Aliphatic cyclopentanones as malodor counteracting ingredients

Abstract

The present disclosure relates to the use of aliphatic cyclopentanones as malodor counteracting ingredients. Malodor counteraction compositions to reduce the perception of malodor is also described herein.

Description

[0001] Firmenich SA

[0002] ALIPHATIC CYCLOPENTANONES AS MALODOR COUNTERACTING INGREDIENTS

[0003] TECHNICAL FIELD

[0004] The present disclosure relates to volatile compositions to limit, decrease or eliminate the perception of malodor and methods of use thereof. The present disclosure also relates to consumer products containing the said compositions.

[0005] DESCRIPTION OF RELATED ART

[0006] Smells perceived as malodorous exist in many environments and are experienced in our daily lives. The odorants eliciting this negative association may be commercial or residential environment malodors which can be generated by waste products, trash receptacles, toilets, cat litter, and food handling and processing. Toilet, kitchen, and body malodor are just a few of the common environmental sources of malodors in daily life. Malodors are usually complex mixtures of more than one malodorant compound which may typically include various amines, thiols, sulfides, short chain aliphatic and unsaturated acids, e.g., fatty acids, and their derivatives. Residential or body related malodors are typically due to various chemical compounds such as indole, skatole, and methanethiol found in feces malodor; piperidine and morpholine found in urine; pyridine and triethyl amine found in kitchen and garbage malodors; geonol (geosmin), 1-octen-3-ol, 1-octen-3-one, dimethyl disulfide, dimethyl trisulfide, 3-methyl- 1-butanol, and 4-methyl-3-hexenoic acid, among others, found in laundry malodor; and short chain fatty acids, such as 3-methyl-3-hydroxyhexanoic acid, 3-methylhexanoic acid, 3-methyl-2- hexenoic acid, isononanoic acid, and 4-ethyl octanoic acid, among others, found in axillary malodors.

[0007] There is an ongoing need for malodor counteracting (MOC) technologies for decreasing or suppressing the perception of malodors. Various approaches exist to achieve such a goal with MOC compositions, and include one or more of the following: i) odor coverage (which relates to superimposing the malodor with a pleasant stronger odor), ii) odor antagonism (which relates to either suppressing or decreasing the perception by blocking the olfactory receptors involved in decoding the odorants perceived as bad, or iii) odor sequestration produced by the chemical or physical interception of the malodorant molecules or by preventing their formation.

[0008] Odor coverage is generally very difficult because the chemicals responsible for the malodor elicit extremely powerful smells and can have much lower detection thresholds than the odorants used to mask them. As a result, excessive amounts of masking compositions or compounds are needed to achieve an acceptable malodor counteracting action.

[0009] SUMMARY

[0010] The present disclosure provides ingredients, compositions, and methods for their use for reducing, preventing, or inhibiting the perception of such malodor by blocking or modulating the olfactory receptors involved in malodor olfaction. The use of the compositions described herein in consumer products is also an object of the present disclosure.

[0011] In a first aspect, the disclosure provides use of a malodor antagonizing compound to reduce a malodor, wherein the malodor antagonizing compound is a compound of formula (I): in the form of any one of its stereoisomers or a mixture thereof, wherein n is 1 or 2, and the bond a is either present or absent. In some embodiments, the use comprises introducing the malodor antagonizing compound to a closed space or a surface, wherein the closed space or the surface comprises a malodor agent that causes a perception of malodor by a human subject.

[0012] In a second aspect, the disclosure provides a method of reducing a perception of malodor by a human subject, the method comprising introducing a malodor antagonizing compound to a closed space or a surface, wherein the closed space or the surface comprises a malodor agent that causes the perception of malodor by a human subject, and wherein the malodor antagonizing compound is a compound of formula (I) in the form of any one of its stereoisomers or a mixture thereof, wherein n is 1 or 2, and the bond a is either present or absent.

[0013] In a third aspect, the disclosure provides a malodor counteracting composition, which comprises a malodor antagonizing compound, wherein the malodor antagonizing compound is a compound of formula (I) in the form of any one of its stereoisomers or a mixture thereof, wherein n is 1 or 2, and the bond a is either present or absent.

[0014] In a fourth aspect, the present disclosure provides a consumer product comprising the malodor counteracting composition of the third aspect. Further aspects, and embodiments thereof, are set forth below in the Detailed Description, the Drawings, the Abstract, and the Claims.

[0015] BRIEF DESCRIPTION OF DRAWINGS

[0016] FIG. 1 shows a comparison of ingredients by quantifying each ingredient’s percent inhibition and the IC50 from binary mixtures with olfactory receptor 0R11A1.

[0017] FIG. 2 shows a comparison of ingredients by quantifying each ingredient’s percent inhibition and the IC50 from binary mixtures with olfactory receptor OR52A5.

[0018] FIG. 3 shows the response of odorant receptor 0R11A1 to vehicle control (stars), geosmin (open circles), and a binary mixture of geosmin and a malodor counteracting ingredient according to the present disclosure (solid circles).

[0019] FIG. 4 shows the response of odorant receptor OR52A5 to vehicle control (stars), isononanoic acid (open circles), and a binary mixture of isononanoic acid and a malodor counteracting ingredient according to the present disclosure (solid circles).

[0020] FIG. 5 shows the impact of a malodor counteracting ingredient on the perceived intensity of geosmin. The bars labelled with different letters (e.g., A and B above bars) are significantly different (p < .05, one-tailed) while bars labelled with the same letter are not.

[0021] FIG. 6 shows the odor hedonics of a mixture of a malodor counteracting ingredient and geosmin versus geosmin alone. The bars labelled with different letters (e.g., A and B above bars) are significantly different (p < .05, one-tailed) while bars labelled with the same letter are not.

[0022] FIG. 7 shows the impact of a malodor counteracting ingredient on the perceived intensity of isononanoic acid. The bars labelled with different letters (e.g., A and B above bars) are significantly different (p < .05, one-tailed) while bars labelled with the same letter are not.

[0023] DETAINED DESCRIPTION

[0024] The following Detailed Description sets forth various aspects and embodiments provided herein. The description is to be read from the perspective of the person of ordinary skill in the relevant art. Therefore, information that is well known to such ordinarily skilled artisans is not necessarily included.

[0025] Definitions

[0026] As used herein, the terms “a”, “an”, or “the” means “one or more” or “at least one” unless otherwise stated.

[0027] While compositions and methods are described in terms of “comprising,” “containing,” or “including” various components or steps, the compositions and methods can also “consist essentially of” or “consist of” the various components, substances and steps. As used herein the term “consisting essentially of” shall be construed to mean including the listed components, substances or steps and such additional components, substances or steps which do not materially affect the basic and novel properties of the composition or method. In some embodiments, a composition in accordance with embodiments of the present disclosure that “consists essentially of” the recited components or substances does not include any additional components or substances that alter the basic and novel properties of the composition.

[0028] Unless defined otherwise, all technical and scientific terms used herein have the same meaning as is commonly understood by one of skill in the art to which this specification pertains.

[0029] It should be understood that any numerical range recited herein is intended to include all sub-ranges subsumed therein. For example, a range of “1 to 10” is intended to include all subranges between and including the recited minimum value of 1 and the recited maximum value of 10; that is, having a minimum value equal to or greater than 1 and a maximum value of equal to or less than 10. Because the disclosed numerical ranges are continuous, they include every value between the minimum and maximum values. Unless expressly indicated otherwise, the various numerical ranges specified in this application are approximations.

[0030] As used herein, and unless otherwise indicated, the term “about” or “approximately” means an acceptable error for a particular value as determined by one of ordinary skill in the art, which depends in part on how the value is measured or determined. In certain embodiments, the term “about” or “approximately” means within 1 , 2, 3, or 4 standard deviations. In certain embodiments, the term “about” or “approximately” means within 50%, 20%, 15%, 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%, 1%, 0.5%, or 0.05% of a given value or range.

[0031] Throughout the present disclosure, various publications may be incorporated by reference. Should the meaning of any language in such publications incorporated by reference conflict with the meaning of the language of the present disclosure, the meaning of the language of the present disclosure shall take precedence, unless otherwise indicated.

[0032] Throughout the present disclosure, various chemical names and structures may be recited. Unless otherwise stated, any stereoisomers, such as enantiomers, diastereomers, anomers, epimers, and the like; and geometric isomers, such as cis / trans or E / Z isomers, of the recited chemical name or structure are contemplated. As would be understood by those of ordinary skill in the art, stereoisomers may possess one stereocenter, giving rise to enantiomers, or more than one stereocenter, giving rise to diastereomers, each stereocenter having one of two different stereochemistries (i.e. , R or S). Enantiomers may be characterized by their ability to rotate oncoming plane-polarized light to the right, designated as dextrorotatory, “(+)” or “D”, or to the left, designated as levorotatory, “(-)” or “L”. Enantiomers may exist as racemic mixtures or scalemic mixtures. Geometric isomers refer to isomers in which the spatial relationship of atoms around a double bond are different, typically designated E or Z according to conventional understanding in the chemical art. Geometric isomers may also exist as mixtures of E and Z isomers. All of the aforementioned isomeric variations of the chemical names or structures recited herein are included.

[0033] Uses and Methods

[0034] In certain aspects, the disclosure provides use of a malodor antagonizing compound to reduce a malodor, wherein the malodor antagonizing compound is a compound of formula (I): in the form of any one of its stereoisomers or a mixture thereof, wherein n is 1 or 2, and the bond a is either present or absent. In some embodiments, the use comprises introducing the malodor antagonizing compound to a closed space or a surface, wherein the closed space or the surface comprises a malodor agent that causes a perception of malodor by a human subject.

[0035] In certain related aspects, the disclosure provides a method of reducing a perception of malodor by a human subject, the method comprising introducing a malodor antagonizing compound to a closed space or a surface, wherein the closed space or the surface comprises a malodor agent that causes the perception of malodor by a human subject, and wherein the malodor antagonizing compound is a compound of formula (I) in the form of any one of its stereoisomers or a mixture thereof, wherein n is 1 or 2, and the bond a is either present or absent.

[0036] Compounds of formula (I) are exemplary of aliphatic cyclopentanones, which are cyclopentanones having at least one aliphatic substituent. As used herein, the term “aliphatic” or “aliphatic group” refers to a saturated or unsaturated group having the fundamental properties of an aliphatic compound, consisting solely of carbon atoms and hydrogen atoms, and which is attached to the rest of the molecule by a chemical bond. Exemplary aliphatic groups include, but are not limited to, straight or branched alkyl and alkenyl groups.

[0037] In an embodiment, the compound of formula (I) is a compound of formula (la) (la), wherein n is 1 or 2.

[0038] In an embodiment, the compound of formula (I) is a compound of formula (lb),

[0039] The compound of formula (lb) is understood to be 2-(hex-5-en-1-yl)cyclopentan-1-one and includes its stereoisomers and any mixture thereof.

[0040] The uses and methods disclosed herein do not limit the means of introduction of the malodor antagonizing compound. For example, the malodor antagonizing compound can be formulated with any suitable carriers or other ingredients that are commonly used in consumer products, such as air care products, cleaning products, cosmetic products, perfuming products, and the like. For example, in some embodiments, the malodor antagonizing compound is introduced by spraying, a nebulizing, or by evaporation of a composition containing the malodor antagonizing compound, and the like.

[0041] The malodor antagonizing compound can be introduced in any suitable concentration, which will vary depending on the particular application. For example, in some embodiments, the introducing includes introducing the malodor antagonizing compound as part of a liquid composition at a concentration ranging from 1 ppm to 1000 ppm, or from 5 ppm to 500 ppm, or from 10 ppm to 100 ppm, by weight based on the total weight of the liquid composition. In some embodiments, introducing includes introducing the malodor antagonizing compound as part of a liquid composition at a concentration of 1 ppm, 5 ppm, 10 ppm, 20 ppm, 30 ppm, 40 ppm, 50 ppm, 60 ppm, 70 ppm, 80 ppm, 90 ppm, 100 ppm, 500 ppm, or 1000 ppm, by weight based on the total weight of the liquid composition. In some embodiments, the introducing comprises introducing the malodor antagonizing compound as part of a liquid composition at a concentration sufficient to antagonize binding of the malodor agent to one or more human olfactory receptors in the subject.

[0042] As used herein, the term “olfactory receptor”, or “OR” refers to one or more members of a family of G protein-coupled receptors (GPCRs) that are expressed in olfactory cells. Olfactory receptor cells can also be identified on the basis of morphology or by the expression of proteins specifically expressed in olfactory cells. Various OR family members may have the ability to act as receptors for odorants and induce an olfactory transduction cascade.

[0043] The terms “antagonists”, “inhibitor”, “blockers”, “suppressors”, “counteractants”, and “modulators” of olfactory receptors are used interchangeably to refer to inhibitory, blocking, suppressing, or modulating molecules identified using in vivo, ex vivo and in vitro assays for olfactory transduction, e.g., ligands, antagonists, and their homologs and mimetics. Inhibitors are compounds that, e.g., bind to, partially or totally block stimulation, decrease, suppress, prevent, delay activation, inactivate, desensitize, or down regulate olfactory transduction, e.g., antagonists. Activators are compounds that, e.g., bind to, stimulate, increase, open activate, facilitate, enhance activation, sensitize, or up regulate olfactory transduction, e.g., agonists. Modulators include compounds that, e.g., alter the interaction of a receptor with: extracellular proteins that bind activators or inhibitor (e.g., odorant-binding proteins, ebnerin and other members of the hydrophobic carrier family); G proteins; kinases (e.g., homologs of rhodopsin kinase and beta adrenergic receptor kinases that are involved in deactivation and desensitization of a receptor); and arrestins, which also deactivate and desensitize receptors.

[0044] The ability of malodor antagonizing compounds set forth herein to inhibit or antagonize binding of a malodor agent to an olfactory receptor may be determined by any suitable method readily selected by one of ordinary skill in the art, such as, for example, via an ex vivo cultured neuron assay, or via an in vitro assay using a cell line that expresses the olfactory receptor. Such assays for inhibitors and activators include, e.g., expressing OR family members in cells or cell membranes, applying putative modulator compounds, in the presence or absence of malodor molecules, e.g., geosmin, isononanoic acid, and the like, and then determining the functional effects on olfactory transduction, as described in the Examples below. Samples or assays comprising OR family members that are treated with a potential inhibitor are compared to control samples without the inhibitor to examine the extent of inhibition. Control samples (untreated with inhibitors but treated with the malodor) are assigned a relative maximal OR activity value of 100%. Inhibition of an OR is achieved when the normalized OR activity value relative to the control is about 80%, optionally 50% or 25-0%. Alternatively, in some embodiments, inhibition of an OR is achieved if the IC50 value of the antagonist compound is equal to or less than 1000 pM. Alternatively, in some embodiments, inhibition of an OR is achieved if the IC50 value of the antagonist compound is equal to or less than 100 pM. Alternatively, in some embodiments, inhibition of an OR is achieved if the IC50 value of the antagonist compound is equal to or less than 10 pM. In some embodiments, inhibition of an OR is achieved if the IC50 value of the antagonist compound is from 1 pM to 1000 pM, typically from 100 pM to 1000 pM. In an embodiment, the at least one olfactory receptor is a human OR11 A1 receptor or a human OR52A5 receptor.

[0045] The malodor whose perception is reduced is not particularly limited. The malodor includes a kitchen malodor, a latrine or bathroom malodor, a tobacco malodor, a pet malodor, a body malodor (such as a sweat malodor or an axillary malodor), and a laundry malodor.

[0046] Non-limiting examples of kitchen malodor include any type of malodor present in a residential or commercial kitchen including, but not limited to: kitchen garbage odors that may result from the disposal of raw or cooked meat, fish, vegetables, fruit and / or dairy products; odors experienced during food preparation, especially odors generated from raw fish, raw garlic and raw onions; cooking odors, especially odors produced when cooking meat, fish, onion and / or garlic; the odor of cooking oil used for frying foods; burnt odors that may originate from the over-cooking or burning of foods; odors originating from the kitchen sink drain; odors originating from in-sink disposal units; and, odors originating from a refrigerator.

[0047] Non-limiting examples of bathroom or latrine malodor include any malodor type of malodor present in a residential or public bathroom / restroom including, but not limited to: odors present immediately after the use of the toilet; lingering toilet odors; stale urine odor; and moldy or musty odors that often originate in damp areas of the bathroom such as around the bath or shower.

[0048] Non-limiting examples of tobacco malodor include the odor generated during smoking of cigarettes, cigars or tobacco pipes, or the stale smoke odor that lingers after use of tobacco products in a room, or the odor originating from an ash tray that comprises debris from cigarettes, cigars, or tobacco pipes.

[0049] Non-limiting examples of pet malodor include any type of odor associated with a domestic pet, especially a cat or a dog, and includes, but is not limited to: fecal odors from litter boxes; urine odors from litter boxes; lingering urine odors; wet-dog odor; and, pet-bed odor.

[0050] Non-limiting examples of body malodor include any type of odor produced by the human body including, but not limited to: axillary (armpit) odor, sweat odor, scalp odor, foot odor and vaginal odor. “Body malodor” may also mean an odor that originates on the human body and is transferred to another substrate such as a textile; this may include, for example, the odor of worn socks, or the odor of worn sportswear.

[0051] Non-limiting examples of laundry malodor include soils such as those found on mechanics' clothes; food handlers, especially butchers' and kitchen workers' clothes; sewer workers' clothes; bar tenders' clothes; fire fighters' clothes; farm clothes; athletic clothing; factory workers' clothes; heavy machinery operators' clothes, mold, odors found in laundry machines, and the like.

[0052] Without intending to be limited to any particular theory, residential, body, or laundry malodors are typically due to various malodor targets such as indole, skatole, dimethyl trisulfide, dimethyl disulfide, methanethiol, and butyric acid, found in feces malodor; piperidine and morpholine found in urine; pyridine and triethyl amine found in kitchen and garbage malodors; geonol (geosmin), 1-octen-3-ol, 1-octen-3-one, dimethyl disulfide, dimethyl trisulfide, 3-methyl-1-butanol, and 4-methyl-3-hexenoic acid, among others, found in laundry malodor; and short chain fatty acids, such as 3-methyl-3-hydroxyhexanoic acid, 3-methylhexanoic acid, 3-methyl-2-hexenoic acid, isononanoic acid, and 4-ethyl octanoic acid, among others, found in axillary malodors. Such materials act as activators, or agonists, of one or more olfactory receptors, leading to the perception of malodor. As used herein, "malodor target" is meant to designate a molecular component of the aforementioned malodors, such as latrine malodor, laundry malodor, or sweat malodor.

[0053] In an embodiment, the malodor comprises latrine malodor, laundry malodor, or sweat malodor. In another embodiment, the malodor comprises one or more malodor agents, which are agonists of the human OR11A1 receptor or the human OR52A5 receptor. Examples of agonists of the human OR11A1 receptor include, but are not limited to, geosmin, 2-ethylfenchol, fenchyl alcohol, patchouli alcohol, and the like. Examples of agonists of the human OR52A5 receptor include, but are not limited to, 4-ethyl octanoic acid, isononanoic acid (also referred to as 4-methyl octanoic acid), and the like. In an embodiment, the malodor comprises at least one malodor agent selected from the group consisting of geosmin, 2-ethylfenchol, fenchyl alcohol, patchouli alcohol, 4-ethyl octanoic acid, isononanoic acid, and any mixture thereof.

[0054] Malodor Antagonizing Compositions

[0055] In certain aspects, the present disclosure relates to a malodor counteracting composition for reducing a subject’s perception of malodor, the composition comprising a malodor antagonizing compound, which is a compound of formula (I), as described herein or any embodiments thereof, such as a compound of formula (la) or a compound of formula (lb).

[0056] The amount of the malodor antagonizing compound in the malodor counteracting composition is not particularly limited. In an embodiment, the malodor antagonizing compound is present in the composition at a concentration ranging from 0.0001% by weight to 99.9% by weight, or 0.0005% by weight to 90% by weight, or 0.001% by weight to 80% by weight, by based on the total weight of the malodor counteracting composition.

[0057] The malodor counteracting composition described herein may optionally comprise a perfumery solvent. A detailed description of the nature and type of solvents commonly used in perfumery, herein “perfumery solvent” cannot be exhaustive. However, exemplary solvents include, but are not limited to, solvents such as glycerol, dipropylene glycol and its monoether, 1 ,2,3-propanetriyl triacetate, dimethyl glutarate, dimethyl adipate 1 ,3-diacetyloxypropan-2-yl acetate, diethyl phthalate, isopropyl myristate, Abalyn® (rosin resins, available from Eastman), benzyl benzoate, benzyl alcohol, 2-(2-ethoxyethoxy)-1 -ethanol, tri-ethyl citrate or mixtures thereof. Naturally derived solvents, like glycerol or various vegetable oils such as palm oil, sunflower oil or linseed oil, may also be used. Other non-limiting perfumery solvents include limonene or other terpenes, isoparaffins such as those known under the trademark Isopar6(origin: Exxon Chemical) or glycol ethers and glycol ether esters such as those known under the trademark Dowanol6(origin: Dow Chemical Company), or hydrogenated castors oils such as those known under the trademark Cremophor6RH 40 (origin: BASF).

[0058] The amount of the perfumery solvent is not particularly limited. However, in some embodiments, the perfumery solvent is present in an amount from 0% to 50%, typically 0.1% to 15%, more typically 0.2% to 10%, by weight relative to the total weight of the composition.

[0059] The malodor counteracting composition described herein may further comprise a perfuming co-ingredient. As used herein, a perfuming co-ingredient refers to ingredients that impart a hedonic effect, i.e., used for the primary purpose of conferring or modulating an odor. In other words, such a co-ingredient, to be considered as being a perfuming one, must be recognized by a person skilled in the art as being able to impart or modify in a positive or pleasant way the odor of a composition, and not just as having an odor. Perfuming coingredients may impart an additional benefit beyond that of modifying or imparting an odor, such as long-lasting, blooming, malodor counteraction, antimicrobial effect, antiviral effect, microbial stability, or pest control.

[0060] The nature and type of the perfuming co-ingredients do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of his general knowledge and according to the intended use or application and the desired organoleptic effect. In general terms, these perfuming coingredients belong to chemical classes as varied as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogenous or sulphurous heterocyclic compounds, and essential oils. Perfuming co-ingredients can be of natural or synthetic origin. Suitable perfumery 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, known as properfume or profragrance.

[0061] The malodor counteracting composition described herein may optionally comprise a fragrance modulator.

[0062] Fragrance modulators, also known as fixatives, are agents having the capacity to affect the manner in which the odor, and in particular the evaporation rate and intensity, of the compositions incorporating said modulator can be perceived by an observer or user thereof, over time, as compared to the same perception in the absence of the modulator. In particular, the modulator allows prolonging the time during which their fragrance is perceived.

[0063] Examples of fragrance modulators suitable for use according to the present disclosure include, but are not limited to, caprylyl alcohol, octanol, butyloctanol, isotridecyl alcohol, hexyldecanol, isostearyl alcohol, octyldecanol, octyldodecanol, decyltetradecanol, tetradecyloctadecanol, PPG-20 methyl glucose ether, methyl glucoside polyol; ethyl glucoside polyol; propyl glucoside polyol; isocetyl alcohol; PPG-3 myristyl ether; neopentyl glycol diethylhexanoate; sucrose laurate; sucrose dilaurate, sucrose myristate, sucrose palmitate, sucrose stearate, sucrose distearate, sucrose tristearate, hyaluronic acid disaccharide sodium salt, sodium hyaluronate, propylene glycol propyl ether; dicetyl ether; polyglycerin-4 ethers; isoceteth-5; isoceteth-7, isoceteth-10; isoceteth-12; isoceteth-15; isoceteth-20; isoceteth-25; isoceteth-30; disodium lauroamphodipropionate; hexaethylene glycol monododecyl ether; and their mixtures; neopentyl glycol di isononanoate; cetearyl ethyl hexanoate; panthenol ethyl ether, DL-panthenol, N-hexadecyl n-nonanoate, noctadecyl n-nonanoate, a profragrance, cyclodextrin, and any combination thereof.

[0064] The malodor counteracting compositions described herein may optionally comprise at least one perfumery adjuvant.

[0065] The perfumery adjuvant is an ingredient capable of imparting an additional added benefit such as a color, a particular light resistance, chemical stability, etc. A detailed description of the nature and type of adjuvant commonly used in perfuming compositions cannot be exhaustive, but mention is made that said ingredients are well known to a person skilled in the art.

[0066] Some examples of perfumery adjuvants include, but are not limited to, 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, insect repellants, ointments, vitamins and mixtures thereof.

[0067] In some embodiments, the malodor counteracting compositions of the present disclosure may further comprise at least one other malodor control (MOG) compound. As used herein, the term “other MOC compound” refers to a material which is already known to provide MOC activity, including odor coverage, OR antagonist activity, and / or odor sequestration activity, and is commonly used in the industry for such use. The at least one other MOC compound can be included to further boost, or complement, the MOC activity of the malodor counteracting compositions of the present disclosure.

[0068] Non-limiting examples of other MOC compounds include antimicrobial agents, malodor absorbers, chemical neutralizers, e.g., acid-base reagents, thiol traps, odor blockers, cross- adaptation agents, such as those disclosed in U.S. Patent No. 5,538,719, which is incorporated herein by reference, and malodor complexation agents, e.g., cyclodextrins.

[0069] Examples of antimicrobial agents include, but are not limited to, metal salts such as zinc citrate, zinc oxide, zinc pyrethiones, and octopirox; organic acids, such as sorbic acid, benzoic acid, and their salts; parabens, such as methyl paraben, propyl paraben, butyl paraben, ethyl paraben, isopropyl paraben, isobutyl paraben, benzyl paraben, and their salts; alcohols, such as benzyl alcohol, phenyl ethyl alcohol; boric acid; 2,4,4'-trichloro-2-hydroxy-diphenyl ether; phenolic compounds, such as phenol, 2-methyl phenol, 4-ethyl phenol; essential oils such as rosemary, thyme, lavender, eugenol, geranium, tea tree, clove, lemon grass, peppermint, or their active components such as anethole, thymol, eucalyptol, farnesol, menthol, limonene, methyl salicylate, salicylic acid, terpineol, nerolidol, geraniol, and mixtures thereof.

[0070] Examples of malodor absorbers include, but are not limited to, molecular sieves, such as zeolites, silicas, aluminosilcates, and cyclodextrins; and organic absorbents, such as, for example, activated charcoal, dried citrus pulp, cherry pit extract, corncob, and mixtures thereof.

[0071] In some embodiments, the malodor counteracting composition may further comprise a functional perfume accord. As used herein, the term “functional perfume accord” refers to a mixture of at least two perfuming ingredients which possess malodor counteracting properties. For example, the functional perfume accord may comprise a mixture of at least two perfuming ingredients that have been shown to counteract fecal malodor using a sensory panel.

[0072] Non-limiting examples of perfuming ingredients that may be included as functional perfume accords include ionones, irones, damascenes, damascenone, citral, methylcinnamic aldehyde, pelargodienal, orivone, or mixtures thereof.

[0073] The malodor counteracting compositions according to the present disclosure may be prepared according to any method known to those of ordinary skill in the art. The ordinarily skilled artisan is perfectly able to design optimal formulations for the desired effect by admixing the above-mentioned components to arrive at the desired composition by applying standard knowledge and concepts known to those of ordinary skill and by utilizing routine optimization methodologies.

[0074] The malodor counteracting composition described herein may comprise a solid carrier. The malodor counteracting composition described herein or elements of the 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. Suitable solid carriers include, but are not limited to, absorbing gums or polymers or inorganic materials, such as porous polymers, cyclodextrins, dextrins, maltodextrins, wood-based materials, organic or inorganic gels, clays, gypsum talc or zeolites. In some embodiments, the malodor counteracting compositions may be adsorbed or absorbed on a porous or non-porous substrate in loose powder or compacted form, the substrate being selected from cellulose (paper / cardboard), vermiculite, other industrial absorbents, perlite, calcium carbonate, pumice, wood, sawdust, ground corn cob, ground rice hull, rice hull ash, biochars, starches, modified starches, and mixtures thereof.

[0075] The malodor counteracting compositions according to the present disclosure may be combined with encapsulating materials such as polymers to form microcapsules or microparticles, or materials to form liquid delivery systems for the composition. Exemplary liquid delivery systems include, but are not limited to, emulsions, microemulsions, miniemulsions, gels, microgels, anhydrous gels, or dispersions.

[0076] In some embodiments, the malodor counteracting composition described herein or one or more elements of the composition, such as the compound of formula (I), may be encapsulated in at least one microcapsule, typically a plurality of microcapsules, generally in the form of a microcapsule slurry. In some embodiments, the at least one microcapsule is a core-shell microcapsule, which comprises a core surrounded by a shell. Generally, the malodor counteracting composition described herein or one or more elements of the composition is / are contained in the core. The shell of the microcapsule protects the compounds or compositions from the environment. The shell is generally made of a material that can release the compounds or compositions, typically upon breakage of the shell and / or by diffusion through the shell. Materials and processes for preparing such microcapsules are known to those of ordinary skill in the art.

[0077] The shell of the microcapsule may comprise a material selected from the group consisting of polyurea, polyurethane, polyamide, polyester, poly(meth)acrylate (i.e. polyacrylate and / or polymethacrylate), polysiloxane, polycarbonate, polysulfonamide, polymers of urea and formaldehyde, melamine and formaldehyde, melamine and urea, or melamine and glyoxal and mixtures thereof. The shell can also be hybrid, namely organic-inorganic, such as a hybrid shell composed of at least two types of inorganic particles that are cross-linked, or yet a shell resulting from the hydrolysis and condensation reaction of a polyalkoxysilane macro-monomeric composition.

[0078] In an embodiment, the shell of the microcapsules may be, each independently, selected from the group of aminoplast, polyamide, polyester, polyurea and polyurethane shells and mixtures thereof.

[0079] In another embodiment, the shell of the microcapsules may comprise an aminoplast copolymer, such as melamine-formaldehyde or urea-formaldehyde or cross-linked melamine formaldehyde or melamine glyoxal.

[0080] In yet another embodiment, the shell of the microcapsules may comprise polyurea, being made from, for example, but not limited to, isocyanate or isocyanate-based monomers and amine or amine-containing crosslinkers, such as guanidine carbonate and / or guanazole. Certain polyurea microcapsules comprise a polyurea wall which is the reaction product of the polymerization between at least one polyisocyanate comprising at least two isocyanate functional groups and at least one reactant selected from the group consisting of an amine (for example a water-soluble guanidine salt and guanidine); a colloidal stabilizer or emulsifier; and an encapsulated perfume. However, the use of an amine can be omitted.

[0081] The colloidal stabilizer includes an aqueous solution of between 0.1% and 0.4% of polyvinyl alcohol, between 0.6% and 1% of a cationic copolymer of vinylpyrrolidone and of a quaternized vinylimidazole (all percentages being defined by weight relative to the total weight of the colloidal stabilizer).

[0082] The emulsifier is an anionic or amphiphilic biopolymer. Exemplary emulsifiers include, but are not limited to, those selected from the group consisting of Gum Arabic, soy protein, gelatin, sodium caseinate, and mixtures thereof.

[0083] In an embodiment, the shell of the microcapsules may comprise polyurethane, being made from, for example, but not limited to, polyisocyanate and polyols, polyamide, polyester, and the like.

[0084] In another embodiment, the microcapsules may have a polymeric shell resulting from complex coacervation wherein the shell is possibly cross-linked.

[0085] The core-shell microcapsules may comprise an oil-based core comprising a hydrophobic active, and a composite shell comprising a first material and a second material, wherein the first material and the second material are different, and wherein the first material is a coacervate and the second material is a polymeric material. Generally, the weight ratio between the first material and the second material is comprised between 50:50 and 99.9:0.1.

[0086] The hydrophobic active, typically a perfume oil, comprises the malodor counteracting composition described herein or one or more elements of the composition, such as the compound of formula (I), as described herein.

[0087] The coacervate may comprise a first polyelectrolyte, typically selected from the group consisting of proteins (such as gelatin), polypeptides, and polysaccharides (such as chitosan), more typically gelatin; and a second polyelectrolyte, typically selected from the group consisting of alginate salts, cellulose derivatives, guar gum, pectinate salts, carrageenan, polyacrylic and methacrylic acid, xanthan gum, and plant gums, such as acacia gum (Gum Arabic), more typically Gum Arabic. The first coacervate material can be hardened chemically using a suitable cross-linker, such as glutaraldehyde, glyoxal, formaldehyde, tannic acid or genipin, or can be hardened enzymatically using an enzyme, such as transglutaminase.

[0088] The second material is a polymeric material, typically selected from the group consisting of polyurea, polyurethane, polyamide, polyester, polyacrylate, polysiloxane, polycarbonate, polysulfonamide, polymers of urea and formaldehyde, melamine and formaldehyde, melamine and urea, and melamine and glyoxal, and mixtures thereof, typically polyurea and / or polyurethane. The second material is present in an amount less than 3 wt.%, typically less than 1 wt.%, based on the total weight of the microcapsule slurry.

[0089] The microcapsule wall material may comprise any suitable resin, such as melamine, glyoxal, polyurea, polyurethane, polyamide, polyester, etc. Suitable resins include the reaction product of an aldehyde, typically formaldehyde or glyoxal, and an amine. Suitable amines include melamine, urea, benzoguanamine, glycoluril, and mixtures thereof. Suitable melamines include, but are not limited to, methylol melamine, methylated methylol melamine, imino melamine, and mixtures thereof. Suitable ureas include dimethylol urea, methylated dimethylol urea, urea-resorcinol, and mixtures thereof. Suitable materials for making may be obtained from one or more of the following companies Solutia Inc. (St Louis, Missouri U.S.A.), Cytec Industries (West Paterson, New Jersey U.S.A.), Sigma-Aldrich (St. Louis, Missouri U.S.A.). An exemplary core-shell microcapsule may comprise: an oil-based core comprising a hydrophobic active, optionally an inner shell made of a polymerized polyfunctional monomer; or a biopolymer shell comprising a protein, wherein at least one protein is cross-linked.

[0090] Suitable proteins include, but are not limited to, those selected from the group consisting of milk proteins, caseinate salts (such as sodium caseinate or calcium caseinate), casein, whey protein, hydrolyzed proteins, gelatins, gluten, pea protein, soy protein, silk protein, and mixtures thereof, typically sodium caseinate.

[0091] The protein may comprise sodium caseinate and a globular protein, typically selected from the group consisting of whey protein, beta-lactoglobulin, ovalbumine, bovine serum albumin, vegetable proteins, and mixtures thereof. An exemplary protein comprises a mixture of sodium caseinate and whey protein. An exemplary biopolymer shell comprises a crosslinked protein selected from the group consisting of sodium caseinate and / or whey protein. An exemplary microcapsule slurry may comprise at least one microcapsule made of: an oil-based core comprising a hydrophobic active; an inner shell made of a polymerized polyfunctional monomer; typically a polyisocyanate having at least two isocyanate functional groups; a biopolymer shell comprising a protein, wherein at least one protein is cross-linked; and wherein the protein contains typically a mixture comprising sodium caseinate and a globular protein, typically whey protein; and optionally at least an outer mineral layer.

[0092] In some cases, sodium caseinate and / or whey protein is (are) cross-linked protein(s). The weight ratio between sodium caseinate and whey protein is from 0.01 to 100, typically from 0.1 to 10, more typically from 0.2 to 5.

[0093] Another exemplary core-shell microcapsule is a polyamide core-shell microcapsule comprising: an oil-based core comprising a hydrophobic active, and a polyamide shell comprising or being obtained from: an acyl chloride, a first amino compound, and a second amino compound.

[0094] The polyamide core-shell microcapsule may comprise: an oil-based core comprising a hydrophobic active, and a polyamide shell comprising or being obtained from: an acyl chloride, typically in an amount of from 5 to 98%, more typically from 20 to 98%, most typically from 30 and 85% w / w; a first amino compound, typically in an amount of from 1% to 50% w / w, more typically from 7 to 40% w / w; a second amino compound, typically in an amount of from 1% to 50% w / w, more typically from 2 to 25% w / w; and a stabilizer, typically a biopolymer, typically in an amount of from 0 to 90%, more typically from 0.1 to 75%, most typically from 1 to 70% w / w.

[0095] Another exemplary polyamide core-shell microcapsule comprises: an oil-based core comprising a hydrophobic active, and a polyamide shell comprising or being obtained from: an acyl chloride, a first amino-compound being an amino acid, typically selected from the group consisting of L-Lysine, L-Arginine, L-Histidine, L-Tryptophane, and any mixture thereof; a second amino-compound, typically selected from the group consisting of ethylene diamine, diethylene triamine, cystamine, and any mixture thereof; and a biopolymer selected from the group consisting of casein, sodium caseinate, bovin serum albumin, whey protein, and any mixture thereof.

[0096] The first amino-compound can be different from the second amino-compound.

[0097] The preparation of core-shell microcapsules, typically as an aqueous dispersion / slurry, are made according to methods and processes well known by those of ordinary skill in the art.

[0098] For example, in one such method, the microcapsule is a one-shell aminoplast core-shell microcapsule obtained by a process comprising the steps of:

[0099] 1) admixing a perfume oil with at least a polyisocyanate having at least two isocyanate functional groups to form an oil phase;

[0100] 2) dispersing or dissolving into water an aminoplast resin and, optionally, a stabilizer to form a water phase;

[0101] 3) preparing an oil-in-water dispersion, wherein the mean droplet size is comprised between 1 and 100 microns, by admixing the oil phase and the water phase;

[0102] 4) performing a curing step to form the wall of said microcapsule; and

[0103] 5) optionally drying the final dispersion to obtain the dried core-shell microcapsule. In another exemplary method, the microcapsule is an aminoplast formaldehyde-free microcapsule slurry prepared by a process comprising the steps of 1) preparing an oligomeric composition comprising the reaction product of, or obtained by reacting together: a. a polyamine component in the form of melamine or of a mixture of melamine and at least one C1-C4 compound comprising two NH2 functional groups; b. an aldehyde component in the form of a mixture of glyoxal, a C4-6 2,2-dialkoxy- ethanal and optionally a glyoxalate, said mixture having a molar ratio glyoxal / C4-6 2,2-dialkoxy-ethanal comprised between 1 / 1 and10 / 1 ; and c. a protic acid catalyst;

[0104] 2) preparing an oil-in-water dispersion, wherein the droplet size is comprised between 1 and 600 microns, and comprising: a. an oil; b. a water medium; c. at least an oligomeric composition as obtained in step 1 ; d. at least a cross-linker selected amongst: i. C4-C12 aromatic or aliphatic di- or tri-isocyanates and their biurets, triurets, trimmers, trimethylol propane-adduct and mixtures thereof; and / or ii. a di- or tri-oxiran compound of formula:

[0105] Q-(oxiran-2-ylrnethyl)m wherein m is 2 or 3 and Q represents a C2-C6 group optionally comprising from 2 to 6 nitrogen and / or oxygen atoms; e. optionally a C1-C4 compounds comprising two NH2 functional groups;

[0106] 3) heating the dispersion; and

[0107] 4) cooling the dispersion.

[0108] Further related examples are described in greater detail in PCT Publication No.

[0109] WO 2013 / 068255.

[0110] In another exemplary method, the microcapsule is a polyamide-based microcapsule prepared by a process comprising the following steps: a) dissolving at least one acyl chloride in a hydrophobic material, typically a perfume to form an oil phase; b) dispersing the oil phase obtained in step a) into a water phase comprising a first amino compound to form an oil-in water emulsion; c) performing a curing step to form polyamide microcapsules in the form of a slurry; wherein a stabilizer is added in the oil phase and / or in the water phase, and wherein at least a second amino-compound is added in the water phase before the formation of the oil-in-water emulsion and / or in the oil-in-water emulsion obtained after step b). Examples of processes for the preparation of polyurea and polyureathane-based microcapsule slurries are, for instance, described in WO 2007 / 004166, EP 2300146, and EP 2579976. An exemplary process for the preparation of polyurea or polyurethane-based microcapsule slurries comprises the following steps: a) dissolving at least one polyisocyanate having at least two isocyanate groups in an oil to form an oil phase; b) preparing an aqueous solution of an emulsifier or colloidal stabilizer to form a water phase; c) adding the oil phase to the water phase to form an oil-in-water dispersion, wherein the mean droplet size is comprised between 1 and 500 pm, preferably between 5 and 50 pm; and d) applying conditions sufficient to induce interfacial polymerization and form microcapsules in form of a slurry.

[0111] The microcapsules may be in the form of a powder, which in particular may be obtained by submitting the microcapsule slurry to a drying step, like spray-drying. Slurries may be spray- dried, typically in the presence of a polymeric carrier material, such as polyvinyl acetate, polyvinyl alcohol, dextrins, natural or modified starch, gum Arabic, vegetable gums, pectins, xanthans, alginates, carrageenans or cellulose derivatives to provide microcapsules in a powder form. It is understood that any standard method known to those of ordinary skill in the art to perform such drying is also applicable.

[0112] For example, other drying methods such as extrusion, plating, spray granulation or fluidized bed processes, or even drying at room temperature using materials (carrier, desiccant) that meet specific criteria, as disclosed in WO 2017 / 134179, may be used. The core-shell microcapsule(s) can also be obtained by using different or more than one encapsulation method.

[0113] For the sake of clarity, it is also understood that any mixture resulting directly from a chemical synthesis, e.g. a reaction medium without an adequate purification, in which a compound of Formula (I) would be involved as a starting, intermediate or end-product could not be considered as a malodor counteracting composition according to the present disclosure as far as the mixture does not provide the compound of Formula (I) in a suitable form. Thus, unpurified reaction mixtures are generally excluded from the present disclosure unless otherwise specified.

[0114] Consumer Products

[0115] In certain aspects, the present disclosure relates to a consumer product comprising the malodor counteracting composition described herein. Non-limiting examples of consumer products according to the present disclosure include, but are not limited to:

[0116] • a perfume, such as a fine perfume, an Eau de Toilette, a cologne or an aftershave lotion or solution;

[0117] • a hair care product, such as a shampoo, a hair conditioner, a hair cream, a hair oil, a hair styling product (such as a spray, mousse or gel), a hair coloration product or a hair permanent wave product;

[0118] • a skin care product, such as a face cream, a face lotion, a shaving product (such as a foam, cream, gel or oil), a body and / or hand product (such as a lotion, cream, gel or oil), a skin firming product, a depilatory, a talcum powder, a foot care cream or lotion, baby wipes, cleansing wipes, moisturizer wipes, a sunprotection product (such as a spray, lotion, cream or oil), an after-sun lotion, or a self-tanning product;

[0119] • a fabric care product, such as a liquid detergent, a powder detergent, detergent tablets, a detergent bar, a detergent paste, a detergent pouch, a liquid fabric softener, fabric softener sheets, a fabric scent booster, a laundry pre-treatment, a fabric refresher, an ironing water, a laundry bleach, a carpet powder or a carpet cleaner;

[0120] • a body deodorant or antiperspirant product;

[0121] • a skin-cleansing product, such as a soap bar, a shower gel, a liquid hand soap, a bath foam or an intimate wash product;

[0122] • an air freshening product, such as an air freshener spray, a gel air freshener, a liquid-wick air freshener, a solid air freshener comprising a porous substrate (such as a paper or card blotter, a porous ceramic, or a porous plastic), a scented candle, a liquid or gel air freshener comprising a permeable membrane, an electrically operated air freshener, and a dual-purpose air freshener / disinfectant spray; and

[0123] • a surface care product, such as an all-purpose cleaner, a furniture polish, a wood floor cleaner, a window cleaner, a hand dishwashing product (such as a liquid, gel or paste), a machine dishwashing product (such as a powder, liquid, gel, tablet or sachet), a toilet bowl cleaning liquid, an in-cistern toilet cleaner, a toilet rim block, or a toilet rim liquid; a pet-litter.

[0124] In some embodiments, consumer product comprises from 0.1% to 85% by weight of the malodor counteracting composition, relative to the total weight of the consumer product. In some embodiments, the consumer product comprises from 0.1% to 15%, typically 0.1% to 7%, more typically 0.1% to 5%, by weight of the malodor counteracting composition, relative to the total weight of the consumer product. In some embodiments, the consumer product comprises from 0.1% to 2%, typically 0.1% to 0.5%, more typically 0.1% to 0.3%, by weight of the malodor counteracting composition, relative to the total weight of the consumer product.

[0125] In some embodiments, the consumer product comprises from 0.5% to 15%, typically 0.5% to 7%, more typically 0.5% to 5%, by weight of the malodor counteracting composition, relative to the total weight of the consumer product. In some embodiments, the consumer product comprises from 0.5% to 2% by weight of the malodor counteracting composition, relative to the total weight of the consumer product.

[0126] In some embodiments, the consumer product comprises from 30% to 85%, typically 30% to 70%, more typically 30% to 60%, by weight of the malodor counteracting composition, relative to the total weight of the consumer product. In some embodiments, the consumer product comprises from 40% to 85%, typically 40% to 70%, more typically 40% to 60%, by weight of the malodor counteracting composition, relative to the total weight of the consumer product.

[0127] Mention is made of the use of a compound of formula (I) for reducing, preventing, or inhibiting a subject’s perception of malodor. The elements and features of the compound of formula (I) as described herein are applied mutatis mutandis to the use of the compound of formula (I) for reducing, preventing, or inhibiting a subject’s perception of malodor.

[0128] EXAMPLES

[0129] To further illustrate this invention, the following examples are included. The examples should not, of course, be construed as specifically limiting the invention. Variations of these examples within the scope of the claims are within the purview of one skilled in the art and are considered to fall within the scope of the invention as described and claimed herein. The reader will recognize that the skilled artisan, armed with the present disclosure, and skill in the art is able to prepare and use the invention without exhaustive examples.

[0130] Odorant receptor activity was characterized in a cell-based assay using a standard cell line, as illustrated in PCT Publication No. WO 2016 / 201153, wherein endogenous RTP1 gene was activated for increase chaperone protein expression. Cells were seeded at a density of 7500 cells / well in 96-well white, opaque bottom plates (Corning, Cat # 3688) in DMEM supplemented with 10% FBS without antibiotic and incubated at 37 C in 5% CO2 overnight. Cells were co-transfected with a Lucy-Flag-Rho tagged version of each odorant receptor along with the canonical human olfactory human G-protein alpha subunit G-olf, and subsequently activated by their respective ligands.

[0131] For dose-response experiments, compounds were diluted in assay buffer (1X HBSS, 20 mM HEPES, 0.5 M IBMX) to 10 different concentrations between 10'8and 10'3M at approximately half-log intervals (final concentration in 0.2% dimethyl sulfoxide vehicle). Cells were treated for 30 minutes at 37C in 5% CO2 with compounds prepared as described above (for agonist) or in addition added to a binary mixture with the respective ECso (for antagonist). The ECso of each activator-OR pair was determined in a triplicate dose response agonist experiment to set the concentration to reach 80% activation level. OR activity was monitored using the HTRF (Homogeneous Time-Resolved Fluorescence) cAMP dynamic 2 kit (Revvity, Cat # 62AM4PEB), a competitive immunoassay between native cAMP produced by cells and the cAMP tracer molecule, labelled with proprietary Revvity fluorophore D2. CAMP-D2 bound to the cryptate-labelled anti-cAMP mouse generates fluorescence via a FRET signal. Due to the competition-based nature of the HTRF assay, a decreasing HTRF ratio indicates cAMP accumulation and a corresponding increase activity.

[0132] Example 1 - Inhibitory Effects of Cyclopentanones

[0133] Using a standard cell line described above, the inhibition activity across different ingredients were compared based on IC50 potency and percent inhibition. The different ingredients tested are summarized in Table 1 below.

[0134] Table 1

[0135] Inhibitors were diluted in 0.2% DMSO and evaluated at 10 different concentrations (ranging from 10'8M to 10'3M at approximately half-log intervals) against either OR11A1 activated at 80% by Geosmin or OR52A5 activated at 80% by Isononanoic acid. From the binary mixture, the % inhibition was determined from the reduction in the total assay window (the difference from the 80% activation to the baseline vehicle control) caused by highest dose of the respective inhibitor. The IC50, concentration of the inhibitor where 50% of the percent inhibition is reached, were calculated for each compound tested.

[0136] Ingredients A-C were compared by quantifying each ingredient’s percent inhibition (the % reduction of the full ECso window) and the ICso (concentration where it inhibits 50% of this window) from the binary mixtures with each respective OR. As shown in FIG. 1 , Ingredient A inhibits Geosmin activation of OR11A1 at a higher percentage than Ingredient B or C. As shown in FIG. 2, for OR52A5 activation by Isononanoic acid, Ingredient A has a higher percent inhibition when compared to Ingredient B and C.

[0137] Example 2 - Dose-dependent studies against OR11A1 and OR52A5

[0138] Dose-dependent studies of ingredient A (2-(5-hexen-1-yl)cyclopentanone) were conducted according to the procedure described hereinabove. The molecular receptive range of human odorant receptor OR11A1 was previously characterized (see W02021 / 064201A1), where Geosmin (CAS # 19700-21-1) was identified as a strong activator. For OR52A5, this odorant receptor is activated by Isononanoic acid (CAS # 54947-74-9). Odorant receptors activity is monitored by changes in the levels of cAMP using a competition based HTRF (Homogeneous Time-Resolved Fluorescence) assay, where loss of HTRF Ratio (Y axis) reflects an increase in cAMP production as a result of OR activity.

[0139] As shown in FIG. 3, odorant receptor OR11A1 was activated by Geosmin in a dose dependent manner (open circles). In the binary mixture, where odorant receptor OR11 A1 was activated at 80% levels by Geosmin, Ingredient A reduced the levels of cAMP production in a dose dependent manner (solid circles). The vehicle control sets the baseline of cAMP in resting cells (stars).

[0140] Similarly, as shown in FIG. 4, odorant receptor OR52A5 was activated by Isononanoic acid in a dose dependent manner (open circles). In the binary mixture, where odorant receptor OR52A5 was activated at 80% levels by Isononanoic acid, Ingredient A reduced the levels of cAMP production in a dose dependent manner (solid circles). The vehicle control sets the baseline of cAMP in resting cells (stars).

[0141] Example 3 - Impact on Perceived Intensity of Geosmin and on Odor Hedonics

[0142] To measure the impact of 2-(5-hexen-1-yl)cyclopentanone on the perceived intensity of geosmin, samples containing only geosmin diluted in dipropylene glycol (DiPG) at a 0.003% concentration, as well as samples containing a mixture of geosmin (at the same 0.003% concentration) and an antagonist (i.e. , 2-(5-hexen-1-yl)cyclopentanone) diluted in DiPG at a 0.01% concentration, were evaluated by 33 individuals (henceforth, “participants”). At these concentrations, 2-(5-hexen-1-yl)cyclopentanone and geosmin are perceived to be iso-intense. Each sample contained two cellulose pads in a 16 oz glass jar equipped with a flip-top plastic lid. In jars containing only a geosmin dilution, the dilution was pipetted onto one pad and DiPG was pipetted onto the other pad; in jars containing odorant mixtures, 2-(5-hexen- 1-yl)cyclopentanone and geosmin dilutions were pipetted onto two separate pads. Because the pads were placed into separate paper dishes inside the jar, the dilutions could not come in contact with one another. Before starting evaluations, each participant took a few sniffs from a jar with a geosmin dilution (reference sample) to familiarize themselves with the geosmin odor. Except for the reference sample, all samples were blind-coded.

[0143] To evaluate a sample, a participant would open the jar lid, take a few sniffs from the jar, close the lid, and rate overall odor intensity and geosmin intensity of the sample. The two ratings were made on 0 to 10 linear scales, where 0 and 10 were labelled “None” and “Very strong,” respectively. To ensure headspace equilibration, the jars were prepared well in advance of sensory evaluations. The presentation of samples was randomized among participants, with a one-minute interstimulus interval.

[0144] The ratio of geosmin intensity to overall intensity was computed for each type of sample (e.g., mixture of 2-(5-hexen-1-yl)cyclopentanone and geosmin), separately for each participant; next, the ratio was averaged across participants. Pleasantness ratings were averaged across participants for each type of sample.

[0145] FIG. 5 shows the impact of Ingredient A on the perceived intensity of geosmin. The bars labelled with different letters (e.g., A and B above bars) are significantly different (p < .05, one-tailed). As shown in FIG. 5, participants perceived, on average, that when mixed with 2-(5- hexen-1-yl)cyclopentanone in the headspace, geosmin contributes significantly less to overall scent intensity of the mixture relative to when geosmin is presented alone.

[0146] The impact of 2-(5-hexen-1-yl)cyclopentanone on odor hedonics was also evaluated separately by 26 participants. The same procedure as for the evaluations of geosmin intensity was used, except that participants rated odor pleasantness on a -5 to 5 bipolar scale, where -5 and 5 were labelled “Very unpleasant” and “Very pleasant,” respectively.

[0147] As shown in FIG. 6, the mixture of 2-(5-hexen-1-yl)cyclopentanone and geosmin was perceived, on average, to be significantly more pleasant than geosmin alone. The bars labelled with different letters (e.g., A and B above bars) are significantly different (p < .05, one-tailed).

[0148] Example 4 - Impact on the Perceived Intensity of Isononanoic Acid

[0149] The impact of 2-(5-hexen-1-yl)cyclopentanone on the perceived intensity of isononanoic acid was evaluated by 44 participants, using the same procedure as for the evaluations of geosmin intensity as described in Example 3. Each glass jar contained either isononanoic acid diluted in Di PG at a 0.4% concentration or a mixture of isononanoic acid at the same concentration and an iso-intense antagonist (i.e., 0.01% dilution of 2-(5-hexen- 1-yl)cyclopentanone in DiPG).

[0150] To quantify the contribution of scent of isononanoic acid to overall scent intensity, the same procedure described in Example 3 was followed. As shown in FIG. 7, participants perceived, on average, that when mixed with 2-(5-hexen-1-yl)cyclopentanone in the headspace, isononanoic acid contributes significantly less to overall scent intensity of the mixture relative to when isononanoic acid is presented alone.

[0151] The disclosed subject matter has been described with reference to specific details of particular embodiments thereof. It is not intended that such details be regarded as limitations upon the scope of the disclosed subject matter except insofar as and to the extent that they are included in the accompanying claims.

[0152] Therefore, the exemplary embodiments described herein are well adapted to attain the ends and advantages mentioned as well as those that are inherent therein. The particular embodiments disclosed above are illustrative only, as the exemplary embodiments described herein may be modified and practiced in different but equivalent manners apparent to those of ordinary skill in the art having the benefit of the teachings herein. Furthermore, no limitations are intended to the details of construction or design herein shown, other than as described in the claims below. It is therefore evident that the particular illustrative embodiments disclosed above may be altered, combined, or modified and all such variations are considered within the scope and spirit of the exemplary embodiments described herein. The exemplary embodiments described herein illustratively disclosed herein suitably may be practiced in the absence of any element that is not specifically disclosed herein and / or any optional element disclosed herein.

Claims

CLAIMS1. Use of a malodor antagonizing compound to reduce a perception of a malodor by a human subject, wherein the malodor antagonizing compound is a compound of formula (I)in the form of any one of its stereoisomers or a mixture thereof, wherein n is 1 or 2, and the bond a is present or absent.

2. The use of claim 1, which comprises introducing the malodor antagonizing compound to a closed space or a surface, wherein the closed area or the surface comprise one or more malodor agents.

3. The use of claim 2, wherein the malodor antagonizing compound is introduced as a component of a liquid composition at a concentration ranging from 10 ppm to 100 ppm by weight, based on the total weight of the liquid composition.

4. The use of any one of claims 1 to 3, wherein the malodor antagonizing compound is introduced at a concentration sufficient to antagonize a binding of the one or more malodor agents to a human OR11A1 receptor or a human OR52A5 receptor.

5. The use of any one of claims 1 to 4, wherein the malodor comprises a latrine malodor, a laundry malodor, or a sweat malodor.

6. A method of reducing a perception of a malodor by a human subject, the method comprising introducing a malodor antagonizing compound to a closed space or a surface, wherein the closed space or the surface comprise one or more malodor agents, and wherein the malodor antagonizing compound is a compound of formula (I)in the form of any one of its stereoisomers or a mixture thereof, wherein n is 1 or 2, and the bond a is present or absent.

7. The method of claim 6, wherein the malodor antagonizing compound is introduced as a component of a liquid composition at a concentration ranging from 10 ppm to 100 ppm by weight, based on the total weight of the liquid composition.

8. The method of claim 6 or 7, wherein the malodor antagonizing compound is introduced at a concentration sufficient to antagonize a binding of the one or more malodor agents to a human OR11A1 receptor or a human OR52A5 receptor.

9. The method of any one of claims 6 to 8, wherein the malodor comprises a latrine malodor, a laundry malodor, or a sweat malodor.

10. A malodor counteracting composition, the composition comprising carrier and a malodor antagonizing compound, which is a compound of formula (I)in the form of any one of its stereoisomers or a mixture thereof, wherein n represents 1 or 2, and bond a is present or absent.

11. The malodor counteracting composition of claim 10, wherein the malodor antagonizing compound is present in the composition at a concentration ranging from 0.0001% by weight to 99.9% by weight, based on the total weight of the malodor counteracting composition.

12. The malodor counteracting composition of claim 10 or 11, further comprising one or more functional perfumes, such as compounds selected from the group consisting of ionones, irones, damascenes, damascenone, citral, methylcinnamic aldehyde, pelargodienal, orivone, and mixtures thereof.

13. A consumer product comprising the malodor counteracting composition of any one of claims 10 to 12.

14. The consumer product of claim 13, wherein the consumer product is a perfume, a hair care product, a skin care product, a fabric care product, a body deodorant or antiperspirant product, a skin-cleansing product, an air freshening product, or a surface care product.

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