyl acetate;
- macrocycles, e.g. Ambrettolide, ethylene brassylate or Exaltolide®;
- heterocycles, e.g. isobutylquinoline.
C/s-3-cydopentylcyclohexanoI may be used in a broad range of fragrance applications, e.g. in any field of fine and functional perfumery, such as perfumes, air care products, household products, laundry products, body care products and cosmetics. It can be employed in widely varying amounts, depending upon the specific application and on the nature and quantity of other odorant ingredients. The proportion is typically from 0.001 to 20 weight percent of the application. In one embodiment, it may be employed in a fabric softener in an amount of from 0.001 to 0.05 weight percent. In another embodiment, the compound of the present invention may be used in fine perfumery in amounts of from 0.1 to 20 weight percent (e.g. up to about 10 weight percent), more preferably between 0.1 and 5 weight percent. However, 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.
C/s-3-cyclopentylcyclohexanol may be employed in a consumer product base simply by directly mixing cis-3-cyclopentyicyclohexanol, or a fragrance composition with the consumer product base, or it 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 it 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 consumer product base.
Thus, the invention additionally provides a method of manufacturing a fragrance application, comprising the incorporation of c/s-3-cyclopentylcyclohexanol as a fragrance ingredient, either by directly admixing the compound to the consumer product base or by admixing a fragrance composition comprising it, which may then be mixed with a consumer product base, using conventional techniques and methods. Through the addition of an olfactory acceptable amount of c/s-3-cyclopentylcyclohexanol the odor notes of a consumer product base will be improved, enhanced or modified.
Thus, the invention furthermore provides a method for improving, enhancing or modifying a consumer product base by means of the addition thereto of an olfactorily acceptable amount of c/s-3-cyclopentylcyclohexanol. The invention also provides a fragrance application comprising:
a) as odorant c/s-3-cyclopentylcyc!ohexanol; and
b) a consumer product base.
As used herein, "consumer product base" means a composition for use as a consumer product to fulfill specific actions, such as cleaning, softening, and caring or the like. Examples of such products include fine perfumery, e.g. perfume and eau de toilette; fabric care, household products and personal care products such as laundry care detergents, rinse conditioner, personal cleansing composition, detergent for dishwasher, surface cleaner; laundry products, e.g. softener, bleach, detergent; body- care products, e.g. shampoo, shower gel; air care products and cosmetics, e.g.
deodorant, vanishing creme. This list of products is given by way of illustration and is not to be regarded as being in any way limiting.
C/s-3-cyc!opentylcyclohexanol may be prepared starting from the commerciaily- available cyclohex-2-enone (1) via 3-cyclopentylcycIohexanone (2) followed by reduction of the ketone function to the corresponding secondary alcohol as shown in Scheme 1. Separation or enrichment of the diastereomeric pairs of enantiomers is possible, for example, by chromatographic techniques, distillation or crystallization techniques.
Scheme 1 :
cis~Z trans-S
By enrichment is meant a mixture of cis- and frans-3-cyclopentylcyclohexanol enriched in c/s-3-cylcloρentylcyclohexanol, preferably in the ratio from about 3:1 to about 99:1 (cis/trans), e.g. from about 4:1 to about 9:1.
Thus the present invention refers in a further aspect to 3-cyclopentylcyclohexanoI wherein 3-cycIopentylcyclohexanol comprises at least 75 weight % of c/s-3- cyclopentylcyclohexanol.
Further particulars as to reaction conditions are provided in the examples.
The invention is now further described with reference to the following non-limiting examples. These examples are for the purpose of iliustration only and it is understood that variations and modifications can be made by one skilled in the art.
All products described in the Examples were obtained starting from commercially available cyclohex-2-enone. Chemical shifts (δ) of the NMR spectra are reported in ppm downfield from TMS; coupling constants J in Hz.
Example 1: c/s-3-CyclopentylcyclohexanoI (c/s-3) a) 3-Cycloρentylcyclohexanone (2)
Cyclopentylmagnesium chloride (10 ml, 1 M solution in diethyl ether) was added over 5 min to a stirred suspension of magnesium (32.6 g, 1.34 mol) in THF (1000 ml). After stirring at room temperature for 15 min bromocyclopentane (200 g, 1.34 mol) was added over 50 min and the suspension cooled to -700C. Copper (I) bromide (193 g, 1.34 mol) was then added in portions followed by a solution of cyclohex-2-enone (1, 117 g, 1.2 mol) in THF (150 ml) over 135 min. The suspension was stirred for a further 30 min at a temperature between -60 and -700C before being quenched with sat. aq. ammonium chloride solution (1000 ml). After warming to room temperature, MTBE (200 ml) was added and the suspension filtered. The phases were separated and the aqueous phase extracted with MTBE (200 ml). The organic phases were combined, washed with 2 portions of sat. aq. ammonium chloride solution (2 x 200 ml), dried over magnesium sulphate and concentrated in vacuo to give a brown oil (176 g). Fractional distillation of 156 g of the brown oil at reduced pressure (92°C, 1 mbar) gave 2 (94 g, 99% pure GC) as a colorless oil. 1H NMR (CDCI3): δ 2.47 (ddt, J = 13.6, 4.0, 2.0, 1H), 2.35 (m, 1 H), 2.26 (dddd, J = 14.2, 12.4, 6.3, 1.3, 1 H), 2.06 (ddd, J = 13.9, 11.6, 1.3, 1H), 2.05 (m, 1 H), 1.94 (m, 1H), 1.85 - 1.71 (m, 2H), 1.70 - 1.46 (m, 7H), 1.37 (dddd, J = 13.4, 12.1, 10.6, 3.5, 1 H), 1.19 - 1.04 (m, 2H). 13C NMR (CDCI3): S 212.1 (S), 47.4 (T), 46.2 (D), 44.9 (D), 41.5 (T), 30.6 (T), 30.4 (T)1 30.3 (T), 25.4 (T), 25.1 (2T). MS: 166 (M+ (4)), 148 (3), 123 (16), 108 (24), 98 (14), 97 (100), 81 (11), 69 (23), 67 (27), 55 (38), 41 (34), 39 (12).
b) c/s-3-Cyc!opentylcyclohexanoI (c/s-3) and fraAϊs-3-cyclopentyIcyclohexanol (trans-3)
Sodium borohydride (3.4 g, 0.09 mol) was added over 30 min to a stirred solution of 3- cyclopentylcyclohexanone (2, 30 g, 0.18 mol), described in Example 1a, in 2-ρropanol (300 ml) while keeping the temperature below 300C. After stirring at room temperature for 3 h and standing overnight, the gelatinous solution was poured onto a mixture of acetic acid (10 m!) and water (250 ml). The product was extracted with MTBE (200 ml) and the organic phase washed successively with water (2 x 200 ml), potassium carbonate solution (200 ml) and water (200 ml). The organic phase was then dried over magnesium sulphate, concentrated in vacuo and purified by flash chromatography (silica gel, MTBE/hexane 1 :1). The cis/trans isomers were separated under these conditions and bulb-to-bulb distillation gave olfactory pure samples of 99% GC pure cis- 3-cyclopentylcyclohexanol (c/s-3, 6.5 g) and frans-3-cyclopentylcyclohexanol (trans-3, 4.2 g) as white crystalline solids, melting points = 42-440C and 37-390C respectively. A mixture of cis- and trans-3 (7.7 g, cis/trans ratio 95:5) was also obtained by combining the intermediate fractions.
C/s-3-cyclopentylcyclohexanol: 1H NMR (C6D6): δ 3.39 (tt, J = 10.1 , 4.6, 1H), 1.99 (m, 1H), 1.94 - 1.87 (m, 2H (1OH)), 1.75 - 1.40 (m, 8H), 1.38 (m, 1 H), 1.18 - 0.91 (m, 5H), 0.86 (q, J = 11.4, 1 H), 0.67 (m, 1 H). 13C NMR (C6D6): δ 70.7 (D), 46.8 (D), 42.5 (D), 42.0 (T), 36.2 (T), 31.4 (T), 30.9 (T), 30.8 (T), 25.6 (T), 25.6 (T), 24.6 (T). MS: 150 (M+ - 18 (35)), 135 (24), 121 (23), 109 (27), 108 (35), 99 (17), 95 (21), 94 (18), 83 (32), 82 (100), 81 (92), 80 (23), 79 (29), 69 (24), 68 (37), 67 (81), 57 (48), 55 (56), 41 (48).
Odor description: strong leathery, suede, animalic character with slight floral, green, Sassafras connotation.
7rans-3-cyclopentylcyc!ohexanol: 1H NMR (DMSO-d6): δ 4.16 (d, J = 3.3, 1H (OH)), 3.82 (qid, J = 3.6, 3.3, 1H), 1.74 - 1.28 (m, 14H), 1.12 (ddd, J = 12.9, 10.1, 2.8, 1 H), 1.09 - 0.88 (m, 3H). 13C NMR (DMSO-d6): 64.3 (D), 45.2 (D), 38.5 (T), 36.7 (D), 33.0 (T), 30.9 (T), 30.2 (T), 30.0 (T), 24.8 (T), 24.8 (T), 19.8 (T). MS: 150 (M+- 18 (36), 135 (19), 121 (20), 109 (28), 108 (24), 99 (19), 95 (18), 94 (18), 83 (28), 82 (100), 81 (100), 80 (25), 79 (31), 69 (25), 68 (33), 67 (70), 57 (49), 55 (55), 41 (47).
Example 2: Perfuming Composition for Female Fragrance
Darts bv weiqht
Ambrettolide {9-hexadecen-16-olide) 95
Ambrofix (3aR, 5aS, 9aS, 9bR)-dodecahydro-3a,6,6,9a-tetramethyI- naptho[2,1-b]furan 1
Angelique Seed Oil 1
Beta lonone 8
Butyl Hydroxy Toluene 15
Coumarine 10
Diethyl Phtalate 180
Ethyl Vanilline 100
Evernyl (methyl 2,4-dihydroxy-3,6-dimethylbenzoate) 1
Hedione (methyl 2-(3-oxo-2-pentylcyclopentyl)acetate) 300
Heliotropine 40
Mandarine Oi! 15
Nonanal 10% DPG 8
Patchouli Oil 20
Peach Pure (5-heptyldihydrofuran-2(3H)-one) 1
Vanilline 50
Velvione (cyclohexadec-5-ene-1 -one) 75
TOTAL 920
Addition of 80 parts by weight of c/s-3-cycIopentylcyclohexanol (10% DEP) to the above-described perfuming composition gives an enhanced level of sophistication, enveloping the voluptuous accord of amber and heliotrope with a unique leathery signature. The invention's compound increases volume and dresses the musky notes up as a tantalising dry-down whilst still being controlled by the sensuous, warm aroma of vanilla.
Example 3: Perfuming Composition for Unisex Fragrance
parts by weight
Bergamot Oil 30 Cashmeran (1,1 ,2,3,3-pentamethyl-2,3,6,7-tetrahyclro-1H-inden-4(5H)-one) 25 Cedrat Oil 25
Cinnamic Alcohol 20
Ciste Oil 1
Evernyl (methyl 2,4-dihydroxy-3,6-dimethylbenzoate) 7 Georgywood (c/s-1-(1 ,2,8,8-tetramethyl-1 ,2,3,4,5,6,7,8-octahydro- naphtha1en-2-yl)ethanone) 200
Hedione (methyl 2-(3-oxo-2-pentylcyclopentyl)acetate) 25 lonone 8 lsopropyl Myristate 245 lsoraldeine Cetone Alpha 90 Linalool 15
Neroli Oii 1
Patchouli Oil 75
Peach Pure (5-heptyldihydrofuran-2(3H)-one) 3 Serenolide (2-(1-(3,3-dimethyIcyclohexyl)ethoxy)-2-methylproρyI- cyclopropanecarboxylate) 90
Vanilline 15
TOTAL 875
Addition of 25 parts by weight of c/s-3-cycIopentyIcyclohexanoI (10% DEP) to the above-described perfuming composition gives a defined suede signature, recreating a leathery note with the blend of patchouli and violet. The invention's compound brings a pleasant vibration with the hesperidic accord and enhances the seductive dry-down of the white musk.
Claims
1. 3-Cydopentylcyclohexanol wherein 3-cyclopentylcyclohexanol consisting of at least 75 weight % of c/s-3-cyclopentylcyclohexanol and up to 25 weight % of trans-3- cyclopentylcyclohexanol.
2. 3-Cyclopentylcyclohexanol according to claim 2 consisting of at least 90 weight % of c/s-3-cyclopentyIcyclohexanoi.
3. C/s-3-cyclopentylcyclohexanol.
4. C/s-3-cyclopentylcyclohexanol exhibiting an odor note selected from: leathery, suede odor notes.
5. The use as fragrance ingredient of 3-cyclopentylcyclohexanol consisting of at least 75 weight % of c/s-3-cyclopentylcyclohexanol and up to 25 weight % of trans-3- cyclopentylcyclohexanol.
6. The use as fragrance ingredient of c/s-3-cyclopentylcyclohexanol which said c/s-3- cyclopentylcyclohexanol exhibits an odor note selected from: leathery, suede odor notes.
7. A fragrance composition or fragrance application comprising 3- cyclopentylcyclohexanol wherein 3-cyclopentylcyclohexanol consisting of at least 75 weight % of c/s-3-cyclopentylcyclohexanol and up to 25 weight % of trans-3- cyclopentylcyclohexanol.
8. A method of manufacturing a fragrance application, comprising the step of
incorporation 3-cyclopentylcyclohexanol to a base material wherein 3- cyclopentylcyclohexanol consisting of at least 75 weight % of c/s-3- cyclopentylcyclohexanol and up to 25 weight % of fra/?s-3-cyclopentylcyc!ohexanol.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0914575.6 | 2009-08-20 | ||
| GBGB0914575.6A GB0914575D0 (en) | 2009-08-20 | 2009-08-20 | Organic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2011020909A2 true WO2011020909A2 (en) | 2011-02-24 |
| WO2011020909A3 WO2011020909A3 (en) | 2011-06-23 |
Family
ID=41171675
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2010/062161 WO2011020909A2 (en) | 2009-08-20 | 2010-08-20 | Organic compounds |
Country Status (2)
| Country | Link |
|---|---|
| GB (1) | GB0914575D0 (en) |
| WO (1) | WO2011020909A2 (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998047842A1 (en) | 1997-04-23 | 1998-10-29 | Quest International B.V. | Perfumes comprising 3-alkylcycloalkanols |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69202372D1 (en) * | 1991-03-22 | 1995-06-14 | Firmenich & Cie | Tertiary alcohol containing camphole structure unit and its use as a fragrance. |
| EP1605035B1 (en) * | 2004-06-08 | 2007-09-19 | Firmenich Sa | Perfuming ingredients of the woody type |
| EP2039670B1 (en) * | 2007-09-20 | 2010-03-10 | Symrise GmbH & Co. KG | 6-methyl-4-(2',2',3'-trimethyl-3'-cyclopentene-1'-yl)-2-cyclohexene-1-ol as sandalwood aroma |
-
2009
- 2009-08-20 GB GBGB0914575.6A patent/GB0914575D0/en not_active Ceased
-
2010
- 2010-08-20 WO PCT/EP2010/062161 patent/WO2011020909A2/en active Application Filing
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998047842A1 (en) | 1997-04-23 | 1998-10-29 | Quest International B.V. | Perfumes comprising 3-alkylcycloalkanols |
Also Published As
| Publication number | Publication date |
|---|---|
| GB0914575D0 (en) | 2009-09-30 |
| WO2011020909A3 (en) | 2011-06-23 |
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