JP2008173441A - Volatile sulfur compound production inhibitor - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a product having excellent deodorizing effect to volatile sulfur odor produced by pseudomonas bacteria or colibacillus to be capable of continuously inhibiting formation of volatile sulfur compound as a household uncomfortable odor component. <P>SOLUTION: The volatile sulfur compound production inhibitor comprises at least one of aromatic agents as the effective component, selected among saturated aliphatic aldehyde of a carbon number of 6-12, undecenal, terpene family aldehyde, aromatic aldehyde, alicyclic aldehyde of 5- or 6-member ring, alicyclic ketone of 5- or 6-member ring, macrocyclic ketone of a carbon number of 15-17, nootkatone, macrocyclic lactone of a carbon number of 15-16, methyl dihydro jasmonate, nerolidol, and phenyl acetaldehyde dimethyl acetal. Household products are formed to include the volatile sulfur compound production inhibitor or enzyme inhibitor in effective quantity. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

  The present invention relates to a production inhibitor of a volatile sulfur compound that is one of unpleasant odor components in a domestic environment.

  Volatile sulfur compounds such as hydrogen sulfide and methyl mercaptan are unpleasant ingredients that can be perished even at low concentrations. Since these components are neutral compounds and are relatively stable compounds, it is difficult to deodorize them by chemical adsorption or chemical decomposition. Therefore, effective deodorizing and deodorizing techniques have been demanded.

  Conventionally, various chemical substances and plant-derived substances have been used as bactericides and preservatives depending on the treatment target such as food field, medical field, external preparation, household preparation and the like. Recently, however, products derived from natural products such as plants have become popular from the standpoint of safety for products that touch the kitchen or human skin.

  Many conventional perfume ingredients such as essential oils and synthetic fragrances are known to exhibit antibacterial properties against various microorganisms. However, these bactericidal and antibacterial tests indicate that the effect varies greatly depending on the target bacterial species. Therefore, in order to obtain the desired deodorizing and deodorizing effect, it is necessary to select a bacterial species suitable for the purpose and perform a new search.

  Against this background, attempts have been made to suppress the generation of odors by inhibiting microbial metabolic enzymes with fragrances and synthetic fragrance ingredients. Patent Document 1 proposes suppression of production of isovaleric acid by a fragrance component. On the other hand, regarding suppression of volatile sulfur compounds, Patent Document 2 discloses a methioninase inhibitor derived from a plant extract. However, the methioninase inhibitors shown in Reference 2 are calahoo, honoki, akamegashiwa, mulberry, iceland moss, guava, hoehound, guarana, plantain, alcanet, akebi, wolfberry, kagosou, oregano, fennel, lotus, kumquat, green tea And perilla, derived from a plant extract that is not used as a fragrance. Furthermore, Patent Document 3 and Patent Document 4 report that the specific perfume component exhibits an effect of inhibiting the production of methyl mercaptan by obligately anaerobic Fusobacterium nucleatum, which is an oral bacterium. However, Patent Documents 3 and 4 do not mention the methioninase inhibitory effect, and these techniques relate to microorganism-related odor suppression related to bad breath.

  The reason why unpleasant raw garbage generates volatile sulfur compounds, which are rotten odors, is that they are decomposed by bacteria to produce malodorous gases such as ammonia, methyl mercaptan, and hydrogen sulfide. For example, it has been known that volatile sulfur odor components generated from meat and milk are produced by microorganisms in the environment (Non-patent Document 1). In addition, dimethyl disulfide, dimethyl trisulfide, and the like are detected as odor components in bathroom walls and drains, causing odors of concern. According to Non-Patent Document 1, these volatile sulfur odors are generated by the action of bacteria, yeast, cocoons, and single-celled algae. However, when looking at the generation of volatile sulfur compounds in the domestic environment, Pseudomonas bacteria, which is a kind of aerobic Gram-negative bacteria, and Escherichia coli, which is a kind of facultative anaerobic Gram-negative bacteria, are the main causative bacteria. ing.

  Thus, many plant extracts and essential oils have been proposed as fungicides, preservatives, and deodorants, but these perfume ingredients are Pseudomonas, which are microorganisms involved in the generation of volatile sulfur odors in the home. The bactericidal and antibacterial effects against genus bacteria and Escherichia coli were weak. Moreover, there was no prior art which showed the effect regarding inhibition of the volatile sulfur compound production enzyme of these microorganisms.

JP 2002-255774 A JP 2005-162697 A JP 2001-348308 A JP 2003-26527 A Annual Review of Microbiology, 16, 127-138, 1972

  Therefore, the present invention has a high deodorizing and deodorizing effect on volatile sulfur compound odors produced by Pseudomonas bacteria and Escherichia coli, and can continuously suppress the production of volatile sulfur compounds that are unpleasant odor components in the home. The purpose is to provide.

  As a result of various studies on plant-derived and synthetic fragrance ingredients generally used for flavoring, the present inventors have found that specific aldehydes, specific ketones, specific lactones, nootkatone, methyl dihydrojasmonate, nerolidol and It has been found that a perfume component selected from phenylacetaldehyde dimethyl acetal suppresses the production of volatile sulfur compounds from cysteine or methionine by facultative anaerobic bacteria and aerobic bacteria and effectively reduces unpleasant odors.

  The present invention relates to a saturated aliphatic aldehyde having 6 to 12 carbon atoms, undecenal, terpene aldehyde, aromatic aldehyde, 5-membered or 6-membered alicyclic aldehyde, 5-membered or 6-membered alicyclic ketone. Volatilization containing at least one perfume selected from macrocyclic ketones having 15 to 17 carbon atoms, nootkatone, macrocyclic lactones having 15 to 16 carbon atoms, methyl dihydrojasmonate, nerolidol and phenylacetaldehyde dimethyl acetal as active ingredients It is intended to provide a functional sulfur compound production inhibitor.

  The present invention also provides an inhibitor of an enzyme that produces hydrogen sulfide from cysteine and an inhibitor of an enzyme that produces methyl mercaptan from methionine, which contain at least one of the above fragrances as an active ingredient.

  Furthermore, the present invention provides a household product containing an effective amount of the above-mentioned volatile sulfur compound production inhibitor or enzyme inhibitor.

  Since the volatile sulfur compound production inhibitor of the present invention can continuously suppress the generation of volatile sulfur compounds that are unpleasant odor components in the home, it has an excellent deodorizing effect and high safety, and has a soft finish. It is useful as a household product such as an agent and a deodorant.

  Of the volatile sulfur compounds that are unpleasant odor components, hydrogen sulfide is produced from cysteine, which is a sulfur-containing amino acid, by cysteine desulfurase, and methyl mercaptan is produced from methionine by the action of methioninase (methionine-γ-lyase). Furthermore, dimethyl sulfide, dimethyl disulfide, and dimethyl trisulfide are generated enzymatically or oxidatively from methyl mercaptan or hydrogen sulfide. The present inventors have clarified that these hydrogen sulfide and methyl mercaptan are produced by microorganisms that inhabit kitchen garbage bins, bathrooms, washing tubs, etc. (Reference Example 1). In addition, Escherichia coli NBRC3301, Pseudomonas aeruginosa NBRC12689, Bacillus subtilis JCM1465T produce these odor components and hydrogen sulfide from cysteine by Pseudomonas aeruginosa cell extracts. Was confirmed to be produced at a level that can be sufficiently perceptually sensed (Reference Examples 2 and 3).

  On the other hand, as an enzyme inhibitor that produces hydrogen sulfide or methyl mercaptan from cysteine or methionine, an example of aminooxyacetic acid known as an enzyme inhibitor using pyridoxal phosphate as a coenzyme has been known. From the viewpoint of sex, its use is difficult. Regarding the inhibition of the enzymes of Pseudomonas aeruginosa and Escherichia coli, there have been no examples of fragrance ingredients reported so far. Were found to have such inhibitory activity (Examples 1 and 2). More surprisingly, these fragrances did not inhibit the growth of Pseudomonas aeruginosa at their inhibitory concentrations (Reference Example 5). This indicates that the inhibitory activity is not the effect of sterilizing the Pseudomonas aeruginosa used, but the effect of inhibiting the enzyme involved in the generation of odor components. What is important here is that the inventors have obtained an important finding that a sufficient deodorizing effect is exhibited even at a concentration below the sterilizing power, and shows the effectiveness of enzyme inhibition in inhibiting odor generation. Furthermore, the enzyme inhibitory activity was recognized also in the fragrance | flavor which has a structure similar to the fragrance | flavor by which the volatile sulfur compound production | generation suppression effect was recognized in Example 3 and 4 (Example 8). Furthermore, a similar enzyme inhibitory activity was also confirmed for lactones other than aldehydes and ketones, nerolidol and phenylacetaldehyde dimethyl acetal (Example 8).

  Therefore, the fragrance component used in the present invention is an inhibitor of the generation of volatile sulfur compounds by facultative anaerobic microorganisms and aerobic bacteria living in the home, or an enzyme that generates hydrogen sulfide from cysteine or methyl mercaptan from methionine. They can be used as inhibitors of the enzyme produced, and at the same time, they can be used as a flavoring / deodorizing agent that suppresses the generation of unpleasant odors in the home environment.

The fragrance used as the volatile sulfur compound production inhibitor or enzyme inhibitor of the present invention is a saturated aliphatic aldehyde having 6 to 12 carbon atoms, undecenal, terpene aldehyde, aromatic aldehyde, 5-membered ring or 6-membered ring. Alicyclic aldehydes, 5-membered or 6-membered alicyclic ketones, macrocyclic ketones having 15 to 17 carbon atoms, nootkatone, macrocyclic lactones having 15 to 16 carbon atoms, methyl dihydrojasmonate, nerolidol and phenyl A fragrance selected from acetaldehyde dimethyl acetal.
Examples of the saturated aliphatic aldehyde having 6 to 12 carbon atoms include hexanal, heptanal, octanal, nonanal, decanal, undecanal, dodecanal, and methylnonylacetaldehyde.
Examples of the terpene aldehyde include citral, citronellal, hydroxycitronellal and the like.
Aromatic aldehydes preferably have 7 to 15 carbon atoms, especially 8 to 15 carbon atoms, and include benzaldehyde, heliotropin, phenylpropylaldehyde, anisaldehyde, vanillin, cyclamenaldehyde, ethyl vanillin, 2-methyl-3- ( 3,4-methylenedioxyphenyl) -propanal (IFF company; helional), phenylacetaldehyde, cinnamic aldehyde, amyl cinnamic aldehyde, hexyl cinnamic aldehyde and the like.
The 5- or 6-membered alicyclic aldehyde preferably has 9 to 14 carbon atoms, particularly 13 to 14 carbon atoms. 4- (4-hydroxy-4-methylpentyl) -3-cyclohexene-1 -Carboxaldehyde (IFF: Lyral), 4- (4-Methyl-3-pentenyl) -3-cyclohexene-1-carboxaldehyde (IFF: Mylacaldehyde), 4-tricyclo [5.2.1.0 ^2,6 ] Decylidene-8) -butenal (IFF: Dupicar), dimethyl tetrahydrobenzaldehyde (IFF: tripral, Quest: ligustral, etc.) and the like.
As the 5-membered or 6-membered alicyclic ketone, those having 11 to 14 carbon atoms are preferable, α-ionone, β-ionone, α-damascon, β-damascon, α-methylionone, γ-methylionone, Cis Jasmon and the like.
Examples of macrocyclic ketones having 15 to 17 carbon atoms include 4-cyclopentadecenone (Firmenich: Exzartenone), 8-cyclohexadecen-1-one (Symrise: Globanone), 9-cycloheptadecen-1-one ( Sibeton) and the like.
Examples of the macrocyclic lactone having 15 to 16 carbon atoms include 10-oxa-16-hexadecenolide (oxalide), 7-cyclohexadecenolide (ambretlide) and the like.

  As these perfume compounds, those isolated from essential oils may be used, or those chemically synthesized may be used. Furthermore, you may use the essential oil containing these fragrance | flavor compounds, for example, lemongrass oil, lemon oil, orange oil, cinnamon oil, grapefruit oil etc. as it is. These perfume compounds or essential oils may be used in combination of two or more.

  The volatile sulfur compound production inhibitor of the present invention is a product having a high deodorizing and deodorizing effect against unpleasant odors in the home by containing an effective amount in household products such as home use and facility use. can do. Examples of household products include household cleaners such as kitchens and bathrooms, residential deodorants, clothing detergents, clothing softeners, clothing deodorants, dishwashers, and washing tank cleaners. Can be mentioned. It is also possible to use several usage methods in combination.

  When used as a cleaning agent, softening agent, or deodorant, the content of the volatile sulfur compound production inhibitor is generally preferably 0.0001 to 3% by weight, more preferably 0.001 to 1% by weight, particularly 0.005. It is preferable to set it to -0.5 weight%.

  The house hold product of the present invention includes various components usually used in house hold products, such as oils, surfactants, alcohols, chelating agents, pH adjusters, preservatives, thickeners, pigments, and fragrances. It can be formulated by arbitrarily combining components such as a moisturizer, softener, keratin protective agent, medicinal agent, antioxidant, solvent and the like.

  The household product and the volatile sulfur compound production inhibitor of the present invention are locally applied to kitchen trash, dishwashing sponges, bathroom walls, washing tubs, laundry garments and other places where unpleasant odors are likely to occur. By doing so, generation of an unpleasant odor can be controlled. Furthermore, the unpleasant odor from the clothes after washing can be suppressed by mix | blending with the detergent for clothes, or the softener for clothes. The amount of these preparations used varies depending on the content of the active ingredient. For example, in the case of a liquid preparation, it is preferable to apply 1 to 20 pushes by spraying.

Reference Example 1 Generation of Volatile Sulfur Compounds from Household Sampling Bacteria (1) Bacteria Sampling Method 3 Around the household sink (garbage basket), bathroom wall tile joints, around the bathroom drain, and inside the washing machine washing tub The microorganisms were collected by rubbing with BBL Culture Swab EZ (Becton Dickinson). The collected sample was transported to the laboratory at room temperature. The urethane part at the tip of the sample is cut with a 70% ethanol-sterilized scissors, placed in a 1.5mL centrifuge tube containing 0.5mL of physiological saline (Otsuka Pharmaceutical Co., Ltd.), and shaker (CUTE MIXER C-1000) : EYLA) and stirred at 1200 rpm for 10 minutes. After stirring, the urethane part was removed to obtain a collected bacterial solution.

(2) Measurement of Volatile Sulfur Compounds Test in which sterile Muller Hinton medium (Becton Dickinson) 0.01mL, 50mM cysteine solution or 0.1mL of 50mM methionine solution and 0.07mL of sterile ion-exchanged water were mixed in a sterile vial (5mL). The solution was mixed with 0.02 mL of the collected bacterial solution and allowed to stand in a thermostatic bath at 30 ° C. One day later, volatile sulfur compounds in the headspace gas at the top of the vial were measured. For the measurement, OralChroma (ABILIT) was used. Table 1 shows the amount of volatile sulfur compounds produced relative to the control.

As shown in Table 1, generation of hydrogen sulfide or methyl mercaptan from cysteine was observed in any sample collected from the garbage basket around any household kitchen sink, and hydrogen sulfide, methyl mercaptan or dimethyl sulfide from methionine. Generation was confirmed. In all samples, production of methyl mercaptan from methionine was confirmed.
In addition, as a result of sensory evaluation of the odor of the vial after measurement, a volatile sulfur odor was recognized at a clearly recognized level. From this, it was confirmed that microorganisms that generate volatile sulfur compounds are present in the kitchen sink, bathroom, and washing tub in the home.

Reference Example 2 Production of Volatile Sulfur Compound by Standard Bacteria E. coli NBRC3301, Pseudomonas aeruginosa NBRC12689 and Bacillus subtilis JCM1465T were cultured on an SCD plate for 1 day, and then 1 loop of cultured cells was suspended in 1 mL of physiological saline. This suspension was used in place of the collected bacterial solution from household in Reference Example 1, and the production of volatile sulfur compounds was confirmed in the same manner as in Reference Example 1 (2).
As a result, as shown in FIG. 1, production of hydrogen sulfide from cysteine and production of methyl mercaptan from methionine by E. coli NBRC3301, Pseudomonas aeruginosa NBRC12689, and Bacillus subtilis JCM1465T were confirmed.

Reference Example 3 Production of Volatile Sulfur Compounds from Cell Extract (1) Preparation of Cell Extract
One loop of Pseudomonas aeruginosa NBRC12689 cultured for 1 day on an SCD plate was inoculated into four 50 mL centrifuge tubes containing 20 mL of a 15 mM methionine-added Mueller-Hinton medium, and cultured for 1 day by shaking. After culturing, centrifugation was performed at 3000 rpm for 20 minutes (Hitachi, Ltd.), and the supernatant was removed. 20 mL of ice-cooled 0.8 wt% salt-added phosphate buffer (pH 7.2) was added to suspend the cells, and the suspension was centrifuged. After centrifugation, the supernatant was completely removed and the cells were collected. About 0.4 g (wet weight) of the recovered cells for 4 cells was stored frozen at -20 ° C.
One day later, the frozen cells were lysed with CelLytic B Plus (SIGMA). That is, 4 mL of the solution was added to 0.4 g (wet weight) of the bacterial cells, and the mixture was shaken at room temperature for 20 minutes. After shaking, centrifugation was performed at 10,000 rpm for 20 minutes to remove undissolved residues. The bacterial cell lysate (hereinafter referred to as “bacterial cell extract”) was sterilized with a 0.22 μm filter (Millipore, Milex GV). Add 18 mL of 100 mM phosphate buffer (pH 7.2) with 20 μM pyridoxal phosphate added to ice to 2 mL of the sterilized bacterial cell extract, and centrifuge and concentrate with VIVASPIN20 (molecular weight cut off 10,000) of VIVA SCIENCE Went. After concentrating to 1 mL, 9 mL of the same buffer was further added and centrifugal concentration was performed again to exchange the buffer. By the above operation, 2 mL of bacterial cell extract was finally obtained.

(2) Measurement of volatile sulfur compounds In a sterile vial (5 mL volume), 0.02 mL of Mueller-Hinton's medium, 0.05 mL of 100 mM cysteine solution and 0.305 mL of sterile ion-exchanged water were mixed with 0.025 mL of the above bacterial cell extract solution. mL was mixed and allowed to stand in a constant temperature bath at 30 ° C.
One day later, volatile sulfur compounds in the headspace gas at the top of the vial were measured with OralChroma (ABILIT). As a result, it was confirmed that hydrogen sulfide was generated by adding the bacterial cell extract, that is, by enzymatic reaction. In addition, as a result of evaluating the odor of the reaction solution, the odor of hydrogen sulfide was felt at a sufficiently recognizable level.

Reference Example 4 Production of Volatile Sulfur Compound Using Commercial Methionine-γ-Lyase Production of methyl mercaptan from methionine was confirmed using a commercially available Pseudomonas obalis-derived methionine-γ-lyase (Wako Pure Chemical Industries, Ltd.). That is, 1 mg of commercially available methionine-γ-lyase was dissolved in 100 mM phosphate buffer (pH 7.2) to which 1 mL of 20 μM pyridoxal phosphate was added to prepare an enzyme solution. In a sterile vial (5 mL volume), add 0.05 mL of phosphate buffer adjusted to 1 M pH 8, 0.001 mL of 10 mM pyridoxal phosphate solution, 0.125 mL of 100 mM methionine solution and 0.365 mL of sterile ion-exchanged water, and 0.005 enzyme solution. mL was mixed and it left still in a 30 degreeC thermostat.
One day later, volatile sulfur compounds in the headspace gas at the top of the vial were measured with OralChroma (ABILIT). As a result, production of methyl mercaptan was confirmed. In addition, as a result of evaluating the odor of the reaction solution, the odor of methyl mercaptan was felt at a sufficiently recognizable level.

Example 1 Suppression of volatile sulfur compound-forming activity of bacterial cell extract by specific fragrance
A substrate solution A was prepared by mixing 2 mL of 0.5 M borate buffer (pH 8.5), 0.02 mL of 10 mM pyridoxal phosphate solution, 2 mL of 50 mM cysteine solution and 5 mL of sterile ion-exchanged water. Dispense 0.36 mL of this substrate solution A into the lower container of Amicon Ultra-4 (MILLIPORE), add 0.02 mL or 0.004 mL of a 10 wt% fragrance solution dissolved in dipropylene glycol (DPG), respectively, and then reference examples 0.04 mL of the bacterial cell extract prepared in 3 was mixed. After installing the upper filter, dispense 0.4mL of 2mM 5,5'-dithiobis (2-nitrobenzoic acid) 0.25M phosphate buffer (pH7.2) solution into the upper container and put it in a thermostatic bath at 30 ° C. Left to stand. The final fragrance concentration when the added amount of the fragrance is 0.02 mL is 0.5% by weight, and when it is 0.004 mL, it is 0.1% by weight. What added 0.02 mL of DPG instead of the fragrance | flavor was made into the control, and what added 100 mM phosphate buffer (pH7.2) instead of the microbial cell extract was made into the blank.
After the reaction, 0.2 mL of the solution added at the top was dispensed into a 96-well microplate, and the absorbance at 412 nm was measured. From the obtained measured value, the relative inhibitory activity of volatile sulfur compound production was determined according to the following formula (1).

  The results are shown in FIG. From this result, it can be seen that the fragrance sample provided inhibited the production of volatile sulfur compounds by the bacterial cell extract.

Example 2 Suppression of volatile sulfur compound-forming activity of methionine-γ-lyase by specific fragrance 1 mL of 1M phosphate buffer (pH 8.0), 0.02 mL of 10 mM pyridoxal phosphate solution, 2 mL of 50 mM methionine solution and 6.5 mL of sterile ion-exchanged water By mixing, a substrate solution B was prepared. 0.38 mL of this substrate solution B was dispensed into a lower container of Amicon Ultra-4, 0.004 mL of a 10 wt% fragrance solution dissolved in DPG was added, and 0.02 mL of the enzyme solution of Reference Example 4 was mixed. After installing the upper filter, dispense 0.4mL of 2mM 5,5'-dithiobis (2-nitrobenzoic acid) 0.25M phosphate buffer (pH7.2) solution into the upper container and put it in a thermostatic bath at 30 ° C. Left to stand. The final fragrance concentration provided is 0.1% by weight. Instead of the fragrance, 0.004 mL of DPG was added as a control, and instead of the enzyme solution, 100 mM phosphate buffer (pH 7.2) was added as a blank.
After the reaction, 0.2 mL of the solution added at the top was dispensed into a 96-well microplate, and the absorbance at 412 nm was measured. The relative inhibition rate of the generation of volatile sulfur compounds was determined by equation (1).
The results are shown in FIG. From this result, it can be seen that the fragrance sample provided inhibited the production of volatile sulfur compounds from methionine by commercially available methionine-γ-lyase.

Example 3 Suppression of hydrogen sulfide odor production activity of bacterial cells by specific fragrance
One loop of Pseudomonas aeruginosa NBRC12689 cultured on an SCD plate for 1 day was inoculated into a 50 mL centrifuge tube containing 20 mL of a 15 mM methionine-added Mueller-Hinton medium, and cultured for 1 day by shaking. On the other hand, 1 mL of sterilized Mueller-Hinton medium, 4 mL of 50 mM cysteine sterilized by filtration, and 14 mL of sterilized ion-exchanged water were mixed to prepare a substrate solution C. Dispense 0.475 mL of this substrate solution C into a 1.5 mL centrifuge tube, add 0.0025 mL of 10 wt% fragrance DPG solution, add 0.025 mL of the aforementioned Pseudomonas aeruginosa culture solution, and leave it in a thermostatic bath at 30 ° C. I put it. What added 0.0025mL of DPG instead of the fragrance | flavor was made into control. The final concentration of the fragrance provided is 0.05% by weight.
After culturing for 24 hours, the odor evaluation of the hydrogen sulfide of the culture sample was performed by 5 people including 3 odor judgeers. The score of odor evaluation indicates that the odor of hydrogen sulfide is not felt “0”, “1” is felt slightly, “2” is clearly understood, and “3” is felt strongly. The test was carried out by Wilcoxon signed rank sum test against the control. The results are shown in Table 2.

  From the results shown in Table 2, a reduction in hydrogen sulfide odor was observed functionally with all the fragrances provided, and in particular, hexanal, decanal, benzaldehyde, citral, citronellal, β-ionone, methyl dihydrojasmonate, cis -Jasmon, Lilal and Nootkaton suppressed the production of hydrogen sulfide odor from cysteine by Pseudomonas aeruginosa in a dominant manner over the control.

Example 4 Suppression of Methyl Mercaptan Odor Production Activity of Bacteria with Specific Fragrance
One loop of Pseudomonas aeruginosa NBRC12689 cultured on an SCD plate for 1 day was inoculated into a 50 mL centrifuge tube containing 20 mL of a 15 mM methionine-added Mueller-Hinton medium, and cultured for 1 day by shaking. On the other hand, 1 mL of a sterilized Mueller-Hinton medium, 4 mL of 50 mM methionine sterilized by filtration, and 14 mL of sterilized ion-exchanged water were mixed to prepare a substrate solution D. Dispense 0.475 mL of the substrate solution D into a 1.5 mL centrifuge tube, add 0.0025 mL of a 10 wt% fragrance DPG solution, add and mix 0.025 mL of the aforementioned Pseudomonas aeruginosa culture solution, and leave it in a thermostatic bath at 30 ° C. I put it. What added 0.0025mL of DPG instead of the fragrance | flavor was made into control. The final concentration of the fragrance provided is 0.05% by weight.

  After culturing for 24 hours, the odor evaluation of methyl mercaptan as a culture sample was performed by 5 persons including 3 odor judgeers. The odor rating score indicates that the methyl mercaptan odor is "0" not felt, "1" slightly felt, "2" clearly understood, "3" felt strong. The results are shown in Table 3.

  From the results shown in Table 3, in all the fragrances provided, a decrease in the methyl mercaptan odor was also detected sensorially, and in particular, hexanal, octanal, decanal, citral, citronellal, β-ionone, cis-jasmon, rilal and methyl Dihydrojasmonate preferentially suppressed methyl mercaptan odor production from methionine by Pseudomonas aeruginosa.

Reference Example 5 Antibacterial test of specific fragrance against Pseudomonas aeruginosa
One loop of Pseudomonas aeruginosa NBRC12689 cultured on an SCD plate for 1 day was inoculated into a 50 mL centrifuge tube containing 20 mL of a 15 mM methionine-added Mueller-Hinton medium, and cultured for 1 day by shaking. After dispensing 1 mL of a sterilized Mueller-Hinton medium into a 1.5 mL centrifuge tube, 0.01 mL of a 10 wt% fragrance DPG solution was added, and 0.005 mL of the aforementioned Pseudomonas aeruginosa culture solution was added. 200 μL of the mixed solution was dispensed into 2 holes each in a 96-well microplate. After dispensing, the microplate was sealed with a gas permeable seal (AGgene). The microplate was cultured with a cute mixer at 1200 rpm for 18 hours, and then the turbidity at 600 nm was measured. As a result, the growth of bacterial cells was observed with any of the tested flavors of 0.1% by weight.

Example 5 Spray-type deodorant composition A deodorant composition containing the composition (mass%) of the deodorant according to the present invention shown in Table 4 was prepared, put into a trigger spray container, and spray-type deodorant. A composition was prepared.

Example 6 Tableware Cleaning Composition A tableware cleaning composition containing the deodorant according to the present invention having the composition (% by mass) shown in Table 5 was prepared.

Example 7 Softener Composition A softener composition (pH 4) containing the deodorant according to the present invention having the composition (mass%) shown in Table 6 was prepared.

Example 8 Suppression of Volatile Sulfur Compound Formation Activity by Specific Fragrance Except that 10 mM cysteine solution was used instead of 50 mM cysteine solution in Example 1, and 10 mM methionine solution was used instead of 50 mM methionine solution in Example 2. The relative inhibition rate of volatile sulfur compound production by the fragrance shown in Table 7 was determined by the same method as in Example 1 or 2. The final concentration of the fragrance provided was 0.1% by weight. The results are shown in Table 7.

  From the results shown in Table 7, the provided fragrance samples inhibit the production of volatile sulfur compounds from cysteine by Pseudomonas aeruginosa and inhibit the production of volatile sulfur compounds from methionine by methionine-γ-lyase. It was confirmed.

It is the figure which showed the production | generation of the volatile sulfur compound which uses cysteine or methionine as a substrate by a standard microbe. It is the figure which showed the inhibitory effect by a specific fragrance | flavor with respect to the production | generation of the volatile sulfur compound from cysteine by the cell extract of Pseudomonas aeruginosa. It is the figure which showed the inhibitory effect by a specific fragrance | flavor with respect to the production | generation of the volatile sulfur compound from methionine by commercially available methionine-gamma-lyase.

Claims (4)

  C6-C12 saturated aliphatic aldehyde, undecenal, terpene aldehyde, aromatic aldehyde, 5-membered or 6-membered alicyclic aldehyde, 5-membered or 6-membered alicyclic ketone, carbon number 15 To 17 macrocyclic ketones, nootkatone, macrocyclic lactones having 15 to 16 carbon atoms, methyl dihydrojasmonate, nerolidol, and phenylacetaldehyde dimethyl acetal, as an active ingredient, a volatile sulfur compound Production inhibitor.   C6-C12 saturated aliphatic aldehyde, undecenal, terpene aldehyde, aromatic aldehyde, 5-membered or 6-membered alicyclic aldehyde, 5-membered or 6-membered alicyclic ketone, carbon number 15 From cysteine to hydrogen sulfide containing as an active ingredient at least one perfume selected from 1 to 17 macrocyclic ketones, nootkatone, macrocyclic lactones having 15 to 16 carbon atoms, methyl dihydrojasmonate, nerolidol, and phenylacetaldehyde dimethyl acetal Inhibitors of enzymes that produce   C6-C12 saturated aliphatic aldehyde, undecenal, terpene aldehyde, aromatic aldehyde, 5-membered or 6-membered alicyclic aldehyde, 5-membered or 6-membered alicyclic ketone, carbon number 15 Methionine to methyl mercaptan, comprising as an active ingredient at least one perfume selected from 1 to 17 macrocyclic ketones, nootkatone, 15 to 16 macrocyclic lactones, methyl dihydrojasmonate, nerolidol and phenylacetaldehyde dimethyl acetal Inhibitors of enzymes that produce   Household products containing an effective amount of the agent according to any one of claims 1 to 3.

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