Oximes for use in the field of perfumes and fragrances

Abstract

The present invention relates to new oximes of formula (I) for the use in the field of perfumes and fragrances. (I) These oximes of the formula (I) have a particular characteristic olfactory note of figs.5

Description

[0001] OXIMES FOR USE IN THE FIELD OF PERFUMES AND FRAGRANCES

[0002] Technical Field

[0003] The present invention relates to the field of oximes and to the field of perfumery ingredients.

[0004] Background of the invention

[0005] Certain oximes are known to be useful ingredients as fragrance or flavour materials.

[0006] A specific note which is highly desired is the note of figs and fig leaves for perfumes or fragrances.

[0007] WO 2019 / 076926 A1 discloses a broad range of oximes useful as ingredients as fragrance or flavour materials which provide cassis, catty, tropical, green, coniferous, thuya, floral, and / or fruity olfactory notes.

[0008] US 3,637,533 discloses a variety of oximes of aldehydes and ketones having 7 to 10 carbon atoms with a variety of different smells. It discloses 3- methylheptan-5-one oxime (=5-methylheptan-3-one oxime) to have an intense green-leaf odor quite suggestive of crushed fig leaves.

[0009] Summary of the invention

[0010] Therefore, the problem to be solved by the present invention is to offer new chemical compounds providing olfactory sensation of fig and fig leaves.

[0011] Surprisingly, it has been found that a new class of chemicals according to the formula (I) of claim 1 offers a solution to this problem.

[0012] Particularly, it has been surprisingly found that all compounds of the formula (I) have in common that they exhibit at least one methyl group at each of the 2 carbon atoms at the alpha position to the oxime functional group.

[0013] The compounds of the formula (I) have all rather strong fig or fig leave odor and are particularly well suited to their use in perfumes and perfume containing compositions. Their property of having a linear base note even increases their attractivity for being used in the field of perfumery and fragrances.

[0014] Surprisingly, the compounds of formula (I) have a structure which is significantly different from the structure of 5-methylheptan-3-one oxime and found to be at least a very suitable alternative or have even improved properties to 5- methylheptan-3-one oxime. In contrast to 5-methylheptan-3-one oxime, the compounds of the formula (I) exhibit very advantageous base note properties. Particularly, 3,3,5-trimethyloctan-4-one oxime shows a very unique fresh and natural fig odor.

[0015] Further aspects of the invention are subject of further independent claims. Particularly preferred embodiments are subject of dependent claims.

[0016] Detailed description of the invention

[0017] In a first aspect the present invention relates to a compound of the formula (I)

[0018] R1represents either H or CH3; and

[0019] R2represents either a methyl or an ethyl group or a CH=CH2 group, or any stereoisomer thereof; and the wavy line represents a nitrogen-oxygen bond which is either in the Z- or in the E-configuration.

[0020] For sake of clarity, some terms used in the present document are defined as follows:

[0021] In the present document, a “Cx-y-alkyl” group is an alkyl group comprising x to y carbon atoms, i.e. , for example, a Ci-3-alkyl group is an alkyl group comprising 1 to 3 carbon atoms. The alkyl group can be linear or branched. For example -CH(CH3)-CH2-CH3 is considered as a C4-alkyl group. In case identical labels for symbols or groups are present in several formulae, in the present document, the definition of said group or symbol made in the context of one specific formula applies also to other formulae which comprises the same said label.

[0022] The term “independently from each other” in this document means, in the context of substituents, moieties, or groups, that identically designated substituents, moieties, or groups can occur simultaneously with a different meaning in the same molecule.

[0023] Any single dotted line in any formulae represents the bond by which said substituent is bound to the rest of a molecule.

[0024] Any wavy line in any formula of this document represents a nitrogenoxygen bond and which when linked to the carbon- nitrogen double bond is either in the Z or in the E-configuration.

[0025] The term "stereoisomer" is a general term used for all isomers of individual compounds that differ only in the orientation of their atoms in space, not in the connectivity of the atoms Thus, the term stereoisomer includes mirror image isomers (enantiomers), geometric (cis / trans or E / Z) isomers, and diastereoisomers. For precise definitions of the terms, see G. Helmchen:"Vocabulary and Nomenclature of Organic Stereochemistry", in Houben-Weyl E21a, Stereoselective Synthesis G. Helmchen, R.W. Hoffmann, J. Mulzer, E. Schaumann (Hrsg.), 1995, 1-74. The possible isomers can be present either in pure isomeric form or as mixtures (i.e. racemates, cis / trans-mixtures or mixtures of diasteroisomers).

[0026] The term “strong base” in this document means that the base has a pkb of less than 3, particularly of less than 1 . As the person skilled in the art the pkb is related to the pkaof the respective conjugated acid by the relation pkb = 14-pka.

[0027] The compound of formula (I) has a carbon center of chirality which is marked in formula below by * With the exception of R1and / or R2CH3 being methyl, the carbon marked below by *’ is an additional center of chirality.

[0028] The configuration at said centers of chirality is independently from each other either S or R.

[0029] So any combinations of these configurations RR, SR, RS and SR as individual molecules as well mixtures thereof is understood to be covered by these formulae.

[0030] It is preferred that the formula (I) has 9 to 11 carbon atoms, preferably 10 to 11 carbon atoms, most preferably 11 carbon atoms.

[0031] It is further preferred that the compound of the formula (I) is selected from the group consisting of the compounds of the formula (l-A), (l-B), (l-C), (l-D) and (l-E) Particularly preferred as compound of the formula (I) is the compound of the formula (l-B).

[0032] Said compounds of the formula (I) according to the invention have all a particular strong and typical odor of fig in the top note. Particularly the compound of the formula (l-B) (3,3,5-trimethyloctan-4-one oxime) shows a very strong and natural fig odor in the top note and gives a very pleasant and appealing overall olfactory sensation representing an excellent alternative to 5-methylheptan-3-one oxime. Furthermore, it has been found that the compounds of formula (I) show a linear base note, which is very positive for its applications in perfumery.

[0033] In a further aspect, the invention relates to a process of manufacturing a compound of the formula (I) according to any of the preceding claims by reacting a or any stereoisomer thereof; wherein

[0034] R1represents either H or CH3; and

[0035] R2represents either a methyl or an ethyl group or a CH=CH3 group; with a hydroxylamine or hydroxylamine salt or a masked hydroxylamine in the presence of a base, particularly of an amine.

[0036] The formation of the compound of the formula (I) is performed using hydroxylamine or hydroxylamine salt or a masked hydroxylamine in the presence of a base. Suitable bases, particularly for the use of hydroxylamine or hydroxylamine salts, are for example sodium acetate, sodium carbonate, potassium hydroxide, ammonium acetate, imidazole, pyridine or triethyl amine. The base is preferably an amine, more preferably an aromatic amine, most preferably pyridine. When a masked hydroxylamine, particularly N, O-bis(trimethylsilyl)- hydroxylamine, is used, it is preferred to us a strong base, particularly potassium hydride, potassium bis(trimethylsilyl)amide (commonly abbreviated as KHMDS) as base.

[0037] Hydroxylamine hydrochloride is a particular preferred hydroxylamine salt.

[0038] It is obvious that the substituents R1and R2selected for the compound of the formula (II) are the same as for the compound of the formula (I).

[0039] The reaction between the ketone of the formula (II) with hydroxylamine or hydroxylamine salt or masked hydroxylamine in the presence of a base, particularly an amine, is preferably performed at a temperature of between 40 and 200°C, preferably between 50 and 150°C.

[0040] In case a strong base is used for said reaction, it is preferred to perform said reaction at a temperature below 0°C, particularly between -100°C and -20°C.

[0041] The reaction is preferred to be performed at ambient pressure (1013 hPa).

[0042] The molar ratio of the compound of the formula (II) : hydroxylamine or hydroxylamine salt or masked hydroxylamine is preferably in the range of 1 :1.5 to 1 : 50, particularly of 1 : 1 .6 to 10, more preferably of 1 : 1 .8 to 1 :4, most preferably of 1 :2 to 1 :3.

[0043] It is further preferred that the molar ratio of the compound of the formula (II) : base is in the range of 1 : 1 .5 to 1 :30.

[0044] In case of using a strong base, said range is more preferred to be in the range of 1 :1.5 to 1 :6, most preferred of 1 :1.5 to 1 :3.

[0045] In case of using hydroxylamine or hydroxylamine salts, said range is more preferred to be in the range of 1 : 5 to 1 :20, most preferred of 1 : 10 to 1 : 15.

[0046] The reaction is preferably performed in an organic solvent. For the use of strong bases aprotic solvents, particularly tetrahydrofuran (THF), is preferred for said reaction. In case of using a base which is not a strong base, it is preferred to use alcoholic solvents, more preferably methanol or ethanol, most preferably ethanol.

[0047] The volume ratio of base : solvent is preferably in the range of 1 :1.2 to 1 :10. In case of an amine as base said volume ratio is more preferred in the range of 1 :1.5 to 1 :5, most preferred in the range of 1 :1.5 to 1 :4.

[0048] As pointed above, the compounds of the formula (I) have distinct olfactory notes of natural fig and fig leaves and offer a good alternative to 5-methylheptan- 3-one oxime.

[0049] Consequently, these compounds are very attractive to be used in the field of fragrance and perfumes.

[0050] Therefore, in a further aspect, the present invention relates to a composition comprising at least a compound of the formula(l) as discussed above in great detail.

[0051] In a preferred embodiment, said composition is a perfume or fragrance composition.

[0052] Therefore, in a further embodiment, the present invention relates to a perfuming composition comprising i) at least the compound of formula (I) as defined above; ii) at least one ingredient selected from the group consisting of a perfumery carrier and a perfumery base; and iii) optionally at least one perfumery adjuvant.

[0053] By “perfumery carrier” it is meant here a material which is practically neutral from a perfumery point of view, i.e. that does not significantly alter the organoleptic properties of perfuming ingredients. Said carrier may be a liquid or a solid.

[0054] As liquid carrier one may cite, as non-limiting examples, an emulsifying system, i.e. a solvent and a surfactant system, or a solvent commonly used in perfumery. A detailed description of the nature and type of solvents commonly used in perfumery cannot be exhaustive. However, one can cite as non-limiting examples, solvents such as butylene or propylene glycol, glycerol, dipropyleneglycol and its monoethers, 1 ,2,3-propanetriyl triacetate, dimethyl glutarate, dimethyl adipate 1 ,3-diacetyloxypropan-2-yl acetate, diethyl phthalate, isopropyl myristate, Abalyn® (rosin resins, available from DRT), benzyl benzoate, benzyl alcohol, 2-(2-ethoxyethoxy)-1 -ethanol, tri-ethyl citrate or mixtures thereof, which are the most commonly used or also naturally derived solvents like glycerol or various vegetable oils such as palm oil, sunflower oil or linseed oil. For the compositions which comprise both a perfumery carrier and a perfumery base, other suitable perfumery carriers than those previously specified, can be also ethanol, water / ethanol mixtures, limonene or other terpenes, isoparaffins such as those known under the trademark Isopar® (origin: Exxon Chemical) or glycol ethers and glycol ether esters such as those known under the trademark Dowanol® (origin: Dow Chemical Company), or hydrogenated castors oils such as those known under the trademark Cremophor® RH 40 (origin: BASF).

[0055] As solid carrier is meant to designate a material to which the perfuming composition or some element of the perfuming composition can be chemically or physically bound. In general, such solid carriers are employed either to stabilize the composition, or to control the rate of evaporation of the compositions or of some ingredients. Solid carriers are of current use in the art and a person skilled in the art knows how to reach the desired effect. However, by way of non-limiting examples of solid carriers, one may cite absorbing gums or polymers or inorganic materials, such as porous polymers, cyclodextrins, dextrins, maltodextrins wood based materials, organic or inorganic gels, clays, gypsum, calcium carbonate, silicon dioxide, talc or zeolites.

[0056] As other non-limiting examples of solid carriers, one may cite encapsulating materials. Examples of such materials may comprise wall-forming and plasticizing materials, such as glucose syrups, natural or modified starches, hydrocolloids, cellulose derivatives, polyvinyl acetates, polyvinyl alcohols, proteins or pectins, plant gums such as acacia gum (Gum Arabic), urea, sodium chloride, sodium sulfate, sodium carbonate, sodium bicarbonate, calcium carbonate, magnesium sulfate, calcium sulfate, magnesium oxide, zinc oxide, titanium dioxide, calcium chloride, potassium chloride, magnesium chloride, zinc chloride, carbohydrates, saccharides such as sucrose, mono-, di-, tri- and polysaccharides and derivatives such as chitosan, starch, cellulose, carboxymethyl methylcellulose, methylcellulose, hydroxyethyl cellulose, ethyl cellulose, propyl cellulose, polyols / sugar alcohols such as sorbitol, maltitol, xylitol, erythritol, and isomalt, polyethylene glycol (PEG), polyvinyl pyrrolidone (PVP), polyvinyl alcohol, acrylamides, acrylates, polyacrylic acid and related structures, maleic anhydride copolymers, amine-functional polymers, vinyl ethers, styrenes, polystyrenesulfonates, vinyl acids, ethylene glycol-propylene glycol block copolymers, pectins, xanthanes, alginates, carragenans, citric acid or any water soluble solid acid, fatty alcohols or fatty acids and mixtures thereof.

[0057] The encapsulation is a well-known process to a person skilled in the art, and may be performed, for instance, by using techniques such as spray-drying, agglomeration or yet extrusion; or consists of a coating encapsulation, including coacervation and complex coacervation techniques.

[0058] As non-limiting examples of solid carriers, one may cite in particular the core-shell capsules with resins of am inoplast, polyamide, polyester, polyurea or polyurethane type or a mixture thereof (all of said resins are well known to a person skilled in the art) using techniques like phase separation process induced by polymerization, interfacial polymerization, coacervation or altogether (all of said techniques have been described in the prior art), optionally in the presence of a polymeric stabilizer or of a cationic copolymer.

[0059] Resins may be produced by the polycondensation of an aldehyde (e.g. formaldehyde, 2,2-dimethoxyethanal, glyoxal, glyoxylic acid or glycolaldehyde and mixtures thereof) with an amine such as urea, benzoguanamine, glycoluril, melamine, methylol melamine, methylated methylol melamine, guanazole and the like, as well as mixtures thereof. Alternatively, one may use preformed resins alkylolated polyamines such as those commercially available under the trademark Urac® (origin: Cytec Technology Corp.), Cymel® (origin: Cytec Technology Corp.), Urecoll® or Luracoll® (origin: BASF).

[0060] Examples of other resins are the ones produced by the polycondensation of a polyol, like glycerol, and a polyisocyanate, like a trimer of hexamethylene diisocyanate, a trimer of isophorone diisocyanate or xylylene diisocyanate or a biuret of hexamethylene diisocyanate or a trimer of xylylene diisocyanate with trimethylolpropane (known with the tradename of Takenate®, origin: Mitsui Chemicals), among which a trimer of xylylene diisocyanate with trimethylolpropane and a biuret of hexamethylene diisocyanate are preferred.

[0061] Some of the seminal literature related to the encapsulation of perfumes by polycondensation of amino resins, namely melamine based resins with aldehydes includes articles such as those published by K. Dietrich et al. Acta Polymerica, 1989, Vol. 40, pages 243, 325 and 683, as well as 1990, Vol. 41 , page 91 . Such articles already describe the various parameters affecting the preparation of such core-shell microcapsules following prior art methods that are also further detailed and exemplified in the patent literature. US 4’396'670, to the Wiggins Teape Group Limited is a pertinent early example of the latter. Since then, many other authors have enriched the literature in this field and it would be impossible to cover all published developments here, but the general knowledge in encapsulation technology is very significant. More recent publications of pertinence, which disclose suitable uses of such microcapsules, are represented for example by the article of K. Bruyninckx and M. Dusselier, ACS Sustainable Chemistry & Engineering, 2019, vol. 7, pages 8041-8054.

[0062] As “perfumery base” is meant a composition comprising at least one perfuming co-ingredient which is not the compound of formula (I). Moreover, by “perfuming co-ingredient” it is meant here a compound, which is used in a perfuming preparation or a composition to impart a hedonic effect, i.e. used for the primary purpose of conferring or modulating an odor. In other words, such a co- ingredient, to be considered as being a perfuming one, must be recognized by a person skilled in the art as being able to impart or modify in a positive or pleasant way the odor of a composition, and not just as having an odor. The perfuming ingredient may impart an additional benefit beyond that of modifying or imparting an odor, such as long-lasting, blooming, malodour counteraction, antimicrobial effect, antiviral effect, microbial stability, or pest control.

[0063] The nature and type of the perfuming co-ingredients present in the base do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of his general knowledge and according to the intended use or application and the desired organoleptic effect. In general terms, these perfuming co-ingredients belong to chemical classes as varied as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, thiols, terpenoids, nitrogenous or sulphurous heterocyclic compounds and essential oils, and said perfuming co-ingredients can be of natural or synthetic origin.

[0064] In particular one may cite perfuming co-ingredients which are commonly used in perfume formulations, such as:

[0065] Aldehydic ingredients: decanal, dodecanal, 2-methyl-undecanal, 10- undecenal, octanal, nonanal and / or nonenal;

[0066] Aromatic-herbal ingredients: eucalyptus oil, camphor, eucalyptol, 5- methyltricyclo[6.2.1 ,02,7]undecan-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;

[0067] Balsamic ingredients: coumarin, ethylvanillin and / or vanillin;

[0068] Citrus ingredients: dihydromyrcenol, citral, orange oil, linalyl acetate, citronellyl nitrile, orange terpenes, limonene, 1-p-menthen-8-yl acetate and / or 1 ,4(8)-p-menthadiene;

[0069] Floral ingredients: methyl dihydrojasmonate, linalool, citronellol, phenylethanol, 3-(4-tert-butylphenyl)-2-methylpropanal, hexylcinnamic aldehyde, 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, (1 E)-1 -(2, 6, 6-trim ethy I- 2-cyclohexen-1 -yl)-1 -penten-3-one, 1 -(2, 6, 6-trim ethy 1-1 ,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- trim ethy 1-1 -cyclohexen-1 -yl)-2-buten-1 -one, 2,5-dimethyl-2-indanmethanol, 2,6,6-trimethyl-3-cyclohexene-1 -carboxylate, 3-(4,4-dimethyl-1 -cyclohexen-1 - yl)propanal, 3-(3,3 / 1 ,1 -dimethyl-5-indanyl)propanal, hexyl salicylate, 3,7- dimethyl-1 ,6-nonadien-3-ol, 3-(4-isopropylphenyl)-2-methylpropanal, verdyl acetate, geraniol, p-menth-1 -en-8-ol, 4-(1 ,1 -dimethylethyl)-1 -cyclohexyle acetate, 1 ,1 -dimethyl-2-phenylethyl acetate, 4-cyclohexyl-2-methyl-2-butanol, amyl salicylate , high cis methyl dihydrojasmonate, 3-methyl-5-phenyl-1- pentanol, verdyl proprionate, geranyl acetate, tetrahydro linalool, cis-7-p- menthanol, propyl (S)-2-(1 ,1 -dimethylpropoxy)propanoate, 2-methoxy- naphthalene, 2, 2, 2-trichloro-1 -phenylethyl acetate, 4 / 3-(4-hydroxy-4-methyl- pentyl)-3-cyclohexene-1-carbaldehyde, amylcinnamic aldehyde, 8-decen-5- olide, 4-phenyl-2-butanone, isononyle acetate, 4-(1 , 1 -dimethylethyl)-1 - cyclohexyl acetate, verdyl isobutyrate and / or mixture of methylionones isomers;

[0070] 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, gammanonalactone, allyl heptanoate, 2-phenoxyethyl isobutyrate, ethyl 2-methyl- 1 ,3-dioxolane-2-acetate, 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-cyclohexane dicarboxylate;

[0071] Green ingredients: 2-methyl-3-hexanone (E)-oxime, 2,4-dimethyl-3-cyclo- hexene-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;

[0072] Musk ingredients: 1 ,4-dioxa-5,17-cycloheptadecanedione, (Z)-4-cyclopenta- decen-1 -one, 3-methylcyclopentadecanone, 1 -oxa-12-cyclohexadecen-2- one, 1 -oxa-13-cyclohexadecen-2-one, (9Z)-9-cycloheptadecen-1-one, 2- {(1 S)-1-[(1 R)-3,3-dimethylcyclohexyl]ethoxy}-2-oxoethyl propionate, 3- methyl-5-cyclopentadecen-1 -one, 4,6,6,7,8,8-hexamethyl-1 , 3, 4, 6,7,8- hexahydrocyclopenta[g]isochromene, (1 S, 1 ' R)-2-[1 -(3' , 3'-d im ethy 1-1 '- cyclohexyl)ethoxy]-2-methylpropyl propanoate, oxacyclohexadecan-2- oneand / or (1 S, 1 ' R)-[ 1 -(3' , 3'-d im ethy 1-1 '-cyclohexyl)ethoxycarbonyl]methyl propanoate;

[0073] Woody ingredients: 1-[(1 RS,6SR)-2,2,6-trimethylcyclohexyl]-3-hexanol, 3,3- dimethyl-5-[(1 R)-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-naphtalenyl)-1 -ethanone, patchouli oil, terpenes fractions of patchouli oil, Clearwood® (Origin: Firmenich SA), (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;

[0074] Other ingredients (e.g. amber, powdery spicy or watery): dodecahydroSa, 6,6, 9a-tetramethyl-naphtho[2,1 -b]furan and any of its stereoisomers, heliotropin, anisic aldehyde, eugenol, cinnamic aldehyde, 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.

[0075] A perfumery base according to the invention may not be limited to the above-mentioned perfuming co-ingredients, and many other of these coingredients are in any case listed in reference texts such as the book by S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA, or its more recent versions, 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 also be compounds known to release in a controlled manner various types of perfuming compounds also known as properfume or profragrance. Non-limiting examples of suitable properfume 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-trimethy I- 3-cyclohexen-1 -yl)-1 -butanone, 3-(dodecylsulfonyl)-1 -(2,6,6-trimethylcyclohex-3- en-1 -yl)butan-1 -one, a linear polysiloxane co-polymer of (3-mercaptopropyl)- (methyl)dimethoxysilane, 3-(dodecylthio)-1 -(6-ethyl-2,6-dimethylcyclohex-3-en-1 - yl)butan-1 -one, 2-(dodecylthio)octan-4-one, 2-(dodecylsulfonyl)octan-4-one, 4- oxooctan-2-yl dodecanoate, 2-phenylethyl oxo(phenyl)acetate, 3,7-dimethylocta- 2,6-dien-1 -yl oxo(phenyl)acetate, (Z)-hex-3-en-1 -yl oxo(phenyl)acetate, 3,7- dimethyl-2,6-octadien-1 -yl hexadecanoate, bis(3,7-dimethylocta-2,6-dien-1 -yl) succinate, (2E,6Z)-2,6-nonadienyl hexadecanoate, (2E,6Z)-2,6-nonadien-1-yl tetradecanoate, (2E,6Z)-2,6-nonadien-1 -yl dodecanoate, (2-((2-methylundec-1 -en- 1 -yl)oxy)ethyl)benzene, 1 -methoxy-4-(3-methyl-4-phenethoxybut-3-en-1 -yl)- benzene, (3-methyl-4-phenethoxybut-3-en-1 -yl)benzene, 1 -(((Z)-hex-3-en-1 - yl)oxy)-2-methylundec-1 -ene, (2-((2-methylundec-1 -en-1 -yl)oxy)ethoxy)benzene, 2-methyl-1 -(octan-3-yloxy)undec-1 -ene, 1 -methoxy-4-(1 -phenethoxyprop-1 -en-2- yl)benzene, 1 -methyl-4-(1 -phenethoxyprop- 1 -en-2-yl)benzene, 2-(1 -phenethoxy- prop-1 -en-2-yl)naphthalene, (2-phenethoxyvinyl)benzene, 2-(1 -((3,7-dimethyloct- 6-en-1 -yl)oxy)prop-1 -en-2-yl)naphthalene, (2-((2-pentylcyclopentylidene)methoxy)- ethyl)benzene, 4-allyl-2-methoxy-1 -((2-methoxy-2-phenylvinyl)oxy)benzene, (2- ((2-heptylcyclopentylidene)methoxy)ethyl)benzene, 1 -methoxy-4-(1 -phenethoxy- prop-1 -en-2-yl)benzene, (2-((2-methyl-4-(2,6,6-trimethylcyclohex-1 -en-1 -yl)but-1 - en-1 -yl)oxy)ethyl)benzene, 1 -methoxy-4-(2-methyl-3-phenethoxyallyl)benzene, (2- ((2-isopropyl-5-methylcyclohexylidene)methoxy)ethyl)benzene, 1 -isopropyl-4- methyl-2-((2-pentylcyclopentylidene)methoxy)benzene, 2-methoxy-1 -((2-pentyl- cyclopentylidene)methoxy)-4-propylbenzene, 2-ethoxy-1 -((2-methoxy-2-phenyl- vinyl)oxy)-4-methylbenzene, 3-methoxy-4-((2-methoxy-2-phenylvinyl)oxy)- benzaldehyde, 1 -isopropyl-2-((2-methoxy-2-phenylvinyl)oxy)-4-methylbenzene, 4- ((2-(hexyloxy)-2-phenylvinyl)oxy)-3-methoxybenzaldehyde or a mixture thereof.

[0076] By “perfumery adjuvant”, it is meant here an ingredient capable of imparting additional added benefit such as a color, a particular light resistance, chemical stability, etc. A detailed description of the nature and type of adjuvant commonly used in perfuming composition cannot be exhaustive, but it has to be mentioned that said ingredients are well known to a person skilled in the art. One may cite as specific non-limiting examples the following: viscosity agents (e.g. surfactants, thickeners, gelling and / or rheology modifiers), stabilizing agents (e.g. preservatives, antioxidant, heat / light and or buffers or chelating agents, such as BHT (=3,5-Di-tert-butyl-4-hydroxytoluene)), coloring agents (e.g. dyes and / or pigments), preservatives (e.g. antibacterial or antimicrobial or antifungal or anti irritant agents), abrasives, skin cooling agents, fixatives, insect repellants, ointments, vitamins and mixtures thereof.

[0077] By “fixative” also called “modulator”, it is understood here an agent having the capacity to affect the manner in which the odor, and in particular the evaporation rate and intensity, of the compositions incorporating said modulator can be perceived by an observer or user thereof, over time, as compared to the same perception in the absence of the modulator. In particular, the modulator allows prolonging the time during which their fragrance is perceived. Non-limiting examples of suitable modulators may include methyl glucoside polyol; ethyl glucoside polyol; propyl glucoside polyol; isocetyl alcohol; PPG-3 myristyl ether; neopentyl glycol diethylhexanoate; sucrose laurate; sucrose dilaurate, sucrose myristate, sucrose palmitate, sucrose stearate, sucrose distearate, sucrose tristearate, hyaluronic acid disaccharide sodium salt, sodium hyaluronate, propylene glycol propyl ether; dicetyl ether; polyglycerin-4 ethers; isoceteth-5; isoceteth-7, isoceteth-10; isoceteth-12; isoceteth-15; isoceteth-20; isoceteth-25; isoceteth-30; disodium lauroamphodipropionate; hexaethylene glycol monododecyl ether; and their mixtures; neopentyl glycol diisononanoate; cetearyl ethylhexanoate; panthenol ethyl ether, DL-panthenol, n-hexadecyl n-nonanoate, n- octadecyl n-nonanoate, a profragrance, cyclodextrin, an encapsulation, and a combination thereof. Typically, at most 20% by weight, based on the total weight of the perfuming composition, of the modulator may be incorporated into the perfumed consumer product.

[0078] It is understood that a person skilled in the art is perfectly able to design optimal formulations for the desired effect by admixing the above mentioned components of a perfuming composition, simply by applying the standard knowledge of the art as well as by trial and error methodologies.

[0079] Preferred embodiments of the invention’s composition comprise -at least one compound of formula (I); -at least one perfumery carrier;

[0080] -at least one perfumery base;

[0081] - and, optionally, at least one perfumery adjuvant.

[0082] According to a particular embodiment, the perfuming composition is in the form of a microcapsule, preferably a microcapsule slurry, comprising at least one compound of formula (I). In one embodiment, the at least one compound of formula (I) is encapsulated in a core-shell microcapsule wherein the at least one compound of formula (I) is contained in the core surrounded by the shell. In one embodiment, the shell of the microcapsule protects the compound of formula (I) from the environment. The shell is made of material which is able to release the at least one compound of formula (I). In one embodiment, the shell is made of material which is able to release the compound of formula (I) upon breakage of the shell and / or by diffusion through the shell. A person skilled in the art is well aware of processes to prepare said microcapsules. The core of the core-shell microcapsule, in addition to compound of formula (I), may further comprise at least one liquid carrier as defined above and / or at least one perfuming co-ingredient as defined above. The core-shell microcapsules or the core-shell microcapsule slurry comprising at least one compound of formula (I) may be dispersed into at least one liquid carrier as defined above. Said liquid carrier may further comprise at least one compound of formula (I) and / or at least one perfuming co-ingredient as defined above.

[0083] According to a particular embodiment, the shell of the microcapsule comprises a material selected from the group consisting of polyurea, polyurethane, polyamide, polyester, poly(meth)acrylate (i.e. polyacrylate and / or polymethacrylate), polysiloxane, polycarbonate, polysulfonamide, polymers of urea and formaldehyde, melamine and formaldehyde, melamine and urea, or melamine and glyoxal and mixtures thereof. The shell can also be hybrid, namely organic-inorganic such as a hybrid shell composed of at least two types of inorganic particles that are cross-linked, or yet a shell resulting from the hydrolysis and condensation reaction of a polyalkoxysilane macro-monomeric composition.

[0084] According to a particular embodiment, the core-shell microcapsule(s) can be also derived by using different or more than one encapsulation method.

[0085] In a preferred embodiment, the shell of the microcapsules may be, each independently, selected from the group of aminoplast, polyamide, polyester, polyurea and polyurethane shells and mixtures thereof.

[0086] In a particular embodiment, the shell of the microcapsules comprise an aminoplast copolymer, such as melamine-formaldehyde or urea-formaldehyde or cross-linked melamine formaldehyde or melamine glyoxal.

[0087] In a particular embodiment, the shell of the microcapsules is polyurea- based made from, for example but not limited to, isocyanate-based monomers and amine-containing crosslinkers such as guanidine carbonate and / or guanazole. Certain polyurea microcapsules comprise a polyurea wall which is the reaction product of the polymerization between at least one polyisocyanate comprising at least two isocyanate functional groups and at least one reactant selected from the group consisting of an amine (for example a water-soluble guanidine salt and guanidine); a colloidal stabilizer or emulsifier; and an encapsulated perfume. However, the use of an amine can be omitted. In a particular embodiment, the colloidal stabilizer includes an aqueous solution of between 0.1% and 0.4% of polyvinyl alcohol, between 0.6% and 1% of a cationic copolymer of vinylpyrrolidone and of a quaternized vinylimidazole (all percentages being defined by weight relative to the total weight of the colloidal stabilizer). In a particular embodiment, the emulsifier is an anionic or amphiphilic biopolymer, which may be for example chosen from the group consisting of Gum Arabic, soy protein, gelatin, sodium caseinate and mixtures thereof.

[0088] In a particular embodiment, the shell of the microcapsules is polyurethane-based made from, for example but not limited to, polyisocyanate and polyols, polyamide, polyester, etc.

[0089] In a particular embodiment, the microcapsules have a polymeric shell resulting from complex coacervation wherein the shell is possibly cross-linked.

[0090] In a particular embodiment of the core-shell microcapsules, the core-shell microcapsules comprise an oil-based core comprising a hydrophobic active, preferably at least one compound of formula (I), and a composite shell comprising a first material and a second material, wherein the first material and the second material are different, the first material is a coacervate, the second material is a polymeric material.

[0091] In a particular embodiment, the weight ratio between the first material and the second material is comprised between 50:50 and 99.9:0.1.

[0092] In a particular embodiment, the coacervate comprises a first polyelectrolyte, preferably selected among proteins (such as gelatin), polypeptides or polysaccharides (such as chitosan), most preferably gelatin, and a second polyelectrolyte, preferably alginate salts, cellulose derivatives, guar gum, pectinate salts, carrageenan, polyacrylic and methacrylic acid or xanthan gum, or yet plant gums such as acacia gum (Gum Arabic), most preferably Gum Arabic.

[0093] The first coacervate material can be hardened chemically using a suitable cross-linker such as glutaraldehyde, glyoxal, formaldehyde, tannic acid or genipin or can be hardened enzymatically using an enzyme such as transglutaminase.

[0094] The second polymeric material can be selected from the group consisting of polyurea, polyurethane, polyamide, polyester, polyacrylate, polysiloxane, polycarbonate, polysulfonamide, polymers of urea and formaldehyde, melamine and formaldehyde, melamine and urea, or melamine and glyoxal and mixtures thereof, preferably polyurea and / or polyurethane. The second material is preferably present in an amount less than 3 wt.%, preferably less than 1 wt.% based on the total weight of the microcapsule slurry.

[0095] The preparation of an aqueous dispersion / slurry of core-shell microcapsules is well known by a skilled person in the art. In a particular embodiment, the microcapsule wall material may comprise any suitable resin and especially including melamine, glyoxal, polyurea, polyurethane, polyamide, polyester, etc. Suitable resins include the reaction product of an aldehyde and an amine, suitable aldehydes include, formaldehyde and glyoxal. Suitable amines include melamine, urea, benzoguanamine, glycoluril, and mixtures thereof. Suitable melamines include, methylol melamine, methylated methylol melamine, imino melamine and mixtures thereof. Suitable urea include, dimethylol urea, methylated dimethylol urea, urea-resorcinol, and mixtures thereof. Suitable materials for making may be obtained from one or more of the following companies Solutia Inc. (St Louis, Missouri U.S.A.), Cytec Industries (West Paterson, New Jersey U.S.A.), Sigma- Aldrich (St. Louis, Missouri U.S.A.).

[0096] In a particular embodiment of the core-shell microcapsules, the core-shell microcapsules comprise an oil-based core comprising a hydrophobic active, preferably comprising at least one compound of formula (I), optionally an inner shell made of a polymerized polyfunctional monomer; a biopolymer shell comprising a protein, wherein at least one protein is cross-linked.

[0097] According to a particular embodiment, the protein is chosen from the group consisting of milk proteins, caseinate salts such as sodium caseinate or calcium caseinate, casein, whey protein, hydrolyzed proteins, gelatins, gluten, pea protein, soy protein, silk protein and mixtures thereof, preferably sodium caseinate.

[0098] According to a particular embodiment, the protein comprises sodium caseinate and a globular protein, preferably chosen from the group consisting of whey protein, beta-lactoglobulin, ovalbumine, bovine serum albumin, vegetable proteins, and mixtures thereof.

[0099] The protein is preferably a mixture of sodium caseinate and whey protein. According to a particular embodiment, the biopolymer shell comprises a crosslinked protein chosen from the group consisting of sodium caseinate and / or whey protein.

[0100] According to a particular embodiment, the microcapsule slurry comprises at least one microcapsule made of: an oil-based core comprising the hydrophobic active, preferably comprising at least one compound of formula (I); an inner shell made of a polymerized polyfunctional monomer; preferably a polyisocyanate having at least two isocyanate functional groups; a biopolymer shell comprising a protein, wherein at least one protein is cross-linked; wherein the protein contains preferably a mixture comprising sodium caseinate and a globular protein, preferably whey protein; optionally at least an outer mineral layer.

[0101] According to an embodiment, sodium caseinate and / or whey protein is (are) cross-linked protein(s).

[0102] The weight ratio between sodium caseinate and whey protein is preferably comprised between 0.01 and 100, preferably between 0.1 and 10, more preferably between 0.2 and 5.

[0103] In a particular embodiment, the microcapsule is a one-shell aminoplast core-shell microcapsule obtainable by a process comprising the steps of:

[0104] 1 ) admixing a perfume oil with at least a polyisocyanate having at least two isocyanate functional groups to form an oil phase;

[0105] 2) dispersing or dissolving into water an aminoplast resin and optionally a stabilizer to form a water phase;

[0106] 3) preparing an oil-in-water dispersion, wherein the mean droplet size is comprised between 1 and 100 microns, by admixing the oil phase and the water phase;

[0107] 4) performing a curing step to form the wall of said microcapsule; and

[0108] 5) optionally drying the final dispersion to obtain the dried core-shell microcapsule. In a particular embodiment, the core-shell microcapsule is a formaldehyde-free capsule. A typical process for the preparation of an am inoplast formaldehyde-free microcapsule slurry comprises the steps of

[0109] T) preparing an oligomeric composition comprising the reaction product of, or obtainable by reacting together: a’, a polyamine component in the form of melamine or of a mixture of melamine and at least one C1-C4 compound comprising two NH2 functional groups; b’. an aldehyde component in the form of a mixture of glyoxal, a C4-6 2,2- dialkoxy-ethanal and optionally a glyoxalate, said mixture having a molar ratio glyoxal / C4-6 2,2-dialkoxy-ethanal comprised between 1 / 1 and10 / 1 ; and c’. a protic acid catalyst;

[0110] 2’) preparing an oil-in-water dispersion, wherein the droplet size is comprised between 1 and 600 microns, and comprising: a”, an oil; b”. a water medium; c”. at least an oligomeric composition as obtained in step T; d”. at least a cross-linker selected amongst: i”. C4-C12 aromatic or aliphatic di- or tri-isocyanates and their biurets, triurets, trimmers, trimethylol propane-adduct and mixtures thereof; and / or ii”. a di- or tri-oxiran compound of formula:

[0111] Q-(oxiran-2-ylrnethyl)m wherein m is 2 or 3 and Q represents a C2-C6 group optionally comprising from 2 to 6 nitrogen and / or oxygen atoms; e”. optionally a C1-C4 compounds comprising two NH2 functional groups;

[0112] 3’) heating the dispersion; and

[0113] 4’) cooling the dispersion.

[0114] The above process is described in more detail in WO 2013 / 068255.

[0115] In a particular embodiment of the core-shell microcapsules, the core-shell microcapsule is a polyamide core-shell microcapsule comprising: an oil based core comprising an hydrophobic active, preferably comprising at least one compound of formula (I), and a polyamide shell comprising or being obtainable from:

[0116] • an acyl chloride,

[0117] • a first amino compound, and

[0118] • a second amino compound.

[0119] According to a particular embodiment, the polyamide core-shell microcapsule comprises:

[0120] - an oil based core comprising an hydrophobic active, preferably comprising at least one compound of formula (I), and

[0121] - a polyamide shell comprising or being obtainable from:

[0122] • an acyl chloride, preferably in an amount comprised between 5 and 98%, preferably between 20 and 98%, more preferably between 30 and 85% w / w;

[0123] • a first amino compound, preferably in an amount comprised between 1 % and 50% w / w, preferably between 7 and 40% w / w;

[0124] • a second amino compound, preferably in an amount comprised between 1 % and 50% w / w, preferably between 2 and 25% w / w;

[0125] • a stabilizer, preferably a biopolymer, preferably in an amount comprised between 0 and 90%, preferably between 0.1 and 75%, more preferably between 1 and 70%.

[0126] According to a particular embodiment, the polyamide core-shell microcapsule comprises: an oil based core comprising a hydrophobic active, preferably comprising at least one compound of formula (I), and a polyamide shell comprising or being obtainable from:

[0127] • an acyl chloride,

[0128] • a first amino-compound being an amino-acid, preferably chosen from the group consisting of L-Lysine, L-Arginine, L-Histidine, L-Tryptophane and / or a mixture thereof. • a second amino. compound chosen from the group consisting of ethylene diamine, diethylene triamine, cystamine and / or a mixture thereof, and

[0129] • a biopolymer chosen from the group consisting of casein, sodium caseinate, bovin serum albumin, whey protein, and / or a mixture thereof.

[0130] The first amino-compound can be different from the second aminocompound.

[0131] Typically, a process for preparing a polyamide-based microcapsule includes the following steps: a) dissolving at least one acyl chloride in a hydrophobic material, preferably a perfume to form an oil phase; b) dispersing the oil phase obtained in step a) into a water phase comprising a first amino compound to form an oil-in water emulsion; c) performing a curing step to form polyamide microcapsules in the form of a slurry; wherein a stabilizer is added in the oil phase and / or in the water phase, and wherein at least a second amino-compound is added in the water phase before the formation of the oil-in-water emulsion and / or in the oil-in water emulsion obtained after step b).

[0132] In a particular embodiment, the shell of the microcapsule is polyurea-or polyurethane-based. Examples of processes for the preparation of polyurea and polyureathane-based microcapsule slurries are for instance described in WO 2007 / 004166, EP 2300146, and EP 2579976. Typically, a process for the preparation of polyurea or polyurethane-based microcapsule slurries include the following steps: a) dissolving at least one polyisocyanate having at least two isocyanate groups in an oil to form an oil phase; b) preparing an aqueous solution of an emulsifier or colloidal stabilizer to form a water phase; c) adding the oil phase to the water phase to form an oil-in-water dispersion, wherein the mean droplet size is comprised between 1 and 500 pm, preferably between 5 and 50 pm; and d) applying conditions sufficient to induce interfacial polymerization and form microcapsules in form of a slurry.

[0133] In a particular embodiment, the microcapsule can be in form of a powder, which in particular may be obtained by submitting the microcapsule slurry to a drying step, like spray-drying, to provide the microcapsules as such, i.e. in a powdery form. It is understood that any standard method known by a person skilled in the art to perform such drying is also applicable. In particular the slurry may be spray-dried, preferably in the presence of a polymeric carrier material such as polyvinyl acetate, polyvinyl alcohol, dextrins, natural or modified starch, gum Arabic, vegetable gums, pectins, xanthans, alginates, carrageenans or cellulose derivatives to provide microcapsules in a powder form.

[0134] However, one may also cite other drying methods such as extrusion, plating, spray granulation or fluidized bed processes, or even drying at room temperature using materials (carrier, desiccant) that meet specific criteria as disclosed in WO 2017 / 134179.

[0135] According to a particular embodiment, the compositions mentioned above, comprise more than one compound of formula (I) and enable the perfumer to prepare accords or perfumes possessing the odor tonality of various compounds of the invention, creating thus new building block for creation purposes.

[0136] For the sake of clarity, it is also understood that any mixture resulting directly from a chemical synthesis, e.g. a reaction medium without an adequate purification, in which the compound of the invention would be involved as a starting, intermediate or end-product could not be considered as a perfuming composition according to the invention as far as said mixture does not provide the inventive compound in a suitable form for perfumery. Thus, unpurified reaction mixtures are generally excluded from the present invention unless otherwise specified.

[0137] The invention’s compound can also be advantageously used in all the fields of modem perfumery, i.e. fine or functional perfumery, to positively impart or modify the odor of a consumer product into which said compound (I) is added. Consequently, another object of the present invention consists of a perfumed consumer product comprising, as a perfuming ingredient, at least one compound of formula (I), as defined above. The invention’s compound can be added as such or as part of an invention’s perfuming composition.

[0138] Said perfuming composition is preferably of daily use, particularly a cosmetic product or a grooming, fabric or home care product.

[0139] Therefore, in a further embodiment, the invention relates to a perfumed consumer product comprising

[0140] -at least one compound of formula (I) as discussed above in great details, or -a perfuming composition as discussed above in great details.

[0141] For the sake of clarity, “perfumed consumer product” is meant to designate a consumer product which delivers at least a pleasant perfuming effect to the surface or space to which it is applied (e.g. skin, hair, textile, or home surface). In other words, a perfumed consumer product according to the invention is a perfumed consumer product which comprises a functional formulation, as well as optionally additional benefit agents, corresponding to the desired consumer product, and an olfactive effective amount of at least one invention’s compound. For the sake of clarity, said perfumed consumer product is a non-edible product.

[0142] The nature and type of the constituents of the perfumed consumer product do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of his general knowledge and according to the nature and the desired effect of said product.

[0143] Non-limiting examples of suitable perfumed consumer products include a perfume, such as a fine perfume, a splash or eau de parfum, a cologne or a shave or after-shave lotion; a fabric care product, such as a liquid or solid detergent optionally in the form of a pod or tablet, a fabric softener, a liquid or solid scent booster, a dryer sheet, a fabric refresher, an ironing water, a paper, a bleach, a carpet cleaner, a curtain-care product; a body-care product, such as a hair care product (e.g. a shampoo, a leave-on or rinse-off hair conditioner, a coloring preparation or a hair spray, a color-care product, a hair shaping product, a dental care product), a disinfectant, an intimate care product; a cosmetic preparation (e.g. a skin cream or lotion, a vanishing cream or a deodorant or antiperspirant (e.g. a spray or roll on), a hair remover, a tanning or sun or after sun product, a nail product, a skin cleansing, a makeup); or a skin-care product (e.g. a soap, a shower or bath mousse, oil or gel, or a hygiene product or a foot / hand care products); an air care product, such as an air freshener or a “ready to use” powdered air freshener which can be used in the home space (rooms, refrigerators, cupboards, shoes or car) and / or in a public space (halls, hotels, malls, etc..); or a grooming, fabric or home care product, such as a mold remover, a furnisher care product, a wipe, a dish detergent or a hard-surface (e.g. a floor, bath, sanitary or a window-cleaning) detergent, a laundry product, a fabric washing powder, a fabric washing gel, a soluble laundry sheet; a leather care product; a car care product, such as a polish, a wax or a plastic cleaner.

[0144] Therefore, the perfumed consumer product is preferably 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.

[0145] More preferably, the perfumed consumer product is a fine perfume, a splash or eau de parfum, a cologne, a shave or after-shave lotion, a liquid or solid detergent optionally in the form of a pod or tablet, a laundry sheet, a soluble laundry sheet, a fabric softener, a liquid or solid scent booster, a dryer sheet, a fabric refresher, an ironing water, a paper, a bleach, a carpet cleaner, a curtaincare product, a shampoo, a leave-on or rinse-off hair conditioner, a coloring preparation, a color-care product, a hair shaping product, a dental care product, a disinfectant, an intimate care product, a hair spray, skin cream or lotion, a vanishing cream, a deodorant or antiperspirant, a hair remover, a tanning or sun or after sun product, a nail product, a skin cleansing, a makeup, a perfumed soap, a shower or bath mousse, oil or gel, a foot / hand care product, a hygiene product, an air freshener, a “ready to use” powdered air freshener, a mold remover, a furnisher care, a wipe, a dish detergent or hard-surface detergent, a leather care product, a car care product.

[0146] According to any embodiments of the invention, the perfumed consumer product of the invention is characterized by a pH of 1 or more. Particularly, the perfumed consumer product of the invention has a pH comprised between 1 and 12, or between 1 and 8. Even more particularly, the perfumed consumer product of the invention has a pH comprised between 1 and 6.

[0147] According to a particular embodiment, the invention’s perfumed consumer product is in the form of a personal care, a home care or fabric care consumer product comprising ingredients that are common in personal, home or fabric care consumer products, in particular shower gels, shampoos, soaps, fabric detergents or softeners and all-purpose cleaners. The main functional constituents of perfumed consumer products are surfactants and / or softener components capable of cleaning and / or softening fabrics and / or textiles of varied nature, such as clothes, curtain fabrics, carpets and furniture fabrics, etc. or other home surfaces, skin or hair, and typically used in a large amount of water or water-based solvents. These are therefore formulations wherein the amount of water is typically comprised between 50 and 99% by weight of the perfumed consumer product with the exception of soaps or solid detergents wherein the amount of water is at most 20%.

[0148] A more detailed description of such fabric cleaning and / or softening formulations is not warranted here, many descriptions of current liquid formulations can be found in the cleaner / fabric softener’s patent and other pertinent literature, such as for example the textbook of Louis Ho Tan Tai, “Detergents et Produits de Soins Corporals, Chapters 1 to 7 in particular, Dunod, Paris, 1999, or any other similar and / or more recent textbooks pertaining to the art of liquid softener and all-purpose cleaners formulations. A patent publication, WO 2010 / 105873, is also cited by way of example, in as much as it describes typical currant ingredients, other than perfumes, of such liquid products, particularly in pages 9 to 21 . Of course, many other examples of liquid cleaner and / or fabric softener formulations can be found in the literature. Any such liquid formulations, namely liquid fabric cleaners or conditioners and / or all-purpose cleaners, can be used in the here-described compositions.

[0149] According to a particular embodiment of the invention, the invention’s perfumed consumer product is a liquid fabric softener comprising a fabric softener active base in amount comprised between 85 and 100% by weight, based on the total weight of the perfumed consumer product. The main constituent of the fabric softener active base is water or water-based solvents. The fabric softener active base may comprise dialkyl quaternary ammonium salts, dialkyl ester quaternary ammonium salts, Hamburg esterquat, triethanolamine quat, silicones and mixtures thereof. Optionally, the fabric softener active base of the composition may further comprise a viscosity modifier in an amount comprised between 0.05 and 1 % by weight, based on the total weight of the liquid base; preferably chosen in the group consisting of calcium chloride.

[0150] According to a particular embodiment of the invention, the invention’s perfumed consumer product is an all-purpose cleaner comprising an all-purpose cleaner active base in amount comprised between 85 and 100% by weight, based on the total weight of the perfumed consumer product. The main constituent of the all-purpose cleaner active base is water or water-based solvents The all-purpose active base may comprise linear alkylbenzene sulfonates (LAS) in an amount comprised between 1 and 2%, nonionic surfactant in an amount comprised between 2 and 4% and acid such as citric acid in an amount comprised between 0.1 and 0.5%.

[0151] According to a particular embodiment of the invention, the invention’s perfumed consumer product is a liquid detergent comprising a liquid detergent active base in amount comprised between 85 and 100% by weight, based on the total weight of the perfumed consumer product. The main constituent of the liquid detergent active base is water or water-based solvents. The liquid detergent active base may comprise anionic surfactant such as alkylbenzenesulfonate (ABS), linear alkylbenzene sulfonates (LAS), secondary alkyl sulfonate (SAS), primary alcohol sulfate (PAS), lauryl ether sulfate (LES), sodium lauryl ether sulfate (SLES), methyl ester sulfonate (MES); nonionic surfactant such as alkyl amines, alkanolamide, fatty alcohol polyethylene glycol) ether, fatty alcohol ethoxylate (FAE), ethylene oxide (EO) and propylene oxide (PO) copolymers, amine oxides, alkyl polyglucosides, alkyl polyglucosamides; ormixtures thereof.

[0152] According to a particular embodiment of the invention, the invention’s perfumed consumer product is a solid detergent comprising a solid detergent active base in amount comprised between 85 and 100% by weight, based on the total weight of the perfumed consumer product. The solid detergent active base may comprise at least one surfactant chosen in the group consisting of anionic, nonionic, cationic, zwitterionic surfactant and mixtures thereof. The surfactant in the solid detergent active base is preferably chosen in the group consisting of linear alkene benzene sulfonate (LABS), sodium laureth sulphate, sodium lauryl ether sulfate (SLES), sodium lauryl sulfate (SLS), alpha olefin sulfonate (AOS), methyl ester sulfonates (MES), alkyl polyglyucosides (APG), primary alcohol ethoxylates and in particular lauryl alcohol ethoxylates (LAE), primary alcohol sulphonates (PAS), soap and mixtures thereof. The soild detergent active base may comprise a further component, commonly used in powder detergent consumer product, selected from the group consisting of bleaching agents such as TAED (tetraacetylethylenediamine); buffering agent; builders such as zeolites, sodium carbonate or mixture thereof; soil release or soil suspension polymers; granulated enzyme particles such as cellulase, lipase, protease, mannanase, pectinase or mixtures thereof; corrosion inhibitor; antifoaming; sud suppressing agents; dyes; fillers such as sodium silicate, sodium sulfate or mixture thereof; source of hydrogen peroxide such as sodium percarbonate or sodium perborate; and mixtures thereof.

[0153] According to a particular embodiment of the invention, the invention’s perfumed consumer product is shampoo or a shower gel comprising a shampoo or shower gel active base in amount comprised between 85 and 100% by weight, based on the total weight of the perfumed consumer product. The main constituent of the shampoo or a shower gel active base is water or water-based solvents The shampoo shower gel active base may comprise sodium alkylether sulfate, ammonium alkylether sulfates, alkylamphoacetate, cocam idopropyl betaine, cocam ide MEA, alkylglucosides and aminoacid based surfactants.

[0154] According to a particular embodiment of the invention, the invention’s perfumed consumer product is a soap bar comprising a soap active base in amount comprised between 85 and 100% by weight, based on the total weight of the perfumed consumer product. The soap bar active base may comprise salt of a weak acid, typically, a salt of weak acid, which may be a fatty acid and strong base like sodium hydroxide.

[0155] Some of the above-mentioned perfumed consumer products may represent an aggressive medium for the invention’s compounds, so that it may be necessary to protect the latter from premature decomposition, for example by encapsulation or by chemically binding it to another chemical which is suitable to release the invention’s ingredient upon a suitable external stimulus, such as an enzyme, light, heat or a change of pH. The proportions in which the compounds according to the invention can be incorporated into the various aforementioned products or compositions vary within a wide range of values. These values are dependent on the nature of the article to be perfumed and on the desired organoleptic effect as well as on the nature of the co-ingredients in a given base when the compounds according to the invention are mixed with perfuming co-ingredients, solvents or additives commonly used in the art.

[0156] For example, in the case of perfuming compositions, typical concentrations are in the order of 0.001 % to 10 % by weight, or even more, for example 0.001 % to 30%, or even more, of the compounds of the invention based on the weight of the composition into which they are incorporated. In the case of perfumed consumer product, typical concentrations are in the order of 0.0001 % to 10% by weight, or even more, for example 0.01 % to 1 % by weight, or even more, of the compounds of the invention based on the weight of the consumer product into which they are incorporated.

[0157] As pointed out, above the compound of the formula (I) has a typical odor of fig.

[0158] Therefore, in a further aspect, the present invention relates also to the use of the formula (I) according to any of the preceding claims 1-4 to impart a fig odor to a chemical composition.

[0159] Finally, in a further aspect, the present invention relates to a method to confer or enhance or improve or modify the odor properties of a perfuming composition or of a perfumed article, which method comprises adding to said composition or article an effective amount of at least a compound of formula (I).

[0160] Examples The following examples are provided to further illustrate the compositions and effects of the present invention. These examples are illustrative only and are not intended to limit the scope of the invention in any way.

[0161] The abbreviations have the usual meaning in the art, the temperatures are indicated in degrees centigrade (°C). NMR spectra were acquired using either a Bruker Avance II Ultrashield 400 plus operating at 400 MHz, (1H) and 100 MHz (13C) or a Bruker Avance III 500 operating at 500 MHz (1H) and 125 MHz (13C) or a Bruker Avance III 600 cryoprobe operating at 600 MHz (1H) and 150 MHz (13C). Spectra were internally referenced relative to tetramethyl silane 0.0 ppm.1H NMR signal shifts are expressed in 6 ppm, coupling constants (J) are expressed in Hz with the following multiplicities: s, singlet; d, doublet; t, triplet; q, quartet; m, multiplet; b, broad (indicating unresolved couplings) and were interpreted using Bruker Topspin software.13C NMR data are expressed in chemical shift 6 ppm and hybridization from DEPT 90 and DEPT 135 experiments, C, quaternary; CH, methine; CH2, methylene; CH3, methyl.

[0162] Synthesis of compounds of formula (I)

[0163] Example 1: 2,2,4-trimethylheptan-3-one oxime (I- A)

[0164] To a solution of 2,2,4-trimethylheptan-3-one (349 mg, 2.21 mmol, 1 equiv.) and pyridine (1.93 mL, 23.8 mmol, 10.8 equiv.) in ethanol (6 mL) was added hydroxylamine hydrochloride (404 mg, 5.75 mmol, 2.6 equiv.) and the mixture was refluxed for 7 days. After cooling down to room temperature, it was diluted with ether and washed successively with 5% HCI, water, saturated NaHCOs and brine. The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by flash column chromatography on silica gel (Heptane / AcOEt ethyl acetate) 94:6) and bulb-to-bulb distillation to afford 2,2,4-trimethylheptan-3-one oxime (234 mg, 62 % yield).

[0165] 1H NMR (CDCI3, 500 MHz): 5 = 0.91 (t, J = 7.3 Hz, 3H), 1.12 (s, 9H), 1.21 (m, 1 H), 1 .27 (d, J = 7.0 Hz, 3H), 1 .40 (m, 1 H), 1 .66 (m, 1 H), 1 .90 (m, 1 H), 2.41 (m, 1 H), 8.88 (s, 1 H).

[0166] 13C NMR (CDCI3, 125 MHz): 5 = 168.8 (s), 38.1 (s), 35.0 (t), 34.8 (d), 27.7 (q, 3C), 21.5 (t), 16.0 (q), 14.3 (q).

[0167] Example 2: 3,3,5-trimethyloctan-4-one oxime (l-B)

[0168] Step 1: synthesis of 3,3,5-trimethyloct-1 -en-4-ol:

[0169] To a solution of 2-methylpentanal (6.20 mL, 39.6 mmol, 1 equiv.) in saturated NH4CI (248 mL) and THF (50 mL) at room temperature was added zinc powder (4.20 g, 63.6 mmol, 1.6 equiv.) followed by 1-bromo-3-methylbut-2-ene (8.20 mL, 63.4 mmol, 1 .6 equiv.) dropwise. After stirring for 10 min, the reaction was transferred into a separating funnel and the aqueous layer was extracted three times with ether. The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by flash column chromatography on silica gel (Pentane / Et2O 95:5) and bulb-to-bulb distillation to afford 3,3,5-trimethyloct-1-en-4-ol (4.16 g, 61 % yield).1H NMR (CDCI3, 600 MHz): 6 = 0.84 (d, J = 6.8 Hz, 3H, 1 dias), 0.89 (t, J = 6.4 Hz, 3H, 2 dias), 0.97 (d, J = 6.9 Hz, 3H, 1 dias), 1 .04 (s, 3H, 1 dias), 1 .05 (s, 3H, 1 dias), 1.05 (s, 3H, 1 dias), 1.06 (s, 3H, 1 dias), 1.17-1.77 (m, 5H, 2 dias), 3.17 (s, 1 H, 1 dias), 3.25 (s, 1 H, 1 dias), 5.01 -5.06 (m, 2H, 2 dias), 5.90 (m, 1 H, 2 dias).

[0170] 13C NMR (CDCI3, 150 MHz): major isomer: 5 = 145.7 (d), 112.7 (t), 80.6 (d), 42.3 (s), 39.6 (t), 33.2 (d), 24.6 (q), 23.7 (q), 20.4 (t), 14.2 (q, 2C); minor isomer: 5 = 145.8 (d), 112.6 (t), 82.9 (d), 42.4 (s), 34.0 (d), 33.1 (t), 24.4 (q), 23.7 (q), 20.8 (t), 20.1 (q), 14.4 (q).

[0171] Step 2: synthesis of 3,3,5-trimethyloctan-4-ol:

[0172] To a solution of 3,3,5-trimethyloct-1-en-4-ol (2.34 g, 13.6 mmol) in AcOEt (33 mL) at room temperature was added 5% Pd / C (117 mg) and the mixture was reacted with 1 bar of H2 with vigorous shaking. After the theoretical volume of H2 was consumed, the catalyst was filtered and the solvent was evaporated. The residue was purified by bulb-to-bulb distillation to afford 3,3,5-trimethyloctan-4-ol (2.13 g, 91 % yield).

[0173] 1H NMR (CDCI3, 600 MHz): 5 = 0.83-1.00 (m, 15H, 2 dias), 1.20-1.55 (m, 6H, 2 dias), 1.68-1.79 (m, 1 H, 2 dias), 3.18 (d, J = 2.0 Hz, 1 H, 1 dias), 3.26 (s, 1 H, 1 dias).

[0174] 13C NMR (CDCI3, 150 MHz): major isomer: 5 = 80.4 (d), 40.1 (t), 38.3 (s), 32.9 (d), 32.0 (t), 23.4 (q), 22.9 (q), 20.5 (t), 14.4 (q), 14.3 (q), 8.3 (q); minor isomer: 5 = 82.8 (d), 38.5 (s), 33.5 (d), 33.3 (t), 32.0 (t), 23.3 (q), 23.0 (q), 21.0 (t), 20.6 (q), 14.5 (q), 8.3 (q).

[0175] Step 3: Synthesis of 3,3,5-trimethyloctan-4-one:

[0176] To a solution of 3,3,5-trimethyloctan-4-ol (1.22 g, 7.08 mmol, 1 equiv.) in CH2CI2 (9 mL) at room temperature was added Dess-Martin periodinane (3.60 g, 8.49 mmol, 1 .2 equiv.) in portions. After stirring for 5 min, water was added and the aqueous layer was extracted 3 times with ether. The combined organic layers were washed successively with water, saturated NaHCOs, water and brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by bulb- to-bulb distillation to afford 3,3,5-trimethyloctan-4-one (1.04 g, 85 % yield).

[0177] 1H NMR (CDCI3, 600 MHz): 5 = 0.81 (t, J = 7.5 Hz, 3H), 0.88 (t, J = 7.2 Hz, 3H), 1.01 (d, J = 6.7 Hz, 3H), 1 .10 (s, 3H), 1.12 (s, 3H), 1.17-1.36 (m, 3H), 1.50- 1 .59 (m, 3H), 2.97 (hex, J = 6.7 Hz, 1 H).

[0178] 13C NMR (CDCI3, 150 MHz): 5 = 219.8 (s), 48.2 (s), 39.3 (d), 36.5 (t), 31.8 (t), 23.6 (q), 23.4 (q), 20.7 (t), 18.0 (q), 14.2 (q), 9.1 (q).

[0179] Step 4: Synthesis of 3,3,5-trimethyloctan-4-one oxime:

[0180] To a solution of 3,3,5-trimethyloctan-4-one (604 mg, 3.51 mmol, 1 equiv.) and pyridine (3.20 mL, 39.2 mmol, 11 .2 equiv.) in ethanol (6 mL) was added hydroxylamine hydrochloride (641 mg, 9.13 mmol, 2.6 equiv.) and the mixture was refluxed for 20 days. After cooling down to room temperature, it was diluted with ether and washed successively with 5% HCI, water, saturated NaHCOs and brine. The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by flash column chromatography on silica gel (Heptane / AcOEt 94:6) and bulb-to-bulb distillation to afford 3,3,5-trimethyloctan-4-one oxime (189 mg, 29 % yield, pure E-isomer).

[0181] 1H NMR (CDCI3, 600 MHz): 5 = 0.84 (t, J = 7.5 Hz, 3H), 0.91 (t, J = 7.3 Hz, 3H), 1.06 (s, 6H), 1.19 (m, 1 H), 1.26 (d, J = 7.0 Hz, 3H), 1.39-1.51 (m, 3H), 1.57 (m, 1 H), 1.95 (m, 1 H), 2.35 (m, 1 H), 8.18 (s, 1 H).

[0182] 13C NMR (CDCI3, 150 MHz): 5 = 168.2 (s), 41.4 (s), 35.1 (t), 34.5 (d), 32.3 (t), 25.5 (q), 24.8 (q), 21.5 (t), 15.9 (q), 14.3 (q), 9.1 (q). Alternative synthesis of 3,3,5-trimethyloctan-4-one oxime:

[0183] To a solution of N,O-bis(trimethylsilyl)hydroxylamine (5.18 g, 23.5 mmol, 2 equiv.) in THF (2.3 mL) at -78°C was added KHMDS (21.1 mL, 1 M in THF, 21.1 mmol, 1 .8 equiv.) dropwise. The mixture was stirred at room temperature for 30 min, then cooled down again to -78°C. A solution of 3,3,5-trimethyloctan-4-one (2.00 g, 11.7 mmol, 1 equiv.) in THF (3 mL) was added dropwise and the reaction was allowed to stir at room temperature for 3 days before being quenched with 5 % HCI. The aqueous layer was extracted 3 times with ether, and the combined organic layers were washed successively with water, saturated NaHCOs, water and brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by flash column chromatography on silica gel (Heptane / AcOEt 94:6) and bulb-to-bulb distillation to afford 3,3,5-trimethyloctan-4-one oxime (1.71 g, 78 % yield, 81 :19 mixture of Z- and E-isomers).

[0184] 1H NMR (CDCI3, 500 MHz) (Z-isomer): 5 = 0.80 (t, J = 7.5 Hz, 3H), 0.89 (t, J = 7.2 Hz, 3H), 1 .07 (d, J = 6.7 Hz, 3H), 1 .22 (s, 3H), 1 .23 (s, 3H), 1 .25-1 .37 (m, 3H), 1 .59 (m, 1 H), 1 .80 (m, 1 H), 1 .89 (m, 1 H), 2.45 (hex, J = 6.8 Hz, 1 H), 9.25 (s, 1 H).

[0185] 13C NMR (CDCI3, 125 MHz) (Z-isomer): 5 = 166.5 (s), 41.4 (s), 38.6 (t), 36.0 (d), 32.6 (t), 26.3 (q), 26.0 (q), 20.7 (t), 20.4 (q), 14.2 (q), 9.8 (q).

[0186] Example 3: 3,5-dimethyloctan-4-one oxime (l-C)

[0187] To a solution of 3,5-dimethyloctan-4-one (2.00 g, 12.5 mmol, 1 equiv.) and pyridine (11 .0 mL, 135 mmol, 10.8 equiv.) in ethanol (23 mL) was added hydroxylamine hydrochloride (2.29 g, 32.6 mmol, 2.6 equiv.) and the mixture was refluxed for 2 h. After cooling down to room temperature, it was diluted with ether and washed successively with 5% HCI, water, saturated NaHCOs and brine. The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by flash column chromatography on silica gel (Heptane / AcOEt 94:6) and bulb-to-bulb distillation to afford 3,5-dimethyloctan-4-one oxime (2.05 g, 95 % yield).1H NMR (CDCI3, 600 MHz): 6 = 0.88-0.93 (m, 6H, 4 isom.), 1.08-1.14 (m, 6H, 4 isom.), 1.23-1.67 (m, 6H, 4 isom.), 2.25 (hept, J = 6.8 Hz, 1 H, 2 isom.), 2.35 (hept, J = 6.8 Hz, 1 H, 2 isom.), 2.91 (m, 1 H, 2 isom.), 3.05 (oct, J = 7.3 Hz, 1 H, 2 isom.), 9.30 (s, 1 H, 4 isom.).

[0188] 13C NMR (CDCI3, 150 MHz): 5 = 167.6, 167.6, 167.5, 167.5, 37.8, 37.8, 37.6, 37.4, 36.0, 35.8, 35.7, 35.6, 35.0, 34.7, 32.8, 32.6, 28.5, 28.1 , 26.3, 26.2, 21.1 , 21.1 , 20.7, 20.7, 19.5, 19.2, 19.2, 19.0, 16.6, 16.6, 16.3, 16.3, 14.2, 14.2, 14.1 , 14.1 , 12.5, 12.5, 12.1 , 12.1.

[0189] Example 4: 3,3,5-trimethyloct-1-en-4-one oxime (l-D)

[0190] Step 1: Synthesis of 3,3, 5-trimethyloct-1-en-4-one:

[0191] To a solution of 3,3,5-trimethyloct-1-en-4-ol (1.00 g, 5.81 mmol, 1 equiv.) in CH2CI2 (7 mL) at room temperature was added Dess-Martin periodinane (2.96 g, 6.98 mmol, 1.2 equiv.) in portions. After stirring for 5 min, water was added and the aqueous layer was extracted 3 times with ether. The combined organic layers were washed successively with water, saturated NaHCOs, water and brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by bulb- to-bulb distillation to afford 3,3,5-trimethyloct-1 -en-4-one (812 mg, 82 % yield).

[0192] 1H NMR (CDCI3, 600 MHz): 5 = 0.86 (t, J = 7.1 Hz, 3H), 0.99 (d, J = 6.8 Hz, 3H), 1.16 (m, 1 H), 1.22 (s, 3H), 1.23 (s, 3H), 1.24-1.27 (m, 2H), 1.54 (m, 1 H), 2.94 (hex, J = 6.7 Hz, 1 H), 5.16-5.20 (m, 2H), 5.92 (m, 1 H).

[0193] 13C NMR (CDCI3, 150 MHz): 5 = 217.0 (s), 142.1 (d), 114.4 (t), 51.3 (s), 40.1 (d), 36.5 (t), 23.3 (q), 23.2 (q), 20.7 (t), 18.4 (q), 14.2 (q).

[0194] Step 2: Synthesis of 3,3,5-trimethyloct-1 -en-4-one oxime:

[0195] To a solution of 3,3,5-trimethyloct-1-en-4-one (394 mg, 2.32 mmol, 1 equiv.) and pyridine (2.10 mL, 25.7 mmol, 11.1 equiv.) in ethanol (4 mL) was added hydroxylamine hydrochloride (427 mg, 6.08 mmol, 2.6 equiv.) and the mixture was refluxed for 13 days. After cooling down to room temperature, it was diluted with ether and washed successively with 5% HCI, water, saturated NaHCOs and brine. The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by flash column chromatography on silica gel (Heptane / AcOEt 94:6) and bulb-to-bulb distillation to afford 3,3,5-trimethyloct-1-en-4-one oxime (242 mg, 55 % yield).

[0196] 1H NMR (CDCI3, 600 MHz): 5 = 0.89 (t, J = 7.3 Hz, 3H), 1.15 (m, 1 H), 1.20 (s, 3H), 1 .21 (s, 3H), 1 .22 (d, J = 7.0 Hz, 3H), 1 .36 (m, 1 H), 1 .61 (m, 1 H), 1 .84 (m, 1 H), 2.30 (m, 1 H), 5.06-5.10 (m, 2H), 5.85 (m, 1 H), 8.41 (s, 1 H).

[0197] 13C NMR (CDCI3, 150 MHz): 5 = 167.3 (s), 144.4 (d), 112.6 (t), 44.3 (s), 35.3 (d), 35.0 (t), 24.7 (q), 24.6 (q), 21.4 (t), 16.1 (q), 14.3 (q).

[0198] Example 5: 2,4-dimethylheptan-3-one oxime (l-E)

[0199] To a solution of 2,4-dimethylheptan-3-one (2.00 g, 13.9 mmol, 1 equiv.) and pyridine (12.2 mL, 150 mmol, 10.8 equiv.) in ethanol (26 mL) was added hydroxylamine hydrochloride (2.54 g, 36.2 mmol, 2.6 equiv.) and the mixture was refluxed for 16 h. After cooling down to room temperature, it was diluted with ether and washed successively with 5% HCI, water, saturated NaHCOs and brine. The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by flash column chromatography on silica gel (Heptane / AcOEt 94:6) and bulb-to-bulb distillation to afford 2,4-dimethylheptan-3-one oxime (2.13 g, 97 % yield).

[0200] 1H NMR (CDCI3, 600 MHz): 5 = 0.88-0.92 (m, 3H, 2 isom.), 1.09-1.16 (m, 9H, 2 isom.), 1.22-1.62 (m, 4H, 2 isom.), 2.39 (hex, J = 6.7 Hz, 1 H, 1 isom.), 2.52 (hept, J = 6.9 Hz, 1 H, 1 isom.), 3.07 (hex, J = 7.2 Hz, 1 H, 1 isom.), 3.18 (hept, J = 7.0 Hz, 1 H, 1 isom.), 9.35 (s, 1 H, 2 isom.).

[0201] 13C NMR (CDCI3, 150 MHz): 5 = 168.2, 168.0, 37.5, 35.6, 35.6, 32.9, 30.9, 27.3, 21.8, 21.4, 21.1 , 20.7, 19.4, 18.9, 18.8, 16.7, 14.2, 14.1. Description of smell

[0202] The smell impression of a series of different compounds according to formula (I) (examples 1- 5) as well as compounds not according to formula (I) but structurally closely related (comparative examples Ref.1 - Ref.5) have been characterized by a professional and experienced perfumer and compiled in table 1 .

[0203] Table 1 . Description of smell of different oximes according to the invention (7 to 5) and as comparison (Ref.1 to Ref.5). Table 1 . (cont.) Description of smell of different oximes according to the invention (1 to 5) and as comparison (Ref.1 to Ref.5).

[0204] In the molecules Ref.5 and Ref.6 no fig notes could be perceived. Description of smell of a fragrance composition

[0205] The fragrance compositions according to table 2 have been prepared.

[0206] Table 2. Fragrance composition.1Amounts in % by weight. The fragrance composition Ref. 7 is a reference fragrance composition.

[0207] By adding of 0.4 % by weight, relative to the total composition, of the respective oxime and by compensating this by a respective reduction of dipropylene glycol in the example to Ref.7 has yielded the compositions Ref. 8, Ref. 9, Ref. 10 (comparison), or 6 (according to the invention).

[0208] The fragrance compositions of table 2 have been admixed to an unperfumed standard shower gel at 1 % by weight.

[0209] The characteristic differences of smell impression of these shower gels have been assessed by a professional and experienced perfumer and are summarized in table 3.

[0210] Table 3. Characteristic differences in smell of fragrance compositions of table 2 used in a shower gel at 1 % by weight. Preparation of an eau de toilette comprising the invention’s composition of matter

[0211] The eau de toilette is prepared by adding 15% by weight, relative to the total weight of the eau de toilette, of the invention’s fragrance composition 6 into ethanol.

[0212] Preparation of a liquid detergent comprising the invention’s composition of matter

[0213] Table 4: Composition of the liquid detergent formulation

[0214] 1 ) Hostapur SAS 60; Origin: Clariant 2) Edenor K 12-18; Origin: Cognis

[0215] 3) Genapol LA 070; Origin: Clariant

[0216] 4) Origin: Genencor International

[0217] 5) Aculyn 88; Origin: Dow Chemical The liquid detergent is prepared by adding 0.1 to 2% by weight, relative to the total weight of the liquid detergent, of the invention’s composition 6 into the unperfumed liquid detergent formulation of Table 4 under gentle shaking.

[0218] Preparation of a fabric softener comprising the invention’s composition of matter

[0219] Table 5: Composition of the softener formulation

[0220] 1 ) Stepantex VL90 A Diester Quat; Origin: Stepan

[0221] 2) Proxel GXL; Origin: Arch

[0222] The softener is prepared by weighting Methyl bis[ethy I (tallowate)]-2- hydroxyethyl ammonium methyl sulfate which was heated at 65°C. Then Water and 1 ,2-benzisothiazolin-3-one are placed in the reactor and are heated at 65°C under stirring. To the above mixture is added Methyl bis[ethyl (tallowate)]-2- hydroxyethyl ammonium methyl sulfate. The mixture is stirred 15 minutes and CaC is added. Then 0.5 to 2% by weight, relative to the total weight of the softener, of the invention’s fragrance composition 6 is added. The mixture is stirred 15 minutes and is cooled down to room temperature under stirring (viscosity measure : result 35 + / - 5 mPas. (shear rate 106 sec-1 )). Preparation of a transparent isotropic shampoo comprising the invention’s composition of matter

[0223] Table 6: Composition of the transparent isotropic shampoo formulation

[0224] 1) llcare Polymer JR-400, Origin: Noveon

[0225] 2) Origin: Schweizerhall

[0226] 3) Glydant, Origin: Lonza

[0227] 4) Texapon NSO IS, Origin: Cognis

[0228] 5) Tego Betain F 50, Origin: Evonik

[0229] 6) Amphotensid GB 2009, Origin: Zschimmer & Schwarz

[0230] 7) Monomuls 90 L-12, Origin: Gruenau

[0231] 8) Nipagin Monosodium, Origin: NIPA

[0232] The shampoo is prepared by dispersed in water Polyquaternium-10. The remaining ingredients of phase A are mixed separately by addition of one after the other while mixing well after each adjunction. This pre-mix is added to the Polyquaternium-10 dispersion and mixed for another 5 min. Then, the premixed phase B and the premixed Phase C are added (Monomuls 90L-12 is heated to melt in Texapon NSO IS) while agitating. Phase D and Phase E are added while agitating. PH is adjusted with citric acid solution till pH: 5.5 - 6.0 leading to an unperfumed shampoo formula. The perfumed shampoo is prepared by adding 0.2 to 0.8% by weight, relative to the total weight of the shampoo, of the invention’s fragrance composition 6 into the unperfumed shampoo formulation of Table 6 under gentle shaking. Preparation of a structured shower gel comprising the invention’s composition of matter

[0233] Table 7: Composition of the shower gel formulation

[0234] 1 ) EDETA B POWDER; origin: BASF 2) CARBOPOL AQUA SF-1 POLYMER; origin: NOVEON

[0235] 3) ZETESOL AO 328 U; origin: ZSCHIMMER & SCHWARZ

[0236] 4) TEGO-BETAIN F 50; origin: GOLDSCHMIDT

[0237] 5) KATHON CG; origin: ROHM & HASS The shower gel is prepared by adding 0.5 to 1.5% by weight, relative to the total weight of the shower gel, of the invention’s fragrance composition 6 into the unperfumed shower gel formulation of Table 7 under gentle shaking. Preparation of a transparent shower gel comprising the invention’s composition of matter

[0238] Table 8: Composition of the transparent shower gel formulation

[0239] 1 ) EDETA B POWDER; origin: BASF 2) ZETESOL AO 328 U; origin: ZSCHIMMER & SCHWARZ

[0240] 3) TEGO-BETAIN F 50; origin: GOLDSCHMIDT

[0241] 4) MERQUAT 550; origin: LUBRIZOL

[0242] The transparent shower gel is prepared by adding 0.5 to 1.5% by weight, relative to the total weight of the shower gel, of the invention’s fragrance composition 6 into the unperfumed shower gel formulation of Table 8 under gentle shaking.

Claims

Claims1. A compound of the formula (I)R1represents either H or CH3; and R2represents either a methyl or an ethyl group or a CH=CH2 group, or any stereoisomer thereof; and the wavy line represents a nitrogen-oxygen bond which is either in the Z- or in the E-configuration.

2. The compound of the formula (I) according to claim 1 , characterized in that the formula (I) has 9 to 11 carbon atoms, preferably 11 carbon atoms.

3. The compound of the formula (I) according to claim 1 or 2, characterized in that the compound of the formula (I) is selected from the group consisting of the compounds of the formula (l-A), (l-B), (l-C), (l-D) and (l-E)or any stereoisomers thereof.

4. The compound of the formula (I) according to any of the preceding claims, characterized in that the compound of the formula (I) is a compound of the formula (l-B)5. A process of manufacturing a compound of the formula (I) according to any of the preceding claims by reacting a ketone of the formula (II)or any stereoisomer thereof; whereinR1represents either H or CH3; andR2represents either a methyl or an ethyl group or a CH=CH3 group; with a hydroxylamine or hydroxylamine salt or masked hydroxylamine in the presence of a base, particularly of an amine.

6. The process of claim 5, characterized in that the reaction between ketone of the formula (II) and the hydroxylamine or hydroxylamine salt is performed at a temperature of between 40 and 200°C, preferably between 50 and 150°C.

7. A composition comprising at least a compound of the formula(l) according to any of the preceding claims 1 to 4.

8. A perfuming composition comprising i) at least the compound of formula (I) according to any of the preceding claims 1 to 4;ii) at least one ingredient selected from the group consisting of a perfumery carrier and a perfumery base; and iii) optionally at least one perfumery adjuvant.

9. The perfuming composition according to claim 8, characterized in that the composition is a composition of daily use, particularly a cosmetic product or a grooming, fabric or home care product.

10. A perfumed consumer product comprising at least one compound of formula (I) according to any of the preceding claims 1 to 4, or a perfuming composition according to claim 8 or 9.11 . The perfumed consumer product according to claim 10, characterized in that the perfumed consumer product is a perfume, a fabric care product, a bodycare product, a cosmetic preparation, a skin-care product, an air care product or a home care product.

12. The perfumed consumer product according to claim 10 or 11 , characterized in that the perfumed consumer product is a fine perfume, a splash or eau de parfum, a cologne, a shave or after-shave lotion, a liquid or solid detergent optionally in the form of a pod or tablet, a laundry sheet, a soluble laundry sheet, a fabric softener, a liquid or solid scent booster, a dryer sheet, a fabric refresher, an ironing water, a paper, a bleach, a carpet cleaner, a curtaincare product, a shampoo, a leave-on or rinse-off hair conditioner, a coloring preparation, a color-care product, a hair shaping product, a dental care product, a disinfectant, an intimate care product, a hair spray, skin cream or lotion, a vanishing cream, a deodorant or antiperspirant, a hair remover, a tanning or sun or after sun product, a nail product, a skin cleansing, a makeup, a perfumed soap, a shower or bath mousse, oil or gel, a foot / hand care product, a hygiene product, an air freshener, a “ready to use” powdered air freshener, a mold remover, a furnisher care, a wipe, a dish detergent or hard-surface detergent, a leather care product, a car care product13. The use of the formula (I) according to any of the preceding claims 1 -4 to impart a fig odor to a chemical composition.

14. A method to confer or enhance or improve or modify the odor properties of a perfuming composition or of a perfumed article, which method comprises adding to said composition or article an effective amount of at least a compound of formula (I) according to any of the preceding claims 1-4.

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