Flavoring composition and food and drink

Abstract

The purpose of the present invention is to provide a method for obscuring (masking) the odor of p-cresol using olfactory receptor antagonism without affecting the flavor of a food or beverage. The present invention uses a specific concentration of ambrettolide, isoambrettolide, pentalide, muscone, civetone, δ-2-decenolactone, cinnamic aldehyde, β-caryophyllene oxide, sclareolide, and ethyl maltol in a food or beverage.

Description

[Technical Field]

[0001] The present invention relates to a food or drink having the flavor of citrus fruits or ginger, and more particularly to a food or drink in which the off-flavor caused by the deterioration of aroma components of citrus fruits or ginger is masked. [Background technology]

[0002] Foods and beverages with citrus fruit flavors are popular with many people because they combine a moderate sweet and sour taste with the refreshing aroma unique to citrus fruits, creating a uniquely refreshing feeling. Ginger, with its sweet and refreshing aroma and refreshing spiciness, has been widely used since ancient times to eliminate the odor of meat and fish and to impart a unique flavor to foods and beverages. However, it is known that the refreshing aroma unique to citrus fruits or ginger is lost over time, resulting in a deterioration odor (off-flavor), which deteriorates the quality of the food and beverages. Citral is an important aroma component found widely in citrus fruits and ginger, and has a characteristic lemon-like aroma. However, it is known that citral decreases with heating or over time, resulting in the formation of a stale odor. p-Cresol is known to be one of the substances causing the stale odor. As a method for masking deterioration odors, Patent Document 1 describes a method in which a specific amount of cineole or cis-3-hexenol is added, and Patent Document 2 describes a method in which one or more compounds selected from the group consisting of ethyl pyruvate, methyl jasmonate, methyl dihydrojasmonate, diethyl malonate, methyl beta naphthyl ketone, maltol isobutyrate, menthol, lauric acid, acetoin, cinnamyl acetate, benzyl acetate, and α-terpineol are added. Ambrettolide, isoambrettolide, cyclopentadecanolide, civetone, muscone, δ-2-decenolactone, ethyl maltol, cinnamic aldehyde, β-caryophyllene oxide, and the like are known to be used in hair cosmetic masking compositions that mask unpleasant odors such as base odor, amine odor, ammonia odor, sulfur odor, acid odor, rust odor, tobacco odor, animal odor, and halogen odor (Patent Document 3). Sclareolide is known to be used as a fragrance / flavor imparting or modulating agent in oral flavor compositions (Patent Document 4). β-caryophyllene oxide is known to be used as a fragrance / flavor imparting or modulating agent in citrus-like flavor compositions (Patent Document 5). Ethyl maltol and the like are known to reduce the perceived stale odor of fruit flavors in clear beverages containing fruit flavors (Patent Document 6). Meanwhile, in the field of cosmetics, a method for suppressing urine odor has been provided by specifically inhibiting the activity of the olfactory receptor OR9Q2 for p-cresol (Patent Document 7). [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Application Laid-Open No. 2016-36319 [Patent Document 2] Japanese Patent Application Laid-Open No. 2015-180715 [Patent Document 3] Japanese Patent Application Laid-Open No. 2003-137758 [Patent Document 4] Japanese Patent Application Laid-Open No. 2004-18431 [Patent Document 5] Japanese Patent Application Laid-Open No. 2004-168936 [Patent Document 6] Japanese Patent Application Laid-Open No. 2016-127818 [Patent Document 7] Japanese Patent Application Laid-Open No. 2017-101224 Summary of the Invention [Problem to be solved by the invention]

[0004] The present invention relates to providing a method for making the p-cresol odor less noticeable (masking) without affecting the flavor of citrus-flavored or ginger-flavored foods and beverages. [Means for solving the problem]

[0005] The present inventors utilized olfactory receptor antagonism and discovered that among the antagonists of the olfactory receptor OR9Q2 for p-cresol, ambrettolide, isoambrettolide, pentalide, muscone, civetone, δ-2-decenolactone, cinnamic aldehyde, β-caryophyllene oxide, sclareolide, and ethyl maltol suppress the p-cresol odor at specific concentrations in citrus-flavored beverages without impairing the flavor of the product. The present invention includes the following contents [1] to

[11] . [1] A method for masking the deterioration odor of citral or a citral-containing product, characterized by adding one or more selected from the group consisting of ambrettolide, isoambrettolide, pentalide, muscone, civetone, δ-2-decenolactone, cinnamic aldehyde, β-caryophyllene oxide, sclareolide, and ethyl maltol to the citral-containing product. [2] The masking method according to [1] above, wherein the deterioration odor is p-cresol. [3] The masking method according to either [1] or [2], wherein the citral-containing product is a citrus-flavored food or drink or a ginger-flavored food or drink. [4] A fragrance composition for masking the deterioration odor of citral-containing products, characterized by containing one or more members selected from the group consisting of ambrettolide, isoambrettolide, pentalide, muscone, civetone, δ-2-decenolactone, cinnamic aldehyde, β-caryophyllene oxide, sclareolide, and ethyl maltol. [5] The fragrance composition according to [4], which is citrus-like or ginger-like. [6] The fragrance composition according to either [4] or [5] above, wherein the deterioration odor is p-cresol. [7] The flavor composition according to any one of [4] to [6] above, wherein the citral-containing product is a citrus-flavored food or drink or a ginger-flavored food or drink. [8] A citral-containing product containing 0.01 ppt to 10 ppm of one or more selected from the group consisting of ambrettolide, isoambrettolide, pentalide, muscone, civetone, δ-2-decenolactone, cinnamic aldehyde, β-caryophyllene oxide, sclareolide, and ethyl maltol. [9] The product described in [8] above, wherein the citral-containing product is a citrus-flavored food or beverage or a ginger-flavored food or beverage.

[10] The product according to either [8] or [9] above, containing 10 ppb to 1 ppm of p-cresol.

[11] A method for producing a citral-containing product, characterized by blending 0.01 ppt to 10 ppm of one or more selected from the group consisting of ambrettolide, isoambrettolide, pentalide, muscone, civetone, δ-2-decenolactone, cinnamic aldehyde, β-caryophyllene oxide, sclareolide, and ethyl maltol into the citral-containing product. [Effects of the Invention]

[0006] According to the present invention, by adding a specific amount of one or more compounds selected from the group consisting of ambrettolide, isoambrettolide, pentalide, muscone, civetone, δ-2-decenolactone, cinnamic aldehyde, β-caryophyllene oxide, sclareolide, and ethyl maltol to a citrus-flavored food or beverage or a ginger-flavored food or beverage, it is possible to mask the stagnant odor caused by the deterioration of citrus fruit or ginger aroma components.As a result, even in foods and beverages containing citrus fruit or ginger aroma components that are prone to deterioration and that develop deteriorated components after long-term storage, it is possible to provide foods and beverages that have a citrus fruit or ginger aroma that is closer to the design immediately after production. [Brief explanation of the drawings]

[0007] [Figure 1]FIG. 1 shows the results of the response-suppressing effect of the olfactory receptor OR9Q2 to p-cresol by the addition of 1-oxacycloheptadecan-7-en-2-one. [Figure 2] FIG. 1 shows the results of the response-suppressing effect of the olfactory receptor OR9Q2 to p-cresol by the addition of 1-oxacycloheptadecan-8-en-2-one. [Figure 3] FIG. 1 shows the results of the response-suppressing effect of the olfactory receptor OR9Q2 to p-cresol by the addition of isoambrettolide. [Figure 4] FIG. 1 shows the results of the response-suppressing effect of olfactory receptor OR9Q2 to p-cresol by the addition of muscone. [Figure 5] FIG. 1 shows the results of the response-suppressing effect of olfactory receptor OR9Q2 to p-cresol by the addition of civetone. [Figure 6] FIG. 1 shows the results of the response-suppressing effect of olfactory receptor OR9Q2 to p-cresol by the addition of pentalide. [Figure 7] FIG. 1 shows the results of the response-suppressing effect of olfactory receptor OR9Q2 to p-cresol by the addition of delta-2-decenolactone. [Figure 8] FIG. 1 shows the results of the response-suppressing effect of olfactory receptor OR9Q2 to p-cresol by the addition of cinnamic aldehyde. [Figure 9] FIG. 1 shows the results of the response-suppressing effect of the olfactory receptor OR9Q2 to p-cresol by the addition of β-caryophyllene oxide. [Figure 10] FIG. 1 shows the results of the effect of adding sclareolide on suppressing the response of olfactory receptor OR9Q2 to p-cresol. [Figure 11] This figure shows the results of the effect of adding ethyl maltol to suppress the response of the olfactory receptor OR9Q2 to p-cresol. DETAILED DESCRIPTION OF THE INVENTION

[0008] The method for searching for antagonist substances of the olfactory receptor OR9Q2 for p-cresol involves using an olfactory receptor polypeptide that is responsive to p-cresol to search for candidate substances for p-cresol odor-suppressing materials from among test substances using the following steps. (i) contacting p-cresol with an olfactory receptor polypeptide selected from the group consisting of OR9Q2 and polypeptides that contain an amino acid sequence that is 80% or more identical to the amino acid sequence of the OR9Q2 polypeptide and that are responsive to p-cresol, and measuring the response of the olfactory receptor polypeptide to p-cresol; (ii) mixing a test substance with p-cresol and measuring the response of the olfactory receptor polypeptide used in step (i); (iii) comparing the measurement results in steps (i) and (ii) and selecting the test substance that reduces the response as a candidate substance for the p-cresol odor suppressing material; Each step will be described below.

[0009] <Process (i)> The olfactory receptor polypeptide used is an olfactory receptor polypeptide selected from the group consisting of OR9Q2 and polypeptides that contain an amino acid sequence that is 80% or more identical to the amino acid sequence of any of the polypeptides and that are responsive to p-cresol. OR9Q2 is registered in GenBank as NM_001005283 and is a polypeptide consisting of the amino acid sequence (SEQ ID NO: 2) encoded by DNA of the base sequence shown in SEQ ID NO: 1. An olfactory receptor polypeptide may be used that is selected from the group consisting of polypeptides that contain an amino acid sequence that is 80% or more, preferably 85% or more, more preferably 90% or more, even more preferably 95% or more, and particularly preferably 98% or more identical to the amino acid sequence of this polypeptide (i.e., SEQ ID NO: 2) and that is responsive to p-cresol. The olfactory receptor polypeptide may be used alone or in combination of two or more. The method for measuring the response of an olfactory receptor polypeptide is not particularly limited. For example, cells isolated from an organism expressing the olfactory receptor polypeptide may be contacted with p-cresol and the response of the olfactory receptor polypeptide may be measured. Alternatively, cells in which the olfactory receptor polypeptide has been artificially expressed by genetic manipulation may be contacted with p-cresol and the response of the olfactory receptor polypeptide may be measured. The contact time between the olfactory receptor polypeptide and p-cresol is not universally specified because it depends on the concentration of p-cresol, but is typically 2 to 4 hours. The same applies when a test substance is mixed with p-cresol and then contacted with the olfactory receptor polypeptide.

[0010] The 20 N-terminal amino acid residues of bovine rhodopsin may also be incorporated together with the olfactory receptor polypeptide. By incorporating the 20 N-terminal amino acid residues of bovine rhodopsin, cell membrane expression of the olfactory receptor polypeptide can be promoted. Bovine rhodopsin is registered in GenBank as NM_001014890. Bovine rhodopsin is a polypeptide consisting of an amino acid sequence (SEQ ID NO: 4) encoded by the DNA from the 1st to 1047th positions of the nucleotide sequence shown in SEQ ID NO: 3. Alternatively, instead of bovine rhodopsin, a polypeptide may be used that contains an amino acid sequence that is 80% or more, preferably 85% or more, more preferably 90% or more, even more preferably 95% or more, and particularly preferably 98% or more identical to the amino acid sequence shown in SEQ ID NO: 3, and that can promote cell membrane expression of an olfactory receptor polypeptide. It should be noted that amino acid residues of other polypeptides, not limited to bovine rhodopsin, may be used as long as they can promote cell membrane expression of the olfactory receptor polypeptide.

[0011] The method for measuring the response of an olfactory receptor polypeptide is not particularly limited, and any method used in the art can be used. For example, it is known that when an aroma compound binds to an olfactory receptor polypeptide, it activates intracellular G protein, which then activates adenylate cyclase, converting ATP to cyclic AMP (cAMP), increasing the amount of cAMP in the cell. Therefore, the response of an olfactory receptor polypeptide can be measured by measuring the amount of cAMP. Methods for measuring the amount of cAMP include ELISA and reporter gene assays. Among these, it is preferable to measure the response of an olfactory receptor polypeptide using a reporter gene assay using a luminescent substance such as luciferase. The response of an olfactory receptor polypeptide may be evaluated using as an index the fold increase value, which is calculated by dividing the measurement result in the presence of p-cresol by the measurement result in the absence of p-cresol. For example, when measuring the response of an olfactory receptor polypeptide by a reporter gene assay using a luminescent substance such as luciferase, evaluation can be performed using p-cresol at a concentration that results in a fold increase value of preferably 2 or more, more preferably 4 or more, and even more preferably 10 or more.

[0012] <Process (ii)> The method for measuring the response of the olfactory receptor polypeptide can be the same as the method described in step (i), except that p-cresol and the test substance are mixed and contacted with the olfactory receptor polypeptide. For example, the response of the olfactory receptor polypeptide can be measured on cells isolated from an organism expressing the olfactory receptor polypeptide, or on cells in which the olfactory receptor polypeptide has been artificially expressed by genetic engineering. In order to appropriately compare the measurement results in steps (i) and (ii), it is preferable that the measurement conditions in steps (i) and (ii) are the same, except for the presence or absence of the test substance.

[0013] <Step (iii)> In step (iii), the measurement results in steps (i) and (ii) are compared, and the test substance that reduces the response is selected as a candidate substance for the p-cresol odor-suppressing material. If a comparison of the measurement results reveals a reduction in the response, the test substance used in step (ii) can be evaluated as a candidate substance for a p-cresol odor-suppressing material. Ambrettolide, isoambrettolide, pentalide, muscone, civetone, δ-2-decenolactone, cinnamic aldehyde, β-caryophyllene oxide, sclareolide, and ethyl maltol used in the present invention, which were discovered by the above-mentioned method, are all known aroma components, and commercially available products can be used.

[0014] The aroma compounds sold under the name ambrettolide are 1-oxacycloheptadecan-7-en-2-one and 1-oxacycloheptadecan-8-en-2-one, and either one can be used alone or a mixture of the two in any proportion. Ambrettolide, isoambrettolide, civetone, and cinnamic aldehyde exist as cis- and trans-isomers, and either one can be used alone, or a mixture of these in any ratio can be used. Muscone, delta-2-decenolactone, and sclareolide have optical isomers, and they may be racemic or specific optical isomers.

[0015] The deterioration odor of citral or a citral-containing product can be masked by adding one or more selected from the group consisting of ambretlide, isoambretlide, pentalide, muscone, civetone, δ-2-decenolactone, cinnamic aldehyde, β-caryophyllene oxide, sclareolide, and ethyl maltol to a citral-containing product.Furthermore, a fragrance composition containing one or more selected from the group consisting of ambretlide, isoambretlide, pentalide, muscone, civetone, δ-2-decenolactone, cinnamic aldehyde, β-caryophyllene oxide, sclareolide, and ethyl maltol can be used to mask the deterioration odor of a citral-containing product. Here, the citral-containing product is not particularly limited as long as it contains citral, and examples of the citral-containing product include citrus beverages, citrus confectioneries, citrus seasonings, ginger-containing foods, and grated ginger. The content of p-cresol in citral-containing products is preferably 100 ppt to 500 ppb, more preferably 1 ppb to 50 ppb, for citrus beverages, 1 ppb to 10 ppm, more preferably 50 ppb to 500 ppb, for citrus confectioneries and citrus seasonings, and 10 ppb to 10 ppm, more preferably 100 ppb to 1 ppm, for ginger-containing foods and grated ginger.

[0016] In the flavor composition of the present invention, the term "citrus-like flavor composition" refers to a composition used for the purpose of imparting or enhancing a flavor reminiscent of citrus fruits to foods and beverages. Examples of citrus fruits include oranges such as Valencia orange, navel orange, and blood orange; grapefruits; lemons, limes, Shikwasa (Citrus sudachi), bitter oranges, yuzu (Citrus citron), kabosu (Citrus sudachi), citron, and bush oranges; miscellaneous citrus fruits such as Natsumikan (Citrus natsudaidai), Hassaku (Citrus chinensis), Hyuganatsu (Citrus serrata), Sweetie (Citrus serrata), and Shiranuhi (Citrus shiranui); tangors such as Iyokan (Citrus iyokan) and Tankan (Citrus tankan); tangerines such as Seminole (Citrus seminole); pomegranates such as Pomegranate (Pomegranate tangerine); mandarin oranges such as Mandarin oranges, Satsuma mandarins, Ponkan (Citrus kishudaidai), and Kishu mandarins; and kumquats such as Kumquat (Kumquat), but are not limited to these citrus fruits. In the flavor composition of the present invention, the term "ginger-like flavor composition" refers to a composition used for the purpose of imparting or enhancing a flavor reminiscent of ginger to foods and beverages. Other ingredients that can be incorporated into the flavor composition of the present invention include various synthetic flavors, natural flavors, natural essential oils, plant extracts, etc., such as the natural essential oils, natural flavors, and synthetic flavors described in "Japan Patent Office Gazette, Collection of Well-Known and Commonly Used Techniques (Fragrances) Part II Food Flavors, pp. 88-131, published January 14, 2000." The fragrance composition of the present invention may contain, as necessary, commonly used additives such as solvents such as water and ethanol; and 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.

[0017] In the citral-containing product of the present invention, the term "citrus-flavored food and drink" refers to a food and drink having an aroma and taste reminiscent of citrus fruits. Citrus-flavored foods and beverages include, for example: Confectionery, snacks, sweet breads, cookies, fresh confectionery, Western-style fresh confectionery, chocolate, chocolate confectionery, foods made primarily from milk, etc., filling cream, flower paste, whipped cream, candy, gummy candy, jelly, and other foods that use citrus ingredients in part (sometimes referred to as "citrus confectionery" in this specification); Animal and vegetable fats and oils: Agricultural products and processed agricultural foods: Livestock meat and processed livestock meat foods: Fish and seafood processed foods: Dairy oil products: Ready-to-eat rice, germinated brown rice, and other cooked rice products: Instant noodles, dried noodles, chilled noodles, and other noodles: Steamed buns, prepared bread, and other bread products: Soup foods: Ready-to-eat foods, pasta sauces, canned foods, frozen and chilled foods, and other cooked and processed foods: Plant-based substitute foods; Sauces, soy sauce, dipping sauces, soup stock, mayonnaise, ketchup, dressings, tube products, dashi stock, Chinese seasonings, Western seasonings, various roux and other seasonings, spices (sometimes referred to as "citrus seasonings" in this specification); and These include beverages containing citrus juice, as well as alcoholic beverages, citrus cocktails, citrus RTDs (ready-to-drinks), and citrus RTSs (ready-to-serve drinks) (sometimes referred to herein as "citrus beverages") that use citrus ingredients in part, such as sangria. However, as long as the citrus flavor is present, it may not contain fruit juice. For example, it may be a food or beverage containing an extract containing aroma components extracted from citrus fruits, or a food or beverage containing a flavoring that artificially reproduces the characteristic aroma components of citrus fruits. Examples of beverages include citrus juice, citrus-flavored soft drinks, refreshing sweets, chewing gum, and infused alcohol obtained by infusing citrus fruits in alcohol. Beverages may or may not contain carbon dioxide. They may or may not also contain alcohol (ethanol).

[0018] In the citral-containing product of the present invention, "ginger-flavored food and drink" refers to a food having an aroma and taste reminiscent of ginger. Examples of ginger-flavored foods and drinks include: Examples of ginger-containing beverages include animal and vegetable oils and fats, agricultural products and processed agricultural foods, livestock meat and processed livestock meat products, fish and seafood processed foods, dairy oil products, cooked rice products such as retort rice and germinated brown rice, instant noodles, dried noodles, chilled noodles, and other noodles, meat buns, prepared breads, and other breads, soup foods, retort foods, pasta sauces, canned foods, frozen and chilled foods, and other cooked and processed foods, plant-based substitute foods, sauces, soy sauce, dipping sauces, tsuyu, mayonnaise, ketchup, dressings, tube products, dashi stock, Chinese seasonings, Western seasonings, and various rouxes, and other seasonings, spices, and snack foods (sometimes referred to as "ginger-containing foods" in this specification). Furthermore, as long as the ginger flavor is present, ginger-free foods are also acceptable. For example, foods and beverages containing extracts containing aroma components extracted from ginger, or foods and beverages containing flavorings that artificially reproduce the characteristic aroma components of ginger, are also acceptable.

[0019] The content of one or more selected from the group consisting of ambrettolide, isoambrettolide, pentalide, muscone, civetone, δ-2-decenolactone, cinnamic aldehyde, β-caryophyllene oxide, sclareolide, and ethyl maltol in the citrus-like fragrance composition or ginger-like fragrance composition of the present invention varies depending on the other components to be blended and cannot be generalized, but can usually be set to a concentration range of 0.01 ppm or more and 10,000 ppm or less in total, preferably 0.1 ppm or more and 1,000 ppm or less, based on the weight of the fragrance composition. If the content of one or more selected from the group consisting of ambrettolide, isoambrettolide, pentalide, muscone, civetone, δ-2-decenolactone, cinnamic aldehyde, β-caryophyllene oxide, sclareolide, and ethyl maltol is less than 0.01 ppm, the masking effect on the deterioration odor of citrus-flavored food and beverages or ginger-flavored food and beverages cannot be obtained, and if the content exceeds 10,000 ppm, the citrus flavor or ginger flavor is impaired, which is undesirable.

[0020] Furthermore, the content of one or more selected from the group consisting of ambrettolide, isoambrettolide, pentalide, muscone, civetone, δ-2-decenolactone, cinnamic aldehyde, β-caryophyllene oxide, sclareolide, and ethyl maltol contained in citral-containing products such as citrus-flavored foods and beverages or ginger-flavored foods and beverages can be set to a concentration range of 0.01 ppt or more and 10 ppm or less, preferably 1 ppt or more and 100 ppb or less, based on the weight of the citral-containing product. If the content of one or more selected from the group consisting of ambrettolide, isoambrettolide, pentalide, muscone, civetone, δ-2-decenolactone, cinnamic aldehyde, β-caryophyllene oxide, sclareolide, and ethyl maltol is less than 0.01 ppt, the masking effect on the deterioration odor of citrus-flavored food and beverages or ginger-flavored food and beverages will not be obtained, and if the content exceeds 10 ppm, the citrus flavor or ginger flavor will be impaired, which is undesirable. The present invention will be explained in more detail below with reference to examples, but the present invention is not limited to these examples. [Example]

[0021] (Measurement of olfactory receptor response to p-cresol) (1) Cloning of olfactory receptor genes The human olfactory receptor gene was obtained by PCR cloning from Human Genomic DNA: Female (Promega) based on the sequence information registered in GenBank. The N-terminal 20 amino acid residues of bovine rhodopsin were inserted into the pME18S vector, and the obtained human olfactory receptor gene was inserted downstream to obtain a human olfactory receptor gene expression vector.

[0022] (2) Expression of olfactory receptor genes in HEK293T cells A gene solution (per well) was prepared by dissolving 0.05 μg of the human olfactory receptor gene expression vector, 0.01 μg of the RTP1S vector, 0.01 μg of the firefly luciferase vector pGL4.29 (Promega) containing a cAMP response element promoter, and 0.005 μg of the Renilla luciferase vector pGL4.74 (Promega) containing a thymidine kinase promoter in 10 μL of Opti-MEMI (Gibco). HEK293T cells were seeded in 100 μL aliquots into 96-well plates (Biocoat, Corning) at a cell number that reached confluence after 24 hours. The gene solution was added to each well using the Lipofectamine 3000 lipofection method according to the manufacturer's instructions, and the cells were then cultured at 37°C in a 5% CO atmosphere for 24 hours.

[0023] (3) Luciferase reporter gene assay After removing the culture medium, 50μL of a sample of odorant prepared in CD293 (Gibco) medium (supplemented with 20μM glutamine) at the concentration required 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 strength of the olfactory receptor polypeptide was expressed as a fold increase value, calculated by dividing the luciferase activity generated by odorant stimulation by the luciferase activity generated in a test system without the odorant.

[0024] (Evaluation of the inhibitory effect of OR9Q2 response to p-cresol) 100 μM p-cresol was mixed with various concentrations of 1-oxacycloheptadecan-7-en-2-one, 1-oxacycloheptadecan-8-en-2-one, isoambrettolide, pentalide, muscone, civetone, δ-2-decenolactone, cinnamic aldehyde, β-caryophyllene oxide, sclareolide, and ethyl maltol, and the receptor response was measured in cells expressing OR9Q2. The fold-increase value in the test without each compound was set to 100, and the ratio of the fold-increase value in the test with each compound was calculated. The results are shown in Figures 1 to 11, respectively. Ambrettolide, isoambrettolide, pentalide, muscone, civetone, δ-2-decenolactone, cinnamic aldehyde, β-caryophyllene oxide, sclareolide, and ethyl maltol showed a concentration-dependent effect of reducing the response of OR9Q2 to p-cresol. Example 1 (p-cresol odor masking effect of 1-oxacycloheptadecan-7-en-2-one) Purified water was added to 2 g of lemon flavor essence (lemon oil) to bring the total volume to 1000 ml. To this citrus-flavored beverage, p-cresol adjusted to a 1% concentration by mass with 95% ethanol was added to achieve a concentration of 50 ppb. 1-oxacycloheptadecan-7-en-2-one was added to this p-cresol-containing citrus-flavored beverage at the concentrations listed in Table 1, and the intensity of the p-cresol odor (masking effect) and its effect on the citrus flavor of each sample were examined. The test was conducted by a sensory evaluation conducted by seven trained panelists. The p-cresol odor intensity of the p-cresol-containing citrus-flavored beverage without added 1-oxacycloheptadecan-7-en-2-one was rated as "Rating: 4," and the p-cresol odor intensity of the citrus-flavored beverage without added p-cresol was rated as "Rating: 0." The p-cresol odor intensity (masking effect) of each sample was then relatively rated according to the following evaluation criteria.

[0025] (Evaluation criteria) Strong p-cresol odor: 4 points p-Cresol odor: 3 points Slight p-cresol odor: 2 points Almost no p-cresol odor: 1 point No p-cresol odor detected: 0 points In addition, the influence on the citrus flavor of the citrus flavored beverage was evaluated in absolute terms in terms of the presence or absence of p-cresol odor and off-flavors other than the citrus flavor, according to the following evaluation criteria.

[0026] (Evaluation criteria) Strong off-flavor: 4 points Unusual flavor: 3 points Slightly strange flavor: 2 points Almost no off-flavor: 1 point No off-flavors detected: 0 points The results are shown in Table 1, which shows the average scores of the evaluation results of each panel.

[0027] [Table 1] The results in Table 1 clearly show that 1-oxacycloheptadecan-7-en-2-one masks the p-cresol odor at concentrations of 0.1 ppt or more and 1 ppb or less, without affecting the citrus flavor. Example 2 (p-cresol odor masking effect of 1-oxacycloheptadecan-8-en-2-one) Using samples prepared in the same manner as in Example 1, the intensity of the p-cresol odor (masking effect) of 1-oxacycloheptadecan-8-en-2-one and its effect on the citrus flavor were confirmed. The evaluation method was the same as in Example 1. The results are shown in Table 2, which shows the average scores of each panelist.

[0028] [Table 2] The results in Table 2 clearly show that 1-oxacycloheptadecan-8-en-2-one masks the p-cresol odor at concentrations of 0.1 ppt or more and 1 ppb or less, without affecting the citrus flavor. Example 3 (p-cresol odor masking effect of isoambrettolide) Using samples prepared in the same manner as in Example 1, the intensity of the p-cresol odor (masking effect) of isoambrettolide and its effect on the citrus flavor were confirmed. The evaluation method was the same as in Example 1. The results are shown in Table 3, which shows the average scores of each panelist.

[0029] [Table 3] The results in Table 3 clearly show that isoambrettolide masks the p-cresol odor at concentrations of 0.1 ppt or more and 1 ppb or less, without affecting the citrus flavor. Example 4 (p-cresol odor masking effect of pentalide) Using samples prepared in the same manner as in Example 1, the intensity of the p-cresol odor (masking effect) of pentalide and its effect on the citrus flavor were confirmed. The evaluation method was the same as in Example 1. The results are shown in Table 4, which shows the average scores of each panelist.

[0030] [Table 4] The results in Table 4 clearly show that pentalide masks the p-cresol odor at concentrations of 0.1 ppt or more and 1 ppb or less, without affecting the citrus flavor. Example 5 (p-cresol odor masking effect of muscone) Using samples prepared in the same manner as in Example 1, the intensity of the p-cresol odor of muscone (masking effect) and its effect on the citrus flavor were confirmed. The evaluation method was the same as in Example 1. The results are shown in Table 5, which shows the average scores of each panelist.

[0031] [Table 5] The results in Table 5 clearly show that muscone masks the p-cresol odor at concentrations above 0.01 ppt and below 1 ppb without affecting the citrus flavor. Example 6 (p-cresol odor masking effect of civetone) Using samples prepared in the same manner as in Example 1, the intensity of the p-cresol odor (masking effect) of civetone and its effect on the citrus flavor were confirmed. The evaluation method was the same as in Example 1. The results are shown in Table 6, which shows the average scores of each panelist.

[0032] [Table 6] The results in Table 6 clearly show that civetone masks the p-cresol odor at concentrations of 0.01 ppt or more and 1 ppb or less, without affecting the citrus flavor. Example 7 (p-cresol odor masking effect of δ-2-decenolactone) Using samples prepared in the same manner as in Example 1, the effect of δ-2-decenolactone on the strength of the p-cresol odor (masking effect) and the citrus flavor was confirmed. The evaluation method was the same as in Example 1. The results are shown in Table 7, which shows the average scores of each panel.

[0033] [Table 7] The results in Table 7 clearly show that δ-2-decenolactone masks the p-cresol odor at concentrations of 10 ppt or more and 100 ppb or less, without affecting the citrus flavor. Example 8 (p-cresol odor masking effect of cinnamic aldehyde) Using samples prepared in the same manner as in Example 1, the effect of cinnamic aldehyde on the intensity of the p-cresol odor (masking effect) and the citrus flavor was confirmed. The evaluation method was the same as in Example 1. The results are shown in Table 8, which shows the average scores of each panelist.

[0034] [Table 8] The results in Table 8 clearly show that synamic aldehyde masks the p-cresol odor at concentrations of 100 ppt or more and 10 ppm or less, without affecting the citrus flavor. Example 9 (p-cresol odor masking effect of β-caryophyllene oxide) Using samples prepared in the same manner as in Example 1, the intensity of the p-cresol odor (masking effect) of β-caryophyllene oxide and its effect on the citrus flavor were confirmed. The evaluation method was the same as in Example 1. The results are shown in Table 9, which shows the average scores of each panelist.

[0035] [Table 9] The results in Table 9 clearly show that β-caryophyllene oxide masks the p-cresol odor at concentrations of 100 ppt or more and 1 ppm or less, without affecting the citrus flavor. Example 10 (p-cresol odor masking effect of sclareolide) Using samples prepared in the same manner as in Example 1, the effect of sclareolide on the intensity of the p-cresol odor (masking effect) and the citrus flavor was confirmed. The evaluation method was the same as in Example 1. The results are shown in Table 10, which shows the average scores of each panelist.

[0036] [Table 10] The results in Table 10 clearly show that sclareolide masks the p-cresol odor at concentrations of 100 ppt or more and 1 ppm or less, without affecting the citrus flavor. Example 11 (Effect of Ethyl Maltol on Masking p-Cresol Odor) Using samples prepared in the same manner as in Example 1, the intensity of the p-cresol odor (masking effect) of ethyl maltol and its effect on the citrus flavor were confirmed. The evaluation method was the same as in Example 1. The results are shown in Table 11, which shows the average scores of each panelist.

[0037] [Table 11] The results in Table 11 clearly show that ethyl maltol masks the p-cresol odor at concentrations of 100 ppt or more and 10 ppm or less, without affecting the citrus flavor. Example 12 (p-cresol odor masking effect of 1-oxacycloheptadecan-7-en-2-one) Lemon cold-pressed oil was added to a tablet dough of the composition shown in Table A at a concentration of 1% by mass, and p-cresol adjusted to a concentration of 0.1% with medium-chain triglyceride (MCT) was further added so that the concentration in the citrus-flavored confectionery was 200 ppb. 1-oxacycloheptadecan-7-en-2-one was added to this p-cresol-containing citrus-flavored confectionery at the concentration shown in Table 12, and then the confectionery was tableted. The intensity of the p-cresol odor (masking effect) and its effect on the citrus flavor of each sample were confirmed.

[0038] (Ingredients for tablet candy) TIFF0007770312000012.tif36137 Mortar and pestle diameter: 7mm Six skilled panelists were selected and subjected to the same sensory evaluation as in Example 1. The results are shown in Table 12, which shows the average scores of the evaluation results of each panelist.

[0039] [Table 12] The results in Table 12 clearly show that 1-oxacycloheptadecan-7-en-2-one masks the p-cresol odor at concentrations of 400 ppt or more and 400 ppb or less, without affecting the citrus flavor. Example 13 (p-cresol odor masking effect of 1-oxacycloheptadecan-8-en-2-one) The masking effect of 1-oxacycloheptadecan-8-en-2-one was evaluated in the same manner as in Example 12, and the results are shown in Table 13.

[0040] [Table 13] The results in Table 13 clearly show that 1-oxacycloheptadecan-8-en-2-one masks the p-cresol odor at concentrations of 4 ppb or more and 400 ppb or less, without affecting the citrus flavor. Example 14 (p-cresol odor masking effect of isoambrettolide) The masking effect of isoambrettolide was evaluated in the same manner as in Example 12, and the results are shown in Table 14.

[0041] [Table 14] The results in Table 14 clearly show that isoambrettolide masks the p-cresol odor at concentrations of 400 ppt or more and 400 ppb or less, without affecting the citrus flavor. Example 15 (p-cresol odor masking effect of pentalide) The masking effect of pentalide was evaluated in the same manner as in Example 12, and the results are shown in Table 15.

[0042] [Table 15] The results in Table 15 clearly show that pentalide masks the p-cresol odor at concentrations of 400 ppt or more and 400 ppb or less, without affecting the citrus flavor. Example 16 (p-cresol odor masking effect of 1-oxacycloheptadecan-8-en-2-one) Commercially available grated fresh ginger was treated with 0.1% p-cresol in 95% ethanol to achieve a concentration of 600 ppb. 1-Oxacycloheptadecan-8-en-2-one was added to the p-cresol-containing ginger at the concentrations listed in Table 16, and the intensity of the p-cresol odor (masking effect) and its effect on the ginger flavor were examined. Nine skilled panelists were selected and subjected to the same sensory evaluation as in Example 1. The results are shown in Table 16, which shows the average scores of the evaluation results of each panelist.

[0043] [Table 16] The results in Table 16 clearly show that 1-oxacycloheptadecan-8-en-2-one masks the p-cresol odor at concentrations of 10 ppt or more and 1 ppb or less, without affecting the ginger flavor. Example 17 (p-cresol odor masking effect of pentalide) The masking effect of pentalide was evaluated in the same manner as in Example 16, and the results are shown in Table 17.

[0044] [Table 17] The results in Table 17 clearly show that pentalide masks the p-cresol odor at concentrations of 10 ppt or more and 1 ppb or less, without affecting the ginger flavor. Example 18 (p-cresol odor masking effect of 1-oxacycloheptadecan-8-en-2-one) Commercially available lemon dressing was supplemented with 0.1% p-cresol in 95% ethanol to achieve a concentration of 500 ppb. 1-Oxacycloheptadecan-8-en-2-one was added to the p-cresol-containing lemon dressing at the concentrations listed in Table 18. The intensity of the p-cresol odor (masking effect) and its effect on the citrus flavor of each sample were then examined.

[0045] Nine skilled panelists were selected and subjected to the same sensory evaluation as in Example 1. The results are shown in Table 18, which shows the average scores of the evaluation results of each panelist.

[0046] [Table 18] The results in Table 18 clearly show that 1-oxacycloheptadecan-8-en-2-one masks the p-cresol odor at concentrations of 1 ppt or more and 10 ppb or less, without affecting the citrus flavor. Example 19 (p-cresol odor masking effect of pentalide) The masking effect of pentalide was investigated in the same manner as in Example 18, and the results are shown in Table 19.

[0047] [Table 19] The results in Table 19 clearly show that pentalide masks the p-cresol odor at concentrations of 10 ppt or more and 10 ppb or less, without affecting the citrus flavor.

Claims

1. A method for masking the deterioration odor of citral or a citral-containing product, comprising adding one or more compounds selected from the group consisting of ambrettolide, isoambrettolide, pentalide, muscone, civetone, δ-2-decenolactone, cinnamic aldehyde, β-caryophyllene oxide, and sclareolide to a citral-containing product, The citral-containing product is a citrus-flavored food or drink or a ginger-flavored food or drink, When the adding step includes adding ambrettolide, the adding step includes adding ambrettolide so that the concentration of ambrettolide in the citrus-flavored food or drink or the ginger-flavored food or drink is 0.1 ppt to 1 ppb; When the adding step includes adding isoambrettolide, the adding step includes adding isoambrettolide so that the concentration of isoambrettolide in the citrus-flavored food or drink or the ginger-flavored food or drink is 0.1 ppt to 1 ppb; When the adding step includes adding a pentalide, the adding step includes adding the pentalide so that the concentration of the pentalide in the citrus-flavored food or drink or the ginger-flavored food or drink is 0.1 ppt to 1 ppb; When the adding step includes adding muscone, the adding step includes adding muscone so that the concentration of the muscone in the citrus-flavored food or drink or the ginger-flavored food or drink is 0.01 ppt to 1 ppb; When the adding step includes adding civetone, the adding step includes adding civetone so that the concentration of civetone in the citrus-flavored food or drink or the ginger-flavored food or drink is 0.01 ppt to 1 ppb; When the adding step includes adding δ-2-decenolactone, the adding step includes adding the δ-2-decenolactone so that the concentration of the δ-2-decenolactone in the citrus-flavored food or drink or the ginger-flavored food or drink is 10 ppt to 100 ppb; When the adding step includes adding cinnamic aldehyde, the adding step includes adding the cinnamic aldehyde so that the concentration of the cinnamic aldehyde in the citrus-flavored food or drink or the ginger-flavored food or drink is 100 ppt to 10 ppm; When the adding step includes adding β-caryophyllene oxide, the adding step includes adding β-caryophyllene oxide so that the concentration of the β-caryophyllene oxide in the citrus-flavored food or drink or the ginger-flavored food or drink is 100 ppt to 1 ppm; When the adding step includes adding sclareolide, the adding step includes adding the sclareolide so that the concentration of the sclareolide in the citrus-flavored food or drink or the ginger-flavored food or drink is 100 ppt to 1 ppm.

2. 2. The masking method according to claim 1, wherein the deterioration odor is p-cresol.

3. A fragrance composition for masking the deterioration odor of citral-containing products, comprising one or more compounds selected from the group consisting of ambrettolide, isoambrettolide, pentalide, muscone, civetone, δ-2-decenolactone, cinnamic aldehyde, β-caryophyllene oxide, and sclareolide, The citral-containing product is a citrus-flavored food or drink or a ginger-flavored food or drink, When the fragrance composition contains ambrettolide, the concentration of ambrettolide in the fragrance composition is 50 ppt to 500 ppb; When the fragrance composition contains isoambrettolide, the concentration of isoambrettolide in the fragrance composition is 50 ppt to 500 ppb, When the fragrance composition contains a pentalide, the concentration of the pentalide in the fragrance composition is 50 ppt to 500 ppb; When the fragrance composition contains muscone, the concentration of muscone in the fragrance composition is 5 ppt to 500 ppb; When the fragrance composition contains civetone, the concentration of civetone in the fragrance composition is 5 ppt to 500 ppb; When the fragrance composition contains δ-2-decenolactone, the concentration of δ-2-decenolactone in the fragrance composition is 500 ppt to 50 ppb; When the fragrance composition contains cinnamic aldehyde, the concentration of cinnamic aldehyde in the fragrance composition is 5 ppb to 5000 ppm; when the fragrance composition contains β-caryophyllene oxide, the concentration of β-caryophyllene oxide in the fragrance composition is 5 ppb to 500 ppm; When the fragrance composition contains sclareolide, the concentration of sclareolide in the fragrance composition is 5 ppb to 500 ppm.

4. The fragrance composition according to claim 3, which has a citrus or ginger flavor.

5. 5. The fragrance composition according to claim 3, wherein the deterioration odor is p-cresol.

6. A citral-containing product containing 0.01 ppt to 10 ppm of one or more selected from the group consisting of ambrettolide, isoambrettolide, pentalide, muscone, civetone, and sclareolide, The citral-containing product is a citrus-flavored food or drink or a ginger-flavored food or drink, When the citrus-flavored food or drink or the ginger-flavored food or drink contains ambrettolide, the concentration of ambrettolide in the citrus-flavored food or drink or the ginger-flavored food or drink is 0.1 ppt to 1 ppb, When the citrus-flavored food or drink or the ginger-flavored food or drink contains isoambrettolide, the concentration of isoambrettolide in the citrus-flavored food or drink or the ginger-flavored food or drink is 0.1 ppt to 1 ppb, When the citrus-flavored food or drink or the ginger-flavored food or drink contains pentalide, the concentration of pentalide in the citrus-flavored food or drink or the ginger-flavored food or drink is 0.1 ppt to 1 ppb, When the citrus-flavored food or drink or the ginger-flavored food or drink contains muscone, the concentration of muscone in the citrus-flavored food or drink or the ginger-flavored food or drink is 0.01 ppt to 1 ppb, When the citrus-flavored food or drink or the ginger-flavored food or drink contains civetone, the concentration of civetone in the citrus-flavored food or drink or the ginger-flavored food or drink is 0.01 ppt to 1 ppb; When the citrus-flavored food or drink or the ginger-flavored food or drink contains sclareolide, the concentration of sclareolide in the citrus-flavored food or drink or the ginger-flavored food or drink is 100 ppt to 1 ppm; A citrus-flavored food or drink or a ginger-flavored food or drink containing 10 ppb to 1 ppm of p-cresol.

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