Cyclic oxyether compounds as fragrance ingredients

Abstract

The present invention provides a compound represented by formula (I): wherein the dotted line represents a carbon-carbon single bond or double bond, p represents 0 to 3, preferably 1 to 3, n represents 0 to 2, R represents each independently a C1 to C6 alkyl group or a C2 to C6 alkenyl group, each optionally substituted by an ester group, and R 1 are each independently a hydrogen atom or a C1-C3 alkyl group] or a mixture thereof as a perfuming ingredient for imparting, for example, floral-green (such as jasmine) and watery-type odor notes.

Description

[Technical field]

[0001] The present invention relates to the field of perfumery. More particularly, the present invention relates to the use of cyclic oxyether compounds as perfuming ingredients. The present invention relates to the use of said compounds in the perfume industry, and to perfuming compositions or perfumed articles containing said compounds.

[0002] Background technology To our knowledge, the compounds of the present invention are not known as perfuming compounds, or as having an odor in general.

[0003] WO 2011 / 101757 describes compounds which have similar odor notes but differ from those of the present invention in that the carbonyl group lacks an alkyl ether substituent.

[0004] To the best of our knowledge, said prior art does not report or suggest any organoleptic properties of the compounds of formula (I) or any use of said compounds in the field of perfumery.

[0005] Summary of the Invention The present invention relates to compounds of formula (I) which impart a floral-green (jasmine-like) note and a watery note.

[0006] Therefore, a first object of the present invention is to provide a compound of formula (I) [ka] [In the formula, The dotted lines represent carbon-carbon single or double bonds; p represents 0 to 3, preferably 1 to 3; n is an integer from 0 to 2, R each independently represents a C1-C6 alkyl group or a C2-C6 alkenyl group optionally substituted by an ester group; R 1 each independently represents a hydrogen atom or a C1-C3 alkyl group. in the form of any one of its isomers or a mixture thereof, as a perfuming ingredient.

[0007] A second object of the present invention is a method for imparting, enhancing, improving or modifying the odor characteristics of a perfuming composition or a perfumed article, comprising the step of: [ka] [In the formula, The dotted lines represent carbon-carbon single or double bonds; p represents 0 to 3, preferably 1 to 3; n is an integer from 0 to 2, R each independently represents a C1-C6 alkyl group or a C2-C6 alkenyl group optionally substituted by an ester group; R 1 each independently represents a hydrogen atom or a C1-C3 alkyl group. in the form of any one of its isomers or a mixture thereof.

[0008] The third object of the present invention is to provide a compound represented by the formula (I) [ka] [In the formula, The dotted lines represent carbon-carbon single or double bonds; p represents 0 to 3, preferably 1 to 3; n is an integer from 0 to 2, R each independently represents a C1-C6 alkyl group or a C2-C6 alkenyl group optionally substituted by an ester group; R 1 are each independently a hydrogen atom or a C1-C3 alkyl group, However, 4-(cyclopentyloxy)butanal, 4-(cyclopentyloxy)-2-ethyl-2-methylbutanal, 5-(cyclopentyloxy)pentanal, 5-(cyclopentyloxy)-2-ethyl-2-methylpentanal and 5-(cyclopentyloxy)-2,2-dimethylpentanal are excluded. in the form of any one of its isomers or a mixture thereof.

[0009] Another object of the present invention is to i) at least one compound of formula (I) as defined above, ii) at least one ingredient selected from the group consisting of a perfume carrier and a perfume base; and iii) optionally at least one flavoring adjuvant; A fragrance composition comprising:

[0010] A further object of the present invention is a perfumed consumer product comprising at least one compound of formula (I) as defined above or a perfumed composition as defined above.

[0011] Description of the invention Surprisingly, the compound of formula (I) in the form of any one of its isomers or a mixture thereof [ka] [In the formula, The dotted lines represent carbon-carbon single or double bonds; p represents 0 to 3, preferably 1 to 3; n is an integer from 0 to 2, R each independently represents a C1-C6 alkyl group or a C2-C6 alkenyl group optionally substituted by an ester group; R 1 each independently represents a hydrogen atom or a C1-C3 alkyl group. It has been found that the compounds of the formula (I) can be used as perfuming ingredients to impart, for example, floral-green (like jasmine) and watery type odour notes.

[0012] For reasons of clarity, with regard to the expression "any one of its stereoisomers or a mixture thereof" or similar expressions, the usual meaning understood by a person skilled in the art is meant, i.e. that the compound of formula (I) may be a pure enantiomer or a diastereomer. In other words, the compound of formula (I) may have several stereocenters, each of which may have two different stereochemistries (e.g. R or S). The compound of formula (I) may be in the form of a pure enantiomer or even in the form of a mixture of enantiomers or diastereomers. The compound of formula (I) may be in racemic or scalemic form. Thus, the compound of formula (I) may be in the form of a stereoisomer or a composition of matter that comprises or consists of various stereoisomers.

[0013] For reasons of clarity, the expression "optionally substituted by an ester group" or similar expressions should be interpreted in a manner that is consistent with the ordinary meaning understood by a person skilled in the art, i.e., one hydrogen of an alkyl or alkenyl group is substituted with an OC(=O)R a Group or C(=O)OR a group [R a is a hydrogen atom or C 1-4 It means that it may be substituted by an alkyl group, which may represent an alkyl group.

[0014] According to a particular embodiment, in the compounds of formula (I), p may represent 1, 2 or 3, preferably 1 or 2, even more preferably 1.

[0015] According to a particular embodiment, in the compounds of formula (I), n may represent 1 or 2, preferably 1.

[0016] According to certain embodiments, in the compounds of formula (I), the dotted line may be a carbon-carbon double bond.

[0017] According to a particular embodiment of the invention, the compound of formula (I) has the formula (II) [ka] [Wherein, p, R and R 1 The definition of is the same as above.

[0018] According to a particular embodiment, in the compounds of formula (II), p may represent 1 or 2, preferably 1.

[0019] According to a particular embodiment, in the compounds of formula (I) or (II), R may represent, independently of each other, a C1-C5 alkyl group or a C2-C5 alkenyl group, optionally substituted by an ester group. Preferably, R may represent a C1-C5 alkyl group. Even more preferably, R may represent a methyl group, a pentyl group or an isopentyl group.

[0020] According to a particular embodiment of the invention, the compound of formula (I) or in particular the compound of formula (II) has the formula (III) [ka] [In the formula, R 1 has the same meaning as above, R 2 represents a C1-C6 alkyl group or a C2-C6 alkenyl group, R 3 represents a hydrogen atom or a C1-C6 alkyl group.

[0021] According to a particular embodiment, in the compound of formula (III), R 2 may be a C2-C5 alkyl group or a C2-C5 alkenyl group, preferably a C3-C5 alkyl group or a C3-C5 alkenyl group, preferably a C5 alkyl group, even more preferably a pentyl group or an isopentyl group. According to one particular embodiment, in the compound of formula (III), R 3 may be a hydrogen atom or a C1-C3 alkyl group, preferably a hydrogen atom or a methyl group, and even more preferably a hydrogen atom.

[0022] According to a particular embodiment, in the compounds of formula (I)-(II), R1 may each independently represent a hydrogen atom or a C1-C2 alkyl group, preferably a hydrogen atom or a methyl group.

[0023] According to a particular embodiment, in the compounds of formulae (I) to (III), all R 1 may represent a hydrogen atom.

[0024] According to a particular embodiment, in the compounds of formulae (I) to (III), one R 1 may represent a methyl group, and the remaining R 1 may represent a hydrogen atom.

[0025] According to any one of the above embodiments of the present invention, the compounds of formulae (I) to (III) are 10 ~C 16 Compounds, preferably C 11 ~C 15 Compounds, more preferably C 14 ~C 15 It is a compound.

[0026] For reasons of clarity, with respect to the phrase "the dotted line represents a carbon-carbon single or double bond" or similar phrases, it is meant to have the ordinary meaning as understood by a person skilled in the art, i.e., that the entire bond between the carbon atoms connected by the dotted line (e.g., a solid line and a dotted line) is a carbon-carbon single or double bond.

[0027] The compounds of formula (I) are all novel compounds and therefore also another object of the present invention, with the exception of 4-(cyclopentyloxy)butanal, 4-(cyclopentyloxy)-2-ethyl-2-methylbutanal, 5-(cyclopentyloxy)pentanal, 5-(cyclopentyloxy)-2-ethyl-2-methylpentanal and 5-(cyclopentyloxy)-2,2-dimethylpentanal.

[0028] As stated above, the odor of the compounds of the present invention is characterized by green notes, and often by floral-green (jasmine-like) notes and watery notes.

[0029] As a specific example of the present invention, mention may be made, by way of non-limiting example, of (±)-4-[(2-pentyl-2-cyclopenten-1-yl)oxy]butanal, which exhibits fresh, green, natural and watery notes. The green note does not impart an earthy or musty note. It is furthermore noteworthy that said compound blends particularly well with the floral note of Hedione®, the watery note of Calone® and the green note of (Z)-3-hexen-1-ol.

[0030] Further examples include (±)-4-{[2-(3-methylbutyl)-2-cyclopenten-1-yl]oxy}butanal, (±)-2-methyl-3-[(3-methyl-2-pentyl-2-cyclopenten-1-yl)oxy]propanal or (±)-5-[(2-pentyl-2-cyclopenten-1-yl)oxy]pentanal, each of which has a similar but slightly weaker odor to (±)-4-[(2-pentyl-2-cyclopenten-1-yl)oxy]butanal.

[0031] According to a particular embodiment of the invention, the compound of formula (I) is (±)-4-[(2-pentyl-2-cyclopenten-1-yl)oxy]butanal, (±)-4-{[2-(3-methylbutyl)-2-cyclopenten-1-yl]oxy}butanal, (±)-2-methyl-3-[(3-methyl-2-pentyl-2-cyclopenten-1-yl)oxy]propanal or (±)-5-[(2-pentyl-2-cyclopenten-1-yl)oxy]pentanal.

[0032] According to another particular embodiment of the invention, the compound of formula (I) is (±)-4-[(2-pentyl-2-cyclopenten-1-yl)oxy]butanal.

[0033] When the odor of the compounds of the invention is compared with that of the prior art compound 5-ethoxy-1-pentyl-1-cyclopentene, the compounds of the invention are characterized by their lack of earthy notes characteristic of the prior art compounds themselves. Due to said differences, the compounds according to the invention and the prior art compounds are each suitable for different uses, i.e. they give different organoleptic impressions.

[0034] As mentioned above, the present invention relates to the use of a compound of formula (I) as a perfuming ingredient. In other words, the present invention relates to a method for imparting, enhancing, improving or modifying the odor characteristics of a perfuming composition or a perfumed article or surface, which method comprises adding to said composition or article at least an effective amount of a compound of formula (I), for example imparting its typical note. It is understood that the final pleasant effect may depend on the exact dosage and organoleptic properties of the compound of the present invention, but in any case, the addition of the compound of the present invention imparts to the final product its typical touch in the form of a note, touch or aspect, depending on the dosage.

[0035] With regard to "use of a compound of formula (I)", the use of any composition which comprises compound (I) and which may be advantageously used in the perfumery industry is to be understood here.

[0036] Said composition, which is in fact advantageously used as a perfuming ingredient, is also an object of the present invention.

[0037] Therefore, another object of the present invention is to i) as perfuming ingredient, at least one compound of the invention as defined above, ii) at least one ingredient selected from the group consisting of a perfume carrier and a perfume base; and iii) optionally at least one flavoring adjuvant A fragrance composition comprising:

[0038] By "perfume carrier" is meant herein a material that is practically neutral from the perfume point of view, i.e. does not significantly modify the organoleptic properties of the perfuming ingredients. Said carrier may be liquid or solid.

[0039] The liquid carrier may include, but is not limited to, emulsifying systems, i.e., solvents and surfactant systems, or solvents commonly used in perfumery.A detailed description of the nature and type of solvents commonly used in perfumery cannot be exhaustive.However, the most commonly used solvents include, but are not limited to, butylene or propylene glycol, glycerol, dipropylene glycol and its monoethers, 1,2,3-propanetriyl triacetate, dimethyl glutarate, dimethyl adipate, 1,3-diacetyloxypropan-2-yl acetate, diethyl phthalate, isopropyl myristate, benzyl benzoate, benzyl alcohol, 2-(2-ethoxyethoxy)-1-ethanol, or triethyl citrate, or mixtures thereof. With regard to compositions comprising both a fragrance carrier and a fragrance base, other fragrance carriers which may be suitable than those mentioned above may be ethanol, water / ethanol mixtures, limonene or other terpenes, isoparaffins such as those known under the trade name Isopar® (supplier: Exxon Chemical) or glycol ethers and glycol ether esters such as those known under the trade name Dowanol® (supplier: Dow Chemical Company), or hydrogenated castor oil such as those known under the trade name Cremophor® RH 40 (supplier: BASF).

[0040] Solid carrier is meant to indicate a material capable of chemically or physically binding the perfume composition or some of the components of the perfume composition. Generally, such solid carriers are used to stabilize the composition, to adjust the rate of evaporation of the composition or some of its components. Solid carriers are currently used in the art, and the skilled person knows how to achieve the desired effect. However, with regard to non-limiting examples of solid carriers, they include absorbent gums or polymers or inorganic materials, such as porous polymers, cyclodextrins, wood materials, organic or inorganic gels, clays, gypsum talc or zeolites.

[0041] Other non-limiting examples of solid carriers may include encapsulation materials. Examples of such materials may include wall-forming and plasticizing materials, such as mono-, di- or trisaccharides, natural or modified starches, hydrocolloids, cellulose derivatives, polyvinyl acetate, polyvinyl alcohol, proteins or pectins, or even materials mentioned in references, such as H. Scherz, Hydrokolloide: Stabilisatoren, Dickungs- und Geliermittel in Lebensmitteln, Band 2 der Schriftenreihe Lebensmittelchemie, Lebensmittelqualitaet, Behr's Verlag GmbH & Co., Hamburg, 1996. Encapsulation is a method well known to those skilled in the art and may be carried out by using techniques such as spray drying, coagulation or even extrusion, or may consist of coating encapsulation, including coacervation and complex coacervation techniques.

[0042] Non-limiting examples of solid carriers may include core-shell capsules with aminoplast, polyamide, polyester, polyurea or polyurethane type resins or mixtures thereof (all of the aforementioned resins are well known to those skilled in the art) using techniques such as phase separation processes induced by polymerization, by interfacial polymerization, by coacervation, or all of the aforementioned techniques (all of the aforementioned techniques are described in the prior art), optionally in the presence of polymeric stabilizers or cationic copolymers.

[0043] The resins may be prepared by polycondensation of aldehydes (e.g., formaldehyde, 2,2-dimethoxyethanol, glyoxal, glyoxylic acid or glycolaldehyde and mixtures thereof) with amines, such as urea, benzoguanamine, glycoluril, melamine, methylolmelamine, methylated methylolmelamine, guanazole, etc., and mixtures thereof. Alternatively, preformed resins, alkylated polyamines, such as those commercially available under the trade names Urac® (supplied by Cytec Technology Corp.), Cymel® (supplied by Cytec Technology Corp.), Urecoll® or Luracoll® (supplied by BASF) may be used.

[0044] Other resins are preferably prepared by polycondensation of a polyol, such as glycerol, and a polyisocyanate, such as the trimer of hexamethylene diisocyanate, the trimer of isophorone diisocyanate, or xylylene diisocyanate, or the biuret of hexamethylene diisocyanate, or the trimer of xylylene diisocyanate with trimethylolpropane (known under the trade name Takenate®, supplier: Mitsui Chemicals), preferably the trimer of xylylene diisocyanate with trimethylolpropane and the biuret of hexamethylene diisocyanate.

[0045] Some of the productive literature on the encapsulation of perfumes by polycondensation of amino resins, i.e. melamine-based resins with aldehydes, includes those published by K. Dietrich et al. in Acta Polymerica (1989, Vol. 40, pp. 243, 325 and 683, and 1990, Vol. 41, pp. 91). Such literature already describes the various parameters that affect the production of such core-shell microcapsules, according to the prior art methods that are explained in more detail and exemplified in the patent literature. US 4'396'670 (Wiggins Teape Group Limited) is a suitable early example of such literature. Since then, many other authors have enriched the literature in this field, and although it is not possible to cover here all the developments that have been published, a general knowledge of encapsulation techniques is very important. Representative recent relevant literature disclosing suitable uses of such microcapsules is, for example, provided by K. Bruyninckx and M. Dusselier (ACS Sustainable Chemistry & Engineering, 2019, vol. 7, pages 8041-8054).

[0046] By "perfume base" is meant herein a composition comprising at least one perfuming co-ingredient.

[0047] Said perfuming co-ingredient is not of formula (I).Furthermore, by "perfuming co-ingredient", in this specification, it means a compound that is used in perfuming preparation or composition to give pleasant effect.In other words, it must be recognized by those skilled in the art that such co-ingredient should be considered as perfuming co-ingredient, and can give or modify the odor of composition in a positive or favorable way, and not just have one odor.

[0048] The nature and type of perfuming co-ingredients present in said base, which in any case will not be exhaustive, do not warrant a more detailed description here, whereby a person skilled in the art can select said base on the basis of his general knowledge and according to any use or application and the organoleptic effect desired. In general terms, these perfuming co-ingredients belong to various chemical classes: alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogen or sulfur heterocyclic compounds and essential oils, and said perfuming co-ingredients may be of natural or synthetic origin.

[0049] Mention may in particular be made of perfuming co-ingredients known for having similar olfactory notes, such as: Mention may in particular be made of the perfuming co-ingredients customarily used in perfume formulations, such as: - aldehyde components: decanal, dodecanal, 2-methyl-undecanal, 10-undecanal, octanal, nonanal and / or nonenal; - aromatic herbal ingredients: eucalyptus oil, camphor, eucalyptol, 5-methyltricyclo[6.2.1.0~2,7~]undecane-4-one, 1-methoxy-3-hexanethiol, 2-ethyl-4,4-dimethyl-1,3-oxathiane, 2,2,7 / 8,9 / 10-tetramethylspiro[5.5]undec-8-en-1-one, menthol and / or alpha-pinene; - Balsam components: coumarin, ethyl vanillin and / or vanillin; - citrus constituents, dihydromyricenol, citral, orange oil, linalyl acetate, citronellyl nitrile, orange terpenes, limonene, 1-p-menthen-8-yl acetate and / or 1,4(8)-p-menthadiene; - Floral Ingredients: Methyl Dihydrojasmonate, Linalool, Citronellol, Phenylethanol, 3-(4-tert-butylphenyl)-2-methylpropanal, Hexyl Cinnamaldehyde, Benzyl Acetate, Benzyl Salicylate, Tetrahydro-2-isobutyl-4-methyl-4(2H)-pyranol, Beta-Ionone, Methyl 2-(Methylamino)benzoate, (E)-3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one, (1E)-1-(2,6,6-trimethyl-2- cyclohexen-1-yl)-1-penten-3-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one, (2E)-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-buten-1-one, (2E)-1-[2,6,6-trimethyl-3-cyclohexen-1-yl]-2-buten-1-one, (2E)-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-buten-1-one, 2,5-dimethyl-2-indanmethanol, 2,6,6-trimethyl-3-cyclohexen Cyclohexene-1-carboxylate, 3-(4,4-dimethyl-1-cyclohexen-1-yl)propanal, hexyl salicylate, 3,7-dimethyl-1,6-nonadien-3-ol, 3-(4-isopropylphenyl)-2-methylpropanal, vergyl acetate, geraniol, p-mentha-1-en-8-ol, 4-(1,1-dimethylethyl)-1-cyclohexyl acetate, 1,1-dimethyl-2-phenylethyl acetate, 4-cyclohexyl-2-methyl-2-butanol, amyl salicylate, high cis-methyl dihydroxide Rojasmonate, 3-methyl-5-phenyl-1-pentanol, virgyl propionate, geranyl acetate, tetrahydrolinalool, cis-7-P-methanol, propyl (S)-2-(1,1-dimethylpropoxy)propanoate, 2-methoxynaphthalene, 2,2,2-trichloro-1-phenylethyl acetate, 4 / 3-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carbaldehyde, amylcinnamaldehyde, 8-decen-5-olide, 4-phenyl-2-butanone, isononyl acetate, 4-(1,1-dimethylethyl)-1-cyclohexyl acetate, vergyl isobutyrate and / or a mixture of methyl ionone isomers; - fruity ingredients: gamma-undecalactone, 2,2,5-trimethyl-5-pentylcyclopentanone, 2-methyl-4-propyl-1,3-oxathiane, 4-decanolide, ethyl 2-methyl-pentanoate, hexyl acetate, ethyl 2-methylbutanoate, gamma-nonalactone, allylheptanoate, 2-phenoxyethyl isobutyrate, ethyl 2-methyl-1,3-dioxolane-2-acetate, 3-(3,3 / 1,1-dimethyl-5-indanyl)propanal, diethyl 1,4-cyclohexanedicarboxylate, 3-methyl-2-hexen-1-yl acetate, 1-[3,3-dimethylcyclohexyl]ethyl[3-ethyl-2-oxiranyl]acetate and / or diethyl 1,4-cyclohexanedicarboxylate; - green ingredients: 2-methyl-3-hexanone (E)-oxime, 2,4-dimethyl-3-cyclohexene-1-carbaldehyde, 2-tert-butyl-1-cyclohexyl acetate, styrallyl acetate, allyl (2-methylbutoxy)acetate, 4-methyl-3-decen-5-ol, diphenyl ether, (Z)-3-hexen-1-ol and / or 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one; - Musk ingredients: 1,4-dioxa-5,17-cycloheptadecanedione, (Z)-4-cyclopentadecen-1-one, 3-methylcyclopentadecanone, 1-oxa-12-cyclohexadecen-2-one, 1-oxa-13-cyclohexadecen-2-one, (9Z)-9-cycloheptadecen-1-one, 2-{1S)-1-[(1R)-3,3-dimethylcyclohexyl]ethoxy}-2-oxaethylpropionate, 3-methyl-5-cyclopentadecanone entadecen-1-one, 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethyl-cyclopenta-g-2-benzopyran, (1S,1'R)-2-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxy]-2-methylpropylpropanoate, oxacyclohexadecan-2-one and / or (1S,1'R)-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxycarbonyl]methylpropanoate; - Woody Ingredients: 1-[(1RS,6SR)-2,2,6-trimethylcyclohexyl]-3-hexanol, 3,3-dimethyl-5-[(1R)-2,2,3-trimethyl-3-cyclopenten-1-yl]-4-penten-2-ol, 3,4'-dimethylspiro[oxirane-2,9'-tricyclo[6.2.1.02,7]undec[4]ene, (1-ethoxyethoxy)cyclododecane, 2,2,9,11-tetramethylspiro[5.5]undec-8-en-1-yl acetate, 1-(octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-1-ethanone, patchouli oil, Terpene fraction of patchouli oil, clearwood®, (1'R,E)-2-ethyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-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-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-yl)ethan-1-one and / or isobornyl acetate; other ingredients (e.g. amber, powdery spicy or watery): dodecahydro-3a,6,6,9a-tetramethyl-naphtho[2,1-b]furan and any of its stereoisomers, heliotropin, anisaldehyde, eugenol, cinnamaldehyde, clove oil, 3-(1,3-benzodioxol-5-yl)-2-methylpropanal, 7-methyl-2H-1,5-benzodioxepin-3(4H)-one, 2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydro-2-naphthalenol, 1-phenylvinyl acetate, 6-methyl-7-oxa-1-thia-4-azaspiro[4.4]nonane and / or 3-(3-isopropyl-1-phenyl)butanal.

[0050] The perfume base according to the invention may be, but is not limited to, the perfuming co-ingredients mentioned above, many of which are in any case mentioned in references, for example in Perfume and Flavor Chemicals, 1969, by S. Arctander, Montclair, New Jersey, USA, or its latest editions, 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 said co-ingredients may be compounds known to release various types of perfuming compounds in a controlled manner, also known as properfumes or profragrances. Non-limiting examples of suitable propurfumes may include 4-(dodecylthio)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-butanone, 4-(dodecylthio)-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butanone, trans-3-(dodecylthio)-1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-1-butanone, 2-phenylethyloxo(phenyl)acetate, or mixtures thereof.

[0051] According to a particular embodiment, the compound of the present invention comprises methyl dihydrojasmonate.

[0052] By "perfuming adjuvant" is meant here an ingredient capable of imparting additional added effects, such as color, specific light resistance, chemical stability, etc. A detailed description of the nature and type of adjuvants customarily used in perfumed compositions cannot be exhaustive, but it should be mentioned that said ingredients are well known to the skilled artisan. As specific, non-limiting examples, one may mention: viscosity agents (e.g. surfactants, thickeners, gelling and / or rheology modifiers), stabilizers (e.g. preservatives, antioxidants, heat / light and / or buffers or chelating agents, e.g. BHT), colorants (e.g. dyes and / or pigments), preservatives (e.g. antibacterial or antimicrobial or antifungal or anti-irritant agents), abrasives, skin cooling agents, fixatives, insect repellents, ointments, vitamins and mixtures thereof.

[0053] It is understood that a person skilled in the art is perfectly capable of designing the optimum formulation for the desired effect by mixing said components of the perfuming composition, simply by applying standard knowledge in the art and by trial and error methodology.

[0054] The compositions of the present invention consisting of at least one compound of formula (I) and at least one perfume carrier are particular embodiments of the present invention, as well as perfumed compositions comprising at least one compound of formula (I), at least one perfume carrier, at least one perfume base, and optionally at least one perfume adjuvant.

[0055] According to a particular embodiment, said compositions comprise one or more compounds of formula (I) and allow the perfumer to produce accords or perfumes that exhibit the odour notes of the various compounds of the invention, thus creating new building blocks for the purpose of their production.

[0056] For reasons of clarity, it is also understood that any mixture obtained directly from a chemical synthesis, containing the compound of the invention as a starting, intermediate or final product, such as a reaction medium without sufficient purification, is not considered as a perfuming composition according to the invention, as long as said mixture provides the compound according to the invention in a form suitable for perfuming. Unpurified reaction mixtures are therefore generally excluded from the present invention, unless expressly stated otherwise.

[0057] The compounds of the invention may be advantageously used in all fields of modern perfumery, i.e. fine perfumery or functional perfumery, to positively impart or improve the odor of consumer products to which said (I) is added. Another object of the invention therefore consists in perfumed consumer products comprising, as perfuming ingredient, at least one compound of formula (I) as defined above.

[0058] The compounds of the invention can be added as such or as part of a perfuming composition according to the invention.

[0059] For reasons of clarity, "perfumed consumer product" is meant to indicate a consumer product that provides at least one pleasant odor effect to the surface or space to which the odor effect is applied (e.g. skin, hair, fabric, or home surface).In other words, the odorized consumer product according to the present invention is a odorized consumer product that comprises a functional preparation and optionally additional active substances corresponding to the desired consumer product, and an olfactory effective amount of at least one compound according to the present invention.For reasons of clarity, said odorized consumer product is a non-edible product.

[0060] The nature and type of ingredients of the perfumed consumer product, which in any case will not be exhaustive, does not warrant a more detailed description here, whereby a person skilled in the art can select the nature and type of ingredients of the perfumed consumer product on the basis of his general knowledge and according to the nature of the product and the desired effect.

[0061] Non-limiting examples of suitable perfumed consumer products include fragrances, such as fine perfumes, splashes or eau de parfums, colognes or shave or aftershave lotions; fabric care products, such as liquid or solid detergents, fabric softeners, liquid or solid scent boosters, fabric refreshers, ironing waters, paper, bleach, carpet cleaners, curtain care products; body care products, such as hair care products (e.g. shampoos, hair dyes or hair sprays, colour care products, hair shaping products), dental care products, disinfectants, intimate care products; cosmetic formulations (e.g. skin creams or lotions, vanishing creams or deodorants or antiperspirants (e.g. sprays or roll-ons), hair removal products, hair care ... products, tanning or after-sun products, nail products, skin cleansing, make-up); or skin care products (perfumed soaps, mousses, oils or gels for the shower or bath, or hygiene products, or foot / hand care products); air care products, such as air fresheners or "ready to use" powdered air fresheners that may be used in residential spaces (rooms, refrigerators, cupboards, shoeboxes or cars) and / or in public spaces (hall, hotel, mall, etc.); or home care products, such as mould removers, furnisher care products, wipes, dish detergents or hard surface (e.g. floor, bath, sanitary or window washing) detergents; leather care products; car care products, such as polishes, waxes or plastic cleaners.

[0062] Some of said perfumed consumer products may be aggressive media for the compounds of the invention, and therefore may need to be protected against premature degradation against suitable external stimuli, such as enzymes, light, heat or changes in pH, for example by encapsulation or by chemical bonding with other chemicals suitable for the release of the ingredients of the invention.

[0063] The proportions of the compounds according to the invention that may be incorporated into the various products or compositions vary in a wide range of values, depending on the nature of the article to be perfumed, as well as on the desired organoleptic effect and the nature of the co-ingredients in a given base, when the compounds according to the invention are mixed with the perfuming co-ingredients, solvents or additives commonly used in the prior art.

[0064] For example, in the case of perfumed compositions, typical concentrations range from 0.001% to 20% by weight or more of the compound of the invention relative to the weight of the composition in which it may be incorporated.In the case of perfumed consumer products, typical concentrations range from 0.0001% to 5% by weight or more of the compound of the invention relative to the weight of the composition in which it may be incorporated.

[0065] The compounds according to the invention can be prepared by the methods described in the following examples, i.e. by hydroformylation of the double bond, for example using synthesis gas CO / H2. Depending on the method of preparing the compounds of the invention by hydroformylation, CO can be attached to either one of the two carbons of the double bond. This will lead to a mixture of different positional isomers, which means that a mixture of linear or branched hydroformylation products can be obtained.

[0066] By using the process for preparing the compounds of the present invention by hydroformylation, a mixture of double bond linear or branched hydroformylation products can be obtained. In certain embodiments, the following specific products can be obtained: [ka] The mixture of compounds can be obtained in a ratio of 99:1 to 40:60, preferably 95:5 to 60:40 or 90:10 to 70:30 (i.e. corresponding to the ratio of linear hydroformylation product:branched hydroformylation product). Mixtures of linear and branched hydroformylation products can also be used as perfuming ingredients according to the invention.

[0067] Working Example The invention is described in further detail by the following examples, in which the abbreviations have their usual meaning in the art and the temperatures are given in degrees Celsius (° C.). NMR spectra were obtained at 400 MHz ( 1 H) and 100MHz ( 13 C) operating on a Bruker Avance II Ultrashield 400plus or 500MHz ( 1 H) and 125MHz ( 13 C) operated by Bruker Avance III500 or 600MHz ( 1 H) and 150MHz ( 13 C), and the spectra were internally referenced to tetramethylsilane at 0.0 ppm. 1 H NMR signal shifts are expressed in δ ppm and coupling constants (J) are expressed in Hz with the following multiplicities: d, doublet; t, triplet; q, quartet; m, multiplet; b, broad (indicating unresolved couplings) and were interpreted using Bruker Topspin software. 13 C NMR data are expressed as chemical shifts δ ppm and hybridization from DEPT90 and DEPT135 experiments, C, quaternary; CH, methine; CH2, methylene; CH3, methyl.

[0068] Example 1 Synthesis of compounds of formula (I) a) Formation of (±)-4-[(2-pentyl-2-cyclopenten-1-yl)oxy]butanal Step 1: Synthesis of (±)-5-allyloxy-1-pentyl-1-cyclopentene (±)-2-Pentyl-2-cyclopenten-1-ol (40 g; 259 mmol) was dissolved in dry THF (0.3 L) under nitrogen and the solution was cooled in an ice-water bath. Solid potassium t-butoxide (36 g; 311 mmol) was added in one portion. After 10 min, the cooling bath was removed and the reaction was stirred for 1.5 h. The reaction was cooled in an ice-water bath. Tetrabutylammonium iodide (5.75 g; 15.6 mmol) was added, followed 10 min later by allyl chloride (59.5 g; 778 mmol) over 2 h. The reaction was allowed to warm to RT and stirred overnight. It was then quenched with saturated NH4Cl and extracted twice with diethyl ether. The extracts were washed with brine, dried over sodium sulfate and concentrated on a rotavapor. The product was purified by column chromatography on silica gel (elution: heptane / ethyl acetate 19:1) followed by bulb-to-bulb distillation (60 °C / 1 mbar) to give (±)-5-allyloxy-1-pentyl-1-cyclopentene as a colorless liquid (38.6 g; 199 mmol; 77%).

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[0069] Step 2: Hydroformylation of (±)-5-allyloxy-1-pentyl-1-cyclopentene (±)-5-Allyloxy-1-pentyl-1-cyclopentene (10 g; 51 mmol) was dissolved in toluene (60 ml) and stirred in a stainless steel autoclave under 50 bar H2 / CO (55:45; syngas) in the presence of [HRh(CO)(PPH3)3] (20 mg; 0.022 mmol) and triphenylphosphine (87 mg; 0.332 mmol) at 90 °C for 2 h. The reaction was concentrated on a rotavapor and the crude material was directly purified by column chromatography on silica gel (elution: heptane / ethyl acetate 19:1 to 9:1) followed by bulb-to-bulb distillation (85 °C / 0.03 mbar) to give (±)-4-[(2-pentyl-2-cyclopenten-1-yl)oxy]butanal as a colourless liquid (5.5 g; 24 mmol; 47%).

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[0070] b) Formation of (±)-2-methyl-3-[(3-methyl-2-pentylcyclopent-2-en-1-yl)oxy]propanal Using the same reaction sequence as described in Example 1a), (±)-3-hydroxy-1-methyl-2-pentylcyclopent-1-ene was converted to (±)-2-methyl-3-[(3-methyl-2-pentylcyclopent-2-en-1-yl)oxy]propanal. The product was obtained as a mixture of diastereomers after column chromatography on silica gel (elution: heptane / ethyl acetate 19:1) followed by bulb-to-bulb distillation (75° C. / 0.01 mbar).

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[0071] c) Formation of (±)-4-[(2-isopentylcyclopent-2-en-1-yl)oxy]butanal Using the same reaction sequence as described in Example 1a), (±)-5-hydroxy-1-isopentyl-cyclopent-1-ene was converted to (±)-4-[(2-isopentylcyclopent-2-en-1-yl)oxy]butanal. The product was purified by column chromatography on silica gel (elution: heptane / ethyl acetate 19:1 to 4:1) followed by bulb-to-bulb distillation (85° C. / 0.05 mbar).

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[0072] d) Formation of (±)-5-[(2-pentylcyclopent-2-en-1-yl)oxy]pentanal (coll. 74013) Step 1: Synthesis of (±)-5-(but-2-en-1-yloxy)-1-pentylcyclopent-1-ene (±)-5-Hydroxy-1-pentylcyclopent-1-ene (10.5 g; 68 mmol) was dissolved in dry THF (300 ml) under nitrogen and the solution was cooled in an ice-water bath. Solid potassium t-butoxide (9.5 g; 82 mmol) was added in one portion. After 10 min, the cooling bath was removed and the reaction was stirred for 1.5 h. The reaction was cooled in an ice-water bath. n-Bu4NI (1.5 g; 4 mmol) was added followed 10 min later by 1-chlorobut-2-ene (26.4 g; 204 mmol) over 2 h (exothermic reaction). The reaction was allowed to warm to RT and stirred overnight. It was then quenched with saturated NH4Cl and extracted twice with diethyl ether. The extracts were washed with brine, dried over sodium sulfate and concentrated on a rotavapor. The product was purified by bulb-to-bulb distillation (60° C. / 1 mbar) to give (±)-5-(but-2-en-1-yloxy)-1-pentylcyclopent-1-ene as a colorless liquid (7 g; 33 mmol; 48%) and a 70 / 30 mixture of E / Z isomers.

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[0073] Step 2: (±)-5-[(2-pentylcyclopent-2-en-1-yl)oxy]pentanal (±)-5-(but-2-en-1-yloxy)-1-pentyl-1-cyclopentene (6.5 g; 32 mmol) was dissolved in toluene (60 ml) and stirred in a stainless steel autoclave under 50 bar H2 / CO (55:45; syngas) in the presence of [HRh(CO)(PPH3)3] (20 mg; 0.022 mmol) and triphenylphosphine (87 mg; 0.332 mmol) at 90 °C for 4 h. The reaction was concentrated on a rotavapor and the crude material was directly purified twice by column chromatography on silica gel (elution: heptane / ethyl acetate 19:1 to 9:1) followed by bulb-to-bulb distillation (85 °C / 0.03 mbar) to give (±)-5-[(2-pentyl-2-cyclopenten-1-yl)oxy]butanal as a colorless liquid (0.45 g; 1.8 mmol; 6%).

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[0074] Example 2 Preparation of the Perfuming Composition A perfume composition was prepared by mixing the following ingredients: [Table 1-1] [Table 1-2] 1) (-)-(8R)-8,12-epoxy-13,14,15,16-tetranorlabdane; Supplier: Firmenich SA, Geneva, Switzerland 2) 7-Methyl-2H,4H-1,5-benzodioxepin-3-one; Supplier: Firmenich SA, Geneva, Switzerland 3) 1-Oxacyclohexadece-12 / 13-en-2-one; Supplier: Firmenich SA, Geneva, Switzerland 4) Methyl-3-oxo-2-pentylcyclopentaneacetate; Supplier: Firmenich SA, Geneva, Switzerland 5) (1S,1'R)-2-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxy]-2-methylpropylpropanoate; Supplier: Firmenich SA, Geneva, Switzerland 6) 1-(5,5-Dimethyl-1-cyclohexenyl)pent-4-en-1-one; Supplier: Firmenich SA, Geneva, Switzerland 7) (E)-3,3-Dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol; Supplier: Firmenich SA, Geneva, Switzerland 8) Supplier: Firmenich SA, Geneva, Switzerland 9) 3-(4 / 2-ethylphenyl)-2,2-dimethylpropanal; Supplier: International Flavors & Fragrances, USA 10) 1-(Octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-1-ethanone; Supplier: International Flavors & Fragrances, USA 11) [(Z)-Hex-3-enyl]methyl carbonate; Supplier: International Flavors & Fragrances, USA 12) 3-(4-tert-butylphenyl)-2-methylpropanal; Supplier: Givaudan SA, Vernier, Switzerland 13) Allylionone; Supplier: Givaudan SA, Vernier, Switzerland 14) Prop-2-enyl 2-cyclohexyloxyacetate; Supplier: Symrise AG, Holzminden, Germany 15) 3-(1,3-benzodioxol-5-yl)-2-methylpropanal; Supplier: Firmenich SA, Geneva, Switzerland 16) 4-Methyl-3-decen-5-ol; Supplier: Givaudan SA, Vernier, Switzerland 17) Patchouli extract, CAS number 84238-39-1; Supplier: Firmenich SA, Geneva, Switzerland.

[0075] The addition of 1000 parts by weight of (±)-4-[(2-pentyl-2-cyclopenten-1-yl)oxy]butanal to the composition gave it a stronger, fresher, greener, more natural, and more watery connotation. (±)-4-[(2-pentyl-2-cyclopenten-1-yl)oxy]butanol blends particularly well with the floral Hedione, watery Calone, and green (Z)-3-Hexene-1-ol elements.

[0076] When 5-ethoxy-1-pentyl-1-cyclopentene is added instead of the compounds of the present invention, the composition becomes greener, earthier and mustier. 5-ethoxy-1-pentyl-1-cyclopentene brings about a dirty-musty and earthy aspect and does not mix well with other compositions.

[0077] Example 3 Preparation of Liquid Detergents Containing Compounds of the Invention [Table 2] 1) Hostapur SAS 60;Supplier: Clariant 2) Edenor K 12-18;Supplier:Cognis 3) Genapol LA 070;Supplier: Clariant 4) Supplier: Genencor International 5) Aculyn 88; Supplier: Dow Chemical.

[0078] A liquid detergent was prepared by adding 0.5-1.5% by weight of the composition of Example 2 of the present invention, based on the total weight of the liquid detergent, to the unscented liquid detergent formulation of Table 1 with gentle shaking.

[0079] Example 4 Preparation of Fabric Softeners Containing Compounds of the Invention [Table 3] 1) Stepantex VL90 A Diester Quat;Supplier: Stepan 2) Proxel GXL; Supplier: Arch.

[0080] The softener was prepared by weighing methyl bis[ethyl(tallow fatty acid)]-2-hydroxyethyl ammonium methyl sulfate, which was heated at 65°C. Then, water and 1,2-benzisothiazolin-3-one were placed in a reactor and heated at 65°C under stirring. To the mixture, methyl bis[ethyl(tallow fatty acid)]-2-hydroxyethyl ammonium methyl sulfate was added. The mixture was stirred for 15 minutes and CaCl2 was added. Then, 0.5-2% by weight of the composition of Example 2 of the present invention was added, based on the total weight of the softener. The mixture was stirred for 15 minutes and cooled to room temperature under stirring (viscosity measurement: result 35+ / -5 mPas (shear rate 106 sec-1)).

[0081] Example 5 Preparation of a clear isotropic shampoo containing the composition of the present invention [Table 4] 1) Ucare Polymer JR-400, supplier: Noveon 2) Supplier: Schweizerhall 3) Glydant, source: Lonza 4) Texapon NSO IS, Supplier: Cognis 5) Tego Betain F 50, supplier: Evonik 6) Amphotensid GB 2009, supplier: Zschimmer&Schwarz 7) Monomuls 90 L-12, supplier: Gruenau 8) Nipagin Monosodium, supplier: NIPA.

[0082] A shampoo was prepared by dispersing Polyquaternium-10 in water. The remaining ingredients of Phase A were mixed by adding each one in turn with good mixing after each addition. This premix was added to the Polyquaternium-10 dispersion and mixed for an additional 5 minutes. Then, with stirring, premixed Phase B and premixed Phase C were added (Monomuls 90L-12 heated to melt in Texapon NSO IS). With stirring, Phase D and Phase E were added. The pH was adjusted with citric acid solution until pH: 5.5-6.0 to provide an unscented shampoo formulation.

[0083] A fragranced shampoo was formulated by adding 0.4-0.8% by weight of the composition of inventive Example 2, based on the total weight of the shampoo, to the unscented shampoo preparation of Table 3 with gentle shaking.

[0084] Example 6 Preparation of structured shower gels containing the compositions of the present invention [Table 5] 1) EDETA B POWDER; Trademark and Supplier: BASF 2) CARBOPOL AQUA SF-1 POLYMER; Trademark and supplier: NOVEON 3) ZETESOL AO 328 U; Trademark and Supplier: ZSCHIMMER&SCHWARZ 4) TEGO-BETAIN F 50; Brand and Supplier: GOLDSCHMIDT 5) KATHON CG; Trademark and supplier: ROHM&HASS.

[0085] A shower gel was formulated by adding 0.5-1.5% by weight of the composition of inventive example 2, based on the total weight of the shower gel, to the unscented shower gel formulation of Table 4 with gentle shaking.

[0086] Example 7 Preparation of a clear shower gel containing the composition of the present invention [Table 6] 1) EDETA B POWDER; Trademark and Supplier: BASF 2) ZETESOL AO 328 U; Trademark and Supplier: ZSCHIMMER&SCHWARZ 3) TEGO-BETAIN F 50; Brand and Supplier: GOLDSCHMIDT 4) MERQUAT 550; Brand and Supplier: LUBRIZOL.

[0087] A clear shower gel was formulated by adding 0.5-1.5% by weight of the composition of inventive example 2, based on the total weight of the shower gel, to the unscented shower gel formulation of Table 5 with gentle shaking.

[0088] Example 8 Formulation of a milky shower gel containing the composition of the present invention [Table 7] 1) EDETA B POWDER; Trademark and Supplier: BASF 2) Texapon NSO IS; Trademark and Supplier: COGNIS 3) MERQUAT 550; Brand and Supplier: LUBRIZOL 4) DEHYTON AB-30; Trademark and supplier: COGNIS 5) GLUCAMATE LT; Trademark and Supplier: LUBRIZOL 6) EUPERLAN PK 3000 AM; Trademark and supplier: COGNIS 7) CREMOPHOR RH 40; trademark and supplier: BASF.

[0089] A clear shower gel was formulated by adding 0.5-1.5% by weight of the composition of inventive example 2, based on the total weight of the shower gel, to the unscented shower gel formulation of Table 6 with gentle shaking.

[0090] Example 9 Pearlescent Shampoo Formulations Containing the Compositions of the Invention [Table 8] 1) EDETA B Powder, supplier: BASF 2) Jaguar C14 S, supplier: Rhodia 3) Ucare Polymer JR-400, supplier: Noveon 4) Sulfetal LA BE, supplier: Zschimmer&Schwarz 5) Zetesol LA, Supplier: Zschimmer&Schwarz 6) Tego Betain F 50, supplier: Evonik 7) Xiameter MEM-1691, supplier: Dow Corning 8) Lanette 16, supplier: BASF 9) Comperlan 100, Supplier: Cognis 10) Cutina AGS, Supplier: Cognis 11) Kathon CG, supplier: Rohm&Haas 12) D-Panthenol, supplier: Roche.

[0091] A shampoo was prepared by dispersing guar hydroxypropyltrimonium chloride and polyquaternium-10 in water and tetrasodium EDTA. A 10% solution of NaOH (Phase B) was added when Phase A was homogeneous. A 10% solution of NaOH (Phase B) was added when Phase A was homogeneous. The mixture was then heated to 75°C. Phase D ingredients were added and mixed until homogeneous. The mixture was cooled. At 45°C, Phase E was added with mixing. The final viscosity was adjusted with 25% NaCl solution and pH was adjusted to 5.5-6 with 10% NaOH solution.

[0092] A fragranced pearlescent shampoo was formulated by adding 0.4-0.8% by weight of the composition of inventive Example 2, based on the total weight of the shampoo, to the unscented shampoo preparation of Table 7 with gentle shaking.

[0093] Example 10 Preparation of structured shower gels containing the compositions of the present invention [Table 9] 1) EDETA B POWDER; Trademark and Supplier: BASF 2) CARBOPOL AQUA SF-1 POLYMER; Trademark and supplier: NOVEON 3) ZETESOL AO 328 U; Trademark and Supplier: ZSCHIMMER&SCHWARZ 4) TEGO-BETAIN F 50; Brand and Supplier: GOLDSCHMIDT 5) KATHONCG; Trademark and Supplier: ROHM & HASS.

[0094] A clear shower gel was formulated by adding 0.5-1.5% by weight of the composition of inventive example 2, based on the total weight of the shower gel, to the unscented shower gel formulation of Table 8 with gentle shaking.

[0095] Example 11 Formulation of Eau de Toilettes Containing the Compounds of the Invention The eau de toilette was formulated by adding 5-20% by weight of the composition of Example 2 of the present invention, based on the total weight of the eau de toilette, to ethanol with gentle shaking.

Claims

1. Formula (I) 【Chemistry 1】 [In the formula, The dotted lines represent carbon-carbon double bonds. p represents 1 to 3; n represents 0 to 2, R are each independently C 1 ~C 6 represents an alkyl group, R 1 are each independently a hydrogen atom or C 1 ~C 3 represents an alkyl group] 2. Use of the compound of formula (I) in the form of any one of its stereoisomers or a mixture thereof as a perfuming ingredient.

2. The compound (I) is represented by the formula (II) 【Chemistry 2】 [Wherein, p, R and R 1 The use according to claim 1, wherein the compound is of the formula:

3. The compound (I) or compound (II) is represented by the formula (III): 【Chemistry 3】 [In the formula, R 1 The definitions of are the same as those in claim 1, R 2 is C 1 ~C 6 represents an alkyl group, R 3 is a hydrogen atom or C 1 ~C 6 The use according to claim 1 or 2, wherein the compound is of the formula:

4. The compounds (I) to (III) are 10 ~C 16 4. The use according to any one of claims 1 to 3, which is a compound.

5. The use according to any one of claims 1 to 4, wherein the compounds (I) to (III) are (±)-4-[(2-pentyl-2-cyclopenten-1-yl)oxy]butanal.

6. A method for imparting, enhancing, improving or modifying the odour characteristics of a perfumed composition or a perfumed article, comprising: 【Chemistry 4】 [In the formula, The dotted lines represent carbon-carbon double bonds. p represents 1 to 3; n represents 0 to 2, R are each independently C 1 ~C 6 represents an alkyl group, R 1 are each independently a hydrogen atom or C 1 ~C 3 represents an alkyl group] in the form of any one of its stereoisomers or a mixture thereof.

7. Formula (I) 【Chemistry 5】 [In the formula, The dotted lines represent carbon-carbon double bonds. p represents 1 to 3; n represents 0 to 2, R are each independently C 1 ~C 6 represents an alkyl group, R 1 are each independently a hydrogen atom or C 1 ~C 3 represents an alkyl group] in the form of any one of its stereoisomers or a mixture thereof.

8. below, i) at least one compound of formula (I) according to any one of claims 1 to 6, ii) at least one component selected from the group consisting of a perfume carrier and a perfume base; and iii) optionally at least one perfume adjuvant; A fragrance composition comprising:

9. A perfumed consumer product comprising at least one compound of formula (I) as defined in any one of claims 1 to 6, or a perfumed composition as defined in claim 8.

10. 10. The perfumed consumer product of claim 9, wherein the perfumed consumer product base 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.

11. 11. The perfumed consumer product of claim 10, wherein the perfumed consumer product is a fine perfume, a splash or eau de perfume, a cologne, a shave or after shave lotion, a liquid or solid detergent, a fabric softener, a fabric refresher, an ironing water, paper, a bleach, a carpet cleaner, a curtain care product, a shampoo, a hair dye, a color care product, a hair shaping product, a dental care product, a disinfectant, an intimate care product, a hairspray, a vanishing cream, a deodorant or antiperspirant, a depilatory product, a tanning product, a nail product, a skin cleansing product, a make-up, a perfumed soap, a shower or bath mousse, an oil or gel, or a foot / hand care product, a hygiene product, an air freshener, a "ready to use" powdered air freshener, a mould remover, a furnisher care, a wipe, a dish detergent or a hard surface cleaner, a leather care product, a car care product.

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