WO2021069331A1 - Substance odorante au parfum de muguet - Google Patents

Substance odorante au parfum de muguet Download PDF

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Publication number
WO2021069331A1
WO2021069331A1 PCT/EP2020/077714 EP2020077714W WO2021069331A1 WO 2021069331 A1 WO2021069331 A1 WO 2021069331A1 EP 2020077714 W EP2020077714 W EP 2020077714W WO 2021069331 A1 WO2021069331 A1 WO 2021069331A1
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Prior art keywords
compound
mixture
formula
methoxypropan
product
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English (en)
Inventor
Fabrice Robvieux
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Firmenich SA
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Firmenich SA
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume preparations
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/277—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes
    • C11D3/502—Protected perfumes
    • C11D3/507—Compounds releasing perfumes by thermal or chemical activation

Definitions

  • the present invention relates to the field of perfumery. More particularly, it concerns a compound of formula (I) or a properfume suitable to release a compound of formula (I), as defined below, and its uses as perfuming ingredient, in particular to confer odor notes of muguet type. Moreover, following what is mentioned herein, the present invention comprises the compound of formula (I) as part of a perfuming composition or of a perfumed consumer product.
  • the present invention provides a novel perfumery ingredient imparting lily of the valley note, by using compounds of formula (I) which imparts a less aggressive odor than the prior art and with an increase biodegradability.
  • the prior art document mentioned above does not disclose the compounds of formula (I) or the organoleptic properties of the compounds of formula (I). Summary of the Invention
  • the invention relates to compound of formula (I) imparting an odor of floral type, in particular lily of the valley (also named muguet) which is much appreciated in perfumery.
  • a first object of the present invention a method to confer, enhance, 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 in the form of any one of its stereoisomers or a mixture thereof, and wherein
  • R 1 and R 2 represent, independently from each other, a hydrogen atom or a C 1-2 alkyl group
  • -C(Me)2(OMe) group is, relative to position 1, a meta or a para substituent of the aromatic ring or a mixture thereof.
  • a second object of the present invention is the use as perfuming ingredient of a compound of formula (I) as defined above.
  • a third object of the present invention is a compound of formula in the form of any one of its stereoisomers or a mixture thereof, and wherein
  • R 1 and R 2 represent, independently from each other, a hydrogen atom or a C 1-2 alkyl group
  • -C(Me)2(OMe) group is, relative to position 1, a meta or a para substituent of the aromatic ring or a mixture thereof; provided that 3-[4-(2-methoxy-2-propanyl)phenyl]propanal and 3-[4-(2-methoxypropan- 2-yl)phenyl]butanal are excluded.
  • Another object of the present invention is a properfume compound suitable to release the compound of formula in the form of any one of its stereoisomers or a mixture thereof, and wherein
  • R 1 and R 2 represent, independently from each other, a hydrogen atom or a C1-2 alkyl group
  • -C(Me)2(OMe) group is, relative to position 1, a meta or a para substituent of the aromatic ring or a mixture thereof.
  • Another object of the present invention is a perfuming composition
  • a perfuming composition comprising i) at least one compound of formula (I) and / or at least one properfume compound, 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.
  • a further object of the present invention is a perfumed consumer product comprising at least one compound of formula (I), and / or at least one properfume compound or a perfuming composition as defined above.
  • Figure 1 Biodegradation of 3-[4-(2-methoxy-2-propanyl)phenyl]propanal (invention’s compound) and 3-[4-(2-methoxy-2-propanyl)phenyl]-2-methylpropanal (prior art compound) in function of time.
  • a first object of the present invention is a compound of formula in the form of any one of its stereoisomers or a mixture thereof, and wherein
  • R 1 and R 2 represent, independently from each other, a hydrogen atom or a C1-2 alkyl group
  • -C(Me)2(OMe) group is, relative to position 1, a meta or a para substituent of the aromatic ring or a mixture thereof.
  • Said compound can be used as perfuming ingredient, for instance to impart odor notes of the floral type.
  • said compound (I) is C 13 -C 17 compound, preferably a C 13 -C 14 compound.
  • any one of its stereoisomers or the similar, it is meant the normal meaning understood by a person skilled in the art, i.e. that the invention compound can be a pure enantiomer (if chiral) or a mixture of enantiomers.
  • -C(Me)2(OMe) group is, relative to position 1, a meta or a para substituent of the aromatic ring or a mixture thereof’, it is meant that the compound of formula (I) may be in the form of a pure regioisomer; e.g. - C(Me)2(OMe) group being a para substituent of the aromatic ring, relative to position 1 or the compound of formula (I) may be in the form of a mixture of regioisomers; e.g.
  • -C(Me)2(OMe) group is, relative to position 1, a meta substituent of the aromatic ring or a mixture thereof’, it designates that the -C(Me)2(OMe) group is in meta position relative to position 1 and in para relative to the carbon bearing R 2 group.
  • the -C(Me)2(OMe) group may be in position 4 or 5 respectively corresponding to para and meta position.
  • the compound of formula (I) is in the form of a mixture of regioisomers comprising at least 80 % of regioisomers wherein -C(Me)2(OMe) group is a para substituent of the aromatic ring and at most 20 % regioisomers wherein -C(Me)2(OMe) group is a meta substituent of the aromatic ring.
  • the compound of formula (I) is in the form of a mixture of regioisomers comprising at least 90 % of regioisomers wherein -C(Me)2(OMe) group is a para substituent of the aromatic ring and at most 10 % regioisomers wherein C(Me)2(OMe) group is a meta substituent of the aromatic ring.
  • R 2 represents a methyl group
  • the invention s compound is of formula in the form of any one of its stereoisomers or a mixture thereof, and wherein R 1 and R 2 represent, independently from each other, a hydrogen atom or a C1-2 alkyl group.
  • R 1 may represent a hydrogen atom or a methyl group, preferably a hydrogen atom.
  • the invention s compound is of formula in the form of any one of its stereoisomers or a mixture thereof, and wherein R 2 represents a hydrogen atom or a C 1-2 alkyl group.
  • R 2 may represent a hydrogen atom or a methyl group, preferably a hydrogen atom.
  • R 2 may represent a hydrogen atom or a methyl group, preferably a hydrogen atom.
  • the invention may cite, as non-limiting example, 3-[4-(2-methoxy-2-propanyl)phenyl]propanal imparting a fresh floral, lily of the valley odor note with creamy aspect and subtle green facet.
  • the organoleptic properties of this compound strongly reminiscent of the well-known Lilial ® (2-methyl-3-[4-(2-methyl- 2-propanyl)phenyl]propanal, trademark from Givaudan-Roure SA, Vernier, Congress) make it an olfactive substitute of the allergen Lilial ® while distinguishing by less technic impression.
  • the invention imparts the nicest lily of the valley note.
  • the compound of formula (I) is 3-[4-(2-methoxy-2-propanyl)phenyl]propanal, 3-[4-(2-methoxypropan-2- yl)-2-methylphenyl]propanal or a mixture comprising 3-(4-(2-methoxypropan-2-yl)-2- methylphenyl)propanal and 3-(5-(2-methoxypropan-2-yl)-2-methylphenyl)propanal.
  • the compound of formula (I) is 3-[4-(2-methoxy-2-propanyl)phenyl]propanal, 3-[4-(2-methoxypropan-2-yl)-2-methylphenyl]propanal or a mixture comprising at least 90% of 3-(4-(2-methoxypropan-2-yl)-2-methylphenyl)propanal and at most 10% of 3-(5- (2-methoxypropan-2-yl)-2-methylphenyl)propanal.
  • the compound of formula (I) is 3-[4-(2-methoxy-2-propanyl)phenyl]propanal.
  • the invention’s compounds distinguish themselves by a clearly stronger muguet, creamy and fresh note and by lacking the aldehydic note so characteristic of the prior art compound.
  • the invention’s compounds impart an odor note closer to Lilial ® than the prior art compounds while being more elegant, softer and less technic than Lilial ® .
  • the invention’s compounds are more substantive and more enveloping than the prior art compounds.
  • the invention’s compounds blend particularly well with the musky note and boost their perception even after 24 h which is not observed with 3-(4-(2-methoxypropan-2- yl)phenyl)-2-methylpropanal or even with Lilial ® .
  • the odor of the invention’s compounds is also lacking, or not possessing significant, fatty and metallic notes which are characteristic of the prior art compounds. Said differences lend the invention’s compounds and the prior art compounds to be each suitable for different uses, i.e. to impart different organoleptic impressions.
  • the invention concerns the use of a compound of formula (I) as a perfuming ingredient.
  • a method or a process to confer, enhance, improve or modify the odor properties of a perfuming composition or of a perfumed article or of a surface which method comprises adding to said composition or article an effective amount of at least a compound of formula (I), e.g. to impart its typical note.
  • the final hedonic effect may depend on the precise dosage and on the organoleptic properties of the invention’s compound, but anyway the addition of the invention’s compound will impart to the final product its typical touch in the form of a note, touch or aspect depending on the dosage.
  • use of a compound of formula (I) it has to be understood here also the use of any composition containing a compound (I) and which can be advantageously employed in the perfumery industry.
  • compositions which in fact can be advantageously employed as perfuming ingredients, are also an object of the present invention.
  • another object of the present invention is a perfuming composition
  • a perfuming composition comprising: i) as a perfuming ingredient, at least one invention’s compound and / or at least one properfume compound, as defined below; 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.
  • 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.
  • 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.
  • an emulsifying system i.e. a solvent and a surfactant system
  • a solvent commonly used in perfumery i.e. a solvent and a surfactant system
  • solvents such as butylene or propylene glycol, glycerol, dipropyleneglycol and its monoether, 1,2,3- propanetriyl triacetate, dimethyl glutarate, dimethyl adipate l,3-diacetyloxypropan-2-yl acetate, diethyl phthalate, isopropyl myristate, benzyl benzoate, benzyl alcohol, 2-(2- ethoxyethoxy)-l-ethano, tri-ethyl citrate or mixtures thereof, which are the most commonly used.
  • solvents such as butylene or propylene glycol, glycerol, dipropyleneglycol and its monoether, 1,2,3- propanetriyl triacetate, dimethyl glutarate, dimethyl adipate l,3-diacetyloxypropan-2-yl acetate, diethyl phthalate, isopropyl myristate, benzyl benzoate,
  • compositions which comprise both a perfumery carrier and a perfumery base 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).
  • 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)
  • Dowanol ® origin: Dow Chemical Company
  • hydrogenated castors oils such as those known under the trademark Cremophor ® RH 40 (origin: BASF).
  • 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, wood based materials, organic or inorganic gels, clays, gypsum talc or zeolites.
  • encapsulating materials may comprise wall-forming and plasticizing materials, such as mono, di- or trisaccharides, natural or modified starches, hydrocolloids, cellulose derivatives, polyvinyl acetates, polyvinylalcohols, proteins or pectins, or yet the materials cited in reference texts such as H. Scherz, Hydrokolloide: Stabilisatoren, Dickungs- und Gelierstoff in Strukturn, Band 2 der Strukturtechnisch Strukturchemie, claritat, Behr's Verlag GmbH & Co., Hamburg, 1996.
  • 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.
  • solid carriers As non-limiting examples of solid carriers, one may cite in particular the core shell capsules with resins of aminoplast, 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. Resins may be produced by the polycondensation of an aldehyde (e.g.
  • 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.
  • a polyocyanate like a trimer of hexamethylene diisocyanate, a trimer of isophorone diisocyanate or xylylene diisocyanate or a Biuret of hexamethylene diisocyanate
  • perfumery base what is meant here is a composition comprising at least one perfuming co-ingredient.
  • perfuming co-ingredient is not of formula (I).
  • perfuming co ingredient it is meant here a compound, which is used in a perfuming preparation or a composition to impart a hedonic effect.
  • 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.
  • 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.
  • these perfuming co-ingredients belong to chemical classes as varied as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogenous or sulphurous heterocyclic compounds and essential oils, and said perfuming co-ingredients can be of natural or synthetic origin.
  • perfuming co-ingredients knows for having a similar olf active note, such as:
  • perfuming co-ingredients which are commonly used in perfume formulations, such as:
  • Aldehydic ingredients decanal, dodecanal, 2-methyl-undecanal, 10-undecenal, octanal, nonanal and/or nonenal;
  • Aromatic -herbal ingredients eucalyptus oil, camphor, eucalyptol, 5- methyltricyclo[6.2.1.0 ⁇ 2,7 ⁇ ]undecan-4-one, l-methoxy-3-hexanethiol, 2-ethyl- 4, 4-dimethyl- 1,3-oxathiane, 2,2,7/8,9/10-Tetramethylspiro[5.5]undec-8-en-l-one, menthol and/or alpha-pinene;
  • Citrus ingredients dihydromyrcenol, citral, orange oil, linalyl acetate, citronellyl nitrile, orange terpenes, limonene, l-p-menthen-8-yl acetate and/or l,4(8)-p- menthadiene;
  • 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- l-yl)-3-buten-2-one, (lE)-l-(2,6,6-trimethyl-2-cyclohexen-l-yl)-l-penten-3-one, l-(2, 6, 6-trimethyl- l,3-cyclohexadien-l-yl)-2-buten-l-one, (2E)-l-(2,6,6- trimethyl-2
  • Fruity ingredients gamma-undecalactone, 2, 2, 5 -trimethyl- 5- pentylcyclopentanone, 2-methyl-4-propyl-l,3-oxathiane, 4-decanolide, ethyl 2- methyl-pentanoate, hexyl acetate, ethyl 2-methylbutanoate, gamma-nonalactone, allyl heptanoate, 2-phenoxyethyl isobutyrate, ethyl 2-methyl- l,3-dioxolane-2- acetate, 3-(3,3/l,l-dimethyl-5-indanyl)propanal, diethyl 1,4- cyclohexanedicarboxylate, 3-methyl-2-hexen-l-yl acetate, l-[3,3- dimethy Icy clohexyl] ethyl [3 -ethyl-2-oxiranyl] acetate and
  • Woody ingredients l-[(lRS,6SR)-2,2,6-trimethylcyclohexyl]-3-hexanol, 3,3- dimethyl-5-[(lR)-2,2,3-trimethyl-3-cyclopenten-l-yl]-4-penten-2-ol, 3,4'- dimethylspiro[oxirane-2,9'-tricyclo[6.2.1.0 2,7 ]undec[4]ene, (1- ethoxyethoxy)cyclododecane, 2,2,9,ll-tetramethylspiro[5.5]undec-8-en-l-yl acetate, l-(octahydro-2,3,8,8-tetramethyl-2-naphtalenyl)-l-ethanone, patchouli oil, terpenes fractions of patchouli oil, clearwood ® , (l'R,E)-2-ethyl-4-(2',2',3'- trimethyl-3'-
  • ingredients e.g. amber, powdery spicy or watery: dodecahydro-3a,6,6,9a- tetramethyl-naphtho[2,l-b]furan and any of its stereoisomers, heliotropin, anisic aldehyde, eugenol, cinnamic aldehyde, clove oil, 3-(l,3-benzodioxol-5-yl)-2- methylpropanal, 7-methyl-2H- 1 ,5-benzodioxepin-3(4H)-one, 2,5,5-trimethyl- l,2,3,4,4a,5,6,7-octahydro-2-naphthalenol, 1-phenylvinyl acetate, 6-methyl-7-oxa- l-thia-4-azaspiro[4.4]nonan and/or 3-(3-isopropyl-l-phenyl)butanal.
  • a perfumery base according to the invention may not be limited to the above mentioned perfuming co-ingredients, and many other of these co-ingredients 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-l-cyclohexen-l-yl)-2-butanone, trans-3-(dodecylthio)-l-(2,6,6-trimethyl- 3-cyclohexen-l-yl)-l-butanone, 2-phenylethyl oxo(phenyl)acetate or a mixture thereof.
  • perfumery adjuvant we mean here an ingredient capable of imparting additional added benefit such as a color, a particular light resistance, chemical stability, etc.
  • 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
  • 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.
  • composition consisting of at least one compound of formula (I) and / or at least one properfume releasing the compound of formula (I) and at least one perfumery carrier consists of a particular embodiment of the invention as well as a perfuming composition comprising at least one compound of formula (I) and / or at least one properfume releasing the compound of formula (I), at least one perfumery carrier, at least one perfumery base, and optionally at least one perfumery adjuvant.
  • 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.
  • 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.
  • unpurified reaction mixtures are generally excluded from the present invention unless otherwise specified.
  • the invention’s compound can also be advantageously used in all the fields of modern 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.
  • Another object of the present invention consists of by a perfumed consumer product comprising, as a perfuming ingredient, at least one compound of formula (I) and / or at least one properfume compound as defined below or a perfuming composition as defined above.
  • the invention’s compound can be added as such or as part of an invention’s perfuming composition.
  • 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).
  • 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.
  • said perfumed consumer product is a non-edible product.
  • Non-limiting examples of suitable perfumed consumer products include a perfume, such as a fine perfume, a splash or eau de perfume, a cologne or a shave or after- shave lotion; a fabric care product, such as a liquid or solid detergent, a fabric softener, a liquid or solid scent booster, 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 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.
  • 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 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 leather care product; a car care product, such as a polish, a wax or a plastic cleaner.
  • 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 home care product, such as a mold remover, a furnisher care product, a wipe, a
  • 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.
  • typical concentrations are in the order of 0.001 % to 10 % by weight, or even more, of the compounds of the invention based on the weight of the composition into which they are incorporated.
  • typical concentrations are in the order of 0.0001 % to 5 % by weight, or even more, of the compounds of the invention based on the weight of the consumer product into which they are incorporated.
  • 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.
  • a suitable external stimulus such as an enzyme, light, heat or a change of pH.
  • a precursor compound able to release a perfuming ingredient under a suitable trigger is also known as properfume or profragrance.
  • So another object of the present invention is a properfume compound suitable to release the compound of formula in the form of any one of its stereoisomers or a mixture thereof, and wherein
  • R 1 and R 2 represent, independently from each other, a hydrogen atom or a C 1-2 alkyl group
  • -C(Me)2(OMe) group is, relative to position 1, a meta or a para substituent of the aromatic ring or a mixture thereof.
  • the properfume compound suitable to release the compound of formula in the form of any one of its stereoisomers or a mixture thereof, and wherein R 1 and R 2 as the same meaning as above.
  • the invention’s compounds can be prepared according to standard method known in the art as described herein-below. Examples
  • Electrodes carbon / stainless steel Electrode Surface: 100 cm 2 Electrodes spacing: 5mm Power: 4A (40mA/cm 2 )
  • This oil was purified by vacuum distillation (106 to 162°C, 0.7 to 0.2 mbar) through a Sulzer path to give 13.8 g (9%) of l-(dimethoxymethyl)-4-(2-methoxypropan- 2-yl)-2-methylbenzene.
  • this oil was purified by vacuum distillation (140 to 180°C, 0.1 mbar) through a short path to give 0.85 g (383%) of 3-(4-(2-methoxypropan-2-yl)-2-methylphenyl)propanal.
  • Electrochemistry was run using the following data: Electrodes: carbon / stainless steel Electrode Surface: 100 cm 2 Electrodes spacing: 5mm Power: 4A (40mA/cm 2 ) Voltage: ⁇ 35V
  • This oil was purified by vacuum distillation (100 to 140°C, 1 to 0.5 mbar) through a Fischer column path and a short path to give 49 g (45% yield) of l-(dimethoxymethyl)-4- (2-methoxypropan-2-yl)-2-methylbenzene with a purity of 94% (the rest being 2- (dimethoxymethyl)-4-(2-methoxypropan-2-yl)-l-methylbenzene).
  • step c) To l-(dimethoxymethyl)-4-(2-methoxypropan-2-yl)-2-methylbenzene as obtained in step c) (49 g, 205.6 mmol) in a round bottom flask was added BF 3 .Et 2 0 (0.06 g, 0.4 mmol). Then Ethyl vinyl ether (15.6 g, 215.9 mmol) was added in 30 minutes in order to maintain an internal temperature below 10°C. The mixture was slowly warmed-up to RT overnight.
  • MeONa (30 % in MeOH, 0.3 g) was added to quench the catalyst.
  • Acetic acid 69.2 g, 1152 mmol
  • Sodium hydroxide 28 g, 209.4 mmol
  • the mixture was heated under vacuum (105°C, 800 to 700 mbar) with removal of light compounds (63 g collected). When nothing distilled off, reaction was cooled down to RT. Two extractions with 100 g of Heptane were done. The combined organic phase was washed with 100 g of water.
  • a perfuming composition for fine fragrance was prepared by admixing the following ingredients:
  • the composition acquired a more aldehydic and greener connotation with less creamy aspect.
  • the fragrance composition was more aggressive with less volume. After 24 h, not much effect was perceived apart from a slight green and fatty aspect.
  • composition comprising the invention’s compound was the nicest and with the strongest organoleptic properties even after 24 h.
  • Biodegradability measurement of the invention s compound and comparative compound
  • the biodegradation assessment was carried out using the OECD 301F (‘manometric respirometry’) biodegradation test under identical conditions with sludge inoculum originating from the same wastewater treatment plant as follows.
  • Mineral medium was prepared from stock solutions according to the OECD guideline (OECD, 1992): 100 mL of solution A (8.50 g/L KH 2 P0 4 , 21.75 g/L K 2 HP0 4 , 33.40 g/L Na 2 HP0 4 x 2 H 2 0, 0.50 g/L NH 4 C1), 10 mL of solution B (27.50 g/L CaCl 2 ), 10 mL of solution C (22.50 g/L MgSC x 7 fhO) and 10 mL of solution D (0.25 g/L FeCL x 6 H2O) were mixed, the volume adjusted to 10 L with demineralized water and the pH adjusted to 7.4.
  • solution A 8.50 g/L KH 2 P0 4 , 21.75 g/L K 2 HP0 4 , 33.40 g/L Na 2 HP0 4 x 2 H 2 0, 0.50 g/L NH 4 C1
  • 10 mL of solution B 27.
  • Activated sludge was collected from the sewage plant at Villette (Thonex, Switzerland), which treats predominantly domestic wastewaters.
  • the sample was filtered on a polypropylene 149 mhi pore size filter (Spectrum Laboratories, Collinso Dominguez, USA), washed three times by centrifugation at 3000 x g for 30 min at room temperature and suspended in the same volume of medium. The suspension was stirred and maintained under pure oxygen at room temperature overnight.
  • the test material was dispersed directly in the final volume of medium (200 mL) to give a test concentration of 100 mg/L and then inoculated in the test flask with 30 mg/L dry weight of sludge. Use was made of duplicates containing inoculum only and duplicates containing test substance plus inoculum.
  • Table 1 Percentage of the biodegradation of invention’s compounds and comparative compound
  • the invention’s compound, 3-(4-(2-methoxypropan-2-yl)phenyl)propanal are highly biodegradable after 60 days with a percentage of degradation reaching more than 80% whereas 3-[4-(2-methoxy-2-propanyl)phenyl]-2-methylpropanal does not exceed 60%.

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Abstract

La présente invention concerne un composé de formule (I) sous la forme de l'un quelconque de ses stéréo-isomères ou d'un mélange correspondant et dans laquelle R1 et R2 représentent, indépendamment l'un de l'autre, un atome d'hydrogène ou un groupe C1-2-alkyle ; et le groupe -C(Me)2(OMe) est, par rapport à la position 1, un substituant en position méta ou para du cycle aromatique ou un mélange correspondant. L'invention concerne également l'utilisation du composé de l'invention en tant qu'ingrédient parfumant, le composé de l'invention comme partie d'une composition parfumante ou d'un produit de consommation parfumé et un proparfum libérant le composé de l'invention.
PCT/EP2020/077714 2019-10-10 2020-10-02 Substance odorante au parfum de muguet Ceased WO2021069331A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023078870A3 (fr) * 2021-11-03 2023-09-28 Firmenich Sa Compositions de parfum offrant des bienfaits hydratants

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011029743A1 (fr) * 2009-09-09 2011-03-17 Basf Se Compositions de parfum sentant le muguet contenant du 2,5,7,7-tétraméthyloctanal
WO2016074865A1 (fr) * 2014-11-10 2016-05-19 Givaudan Sa Composés à base de phényle substitués par des fractions aldéhyde et leur utilisation en parfumerie
WO2017009175A1 (fr) * 2015-07-14 2017-01-19 Firmenich Sa Composé au parfum de muguet
US10138195B2 (en) * 2014-11-10 2018-11-27 Givaudan, S.A. Organic compounds

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011029743A1 (fr) * 2009-09-09 2011-03-17 Basf Se Compositions de parfum sentant le muguet contenant du 2,5,7,7-tétraméthyloctanal
WO2016074865A1 (fr) * 2014-11-10 2016-05-19 Givaudan Sa Composés à base de phényle substitués par des fractions aldéhyde et leur utilisation en parfumerie
US10138195B2 (en) * 2014-11-10 2018-11-27 Givaudan, S.A. Organic compounds
WO2017009175A1 (fr) * 2015-07-14 2017-01-19 Firmenich Sa Composé au parfum de muguet

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023078870A3 (fr) * 2021-11-03 2023-09-28 Firmenich Sa Compositions de parfum offrant des bienfaits hydratants

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