WO2019230974A1 - Substance de parfum - Google Patents

Substance de parfum Download PDF

Info

Publication number
WO2019230974A1
WO2019230974A1 PCT/JP2019/021862 JP2019021862W WO2019230974A1 WO 2019230974 A1 WO2019230974 A1 WO 2019230974A1 JP 2019021862 W JP2019021862 W JP 2019021862W WO 2019230974 A1 WO2019230974 A1 WO 2019230974A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
fragrance
consumer product
acetaldehyde
formula
Prior art date
Application number
PCT/JP2019/021862
Other languages
English (en)
Inventor
Kazuma Hojo
Original Assignee
Takasago International Corporation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Takasago International Corporation filed Critical Takasago International Corporation
Publication of WO2019230974A1 publication Critical patent/WO2019230974A1/fr

Links

Classifications

    • 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
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Definitions

  • the presently disclosed subject matter relates to compounds having uses in the fragrances as well as compositions containing such compounds.
  • fragrance industry is constantly reliant on the development of new chemicals with favorable organoleptic properties.
  • new fragrance compounds can be used to create new fragrance compositions having unique odor characteristics or can modify or enhance the organoleptic properties of existing fragrance compositions.
  • Fragrance compositions are used in a wide variety of consumer products, including fine fragrances, personal care products, home care products, air care products, and the like.
  • fragrance compounds having natural green, floral, fruity odor notes with a fresh aquatic note. These compounds can be used alone or incorporated into a fragrance composition and/or consumer product.
  • the present disclosure provides a fragrance composition comprising a fragrance compound of formula (I), or an isomer thereof.
  • R 1 and R 2 are independently selected from hydrogen atom and methyl group.
  • the fragrance compound is selected from the group consisting of 2-(cyclohex-3-en-1-ylmethoxy)acetaldehyde; 2-((2,4-dimethylcyclohex-3-en-1-yl)methoxy)acetaldehyde; isomers thereof; and combinations thereof.
  • the fragrance composition can further include an additional fragrance compound selected from a citrus compound, a floral compound, a fruity compound, a investigating compound, a green compound, a musk compound, a spicy compound, a woody compound, an aldehydic compound, a balsamic compound, a marine compound, a mossy compound, an amber compound, an animalic compound, a herbaceous compound, a piney compound, a powdery compound, and combinations thereof.
  • the fragrance composition can further include a solvent.
  • the present disclosure also provides methods of modifying the odor properties of a fragrance composition, including adding to the fragrance composition an olfactory effective quantity of a fragrance compound of formula (I).
  • the fragrance compound can be 2-(cyclohex-3-en-1-ylmethoxy)acetaldehyde or 2-((2,4-dimethylcyclohex-3-en-1-yl)methoxy)acetaldehyde.
  • the present disclosure provides a consumer product comprising a consumer product base and a fragrance compound of formula (I) or an isomer thereof.
  • the fragrance compound can be selected from the group consisting of 2-(cyclohex-3-en-1-ylmethoxy)acetaldehyde; 2-((2,4-dimethylcyclohex-3-en-1-yl)methoxy)acetaldehyde; isomers thereof; and combinations thereof.
  • the fragrance compound can be 2-(cyclohex-3-en-1-ylmethoxy)acetaldehyde or 2-((2,4-dimethylcyclohex-3-en-1-yl)methoxy)acetaldehyde.
  • the consumer product is selected from a fine fragrance, a personal care product, a home care product, and an air care product.
  • the fine fragrance can be selected from perfume, tinct de perfume, eau de perfume, millesime, perfume de toilette, eau de toilette, eau de cologne, body splash, after shave, body mists, and baby colognes.
  • the personal care product can be selected from lotions, creams, moisturizers, body washes, hand soaps, shampoos, conditioners, and soaps.
  • the home care product can be selected from fabric conditioner, fabric softener, laundry detergent, laundry additive, rinse additive, bleach, dryer sheets, perfume beads, car care products, dishwashing detergent, and hard surface cleaners.
  • the air care product can be selected from a candle, aerosol, air freshener, liquid electric air freshener, fragrance diffuser, gel air freshener, plug-in air freshener, plug-in oil, and wax melt.
  • the present disclosure also provides methods of modifying the odor properties of a consumer product, including adding to a consumer product base an olfactory effective quantity of a fragrance compound of formula (I), or an isomer thereof.
  • the present disclosure provides methods of manufacturing a consumer product comprising admixing a fragrance compound of formula (I), or an isomer thereof, with a consumer product base.
  • the fragrance compound is incorporated into a fragrance composition prior to admixing with the consumer product base.
  • the present disclosure provides novel compounds of the above formula (I), or an isomer thereof, wherein R 1 and R 2 are independently selected from hydrogen atom and methyl group.
  • the novel compounds are selected from the group consisting of 2-(cyclohex-3-en-1-ylmethoxy)acetaldehyde; 2-((2,4-dimethylcyclohex-3-en-1-yl)methoxy)acetaldehyde; and isomers thereof.
  • fragrance compounds having natural green, floral, fruity odor notes with a fresh aquatic note. These compounds can be used alone or incorporated into a fragrance composition and/or consumer product.
  • fragrance compounds having improved organoleptic properties. Additionally, there remains a need for fragrance compositions and consumer products comprising such fragrance compounds.
  • the present disclosure relates to compounds of formula (I), or an isomer thereof.
  • R 1 and R 2 are independently selected from hydrogen atom and methyl group.
  • the compounds of the present disclosure include, but are not limited to, 2-(cyclohex-3-en-1-ylmethoxy)acetaldehyde; 2-((2,4-dimethylcyclohex-3-en-1-yl)methoxy)acetaldehyde; and isomers thereof; and combinations thereof.
  • the presently disclosed compounds can have natural green, floral, fruity odor notes with a fresh aquatic note. These compounds can be used alone or incorporated into a fragrance composition to modify or enhance the odor of existing fragrance compositions, solvent, media, consumer products, and the like.
  • the term “about” or “approximately” means within an acceptable error range for the particular value as determined by one of ordinary skill in the art, which will depend in part on how the value is measured or determined, i.e., the limitations of the measurement system. For example, “about” can mean within 3 or more than 3 standard deviations, per the practice in the art. Alternatively, “about” can mean a range of up to 20%, preferably up to 10%, more preferably up to 5%, and more preferably still up to 1% of a given value. Alternatively, particularly with respect to biological systems or processes, the term can mean within an order of magnitude, preferably within 5-fold, and more preferably within 2-fold, of a value.
  • weight percent or “wt-%” is meant to refer to the quantity by weight of a component in a material as a percentage of the total wet weight of the material (i.e., a fragrance formulation). Unless otherwise specified, all amounts expressed as a percentage herein represent the amount in weight percent.
  • fragment composition means the same to refer to a perfumed composition that is a mixture of fragrance compounds including for example, alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpene hydrocarbons, nitrogenous or sulphurous heterocyclic compounds and essential oils of natural or synthetic origin, which are admixed so that the combined odors of the individual components produce a pleasant or desired fragrance.
  • fragrance composition is a mixture of fragrance compounds including for example, alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpene hydrocarbons, nitrogenous or sulphurous heterocyclic compounds and essential oils of natural or synthetic origin, which are admixed so that the combined odors of the individual components produce a pleasant or desired fragrance.
  • fragrance compounds including for example, alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpene hydrocarbon
  • fragrance compositions can be a mixture of any number of fragrance compounds.
  • fragrance compositions include “simple accords”, e.g., having fewer than 10 fragrance compounds, and “complex fragrances”, e.g., having more than 30 fragrance compounds.
  • the fragrance compositions of the present disclosure can be a combination of 2 or more accords.
  • the term “improving” is understood to mean raising a fragrance composition to a more desirable character
  • the term “enhancing” is understood to mean making the fragrance composition greater in effectiveness, such as strength
  • the term “modifying” is understood to mean providing the fragrance composition with a change in character.
  • the term “isomers” refers to different compounds that have the same molecular formula but differ in arrangement and configuration of the atoms.
  • the term “stereoisomer” refers to any of the various stereo isomeric configurations which may exist for a given compound of the presently disclosed subject matter and includes geometric isomers. It is understood that a substituent may be attached at a chiral center of a carbon atom. Therefore, the presently disclosed subject matter includes enantiomers, diastereomers or racemates of the compound.
  • substitutional isomers refers to different compounds which have the same numbers of, and types of, atoms but the atoms are connected differently.
  • the term “diastereoisomers” refers to stereoisomers that have at least two asymmetric atoms, but which are not mirror-images of each other.
  • the absolute stereochemistry is specified according to the Cahn-Ingold-Prelog R-S system. When a compound is a pure enantiomer the stereochemistry at each chiral carbon may be specified by either R or S.
  • Resolved compounds whose absolute configuration is unknown can be designated (+) or (-) depending on the direction (dextro or levorotatory) which they rotate plane polarized light at the wavelength of the sodium D line.
  • the compounds of the presently disclosed subject matter contain one or more asymmetric centers and may thus give rise to enantiomers, diastereomers, and other stereoisomeric forms that may be defined, in terms of absolute stereochemistry, as (R)- or (S)-.
  • the presently disclosed subject matter is meant to include all such possible isomers, including racemic mixtures, optically pure forms and intermediate mixtures.
  • Optically active (R)- and (S)-isomers may be prepared using chiral synthons or chiral reagents, or resolved using conventional techniques. If the compound contains a double bond, the substituent may be E or Z configuration. If the compound contains a disubstituted cycloalkyl, the cycloalkyl substituent may have a cis- or trans-configuration. All tautomeric forms are also intended to be included.
  • enantiomers refers to a pair of stereoisomers that are non-superimposable mirror images of each other.
  • a 1:1 mixture of a pair of enantiomers is a “racemic” mixture. The term is used to designate a racemic mixture where appropriate.
  • fragrance compounds that are able to impart natural green, floral, fruity odor notes with a fresh aquatic note.
  • the fragrance compounds can have the structure according to formula (I), or an isomer thereof, below.
  • R 1 and R 2 are independently selected from hydrogen atom and methyl group.
  • the fragrance compounds of the present disclosure can impart a number of different odors, including for example and not limitation, one or more natural green, floral, fruity, aldehydic, aquatic, muguet, vegetable, marine, milky, lily, citrus, spicy, almond, balsamic, and/or styrax odors.
  • the fragrance compounds of the present disclosure can impart multi-faceted odors having a combination of different odor notes.
  • R 1 is hydrogen atom
  • R 2 is hydrogen atom
  • a fragrance compound can be 2-(cyclohex-3-en-1-ylmethoxy)acetaldehyde, or an isomer thereof.
  • Such a fragrance compound can have natural green, floral, fruity, vegetable, aldehydic, milky, lily, citrus, aquatic, balsamic, and/or styrax odor, with unique freshness.
  • R 1 is methyl group
  • R 2 is methyl group
  • a fragrance compound can be 2-((2,4-dimethylcyclohex-3-en-1-yl)methoxy)acetaldehyde, or an isomer thereof.
  • Such a fragrance compound can have a floral, green, aldehydic, muguet, and/or marine odor.
  • the present disclosure also includes isomers, such as stereoisomers, diastereoisomers, and enantiomers, thereof.
  • fragrance compounds of the presently disclosed subject matter can be formulated into different fragrance compositions.
  • a fragrance composition in accordance with the presently disclosed subject matter can include one or more, two or more, or three or more of the fragrance compounds described above.
  • fragrance compounds into fragrance compositions span the range from “simple accords” ( ⁇ 10 fragrance compounds) to “complex fragrances” (>30 fragrance compounds).
  • full bodied fragrance compositions generally do not comprise less than about 30 fragrance compounds.
  • Such fragrance compositions can also contain or consist of at least one fragrance base, solvent, or combination thereof.
  • Said fragrance bases or solvents may be a liquid or a solid and typically do not significantly alter the olfactory properties of the fragrance compounds.
  • fragrance bases include an emulsifying system, encapsulating materials, natural or modified starches, polymers, gums, pectins, gelatinous or porous cellular materials, and waxes.
  • solvents include dipropylene glycol, propylene glycol, diethyl phthalate (DEP), diisononyl phthalate (DINP), benzyl benzoate, benzyl alcohol, isopropyl myristate (IPM), isopropyl palmitate (IPP/Deltyl Prime), butyl stearate, dioctyl adipate, triethyl citrate (TEC), methyl hydrogenated rosinate (CAS No.
  • terpenes e.g., Glidsol 100
  • paraffinic naphthenic solvent e.g., LPA-170 Solvent
  • isoalkanes e.g., Soltrol 170 Isoparaffin
  • isoparaffins isooctadecanol (e.g., Tego Alkanol 66)
  • phenoxyethanol diethylene glycol monoethyl ether (Carbitol low gravity), glycol ether (Methyl Carbitol), Dipropylene Glycol Methyl Ether (e.g., Dowanol DPM), Dipropylene Glycol Methyl Ether Acetate (e.g., Dowanol DPMA), Propylene glycol methyl ether (e.g., Dowanol PM Glycol Ether), Tripropylene Glycol Methyl Ether, Diisoheptyl Phthalate (e.g., Jayflex (registered trademark) 77
  • the amount of the fragrance compound of formula (I) present in a fragrance composition will depend on the formulation, but the compound of the present disclosure is typically present in an amount of from about 0.1% to about 30% by weight of the total fragrance composition. Typically a more preferred embodiment would contain between about 0.5% and about 20% by weight and a most preferred embodiment would contain between about 0.5% and about 10% by weight.
  • the one or more fragrance compounds of the present disclosure are formulated in a fragrance composition in amounts of from about 0.01% to about 99% by weight of the total fragrance composition, or from about 0.01% to about 90% by weight, or from about 0.5% to about 80% by weight, or from about 0.5% to about 70% by weight, or from about 0.5% to about 60% by weight, or from about 0.5% to about 50% by weight, or from about 0.5% to about 40% by weight, or from about 0.5% to about 30% by weight, or from about 0.5% to about 20% by weight, or from about 0.5% to about 10% by weight, or from about 0.5% to about 5% by weight, or from about 0.5% to about 2% by weight, or about 1% of the total fragrance composition.
  • the fragrance compositions of the present disclosure contain at least about 0.1% by weight. For example, at a concentration of at least about 0.1% by weight of the fragrance composition, some odor notes of the fragrance compounds can be detected. In certain embodiments, the fragrance compositions of the present disclosure contain at least about 0.5% by weight. In more preferred embodiments, the fragrance compositions of the present disclosure contain at least about 1% by weight. For example, at a concentration of at least about 1% by weight of the fragrance composition, the full character of the fragrance compounds can be detected.
  • the fragrance compositions of the present disclosure contain at least about 98.5% by weight of a fragrance compound, e.g., a compound of formula (I). In one embodiment, the fragrance composition contains 100% by weight of a fragrance compound, e.g., a compound of formula (I).
  • the fragrance compound is 2-(cyclohex-3-en-1-ylmethoxy)acetaldehyde, 2-((2,4-dimethylcyclohex-3-en-1-yl)methoxy)acetaldehyde, or an isomer, stereoisomer, diastereomer, or enantiomer thereof, or a combination thereof.
  • a fragrance composition can further include one or more additional fragrance accords or compounds.
  • the additional fragrance accords or compounds can be but are not limited to, one or more aldehydic compound(s), one or more animalic compound(s), one or more balsamic compound(s), one or more citrus compound(s), one or more floral compound(s), one or more fruity compound(s), one or more investigating compound(s), one or more green compound(s), one or more herbaceous compound(s), one or more marine compound(s), one or more mossy compound(s), one or more musk compound(s), one or more piney compound(s), one or more powdery compound(s), one or more spicy compound(s), and/or one or more woody compound(s), one or more amber compound(s), or combinations thereof.
  • Non-limiting examples of suitable aldehydic compounds include acetaldehyde C-8, acetaldehyde C-9, acetaldehyde C-10, adoxal, aldehyde C-8, aldehyde C-9, aldehyde C-10, aldehyde C-11, aldehyde C-12, aldehyde C-12 lauric, aldehyde C-12 MNA, aldehyde supra, cyclomyral, trans-2-decenal, cis-4-decenal, trans-4-decenal, 9-decenal, trans-2-dodecenal, 1-methyl-4-(4-methylpentyl)cyclohex-3-ene-1-carbaldehyde (VERNALDEHYDE (registered trademark)), myrac aldehyde, precyclemone B, undecylenic aldehyde, and combinations thereof.
  • VNALDEHYDE registered trademark
  • Non-limiting examples of an animalic compound include civet, p-cresol, cresyl methyl ether, 5-cyclohexadecen-1-one (AMBRETONE (registered trademark)), indole, 2-methyl-5-(5,5,6-trimethylbicyclo[2.2.1]hept-2-yl)cyclohexanone (ALDRON (registered trademark)), 17-oxacycloheptadec-6-en-1-one (ambrettolide), skatole, 2,5,5-trimethyl-1,3,4,4a,6,7-hexahydronaphthalen-2-ol (ambrinol), and combinations thereof.
  • Non-limiting examples of a balsamic compound include benzy salicylate, cylohexyl salicylate, isopropoxy ethyl salicylate, phenethyl salicylate, styrax oil, and combinations thereof.
  • Non-limiting examples of a citrus compound include delta-3-carene, citral, citronellal, DH-L-citronellol, L-cintronellol, decanal, limonene, myrcenol, DH-myrcenol, nootkatone, sinensal, rhubafuran, bergamot oil, grapefruit oil, lemon oil, lime oil, orange oil, mandarin oil, tridecene-2-nitrile, and/or yuzu core base.
  • Non-limiting examples of a floral compound include acetanisole, alpha amyl cinnamaldehyde, anisyl acetate, anisic aldehyde, benzyl acetate, bourgeonal, butyl acetate, L-citrol, cyclamen aldehyde, cyclohexyl lactone, delta-damascone, 9-decen-1-ol, dimethyl benzyl carbinol, farnesal, L-farnesal, L-dihydrofarnesal (BIOMUGUET (registered trademark)), ethyl linalool, farnesol, L-dihydrofarnesol (BIOCYCLAMOL (registered trademark)), 3-(3-isopropylphenyl)butanal (FLORHYDRAL (registered trademark)), 3-(4-ethylphenyl)-2,2-dimethylpropanal (floralozone), hex
  • Non-limiting examples of a fruity compound include aldehyde C-16, allyl caproate, allyl cyclohexyl propionate, allyl heptanoate, amyl acetate, benzaldehyde, L-citronellyl acetate, L-citronellyl nitrile, 3a,4,5,6,7,7a-hexahydro-4,7-methano-1H-inden-5(or 6)-yl acetate (CYCLACET (registered trademark)), 3a,4,5,6,7,7a-hexahydro-1H-4,7-methanoinden-1-yl propanoate (CYCLAPROP (registered trademark)), damascenone, beta-decalactone, gamma-decalactone, diethyl malonate, dimethyl benzyl carbinol acetate, dimethyl benzyl carbinyl butyrate, dimethyl pheny
  • Non-limiting examples of a investigating compound include angelica lactone-alpha, caprylic acid, coumarin, ethyl fraison, ethyl vanillin, ethyl maltol (e.g., VELTOL PLUS), filbertone, 4-hydroxy-2,5-dimethyl-3(2H)-furanone (FURANEOL (registered trademark)), guaiacol, maple furanone, 2-acetyl pyrazine, 2,5-dimethyl pyrazine, vanillin and combinations thereof.
  • Non-limiting examples of a green compound include allyl amyl glycolate, cyclogalbanate, 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-Penten-1-one (DYNASCONE (registered trademark)), galbanolene, galbanum, trans-2-hexenal, cis-3-hexenol, cis-3-hexenyl acetate, cis-3-hexenyl butyrate, cis-3-hexenyl formate, cis-3-hexenyl salicyclate, liffarome, 2-methoxy-2-methylheptane, methyl octine carbonate, neofolione, 2,6-nonadienal, (2R,4S)-2-methyl-4-propyl-1,3-oxathiane (OXANE (registered trademark)), octahydro-5-methoxy-4,7-methano-1H-indene
  • Non-limiting examples of an herbaceous compound include anethol, bamboo ketone, canthoxal, carvacrol, L-carvone, clary sage natural oil, p-cymene, 2,6-dimethylheptan-2-ol (DIMETOL (registered trademark)), menthol, methyl salicylate, thymol, natural basil oil, natural eucalyptus oil, eucalyptol, sweet natural fennel oil, natural cedar leaf oil, and combinations thereof.
  • Non-limiting examples of a marine compound include 8-methyl-1,5-benzodioxepin-3-one (Calone (registered trademark) 1951), 3-(4-ethylphenyl)-2,2-dimethylpropanal (floralozone), 4-tert-butylphenylacetonitrile (MARENIL (registered trademark)), 4-[(3E)-4,8-dimethylnona-3,7-dienyl]pyridine (MARITIMA (registered trademark)), myrac aldehyde, ULTRAZUR (registered trademark), and combinations thereof.
  • MARENIL registered trademark
  • MARITIMA registered trademark
  • Non-limiting examples of a mossy compound include hinokitiol, isobutyl quinolone, isopropyl quinolone and/or methyl 2,4-dihydroxy-3,6-dimethylbenzoate (oakmoss#1), and combinations thereof.
  • Non-limiting examples of a musk compound include 17-oxacycloheptadec-6-en-1-one (ambrettolide), 5-cyclohexadecen-1-one (AMBRETONE (registered trademark)), (3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan (AMBROXAN (registered trademark)), 2,2,6-trimethyl-alpha-propylcyclohexanepropanol (DEXTRAMBER (trademark)), 16-oxacyclohexadecan-1-one (EXALTOLIDE (registered trademark)), 4,6,6,7,8,8-hexamethyl-1,3,4,6,7,8-hexahydro-cyclopenta[g]-isochromene (GALAXOLIDE (registered trademark)), (12E)-1-oxacyclohexadec-12-
  • Non-limiting examples of a piney compound include l-borneol, l-bornyl acetate, camphene, camphor gum powder, dihydroterpineol, beta-pinene, and combinations thereof.
  • Non-limiting examples of a spicy compound include acetyl isoeugenol, delta-caryophyllene, cinnamaldehyde, cuminaldehyde, eugenol, isoeugenol, perilla aldehyde, cardamom oil, clove oil, ginger extract, ginger oil, black pepper extract and combinations thereof.
  • Non-limiting examples of a woody and/or amber compound include amber core, amber xtreme, 4aR,5R,7aS,9R)-octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-methanoazuleno[5,6-d]-1,3-dioxole (AMBROCENIDE (registered trademark)), ((3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan (AMBROXAN), 2-ethyl-4-(2,2,3-trimethyl-3-cyclo-penten-1-yl)-2-buten-1-ol (BACDANOL (registered trademark)), ethoxymethoxycyclododecane (Boisambrene Forte (registered trademark)), 1,1,2,3,3-pentamethyl-2,5,6,7-
  • the additional fragrance compounds are formulated in a composition in an amount of from about 0.001% to about 99% by weight, or from about 0.01% to about 90% by weight, or from about 0.1% to about 80% by weight, or from about 1% to about 70% by weight, or from about 2% to about 60% by weight, or from about 5% to about 50% by weight, or from about 10% to about 40% by weight, or from about 15% to about 30% by weight, or from about 20% to about 25% by weight.
  • the present disclosure provides methods to modify, enhance, or improve the odor properties of a fragrance composition by adding an olfactory effective quantity of the compounds of the present disclosure, e.g., a compound of formula (I), to the fragrance composition.
  • an olfactory effective quantity means the amount of said compound in a fragrance composition in which the individual component will contribute its characteristic olfactory properties, for example an olfactory property found to be more hedonically appealing.
  • a person of ordinary skill in the art may optimize the olfactory effect of the fragrance composition based on the incorporation of a fragrance compound of the present disclosure.
  • the olfactory effective quantity of the compounds of formula (I) in a fragrance composition will depend on the formulation, but the olfactory effective quantity of the compounds of the present disclosure is typically from about 0.1% to about 20% by weight of the fragrance composition.
  • the fragrance compound may be used individually, or a part of mixture such that the sum of the effects of all fragrance ingredients present in the mixture yields a higher hedonistic rating. Therefore, the compound embodied in the present disclosure can be employed to modify the characteristics of existing fragrance composition via their own olfactory properties or through additively effecting the contributions of other ingredient(s) present within the said composition.
  • the quantity will vary widely depending on the other ingredients present, their relative amounts, the desired effect and the nature of the product.
  • the fragrance compounds and compositions of the present disclosure can be formulated as part of a consumer product.
  • the fragrance compounds and/or compositions can be used in perfumes, colognes, shampoos, rinses, skin cares, body shampoos, body rinses, body powders, air fresheners, deodorants, baths, foods, snacks, beverages, and the like, if necessary in combination with auxiliary materials.
  • a compound of formula (I) can be employed alone or incorporated into fragrance compositions, which can advantageously be used in a wide variety of consumer products.
  • the consumer products can be those intended to perfume a suitable substrate.
  • the term “substrate” means any surface to which the consumer product can be applied without causing any undue adverse effect.
  • the substrate can be a wide range of materials including human or animal skin or hair, paper (e.g., fragranced paper), air in a room, fabric, furnishings, dishes, hard surfaces, and related materials.
  • substrates can include body surfaces such as, for example, hair and skin.
  • the present disclosure provides a consumer product comprising: (a) at least one compound of formula (I); and (b) a consumer product base.
  • consumer product base means a composition for use as a consumer product to fulfill the specific purpose of the consumer product, such as cleaning, softening, and caring or the like.
  • the present disclosure also provides a method for improving, enhancing, or modifying the odor properties of a consumer product base by adding thereto an olfactory effective amount of at least one compound of formula (I).
  • the compound described herein may be employed in a consumer product base simply by directly mixing at least one compound of formula (I), or a fragrance composition comprising at least one compound of formula (I), with the consumer product base, or the compound described herein can, in an earlier step, be entrapped with an entrapment material, for example, polymers, capsules, microcapsules and nanocapsules, liposomes, film formers, absorbents such as carbon or zeolites, cyclic oligosaccharides and mixtures thereof, or it can be chemically bonded to substrates, which are adapted to release the fragrance molecule upon application of an external stimulus such as light, enzymes, or the like, and then mixed with the consumer product base.
  • an entrapment material for example, polymers, capsules, microcapsules and nanocapsules, liposomes, film formers, absorbents such as carbon or zeolites, cyclic oligosaccharides and mixtures thereof, or it can be chemically bonded to substrates, which
  • the present disclosure additionally provides a method of manufacturing a perfumed consumer product, comprising incorporating a compound of formula (I), as a fragrance ingredient, either by directly admixing the compound to the consumer product base, or by admixing a fragrance composition comprising a compound of formula (I) with a consumer product base (i.e. incorporating the compound into the fragrance composition prior to admixing with the consumer product base).
  • Admixing can be performed using conventional techniques and methods.
  • the odor notes of a consumer product base can be improved, enhanced, or modified.
  • the consumer product base can be modified to improve or enhance natural green, floral odor notes with a fresh aquatic note
  • the consumer products of the present disclosure can be, but are not limited to, air care products (e.g., candles, aerosols, air fresheners, liquid electric air fresheners, fragrance diffusers, gel air fresheners, plug-in air fresheners and oils, wax melts, etc.); baby care products (e.g., consumer products relating to disposable absorbent and/or non-absorbent articles, including adult incontinence garments, bibs, diapers, training pants, infant and toddler care wipes; and personal care products including hand soaps, shampoos, lotions, shower gels, and clothing); fabric and home care products (e.g., consumer products for fabric conditioning (including softening), laundry detergency, laundry and rinse additive and/or care, bleach, dryer sheets, perfume beads, air care, car care, dishwashing, hard surface cleaning and/or treatment, and other cleaning for consumer and or institutional use, etc.); personal care products (e.g., lotions, creams, moisturizers, body washes, hand soaps
  • the fragrance composition is admixed with a consumer product wherein the composition is present in an amount from about 0.0001 to about 90% weight/weight (w/w), or from about 0.001 to about 75% w/w, or from about 1 to about 50% w/w, or from about 5 to about 25% w/w, or from about 10 to about 15% w/w, and values in between.
  • the fragrance composition admixed with the consumer product comprises 2-(cyclohex-3-en-1-ylmethoxy)acetaldehyde, 2-((2,4-dimethylcyclohex-3-en-1-yl)methoxy)acetaldehyde, or an isomer, stereoisomer, diastereomer, or enantiomer thereof, or a combination thereof.
  • the consumer product base additionally includes one or more bases, solvents, and combinations thereof.
  • bases can include, but are not limited to, essential oils, lactones, aldehydes, alcohols, ketones, nitriles, esters, amides, oximes, and other fragrant compounds and perfuming co-ingredients.
  • the solvents can include, but are not limited to, dipropylene glycol, propylene glycol, diethyl phthalate (DEP), diisononyl phthalate (DINP), benzyl benzoate, benzyl alcohol, isopropyl myristate (IPM), isopropyl palmitate (IPP/Deltyl Prime), butyl stearate, dioctyl adipate, triethyl citrate (TEC), methyl hydrogenated rosinate (CAS No.
  • terpenes e.g., Glidsol 100
  • paraffinic naphthenic solvent e.g., LPA-170 Solvent
  • isoalkanes e.g., Soltrol 170 Isoparaffin
  • isoparaffins isooctadecanol, (e.g., Tego Alkanol 66)
  • phenoxyethanol diethylene glycol monoethyl ether (Carbitol low gravity), glycol ether (Methyl Carbitol), Dipropylene Glycol Methyl Ether (e.g., Dowanol DPM), Dipropylene Glycol Methyl Ether Acetate (e.g., Dowanol DPMA), Propylene glycol methyl ether (e.g., Dowanol PM Glycol Ether), Tripropylene Glycol Methyl Ether, Diisoheptyl Phthalate (e.g., Jayflex (registered trademark)
  • the resultant mixture was extracted with toluene (100 mL ⁇ 3).
  • the combined organic layers were washed with brine (100 mL ⁇ 2) and water (100 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure.
  • the crude product was purified by distillation under reduced pressure (59.6 - 66.7 o C /20 Pa) to yield 4-((2,2-diethoxyethoxy)methyl)cyclohex-1-ene as a colorless oil (176 g, Yield: 87%).
  • the odor was earthy, green and mushroom.
  • the crude product was purified by distillation under reduced pressure (59.2 - 59.6 o C /230 Pa) to yield 2-(cyclohex-3-en-1-ylmethoxy)acetaldehyde as a colorless oil (93.3 g, Yield: 79%).
  • the odor was natural green, floral, fruity, vegetable, aldehydic, milky, lily, citrus, aquatic, balsamic, and styrax.
  • the reaction mixture was heated to 120 o C and stirred for 24 hours.
  • the reaction was cooled to room temperature and extracted with toluene (101 mL ⁇ 3).
  • the combined organic layers were washed with brine (101 mL ⁇ 2) and water (101 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure.
  • the crude product was purified by distillation under reduced pressure (88.9 - 90.4 o C /89 Pa) to yield 4-((2,2-diethoxyethoxy)methyl)-1,3-dimethylcyclohex-1-ene as a colorless oil (59.6 g, Yield: 64%).
  • the odor was vegetable, earthy, and green.
  • Fragrance compositions and shampoo formulations with 2-(cyclohex-3-en-1-ylmethoxy)acetaldehyde A perfume composition with a floral fruity aquatic note was prepared from the compound of Example 2 (2-(cyclohex-3-en-1-ylmethoxy)acetaldehyde) to demonstrate its use in a shampoo.
  • the formulation, with and without 2-(cyclohex-3-en-1-ylmethoxy)acetaldehyde, is provided in Table 1, below.
  • the fragrance was used at 0.8% in a shampoo and a panel of five experts evaluated the samples.
  • composition of this Example using the compound of Example 2 (2-(cyclohex-3-en-1-ylmethoxy)acetaldehyde) was found to have added floral aquatic notes and total volume of notes, compared to the composition of this example without the compound of Example 2.
  • the compound of Example 2 also gives cleanliness to the fragrance composition. It’s excellent connotation for shampoo application.
  • Fragrance compositions and fabric softener formulations with 2-(cyclohex-3-en-1-ylmethoxy)acetaldehyde A perfume composition with a white floral note was prepared from the compound of Example 2 (2-(cyclohex-3-en-1-ylmethoxy)acetaldehyde) to demonstrate its use in a fabric softener.
  • the formulation, with and without 2-(cyclohex-3-en-1-ylmethoxy)acetaldehyde, is provided in Table 2, below.
  • the fragrance was used at 1.0% in a fabric softener and a panel of five experts evaluated the samples.
  • composition of this Example using the compound of Example 2 (2-(cyclohex-3-en-1-ylmethoxy)acetaldehyde) was found to add a more natural and fresher character to the fragrance composition.
  • the compound of Example 2 gives watery white floral facet which is a key character of this fragrance.
  • fragrance compounds having natural green, floral, fruity odor notes with a fresh aquatic note. These compounds can be used alone or incorporated into a fragrance composition and/or consumer product.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention concerne la synthèse et l'application de nouveaux composés ayant des caractéristiques de parfum uniques et souhaitées. Les composés de parfum de la présente invention peuvent être utilisés seuls ou incorporés dans des compositions de parfum et/ou des produits de consommation pour modifier ou améliorer l'odeur des compositions de parfum et/ou des produits de consommation.
PCT/JP2019/021862 2018-06-01 2019-05-31 Substance de parfum WO2019230974A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201862679384P 2018-06-01 2018-06-01
US62/679,384 2018-06-01

Publications (1)

Publication Number Publication Date
WO2019230974A1 true WO2019230974A1 (fr) 2019-12-05

Family

ID=68697588

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2019/021862 WO2019230974A1 (fr) 2018-06-01 2019-05-31 Substance de parfum

Country Status (1)

Country Link
WO (1) WO2019230974A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112385820A (zh) * 2020-11-18 2021-02-23 浙江金味香料有限公司 一种芒果味香精
WO2023232235A1 (fr) * 2022-05-31 2023-12-07 Symrise Ag 1-(méthoxyméthyl)-2-méthyl-benzène en tant que parfum

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61115041A (ja) * 1984-11-12 1986-06-02 Kao Corp １（又は２あるいは３）−ホルミルプロポキシシクロヘキサン及びこれを含有する香料組成物
JPS61268643A (ja) * 1985-05-22 1986-11-28 Kao Corp シス（又はトランス）−１−〔１′（又は２′あるいは３′）−ホルミルプロポキシ〕−４−ｔｅｒｔ−ブチルシクロヘキサン及びこれを含有する香料組成物
JPH1084989A (ja) * 1996-09-18 1998-04-07 T Hasegawa Co Ltd 光学活性α−イオノンの製造方法
JP2010506861A (ja) * 2006-10-18 2010-03-04 ジボダン エス エー 匂い物質として有用な２，２，３−トリメチルシクロペンタ−３−エンカルバルデヒド誘導体
JP2013256470A (ja) * 2012-06-13 2013-12-26 Takasago Internatl Corp カンフォレン誘導体及びそれを含有する香料組成物
JP2014148614A (ja) * 2013-02-01 2014-08-21 Takasago Internatl Corp 香料組成物
WO2017046071A1 (fr) * 2015-09-16 2017-03-23 Firmenich Sa Ingrédient pour parfum vert au muguet
WO2017214455A1 (fr) * 2016-06-08 2017-12-14 Takasago International Corporation (Usa) Matière parfumante

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61115041A (ja) * 1984-11-12 1986-06-02 Kao Corp １（又は２あるいは３）−ホルミルプロポキシシクロヘキサン及びこれを含有する香料組成物
JPS61268643A (ja) * 1985-05-22 1986-11-28 Kao Corp シス（又はトランス）−１−〔１′（又は２′あるいは３′）−ホルミルプロポキシ〕−４−ｔｅｒｔ−ブチルシクロヘキサン及びこれを含有する香料組成物
JPH1084989A (ja) * 1996-09-18 1998-04-07 T Hasegawa Co Ltd 光学活性α−イオノンの製造方法
JP2010506861A (ja) * 2006-10-18 2010-03-04 ジボダン エス エー 匂い物質として有用な２，２，３−トリメチルシクロペンタ−３−エンカルバルデヒド誘導体
JP2013256470A (ja) * 2012-06-13 2013-12-26 Takasago Internatl Corp カンフォレン誘導体及びそれを含有する香料組成物
JP2014148614A (ja) * 2013-02-01 2014-08-21 Takasago Internatl Corp 香料組成物
WO2017046071A1 (fr) * 2015-09-16 2017-03-23 Firmenich Sa Ingrédient pour parfum vert au muguet
WO2017214455A1 (fr) * 2016-06-08 2017-12-14 Takasago International Corporation (Usa) Matière parfumante

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DATABASE REGISTRY [online] 28 October 2010 (2010-10-28), "CN Acetaldehyde, 2-[(6-methyl-3-cyclohexene -1-yl)methoxy]- ( CA INDEX NAME)", Database accession no. RN 1247821-26-6 *
KUGATOVA-SHEMYAKINA, G. P. ET AL.: "Condensation of vinyl ethers with aldehydes of 3- and 6-cyclohexene and cyclohexane series", ZHURNAL OBSHCHEI KHIMII, vol. 2, no. 3, 1966, pages 442 - 446, ISSN: 0044-460X *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112385820A (zh) * 2020-11-18 2021-02-23 浙江金味香料有限公司 一种芒果味香精
CN112385820B (zh) * 2020-11-18 2022-07-12 浙江金味香料有限公司 一种芒果味香精
WO2023232235A1 (fr) * 2022-05-31 2023-12-07 Symrise Ag 1-(méthoxyméthyl)-2-méthyl-benzène en tant que parfum

Similar Documents

Publication Publication Date Title
EP3468527B1 (fr) Matériau de parfum
JP7189285B2 (ja) フレグランス物質
US9643913B2 (en) Organoleptic compounds
WO2019230974A1 (fr) Substance de parfum
BR102016006629A2 (pt) composto, formulação de fragrância, método para melhorar, intensificar ou modificar uma formulação de fragrância, e, produto de fragrância
US20170174650A1 (en) Novel organoleptic compounds and their use in flavor and fragrance compositions
JP7312195B2 (ja) フレグランスおよびフレーバー物質
EP3802513B1 (fr) Matériaux de parfum
WO2019173776A1 (fr) Substances parfumantes et aromatiques dérivées de 1-(4-méthylcyclohex-1-én-1-yl) ethan-1-one
CN108697598B (zh) 感官化合物
WO2019199882A1 (fr) Utilisation de (s)-méthoxymélonal dans des compositions de parfum et d'arôme
WO2019173772A1 (fr) Substances parfumantes et aromatiques à partir de 1-(2-hydroxy-4-méthylcyclohexyl)-éthanone

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 19812029

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 19812029

Country of ref document: EP

Kind code of ref document: A1