Valley lily odorant

Abstract

The invention relates to the field of perfume industry. More specifically, the present invention relates to the use of a composition of matter comprising 3-(4-isopropyl-2-methylphenyl) propionaldehyde and 3-(2-isopropyl-4-methylphenyl) propionaldehyde, both aldehydes being useful perfuming ingredients of the aldehyde, floral type, as perfuming ingredient or for controlling arthropods. Thus, according to described herein, the invention comprises a composition of matter of the invention as a perfuming composition or part of a perfumed consumer product.

Description

Technical Field

[0001] The present invention relates to the field of perfumery. More specifically, the present invention relates to the use of a material composition comprising 3-(4-isopropyl-2-methylphenyl)propanal and 3-(2-isopropyl-4-methylphenyl)propanal as a perfuming ingredient or for controlling arthropods, these two aldehydes being useful perfuming ingredients of the aldehydic, floral type. Therefore, according to the present invention, the present invention comprises the material composition of the present invention as part of a perfuming composition or a perfuming consumer product. Background Art

[0002] One of the most sought after ingredients in the perfumery sector are those that impart a floral impression, especially the scent of lily of the valley. The value of this delicate floral note is enhanced by the observation that it is not retained by even the mildest extraction methods used to produce essential oils. The note is extremely popular and is used in a wide variety of perfumed consumer products. For decades, much effort has been devoted to the search for compounds that impart this very complex white floral scent, especially since the use of (2-methyl-3-[4-(2-methyl-2-n-propyl)phenyl]propanal, a trademark of Givaudan-Roure SA, Vergne, Switzerland), the latter represents one of the most valuable perfuming ingredients, with lily-of-the-valley and watery connotations, but has been restricted for various reasons.

[0003] There is a need to develop new perfuming ingredients that impart a floral odor note as close as possible to the natural smell of lily of the valley.

[0004] Helvetica Chimica Acta 1996 1095 reported 3-(4-isopropyl-2-methylphenyl)propanal and its analogs, among which 3-(4-(tert-butyl)-2-methylphenyl)propanal is considered to be a valuable odorant that can impart Lily of the valley aroma with a slight undertone of anise seed.

[0005] The present invention provides a novel composition of matter comprising 3-(4-isopropyl-2-methylphenyl)propanal and 3-(2-isopropyl-4-methylphenyl)propanal, providing a lily of the valley fragrance note which is very popular in the perfume industry. The prior art did not anticipate that the present composition could provide such a high performance and odor characteristics. Summary of the invention

[0006] It has been found that there is a surprising synergistic effect between 3-(4-isopropyl-2-methylphenyl)propanal and 3-(2-isopropyl-4-methylphenyl)propanal, resulting in a composition of matter according to the invention having an aldehyde / floral note combined with a green note.

[0007] Therefore, a first object of the present invention is to provide a material composition comprising 3-(4-isopropyl-2-methylphenyl)propanal and 3-(2-isopropyl-4-methylphenyl)propanal.

[0008] The composition of matter can be used as perfuming ingredient, for example to impart odor notes of the aldehydic, floral type.

[0009] According to any embodiment of the present invention, the composition of matter of the present invention may comprise at least 75% w / w 3-(4-isopropyl-2-methylphenyl)propanal, in particular 80% w / w 3-(4-isopropyl-2-methylphenyl)propanal, in particular 85% w / w 3-(4-isopropyl-2-methylphenyl)propanal, in particular 87% w / w 3-(4-isopropyl-2-methylphenyl)propanal, in particular 90% w / w 3-(4 -isopropyl-2-methylphenyl)propanal, in particular 95% w / w of 3-(4-isopropyl-2-methylphenyl)propanal, in particular 98% w / w of 3-(4-isopropyl-2-methylphenyl)propanal, in particular 99% w / w of 3-(4-isopropyl-2-methylphenyl)propanal, even more in particular 99.5% w / w of 3-(4-isopropyl-2-methylphenyl)propanal, the percentages being calculated relative to the total weight of the composition of matter.

[0010] According to any embodiment of the present invention, the material composition of the present invention may comprise up to 25% w / w of 3-(2-isopropyl-4-methylphenyl)propanal, in particular 20% w / w of 3-(4-isopropyl-2-methylphenyl)propanal, in particular 15% w / w of 3-(4-isopropyl-2-methylphenyl)propanal, in particular 10% w / w of 3-(2-isopropyl-4-methylphenyl)propanal, in particular 5% w / w of 3-(2-isopropyl-4-methylphenyl)propanal, in particular 2% w / w of 3-(2-isopropyl-4-methylphenyl)propanal, in particular 1% w / w of 3-(2-isopropyl-4-methylphenyl)propanal, even more in particular 0.5% w / w of 3-(2-isopropyl-4-methylphenyl)propanal, the percentages being calculated relative to the total weight of the material composition.

[0011] According to any embodiment of the present invention, the material composition of the present invention may contain 75% to 99.5% w / w of 3- (4-isopropyl-2-methylphenyl) propionaldehyde and 0.5% to 25% w / w of 3- (2-isopropyl-4-methylphenyl) propionaldehyde, the percentages being calculated relative to the total weight of the material composition. In particular, the material composition of the present invention may contain 80% to 99% w / w of 3- (4-isopropyl-2-methylphenyl) propionaldehyde and 1% to 20% w / w of 3- (2-isopropyl-4-methylphenyl) propionaldehyde, the percentages being calculated relative to the total weight of the material composition. In particular, the material composition of the present invention may contain 85% to 95% w / w of 3- (4-isopropyl-2-methylphenyl) propionaldehyde and 3% to 15% w / w of 3- (2-isopropyl-4-methylphenyl) propionaldehyde, the percentages being calculated relative to the total weight of the material composition. Even more particularly, the material composition of the present invention may comprise 88% to 95% w / w 3-(4-isopropyl-2-methylphenyl)propanal and 3% to 8% w / w 3-(2-isopropyl-4-methylphenyl)propanal, the percentages being calculated relative to the total weight of the material composition.

[0012] According to any embodiment of the present invention, the ratio of 3-(4-isopropyl-2-methylphenyl)propanal to 3-(2-isopropyl-4-methylphenyl)propanal is 85:15 to 99.5:0.5, even 90:10 to 99:1, even 92:8 to 98:2, even 94:6 to 98:2.

[0013] According to any embodiment of the present invention, the material composition of the present invention may also contain 3-(5-isopropyl-2-methylphenyl)propanal. In particular, the material composition of the present invention may contain up to 10% of 3-(5-isopropyl-2-methylphenyl)propanal, in particular, up to 8% of 3-(5-isopropyl-2-methylphenyl)propanal, in particular, up to 5% of 3-(5-isopropyl-2-methylphenyl)propanal, in particular, up to 3% of 3-(5-isopropyl-2-methylphenyl)propanal, in particular, up to 2% of 3-(5-isopropyl-2-methylphenyl)propanal, even more in particular, up to 1% of 3-(5-isopropyl-2-methylphenyl)propanal, the percentages being calculated relative to the total weight of the material composition.

[0014] As a specific example of a composition of matter of the present invention, there can be cited as a non-limiting example a composition of matter comprising 93% w / w of 3-(4-isopropyl-2-methylphenyl)propanal and 7% w / w of 3-(2-isopropyl-4-methylphenyl)propanal, the percentages being calculated relative to the total weight of the composition of matter.

[0015] 3-(2-isopropyl-4-methylphenyl)propionaldehyde is a new compound having the advantages explained above. Therefore, another object of the present invention is 3-(2-isopropyl-4-methylphenyl)propionaldehyde as a compound. 3-(2-isopropyl-4-methylphenyl)propionaldehyde can be used as a perfuming ingredient, for example to impart odor notes of the aldehydic, floral type.

[0016] As mentioned above, the present invention relates to the use of 3-(2-isopropyl-4-methylphenyl)propanal or 3-(5-isopropyl-2-methylphenyl)propanal or a composition of matter according to the present invention as a perfuming ingredient. In other words, the present invention relates to a method or process for imparting, enhancing, improving or modifying the odor characteristics of a perfuming composition or a perfumed article or surface, the method comprising adding to said composition or article an effective amount of 3-(2-isopropyl-4-methylphenyl)propanal or 3-(5-isopropyl-2-methylphenyl)propanal or a composition of matter according to the present invention, for example to impart a typical fragrance note thereto. It will be appreciated that the final hedonic effect may depend on the precise dosage and organoleptic properties of 3-(2-isopropyl-4-methylphenyl)propanal or 3-(5-isopropyl-2-methylphenyl)propanal or the material composition of the present invention, but in any event the addition of 3-(2-isopropyl-4-methylphenyl)propanal or 3-(5-isopropyl-2-methylphenyl)propanal or the material composition of the present invention will impart a typical flavor in the form of a note, touch or aspect to the final product depending on the dosage.

[0017] By “the use of 3-(2-isopropyl-4-methylphenyl)propanal or 3-(5-isopropyl-2-methylphenyl)propanal or a substance composition according to the invention”, it must also be understood here that is the use of any composition which contains 3-(2-isopropyl-4-methylphenyl)propanal or 3-(5-isopropyl-2-methylphenyl)propanal or a substance composition according to the invention and which can be advantageously used in the perfumery industry.

[0018] Said compositions, which in fact can advantageously be used as perfuming ingredients, are also an object of the present invention.

[0019] Therefore, another object of the present invention is a perfuming composition comprising:

[0020] i) 3-(2-isopropyl-4-methylphenyl)propanal or 3-(5-isopropyl-2-methylphenyl)propanal or at least one substance composition according to the invention as defined above as perfuming ingredient;

[0021] ii) at least one ingredient selected from the group consisting of a fragrance carrier and a fragrance base; and

[0022] iii) optionally, at least one flavor adjuvant.

[0023] By "perfume carrier" it is meant here a material which is practically neutral from a perfume point of view, ie which does not significantly alter the organoleptic properties of the perfuming ingredient. The carrier may be liquid or solid.

[0024] 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 the perfume industry. A detailed description of the nature and types of solvents commonly used in the perfume industry is not exhaustive. However, one may cite, as non-limiting examples, solvents such as butylene glycol or propylene glycol, glycerol, dipropylene glycol and its monoethers, 1,2,3-propanetriol triacetate, dimethyl glutarate, dimethyl adipate, 1,3-diacetoxyprop-2-yl acetate, diethyl phthalate, isopropyl myristate, (rosin resin, available from Eastman), benzyl benzoate, benzyl alcohol, 2-(2-ethoxyethoxy)-1-ethanol, triethyl citrate or mixtures thereof, which are most commonly used. Or solvents of natural origin such as glycerol or various vegetable oils such as palm oil, sunflower oil or linseed oil. For compositions containing both a fragrance carrier and a fragrance base, in addition to those specified above, other suitable fragrance carriers may also be ethanol, water / ethanol mixtures, limonene or other terpenes, isoparaffins, such as those sold under the trademark Those known (source: Exxon Chemical), or glycol ethers and glycol ether esters, such as those sold under the trademark Those known as (source: Dow Chemical Company), or hydrogenated castor oil, such as those sold under the trademark RH 40 is known per se (source: BASF).

[0025] Solid carrier refers to a kind of material, and some composition of perfuming composition or perfuming composition can be combined with it chemically or physically.Generally speaking, this type of solid carrier is used for stabilizing composition, or controls the evaporation rate of composition or some composition.Solid carrier is what is used in this field at present, and those skilled in the art know how to reach the desired effect.Yet, as the non-limiting example of solid carrier, absorbent glue or polymer or inorganic material can be enumerated, for example porous polymer, cyclodextrin, dextrin, maltodextrin, wood-based material, organic or inorganic gel, clay, gypsum, talcum or zeolite.

[0026] As other non-limiting examples of solid carriers, encapsulating materials can be cited. Examples of such materials may include wall-forming materials and plasticizers, such as glucose syrup, natural or modified starch, hydrocolloids, cellulose derivatives, polyvinyl acetate, polyvinyl alcohol, proteins or pectins, plant gums such as acacia gum (gum arabic), urea, sodium chloride, sodium sulfate, zeolite, sodium carbonate, sodium bicarbonate, clay, talc, calcium carbonate, magnesium sulfate, gypsum, calcium sulfate, magnesium oxide, zinc oxide, titanium dioxide, calcium chloride, potassium chloride, magnesium chloride, zinc chloride, carbohydrates, sugars such as sucrose, monosaccharides, disaccharides, trisaccharides 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, acrylamide, acrylates, polyacrylic acid and related substances, maleic anhydride copolymers, amine-functional polymers, vinyl ethers, styrene, polystyrene sulfonates, vinyl acid, ethylene glycol-propylene glycol block copolymers, vegetable gums, acacia gum, pectin, xanthan gum, alginates, carrageenan, citric acid or any water-soluble solid acid, fatty alcohol or fatty acid and mixtures thereof, or in references such as H. Scherz, Hydrokolloide: Stabilisatoren, Dickungs- und Geliermittel in Lebensmitteln, Band 2 der Schriftenreihe Lebensmittelchemie, Materials listed in Behr's Verlag GmbH & Co., Hamburg, 1996. Encapsulation is a process well known to the person skilled in the art and may be performed, for example, using techniques such as spray drying, agglomeration or extrusion; or consist of coating encapsulation including coacervation and complex coacervation techniques.

[0027] As non-limiting examples of solid supports, one may in particular cite core-shell capsules using resins of the aminoplast, polyamide, polyester, polyurea or polyurethane type or mixtures thereof (all said resins being well known to a person skilled in the art), by a phase separation process initiated using techniques such as polymerization, interfacial polymerization, coacervation or these techniques together (all said techniques having been described in the prior art), and optionally in the presence of polymeric stabilizers or cationic copolymers.

[0028] The resins may be produced by polycondensation of aldehydes such as formaldehyde, 2,2-dimethoxyacetaldehyde, glyoxal, glyoxylic acid or glycolaldehyde and mixtures thereof with amines such as urea, benzoguanamine, glycoluril, melamine, methylolmelamine, methylated methylolmelamine, guanazole, and the like and mixtures thereof. Alternatively, preformed resins may be used, such as those sold under the trademark (Source: Cytec Technology Corp.), (Source: Cytec TechnologyCorp.), or (Source: BASF) Those that are commercially available.

[0029] Other resins are obtained by mixing a polyol such as glycerol with a polyisocyanate such as 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 and trimethylolpropane (known under the trade name Known sources: those produced by polycondensation of Mitsui Chemicals), of which the trimer of xylylene diisocyanate with trimethylolpropane and the biuret of hexamethylene diisocyanate are preferred.

[0030] Some research literature related to the encapsulation of spices by condensation of amino resins, i.e. melamine-based resins, with aldehydes includes articles such as Acta Polymerica, 1989, vol. 40, pages 243, 325 and 683 and 1990, vol. 41, page 91, published by K. Dietrich et al. These articles have described various parameters that affect the preparation of such core-shell microcapsules according to prior art methods, which are also further detailed and exemplified in patent literature. US 4'396'670 of Wiggins Teape Group Limited is a relevant early example of the latter. Since then, many other authors have enriched the literature in this field, and it is not possible to cover all published progress here, but general knowledge of encapsulation technology is very important. More recent targeted publications also involve suitable uses of such microcapsules, representative articles such as K. Bruyninckx and M. Dusselier, ACS Sustainable Chemistry & Engineering, 2019, vol. 7, pages 8041-8054.

[0031] By "perfume base" it is meant here a composition comprising at least one perfuming co-ingredient.

[0032] The perfuming co-ingredient is not 3-(2-isopropyl-4-methylphenyl)propanal or 3-(5-isopropyl-2-methylphenyl)propanal or a composition of matter of the present invention. Furthermore, by "perfuming co-ingredient" it is meant here a compound which is used in a perfuming preparation or composition to impart a hedonic effect; i.e. primarily for imparting or regulating an odour. In other words, to be considered a perfuming co-ingredient such a co-ingredient must be recognized by a person skilled in the art as being able to impart or modify the odour of a composition in an active or pleasant manner, rather than merely having an odour. In addition to modifying or imparting an odour, a perfuming co-ingredient may impart additional benefits such as persistence, burst, malodour counteracting, antimicrobial action, antiviral action, microbial stability or pest control.

[0033] The nature and types of perfuming co-ingredients present in the base do not warrant a more detailed description here, which is in no way exhaustive, and a person skilled in the art will be able to choose them according to his general knowledge and according to the intended use or application and the desired organoleptic effect. In general, these perfuming co-ingredients belong to different chemical classes, such as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogen- or sulfur-containing heterocyclic compounds and essential oils, and may be of natural or synthetic origin.

[0034] In particular, one may cite the perfuming auxiliary ingredients usually used in perfume formulations, for example:

[0035] - Aldehyde aroma components: decanal, dodecanal, 2-methylundecane, 10-undecenal, octanal, nonanal and / or nonenal;

[0036] - Aromatic herbal ingredients: eucalyptus oil, camphor, eucalyptol, 5-methyltricyclo[6.2.1.0 2,7 ] undec-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 α-pinene;

[0037] - balsamic ingredients: coumarin, ethyl vanillin and / or vanillin;

[0038] - Citrus aroma ingredients: dihydromyrcenol, citral, orange oil, linalyl acetate, citronellyl nitrile, orange terpenes, limonene, 1-p-menthen-8-yl acetate and / or 1,4(8)-p-menthenadiene;

[0039] -Floral fragrance ingredients: methyl dihydrojasmonate, linalool, citronellol, phenylethyl alcohol, 3-(4-tert-butylphenyl)-2-methylpropanal, hexyl cinnamaldehyde, benzyl acetate, benzyl salicylate, tetrahydro-2-isobutyl-4-methyl-4(2H)-pyranol, β-ionone (β-violet ketone), 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-butene-1-one, (2E)-1-(2,6,6-trimethyl-2-cyclohexene-1-yl)-2-butene-1-one, (2E)-1-[2,6,6-trimethyl-3-cyclohexene-1-yl]-2-butene-1-one, (2E)-1-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2-butene-1-one, 2,5-dimethyl-2-indanemethanol, 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-methyl propanal, tricyclodecenyl acetate, geraniol, p-menth-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, methyl dihydrojasmonate, 3-methyl-5-phenyl 1-Hydroxy-1-pentanol, tricyclodecenyl propionate, geranyl acetate, tetrahydrolinalool, cis-7-p-menthol, (S)-2-(1,1-dimethylpropoxy)propyl propionate, 2-methoxynaphthalene, 2,2,2-trichloro-1-phenylethyl acetate, 4 / 3-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carbaldehyde, amylcinnamaldehyde, 8-decene-5-lactone, 4-phenyl-2-butanone, isononyl acetate, 4-(1,1-dimethylethyl)-1-cyclohexyl acetate, tricyclodecenyl isobutyrate, and / or a mixture of methylionone isomers;

[0040] - Fruity aroma ingredients: γ-undecalactone, 2,2,5-trimethyl-5-pentylcyclopentanone, 2-methyl-4-propyl-1,3-oxathiacyclopentane, 4-decanoic acid, ethyl 2-methyl-valerate, hexyl acetate, ethyl 2-methylbutyrate, γ-nonalactone, 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-cyclohexanedicarboxylate;

[0041] - Green fragrance ingredients: 2-methyl-3-hexanone (E)-oxime, 2,4-dimethyl-3-cyclohexene-1-carbaldehyde, 2-tert-butyl-1-cyclohexyl acetate, styryl acetate, (2-methylbutoxy) allyl 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;

[0042] - Musk ingredients: 1,4-dioxa-5,17-cycloheptadecanedione, (Z)-4-cyclopentadecen-1-one, 3-methylcyclopentadecen-1-one, 1-oxa-12-cyclohexadecene-2-one, 1-oxa-13-cyclohexadecene-2-one, (9Z)-9-cycloheptadecene-1-one, 2-{1S)-1-[(1R)-3,3-dimethylcyclohexyl]ethoxy}-2-oxoethyl propionate, 3-methyl-5-cyclohexane Pentadecene-1-one, 4,6,6,7,8,8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta[g]-2-benzopyran, (1S,1'R)-2-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxy]-2-methylpropyl propionate, oxacyclohexadecane-2-one and / or (1S,1'R)-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxycarbonyl]methyl propionate;

[0043] - Woody components: 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[2,9'-tricyclo[6.2.1.0 2,7 ] 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-naphthyl)-1-ethanone, patchouli oil, terpene fraction of patchouli oil, (Source: 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;

[0044] -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, piperonal, 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-naphthol, 1-phenylvinyl acetate, 6-methyl-7-oxa-1-thia-4-azaspiro[4.4]nonane and / or 3-(3-isopropyl-1-phenyl)butanal.

[0045] The perfume base according to the invention may not be limited to the above-mentioned perfuming co-ingredients, and many other such co-ingredients are anyway listed in references such as S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA or its updated editions, or other works of similar nature, as well as a large number of patent documents in the field of perfumery. It should also be understood that the co-ingredients may also 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 pro-fragrances 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, 3-(dodecylsulfonyl)-1-(2,6,6-trimethylcyclohex-3-en-1-yl)butan-1-one , linear polysiloxane copolymer of (3-mercaptopropyl)(methyl)dimethoxysilane, 2-(dodecylthio)octane-4-one, 2-(dodecylsulfonyl)octane-4-one, 4-oxooctane-2-yl dodecanoate, 2-phenylethyl oxy(phenyl)acetate, 3,7-dimethyloctane-2,6-dien-1-yl oxy(phenyl)acetate, (Z)-hex-3-en-1-yl oxy(phenyl)acetate, 3,7-dimethyl-2,6-octadien-1-yl hexadecanoate, bis(3,7 -dimethyl oct-2,6-dien-1-yl) ester, hexadecanoic acid (2E,6Z)-2,6-nonadien-1-yl ester, tetradecanoic acid (2E,6Z)-2,6-nonadien-1-yl ester, dodecanoic acid (2E,6Z)-2,6-nonadien-1-yl ester, (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-(( 1-((2-methylundec-1-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-phenylethoxyprop-1-en-2-yl)benzene, 1-methyl-4-(1-phenylethoxyprop-1-en-2-yl)benzene, 2-(1-phenylethoxyprop-1-en-2-yl)naphthalene, (2-phenylethoxyvinyl)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-phenylethoxyprop-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-phenylethoxyallyl)benzene, (2-((2- benzene, 1-isopropyl-4-methyl-2-((2-pentylcyclopentylidene)methoxy)benzene, 2-methoxy-1-((2-pentylcyclopentylidene)methoxy)-4-propylbenzene, 2-ethoxy-1-((2-methoxy-2-phenylvinyl)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.

[0046] By "perfume adjuvant" it is meant here ingredients capable of imparting additional added benefits, such as colour, specific lightfastness, chemical stability, etc. A detailed description of the nature and types of adjuvants commonly used in perfuming compositions cannot be exhaustive, but it must be mentioned that said ingredients are well known to the person skilled in the art. The following may be cited as specific non-limiting examples: viscosity agents (e.g. surfactants, thickeners, gelling agents and / or rheology modifiers), stabilizers (e.g. preservatives, antioxidants, heat / light and / or buffers or chelating agents, such as BHT), colorants (e.g. dyes and / or pigments), preservatives (e.g. antibacterial or antimicrobial or antifungal or anti-irritants), abrasives, skin cooling agents, fixatives, insect repellents, ointments, vitamins and mixtures thereof. A "fixative", also called a "modifier", is understood here as an agent having the ability to influence the way in which an observer or user perceives the odour of a composition into which it is incorporated, in particular the rate of evaporation and the intensity, over time, compared to the same perception without the modifier. In particular, the conditioning agent allows to prolong the time of perceiving its fragrance. Non-limiting examples of suitable conditioning agents may include methyl glucoside polyol; ethyl glucoside polyol; propyl glucoside polyol; isocetyl alcohol; PPG-3 myristyl ether; neopentyl glycol di(ethylhexanoate); 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; polyglyceryl-4 ether; isoceteth-5; isocetyl Isoceteth-7, Isoceteth-10; Isoceteth-12; Isoceteth-15; Isoceteth-20; Isoceteth-25; Isoceteth-30; Disodium Lauroamphodipropionate; Hexaethylene Glycol Monododecyl Ether; and mixtures thereof; Neopentyl Glycol Diisononanoate; Cetearyl Ethylhexanoate; Panthenol Ethyl Ether, DL-Panthenol, Hexadecyl N-nonanoate, Hexadecyl N-nonanoate, Fragrance Procurators, Cyclodextrins, Encapsulating Agents, and combinations thereof. Up to 20% by weight of the conditioning agent may be incorporated into the perfumed consumer product, based on the total weight of the perfumed composition.

[0047] It will be appreciated that a person skilled in the art is fully capable of designing the best formulation for the desired effect simply by applying standard knowledge in the field and mixing the above-mentioned components of the perfuming composition by trial and error.

[0048] In addition to perfuming compositions comprising at least 3-(2-isopropyl-4-methylphenyl)propanal or at least 3-(5-isopropyl-2-methylphenyl)propanal or at least one composition of matter according to the invention, at least one perfume carrier, at least one perfume base and optionally at least one perfume adjuvant, an inventive composition consisting of at least 3-(2-isopropyl-4-methylphenyl)propanal or at least 3-(5-isopropyl-2-methylphenyl)propanal or at least one composition of matter according to the invention and at least one perfume carrier is also a particular embodiment of the invention.

[0049] According to a particular embodiment, the perfuming composition is in the form of microcapsules, preferably in the form of a microcapsule slurry, comprising at least 3-(2-isopropyl-4-methylphenyl)propanal or at least 3-(5-isopropyl-2-methylphenyl)propanal or at least one composition of matter according to the invention. In one embodiment, 3-(2-isopropyl-4-methylphenyl)propanal or 3-(5-isopropyl-2-methylphenyl)propanal or the composition of matter according to the invention is encapsulated in core-shell microcapsules, wherein 3-(2-isopropyl-4-methylphenyl)propanal or 3-(5-isopropyl-2-methylphenyl)propanal or the composition of matter according to the invention is contained in a core surrounded by a shell. In one embodiment, the shell of the microcapsules protects 3-(2-isopropyl-4-methylphenyl)propanal or 3-(5-isopropyl-2-methylphenyl)propanal or the composition of matter according to the invention from environmental influences. The shell is made of a material capable of releasing 3-(2-isopropyl-4-methylphenyl)propionaldehyde or 3-(5-isopropyl-2-methylphenyl)propionaldehyde or a composition of matter according to the invention. In one embodiment, the shell is made of a material capable of releasing 3-(2-isopropyl-4-methylphenyl)propionaldehyde or 3-(5-isopropyl-2-methylphenyl)propionaldehyde or a composition of matter according to the invention upon rupture of the shell and / or by diffusion through the shell. Methods for preparing said microcapsules are well known to those skilled in the art. In addition to 3-(2-isopropyl-4-methylphenyl)propionaldehyde or 3-(5-isopropyl-2-methylphenyl)propionaldehyde or a composition of matter according to the invention, the core of the core-shell microcapsule may also 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 core-shell microcapsule slurry comprising at least 3-(2-isopropyl-4-methylphenyl)propionaldehyde or 3-(5-isopropyl-2-methylphenyl)propionaldehyde or at least one composition of matter according to the invention may be dispersed in at least one liquid carrier as defined above. The liquid carrier may further comprise 3-(2-isopropyl-4-methylphenyl)propanal or 3-(5-isopropyl-2-methylphenyl)propanal or a composition of matter according to the invention and / or at least one perfuming co-ingredient as defined above.

[0050] According to a particular embodiment, the shell of the microcapsule comprises a material selected from the group consisting of polyureas, polyurethanes, polyamides, polyesters, poly(meth)acrylates (i.e. polyacrylates and / or polymethacrylates), polysiloxanes, polycarbonates, polysulfonamides, polymers of urea and formaldehyde, polymers of melamine and formaldehyde, polymers of melamine and urea, or polymers of melamine and glyoxal, and mixtures thereof. The shell may also be composite, i.e. organic-inorganic, such as a composite shell consisting of at least two types of crosslinked inorganic particles, or a shell resulting from the hydrolysis and condensation reaction of a polyalkoxysilane macromer composition.

[0051] According to a particular embodiment, core-shell microcapsules can also be obtained by using different or more than one encapsulation method.

[0052] In a preferred embodiment, the shells of the microcapsules may each independently be selected from aminoplast, polyamide, polyester, polyurea and polyurethane shells and mixtures thereof.

[0053] In a particular embodiment, the shell of the microcapsules comprises an aminoplast copolymer, such as melamine-formaldehyde or urea-formaldehyde or crosslinked melamine-formaldehyde or melamine-glyoxal.

[0054] In a particular embodiment, the shell of the microcapsule is polyurea-based, made of, for example, but not limited to, isocyanate-based monomers and amine-containing crosslinking agents such as guanidine carbonate and / or guanazole. Certain polyurea microcapsules comprise a polyurea wall, which is a polymeric reaction product between at least one polyisocyanate containing at least two isocyanate functional groups and at least one reactant selected from amines (e.g., water-soluble guanidine salts and guanidine); a colloidal stabilizer or emulsifier; and an encapsulated fragrance. However, the use of amines can be omitted.

[0055] In a specific embodiment, the colloidal stabilizer comprises an aqueous solution of 0.1% to 0.4% polyvinyl alcohol, 0.6% to 1% of a cationic copolymer of vinyl pyrrolidone and quaternized vinyl imidazole (all percentages are defined relative to the total weight of the colloidal stabilizer). In a specific embodiment, the emulsifier is an anionic or amphiphilic biopolymer, which can be selected, for example, from the group consisting of gum arabic, soy protein, gelatin, sodium caseinate, and mixtures thereof.

[0056] In one particular embodiment, the shell of the microcapsule is polyurethane based, made from, for example but not limited to, polyisocyanates and polyols, polyamides, polyesters, and the like.

[0057] In a particular embodiment, the microcapsules have a polymer shell produced by complex coacervation, wherein the shell may be crosslinked.

[0058] In a specific embodiment of the core-shell microcapsule, the core-shell microcapsule comprises an oil-based core, which comprises a hydrophobic active substance, preferably at least 3-(2-isopropyl-4-methylphenyl)propanal or 3-(5-isopropyl-2-methylphenyl)propanal or at least one material composition of the present invention, 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, and the second material is a polymeric material.

[0059] In a specific embodiment, the weight ratio between the first material and the second material is 50:50 to 99.9:0.1.

[0060] In a particular embodiment, the coacervate comprises a first polyelectrolyte, preferably selected from proteins (e.g. gelatin), polypeptides or polysaccharides (e.g. chitosan), most preferably gelatin, and a second polyelectrolyte, preferably alginate, cellulose derivatives, guar gum, pectinate, carrageenan, polyacrylic acid and methacrylic acid or xanthan gum, or a vegetable gum such as gum acacia (gum arabic), most preferably gum arabic.

[0061] The first coacervate material can be hardened chemically using a suitable cross-linking agent such as glutaraldehyde, glyoxal, formaldehyde, tannic acid, or genipin, or can be hardened enzymatically using an enzyme such as transglutaminase.

[0062] 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, polymers of melamine and formaldehyde, polymers of melamine and urea, or polymers of melamine and glyoxal, and mixtures thereof, preferably polyurea and / or polyurethane. The second material is preferably present in an amount of less than 3 wt%, preferably less than 1 wt%, based on the total weight of the microcapsule slurry.

[0063] The preparation of aqueous dispersion / slurry of core-shell microcapsules is well known to those skilled in the art. In a specific embodiment, the microcapsule wall material may include any suitable resin, especially including melamine, glyoxal, polyurea, polyurethane, polyamide, polyester, etc. Suitable resins include the reaction product of aldehydes and amines, and suitable aldehydes include formaldehyde and glyoxal. Suitable amines include melamine, urea, benzoguanamine, glycoluril and their mixtures. Suitable melamines include methylol melamine, methylated methylol melamine, imino melamine and their mixtures. Suitable ureas include dimethylol urea, methylated dimethylol urea, urea-resorcinol and their mixtures. Suitable materials for manufacture can be obtained from one or more of the following companies: Solutia Inc. (St. Louis, Missouri, USA), Cytec Industries (West Patterson, New Jersey, USA), Sigma-Aldrich (St. Louis, Missouri, USA).

[0064] In a specific embodiment of the core-shell microcapsule, the core-shell microcapsule comprises:

[0065] an oil-based core comprising a hydrophobic active substance, preferably 3-(2-isopropyl-4-methylphenyl)propanal or 3-(5-isopropyl-2-methylphenyl)propanal or at least one substance composition according to the invention,

[0066] - Optionally, an inner shell made from polymerized multifunctional monomers;

[0067] - A biopolymer shell comprising proteins, wherein at least one of the proteins is cross-linked.

[0068] According to a specific embodiment, the protein is selected from the group consisting of milk protein, caseinate such as sodium caseinate or calcium caseinate, casein, whey protein, hydrolyzed protein, gelatin, gluten, pea protein, soy protein, silk protein and mixtures thereof. Among them, sodium caseinate is preferred, and sodium caseinate is most preferred.

[0069] According to a specific embodiment, the protein comprises sodium caseinate and globular proteins, preferably selected from the group consisting of whey protein, beta-lactoglobulin, ovalbumin, bovine serum albumin, vegetable proteins and mixtures thereof.

[0070] The protein is preferably a mixture of sodium caseinate and whey protein.

[0071] According to a specific embodiment, the biopolymer shell comprises cross-linked proteins selected from the group consisting of sodium caseinate and / or whey proteins.

[0072] According to a particular embodiment, the microcapsule slurry comprises at least one microcapsule made of:

[0073] an oil-based core comprising a hydrophobic active substance, preferably 3-(2-isopropyl-4-methylphenyl)propanal or 3-(5-isopropyl-2-methylphenyl)propanal or at least one substance composition according to the invention,

[0074] - an inner shell made from polymerized polyfunctional monomers; preferably a polyisocyanate having at least two isocyanate functional groups;

[0075] - a biopolymer shell comprising proteins, wherein at least one of the proteins is cross-linked; wherein the proteins preferably comprise a mixture comprising sodium caseinate and globular proteins, preferably whey proteins;

[0076] - Optionally, at least one outer mineral layer.

[0077] According to one embodiment, the sodium caseinate and / or whey protein are cross-linked proteins.

[0078] The weight ratio between sodium caseinate and whey protein is preferably from 0.01 to 100, preferably from 0.1 to 10, more preferably from 0.2 to 5.

[0079] In a particular embodiment, the microcapsules are single-shell aminoplast core-shell microcapsules obtainable by a process comprising the steps of:

[0080] 1) mixing a fragrance oil with at least one polyisocyanate having at least two isocyanate functional groups to form an oil phase;

[0081] 2) dispersing or dissolving an aminoplast resin and an optional stabilizer in water to form an aqueous phase;

[0082] 3) preparing an oil-in-water dispersion by mixing an oil phase and an aqueous phase, wherein the average droplet size is 1 to 100 microns;

[0083] 4) performing a curing step to form the wall of the microcapsule; and

[0084] 5) Optionally, the final dispersion is dried to obtain dry core-shell microcapsules.

[0085] In a specific embodiment, the core-shell microcapsules are formaldehyde-free capsules. A typical method for preparing a slurry of aminoplast formaldehyde-free microcapsules comprises the following steps:

[0086] 1) preparing an oligomeric composition comprising the reaction product of, or an oligomeric composition obtained by reacting together:

[0087] a. a polyamine component in the form of melamine or a mixture of melamine and at least one C1-C4 compound comprising two NH2 functional groups;

[0088] b. Glyoxal, C 4-6 The aldehyde component is in the form of a mixture of 2,2-dialkoxyacetaldehyde and optionally glyoxylate, the glyoxal / C 4-6 The molar ratio of 2,2-dialkoxyethanol is 1 / 1 to 10 / 1; and

[0089] c. Protonic acid catalyst;

[0090] 2) preparing an oil-in-water dispersion wherein the droplet size is from 1 to 600 microns and comprising:

[0091] a.Oil;

[0092] b. Water medium

[0093] c. at least one oligomeric composition as obtained in step 1;

[0094] d. at least one cross-linking agent selected from the group consisting of:

[0095] i.C4-C 12 Aromatic or aliphatic di- or triisocyanates and their biuret, triuret, trimer, trimethylolpropane adducts and mixtures thereof; and / or

[0096] ii. a di- or tri-oxirane compound of the formula

[0097] Q-(Oxiran-2-ylmethyl) m

[0098] wherein m represents 2 or 3, Q represents optionally containing 2 to 6 nitrogen and / or

[0099] or a C2-C6 group of an oxygen atom;

[0100] e. Optionally, a C1-C4 compound comprising two NH2 functional groups;

[0101] 3) heating the dispersion;

[0102] 4) Cooling the dispersion.

[0103] The above method is described in more detail in WO 2013 / 068255.

[0104] In a specific embodiment of the core-shell microcapsule, the core-shell microcapsule is a polyamide core-shell polyamide microcapsule comprising:

[0105] an oil-based core comprising a hydrophobic active substance, preferably 3-(2-isopropyl-4-methylphenyl)propanal or 3-(5-isopropyl-2-methylphenyl)propanal or at least one substance composition according to the invention, and

[0106] - a polyamide shell comprising or obtainable from:

[0107] ·Acid chloride,

[0108] a first amino compound, and

[0109] A second amino compound.

[0110] According to a particular embodiment, the polyamide core-shell microcapsules comprise:

[0111] an oil-based core comprising a hydrophobic active substance, preferably 3-(2-isopropyl-4-methylphenyl)propanal or 3-(5-isopropyl-2-methylphenyl)propanal or at least one substance composition according to the invention, and

[0112] - a polyamide shell comprising or obtainable from:

[0113] Acid chloride, preferably in an amount of 5 to 98%, preferably 20 to 98%, more preferably 30 to 85% w / w;

[0114] The first amino compound is preferably present in an amount of 1% to 50% w / w, preferably 7 to 40%

[0115] w / w;

[0116] The second amino compound is preferably present in an amount of 1% to 50% w / w, preferably 2 to 25%

[0117] w / w;

[0118] • Stabilizer, preferably a biopolymer, preferably in an amount of 0 to 90%, preferably 0.1 to 75%, more preferably 1 to 70%.

[0119] According to a particular embodiment, the polyamide core-shell microcapsules comprise:

[0120] an oil-based core comprising a hydrophobic active substance, preferably 3-(2-isopropyl-4-methylphenyl)propanal or at least one substance composition according to the invention, and

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

[0122] ·Acid chloride,

[0123] a first amino compound, which is an amino acid, preferably selected from the group consisting of L-lysine, L-arginine, L-histidine, L-tryptophan and / or mixtures thereof,

[0124] a second amino compound selected from the group consisting of ethylenediamine, diethylenetriamine, cystamine and / or mixtures thereof, and

[0125] - A biopolymer selected from the group consisting of casein, sodium caseinate, bovine serum albumin, whey protein and / or mixtures thereof.

[0126] The first amino compound may be different from the second amino compound.

[0127] Typically, the method for preparing polyamide-based microcapsules comprises the following steps:

[0128] a) dissolving at least one acid chloride in a hydrophobic material, preferably a fragrance, to form an oil phase;

[0129] b) dispersing the oil phase obtained in step a) into the aqueous phase comprising the first amino compound to form an oil-in-water emulsion;

[0130] c) performing a curing step to form polyamide microcapsules in the form of a slurry;

[0131] wherein a stabilizer is added to the oil phase and / or the water phase, and

[0132] Therein, at least one second amino compound is added to the aqueous phase before forming the oil-in-water emulsion and / or to the oil-in-water emulsion obtained after step b).

[0133] In a particular embodiment, the shell of the microcapsule is polyurea-based or polyurethane-based. Examples of methods for preparing polyurea-based and polyurethane-based microcapsule slurries are described, for example, in WO2007 / 004166, EP2300146, EP2579976. Typically, the method for preparing a polyurea-based or polyurethane-based microcapsule slurry comprises the following steps:

[0134] a) dissolving at least one polyisocyanate having at least two isocyanate groups in oil to form an oil phase;

[0135] b) preparing an aqueous solution of an emulsifier or a colloid stabilizer to form an aqueous phase;

[0136] c) adding the oil phase to the water phase to form an oil-in-water dispersion wherein the average droplet size is from 1 to 500 μm, preferably from 5 to 50 μm; and

[0137] d) applying conditions sufficient to initiate interfacial polymerization and form microcapsules in the form of a slurry.

[0138] In a specific embodiment, the microcapsules can be in powder form, which can be obtained by subjecting the microcapsules slurry to a drying step such as spray drying to provide the microcapsules as is, i.e., in powder form. It should be understood that any standard method for carrying out this drying known to those skilled in the art is also applicable. In particular, the slurry can be spray dried to provide microcapsules in powder form preferably in the presence of a polymeric carrier material such as polyvinyl acetate, polyvinyl alcohol, dextrin, natural or modified starch, gum arabic, vegetable gum, pectin, xanthan gum, alginate, carrageenan or a cellulose derivative.

[0139] However, other drying methods may also be cited, such as extrusion, coating, spray granulation, fluidized bed process, or even drying at room temperature using materials (carrier, desiccant) that meet specific criteria as disclosed in WO2017 / 134179.

[0140] According to a particular embodiment, the above composition comprises more than one composition of matter according to the invention, since it enables the perfumer to prepare blends, fragrances having odor notes of various compositions of matter according to the invention, thus creating new building blocks for creative purposes.

[0141] For the sake of clarity, it is also understood that any mixture resulting directly from a chemical synthesis in which the compounds of the invention are used as starting material, intermediate or end product, such as a reaction medium without sufficient purification, cannot be considered as a perfuming composition according to the invention, as long as said mixture does not provide the compounds of the invention in a form suitable for use in perfumery. Therefore, unpurified reaction mixtures are generally excluded from the present invention, unless otherwise stated.

[0142] The composition of matter or 3-(2-isopropyl-4-methylphenyl)propanal or 3-(5-isopropyl-2-methylphenyl)propanal according to the invention can also be advantageously used in all areas of modern perfumery, i.e. in fine perfumes or functional perfumes, to actively impart or modify the odor of a consumer product to which 3-(2-isopropyl-4-methylphenyl)propanal or 3-(5-isopropyl-2-methylphenyl)propanal or the composition of matter according to the invention has been added. Therefore, another object of the present invention is a perfumed consumer product comprising, as a perfuming ingredient, 3-(2-isopropyl-4-methylphenyl)propanal or 3-(5-isopropyl-2-methylphenyl)propanal or at least one composition of matter according to the invention as defined above.

[0143] The compound according to the invention or the composition of matter according to the invention can be added as such or as part of a perfuming composition according to the invention.

[0144] For the sake of clarity, a "perfumed consumer product" is a consumer product that provides a pleasant perfuming effect at least to the surface or space to which it is applied, such as the skin, hair, textiles or household surfaces. In other words, a perfumed consumer product according to the invention is a perfumed consumer product comprising a functional formulation, and optionally additional benefit agents corresponding to the desired consumer product, and an olfactory effective amount of at least one compound according to the invention or a composition of matter according to the invention. For the sake of clarity, the perfumed consumer product is a non-edible product.

[0145] The nature and type of ingredients of perfumed consumer products do not warrant a more detailed description here, which is in no way exhaustive, the skilled person being able to choose them on the basis of his general knowledge and according to the characteristics of the product in question and the desired effect.

[0146] Non-limiting examples of suitable perfumed consumer products include perfumes, such as fine perfumes, splash perfumes or eau de perfumes, colognes or shaving lotions or aftershaves; fabric care products, such as liquid or solid detergents, fabric softeners, liquid or solid fragrance enhancers, dryer sheets, and the like, optionally in capsule or tablet form. hair care products (e.g. shampoos, leave-on or rinse-off hair conditioners, dye preparations (dyes) or hair sprays (hair gels), color care products, hair styling products, dental care products), disinfectants, intimate care products; beauty preparations (e.g. skin creams or lotions, vanishing creams or body fragrances (deodorants) or antiperspirants (e.g. sprays or roll-ons)), depilatories, tanning products, sunscreens or after-sun products , nail products, skin cleansers, cosmetics); or skin care products (e.g. soap, shower or bath mousse, bath oil or shower gel, or hygiene products or foot / hand care products); air care products, such as air fresheners or "ready-to-use" powder air fresheners, which can be used in domestic spaces (rooms, refrigerators, cupboards, shoes or cars) and / or public spaces (lobbies, hotels, shopping malls, etc.); or home care products, such as mildew removers, furniture care agents, wipes, dishwashing detergents or detergents for hard surfaces (e.g. floor, bathroom, sanitary ware or window cleaning); leather care products; car care products, such as polishes, waxes or plastic cleaners.

[0147] According to any embodiment of the invention, the perfumed consumer product of the invention is characterized by a pH of 1 or higher. In particular, the perfumed consumer product of the invention has a pH of 1 to 12, or of 1 to 8. Even more particularly, the perfumed consumer product of the invention has a pH of 1 to 6.

[0148] According to a particular embodiment, the perfumed consumer product of the present invention is in the form of a personal care, home care or fabric care consumer product comprising ingredients commonly found 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 ingredients of perfumed consumer products are surfactants and / or softener ingredients, which are capable of cleaning and / or softening fabrics and / or textiles of various natures, such as clothing, curtain fabrics, carpets and furniture fabrics, etc., or other household surfaces, skin or hair, usually in large amounts of water or in water-based solvents. Therefore, the amount of water in these preparations is usually between 50% and 99% by weight of the perfumed consumer product, with the exception of soaps or solid detergents, in which the amount of water is at most 20%.

[0149] While a more detailed description of such fabric cleaning and / or softening bases is not warranted here, many descriptions of current liquid bases can be found in the patent and other relevant literature on detergents / fabric softeners, such as the textbook "Détergents et Produits de Soins Corporels" by Louis Ho Tan Tai, especially Chapters 1 to 7, Dunod, Paris, 1999, or any other similar and / or more recent textbooks related to the formulation of liquid softeners and multi-purpose cleaners. Patent publication WO 2010 / 105873 is also cited as an example, as it describes typical current ingredients (except perfume) for such liquid products, especially on pages 9 to 21. Of course, many other examples of liquid detergent and / or fabric softener bases can be found in the literature. Any such liquid base, i.e., liquid fabric cleaners or conditioners and / or multi-purpose cleaners, can be used in the compositions described herein.

[0150] According to a particular embodiment of the invention, the perfumed consumer product of the invention is a liquid fabric softener comprising a fabric softener active base in an amount of 85 to 100% by weight, based on the total weight of the perfumed consumer product. The main component of the fabric softener active base is water or a water-based solvent. The fabric softener active base may comprise dialkyl quaternary ammonium salts, dialkyl ester quaternary ammonium salts, Hamburg ester quaternary ammonium salts, triethanolamine quaternary ammonium salts, silicone resins and mixtures thereof. Optionally, the fabric softener active base of the composition may also comprise a viscosity modifier in an amount of 0.05 to 1% by weight, based on the total weight of the liquid base; preferably selected from calcium chloride.

[0151] According to a particular embodiment of the invention, the perfumed consumer product of the invention is a universal cleaner comprising an amount of 85 to 100% by weight of an active base for universal cleaners, based on the total weight of the perfumed consumer product. The main component of the active base for universal cleaners is water or a water-based solvent. The universal active base may comprise linear alkylbenzene sulfonate (LAS) in an amount of 1% to 2%, a nonionic surfactant in an amount of 2% to 4% and an acid, such as citric acid, in an amount of 0.1% to 0.5%.

[0152] According to a particular embodiment of the invention, the perfumed consumer product of the invention is a liquid detergent comprising a liquid detergent active base in an amount of 85 to 100% by weight, based on the total weight of the perfumed consumer product. The main component of the liquid detergent active base is water or a water-based solvent. The liquid detergent active base may comprise an anionic surfactant such as alkylbenzene sulfonate (ABS), linear alkylbenzene sulfonate (LAS), secondary alkyl sulfonate (SAS), primary alcohol sulfate (PAS), lauryl ether sulfate (LES), sodium lauryl ether sulfate (SLES), methyl ester sulfonate (MES), and a nonionic surfactant such as alkylamines, alkanolamides, fatty alcohol poly(ethylene glycol) ethers, fatty alcohol ethoxylates (FAE), ethylene oxide (EO) and propylene oxide (PO) copolymers, amine oxides, alkyl polyglucosides, alkyl polyglucamides; or mixtures thereof.

[0153] According to a particular embodiment of the invention, the perfumed consumer product of the invention is a solid detergent comprising a solid detergent active base in an amount of 85 to 100% by weight, based on the total weight of the perfumed consumer product. The solid detergent active base may comprise at least one surfactant selected from the group consisting of anionic, nonionic, cationic, zwitterionic surfactants and mixtures thereof. The surfactant in the solid detergent active base is preferably selected from the group consisting of linear olefin benzene sulfonates (LABS), sodium laureth sulfate, sodium lauryl ether sulfate (SLES), sodium lauryl sulfate (SLS), alpha-olefin sulfonates (AOS), methyl ester sulfonates (MES), alkyl polyglucosides (APG), primary alcohol ethoxylates, in particular lauryl alcohol ethoxylate (LAE), primary alcohol sulfonates (PAS), soaps and mixtures thereof. The solid detergent active base may contain additional ingredients commonly used in powdered detergent consumer products, selected from the group consisting of: bleaching agents such as TAED (tetraacetylethylenediamine); buffering agents; builders, such as zeolite, sodium carbonate or mixtures thereof; soil release agents or soil suspension polymers; granular enzyme particles, such as cellulase, lipase, protease, mannanase, pectinase or mixtures thereof; corrosion inhibitors; defoamers; suds suppressors; dyes; fillers, such as sodium silicate, sodium sulfate or mixtures thereof; sources of hydrogen peroxide, such as sodium percarbonate or sodium perborate; and mixtures thereof.

[0154] According to a particular embodiment of the invention, the perfumed consumer product of the invention is a shampoo or shower gel comprising a shampoo or shower gel active base in an amount of 85 to 100% by weight, based on the total weight of the perfumed consumer product. The main component of the shampoo or shower gel active base is water or a water-based solvent. The shampoo or shower gel active base may comprise sodium alkyl ether sulfate, ammonium alkyl ether sulfate, alkyl amphoacetate, cocamidopropyl betaine, cocamide MEA, alkyl glucoside and amino acid-based surfactants.

[0155] According to a particular embodiment of the invention, the perfumed consumer product of the invention is a soap bar comprising a soap active base in an amount ranging from 85 to 100% by weight, based on the total weight of the perfumed consumer product. The soap bar active base may comprise a salt of a weak acid, typically a salt of a weak acid (which may be a fatty acid) and a strong base such as sodium hydroxide.

[0156] Some of the above-mentioned perfumed consumer products may represent an aggressive medium for the compounds according to the invention or for the composition of matter according to the invention and it may therefore be necessary to protect them from premature decomposition, for example by encapsulation or by chemically bonding them to another chemical substance suitable for releasing the ingredient according to the invention upon exposure to a suitable external stimulus such as enzymes, light, heat or a change in pH.

[0157] The proportions in which the compounds according to the invention or the material compositions according to the invention can be incorporated into the various products or compositions mentioned above vary within a wide range of values. These values ​​depend on the nature of the article to be perfumed and on the organoleptic effect desired, as well as on the nature of the co-ingredients in a given base, when the compounds or material compositions according to the invention are mixed with perfuming co-ingredients, solvents or additives customary in the art.

[0158] For example, in the case of perfuming compositions, typical concentrations of 3-(2-isopropyl-4-methylphenyl)propanal or 3-(5-isopropyl-2-methylphenyl)propanal or the composition of matter of the present invention are at levels ranging from 0.001% to 20% by weight, or even more, based on the weight of the perfuming composition into which it is incorporated. In the case of perfumed consumer products, typical concentrations of 3-(2-isopropyl-4-methylphenyl)propanal or 3-(5-isopropyl-2-methylphenyl)propanal or the composition of matter of the present invention are at levels ranging from 0.0001% to 10% by weight, or even more, based on the weight of the consumer product into which it is incorporated.

[0159] Another object of the present invention is a method for arthropod, preferably insect, control, comprising contacting arthropods, preferably insects, with 3-(4-isopropyl-2-methylphenyl)propanal or 3-(2-isopropyl-4-methylphenyl)propanal or 3-(5-isopropyl-2-methylphenyl)propanal or a composition of matter as defined above, directly or with their vapor. In other words, the present invention is a method for imparting, enhancing, improving or modifying the arthropod control properties of an arthropod control composition or an arthropod control article, the method comprising adding to the composition or article an effective amount of at least 3-(2-isopropyl-4-methylphenyl)propanal or at least 3-(5-isopropyl-2-methylphenyl)propanal or at least one composition of matter as defined above.

[0160] Another object of the present invention is the use of 3-(4-isopropyl-2-methylphenyl)propanal or 3-(2-isopropyl-4-methylphenyl)propanal or 3-(5-isopropyl-2-methylphenyl)propanal or a material composition of the invention as defined above for controlling arthropods, preferably insects.

[0161] The term "arthropod" has its normal meaning to those skilled in the art. Arthropods include invertebrates, such as insects, arachnids, and crustaceans, which have a segmented body and jointed appendages. Arthropods generally have a chitinous exoskeleton that molts at intervals, and a dorsal forebrain connected to a ventral chain of ganglia.

[0162] In the understanding of the present invention, arthropods relate to undesirable arthropods, which means that their presence in the air, on the surface of objects, on the surface of plants or on the surface of vertebrates, such as human subjects or other mammals, preferably human subjects, is undesirable. Preferably, the undesirable arthropods are harmful arthropods that affect plants and animals, such as thrips, aphids, beetles, moths, mealybugs, scales, etc., more preferably harmful arthropods that affect animals, such as ants, termites, cockroaches, flies, etc., even more preferably blood-sucking arthropods that affect vertebrates, such as biting flies, bed bugs, kissing bugs, fleas, lice, mosquitoes and ticks, even more preferably mosquitoes and ticks.

[0163] Reasons for undesiring the presence of arthropods may be that the presence of arthropods in the air is unpleasant to the subject, arthropod contact with items can spread diseases and / or germs, or arthropods bite organisms and cause itching, transmission of diseases and / or germs, or feeding by arthropods may be the cause of other diseases and / or conditions.

[0164] The expressions "control", "arthropod control" and the like have normal meanings for a person skilled in the art. In the context of the present invention, "controlling" defines the ability of the arthropod control composition according to the present invention to attract, deter, kill or repel arthropods, preferably to deter or repel arthropods, even more preferably to repel arthropods.

[0165] "Attracting" according to the present invention defines the ability of an arthropod attractant composition according to the present invention to increase or promote the contact or presence of arthropods at a source of the arthropod attractant, for example in the air, on the surface of an object or on a vertebrate such as a human subject or other mammal, preferably on the surface of an object such as a trap, to which the arthropod attractant compound or composition has been applied.

[0166] "Deterring" according to the present invention defines the ability of the arthropod deterrent composition according to the present invention to minimize, reduce, contain or prevent the contact or presence of arthropods at an arthropod deterrent source, such as in the air, on the surface of an article or on the surface of a vertebrate, such as a human subject or other mammal, preferably a human subject, to which the arthropod deterrent compound or composition has been applied. Typically, after an initial tasting of the arthropod deterrent compound or composition, a deterrent effect is exhibited when used as a feeding deterrent, hindering subsequent food intake or oviposition by the pest.

[0167] "Killing" according to the present invention defines the ability of an arthropodicidal composition according to the present invention to kill arthropods at an arthropodicidal source, such as in the air, on the surface of an object or on the surface of a vertebrate such as a human subject or other mammal, preferably a human subject, to which the arthropodicidal compound or composition has been applied. When the arthropodicidal composition is applied to a plant, animal or human subject, it is applied in an amount that kills the arthropod but does not kill the subject.

[0168] "Repellency" according to the present invention defines the ability of an arthropod repellent composition according to the present invention to minimize, reduce, contain or prevent arthropods from approaching or being present at a source of the arthropod repellent, such as in the air, on the surface of an object or on the surface of a vertebrate such as a human subject or other mammal, preferably a human subject, to which the arthropod repellent compound or composition has been applied.

[0169] Auxiliary ingredients for arthropod control formulations may be added to enhance the control effect. Specifically, ingredients selected from the group consisting of: ethyl 3-(acetyl(butyl)amino)propionate (IR3535), N,N-diethyl-3-methylbenzamide (DEET), p-menthane-3,8-diol (PMD), lemon eucalyptus citriodora oil, Citronella spp.) oil, 2-(2-hydroxyethyl)piperidin-1-carboxylic acid sec-butyl ester (picaridin), vanillin, castor oil, cedar oil, cinnamon oil, citronella, citronella oil, clove oil, corn oil, corn mint, corn mint oil, cottonseed oil, 4-allyl-2-methoxyphenol (eugenol), garlic oil, (2E)-3,7-dimethylocta-2,6-dien-1-ol (geraniol), geranium oil, lemongrass oil, linseed oil, peppermint, peppermint oil, 2-phenylethyl propionate, rosemary oil, sesame oil, soybean oil, spearmint, spearmint oil, thyme oil, mint, peppermint oil, pepper extract, wintergreen oil, citronellal, lavender oil, lavender hybrida) extract, Lavandin oil, lemon oil, Margosa extract, Mentha arvensis extract, Metofluthrin, nonanoic acid, pyrethrin and pyrethroid, 2,3,4,5-Bis(butyl-2-ene)tetrahydrofurfural (MGK Repellent11), eucalyptol, cinnamaldehyde, citral, citronellol, coumarin, dibutyl phthalate, diethyl phthalate, dimethyl anthranilate, dimethyl phthalate, ethyl vanillin, eucalyptus oil, δ-octalactone, δ-nonalactone, δ-decanolide, δ-undecalactone, δ-dodecalactone, γ-octalactone, γ-nonalactone, γ-decanolide, γ-undecalactone, γ-dodecalactone, hydroxycitronellal, lime oil, limonene, linalool, methyl anthranilate, myrcene, Neem oil, sabinene, β-caryophyllene, (1H-indol-2-yl)acetic acid, anethole, fennel oil, basil oil, bay leaf oil, camphor, ethyl salicylate, evergreen oil, pine oil, tetramethrin, allethrin, (RS)-α-cyano-3-phenoxybenzyl-(1RS)-cis, cypermethrin, prallethrin, acetamiprid, azadirachtin, bendiocarb, bifenthrin ( bifenthrin, chlorpyrifos, deltamethrin, diazinon, dichlorvos, fipronil, imidacloprid, malathion, neem extract, nicotine, permethrin, rotenone, S-methoprene -methoprene), spinosad (spinosad A), spinosad D, transfluthrin, anise alcohol, octahydrocoumarin, (+-)-2,5-dimethyl-2-indan methanol, 4,4A,5,9B-tetrahydro-indeno[1,2-d]-1,3-dioxane, 2,4-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxane, and mixtures thereof.

[0170] The compounds of the present invention or the composition of matter of the present invention can be prepared according to the methods described below. DETAILED DESCRIPTION

[0171] Example

[0172] The present invention will now be described in further detail by the following examples, wherein abbreviations have their usual meanings in the art and temperatures are expressed in degrees Celsius (°C). 1 H) and 100MHz( 13C) or a Bruker Avance II Ultrashield 400plus operating at 500 MHz ( 1 H) and 125MHz( 13 C) or a Bruker Avance III 500 operating at 600 MHz ( 1 H) and 150MHz( 13 NMR spectra were obtained using a Bruker Avance III 600 cryoprobe operated at 40 °C. Spectra were internally referenced to 0.0 ppm tetramethylsilane. 1 H NMR signal shifts are expressed in δ ppm and coupling constants (J) are expressed in Hz with the following multiplicities: s, singlet; d, doublet; t, triplet; q, quartet; m, multiplet; b, broad peak (indicating unresolved coupling) and were interpreted using Bruker Topspin software. 13 C NMR data are presented as chemical shifts δ ppm and hybridization from DEPT90 and DEPT135 experiments, C, quaternary; CH, methine; CH2, methylene; CH3, methyl.

[0173] Example 1

[0174] Contains 3-(4-isopropyl-2-methylphenyl)propanal and 3-(2-isopropyl-4-methylphenyl)propanal in a ratio of 95:5 Synthesis of the composition of matter of the present invention of propanal

[0175] a) Step 1: Preparation of a mixture comprising 1-(diethoxymethyl)-4-isopropyl-2-methylbenzene and 1-(diethoxymethyl)-2-isopropyl-4-methylbenzene:

[0176] To a mixture of 4-isopropyl-2-methylbenzaldehyde and 2-isopropyl-4-methylbenzaldehyde (ratio 85 / 15; 400 g, 2465.6 mmol, 1 eq.) was added EtOH (168 mL) at 30°C, followed by p-toluenesulfonic acid (0.98 g, 5.18 mmol, 0.0021 eq.). Ethyl orthoformate (383.68 g, 2588.9 mmol, 1.05 eq.) was added over 2 hours. An exotherm was observed (2°C) and the mixture turned brown. 30 minutes after the addition was complete, sodium ethoxide (21% in methanol, 7.4 g, 28.77 mmol, 0.012 eq.) was added and the mixture was concentrated by distillation (Tmax = 145°C, p = 1000-20 mbar) (Tpot = 120-145°C; Tvap = 61-75°C). The light fractions were discarded.

[0177] The product was purified by flash distillation (Tpot = 135°C; Tvap = 118°C) to give 522.3 g of a mixture containing 1-(diethoxymethyl)-4-isopropyl-2-methylbenzene and 1-(diethoxymethyl)-2-isopropyl-4-methylbenzene with a purity of 98%.

[0178] NMR data of the main isomer 1-(diethoxymethyl)-4-isopropyl-2-methylbenzene: 1 H NMR(400MHz,DMSO):7.34-7.36(m,1H),7.02-7.03(m,2H),5.49(s,1H),3.43-3.49( m,4H),2.79-2.85(m,1H),2.29(s,3H),1.18(d,J=5.6Hz,6H),1.12(t,J=5.7Hz,6H). 13 C NMR (125MHz, DMSO): 15.1(q), 18.6(q), 23.8(q), 33.1(d), 60.9(d), 99.7(d), 122.9(d), 126.0(d), 128.3(d), 134.4(s), 135.6(s), 148.0(s).

[0179] b) Step 2: Preparation of a mixture containing 4-isopropyl-2-methyl-1-(1,3,3-triethoxypropyl)benzene and 2-isopropyl-4-methyl-1-(1,3,3-triethoxypropyl)benzene

[0180] A mixture containing 1-(diethoxymethyl)-4-isopropyl-2-methylbenzene and 1-(diethoxymethyl)-2-isopropyl-4-methylbenzene (80.0 g, 338.5 mmol., 0.2 eq.) was added to a 1.0 L Schmizo reactor under nitrogen. The mixture was cooled to 15° C. (set point pot). Boron trifluoride acetic acid (0.32 g, 1.7 mmol., 0.001 eq.) was added. The mixture turned dark red. A mixture of ethyl vinyl ether (124.5 g, 1726.3 mmol., 1.02 eq.) and 1-(diethoxymethyl)-4-isopropyl-2-methylbenzene and 1-(diethoxymethyl)-2-isopropyl-4-methylbenzene (320.0 g, 1353.9 mmol., 0.8 eq.) was added over 5 hours. An exotherm (4° C.) was observed and the color of the mixture became lighter. 15 minutes after the addition was completed, sodium ethoxide (21% ethanol solution, 4.1 g, 15.9 mmol, 0.01 eq.) was added. The mixture was stirred at 15° C. for 1 hour and then concentrated under reduced pressure (Tmax=125° C., p=200-10 mbar, Tvap=33° C.). After the addition of Primol 352, the crude product (514.0 g, 90% GC, brown liquid) was distilled through a 20 cm Widmer column (Tpot=150-160° C.; Tvap=72-117° C.; pressure 0.8 to 0.42 mbar) to give 360.3 g of a mixture containing 4-isopropyl-2-methyl-1-(1,3,3-triethoxypropyl)benzene and 2-isopropyl-4-methyl-1-(1,3,3-triethoxypropyl)benzene with a purity of 98%.

[0181] NMR data of the main isomer 1-(diethoxymethyl)-4-isopropyl-2-methylbenzene: 1 H NMR (500MHz, DMSO):7.12-7.23(m,1H),7.05-7.06(m,1H),6.99-7.00(m,1H),4.56(dt,J=30Hz,4Hz,2H),3.37-3.65(m,4H),3.16-3.27(m,2H) ,2.79-2.83(m,1H),2.26(s,3H),1.68-1.84(m,2H),1.18(d,J=6.9Hz,6 H), 1.14 (t, J = 7.1Hz, 3H), 1.09 (t, J = 6.9Hz, 3H), 1.07 (t, J = 6.9Hz, 3H). 13C NMR(125MHz, DMSO):15.2(q),15.2(q),15.3(q),18.5(q),23.8(q),33.0(d),41.3(t),60.3(t),61 .1(t),63.1(t),74.2(d),99.8(d),123.9(d),125.5(d),128.2(d),134.5(s),137.7(s),146.8(s).

[0182] c) Step 3: Preparation of a mixture containing (E)-3-(4-isopropyl-2-methylphenyl)acrolein and (E)-3-(2-isopropyl-4-methylphenyl)acrolein

[0183] The mixture obtained in step 2 comprising 4-isopropyl-2-methyl-1-(1,3,3-triethoxypropyl)benzene and 2-isopropyl-4-methyl-1-(1,3,3-triethoxypropyl)benzene (300.0 g, 972.57 mmol, 1.0 eq) and acetic acid (321.2 g, 5349.2 mmol, 5.5 eq) were added to a 1.0 L Schmizo reactor under nitrogen. Sodium hydroxide (30% aqueous solution, 129.7 g, 972.57 mmol, 1.0 eq) was added under stirring. Exotherm: 30° C. The mixture was heated to reflux for 6.5 hours (Tpot=103-91° C., Tvap=91-78° C.). The mixture turned yellow, then brown, and became homogeneous. The mixture was cooled to 40° C. and the pressure was reduced to 170 mbar. The mixture was concentrated by distillation (Tmax = 60 ° C, ΔT = 20 ° C, p = 170-1 mbar). The distilled solvent was discarded. Water (675.0 g) and toluene (306 g) containing vitamin E (0.78 g) were slowly added, keeping the temperature above 50 ° C. The mixture was cooled to 25 ° C and allowed to precipitate. The aqueous phase was decanted and discarded. The organic phase was washed with 10% aqueous sodium carbonate solution (153 g) and deionized water (54.0 g). The pressure was reduced to 150 mbar and the mixture was heated to reflux (Tpot = 70 ° C), and water was removed azeotropically until no more water was separated. The orange solution (175.2 g) was purified by flash evaporation (Tpot = 105-110°C; Tvap = 83-94°C; pressure 0.16 mbar) to give 134.4 g of a mixture comprising (E)-3-(4-isopropyl-2-methylphenyl)acrolein and (E)-3-(2-isopropyl-4-methylphenyl)acrolein with a purity of 90%.

[0184] NMR data of the main isomer (E)-3-(4-isopropyl-2-methylphenyl)acrolein: 1H NMR (500MHz, CDCl3): 9.70 (d, J = 7.7Hz, 1H), 7.75 (d, J = 15.8Hz, 1H), 7.54 (d, J = 8Hz, 1H), 7.10-7.13 (m, 2H), 6.64 (dd, J = 15.8 Hz,7.7Hz,1H),2.87-2.92(m,1H),2.47(s,3H),2.26(s,3H),1.68-1.84(m,2H),1.18(d,J=6.9Hz,6H),1.25(d,J=6.9Hz,6H). 13 C NMR (125MHz, CDCl3): 19.9(q), 23.7(q), 34.1(d), 124.8(d), 127.0(d), 128.7(d), 129.3(d), 130.4(s), 138.1(s), 150.4(d), 152.5(s), 194.0(s).

[0185] d) Step 4: Preparation of the composition of matter of the invention comprising 3-(4-isopropyl-2-methylphenyl)propanal and 3-(2-isopropyl-4-methylphenyl)propanal

[0186] The mixture obtained in step 3 comprising (E)-3-(4-isopropyl-2-methylphenyl)propenal and (E)-3-(2-isopropyl-4-methylphenyl)propenal (15.0 g, 79.67 mmol, 1.0 eq.), Pd / C (5%, 50% w / w water, 0.05 g, 0.0003 eq.), AcOK (0.024 g, 0.239 mmol, 0.003 eq.) and iPrOH (30 g) were charged into an autoclave. After purging the autoclave and pressurizing it with 5 bar hydrogen, the mixture was heated at 70° C. for 30 hours. The crude mixture was filtered and concentrated. The crude product was purified by flash evaporation (Tpot = 110°C; pressure 1.0 mbar) to give 11.0 g of the composition of matter of the present invention, which contained 3-(4-isopropyl-2-methylphenyl)propanal and 3-(2-isopropyl-4-methylphenyl)propanal (ratio 95:5, purity 93%).

[0187] NMR data of the main isomer 3-(4-isopropyl-2-methylphenyl)propanal: 1 H NMR(500MHz, CDCl3):9.83(t,J=1.5Hz,1H),7.0-7.1(m,3H),2.89-2.92(m,2 H),2.83-2.85(m,1H),2.71-2.74(m,2H),2.29(s,3H),1.23(d,J=7.0Hz,6H). 13C NMR (125MHz, CDCl3): 19.4(q), 24.0(q), 25.1(t), 33.6(d), 44.1(t), 124.1(d), 128.4(d), 128.6(d), 135.6(s), 135.7(s), 147.1(s), 201.9(d).

[0188] Example 2

[0189] Performance of the compounds of the present invention as arthropod repellents

[0190] a) WarmBody determination method: Small-scale test for screening different concentrations for mosquito repellent efficacy.

[0191] Aedes aegypti is a model organism used for control testing and is one of the model organisms recommended by the World Health Organization (WHO) because it is a very aggressive, blood-feeding mosquito species that generally has low sensitivity to arthropod control compounds. Anopheles gambiae is also a model organism because it feeds on human blood and transmits malaria.

[0192] use The control effect of the composition according to the invention is evaluated in the warm body test (adapted) defined in T, Kessler S, Frei J, Bourquin M, Guerin PM. 2010. J Am Mosq Control Assoc. 26: 381-386. In this in vitro test, the number of mosquitoes landing on warm bodies is measured, simulating an attractive host treated with a test stimulus, to evaluate the repellent effect.

[0193] The published protocol has been adjusted because switching from Anopheles gambiae to Aedes aegypti resulted in a decrease in the number of mosquitoes placed in the test cages due to the size difference (i.e. 30 mosquitoes instead of 50) and an increase in lighting (i.e. 150 lux instead of 4 lux) because Aedes aegypti is a diurnal mosquito.

[0194] In a sandblasted glass Petri dish (28.3 cm 2 ), 100 μL of the composition diluted with ethanol to 5 to 8 different concentrations was added. The number of mosquitoes landing on the warm body was counted for each stimulus, and pure ethanol (solvent) was used as a control.

[0195] The stimuli tested were stimulus A (3-(4-isopropyl-2-methylphenyl) propanal at a concentration of 96%) and stimulus B (a composition of matter containing 3-(4-isopropyl-2-methylphenyl) propanal, 3-(2-isopropyl-4-methylphenyl) propanal and 3-(2-methyl-5-n-prop-2-ylphenyl) propanal at concentrations of 88%, 5% and 2%, respectively) diluted in ethanol. Five to eight concentrations were evaluated for each stimulus, and missing data points are recorded as nd. The average number of mosquito landings when only the solvent (0 mg / mL) was used was equal to 64.5 ± 10.1 landings in two minutes.

[0196] As shown in Table 1, both stimulants showed a corresponding reduction in the number of mosquito landings due to the concentration. This indeed proves the biorepellent effect of the stimulants on mosquito behavior, as only 0.04% of any stimulant applied to the warm body reduced the number of landings by >50% (Table 1).

[0197] Table 1: Percent repellency of Aedes aegypti landing on warm bodies with different stimulants at different concentrations as attractants.

[0198]

[0199] b) Warm plate method: Small-scale test for screening different concentrations for repellent efficacy against ticks.

[0200] The repellent efficacy of different compounds against Ixodes ricinus L, a tick that transmits bacterial and viral pathogens, was evaluated. Ixodes ricinus L is a tick listed in the Guidance on the European Biological Products Regulation [Vol II, Efficacy-Assessment&Evaluation(Parts B+C), v6.0, 2023]. The repellent efficacy was observed on the final stage nymphs.

[0201] use The repellent efficacy was evaluated using the protocol of the in vitro warm plate assay defined in T, Bourquin M, Guerin PM, 2013. Pestic. Biochem. Phys. 107(2): 160-168.

[0202] Ticks were given the choice to cross the area coated with 3-(4-isopropyl-2-methylphenyl)propanal (96%) or remain in the refuge area not coated with any compound. To stimulate tick movement, the warm plate was heated to 33°C (to simulate vertebrate skin temperature) and maintained in a favorable environment (23°C, 85% RH).

[0203] The irritant tested was irritant A (3-(4-isopropyl-2-methylphenyl)propanal at a concentration of 96%) diluted in ethanol. Twelve different ticks were tested for each of the four concentrations.

[0204] As shown in Table 2, 3-(4-isopropyl-2-methylphenyl)propanal repelled ticks in a dose-response manner. All ticks were repelled as long as 0.02% 3-(4-isopropyl-2-methylphenyl)propanal (96%) was applied on the warm plate (Table 2).

[0205] Table 2: Percent repellency of the tick Ixodes ricinus on warm plates with three different concentrations (n=12) of 3-(4-isopropyl-2-methylphenyl)propanal as attractant.

[0206]

Claims

1. A method of imparting, enhancing, improving or modifying the odor characteristics of a perfuming composition or a perfumed article, the method comprising adding to said composition or article an effective amount of a composition of matter comprising 3-(4-isopropyl-2-methylphenyl)propanal and 3-(2-isopropyl-4-methylphenyl)propanal.

2. The method of claim 1, wherein the composition of matter comprises at least 75% w / w 3-(4-isopropyl-2-methylphenyl)propanal, the percentage being calculated relative to the total weight of the composition of matter.

3. The method according to any one of claims 1 to 2, wherein the composition of matter comprises 75% to 99.5% w / w 3-(4-isopropyl-2-methylphenyl)propanal and 0.5% to 25% w / w 3-(2-isopropyl-4-methylphenyl)propanal, the percentages being calculated relative to the total weight of the composition of matter.

4. The method according to any one of claims 1 to 3, wherein the material composition comprises 80% to 99% w / w 3-(4-isopropyl-2-methylphenyl)propanal and 1% to 20% w / w 3-(2-isopropyl-4-methylphenyl)propanal, preferably 85% to 95% w / w 3-(4-isopropyl-2-methylphenyl)propanal and 3% to 15% w / w 3-(2-isopropyl-4-methylphenyl)propanal, the percentages being calculated relative to the total weight of the material composition.

5. The method according to any one of claims 1 to 4, wherein the composition of matter further comprises up to 5% w / w of 3-(5-isopropyl-2-methylphenyl)propanal, the percentage being calculated relative to the total weight of the composition of matter.

6. Use of a composition of matter as defined in claims 1 to 5 as perfuming ingredient.

7. A composition of matter comprising 3-(4-isopropyl-2-methylphenyl)propanal and 3-(2-isopropyl-4-methylphenyl)propanal as defined in claims 1 to 5.

8. 3-(2-isopropyl-4-methylphenyl)propanal as compound.

9. Use of 3-(2-isopropyl-4-methylphenyl)propanal or 3-(5-isopropyl-2-methylphenyl)propanal as a perfuming ingredient.

10. A method of imparting, enhancing, improving or modifying the odor characteristics of a perfuming composition or a perfumed article, the method comprising adding to said composition or article an effective amount of 3-(2-isopropyl-4-methylphenyl)propanal or 3-(5-isopropyl-2-methylphenyl)propanal.

11. A perfuming composition comprising: i) 3-(2-isopropyl-4-methylphenyl)propanal or 3-(5-isopropyl-2-methylphenyl)propanal or at least one composition of matter as defined in claim 7; ii) at least one ingredient selected from the group consisting of a fragrance carrier and a fragrance base; and iii) optionally, at least one flavor adjuvant.

12. A perfumed consumer product comprising 3-(2-isopropyl-4-methylphenyl)propanal or 3-(5-isopropyl-2-methylphenyl)propanal or at least one composition of matter as defined in claim 7 or a perfumed composition as defined in claim 11.

13. The perfumed consumer product according to claim 12, wherein the perfumed consumer product 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.

14. A perfumed consumer product according to claim 13, wherein the perfumed consumer product is a high quality perfume, a perfume rub or an eau de toilette, a cologne, a shaving lotion or aftershave, a liquid or solid detergent, optionally in capsule or tablet form, a fabric softener, a liquid or solid fragrance enhancer, a dryer sheet, a fabric refresher, an ironing water, paper, a bleach, a carpet cleaner, a curtain care product, a shampoo, a leave-on or rinse-off hair conditioner, a dyeing preparation, a color care product, a hair styling product, a toothpaste, a toothpaste, a toothpaste, a toothpaste, a toothpaste, a toothpaste, a toothpaste, a toothpaste, a toothpaste, a toothpaste, a toothpaste, a toothpaste, a toothpaste, a toothpaste, a toothpaste, a toothpaste, a toothpaste, a toothpaste, a toothpaste, a toothpaste Tooth care products, disinfectants, intimate care products, hair sprays, skin creams or lotions, vanishing creams, deodorants or antiperspirants, hair removers, self-tanning products, sunscreen or after-sun products, nail products, skin cleansers, makeup, soaps, shower or bath mousses, bath oils or shower gels, foot / hand care products, hygiene products, air fresheners, "ready-to-use" powder air fresheners, mildew removers, furniture care products, wipes, dishwashing detergents or hard surface detergents, leather care products, car care products.

15. Use of 3-(4-isopropyl-2-methylphenyl)propanal or 3-(2-isopropyl-4-methylphenyl)propanal or 3-(5-isopropyl-2-methylphenyl)propanal or at least one substance composition as defined in claim 7 for controlling arthropods, preferably insects.

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