Off-odor suppressing agent, fragrance composition for suppressing off-odor, and food and drink in which off-odor contained therein is masked

Abstract

The present invention pertains to an off-odor suppressing agent and a fragrance composition for suppressing off-odor, which are for masking off-odors contained in food and drink. The present invention also pertains to food and drink in which off-odors contained therein are suppressed. An off-odor suppressing agent according to the present invention is for masking off-odors contained in food and drink. A substance that causes the off-odor is a substance that triggers olfactory receptor polypeptide response, the polypeptide being at least one selected from the group consisting of olfactory receptor OR2AG2 and a polypeptide that includes an amino acid sequence having 80% or more identity with the amino acid sequence of said olfactory receptor and that responds to the off-odor-causing substance. The off-odor suppressing agent contains, as a masking component, one or more selected from the group consisting of isoamyl cinnamate, cinnamyl cinnamate, δ-damascone, 2,3-heptanedione, carvacrol, vanitol, and 5-methyl-2-phenyl-2-hexenal.

Description

Offensive odor suppressant, flavor composition for suppressing offensive odor, and food and drink in which offensive odors contained therein are masked

[0001] The present invention relates to an off-odor suppressant that masks off-odor contained in food and drink, a flavor composition for suppressing off-odor, and food and drink in which the off-odor contained in the food and drink has been masked.

[0002] There are various aromas that are inherently contained in foods and beverages or that develop over time. For example, more than 850 aroma components have been identified in roasted coffee (Non-Patent Document 1). Some aroma components are unpleasant or undesirable, and one example of these so-called off-flavors is a dusty (or earthy) odor. When a dusty odor is present in a food product, it can be perceived as dusty, earthy, grassy, ​​powdery, medicinal, or moldy. For example, Patent Document 1 describes the problem of chewing gum and other confectioneries that combine the high-intensity sweetener aspartame with certain fruit flavors developing a grassy, ​​dusty odor, which develops over time and becomes dusty, earthy, powdery, medicinal, or moldy. This "dusty odor" has been described in various ways using combinations of terms, such as earthy, dusty, musty, moldy, smoky, galbanum, bell pepper, vegetable, and green pea. In literature, it is often expressed in two-word contractions ("major aroma note-minor aroma note"), such as "Earthy-Dusty," "Earthy-Musty," or "Dusty-Moldy." While this is understood sensorily, there is no standardized way to describe it due to its sensory nature. Furthermore, Non-Patent Document 2 lists geosmin as a substance that causes earthy off-odors in wine. Countermeasures against these off-odor substances can be broadly divided into methods that suppress the production of off-odor substances and methods that mask the off-odor that occurs. As an example of the former, Patent Document 2 describes a method for suppressing light degradation of apple juice containing apple flavor using purified rosmarinic acid. As an example of the latter, Patent Document 3 describes a method for masking p-cresol, which is known as the deteriorated odor of citral.

[0003] JP 2009-131228 A JP 2001-342489 A International Publication No. 2021 / 235360

[0004] Takasago International Journal No. 170 (2012), p. 6, Takasago International Corporation IR / Public Relations Office, Earthy off-flavor in wine: Evaluation of remedial treatments for geosmin contamination (Food Chemistry 154 (2014) 171-178)

[0005] There is a need for a technology to mask off-flavors contained in food and beverages, particularly off-flavors described as "dusty odors." It is particularly desirable to be able to mask the off-flavors without impairing the flavor of the food and beverages.

[0006] The present invention includes the following aspects [1] to [8]. [1] An off-odor inhibitor for masking an off-odor contained in a food or drink, wherein the off-odor-causing substance is at least one olfactory receptor polypeptide-responsive substance selected from the group consisting of olfactory receptor OR2AG2 and polypeptides that contain an amino acid sequence that is 80% or more identical to the amino acid sequence of the olfactory receptor and that are responsive to the off-odor-causing substance, and the off-odor inhibitor contains one or more masking components selected from the group consisting of isoamyl cinnamate, cinnamyl cinnamate, δ-damascone, 2,3-heptanedione, carvacrol, vanitol, and 5-methyl-2-phenyl-2-hexenal. [2] The off-odor-causing substance is represented by the following formula (1) or (2): [In formula (1), R １ represents a hydrogen atom, an unbranched alkyl group having 1 to 3 carbon atoms, an alkyl group having 4 to 6 carbon atoms which may be branched, or an alkoxy group having 1 to 3 carbon atoms; R ２ and R ３ each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms which may be branched, or an alkoxy group having 1 to 3 carbon atoms, and in formula (2), R ４ and R ５each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms which may be branched, or an alkoxy group having 1 to 3 carbon atoms.] [3] The off-odor inhibitor according to [1] above, wherein the off-odor-causing substance comprises an off-odor substance generated in a food or beverage containing one or more compounds selected from the group consisting of aspartame, trans-2-hexenal, and hexanal. [4] The off-odor inhibitor according to any one of [1] to [3] above, wherein the off-odor-causing substance comprises one or more compounds selected from the group consisting of 3-ethyl-2-pentylpyridine, 2-sec-butyl-3-methoxypyrazine, 2-isobutyl-3-methoxypyrazine, 2-methoxy-3-isopropylpyrazine, and 2-isobutylpyridine. [5] The off-odor inhibitor according to any one of [1] to [4], wherein the off-odor is an off-odor that can be described as "dusty," and has at least one aroma characteristic selected from the group consisting of dusty, earthy, powdery, medicinal, and moldy, and contains as its main aroma note at least one expression selected from the group consisting of "dusty," "earthy," and "bell pepper-like or vegetable-like" as a descriptor for expressing the aroma characteristic, or a similar expression thereto, and is an off-odor that can be unpleasant to humans in some cases. [6] A fragrance composition for suppressing off-odors that masks off-odors contained in food and beverages, comprising the off-odor inhibitor according to any one of [1] to [5]. [7] A food and beverage containing the off-odor inhibitor according to any one of [1] to [5].

[0007] By using the off-odor suppressant of the present invention, it is possible to mask off-odors such as dusty odors contained in food and drink without impairing the flavor of the food and drink.

[0008]

[0033] Figure 1 shows the results of olfactory receptor screening for 2-isobutyl-3-methoxypyrazine. The responses of the olfactory receptor OR2AG2 to 1,367 odor compounds were screened, and the figures show the percentage of compounds that responded with a) a fold increase value of 3 or more to OR2AG2, and b) a fold increase value of 50 or more to OR2AG2, as well as the proportion of their main aroma notes.

[0034] Figure 1 shows the results of measuring the concentration-dependent responses of the olfactory receptor OR2AG2 to a) 3-ethyl-2-pentylpyridine (3E2P-pyridine), b) 2-methoxy-3-isopropylpyrazine (2M3IP-pyrazine), c) 2-isobutyl-3-methoxypyrazine (2IB3M-pyrazine), and d) 2-sec-butyl-3-methoxypyrazine (2sB3M-pyrazine).

[0009] Overview of the Invention In the present invention, the off-odor-causing substance contained in food or beverage is a substance responsive to at least one olfactory receptor polypeptide selected from the group consisting of olfactory receptor OR2AG2 and polypeptides that contain an amino acid sequence with 80% or more identity to the amino acid sequence of the olfactory receptor and that are responsive to off-odor-causing substances (hereinafter referred to as "olfactory receptor OR2AG2-responsive"). The responsiveness of an olfactory receptor polypeptide to an off-odor-causing substance refers to a change in responsiveness when comparing the basal activity response (T0) of the olfactory receptor polypeptide before exposure to the off-odor-causing substance with the response (Tx) of the olfactory receptor polypeptide to an off-odor at any time after exposure to the off-odor-causing substance. OR2AG2 is registered in GenBank as NM_001004490 and is a protein consisting of the amino acid sequence (SEQ ID NO: 2) encoded by DNA from positions 893 to 1843 of the base sequence set forth in SEQ ID NO: 1. The olfactory receptor polypeptide may be an olfactory receptor polypeptide selected from the group consisting of proteins (polypeptides) that contain an amino acid sequence that has 80% or more, preferably 85% or more, more preferably 90% or more, even more preferably 95% or more, and particularly preferably 98% or more identity to the amino acid sequence of OR2AG2 and that exhibits responsiveness to off-odor-causing substances. Note that, in this specification, the sequence identity of an amino acid sequence is calculated using the BLAST search algorithm (publicly available from NCBI).

[0010] To elucidate the chemical nature of the off-flavor described as "dusty" (or "earthy"), the present inventors screened 396 human olfactory receptors for 2-isobutyl-3-methoxypyrazine, a representative substance of "dusty" odors, and identified that 2-isobutyl-3-methoxypyrazine characteristically and strongly responds to the olfactory receptor OR2AG2 (Figure 1). Furthermore, the present inventors screened the responses of the olfactory receptor OR2AG2 to 1,367 odorants with various structures and aroma notes, and summarized the relationship between OR2AG2 responses and aroma notes. As a result, they obtained the novel findings that (i) many of the odorants that respond to OR2AG2 have the characteristics of a "dusty" odor, (ii) all of the odorants that respond particularly strongly are compounds with strong "dusty" odor characteristics, and in particular, (iii) a group of compounds represented by the following formula (1) or (2) show a strong response to OR2AG2 (Figures 2 and 3). [In formula (1), R １ represents a hydrogen atom, an unbranched alkyl group having 1 to 3 carbon atoms, an alkyl group having 4 to 6 carbon atoms which may be branched, or an alkoxy group having 1 to 3 carbon atoms; R ２ and R ３ each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms which may be branched, or an alkoxy group having 1 to 3 carbon atoms, and in formula (2), R ４ and R ５ each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms which may be branched, or an alkoxy group having 1 to 3 carbon atoms.

[0011] Here, examples of the alkyl group having 1 to 6 carbon atoms, which may be branched, include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, and 2-ethylbutyl. Among these, methyl, ethyl, isopropyl, isobutyl, sec-butyl, and n-pentyl are preferred. Examples of the unbranched alkyl group having 1 to 3 carbon atoms include methyl, ethyl, and propyl. Examples of the alkyl group having 4 to 6 carbon atoms, which may be branched, include n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, and 2-ethylbutyl. Examples of the alkoxy group having 1 to 3 carbon atoms include methoxy, ethoxy, propoxy, and isopropoxy.

[0012] The off-odor suppressant of the present invention is suitably used to mask off-odors caused by substances responsive to olfactory receptor OR2AG2 contained in foods and beverages.

[0013] Examples of masking components, which are the active ingredients of the off-odor suppressant used in the present invention, include isoamyl cinnamate, cinnamyl cinnamate, δ-damascone, 2,3-heptanedione, carvacrol, vanitol, and 5-methyl-2-phenyl-2-hexenal. These are all known fragrance components, and commercially available products can be used. Furthermore, some of these compounds exist as stereoisomers (cis-trans isomers, enantiomers, diastereomers, etc.), and specific stereoisomers can be used alone, or mixtures of these stereoisomers can be used. In the off-odor suppressant of the present invention, these masking components can be used alone or in combination of two or more.

[0014] The content of the masking component in the off-odor suppressant of the present invention is not particularly limited, but is preferably 70% by mass or more, more preferably 80% by mass or more, even more preferably 90% by mass or more, particularly preferably 95% by mass or more, even more preferably 99% by mass or more, and most preferably 99.5% by mass or more, and may be, for example, 99.8% by mass or more, 99.9% by mass or more, or may be 100% by mass when two or more masking components are used in combination. When two or more masking components are used in combination, the total amount thereof may be within the above range.

[0015] Any other component other than the masking component may be used as long as it does not impair the purpose and effects of the present invention, and is not particularly limited. Examples of the other components that can be used include various synthetic fragrances, natural fragrances, natural essential oils, plant extracts, solvents, and retention agents, as exemplified in the fragrance composition.

[0016] The off-odor inhibitor of the present invention can mask off-odors caused by substances responsive to the olfactory receptor OR2AG2 contained in foods and beverages, particularly off-odors described as "dusty." Here, "dusty" refers to an odor that is dusty and, in some cases, has at least one aroma characteristic selected from the group consisting of "earthy," "grassy," "powdery," "medicinal," and "moldy." The odor characteristic is expressed by a descriptor selected from the group consisting of "dusty," "earthy," and "grassy (bell pepper-like or vegetable-like)," or a similar description, and may, in some cases, be unpleasant to humans. The term "similar description" is not particularly limited, and may be any description that a person skilled in the art would recognize as a descriptor expressing the same aroma characteristic. For example, similar expressions to "earthy" include "galbanum" and "smoky." Furthermore, similar expressions to "bell pepper" or "vegetable" include "vegetable" and "bell pepper." According to this definition, for example, diosmin and 2-methylisoborneol, whose main aroma notes are described by the descriptor "musty" or "moldy," are not recognized as "dusty odors."

[0017] In the present invention, the off-odor-causing substances, particularly those that cause a "dusty odor," include compounds represented by the above formula (1) or (2), and may contain one or more of these pyridines or pyrazines. Specific examples include 2-isobutylpyridine, 2-sec-butyl-3-methoxypyrazine, 2-isobutyl-3-methoxypyrazine, 2-methoxy-3-isopropylpyrazine, and 3-ethyl-2-pentylpyridine. The off-odor suppressant of the present invention can mask the off-odor caused by one or more of these compounds contained in food or beverages.

[0018] Furthermore, in the present invention, the "dusty odor" may be a "dusty odor" consisting of a single substance that causes the "dusty odor," or may be a complex odor that has the "dusty odor," such as an extract of a fraction that has the "dusty odor." As long as a "dusty odor" is present, the substance that causes the "dusty odor" is necessarily contained; the substance that causes the "dusty odor" does not need to be identified. For example, the "dusty odor" may be a "dusty odor" caused by an off-flavor substance that occurs in a food or beverage containing one or more substances selected from the group consisting of aspartame, trans-2-hexenal, and hexanal, and the off-flavor substance does not need to be identified.

[0019] The fragrance composition of the present invention is a fragrance composition for suppressing off-odors that masks off-odors caused by substances responsive to the olfactory receptor OR2AG2 contained in foods and beverages, particularly off-odors described as "dusty odors," and contains the off-odor suppressant.

[0020] The content of the masking component in the flavor composition of the present invention is not particularly limited as long as it is an amount effective against off-flavors contained in foods and beverages, but is usually preferably 0.01 ppb or more and 100,000 ppm or less, and more preferably 0.1 ppb or more and 10,000 ppm or less, based on the mass of the flavor composition. When the content of the masking component is within the above range, it is possible to mask off-flavors contained in foods and beverages without affecting the flavor of the foods and beverages.

[0021] The flavor composition of the present invention can contain known flavors or conventional additives in a quantitative or qualitative range that does not impair the effects of the present invention, i.e., a range that can reduce the unpleasant odors present in foods and beverages. Examples of flavors that can be incorporated into the flavor composition of the present invention include various synthetic flavors, natural flavors, natural essential oils, and plant extracts, such as the natural essential oils, natural flavors, and synthetic flavors described in "Japan Patent Office Publication, Collection of Well-Known and Commonly Used Techniques (Fragrances) Part II Food Flavors, pp. 88-131, published January 14, 2000." Furthermore, the flavor composition of the present invention can optionally contain commonly used solvents such as water and ethanol; fixatives such as ethylene glycol, propylene glycol, dipropylene glycol, hexylene glycol, glycerin, triethyl citrate, medium-chain fatty acid triglycerides, medium-chain fatty acid diglycerides, and animal and vegetable oils and fats.

[0022] By incorporating the off-odor suppressant or fragrance composition of the present invention, it is possible to mask off-odors caused by substances responsive to the olfactory receptor OR2AG2 contained in foods and beverages, particularly off-odors described as "dusty odors." By including the masking component, it is possible to make off-odors contained in foods and beverages less noticeable.

[0023] The food and drink of the present invention is not particularly limited as long as it can contain the off-odor inhibitor or flavor composition of the present invention. Examples of the food and drink of the present invention include beverages such as fruit drinks, vegetable drinks, soft drinks, carbonated drinks, near water, functional drinks, health supplements, alcoholic beverages, non-alcoholic drinks, dairy drinks, and protein drinks; tea drinks and beverages such as black tea, green tea, oolong tea, herbal tea, coffee, and cocoa; plant-based alternative drinks such as soy milk drinks, oat milk drinks, and almond milk drinks; fermented dairy products such as yogurt and cheese; frozen desserts such as ice cream, lacto ice cream, ice milk, and ice cream; desserts such as pudding, jelly, bavarois, and mousse; and confectioneries such as chewing gum, candy, gummy candy, tablets, refreshing confectioneries, chocolate, chocolate confectioneries, and snacks. Examples of suitable food products include pastes and creams such as jam, dessert sauce, flour paste, margarine, fat spreads, filling cream, and whipped cream; agricultural foods and processed agricultural foods; meat and processed meat foods; fish and marine processed foods; dairy oil products; cooked rice products such as retort-pouched rice and germinated brown rice; noodles such as instant noodles, dried noodles, and chilled noodles; breads such as bread, meat buns, and prepared bread; soup foods; cooked and processed foods such as retort-pouched foods, pasta sauce, canned foods, and frozen and chilled foods; condiments such as sauces, soy sauce, dipping sauces, soups, mayonnaise, ketchup, dressings, tube products, dashi stock, Chinese seasonings, Western seasonings, and various rouxes; spices; edible oils and fats of animal or vegetable origin; and vegetable substitute foods. The flavor and fragrance composition of the present invention can also be used in oral products such as dentifrices, mouthwashes, mouthwashes, mouth sprays, and gargles; dishwashing detergents, etc.

[0024] The content of the masking component to be contained in the food or beverage of the present invention is not particularly limited as long as it is an amount effective against off-flavors contained in the food or beverage, but is preferably 10 ppt to 10 ppm, more preferably 100 ppt to 1 ppm, and even more preferably 1 ppb to 100 ppb, based on the mass of the food or beverage. Within the above ranges, the effect of masking off-flavors contained in the food or beverage can be obtained without affecting the flavor of the food or beverage.

[0025] In one aspect, the present invention provides a method for producing a food or beverage, comprising adding one or more masking components selected from the group consisting of isoamyl cinnamate, cinnamyl cinnamate, δ-damascone, 2,3-heptanedione, carvacrol, vanitol, and 5-methyl-2-phenyl-2-hexenal to the food or beverage. The content of the masking component contained in the food or beverage is preferably 10 ppt to 10 ppm, more preferably 100 ppt to 1 ppm, and even more preferably 1 ppb to 100 ppb, based on the mass of the food or beverage. The masking components may be used alone or in combination of two or more. When two or more masking components are used, it is sufficient that the total concentration range satisfies the above range. The timing of adding the masking component is not particularly limited. It is preferable to add the masking component in a manner that does not impair the masking effect.

[0026] In another aspect, the present invention provides a method for masking a food or beverage, which comprises adding one or more components selected from the group consisting of isoamyl cinnamate, cinnamyl cinnamate, δ-damascone, 2,3-heptanedione, carvacrol, vanitol, and 5-methyl-2-phenyl-2-hexenal to the food or beverage. The amount of the masking component used and the timing of addition are the same as those described in the method for producing the food or beverage.

[0027] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples in any way.

[0028] Reference Example 1 Identification of Olfactory Receptors Responding to 2-Isobutyl-3-Methoxypyrazine, a Representative Substance of "Dusty Odor" (1-1) Cloning of Olfactory Receptor Genes Human olfactory receptor genes were obtained by PCR cloning from Human Genomic DNA: Female (Promega) based on the base sequence information (see SEQ ID NO: 1) registered on the NCBI (GenBank) website. DNA encoding the N-terminal 20 amino acid residues of bovine rhodopsin (DNA consisting of bases 1 to 60 of the base sequence of SEQ ID NO: 3) was inserted into the pME18S vector, and the resulting human olfactory receptor gene was inserted downstream to obtain a human olfactory receptor gene expression vector. Bovine rhodopsin is registered on the NCBI (GenBank) website under "Accession number: NM_001014890.2" and "Accession number: NP_001014890.1." Bovine rhodopsin is a protein (polypeptide) consisting of an amino acid sequence (SEQ ID NO: 4) encoded by the DNA from the 1st to 1047th bases of the base sequence shown in SEQ ID NO: 3.

[0029] (1-2) Expression of Olfactory Receptor Genes in HEK293T Cells 0.05 μg of human olfactory receptor gene expression vector, 0.01 μg of RTP1S vector, 0.01 μg of firefly luciferase vector pGL4.29 (Promega) containing a cAMP response element promoter, and 0.005 μg of Renilla luciferase vector pGL4.74 (Promega) containing a thymidine kinase promoter were dissolved in 10 μL of Opti-MEM I (Gibco) to prepare a gene solution (for one well). HEK293T cells were seeded in 96-well plates (Biocoat, Corning) at a cell number that would reach confluence after 24 hours, each in an amount of 100 μL. The gene solution was added to each well by lipofection according to the instructions for Lipofectamine 3000, thereby transfecting the cells. The cells were then cultured at 37°C in a 5% carbon dioxide atmosphere for 24 hours.

[0030] (1-3) Luciferase Reporter Gene Assay After removing the culture medium, 60 μL of a sample aroma compound prepared in CD293 (Gibco) medium (supplemented with 20 μM L-glutamine) at a concentration suitable for measurement was added to each well. After 3 hours of stimulation, luciferase activity was measured according to the instructions for the Dual-Luciferase Reporter Assay System (Promega). The response intensity of the olfactory receptor was measured using the fold increase value, which was calculated by dividing the luciferase activity generated by stimulation with an aroma compound by the luciferase activity generated in a test system without the aroma compound.

[0031] (1-4) Olfactory Receptor Screening with 2-Isobutyl-3-Methoxypyrazine Based on the above (1-1) to (1-3), HEK293 cells expressing each of the 396 human olfactory receptors were prepared, and the response of each of the 396 olfactory receptors was calculated as a fold increase value by adding 1 mM 2-isobutyl-3-methoxypyrazine. The results are shown in Figure 1.

[0032] Reference Example 2: Proof that the olfactory receptor OR2AG2 is an odor note-specific receptor for substances that cause "dusty odors" (2-1) Screening of odorants that respond to OR2AG2 A human olfactory receptor OR2AG2 gene expression vector was cloned, and the olfactory receptor OR2AG2 gene was expressed in HEK293T cells. A total of 1,367 odorants were added to the cells at the maximum appropriate concentration within the final concentration range of 1 μM to 1 mM that did not cause cell damage, and a luciferase reporter gene assay was performed. All 1,367 odorants used were assigned odor note information by an odor expert. For odorants that showed a response value above a predetermined level in the luciferase reporter gene assay, the main odor note in the odor note information was extracted, and the proportion of each odor note was determined. The results are shown in Figure 2.

[0033] (2-2) Confirmation that "dusty odor" compounds respond to OR2AG2 in a concentration-dependent manner. The human olfactory receptor OR2AG2 gene expression vector was cloned, and the olfactory receptor OR2AG2 gene was expressed in HEK293T cells. Representative odorants with a "dusty odor," which are OR2AG2-responsive compounds shown in Figure 2, were added to the cells to final concentrations of 3 μM, 10 μM, 30 μM, 100 μM, 300 μM, and 700 μM, and a luciferase reporter gene assay was performed. The results are shown in Figure 3.

[0034] Example 1 Masking Effect of Isoamyl Cinnamate on Off-Odor Due to Dust Odor in Water 3-Ethyl-2-pentylpyridine was added to ion-exchanged water to a concentration of 0.1 ppm to prepare an aqueous solution containing off-flavor components. Isoamyl cinnamate was added to this off-flavor component-containing aqueous solution at the concentration shown in Table 1, and the intensity of the off-flavor (masking effect) of each sample and the intensity of the masking component itself (the effect on the flavor of the food or beverage itself) were confirmed. The test was performed by a sensory evaluation conducted by six skilled panelists. The off-odor intensity of the off-flavor component-containing aqueous solution to which no masking component had been added was rated "Rating: 4," and ion-exchanged water not containing the off-flavor component was rated "Rating: 0," and the off-odor intensity (masking effect) of each sample was relatively rated according to the following evaluation criteria. <Evaluation criteria> Strong off-flavor: 4 points Off-flavor: 3 points Slight off-flavor: 2 points Barely any off-flavor: 1 point No off-flavor: 0 point Furthermore, the strength of the masking ingredients (impact on the flavor of the food or drink itself) was evaluated in absolute terms according to the following evaluation criteria: <Evaluation criteria> Strongly detectable masking ingredient: 4 points Masking ingredient: 3 points Slightly detectable masking ingredient: 2 points Barely detectable masking ingredient: 1 point No masking ingredient: 0 point The results are shown in Table 1, which shows the average score of the evaluation results of each panel.

[0035] The masking effect of isoamyl cinnamate was confirmed from the results in Table 1. In particular, it is clear that isoamyl cinnamate masks the off-odor caused by 3-ethyl-2-pentylpyridine at a concentration of 1 ppb or more and 10 ppm or less, without affecting the flavor of the food or drink itself.

[0036] [Example 2] Masking effect of cinnamyl cinnamate on off-flavor components consisting of dusty odors in water The intensity of the off-flavor (masking effect) of each sample and the intensity of the masking component itself (impact on the flavor of the food or beverage itself) were confirmed in the same manner as in Example 1, except that cinnamyl cinnamate was added as the masking component at the concentration shown in Table 2. The results are shown in Table 2, which shows the average score of the evaluation results of each panel.

[0037] The masking effect of cinnamyl cinnamate was confirmed from the results in Table 2. In particular, it is clear that cinnamyl cinnamate masks the off-odor caused by 3-ethyl-2-pentylpyridine at a concentration of 10 ppb or more and 10 ppm or less, and does not affect the flavor of the food or drink itself.

[0038] Example 3 Masking effect of δ-damascone on off-flavor components consisting of dusty odors in water The intensity of the off-flavor (masking effect) of each sample and the strength of the masking component itself (impact on the flavor of the food or beverage itself) were confirmed in the same manner as in Example 1, except that δ-damascone was added as the masking component at the concentration shown in Table 3. The results are shown in Table 3, which shows the average score of the evaluation results of each panel.

[0039] The masking effect of δ-damascone was confirmed from the results in Table 3. In particular, it is clear that δ-damascone masks the off-flavor of 3-ethyl-2-pentylpyridine at a concentration of 100 ppt or more and 100 ppb or less, without affecting the flavor of the food or drink itself.

[0040] Example 4 Masking Effect of 2,3-Heptanedione on Off-Flavor Components Consisting of Dust Odors in Water The intensity of the off-flavor (masking effect) of each sample and the intensity of the masking component itself (impact on the flavor of the food or beverage itself) were confirmed in the same manner as in Example 1, except that 2,3-heptanedione was added as the masking component at the concentration shown in Table 4. The results are shown in Table 4, which shows the average score of the evaluation results from each panel.

[0041] The masking effect of 2,3-heptanedione was confirmed from the results in Table 4. In particular, it is clear that 2,3-heptanedione at a concentration of 1 ppb or more and 100 ppb or less masks the off-flavor of 3-ethyl-2-pentylpyridine without affecting the flavor of the food or drink itself.

[0042] Example 5 Masking Effect of Carvacrol on Off-Flavor Components Consisting of Dust Odors in Water The intensity of the off-flavor (masking effect) of each sample and the intensity of the masking component itself (impact on the flavor of the food or beverage itself) were confirmed in the same manner as in Example 1, except that carvacrol was added as the masking component at the concentrations shown in Table 5. The results are shown in Table 5, which shows the average scores of the evaluation results from each panel.

[0043] The masking effect of carvacrol was confirmed from the results in Table 5. In particular, it is clear that carvacrol masks the off-odor caused by 3-ethyl-2-pentylpyridine at a concentration of 1 ppb or more and 100 ppb or less, without affecting the flavor of the food or drink itself.

[0044] Example 6 Masking Effect of Vanitol on Off-Flavor Components Consisting of Dust Odors in Water The intensity of the off-flavor (masking effect) of each sample and the strength of the masking component itself (impact on the flavor of the food or drink itself) were confirmed in the same manner as in Example 1, except that vanitol was added as the masking component at the concentrations shown in Table 6. The results are shown in Table 6, which shows the average scores of the evaluation results from each panel.

[0045] The masking effect of vanitol was confirmed from the results in Table 6. In particular, it is clear that vanitol masks the off-odor caused by 3-ethyl-2-pentylpyridine at a concentration of 10 ppb or more and 1 ppm or less, without affecting the flavor of the food or drink itself.

[0046] Example 7 Masking Effect of 5-methyl-2-phenyl-2-hexenal on Off-Flavor Components Consisting of Dust Odors in Water The intensity of the off-flavor (masking effect) of each sample and the intensity of the masking component itself (the effect on the flavor of the food or beverage itself) were confirmed in the same manner as in Example 1, except that 5-methyl-2-phenyl-2-hexenal was added as the masking component at the concentration shown in Table 7. The results are shown in Table 7, which shows the average score of the evaluation results of each panel.

[0047] The masking effect of 5-methyl-2-phenyl-2-hexenal was confirmed from the results in Table 7. In particular, it is clear that 5-methyl-2-phenyl-2-hexenal masks the off-odor caused by 3-ethyl-2-pentylpyridine at a concentration of 1 ppb or more and 1 ppm or less, without affecting the flavor of the food or beverage itself.

[0048] Example 8 Masking Effect of Cinnamyl Cinnamate on Off-Odor Components Consisting of Dust Odors in Water 2-Isobutylpyridine was added to ion-exchanged water to a concentration of 0.1 ppm to prepare an aqueous solution containing off-odor components. Cinnamyl cinnamate was added to this aqueous solution containing off-odor components at the concentrations shown in Table 8, and the strength of the off-flavor (masking effect) of each sample and the strength of the masking component itself (impact on the flavor of the food or beverage itself) were confirmed in the same manner as in Example 1. The results are shown in Table 8, which shows the average score of the evaluation results of each panel.

[0049] The masking effect of cinnamyl cinnamate was confirmed from the results in Table 8. In particular, it is clear that cinnamyl cinnamate masks the unpleasant odor caused by 2-isobutylpyridine at a concentration of 1 ppb or more and 1 ppm or less, and does not affect the flavor of the food or drink itself.

[0050] Example 9 Masking Effect of Cinnamyl Cinnamate on Off-Odor Components Consisting of Dust Odors in Water 2-Isobutyl-3-methoxypyrazine was added to ion-exchanged water to a concentration of 0.1 ppm to prepare an aqueous solution containing off-odor components. Cinnamyl cinnamate was added to this aqueous solution containing off-odor components at the concentrations shown in Table 9, and the strength of the off-flavor (masking effect) of each sample and the strength of the masking component itself (impact on the flavor of the food or beverage itself) were confirmed in the same manner as in Example 1. The results are shown in Table 9, which shows the average score of the evaluation results of each panel.

[0051] The masking effect of cinnamyl cinnamate was confirmed from the results in Table 9. In particular, it is clear that cinnamyl cinnamate masks the unpleasant odor caused by 2-isobutyl-3-methoxypyrazine at a concentration of 10 ppb or more and 100 ppb or less, and does not affect the flavor of the food or drink itself.

[0052] Example 10 Masking Effect of Cinnamyl Cinnamate on Off-Odor Components Consisting of Dust Odors in Water 2-sec-butyl-3-methoxypyrazine was added to ion-exchanged water to a concentration of 0.1 ppm to prepare an aqueous solution containing off-odor components. Cinnamyl cinnamate was added to this aqueous solution containing off-odor components at the concentrations shown in Table 10, and the strength of the off-flavor (masking effect) of each sample and the strength of the masking component itself (impact on the flavor of the food or beverage itself) were confirmed in the same manner as in Example 1. The results are shown in Table 10, which shows the average score of the evaluation results of each panel.

[0053] The masking effect of cinnamyl cinnamate was confirmed from the results in Table 10. In particular, it is clear that cinnamyl cinnamate masks the unpleasant odor caused by 2-sec-butyl-3-methoxypyrazine at a concentration of 100 ppb or more and 1 ppm or less, and does not affect the flavor of the food or drink itself.

[0054] Example 11 Masking Effect of Cinnamyl Cinnamate on Off-Odor Components Consisting of Dust Odors in Water 2-Methoxy-3-isopropylpyrazine was added to ion-exchanged water to a concentration of 0.1 ppm to prepare an aqueous solution containing off-odor components. Cinnamyl cinnamate was added to this aqueous solution containing off-odor components at the concentrations shown in Table 11, and the strength of the off-flavor (masking effect) of each sample and the strength of the masking component itself (the effect on the flavor of the food or beverage itself) were confirmed in the same manner as in Example 1. The results are shown in Table 11, which shows the average score of the evaluation results of each panel.

[0055] The masking effect of cinnamyl cinnamate was confirmed from the results in Table 11. In particular, it is clear that cinnamyl cinnamate masks the off-odor caused by 2-methoxy-3-isopropylpyrazine at a concentration of 1 ppb or more and 1 ppm or less, and does not affect the flavor of the food or drink itself.

[0056] Example 12 Masking Effect of Cinnamyl Cinnamate on Off-Odor Components Consisting of Dusty Odors in Soy Milk 2-Methoxy-3-isopropylpyrazine was added to commercially available soy milk to a concentration of 100 ppt to prepare soy milk containing off-odor components. Cinnamyl cinnamate was added to this off-odor component-containing soy milk at the concentrations shown in Table 12, and the strength of the off-flavor (masking effect) of each sample and the strength of the masking component itself (impact on the flavor of the food or beverage itself) were confirmed using the same evaluation method as in Example 1. The results are shown in Table 12, which shows the average score of the evaluation results from each panel.

[0057] The masking effect of cinnamyl cinnamate was confirmed from the results in Table 12. In particular, it is clear that cinnamyl cinnamate masks the off-odor caused by 2-methoxy-3-isopropylpyrazine at a concentration of 10 ppb or more and 1 ppm or less, and does not affect the flavor of the food or drink itself.

[0058] Example 13 Masking Effect of 5-Methyl-2-phenyl-2-hexenal on Off-Odor Components Consisting of Dusty Odors in Soy Milk 2-Methoxy-3-isopropylpyrazine was added to commercially available soy milk to a concentration of 1 ppb to prepare soy milk containing off-odor components. 5-Methyl-2-phenyl-2-hexenal was added to this off-odor component-containing soy milk at the concentrations shown in Table 13, and the intensity of the off-flavor (masking effect) of each sample and the intensity of the masking component itself (impact on the flavor of the food or beverage itself) were confirmed in the same manner as in Example 12. The results are shown in Table 13, which shows the average score of the evaluation results from each panel.

[0059] The masking effect of 5-methyl-2-phenyl-2-hexenal was confirmed from the results in Table 13. In particular, it is clear that 5-methyl-2-phenyl-2-hexenal masks the unpleasant odor caused by 2-methoxy-3-isopropylpyrazine at a concentration of 100 ppb or more and 1 ppm or less, and does not affect the flavor of the food or beverage itself.

[0060] Example 14 Masking Effect of δ-Damascone on Off-Flavor Components Consisting of Dusty Odors in Soy Milk 2-Methoxy-3-isopropylpyrazine was added to commercially available soy milk to a concentration of 100 ppt to prepare soy milk containing off-flavor components, to which δ-damascone was added at the concentrations shown in Table 14. The strength of the off-flavor (masking effect) of each sample and the strength of the masking component itself (the effect on the flavor of the food or drink itself) were confirmed in the same manner as in Example 12. The results are shown in Table 14, which shows the average score of the evaluation results of each panel.

[0061] The masking effect of δ-damascone was confirmed from the results in Table 14. In particular, it is clear that δ-damascone masks 2-methoxy-3-isopropylpyrazine at a concentration of 1 ppb or more and 10 ppb or less, without affecting the flavor of the food or drink itself.

[0062] Example 15 Masking Effect of Vanitol on Off-Odor Components Consisting of Dust Odors in Coffee A diluted coffee solution was prepared by dissolving 2 g of commercially available instant coffee in 140 g of water. 2-Methoxy-3-isopropylpyrazine was added to this diluted coffee solution to a concentration of 100 ppt, preparing a diluted coffee solution containing off-odor components. Vanitol was added to this diluted coffee solution containing off-odor components at the concentrations shown in Table 15, and the intensity of the off-flavor (masking effect) of each sample and the intensity of the masking components themselves (the effect on the flavor of the food or beverage itself) were evaluated using the same evaluation method as in Example 1. The results are shown in Table 15, which shows the average score of the evaluation results from each panel.

[0063] The masking effect of vanitol was confirmed from the results in Table 15. In particular, it is clear that vanitol masks the off-odor caused by 2-methoxy-3-isopropylpyrazine at a concentration of 10 ppb or more and 100 ppb or less, without affecting the flavor of the food or drink itself.

[0064] Example 16 Masking Effect of Carvacrol on Off-Odor Components Consisting of Dust Odors in Coffee A diluted coffee solution containing off-odor components similar to that in Example 15 was prepared, and carvacrol was added at the concentrations shown in Table 16. The strength of the off-flavor (masking effect) of each sample and the strength of the masking components themselves (the effect on the flavor of the food or beverage itself) were confirmed in the same manner as in Example 15. The results are shown in Table 16, which shows the average scores of the evaluation results of each panel.

[0065] The masking effect of carvacrol was confirmed from the results in Table 16. In particular, it is clear that carvacrol masks the off-odor caused by 2-methoxy-3-isopropylpyrazine at a concentration of 1 ppb or more and 10 ppb or less, without affecting the flavor of the food or drink itself.

[0066] Example 17 Masking Effect of Isoamyl Cinnamate on Off-Odor Components Consisting of Dust Odors in Vegetable Juice 2-Methoxy-3-isopropylpyrazine was added to a commercially available vegetable juice to a concentration of 1 ppb to prepare a vegetable juice containing off-odor components. Isoamyl cinnamate was added to this vegetable juice containing off-odor components at the concentrations shown in Table 17, and the strength of the off-flavor (masking effect) of each sample and the strength of the masking component itself (impact on the flavor of the food or beverage itself) were confirmed using the same evaluation method as in Example 1. The results are shown in Table 17, which shows the average score of the evaluation results from each panel.

[0067] The masking effect of isoamyl cinnamate was confirmed from the results in Table 17. In particular, it is clear that isoamyl cinnamate masks the off-odor caused by 2-methoxy-3-isopropylpyrazine at a concentration of 1 ppb or more and 1 ppm or less, without affecting the flavor of the food or drink itself.

[0068] [Example 18] Masking effect of cinnamyl cinnamate on off-flavor components consisting of dusty odor in vegetable juice Cinnamyl cinnamate was added at the concentrations shown in Table 18, and the strength of the off-flavor (masking effect) of each sample and the strength of the masking component itself (the effect on the flavor of the food or beverage itself) were confirmed in the same manner as in Example 17. The results are shown in Table 18, which shows the average score of the evaluation results of each panel.

[0069] The masking effect of cinnamyl cinnamate was confirmed from the results in Table 18. In particular, it is clear that cinnamyl cinnamate masks 2-methoxy-3-isopropylpyrazine at a concentration of 100 ppt or more and 100 ppb or less, and does not affect the flavor of the food or drink itself.

[0070] Example 19 Masking Effect of δ-Damascone on Off-Flavor Components Consisting of Dust Odors in Vegetable Juice δ-Damascone was added at the concentrations shown in Table 19, and the strength of the off-flavor (masking effect) of each sample and the strength of the masking component itself (the effect on the flavor of the food or drink itself) were confirmed in the same manner as in Example 17. The results are shown in Table 19, which shows the average score of the evaluation results of each panel.

[0071] The masking effect of δ-damascone was confirmed from the results in Table 19. In particular, it is clear that δ-damascone masks 2-methoxy-3-isopropylpyrazine at a concentration of 100 ppt or more and 10 ppb or less, without affecting the flavor of the food or drink itself.

[0072] Example 20 Masking Effect of 2,3-Heptanedione on Off-Flavor Components Consisting of Dust Odors in Vegetable Juice 2,3-Heptanedione was added at the concentrations shown in Table 20, and the strength of the off-flavor (masking effect) of each sample and the strength of the masking component itself (the effect on the flavor of the food or beverage itself) were confirmed in the same manner as in Example 17. The results are shown in Table 20, which shows the average scores of the evaluation results from each panel.

[0073] The masking effect of 2,3-heptanedione was confirmed from the results in Table 20. In particular, it is clear that 2,3-heptanedione at a concentration of about 10 ppb masks the off-odor caused by 2-methoxy-3-isopropylpyrazine without affecting the flavor of the food or drink itself.

[0074] Example 21 Masking Effect of Carvacrol on Off-Flavor Components Consisting of Dust Odors in Vegetable Juice Carvacrol was added at the concentrations shown in Table 21, and the strength of the off-flavor (masking effect) of each sample and the strength of the masking components themselves (the effect on the flavor of the food or beverage itself) were confirmed in the same manner as in Example 17. The results are shown in Table 21, which shows the average scores of the evaluation results of each panel.

[0075] The masking effect of carvacrol was confirmed from the results in Table 21. In particular, it is clear that carvacrol masks 2-methoxy-3-isopropylpyrazine at a concentration of 100 ppt or more and 100 ppb or less, without affecting the flavor of the food or drink itself.

[0076] Example 22 Masking effect of vanitol on off-flavor components consisting of dusty odors in vegetable juice Vanitol was added at the concentrations shown in Table 22, and the strength of the off-flavor (masking effect) of each sample and the strength of the masking components themselves (the effect on the flavor of the food or drink itself) were confirmed in the same manner as in Example 17. The results are shown in Table 22, which shows the average scores of the evaluation results of each panel.

[0077] The masking effect of vanitol was confirmed from the results in Table 22. In particular, it is clear that vanitol masks 2-methoxy-3-isopropylpyrazine at a concentration of 10 ppb or more and 1 ppm or less, without affecting the flavor of the food or drink itself.

[0078] Example 23 Masking Effect of 5-Methyl-2-phenyl-2-hexenal on Off-Flavor Components Consisting of Dust Odors in Vegetable Juice 5-Methyl-2-phenyl-2-hexenal was added at the concentrations shown in Table 23, and the strength of the off-flavor (masking effect) of each sample and the strength of the masking component itself (the effect on the flavor of the food or beverage itself) were confirmed in the same manner as in Example 17. The results are shown in Table 23, which shows the average score of the evaluation results of each panel.

[0079] The results in Table 23 demonstrate the masking effect of 5-methyl-2-phenyl-2-hexenal. It is clear that 5-methyl-2-phenyl-2-hexenal masks the unpleasant odor caused by 2-methoxy-3-isopropylpyrazine at a concentration of 1 ppb or more and 1 ppm or less, without affecting the flavor of the food or drink itself.

[0080] Example 24: Masking effect of cinnamyl cinnamate on off-flavor components consisting of dust odor in tablet confectionery. Tablet confectionery was prepared according to the recipe in Table 24 using a 7 mm diameter mortar and pestle, and 100 ppm each of hexanal and trans-2-hexenal were added. Cinnamyl cinnamate was added to these tablet confectionery at the concentrations listed in Table 25, and the tablets were left to stand at 40°C for two weeks to produce abused tablet confectionery. The strength of the off-flavor (masking effect) of each sample of these abused tablet confectionery and the strength of the masking component itself (impact on the flavor of the food or beverage itself) were confirmed in the same manner as in Example 1. The results are shown in Table 25, which shows the average score of the evaluation results of each panel.

[0081]

[0082] From the results in Table 25, it is clear that cinnamyl cinnamate at a concentration of 1 ppb or more and 100 ppb or less masks the unpleasant odor caused by abuse of the tablets, and does not affect the flavor of the food or beverage itself.

Claims

1. An off-odor inhibitor that masks off-odors contained in food and beverages, wherein the off-odor causative substance is at least one olfactory receptor polypeptide responsive substance selected from the group consisting of olfactory receptor OR2AG2 and polypeptides that contain an amino acid sequence that has 80% or more identity with the amino acid sequence of the olfactory receptor and are responsive to off-odor causative substances, and the off-odor inhibitor contains one or more masking components selected from the group consisting of isoamyl cinnamate, cinnamyl cinnamate, δ-damascone, 2,3-heptanedione, carvacrol, vanitol, and 5-methyl-2-phenyl-2-hexenal.

2. The substance causing the off-flavor is represented by the following formula (1) or (2): [In formula (1), R １ represents a hydrogen atom, an unbranched alkyl group having 1 to 3 carbon atoms, an alkyl group which may be branched having 4 to 6 carbon atoms, or an alkoxy group having 1 to 3 carbon atoms; R ２ and R ３ each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms which may be branched, or an alkoxy group having 1 to 3 carbon atoms; ４ and R ５ each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms which may be branched, or an alkoxy group having 1 to 3 carbon atoms.

3. The off-odor suppressant according to claim 1, wherein the off-odor-causing substance comprises an off-odor substance generated in food or beverages, the off-odor substance including one or more substances selected from the group consisting of aspartame, trans-2-hexenal, and hexanal.

4. The off-odor inhibitor according to claim 1, wherein the off-odor causative substance comprises one or more selected from the group consisting of 3-ethyl-2-pentylpyridine, 2-sec-butyl-3-methoxypyrazine, 2-isobutyl-3-methoxypyrazine, 2-methoxy-3-isopropylpyrazine, and 2-isobutylpyridine.

5. The off-odor suppressant according to claim 1, wherein the off-odor is an off-odor that can be expressed as a "dusty odor", has at least one odor characteristic selected from the group consisting of dusty, earthy, powdery, medicinal and moldy, and contains at least one main odor note selected from the group consisting of "dusty", "earthy" and "bell pepper" or "vegetable" as a descriptor expressing the odor characteristic, or a similar expression thereto, and is an odor that can be unpleasant to humans in some cases.

6. A fragrance composition for suppressing off-odors, which comprises the off-odor suppressant according to any one of claims 1 to 5 and masks off-odors contained in food and beverages.

7. A food or drink comprising the odor suppressant according to any one of claims 1 to 5.

Images