Trans-2-nonenal odor suppressant

Abstract

To provide a novel trans-2-nonenal odor inhibitor or the like.SOLUTION: The present invention provides a trans-2-nonenal odor inhibitor or the like, containing at least one or two kinds selected from a group consisting of anethole, menthol, α-isomethyl ionone, α-damascone, 3-methyl-5-phenyl-1-pentanol, strawberry aldehyde, linalool, dodecanal, cis-jasmone, nerol, methyl butyrate, 1-(2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydronaphthalene-2-yl)ethane-1-one, terpineol, floropal, β-ionone, styralyl acetate and fenchol as an active ingredient.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a trans-2-nonenal odor suppressant containing a specific fragrance as an active ingredient. [Background technology]

[0002] Our living environment contains a large number of malodorous molecules with different polarities and molecular weights. To eliminate these diverse malodorous molecules, various deodorizing methods have been developed. Generally, deodorizing methods are broadly divided into biological, chemical, physical, and sensory methods. Among the malodorous molecules, unsaturated aldehydes, including trans-2-nonenal, can be deodorized through chemical reactions.

[0003] However, these malodorous substances often have a low threshold, making it difficult to deodorize them to a concentration that cannot be detected by chemical deodorization methods alone, and therefore sensory deodorization is often used in combination to effectively deodorize them.Sensory deodorization mainly includes (1) a method using a fragrance in excess of the malodor, known as masking deodorization, (2) a method using a fragrance with strong characteristics different from the malodor, known as pairing deodorization, (3) a method of deodorizing by using a fragrance that responds to the olfactory receptors to which malodors respond, causing adaptation, (4) a method of deodorizing by suppressing the response of the olfactory receptors to which malodors respond, and (5) a method of deodorizing by modulating or blocking signals from olfactory cells.

[0004] Trans-2-nonenal is a naturally occurring unsaturated aldehyde and one of the substances that cause body odor due to sweat and sebum, and has a low threshold. Several substances have been disclosed as chemical deodorizers for trans-2-nonenal.For example, Patent Document 1 lists the following as ingredients that have an excellent effect of masking body odor such as nonenal: almoaz oil, virsil oil, galbanum oil, geranium oil, spearmint oil, ylang-ylang oil, cardamom oil, elemi oil, lavender oil, peppermint oil, nutmeg oil, chamomile oil, eucalyptus oil, rosemary oil, allyl amyl glycolate, 1,1-dimethoxy-2-phenylethane, 2,4-dimethyl-4-phenyltetrahydrofuran, dimethyltetrahydrobenzaldehyde, 2,6-dimethyl-7-octen-2-ol, 1,2-diethoxy-3,7-dimethyl-2,6-octadiene, phenylacetaldehyde, rose oxide, and ethyl-2- Methyl pentanoate is an ingredient with excellent harmonization effects, such as lavandin oil, lemon oil, lime oil, orange oil, petitgrain oil, bergamot oil, clary sage oil, coriander oil, cypress oil, jasmine absolute, rose oil, rose absolute, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1yl)-2-buten-1-one, ethyl vanillin, a mixture of 2,6-dimethyl-2-octenol and 3,7-dimethyl-2-octenol, tert-butylcyclohexyl acetate, anisyl acetate, allyl cyclohexyloxyacetate, coumarin, ethyl acetoacetate, 4-phenyl-2,4,6-trimethyl-1,3-dioxane, ethyl acetoacetate ethylene glycol ketal, 4-methylene-3,5,6,6-tetramethyl-2- Heptanone, ethyl tetrahydrosaffranate, geranyl nitrile, cis-3-hexen-1-ol, cis-3-hexenyl acetate, cis-3-hexenyl methyl carbonate, 2,6-dimethyl-5-hepten-1-al, 4-(tricyclo[5,2,1,02,6]decylidene-8-butanal, 5-(2,2,3-trimethyl-3-cyclopentenyl)-3-methylpentan-2-ol, p-tert-butyl-α-methylhydrocinnamic aldehyde, ethyl[5,2,1,02,6]tricyclodecanecarboxylate, citronellol, and citral are disclosed.

[0005] Patent Document 2 discloses a deodorizer whose main ingredient is 1,4-cineole or 1,8-cineole, and Patent Document 3 discloses that a deodorizer containing a dihydric or trihydric C2-C6 alcohol such as 1,3-butylene glycol as an active ingredient has a deodorizing effect against nonenal. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] Japanese Patent Application Publication No. 11-286428 [Patent Document 2] Japanese Patent Application Laid-Open No. 2017-113354 [Patent Document 3] WO2012 / 108494 publication Summary of the Invention [Problem to be solved by the invention]

[0007] Therefore, an object of the present invention is to provide a novel trans-2-nonenal odor suppressant and the like. [Means for solving the problem]

[0008] The olfactory receptors that recognize odor molecules such as malodors are complex, and known fragrance ingredients do not necessarily suppress malodors such as the odor of trans-2-nonenal, and may even enhance the malodor. The present inventors discovered that specific fragrance ingredients suppress the odor of trans-2-nonenal, leading to the completion of the present invention.

[0009] That is, the present invention provides: Anethole, menthol, α-isomethylionone, α-damascone, 3-methyl-5-phenyl-1-pentanol, strawberry aldehyde, linalool, dodecanal, cis-jasmone, nerol, methyl butyrate, 1-(2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydronaphthalen-2-yl)ethan-1-one, terpineol, floropal, β-ionone, styrallyl acetate, and fenchol. The present invention provides a trans-2-nonenal odor suppressant containing one or more active ingredients selected from the group consisting of:

[0010] The present invention also provides a method for suppressing the odor of trans-2-nonenal, which comprises the step of contacting the trans-2-nonenal odor suppressor with trans-2-nonenal. [Effects of the Invention]

[0011] The trans-2-nonenal odor inhibitor provided by the present invention exhibits a trans-2-nonenal odor suppressing effect that is equal to or far superior to that of existing inhibitors. DETAILED DESCRIPTION OF THE INVENTION

[0012] The present invention uses one or more active ingredients selected from the group consisting of anethole, menthol, α-isomethylionone, α-damascone, 3-methyl-5-phenyl-1-pentanol, strawberry aldehyde, linalool, dodecanal, cis-jasmone, nerol, methyl butyrate, 1-(2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydronaphthalen-2-yl)ethan-1-one, terpineol, fluoropearl, β-ionone, styrallyl acetate, and fenchol.

[0013] Among the above compounds, anethole, menthol, α-isomethylionone, α-damascone, 3-methyl-5-phenyl-1-pentanol, strawberry aldehyde, linalool, dodecanal, cis-jasmone, nerol, methyl butyrate, and 1-(2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydronaphthalen-2-yl)ethan-1-one are preferred. Among these, α-damascone, 3-methyl-5-phenyl-1-pentanol, strawberry aldehyde, linalool, cis-jasmone, 1-(2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydronaphthalen-2-yl)ethan-1-one, and terpineol are more preferred due to their low fragrance strength. Of these compounds, α-damascone and linalool are more preferred.

[0014] Each compound may be used alone, or two or more may be used in combination, as long as the effect of suppressing the trans-2-nonenal odor is not impaired. Furthermore, these compounds may be used by adding other fragrance ingredients to prepare a blended fragrance. Such other fragrance ingredients are not particularly limited as long as they do not impair the effect of suppressing the trans-2-nonenal odor, and include, for example, animal fragrances such as musk, spirit cat's scent, and dragon's scent, abies oil, acorn oil, almond oil, angelica root oil, peper oil, bergamot oil, perch oil, bois rose oil, kayabuchi oil, gananga oil, capsicum oil, caraway oil, cardamom oil, cassia oil, celery oil, cinnamon oil, citronella oil, and cognac oil. Examples of fragrances include vegetable fragrances such as coriander oil, cumin oil, camphor oil, basil oil, estgolan oil, eucalyptus oil, fennel oil, garlic oil, ginger oil, grapefruit oil, hop oil, lemon oil, lemongrass oil, nutmeg oil, mandarin oil, peppermint oil, orange oil, sage oil, star anise oil, turpentine oil, rosemary oil, eucalyptus oil, anise oil, lavender oil, cumin oil, cinnamon oil, and hiba oil. In addition, artificial fragrances such as synthetic fragrances or extracted fragrances can also be used as fragrances. Examples of such fragrances include hydrocarbon fragrances such as pinene and limonene, alcohol fragrances such as geraniol, citronellol, ethyl linalool, borneol, benzyl alcohol, anise alcohol, and β-phenethyl alcohol, phenol fragrances such as eugenol, aldehyde fragrances such as n-butyl aldehyde, isobutyraldehyde, hexyl aldehyde, citral, citronellal, benzaldehyde, and cinnamic aldehyde, ketone fragrances such as carvone, menthone, camphor, acetophenone, and ionone, lactone fragrances such as γ-butyrolactone, coumarin, and cineole, and ester fragrances such as octyl acetate, benzyl acetate, cinnamyl acetate, butyl propionate, and methyl benzoate.

[0015] The trans-2-nonenal odor inhibitor can be used to eliminate or neutralize the trans-2-nonenal odor contained in sweat, body odor, etc. The trans-2-nonenal odor inhibitor can be applied directly to the source of the trans-2-nonenal odor.

[0016] The trans-2-nonenal odor inhibitor is expected to be incorporated into various deodorants, various air fresheners, body or facial cleansers, laundry detergents, laundry softeners, cosmetics, and fragrance products. The trans-2-nonenal odor inhibitor is incorporated in a volatilizable form, including, but not limited to, a liquid agent, a sheet-like material supported on a carrier such as fiber, a gel agent, and the like.

[0017] Examples include oil-type deodorizing agents in which a trans-2-nonenal odor suppressant or a blended fragrance prepared by compounding the same is used as is or mixed with a suitable volatile organic solvent and then vaporized using a volatile medium; water-based deodorizing agents in which a trans-2-nonenal odor suppressant or a blended fragrance prepared by compounding the same is solubilized in water using a surfactant or the like and then vaporized using a volatile medium; gel-type deodorizing agents prepared by gelling the above using a gelling agent; and deodorizing agents in which the above is absorbed into a highly water-absorbent resin.

[0018] The volatile organic solvent is not particularly limited, but examples thereof include volatile alcohols and volatile glycol ethers. Among these, volatile alcohols include lower alcohols such as methanol, ethanol, 1-propanol, and 2-propanol. Furthermore, volatile glycol ethers include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol dimethyl ether, propylene glycol monomethyl ether, ethylene glycol monoisopropyl ether, diethylene glycol monomethyl ether, triethylene glycol monomethyl ether, propylene glycol monoethyl ether, dipropylene glycol monomethyl ether, tripropylene glycol monomethyl ether, butylene glycol monomethyl ether, 3-methoxy-1-butanol, and 3-methoxy-3-methyl-1-butanol.

[0019] The surfactant may be a nonionic surfactant, anionic surfactant, cationic surfactant, or amphoteric surfactant, either singly or in combination. The nonionic surfactant is not particularly limited, but examples thereof include polyoxyethylene alkyl ethers, polyoxyalkylene alkyl ethers, polyoxyethylene hydrogenated castor oil ethers, polyoxyethylene fatty acid esters, polyoxyethylene alkylphenyl ethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, sucrose fatty acid esters, glycerin fatty acid esters, polyoxyethylene polyoxypropylene block polymers, polyoxyethylene alkylamine ethers, fatty acid alkanolamides, tertiary amine oxides, etc. The polyoxyethylene alkyl ethers have a polyoxyethylene chain length of 3 to 18, preferably 7 to 12, and the alkyl chain may be either linear or branched, with an alkyl chain length of 8 to 22, preferably 12 to 14. Examples of the fatty acid alkanolamide include monoethanolamide and diethanolamide of coconut oil fatty acid, stearic acid, and lauric acid, and examples of the tertiary amine oxide include lauryl dimethylamine oxide, coconut oil fatty acid dimethylamine oxide, lauroylaminopropyl dimethylamine oxide, octyl dimethylamine oxide, and myristyl dimethylamine oxide.

[0020] Examples of anionic surfactants that can be used include higher fatty acid soaps, soap bases, metal soaps, N-acyl-L-glutamic acid triethanolamine, N-acyl-L-glutamic acid sodium, sodium alkyl sulfate, sodium alkyl sulfonate, polyoxyethylene alkyl ether sodium sulfate, polyoxyethylene alkyl ether phosphate, polyoxyethylene alkyl phenyl ether phosphate, coconut oil fatty acid methyl taurate sodium (N-cocoyl-N-methyl taurate sodium), triethanolamine lauryl sulfate, sodium lauryl sulfate, sodium lauroyl sarcosine, lauroyl methyl β-alanine sodium solution, and lauroyl methyl taurate sodium, and mixtures of two or more thereof can be used.

[0021] As the cationic surfactant, lanolin ethyl sulfate fatty acid aminopropylethyldimethylammonium, alkyltrimethylammonium chloride, dialkyldimethylammonium chloride, distearyldimethylammonium chloride, stearyldimethylbenzylammonium chloride, stearyltrimethylammonium chloride, benzalkonium chloride, benzethonium chloride, and the like can be used alone or in combination of two or more.

[0022] As the amphoteric surfactant, 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine, alkyldiaminoethylglycine hydrochloride solution, lauryldimethylaminoacetic acid betaine, and the like can be used alone or in combination of two or more thereof.

[0023] Examples of gelling agents include conventionally known ones such as carrageenan, gellan gum, agar, gelatin, guar gum, pectin, locust bean gum, xanthan gum, tamarind gum, sodium alginate, isobutylene-maleic anhydride copolymer, and cellulose derivatives such as carboxymethyl cellulose.

[0024] The water-absorbing resin is not particularly limited, but examples thereof include those containing polyacrylic acid or a salt thereof, such as a crosslinked polyacrylate, partially neutralized polyacrylate, a crosslinked acrylic acid and / or a salt thereof-acrylamide copolymer, a crosslinked isobutylene-maleic anhydride copolymer, a hydrolyzate of a starch-acrylonitrile graft copolymer, a (partially) neutralized starch-acrylate copolymer, a saponified product and a partially saponified product of a vinyl acetate-acrylate copolymer, a hydrolyzate of an acrylonitrile copolymer or an acrylamide copolymer, and a modified polyvinyl alcohol.

[0025] The trans-2-nonenal odor suppressant may contain, depending on its intended purpose, other components having a deodorizing effect, or any components used in deodorants or deodorizers, as long as they do not impair the effect of the active ingredient. Examples of such other components having a deodorizing effect include any known deodorants, such as deodorizing active ingredients extracted from various parts of plants, such as leaves, petioles, fruits, stems, roots, and bark (e.g., green tea extract); organic acids such as lactic acid, gluconic acid, succinic acid, glutaric acid, adipic acid, malic acid, tartaric acid, maleic acid, fumaric acid, itaconic acid, citric acid, benzoic acid, and salicylic acid; various amino acids and their salts; glyoxal; oxidizing agents; flavonoids; catechins; polyphenols; porous substances such as activated carbon and zeolites; inclusion agents such as cyclodextrins; photocatalysts; and various masking agents.

[0026] Examples of optional ingredients used in deodorants and anti-odor agents include fragrances, powdered ingredients, liquid oils and fats, solid oils and fats, waxes, hydrocarbons, plant extracts, herbal ingredients, higher alcohols, lower alcohols, esters, long-chain fatty acids, surfactants (nonionic surfactants, anionic surfactants, cationic surfactants, amphoteric surfactants, etc.), sterols, polyhydric alcohols, moisturizers, water-soluble polymer compounds, thickeners, film-forming agents, bactericides, preservatives, ultraviolet absorbers, fixatives, cooling agents, warming agents, irritants, sequestering agents, sugars, amino acids, organic amines, synthetic resin emulsions, pH adjusters, antioxidants, antioxidant aids, oils, powders, capsules, chelating agents, inorganic salts, organic salt pigments, thickeners, bactericides, preservatives, antifungal agents, colorants, antifoaming agents, extenders, modulators, organic acids, polymers, polymer dispersants, enzymes, and enzyme stabilizers.

[0027] In a second embodiment, a method for suppressing the odor of trans-2-nonenal is provided, comprising the step of contacting a trans-2-nonenal odor suppressor with trans-2-nonenal.

[0028] Examples of sources of trans-2-nonenal odor include body odor from humans and non-human animals, particularly around the neck. Therefore, clothing, bedding such as pillows, and indoor areas crowded with people (e.g., conference rooms, elevators, etc.) can also be sources of trans-2-nonenal odor. As used herein, the sources to which the trans-2-nonenal odor suppressant is directly applied do not include parts of the human body.

[0029] The contact can also be achieved by applying the trans-2-nonenal odor inhibitor to a source of trans-2-nonenal or the trans-2-nonenal odor. Application methods include sprinkling, spraying, and coating, and can be determined by those skilled in the art depending on the dosage form of the trans-2-nonenal odor inhibitor. Furthermore, this method may be combined with a known method for suppressing the trans-2-nonenal odor.

[0030] The timing of application is not particularly limited, and can be any time when the trans-2-nonenal odor is perceived. From a preventative standpoint, the trans-2-nonenal odor suppressant may be applied in advance to areas where the trans-2-nonenal odor is expected to be generated. [Example]

[0031] The present invention will be described in more detail below using examples, but the present invention is not limited to the following examples.

[0032] <Sensory test> (Test sample) The following test samples were used to test the deodorizing effect on the odor of trans-2-nonenal. [Table 1]

[0033] (Preparation of Masterbatch) Trans-2-nonenal was dissolved in dimethyl sulfoxide (DMSO) to prepare solutions (0.001 ppm, 0.01 ppm, 0.1 ppm, 1 ppm, 10 ppm, 100 ppm, 1000 ppm, 10000 ppm). Five grams of each solution was impregnated into pleated filter paper (185 mm diameter) and placed in a 500 ml beaker. The beaker was then sealed in a 10-liter bag, filled with odorless air, and left to stand at room temperature for 24 hours to prepare six masterbatch bags.

[0034] (Preparation of malodorous bags) The amounts of air shown in Table 2 were taken from the six types of masterbatch bags using a syringe and injected into 3-liter odor bags filled with odorless air to prepare odor bags 1 to 8. [Table 2]

[0035] (Preparation of scented bags) One gram of each of the fragrances listed in Table 1 was soaked in a pleated filter paper (90 mm diameter) and placed in a 500 ml beaker. The beaker was then sealed in a 10-liter bag, filled with odorless air, and left to stand at 25°C for 30 minutes to prepare a fragrance bag.

[0036] (Preparation of sample bags) Another set of the above malodor bags 1 to 8 was created, and 200 ml of air was taken from the above fragrance bag and injected into each of them, creating sample bags 1 to 8 in order.

[0037] (Fragrance pleasantness / unpleasantness, palatability) 200 ml of each fragrance bag was taken and filled with odorless air into a 3-liter bag. The pleasantness or unpleasantness and intensity of each fragrance were evaluated according to the following criteria. The values ​​shown are the average scores of four panelists who passed the olfactory test (T&T olfactometer method) in the Odor Judgement Examination and were confirmed to have normal sense of smell. The results are shown in Table 3.

[0038] (pleasantness / unpleasantness) -4: Extremely uncomfortable -3: Very uncomfortable -2: Unpleasant -1: Slightly uncomfortable 0: Neither pleasant nor unpleasant +1: Somewhat comfortable +2: pleasure +3: Very comfortable +4: Extremely comfortable

[0039] (strength) -3: Very weak -2: Weak -1: Slightly weak 0: Just right +1: Somewhat strong +2: Strong +3: Very strong

[0040] (Perception test of malodor caused by fragrance) Panelists were asked to smell the malodorous bags prepared above in order of increasing concentration, and those that could be determined to have the odor of trans-2-nonenal were marked with an ◯, and those that could not be determined to have the odor of trans-2-nonenal were marked with an ×. The number of the malodorous bag that could be recognized was taken as the threshold value of the odor of trans-2-nonenal.

[0041] Next, the panelists were asked to smell the sample bags containing the fragrance in the same order, starting with the malodor concentration. Those who could identify the odor as trans-2-nonenal were given a ◯, and those who could not were given an ×. The number of the malodor-recognized bag was taken as the odor threshold of trans-2-nonenal in the fragrance-mixed air. The value is the average of the four panelists. The results are shown in Table 3. If the threshold when the fragrance was added to a similar bag was higher than the concentration (threshold) perceived when smelling the malodor alone, it was determined that the fragrance contributed to deodorization (recognition of the malodor). Specifically, a score of 2 or more higher than the threshold for the malodor alone was given a ◎, a score of 1 or more higher was given a ◯, a score of less than 1 (0 or higher) was given a △, and a score of less than 0 was given an ×. The malodor-only bag was used as a control, and its odor suppression function was not evaluated.

[0042] [Table 3]

[0043] From the above results, it can be seen that all fragrances Nos. 1 to 17 make the odor of trans-2-nonenal less noticeable. In particular, fragrances Nos. 1 to 12, which had different threshold values, significantly reduced the odor of trans-2-nonenal. Furthermore, while high-intensity fragrances have limited applications, α-damascone, 3-methyl-5-phenyl-1-pentanol, strawberry aldehyde, linalool, cis-jasmone, 1-(2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydronaphthalen-2-yl)ethan-1-one, and terpineol, which have low intensity and high odor-suppressing effects, are particularly preferred trans-2-nonenal odor suppressants and are expected to be used in a variety of applications.

Claims

1. A trans-2-nonenal odor suppressant containing methyl butyrate and / or fenchol as active ingredients.

2. The trans-2-nonenal odor suppressant according to claim 1, further comprising, as an active ingredient, one or more selected from the group consisting of anethole, menthol, α-isomethylionone, α-damascone, strawberry aldehyde, linalool, dodecanal, cis-jasmone, nerol, 1-(2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydronaphthalen-2-yl)ethan-1-one, terpineol, fluoropearl, β-ionone, and styrallyl acetate.

3. The trans-2-nonenal odor suppressant according to claim 1 or 2, wherein the active ingredient is methyl butyrate.

4. A method for suppressing the odor of trans-2-nonenal, comprising a step of contacting the trans-2-nonenal odor suppressor according to any one of claims 1 to 3 with trans-2-nonenal.

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