JP2016187557A - Bad smell reducing agent - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a bad smell reducing agent based on olfactory receptor antagonism.SOLUTION: The invention provides a bad smell reducing agent containing, as an active ingredient, one or more antagonists, selected from the group consisting of 3-(3-isopropyl-phenyl)-butyraldehyde and 3-(4-tert-butylphenyl) propanal, against one of olfactory receptors selected from OR2W1, OR10A6, OR51E1, OR51I2, and OR51L1. The bad smell to be a target is nonanoic acid, hexanoic acid or isovaleric acid.SELECTED DRAWING: None

Description

  The present invention relates to a malodor control agent and a malodor control method.

  There are many malodorous molecules with different polarities and molecular weights in our living environment. Various deodorizing methods have been developed so far to deodorize various malodorous molecules. In general, deodorization methods are roughly classified into biological methods, chemical methods, physical methods, and sensory methods. Among the malodorous molecules, highly polar short chain fatty acids and amines can be deodorized by a chemical method, that is, neutralization reaction. In addition, sulfur compounds such as thiols can be deodorized by a physical method, that is, adsorption treatment. However, many malodorous molecules such as medium- and long-chain fatty acids and skatole remain that cannot be handled by the conventional deodorization method.

In mammals such as humans, the smell is bound to the olfactory receptor on the olfactory nerve cell located in the olfactory epithelium in the upper nasal cavity, and the response of the receptor is transmitted to the central nervous system. It is recognized by. In humans, it has been reported that there are 387 olfactory receptors, and the genes encoding them are about 3% of all human genes.
In general, olfactory receptors and odor molecules are associated with each other in a plurality of combinations. That is, each olfactory receptor receives a plurality of odor molecules with similar structures with different affinities, while each odorant receptor is received by a plurality of olfactory receptors. Furthermore, it has been reported that an odor molecule that activates one olfactory receptor acts as an antagonist that inhibits activation of another olfactory receptor. The combination of these multiple olfactory receptor responses has led to the recognition of individual odors.

  Therefore, even when the same odor molecule is present, if another odor molecule is present at the same time, the receptor response is inhibited by the other odor molecule, and the finally recognized odor may be completely different. This mechanism is called olfactory receptor antagonism. Unlike the deodorization method by adding another odor such as a perfume or a fragrance, the odor modulation by this receptor antagonism can specifically lose the recognition of a bad odor. In addition, there is no discomfort due to the smell of the fragrance.

  For nonanoic acid, hexanoic acid, isovaleric acid, etc., which are representative causative substances of body odor, conventionally, the odor has been the use of deodorants or deodorants, and the use of fragrances and fragrances (Patent Document 1 and Non-Patent Documents). It was deodorized and deodorized by means such as 1). However, these measures are methods that reduce the generation of odor substances in the first place or make another odor more strongly recognized, and are different from deodorization by masking based on olfactory receptor antagonism. Further, in the conventional method, when a deodorant is used, it takes time to reduce the odorous substance and thus lacks immediate effect. When using a fragrance, the odor of the fragrance itself may cause discomfort. Or in the conventional method, smells other than the target malodor may be erased. Deodorization by masking based on olfactory receptor antagonism may eliminate the above points.

  For olfactory receptor antagonism, it is necessary to search for and identify substances that exhibit an effective olfactory receptor antagonistic action against individual malodorous molecules, but such a search is not easy. Conventionally, odor evaluation has been performed by sensory tests by experts. However, the sensory test has problems such as the need to train experts who can evaluate odors and low throughput.

  For odor control by olfactory receptor antagonism, it is important to associate odors with olfactory receptors. Regarding olfactory receptors that accept nonanoic acid and hexanoic acid, OR2W1 responds to hexanoic acid and nonanoic acid, OR51E1 responds to nonanoic acid, and OR51L1 responds to hexanoic acid. It has been reported (Non-Patent Document 2). There is also a report that OR51E1 responds to isovaleric acid (Non-patent Document 3).

  Aldehyde perfume ingredients have been blended in human and environmental fragrances and deodorants, cleaning compositions, and the like (Patent Documents 1 to 3). However, these have been used as fragrance components and have not been used as antagonists that suppress the activity of olfactory receptors in response to malodor.

JP2003-190264 JP 2003-113392 A Special Table 2003-518162

Olfactory and odorous substances Michiaki Kawasaki, Tetsuro Horiuchi (Odor and Scent Environment Association) Saito H., Chi Q., Zhuang H., Matsunami H., Mainland J.D. Sci Signal., 2009, 2: ra9 Philippeau et al., ACHEMS 2009 Annual Meeting Abstract, 31st Annual Meeting of The Association for Chemoreception Sciences, # P121

  The present invention provides a malodor control method and a malodor control agent based on olfactory receptor antagonism.

  The present inventor has succeeded in identifying an olfactory receptor that responds to malodor-causing substances such as nonanoic acid, hexanoic acid, and isovaleric acid, and an antagonist to the olfactory receptor. The present inventor has further found that by using the receptor antagonist, malodor can be suppressed by masking with olfactory receptor antagonism, and the present invention has been completed.

That is, the present invention provides the following.
(1) An antagonist to any one of olfactory receptors selected from OR2W1, OR10A6, OR51E1, OR51I2, and OR51L1, and 4-isopropyl-1-methylcyclohexanecarbaldehyde, 3- (4-tert-butylphenyl) ) Propanal, 3- (4 isopropylphenyl) -2-methylpropanal, 3- (3-isopropyl-phenyl) -butyraldehyde, 3,7-dimethyl-7-hydroxyoctanal, p-tert-butyl-α -Methylhydrocinnamaldehyde, 7-methoxy-3,7-dimethyloctanal, 3- (4-isobutyl-phenyl) -2-methyl-propionaldehyde, 4-isopropyl-1-methylcyclohexylmethanol, 4- (2- Methoxyphenyl) -2-methyl-2-butanol, tetrahydro-4-methyl-2- (2-methylpropyl) -2H-pyran-4-ol, 2,2-dimethyl-3- (3-methylphenyl) propanol 4-isopropylcyclohexa Carbaldehyde, 3,7-dimethyl-6-octenal, 1,2,3,4,5,6,7,8-octahydro-8,8-dimethyl-2-naphthalenecarboxaldehyde, 2,4,6-trimethyl -3-cyclohexene-1-carboxaldehyde, 3,5,6-trimethyl-3-cyclohexene-1-carboxaldehyde, 2,4-dimethyl-3-cyclohexane-1-carboxaldehyde, 4-isopropylbenzaldehyde, and 2- A malodor control agent comprising one or more antagonists selected from the group consisting of cyclohexylpropanal as active ingredients.
(2) The malodor control agent according to (1), wherein the malodor is a smell of nonanoic acid, hexanoic acid or isovaleric acid.
(3) 3- (4-tert-butylphenyl) propanal, 3- (3-isopropyl-phenyl) -butyraldehyde, 7-methoxy-3,7-dimethyloctanal, 2,4,6-trimethyl-3 The malodor according to (1) or (2), wherein the active ingredient is at least one selected from the group consisting of 2-cyclohexene-1-carboxaldehyde and 3,5,6-trimethyl-3-cyclohexene-1-carboxaldehyde Inhibitor.
(4) 4-Isopropyl-1-methylcyclohexanecarbaldehyde, 3- (4-tert-butylphenyl) propanal, 3- (4 isopropylphenyl) -2-methylpropanal, 3- (3-isopropyl-phenyl) -Butyraldehyde, 3,7-dimethyl-7-hydroxyoctanal, p-tert-butyl-α-methylhydrocinnamaldehyde, 7-methoxy-3,7-dimethyloctanal, 3- (4-isobutyl-phenyl) -2-methyl-propionaldehyde, 4-isopropyl-1-methylcyclohexylmethanol, 4- (2-methoxyphenyl) -2-methyl-2-butanol, tetrahydro-4-methyl-2- (2-methylpropyl)- 2H-pyran-4-ol, 2,2-dimethyl-3- (3-methylphenyl) propanol, 4-isopropylcyclohexanecarbaldehyde, 3,7-dimethyl-6-octenal, 1,2,3,4,5 , 6,7,8-Octahydro-8,8-dimethyl-2-naphthalenecarboxy Rudehydr, 2,4,6-trimethyl-3-cyclohexene-1-carboxaldehyde, 3,5,6-trimethyl-3-cyclohexene-1-carboxaldehyde, 2,4-dimethyl-3-cyclohexane-1-carboxaldehyde , A receptor antagonist for any one of olfactory receptors selected from OR2W1, OR10A6, OR51E1, OR51I2, and OR51L1, selected from the group consisting of 4-isopropylbenzaldehyde and 2-cyclohexylpropanal.
(5) 3- (4-tert-butylphenyl) propanal, 3- (3-isopropyl-phenyl) -butyraldehyde, 7-methoxy-3,7-dimethyloctanal, 2,4,6-trimethyl-3 The antagonist according to (4), which is -cyclohexene-1-carboxaldehyde or 3,5,6-trimethyl-3-cyclohexene-1-carboxaldehyde.

  According to the present invention, a bad odor is specifically produced without causing problems such as low immediate effect and uncomfortable feeling based on the fragrance of the fragrance, which have occurred in the conventional odor eliminating method using the odor eliminating agent and the fragrance. It can be deodorized.

Response of olfactory receptors to hexanoic acid and nonanoic acid. The horizontal axis represents individual olfactory receptors, and the vertical axis represents response intensity. Response of olfactory receptors to various concentrations of isovaleric acid. FIG. 6 shows the concentration-dependent inhibition of the test substance on the hexanoic acid response of the receptor. Sensory evaluation of the ability to suppress hexanoic acid odor by burgeonal and fluorhydral. Sensory evaluation of nonanoic acid odor control ability by test substance. Sensory evaluation of ability to suppress isovaleric acid odor by test substances. Sensory evaluation of ability to suppress cresol odor by test substance.

  In this specification, the term “masking” relating to odor refers to all means for making the target odor unrecognized or weakening recognition. “Masking” may include chemical means, physical means, biological means, and sensory means. For example, as masking, any means for removing odor molecules that cause the target odor from the environment (for example, adsorption and chemical decomposition of odor molecules), to prevent the target odor from being released into the environment. (For example, containment), a method of adding another odor such as a fragrance or a fragrance to make it difficult to recognize the target odor, and the like.

  In the present specification, “masking by olfactory receptor antagonism” is a form of the above-mentioned “masking” in a broad sense, and by applying both an odor molecule of a target odor and another odor molecule, This is a means for inhibiting the receptor response to the target odor molecule by the odor molecule, and consequently changing the odor recognized by the individual. Masking by olfactory receptor antagonism is distinguished from means for canceling the target odor by another strong odor, such as a fragrance, even if the means uses other odor molecules. One example of masking by olfactory receptor antagonism is the case of using a substance that inhibits the activity of the olfactory receptor, such as an antagonist (antagonist). If a substance that inhibits the activity is applied to the receptor of the odor molecule that brings about a specific odor, the response activity of the receptor to the odor molecule is suppressed, so that the odor finally perceived by the individual is changed. be able to.

  Therefore, as one aspect, the present invention provides a malodor control agent comprising an olfactory receptor antagonist for malodor as an active ingredient. The malodor to be suppressed includes a hexanoic acid odor, a nonanoic acid odor, and an isovaleric acid odor. These odors are generally known as body odors (or fatty acid odors) caused by sweat or sebum, for example. Any one or more of these odors, preferably both, are suppressed by the malodor control agent of the present invention.

  Examples of the olfactory receptor for the malodor include any one of olfactory receptors selected from OR2W1, OR10A6, OR51E1, OR51I2, and OR51L1. The antagonist which is an active ingredient of the malodor control agent of the present invention may be an antagonist for any one of these olfactory receptors or an antagonist for a plurality of them. As shown in FIGS. 1 and 2, the olfactory receptor exhibits a response to nonanoic acid, hexanoic acid or isovaleric acid odor. Therefore, if the response activity of these receptors is suppressed, the recognition of nonanoic acid odor, hexanoic acid odor or isovaleric acid odor in the center changes, and therefore masking by olfactory receptor antagonism causes nonanoic acid, hexanoic acid or Odor due to isovaleric acid can be suppressed.

  Examples of the antagonist include substances shown in Table 1 below. As shown in Table 3, these substances are antagonists (antagonists) of the olfactory receptor that suppress the activity of the olfactory receptor. These substances have been conventionally known as fragrances, but have not been known so far to have olfactory receptor antagonist activity.

  Among the antagonists listed in Table 1, as an active ingredient of the malodor control agent of the present invention, preferably 4-isopropyl-1-methylcyclohexanecarbaldehyde, burgeonal, flurohydral, hydroxycitronellal, 4-isopropylcyclohexanecarbaldehyde, 4- (2-methoxyphenyl) -2-methyl-2-butanol, Florosa, Cyclemone A, Isocyclocitral, Tripral, Polenal II, Methoxycitronellal, and more preferred are burgeonal, Fluorhydral, hydroxycitrone Lar, 4-isopropylcyclohexanecarbaldehyde, fluroza, isocyclocitral, tripral, polenal II, methoxycitronellal, more preferably burgeonal, flurohydral, methoxycyto Roneral and isocyclocitral are mentioned.

Among the antagonists listed in Table 1, burgeonal (3- (4-tert-butylphenyl) propanal), flurohydral (3- (3-isopropyl-phenyl) -butyraldehyde), lyial (p-tert-butyl-α) -Methylhydrocinnaldehyde), Florosa (tetrahydro-4-methyl-2- (2-methylpropyl) -2H-pyran-4-ol) is available from Givaudan and Suzalar (3- (4-isobutyl- (Phenyl) -2-methyl-propionaldehyde) is available from Takasago International Corporation, and majantol (2,2-dimethyl-3- (3-methylphenyl) propanol) is available from Symrise. Cyclemone A (1,2,3,4,5,6,7,8-octahydro-8,8-dimethyl-2-naphthalenecarboxaldehyde), tripral (2,4-dimethyl-3-cyclohexane-1-) Carboxaldehyde) is available from International Flavors & Fragrances, and Polenal II (2-cyclohexylpropanal) is available from Kao Corporation. Cyclamenaldehyde (3- (4-isopropylphenyl) -2-methylpropanal), hydroxycitronellal (3,7-dimethyl-7-hydroxyoctanal), methoxycitronellal (7-methoxy-3,7- Dimethyl octanal), citronellal (3,7-dimethyl-6-octenal), isocyclocitral (2,4,6-trimethyl-3-cyclohexene-1-carboxaldehyde, 3,5,6-trimethyl-3-cyclohexene) -1-carboxaldehyde) and cuminaldehyde (4-isopropylbenzaldehyde), as described in “Synthetic perfume chemistry and product knowledge augmented revised edition Motoichi Into, Chemical Industry Daily,” for example, International Flavors & Fragrances and Givaudan It can be obtained from Takasago International Corporation. 4-Isopropyl-1-methylcyclohexanecarbaldehyde can be synthesized, for example, by the method described in JP-A-2009-149811. Further, 4-isopropyl-1-methylcyclohexylmethanol can be synthesized, for example, by the method described in JP 2008-1667 A, and 4- (2-methoxyphenyl) -2-methyl-2-butanol is For example, it can be synthesized by the method described in JP-A-9-111281.
As an example, 4-isopropylcyclohexanecarbaldehyde can be synthesized from 1554.57 g of 4-isopropylcyclohexylmethanol (Mayol) (Mayol: Firmenich) as a starting material by the method described in JP-A-2-188549. The resulting product is identified, for example, as follows.
¹ H-NMR (CDCl ₃ , 400 MHz, δ ppm): 0.80 (3H, d, 6.8 Hz) 0.84 (3H, d, 6.8 Hz), 0.97-1.03, 1.19-1.30, 1.37-1.48, 1.51-1.61, 1.81 -1.86, 1.95-1.99, 2.10-2.20 (10H, all m), 2.38-2.42 (1H, m), 9.56 (0.5H, s), 9.66 (0.5H, s)
¹³ C-NMR (CDCl ₃ , 100 MHz, δ ppm): 19.87, 19.92 (q), 24.79, 26.32, 26.57, 28.63 (t), 32.14, 32.84, 43.31, 43.60 (d), 47.18, 50.68 (d), 204.60, 205.51 (d)

  The active ingredient of the malodor control agent of the present invention may be any one or more of the above antagonists. That is, the malodor control agent of the present invention contains any of the above antagonists alone or in combination of two or more. Preferably, the malodor control agent of the present invention consists essentially of any one or a combination of two or more of the above antagonists.

  As another aspect, the present invention provides a malodor control method comprising the step of causing malodor and an olfactory receptor antagonist against the malodor to coexist. In the method, an antagonist of a receptor against the malodor is applied to an individual who needs inhibition of malodor recognition, preferably an individual who needs inhibition of malodor recognition by masking with olfactory receptor antagonism, The malodor and the antagonist are allowed to coexist. As a result, the malodor receptor and the antagonist are combined to suppress the activity of the receptor, so that masking by olfactory receptor antagonism occurs and malodor is suppressed.

  In the method of the present invention, the individual is not particularly limited as long as it is a mammal, but is preferably a human. The types of malodor to be suppressed, olfactory receptors, and antagonists used are the same as in the case of the above-mentioned malodor suppressor.

  The antagonists described in Table 1 can be used for malodor control by masking by olfactory receptor antagonism based on inhibition of the activity of any one of the olfactory receptors, and compounds or compositions for such malodor control Can be used for the manufacture of things. The malodor control compound or composition is a component having other deodorizing effects in addition to the antagonists shown in Table 1, or any component used for a deodorant or deodorant, such as a fragrance or a powder component. , Liquid fats and oils, solid fats and oils, waxes, hydrocarbons, plant extracts, Chinese herbal ingredients, higher alcohols, lower alcohols, esters, long chain fatty acids, surfactants (nonionic surfactants, anionic surfactants, cations Surfactants, amphoteric surfactants, etc.), sterols, polyhydric alcohols, humectants, water-soluble polymer compounds, thickeners, film agents, bactericides, preservatives, UV absorbers, retention agents, cooling sensations Agent, warming agent, stimulant, sequestering agent, sugar, amino acids, organic amines, synthetic resin emulsion, pH adjuster, antioxidant, antioxidant assistant, oil, powder, capsules, chelating agent , Inorganic salt, yes For purposes such as salt pigments, thickeners, bactericides, antiseptics, fungicides, colorants, antifoaming agents, extenders, modulators, organic acids, polymers, polymer dispersants, enzymes, enzyme stabilizers, etc. You may contain suitably according to it.

  As other components having a deodorizing effect that can be contained in the malodor control compound or composition, any known deodorant can be used. For example, plant leaves, petioles, berries, stems, roots, bark Deodorant active ingredient extracted from each part such as (green tea extract); lactic acid, gluconic acid, succinic acid, glutanic acid, adipic acid, malic acid, tartaric acid, maleic acid, fumaric acid, itaconic acid, citric acid Organic acids such as benzoic acid and salicylic acid, various amino acids and salts thereof, glyoxal, oxidizing agent, flavonoids, catechins, polyphenols; porous materials such as activated carbon and zeolite; inclusion agents such as cyclodextrins; photocatalysts Various masking agents and the like.

  As shown in the Examples below, the antagonists shown in Table 1 suppress the response to odor molecules of olfactory receptors selected from OR2W1, OR10A6, OR51E1, OR51I2, and OR51L1, and if the antagonist is used, The odor derived from the odor molecule sensed by the receptor can be odor-specifically suppressed by masking with the olfactory receptor antagonism.

  EXAMPLES Hereinafter, an Example is shown and this invention is demonstrated more concretely.

Example 1 Cloning of Human Olfactory Receptor Gene Human olfactory receptor was cloned by PCR using human genomic DNA female (G1521: Promega) as a template based on sequence information registered in GenBank. Each gene amplified by the PCR method is inserted into the pENTR vector (Invitrogen) according to the manual, and Not I created downstream of the Flag-Rho tag sequence on the pME18S vector using the Not I and Asc I sites present on the pENTR vector. Recombined into I and Asc I sites.

Example 2 Production of pME18S-hRTP1S Vector Human RTP1S was cloned by PCR using the human RTP1 gene (MHS1010-9205862: Open Biosystems) as a template. The primers used for PCR were EcoR I on the sense side and Xho I site on the antisense side. The hRTP1S gene (SEQ ID NO: 1) amplified by the PCR method was incorporated into the EcoR I and Xho I sites of the pME18S vector.

Example 3 Identification of Olfactory Receptor Responding to Malodor 1) Preparation of Olfactory Receptor-Expressing Cells HEK293 cells each expressing 350 types of human olfactory receptors were prepared. A reaction solution having the composition shown in Table 2 was prepared and allowed to stand in a clean bench for 15 minutes, and then added to each well of a 96-well plate (BD). Next, 100 μl of HEK293 cells (3 × 10 ⁵ cells / cm ² ) were seeded in each well and cultured for 24 hours in an incubator maintained at 37 ° C. and 5% CO ₂ .

2) Luciferase assay The olfactory receptor expressed in HEK293 cells increases the amount of intracellular cAMP by coupling with intracellular Gαs and activating adenylate cyclase. For the measurement of odor response in this study, a luciferase reporter gene assay was used to monitor the increase in intracellular cAMP level as a luminescence value derived from the firefly luciferase gene (fluc2P-CRE-hygro). In addition, a renilla luciferase gene fusion (hRluc-CMV) downstream of the CMV promoter was simultaneously introduced, and used as an internal standard for correcting errors in gene transfer efficiency and cell number.
From the culture prepared in 1) above, the medium was removed with a pipette, and 75 μl of a solution containing an odorant (hexanoic acid 1 mM or nonanoic acid 300 μM) prepared with CD293 medium (Invitrogen) was added. The cells were cultured for 4 hours in a CO ₂ incubator to fully express the luciferase gene in the cells. The activity of luciferase was measured using a Dual-Glo ^™ luciferase assay system (promega) according to the operation manual of the product. A value obtained by dividing the luminescence value derived from firefly luciferase induced by odorant stimulation by the luminescence value in cells not subjected to odorant stimulation was calculated as a fold increase and used as an indicator of response intensity.

3) Results
Five types of olfactory receptors OR2W1, OR10A6, OR51E1, OR51I2 and OR51L1 responded to hexanoic acid, and three types of olfactory receptors OR2W1, OR10A6 and OR51E1 responded to nonanoic acid (Fig. 1).

  The response of the olfactory receptors OR2W1, OR10A6, OR51E1, OR51I2, and OR51L1 to isovaleric acid (0, 3, 10, 30, 100, 300, and 1000 μM) was examined by the same procedure as described above. The olfactory receptors OR51E1 and OR51I2 responded to isovaleric acid in a concentration-dependent manner (FIG. 2).

Example 4 Measurement of malodor receptor inhibitory activity The olfactory receptor identified in Example 3 was used as a target, and the receptor activity inhibitory activity of 52 types of test substances was examined.
In the same manner as in Example 3, OR2W1, OR10A6, OR51E1, OR51I2, and OR51L1 were expressed in HEK293 cells, and luciferase assay was performed. In the luciferase assay, hexanoic acid was used as an odor substance, and a test substance was added together with hexanoic acid. The response of olfactory receptors to hexanoic acid was measured, and the decrease in receptor response activity due to the addition of test substances was evaluated.
The inhibition rate of receptor activity by the test substance was calculated as follows. The luminescence value (X) derived from firefly luciferase induced by odor stimulation with hexanoic acid alone was subtracted by the luminescence value (Y) in the cells in which the same receptor was introduced and no odor stimulation was performed. Similarly, the luminescence value (Z) by stimulation with a mixture of hexanoic acid and the test substance was subtracted by the luminescence value (Y) in cells not subjected to odor stimulation. The receptor activity inhibitory activity by the test substance was calculated by the following calculation formula based on the increase in luminescence value due to stimulation with hexanoic acid alone (XY). Independent experiments were performed several times in duplicate, and the average value of each experiment was obtained.
Inhibition rate (%) = {1- (ZY) / (XY)} × 100
As a result, seven test substances for OR2W1, three kinds for OR10A6, seven kinds for OR51E1, ten kinds for OR51I2, and six kinds of test substances for OR51L1 have receptor activity. Inhibitory activity was shown (Table 3).

  In addition, all test substances that showed inhibitory activity were examined for concentration-dependent inhibition of the hexanoic acid response. The test substance concentrations used were 3, 10, 30, 100, and 300 μM. With respect to the response of the receptor to 1 mM hexanoic acid under each test substance concentration, the relative response intensity was examined by setting the response intensity of the receptor at a test substance concentration of 0 μM as 100%. As a result, it was shown that among the test substances that showed inhibitory activity, burgeonal and florhydral all inhibited the hexanoic acid response of four olfactory receptors OR2W1, OR51E1, OR51I1, and OR51L1 in a concentration-dependent manner (FIG. 3).

Example 5 Evaluation of Malodor Control Ability of Test Substance The malodor suppression ability of the test substance having receptor activity inhibitory activity identified in Example 4 was confirmed by a sensory test.
Put a cotton ball in a glass bottle (Saiyo Glass No.11, 110ml in volume), and test as a malodor, hexanoic acid diluted 100 times with propylene glycol, 10 times diluted nonanoic acid or 1000 times diluted isovaleric acid, and test 20 μl of the material was dropped onto a cotton ball. The glass bottle was allowed to stand overnight at room temperature, and the odor molecules were sufficiently volatilized in the glass bottle. The sensory evaluation test was conducted by 3 panelists (5 persons for isovaleric acid), the odor intensity when dropping malodor alone was set to 5, and the odor intensity when mixing test substances was 0 to 10 It was evaluated in 20 steps as (0.5 increments).
The test substances were fluorhydral, burgeonal, hydroxycitronellal, 4-isopropylcyclohexanecarbaldehyde, (4- (2-methoxyphenyl) -2-methyl-2-diluted 100 times with propylene glycol for hexanoic acid. Butanol), Florosa, isocyclocitral, tripral, and pollenal II were diluted 10-fold with respect to nonanoic acid, and fluorhydral was diluted 1000-fold with respect to isovaleric acid. As a control substance for the test substance, a perfume floralol (diluted 100 times with propylene glycol), which is a substance having no activity-inhibiting effect on the olfactory receptor, was used, and a similar test was performed on hexanoic acid.

  Fluorhydral and burgeonal that suppress the hexanoic acid response of OR2W1, OR51E1, OR51I2, and OR51L1 significantly suppressed the odor of hexanoic acid (FIG. 4). This suppression of hexanoic acid odor was more remarkable than when the control substance (floralol) was mixed. In addition, as a result of examining nonanoic acid and isovaleric acid, the odor was also suppressed by these test substances (FIGS. 5 and 6). Other substances that suppress the response of one or more hexanoic acid receptors (hydroxycitronellal, 4-isopropylcyclohexanecarbaldehyde, 4- (2-methoxyphenyl) -2-methyl-2-butanol, Florosa , Isocyclocitral, tripral, and pollenal II) were also examined for the effect of suppressing the hexanoic odor, and it was found that all the test substances suppress the hexanoic odor (Table 4).

In order to examine the specificity of malodor control by the test substance having receptor activity inhibitory activity identified in Example 4, it is a malodor different in structure from fatty acid, and the olfactory receptor identified in Example 3 is an odor substance that does not respond A similar sensory test was performed using cresol. In the experiment, cresol diluted 100 times with propylene glycol was used as a bad odor, and fluorhydral diluted 100 times with propylene glycol was used as a test substance.
As a result of the test, the smell of cresol was not suppressed by fluorhydral (FIG. 7). Therefore, the suppression effect was shown to be odor specific.

Claims (3)

  An antagonist to any one of olfactory receptors selected from OR2W1, OR10A6, OR51E1, OR51I2 and OR51L1, and 3- (3-isopropyl-phenyl) -butyraldehyde and 3- (4-tert-butylphenyl) ) A malodor control agent comprising as an active ingredient at least one antagonist selected from the group consisting of propanal.   The malodor control agent according to claim 1, wherein the malodor is nonanoic acid, hexanoic acid or isovaleric acid.   An olfactory receptor selected from OR2W1, OR10A6, OR51E1, OR51I2, and OR51L1, selected from the group consisting of 3- (3-isopropyl-phenyl) -butyraldehyde and 3- (4-tert-butylphenyl) propanal A receptor antagonist for any one of the above.