Unpleasant aroma improving composition

Abstract

To provide a composition effective in improving unpleasant flavor.SOLUTION: An unpleasant flavor improving composition containing a specific cyclic ketone compound, or a cyclic ketone compound having a specific furanone skeleton as an active ingredient, wherein the unpleasant flavor is derived from a milk component and / or an unpleasant flavor derived from a fruit juice component; a manufacturing method of the unpleasant flavor improving composition comprising adding the specific cyclic ketone compound, or the cyclic ketone compound having the specific furanone skeleton in a composition that can be added to consumer goods; and an unpleasant flavor improving method of the consumer goods comprising blending the unpleasant flavor improving composition to the consumer goods are provided.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a composition for improving an unpleasant flavor, and more particularly to a composition for improving an unpleasant flavor that contains a specific cyclic ketone compound. [Background technology]

[0002] Consumer demands for the scent and taste (sometimes collectively referred to as flavor in this specification) of various consumer goods such as foods, beverages, and cosmetics are becoming more sophisticated, and several technologies have been proposed to improve unpleasant flavors.

[0003] For example, Patent Document 1 proposes that adding 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid or 10-dodecenoic acid to food or drink reduces unpleasant tastes in the food or drink, particularly unpleasant tastes derived from sourness, bitterness and astringency, without imparting unnecessary aroma or flavor to the food or drink, and improves the flavor of the food or drink. Patent Document 2 describes an odor suppressant for the casein odor or collagen odor of casein or collagen, which is characterized by containing chlorogenic acid as an active ingredient. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] JP 2020-188705 A [Patent Document 2] JP 2003-210119 A Summary of the Invention [Problem to be solved by the invention]

[0005] However, conventionally used materials for improving unpleasant flavors have not been sufficient to improve various unpleasant flavors, and it has been an issue to discover a useful material capable of improving unpleasant flavors. Therefore, an issue of the present invention is to provide an unpleasant flavor improving composition containing a compound useful for improving unpleasant flavors. [Means for solving the problem]

[0006] Means for Solving the Problems The present inventors have conducted intensive research in view of the above problems and have found that a group of cyclic ketone compounds having a specific structure is useful for improving unpleasant flavors, thereby completing the present invention.

[0007] Thus, a brief outline of representative inventions among those disclosed in this application is as follows. [1] A composition for improving an unpleasant flavor, comprising as an active ingredient at least one cyclic ketone compound selected from the compounds described in the following groups A and B: (Group A) Cyclic ketone compounds represented by the following formula A

[0008] [ka]

[0009] [In the formula, n represents 0 or 1, the dashed line represents a single bond or a double bond, and when the dashed line on the ring represents a double bond, R 1 and R 2 is a hydroxy group and the other is a hydrogen, methyl or ethyl group, and the dashed line on the ring is a single bond, R 1 and R 2 is an oxygen atom double-bonded to a carbon atom on the ring, and a hydrogen atom, a methyl group, or an ethyl group on the other side, and R 3 and R 4 are each independently a hydrogen atom, a methyl group, or an ethyl group. (Group B) Cyclic ketone compounds having a furanone skeleton represented by the following formula B

[0010] [ka]

[0011] [In the formula, R 1 represents a methyl group or an ethyl group, and R 2 represents hydrogen or an acyl group having 2 to 4 carbon atoms, and R 3represents hydrogen, a methyl group, or an ethyl group. (However, R 1 is a methyl group, R 2 is hydrogen, R 3 is a methyl group.)] [2] The flavor improving composition according to [1], wherein the group A is a group consisting of a compound represented by the following formula Aa and a compound represented by the following formula Ab:

[0012] [ka]

[0013] [In the formula, the dashed line represents a single bond or a double bond, and when the dashed line on the ring represents a double bond, Ra 1 is a hydroxy group, Ra 2 is hydrogen, a methyl group, or an ethyl group, and when the dashed line on the ring is a single bond, Ra 1 is an oxygen atom double-bonded to a carbon atom on the ring, Ra 2 is hydrogen, a methyl group, or an ethyl group, and Ra 3 and Ra 4 are each independently a hydrogen atom, a methyl group, or an ethyl group.

[0014] [ka]

[0015] [In the formula, the dashed line represents a single bond or a double bond, and when the dashed line on the ring represents a double bond, Rb 1 is a hydroxy group, Rb 2 is hydrogen, a methyl group, or an ethyl group, and when the dashed line on the ring is a single bond, Rb 1 is an oxygen atom double-bonded to a carbon atom on the ring, Rb 2 is hydrogen, a methyl group, or an ethyl group, and Ra 3 and Ra 4 are each independently a hydrogen atom, a methyl group, or an ethyl group; Rb 5 is hydrogen.] [3] The unpleasant flavor improving composition according to [1] or [2], wherein the compound belonging to Group A is a compound selected from the following formulae A-1 to A-10:

[0016] [ka]

[0017] [4] The unpleasant flavor improving composition according to any one of [1] to [3], wherein the compound belonging to group B is a compound selected from the following formulae B-1 to B-4:

[0018] [ka]

[0019] [5] The unpleasant flavor improving composition according to any one of [1] to [4], wherein the unpleasant flavor is an unpleasant flavor derived from a milk component and / or an unpleasant flavor derived from a fruit juice component. [6] The unpleasant flavor improving composition according to any one of [1] to [5], wherein the unpleasant flavor is a light-deterioration odor of milk or a light-deterioration odor of fruit juice. [7] The unpleasant flavor improving composition according to any one of [1] to [6], which further has an effect of imparting a sweet flavor. [8] The unpleasant flavor improving composition according to any one of [1] to [7], further comprising a keto-enol tautomer corresponding to each of the compounds in Group A and Group B contained in the unpleasant flavor improving composition. [9] The unpleasant flavor improving composition according to [4], wherein when the unpleasant flavor improving composition contains a compound of formula B-4, it further contains a 5-ethyl form.

[10] A method for producing a composition for improving an unpleasant flavor, comprising adding at least one compound selected from the compounds described in the following groups A and B to a composition that can be added to consumer goods. (Group A) Cyclic ketone compounds represented by the following formula A

[0020] [ka]

[0021] [In the formula, n represents 0 or 1, the dashed line represents a single bond or a double bond, and when the dashed line on the ring represents a double bond, R 1 and R 2 is a hydroxy group and the other is a hydrogen, methyl or ethyl group, and the dashed line on the ring is a single bond, R 1 and R 2 is an oxygen atom double-bonded to a carbon atom on the ring, and a hydrogen atom, a methyl group, or an ethyl group on the other side, and R 3 and R 4 are each independently a hydrogen atom, a methyl group, or an ethyl group. (Group B) Cyclic ketone compounds having a furanone skeleton represented by the following formula B

[0022] [ka]

[0023] [In the formula, R 1 represents a methyl group or an ethyl group, and R 2 represents hydrogen or an acyl group having 2 to 4 carbon atoms, and R 3 represents hydrogen, a methyl group, or an ethyl group. (However, R 1 is a methyl group, R 2 is hydrogen, R 3 is a methyl group.)]

[11] A method for improving an unpleasant flavor in a consumer good, comprising blending the unpleasant flavor improving composition according to any one of [1] to [9] into the consumer good.

[12] A method for improving an unpleasant flavor in a consumer good according to

[11] , comprising blending the unpleasant flavor improving composition according to any one of [1] to [9] into a consumer good at a final concentration such that the concentration of the cyclic ketone compound selected from group A and group B is in the range of 10 ppb to 1%, wherein the consumer good is a food or beverage.

[13] The method for improving an unpleasant flavor of a consumer product according to

[11] , wherein the concentration range is 10 ppb to 10 ppm.

[14] The method for improving an unpleasant flavor of a consumer product described in

[12] or

[13] , wherein the food or beverage contains milk and / or fruit juice.

[15] A consumer product comprising the unpleasant flavor improving composition according to any one of [1] to [9]. Effect of the Invention

[0024] INDUSTRIAL APPLICABILITY The present invention makes it possible to provide an unpleasant flavor improving composition which is effective in improving unpleasant flavors. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0025] The present invention will be described in more detail below with reference to specific examples. In this specification, the symbol "to" means a range including a lower limit and an upper limit, and concentrations (ppt, ppb, ppm, etc.) and % mean mass concentrations and mass %, respectively, unless otherwise specified, and concentrations refer to final concentrations unless otherwise specified.

[0026] [Unpleasant flavor improving composition] The unpleasant flavor improving composition according to one embodiment of the present invention (sometimes simply referred to as the unpleasant flavor improving composition of the present invention in this specification) contains a predetermined amount of a group of compounds represented by formulas A to B shown in the following A to B groups (sometimes simply referred to as "the present compound" in this specification for one type of these compounds or for two or more types of these compounds collectively), and can be added to various consumer goods to improve the unpleasant flavor of the consumer goods. There are no particular limitations on the means for obtaining the present compound, and a commercially available compound can be used. In this specification, "adding" includes at least one of simply adding the compound to a certain object by spraying, dropping, etc., and mixing the compound with a certain object.

[0027] Group A refers to cyclic ketone compounds represented by the following formula A.

[0028] [ka]

[0029] [In the formula, n represents 0 or 1, the dashed line represents a single bond or a double bond, and when the dashed line on the ring represents a double bond, R 1 and R 2 is a hydroxy group and the other is a hydrogen, methyl or ethyl group, and the dashed line on the ring is a single bond, R 1 and R 2 is an oxygen atom double-bonded to a carbon atom on the ring, and a hydrogen atom, a methyl group, or an ethyl group on the other side, and R 3 and R 4 are each independently a hydrogen atom, a methyl group, or an ethyl group.

[0030] More preferably, it is a compound of the following formula Aa or a compound of the following formula Ab:

[0031] [ka]

[0032] [In the formula, the dashed line represents a single bond or a double bond, and when the dashed line on the ring represents a double bond, Ra 1 is a hydroxy group, Ra 2 is hydrogen, a methyl group, or an ethyl group, and when the dashed line on the ring is a single bond, Ra 1 is an oxygen atom double-bonded to a carbon atom on the ring, Ra 2 is hydrogen, a methyl group, or an ethyl group, and Ra 3 and Ra 4 are each independently a hydrogen atom, a methyl group, or an ethyl group.

[0033] In the formula Aa, preferably, Ra 2 ~Ra 4 At least one of Ra is a methyl group or an ethyl group and the others are hydrogen. More preferably, Ra 2 is a methyl group or an ethyl group, and Ra 3 and Ra 4 is hydrogen or Ra 2 ~Ra 4 Two of the positions are methyl groups and the other one is hydrogen.

[0034] [ka]

[0035] [In the formula, the dashed line represents a single bond or a double bond, and when the dashed line on the ring represents a double bond, Rb 1 is a hydroxy group, Rb 2 is hydrogen, a methyl group, or an ethyl group, and when the dashed line on the ring is a single bond, Rb 1 is an oxygen atom double-bonded to a carbon atom on the ring, Rb 2 is hydrogen, a methyl group, or an ethyl group, and Ra 3 and Ra 4 are each independently a hydrogen atom, a methyl group, or an ethyl group; Rb 5 is hydrogen.]

[0036] In the formula Ab, preferably, Rb 2 ~Rb 4 At least one of Rb is a methyl group or an ethyl group, and more preferably, the dashed line on the ring is a single bond and Rb 1 is oxygen, Rb 2 ~Rb 4 is a methyl group or an ethyl group and the others are hydrogen; more preferably, the dashed line on the ring is a single bond and Rb 1 is oxygen, and Rb 2 ~Rb 4 One of the groups is a methyl group and the others are hydrogen.

[0037] Group B is a cyclic ketone compound having a furanone skeleton represented by the following formula B.

[0038] [ka]

[0039] [In the formula, R 1 represents a methyl group or an ethyl group, and R 2 represents hydrogen or an acyl group having 2 to 4 carbon atoms, and R 3 represents hydrogen, a methyl group, or an ethyl group. (However, R 1 is a methyl group, R2 is hydrogen, R 3 is a methyl group.)]

[0040] In formula B, preferably, R 1 is a methyl group.

[0041] The compounds represented by formula A and the compounds represented by formula B include all stereoisomers. In this specification, the compounds represented by formula A may be simply referred to as compounds of formula A as a collective term for one kind or two or more kinds. The same applies to the compounds represented by formula B.

[0042] Of the compounds of formula A and formula B, preferred specific examples include the compounds of the following formulae A-1 to A-10 and B-1 to B-4. The formula Aa includes the compounds of A-1 to A-5, and the formula Ab includes the compounds of formulae A-8 and A-9. The compound A-1 is cyclotene (in formula A, n is 0, the dashed line on the ring is a double bond, R 1 is a hydroxy group, R 2 is a methyl group, R 3 and R 4 is hydrogen; in formula Aa, the dashed line on the ring is a double bond, Ra 1 is a hydroxy group, Ra 2 is a methyl group, Ra 3 and Ra 4 is hydrogen), and the compound A-2 is ethyl cyclopentenolone (where n is 0, the dashed line on the ring is a double bond, and R 1 is a hydroxy group, R 2 is an ethyl group, R 3 and R 4 is hydrogen; in formula Aa, the dashed line on the ring is a double bond, Ra 1 is a hydroxy group, Ra 2 is an ethyl group, Ra 3 and Ra 4 is hydrogen), the compound A-3 is methyl corylone (in formula A, n is 0, the dashed line on the ring is a single bond, R 1 is oxygen, R2 and R 3 is a methyl group, R 4 is hydrogen; in formula Aa, the dashed line on the ring is a single bond, Ra 1 is oxygen, Ra 2 and Ra 3 is a methyl group, Ra 4 is hydrogen), and the compound A-4 is 3,5-dimethyl-1,2-cyclopentanedione (where n is 0, the dashed line on the ring is a single bond, and R 1 is oxygen, R 2 and R 4 is a methyl group, R 3 is hydrogen; in formula Aa, the dashed line on the ring is a single bond, Ra 1 is oxygen, Ra 2 and Ra 4 is a methyl group, Ra 3 is hydrogen), and the compound A-5 is 1,2-cyclopentanedione (where n is 0, the dashed line on the ring is a single bond, and R 1 is oxygen, R 2 , R 3 and R 4 is hydrogen; in formula Aa, the dashed line on the ring is a single bond, Ra 1 is oxygen, Ra 2 , Ra 3 and Ra 4 is hydrogen), and the compound A-6 is 1,3-cyclopentanedione (where n is 0, the dashed line on the ring is a single bond, and R 1 is hydrogen, R 2 is oxygen, R 3 and R 4 is hydrogen), and the compound A-7 is 2-methyl-1,3-cyclopentanedione (where n is 0, the dashed line on the ring is a single bond, and R 1 is a methyl group, R 2 is oxygen, R 3 and R 4is hydrogen), and the compound in A-8 is 3-methyl-1,2-cyclohexanedione (in formula A, n is 1, the dashed line on the ring is a single bond, R 1 is oxygen, R 2 is a methyl group, R 3 and R 4 is hydrogen; in formula Ab, the dashed line on the ring is a single bond, Rb 1 is oxygen, Rb 2 is a methyl group, Rb 3 and Rb 4 is hydrogen), and the compound of A-9 is 1,2-cyclohexanedione (in formula A, n is 1, the dashed line on the ring is a single bond, R 1 is oxygen, R 2 , R 3 and R 4 is hydrogen; in formula Ab, the dashed line on the ring is a single bond, Rb 1 is oxygen, Rb 2 , Rb 3 and Rb 4 is hydrogen), and the compound of A-10 is 1,3-cyclohexanedione (in formula A, n is 1, the dashed line on the ring is a single bond, R 1 is hydrogen, R 2 is oxygen, R 3 and R 4 is hydrogen), and the compound B-1 is furaneol acetate (in formula B, R 1 is a methyl group, R 2 is an acyl group having 2 carbon atoms, R 3 is a methyl group), and the compound B-2 is furaneol butyrate (where R 1 is a methyl group, R 2 is an acyl group having 4 carbon atoms, R 3 is a methyl group), and the compound B-3 is 4-hydroxy-5-methyl-2(H)-furan-3-one (R 1 is a methyl group, R 2 is hydrogen, R3 is hydrogen), and the compound B-4 is 2-ethyl-4-hydroxy-5-methyl-2(H)-furan-3-one (R 1 is a methyl group, R 2 is hydrogen, R 3 is an ethyl group).

[0043] [ka]

[0044] [ka]

[0045] Among the compounds of formulae A-1 to A-10 and B-1 to B4, particularly preferred examples include the compounds of formulae A-1, A-2, A-3, A-4, A-8, A-9, B-1, B-2, B-3 and B-4.

[0046] In addition, keto-enol tautomers naturally exist in the compounds of formula A and formula B, and it is believed that the unpleasant flavor improving composition containing the compound of formula A or the compound of formula B contains the tautomers, and a mixture of the compound of formula A and its keto-enol tautomer, and a mixture of the compound of formula B and its keto-enol tautomer also have an unpleasant flavor improving effect. The keto-enol tautomers may also be used to improve unpleasant flavors.For example, naturally occurring keto-enol tautomers of the compounds of formula A-1, A-2, A-3, A-4, A-5, A-8, A-9, B-3, and B-4 include 3-methyl-1,2-cyclopentanedione as the keto-enol tautomer of the compound of formula A-1, 3-ethyl-1,2-cyclopentanedione as the keto-enol tautomer of the compound of formula A-2, and 3-ethyl-1,2-cyclopentanedione as the keto-enol tautomer of the compound of formula A-3. l-1,2-cyclopentanedione), 2-hydroxy-3,4-dimethyl-2-cyclopentenone as the keto-enol tautomer of the compound of formula A-3, 2-hydroxy-3,5-dimethyl-2-cyclopentenone as the keto-enol tautomer of the compound of formula A-4, 2-hydroxy-2-cyclopentenone as the keto-enol tautomer of the compound of formula A-5, 2-hydroxy-3-methyl-2-cyclohexenone as the keto-enol tautomer of the compound of formula A-8, 2-hydroxy-2-cyclohexenone as the keto-enol tautomer of the compound of formula A-9, The keto-enol tautomer of the compound of formula B-3 is 2-methyl-3,4(2H,5H)-furandione, and the keto-enol tautomer of the compound of formula B-4 is 2-ethyl-5-methyl-3,4(2H,5H)-furandione.

[0047] As for the formula B-4, the commercially available product of the compound B-4, 2-ethyl-4-hydroxy-5-methyl-2(H)-furan-3-one, may contain 5-ethyl-4-hydroxy-2-methyl-2(H)-furan-3-one (hereinafter, sometimes referred to as the 5-ethyl form), and a mixture of the compound B-4 and the 5-ethyl form also has an effect of improving unpleasant flavors. The 5-ethyl form may also be used to improve unpleasant flavors.

[0048] In the present specification, the term "unpleasant flavor" refers to an unpleasant flavor that animals with a sense of smell, typically humans, can sense, and typically includes sulfur-like flavor and fried oil-like flavor. The sulfur-like flavor may include one or more of unpleasant cabbage-like, onion-like, garlic-like, pickled radish-like, meat-like (which may include a rotten or cooked feeling), egg-like (egg yolk odor, rotten egg odor and / or egg white odor), cheese-like, potato-like, and burnt odors, which may also include a stimulating sensation. The fried oil-like flavor refers to a scent like oil after being used for fried foods, and a sensation including the unique oily odor of oxidized oil. Examples of the sulfur-like flavor and / or fried oil-like flavor that may become an unpleasant flavor include unpleasant flavors, bad breath, body odor, and feces-like odors caused by component deterioration over time due to component interactions in various consumer goods or component deterioration due to light or heat, and the unpleasant flavor improving composition of the present invention has a particularly remarkable improving effect on unpleasant flavors including sulfur-like flavor and / or fried oil-like flavor. In particular, the unpleasant flavor improving composition of the present invention can be suitably used for improving the light deterioration odor of milk or fruit juice, which is believed to be caused by methionine, a sulfur-like unpleasant flavor.

[0049] In addition, "flavor" refers to one or more senses that can be changed by a scent, typically including the senses of smell and taste.

[0050] "Improvement" includes making the unpleasant flavor detected from a consumer good weaker or substantially undetectable compared to when the unpleasant flavor improving composition of the present invention is not added, and preferably also includes imparting a flavor to the consumer good compared to when the unpleasant flavor improving composition of the present invention is not added, thereby improving the flavor of the consumer good.

[0051] Representative compounds known to be the source of unpleasant flavors include, but are not limited to, methional, methanethiol, dimethyl disulfide, and dimethyl trisulfide. In particular, for the unpleasant odors derived from milk and fruit juice, which are known to be a problem to improve, methional, which is considered to be a causative substance of the unpleasant odor caused by stimuli such as light and heat (various compounds that may be generated when components in milk or fruit juice change or interact with each other due to the above stimuli or changes over time), may be a representative substance that is the source of unpleasant flavors. In this specification, the term "compounds that are the source of unpleasant flavors" includes the compound itself or compounds that can be generated from the compound by decomposition, binding, etc.

[0052] The unpleasant flavor of consumer goods may be due to compounds originally contained in trace amounts in the consumer goods, or may be due to compounds that are produced by the interaction of ingredients contained in the consumer goods over time, in some cases due to stimuli such as light (sunlight or room light) or heat. Without being bound by any theory, for example, in the case of milk and fruit juice, it is thought that one or more of the following are the causes of the flavor deterioration: (1) flavor deterioration due to the decomposition of amino acids and proteins, and (2) flavor deterioration due to the oxidation of lipids (photooxidation, etc.). For example, in the case of milk, in the case of (1), methionine contained in milk is oxidized by the action of riboflavin excited by light to produce methional, which is further decomposed into methanethiol, which further produces sulfides, disulfides, trisulfides, etc., and it is thought that the unpleasant flavor is formed by a mixture of the aromas of this methional and the disulfides and trisulfides produced from this compound. In the case of (2), active oxygen generated by photoexcitation of riboflavin contained in milk oxidizes unsaturated fatty acids contained in milk to lipid peroxides, and the volatile aldehydes, ketones, alcohols, etc. generated by decomposition of the lipid peroxides are considered to form unpleasant flavors. (1) produces an unpleasant flavor such as a sulfur-like flavor, and (2) produces an unpleasant flavor such as a fried oil-like flavor, but these unpleasant flavors can be improved by the unpleasant flavor improving composition of the present invention.

[0053] Examples of the unpleasant flavor improving composition of the present invention include various additives for food and beverages, cosmetics, or health and hygiene products, which contain the present compound and can be added to various consumer goods such as food and beverages, cosmetics, and health and hygiene products. The unpleasant flavor improving composition of the present invention can also be used as a flavor imparting composition capable of improving unpleasant flavors, and such use is also included in the unpleasant flavor improving uses of the present invention. More specific examples include, but are not limited to, a flavor composition, various animal and plant extracts, or fermented or heat-treated products of various animal and plant raw materials, which contain the present compound and can be added to various consumer goods. For example, a flavor composition contains a flavor compound as one of the active ingredients, and a flavor compound is a compound that stimulates the sense of smell, but flavor is considered to be a sensation in which olfactory stimulation and gustatory stimulation are integrated in the brain, and olfactory stimulation is combined with a compound that stimulates the sense of taste (such as salt, sugar, and monosodium glutamate) to form the flavor of the entire food, so that a flavor composition can be used to improve the overall flavor of food and beverages.

[0054] The unpleasant flavor improving composition of the present invention may contain, in addition to the present compound, any other components (specific examples will be described later) such as a solvent, a dispersion medium, a flavor-imparting component other than the present compound, and an auxiliary component such as an antioxidant component, but may also consist essentially of the present compound. When the unpleasant flavor improving composition of the present invention contains components other than the present compound, the concentration of the present compound in the unpleasant flavor improving composition can be arbitrarily determined depending on the object to which the unpleasant flavor improving composition is added and the odor characteristics.

[0055] As an example of the concentration of the present compound in the unpleasant flavor improving composition of the present invention, when the unpleasant flavor improving composition of the present invention substantially contains only the present compound and its solvent or dispersion medium (specific examples will be described later), the concentration can be in the range of 10 ppb to 99.9%, and a preferred example can be in the range of 10 ppm to 99.9%.

[0056] As an example of the concentration of the present compound in the unpleasant flavor improving composition of the present invention, particularly when the unpleasant flavor improving composition of the present invention contains a component capable of imparting flavor other than the present compound and its solvent or dispersion medium, the concentration of the present compound in the unpleasant flavor improving composition (preferably the total concentration when a plurality of the present compounds are added) can be arbitrarily determined according to the object to which the unpleasant flavor improving composition is to be added and the flavor characteristics as described above, and may be an appropriate concentration so that the composition can be added to consumer goods at a concentration that exerts an unpleasant flavor improving effect. For example, the concentration may be within the range of 100 ppt to 10%, preferably 1 ppb to 10%, more preferably 100 ppb to 10% based on the total mass of the unpleasant flavor improving composition. More specifically, the lower limit may be any of 100ppt, 1ppb, 10ppb, 100ppb, 1ppm, 10ppb, 100ppm, 0.1%, and 1%, and the upper limit may be any of 10%, 1%, 0.1%, 100ppm, 10ppb, 1ppm, 100ppb, 10ppb, and 1ppb, and the range may be any combination of the lower limit and the upper limit, but is not limited thereto. Although it depends on the formulation of the unpleasant flavor improving composition, when the concentration of the present compound in the unpleasant flavor improving composition is 100ppt to 10%, the unpleasant flavor improving effect on consumer goods can be obtained without the aroma derived from the present compound being excessively prominent. Depending on the unpleasant flavor improving composition of the present invention and the aroma tone of the object to which it is added, the present compound may be added at a concentration outside the range of 100ppt to 10%.

[0057] Specific examples of optional other components that may be contained in the unpleasant flavor improving composition of the present invention in addition to the compound of the present invention include various kinds of flavor compounds, flavor compositions, oil-soluble dyes, vitamins, functional substances, fish meat extracts, livestock meat extracts, animal and plant extracts, yeast extracts, animal and plant proteins, animal and plant protein hydrolysates, starch, dextrin, sugars, amino acids, nucleic acids, organic acids, solvents, etc. For example, natural essential oils, natural flavors, and synthetic flavors described in "Patent Office Gazette, Collection of Well-Known and Commonly Used Technologies (Flavors) Part II Food Flavors, published January 14, 2000," "Survey on the Actual Use of Food Flavor Compounds in Japan" (Health and Welfare Science Research Report FY2000, Japan Flavor and Flavor Manufacturers Association, published March 2001), and "Synthetic Flavors: Chemistry and Product Knowledge" (revised and updated December 20, 2016, edited by the Synthetic Flavors Editorial Committee, Chemical Daily Co., Ltd.) can be mentioned.

[0058] Other examples of fragrance compounds include hydrocarbon compounds such as monoterpenes, such as α-pinene, β-pinene, myrcene, camphene, and limonene, sesquiterpenes, such as valencene, cedrene, caryophyllene, and longifolene, and 1,3,5-undecatriene.

[0059] Examples of the alcohol compound include saturated or unsaturated alcohols such as butanol, pentanol, 3-octanol, hexanol, (Z)-3-hexen-1-ol, prenol, and 2,6-nonadienol; terpene alcohols such as linalool, geraniol, citronellol, tetrahydromyrcenol, farnesol, nerolidol, cedrol, and terpineol; and aromatic alcohols such as benzyl alcohol, phenylethyl alcohol, and cinnamyl alcohol.

[0060] Examples of the aldehyde compound include saturated or unsaturated aldehydes such as acetaldehyde, hexanal, octanal, decanal, and (E)-2-hexenal; terpene aldehydes such as citronellal, hydroxycitronellal, citral, myrtenal, and perillaldehyde; and aromatic aldehydes such as benzaldehyde, cinnamaldehyde, amylcinnamaldehyde, vanillin, ethyl vanillin, heliotropin, and p-tolylaldehyde.

[0061] Examples of the ketone compounds include saturated or unsaturated ketones such as 2-heptanone, 2-undecanone, 1-octen-3-one, and acetoin; diketones and hydroxyketones such as diacetyl, 2,3-pentanedione, maltol, ethyl maltol, cyclotene, and 2,5-dimethyl-4-hydroxy-3(2H)-furanone; terpene ketones such as carvone, menthone, and nootkatone; ketones derived from terpene degradation products such as α-ionone, β-ionone, and β-damascenone; and aromatic ketones such as raspberry ketone.

[0062] Examples of the furan or ether compounds include furfuryl alcohol, furfural, rose oxide, linalool oxide, menthofuran, theaspirane, estragole, eugenol, and 1,8-cineole.

[0063] Examples of the ester compound include aliphatic esters such as ethyl acetate, isoamyl acetate, ethyl butyrate, ethyl isobutyrate, isoamyl butyrate, ethyl 2-methylbutyrate, ethyl 3-methylbutyrate, 2-methylbutyl isobutyrate, ethyl hexanoate, allyl hexanoate, ethyl heptanoate, ethyl caproate, isoamyl isovalerate, and ethyl nonanoate; terpene alcohol esters such as linalyl acetate, geranyl acetate, lavandulyl acetate, and terpenyl acetate; and aromatic esters such as benzyl acetate, benzyl butyrate, methyl salicylate, benzyl salicylate, methyl cinnamate, cinnamyl propionate, ethyl benzoate, cinnamyl isovalerate, and ethyl 3-methyl-2-phenylglycidate.

[0064] Examples of the lactone compound include saturated or unsaturated lactones such as γ-decalactone, γ-dodecalactone, δ-decalactone, δ-dodecalactone, 7-decen-4-olide, and 2-decen-5-olide.

[0065] The acid compounds include saturated or unsaturated fatty acids such as acetic acid, butyric acid, octanoic acid, isovaleric acid, caproic acid, stearic acid, oleic acid, linoleic acid, and linolenic acid.

[0066] Examples of the nitrogen-containing compound include pyridine, alkyl-substituted pyrazine, methyl anthranilate, and trimethylpyrazine.

[0067] Natural essential oils include sweet orange, bitter orange, petitgrain, lemon, bergamot, mandarin, neroli, peppermint, spearmint, lavender, chamomile, rosemary, eucalyptus, sage, basil, rose, hyacinth, lilac, geranium, jasmine, ylang-ylang, anise, clove, ginger, nutmeg, cardamom, cedar, cypress, vetiver, patchouli, labdanum, elderflower, and clary sage.

[0068] Examples of various animal and plant extracts include herb or spice extracts, various tea extracts such as coffee, green tea, black tea, or oolong tea, milk or dairy products, and various enzymatic decomposition products thereof using lipase and / or protease, etc.

[0069] In addition, it may be used in combination with a known material related to improving unpleasant flavors. Examples of such materials include those described in JP 2021-171023 A, JP 2021-142111 A, JP 2021-108822 A, JP 2020-188705 A, JP 2018-87153 A, JP 2015-144621 A, JP 6009616 A, JP 2015-67558 A, Japanese Patent No. 6158664, Japanese Patent No. 2015-67557, Japanese Patent No. 2014-240360, Japanese Patent No. 6216543, Japanese Patent No. 2014-34517, Japanese Patent No. 5220942, Japanese Patent No. 2013-143930, Japanese Patent No. 5019659, Japanese Patent No. 2013-21926, Japanese Patent No. 4925488, Japanese Patent No. 2012-80840, Japanese Patent No. 5198533 Publication No. 2012-80778, No. 6005333, No. 2012-34603, No. 5340238, No. 2011-103873, No. 4562049, No. 2011-223942, No. 5349399, No. 2011-103774, No. 4606505, No. 2008-253217, No. 200 Those described in JP-A-6-104257, JP-4391378, JP-A-2004-248611, JP-4216091, JP-A-2004-18829, JP-A-2003-210119, JP-3830137, JP-A-2003-96486, JP-A-9-221429, JP-3431383, and JP-A-8-119843 may be used.

[0070] Particularly preferred examples of animal and plant extracts that can be used in combination include those obtained by adding appropriate amino acids and sugars to animal and plant extracts and subjecting them to heat treatment (for example, within a range of 80 to 200°C, preferably 100 to 180°C) (for example, JP 2018-102308 A, JP 2018-102309 A, JP 2018-102310 A, JP 2018-102307 A, JP 2017- No. 51206, WO 2016 / 72114, WO 2016 / 72111, WO 2016 / 63394, JP 2015-112038, JP 2013-252111, JP 2013-252113, JP 2013-252112, or JP 2013-252114.

[0071] As described above, the unpleasant flavor improving composition of the present invention can be prepared by adding the present compound to an appropriate solvent or dispersion medium by a known method, and the unpleasant flavor improving composition of the present invention is preferably in the form of a solution in which the present compound or other components are dissolved in a water-soluble or oil-soluble solvent, an emulsion preparation, a powder preparation, or other solid preparation (solid fat, etc.). There is no particular restriction on the type of solvent or dispersion medium used, but for example, the following can be used.

[0072] Examples of water-soluble solvents include ethanol, methanol, acetone, tetrahydrofuran, acetonitrile, 2-propanol, methyl ethyl ketone, glycerin, ethylene glycol, propylene glycol, dipropylene glycol, hexyl glycol, benzyl benzoate, triethyl citrate, diethyl phthalate, etc. Among these, ethanol or propylene glycol is particularly preferred when used in food and beverages. Examples of oil-soluble solvents include vegetable oils and fats, animal oils and fats, refined oils and fats (e.g., processed oils and fats such as medium-chain fatty acid triglycerides, and short-chain fatty acid triglycerides such as triacetin and tripropionin), hercolin, various essential oils, triethyl citrate, etc.

[0073] In addition, to prepare an emulsion preparation, the present compound can be emulsified with a water-soluble solvent and an emulsifier.The emulsification method of the present compound is not particularly limited, and can be obtained by emulsifying with various emulsifiers that have been used in food and beverages, such as fatty acid monoglycerides, fatty acid diglycerides, fatty acid triglycerides, propylene glycol fatty acid esters, sucrose fatty acid esters, polyglycerin fatty acid esters, lecithin, chemically modified starch, sorbitan fatty acid esters, Quillaja extract, gum arabic, tragacanth gum, guar gum, karaya gum, xanthan gum, pectin, alginic acid and its salts, carrageenan, gelatin, casein, Quillaja saponin, sodium caseinate, etc., using a homomixer, colloid mill, rotating disk homogenizer, high pressure homogenizer, etc., to obtain an emulsion with excellent stability. The amount of these emulsifiers used is not strictly limited and can be changed over a wide range depending on the type of emulsifier used, but is usually within the range of about 0.01 to about 100 parts by mass, preferably about 0.1 to about 50 parts by mass, per part by mass of the compound of the present invention. In order to stabilize the emulsion, the water-soluble solvent solution may contain, in addition to water, one or a mixture of two or more polyhydric alcohols such as glycerin, propylene glycol, sorbitol, maltitol, sucrose, glucose, trehalose, sugar solution, and reduced starch syrup.

[0074] The emulsion thus obtained can be dried to produce a powder formulation, if desired. When producing the powder, sugars such as gum arabic, trehalose, dextrin, sugar, lactose, glucose, starch syrup, and reduced starch syrup can be added as needed. The amount of these to be used can be appropriately selected depending on the desired properties of the powder formulation.

[0075] [Method of producing composition for improving unpleasant flavor] As one aspect of the present invention, there is provided a method for producing an unpleasant flavor improving composition, which comprises adding the present compound to any composition that can be added to various consumer goods. Examples of compositions that can be added to various consumer goods include compositions containing one or more selected from solvents, antioxidants, colorants, and other additives that can be added to foods and beverages, fragrances and cosmetics, and health and hygiene products. Furthermore, as another aspect of the present invention, the unpleasant flavor improving composition of the present invention can be added to another flavor-imparting composition to produce the flavor-imparting composition to be added as an unpleasant flavor improving composition. The unpleasant flavor improving composition of the present invention produced in this way can be used in the production of various consumer goods as an additive composition for various consumer goods such as foods and beverages, fragrances and cosmetics, and health and hygiene products.

[0076] [Method for improving unpleasant flavor of consumer goods and consumer goods] By adding the unpleasant flavor improving composition of the present invention to various consumer goods such as food and beverages, fragrances and cosmetics, and health and hygiene products, consumer goods with improved unpleasant flavors are produced. Therefore, in the present invention, the method for improving unpleasant flavors in various consumer goods can also be said to be a method for producing consumer goods with improved unpleasant flavors. The timing of adding the unpleasant flavor improving composition to various consumer goods is arbitrary, and the unpleasant flavor improving composition itself may be added to various consumer goods such as food and beverages, fragrances and cosmetics, and health and hygiene products, or it may be added to various consumer goods together with one or more other flavor-imparting compositions (for example, one or more selected from a water-soluble flavor composition, an emulsified flavor composition, any flavor compound, and a natural essential oil (for example, a flavor compound described in the above-mentioned "Japan Patent Office Gazette, Collection of Well-Known and Commonly Used Technology (Flavors) Part II Food Flavors," "Survey on the Actual Use of Food Flavor Compounds in Japan," and "Synthetic Flavors: Chemistry and Product Knowledge")).

[0077] Foods and beverages to which the unpleasant flavor improving composition of the present invention can be added are not particularly limited, and may have any flavor (also referred to as taste). Examples of flavors include various citrus flavors such as lemon, orange, grapefruit, lime, mandarin, mandarin orange, kabosu, sudachi, hassaku, iyokan, yuzu, shikuwasa, and kumquat; various fruit flavors such as strawberry, blueberry, raspberry, apple, cherry, plum, apricot, peach, pineapple, banana, melon, mango, papaya, kiwi, pear, grapes (grape, muscat, Kyoho, etc.), lychee, and passion fruit; milk flavors or flavors containing a milk flavor such as milk, yogurt, butter, and custard; vanilla flavor; various tea flavors such as green tea, matcha, roasted tea, black tea, oolong tea, barley tea, corn tea, buckwheat tea, pu-erh tea, and herbal tea; coffee flavor; cola flavor; cacao flavor; flavors; various mint flavors such as spearmint and peppermint; various spice or herb flavors such as cinnamon, chamomile, cardamom, caraway, cumin, cloves, pepper, coriander, Japanese pepper, shiso, ginger, star anise, thyme, chili pepper, nutmeg, basil, marjoram, rosemary, laurel, wasabi, Japanese pepper, and garlic; various nut flavors such as almond, cashew nut, and walnut; various alcoholic beverage flavors such as wine, brandy, whiskey, rum, gin, liqueur, sake, shochu, and beer; vegetable flavors such as carrot, tomato, cucumber, onion, corn, and potato; meat flavors such as chicken, pork, beef, lamb, and horse meat; seafood flavors; broth (bouillon) flavors of vegetables, meat, and seafood; consomme flavor; and caramel flavor.That is, the food or beverage may be one that imparts only one of the above flavors, or two or more flavors, and the multiple flavors may be similar or different. For example, examples of the former include foods and beverages that impart multiple fruit flavors such as banana, peach and apple flavors among other fruit flavors (so-called mixed fruit flavors), and examples of the latter include foods and beverages that impart a citrus flavor such as lemon and a milky flavor (such as a citrus-flavored lactic acid bacteria drink), and foods and beverages that impart a mint flavor or a citrus flavor and a cola flavor (such as a mint or lemon-flavored cola drink), but the unpleasant flavor may be any flavor that can be improved by the unpleasant flavor improving composition of the present invention.

[0078] More specific examples of food and drink include rice crackers, arare, okoshi, mochi, manju, uiro, bean paste, yokan, mizuyokan, kingyoku, jelly, castella, candy, biscuits, crackers, potato chips, cookies, pies, puddings, ice cream, ice milk, butter cream, custard cream, cream puffs, waffles, sponge cakes, donuts, chocolate, chewing gum, caramel, candy, peanut paste, etc. or other pastes, whipped cream and other confectioneries or confectionery ingredients; bread, udon, ramen, Chinese noodles, sushi, gomoku-meshi, fried rice, pilaf, gyoza wrappers, shumai wrappers, okonomiyaki, takoyaki and other breads, noodles, rice dishes and other grains; pickles such as bran-pickled plums, fukujin-zuke, bettara-zuke, senma-zuke, rakkyo, miso-zuke, takuan-zuke and the bases for these pickles; mackerel, sardines, pacific saury, salmon, tuna, bonito, whale, turtle, etc. Seafood such as ray, sand lance, sweetfish, squid such as pacific flying squid, spear squid, crested squid, firefly squid, octopus such as common octopus and Japanese octopus, shrimp such as kuruma shrimp, button shrimp, spiny lobster, black tiger prawn, crab such as king crab, snow crab, blue crab, hairy crab, shellfish such as clams, mussels, scallops, oysters, mussels, etc.; livestock meat such as chicken, pork, beef, lamb, horse meat; canned goods, boiled fish, tsukudani, surimi, fish paste products (chikuwa, kamaboko, Deep-fried fish cake, crab leg fish cake, etc.), fries, tempura, curry, stew, beef stew, hayashi rice sauce, meat sauce, mapo tofu, hamburger steak, dumplings, kamameshi seasoning, soups (corn soup, tomato soup, consommé soup, etc.), meatballs, braised pork, canned meat, boiled vegetables, Chikuzen-ni, oden, hotpots, takeaway side dishes, ramen, soba, udon, somen, and other noodles and the soups used for them, vegetable soups, and other processed foods made from animal and plant ingredients;Table salt, seasoning salt, soy sauce, powdered soy sauce, miso, powdered miso, moromi, hisio, furikake, ochazuke seasoning, margarine, mayonnaise, dressing, vinegar, sanbai-zu, powdered sushi vinegar, Chinese seasoning, tempura sauce, noodle sauce (kelp stock or bonito stock, etc.), sauce (medium-thick sauce, tomato sauce, etc.), ketchup, yakiniku sauce, curry roux, stew seasoning, soup seasoning, dashi seasoning (kelp stock or bonito stock, etc.), compound seasoning, new mirin, mixed powders such as fried chicken powder and takoyaki powder, etc. Seasonings such as these, and animal or vegetable broth-flavored foods and beverages with these seasonings added; dairy products such as cheese, yogurt, butter, and fresh cream; fruit drinks made from fruit juice, pulp, grains, and peels of apples, grapes, mangoes, peaches, and citrus fruits (grapefruit, oranges, lemons, etc.); vegetables such as tomatoes, bell peppers, celery, gourds, bitter melons, carrots, potatoes, asparagus, bracken, and fern, as well as vegetable drinks and vegetable soups containing these vegetables. Food and drink containing vegetables; coffee, cocoa, green tea, black tea, oolong tea, soft drinks, carbonated drinks, cola drinks, lactic acid bacteria drinks, milk-containing drinks (milk tea, cafe au lait, etc.), fruit or fruit juice drinks (fruit tea such as lemon tea and orange tea, etc.); beverages containing herbal medicines or herbs; functional drinks such as cola drinks, sports drinks, honey drinks, vitamin supplement drinks, mineral supplement drinks, nutritional drinks, and nutritious drinks; non-alcoholic beverages such as alcohol-flavored drinks with various alcohol flavors (beer flavor, plum wine flavor, chuhai flavor, etc.) (non-alcoholic beer, non-alcoholic chuhai, etc.); beer-flavored drinks (also called beer-flavored drinks) including wine, shochu, awamori, sake, beer, chuhai, cocktail drinks, happoshu, fruit wine, condiment wine, so-called "third beer", other brewed alcohol (sparkling), liqueur (sparkling), or alcoholic drinks containing these;

[0079] Particularly suitable examples of the food and drink to which the unpleasant flavor improving composition of the present invention is added include the food and drink containing milk or fruit juice.Examples of the food and drink containing milk include milk itself, such as cow's milk, goat's milk, sheep's milk, horse's milk, etc., and various dairy products using these milks.Specific examples of dairy products include, but are not limited to, ingredient-adjusted milk, processed milk, skim milk, skim concentrated milk, lactic acid bacteria drink, milk drink, fermented milk (yogurt, etc.), butter, cheese, cream, ice cream, condensed milk, milk powder, whey powder, buttermilk powder, and various drinks containing or produced using these (such as various tea drinks containing milk, such as milk tea). Examples of fruit juices include juices of the various fruits mentioned above (various citrus flavors such as lemon, orange, grapefruit, lime, mandarin, mandarin orange, kabosu, sudachi, hassaku, iyokan, yuzu, shikuwasa, and kumquat, and various fruit flavors such as apple, strawberry, blueberry, raspberry, apple, cherry, plum, apricot, peach, pineapple, banana, melon, mango, papaya, kiwi, pear, grapes (grape, muscat, Kyoho, etc.), lychee, and passion fruit), and particularly preferred are mango, peach, grape, apple, orange, and mandarin orange.

[0080] The cosmetic products and health and hygiene products to which the unpleasant flavor improving composition of the present invention can be added are not particularly limited, and may have any flavor. More specific examples of the cosmetic products and health and hygiene products include perfumes such as eau de cologne, eau de toilette, eau de parfum, and parfum; hair care products such as shampoo, rinse, and hair styling products (hair cream, pomade, etc.); cosmetics such as foundation, lipstick, lip balm, lip gloss, lotion, cosmetic emulsion, cosmetic cream, cosmetic gel, beauty essence, and pack; various preparations for suppressing scalp odor (scalp care agents, etc.), various preparations for suppressing body odor (antiperspirant sprays, deodorant sheets, deodorant creams, deodorant sticks, etc.), preparations for suppressing bad breath (mouthwash, toothpaste, oral hygiene products, etc.), and the like. Examples of such products include deodorant products such as face masks with odor-preventing effects, deodorant products such as face washes, ...

[0081] Particularly suitable examples of cosmetic products and health and hygiene products to which the unpleasant flavor improving composition of the present invention can be added include various products that can be used to suppress unpleasant odors, such as perfumes, hair care products, deodorant products, health and hygiene detergents, health and hygiene materials, and deodorants.

[0082] The concentration of the present compound in various consumer goods such as foods and beverages, cosmetics, and health and hygiene products to which the unpleasant flavor improving composition of the present invention has been added can be determined arbitrarily depending on the flavor of the consumer goods and the degree of the desired effect.

[0083] The inventors have confirmed that the unpleasant flavor of food and drink can be improved when the concentration of the present compound is in the range of 10ppt to 1% relative to the total mass of the food and drink. For example, the lower limit may be any of 10ppt, 100ppt, 1ppb, 10ppb, 100ppb, 1ppm, 10ppb, 100ppm, and 0.1%, and the upper limit may be any of 1%, 0.1%, 100ppm, 10ppb, 1ppb, 10ppb, 1ppb, and 100ppt, and the range may be any combination of the lower limit and upper limit values, but is not limited to these concentration ranges. Specific examples of preferred concentration ranges include the ranges of 1ppb to 100ppm, 1ppb to 10ppm, 10ppb to 10ppm, and 10ppb to 100ppm. Particularly preferably, the concentration is within the range of 1 ppb to 100 ppm, and more preferably, 10 ppb to 100 ppm. Within this range, particularly when the present compound is a compound of each of the formulae A-1 to A-10 and B-1 to B-4, unpleasant flavors can be improved and a suitable flavor can be imparted to consumer goods. Note that, although it depends on the flavor characteristics of the food or drink to which the unpleasant flavor improving composition of the present invention is added, the processing conditions (temperature, pH, etc.) during the production of the food or drink, the temperature at the time of eating, etc., when the concentration of the present compound in the food or drink is within the range of 10 ppt to 1%, the unpleasant flavor of the food or drink to which the composition is added can be improved without the aroma of the compound itself being excessively prominent. For example, the concentration relative to the total mass of the food or drink can be adjusted within the range of 10 ppt to 1% depending on the type of the present compound. Depending on the flavor characteristics of the food or drink to which the composition is added, the processing conditions (temperature, pH, etc.) during the production of the food or drink, the temperature at the time of eating, etc., the present compound may be added at a concentration below the lower limit or above the upper limit. The concentrations exemplified in this paragraph are preferably the total concentrations when multiple compounds of the present invention are added.

[0084] As for cosmetics and health care products, the unpleasant odor of the product can be improved by manufacturing a cosmetics or health care product containing the compound of the present invention at any concentration and adding it to an object that exhibits an unpleasant odor. The inventors have confirmed that the unpleasant odor of the object can be improved when the concentration of the compound of the present invention is in the range of 100ppt to 10% relative to the total mass of the object that exhibits an unpleasant odor. More specifically, the lower limit is any of 100ppt, 1ppb, 10ppb, 100ppb, 1ppm, 10ppm, 100ppm, 0.1%, and 1%, and the upper limit is any of 10%, 1%, 0.1%, 100ppm, 10ppb, 1ppm, 100ppb, 10ppb, and 1ppb, and the range can be any combination of the lower limit and upper limit values, but is not limited to these. As an example of a preferred concentration, the concentration of the present compound relative to the total mass of the target can be selected from the following ranges according to the aroma characteristics of the target, but is not limited thereto. Although it depends on the type and aroma of the target, when the concentration of the present compound in the target is 100ppt to 10%, the unpleasant odor of the target can be improved without the odor of the compound itself being excessively prominent. Depending on the aroma characteristics of the target, the present compound may be added at a concentration below the lower limit or above the upper limit. When multiple compounds of the present compound are added, the concentration exemplified in this paragraph is preferably the total concentration of the compounds. EXAMPLES

[0085] The present invention will be described in more detail below with reference to examples, although the present invention is not limited to these.

[0086] [Example 1] Confirmation of unpleasant flavor improving effect 1 A commercially available lactic acid bacteria drink (pH 3.6) was prepared. As specific examples of the present compound, the commercially available compounds of formulas A-1 to A-10 and formulas B-1 to B-4 were dissolved in 95% ethanol to prepare ethanol solutions of the present compound at arbitrary concentrations, which were used as the unpleasant flavor improving compositions of the present invention (Products 1-1 to 1-14 of the present invention).

[0087] [Table 1]

[0088] On the other hand, as a comparative example, a commercially available furfural was dissolved in 95% ethanol to prepare a comparative composition (Comparative Product 1-1).

[0089] Next, the present invention products 1-1 to 1-14 were added to the commercially available lactic acid bacteria beverage so that the concentration of the present compound was 10ppt, 1ppm, and 1%, respectively, to obtain the lactic acid bacteria beverages that are one embodiment of the consumer goods of the present invention (the present invention products 1-15 to 1-56). In addition, the comparative product 1-1 was added to the commercially available lactic acid bacteria beverage so that the concentration of furfural was 1ppm, to obtain the comparative lactic acid bacteria beverage (comparative product 1-2). Next, the commercially available lactic acid bacteria beverages and the present invention and comparative lactic acid bacteria beverages were placed in a transparent container with a lid and subjected to light abuse under the following conditions. (Light abuse conditions) Transparent containers filled with the commercially available product, the product of the present invention, and the comparative product lactic acid bacteria beverages and then covered were placed in an environment of 35,000 lux / h and 10°C and subjected to light abuse for 72 hours (cumulative 2.52 million lux).

[0090] Sensory evaluation was performed on the aroma of the headspace of the commercially available lactic acid bacteria beverages of the present invention and the comparative product after light abuse treatment. In the sensory evaluation, the aromas of the present invention products 1-15 to 1-56 and the comparative product 1-2 were compared with a commercially available lactic acid bacteria beverage (Comparative product 1) after light abuse that did not contain either the unpleasant flavor imparting composition of the present invention or the comparative product composition, and 12 well-trained panelists with 10 years or more of experience were asked to evaluate them. In the evaluation, the unpleasant aromas of the aromas of the present invention and the comparative products were scored according to the following criteria, and the panelists were also asked to freely comment on the aromas that were felt to be different from the comparative product 1. (Standard) Unpleasant odor compared to the control product "Much improved" = 4 points "Improved" = 3 points "Slightly improved" = 2 points "No improvement felt" = 1 point "The unpleasant smell was felt more strongly" = 0 points Table 2 shows the average scores and representative comments of the 12 panelists.

[0091] [Table 2]

[0092] As shown in Table 2, it was confirmed that the unpleasant odor could be improved compared to the control product by adding an unpleasant odor improving composition containing, as an active ingredient, each of the compounds of the formulae A-1 to A-10 and B-1 to B-4, which are examples of the present compound. In addition to being less sensitive to sulfur-like or fried oil-like unpleasant odors compared to the control product, the present invention products 1-15 to 1-56 each had a good milky odor that was impaired by the unpleasant odor in the control product, and thus had an improved flavor compared to the control product.

[0093] [Example 2] Confirmation of unpleasant flavor improving effect 2 A commercially available peach juice (30% fruit juice, pH 3.5) was prepared and used as control product 2. In addition, the peach juice of the present invention was obtained in the same manner as in Example 1, except that the commercially available lactic acid bacteria beverage was replaced with peach juice (Products 2-1 to 2-42 of the present invention). In addition, the ethanol solution of furfural prepared in Example 1 (Comparative Product 1-1) was added to the commercially available peach juice so that the concentration of furfural was 1 ppm, to obtain a comparative peach juice (Comparative Product 2-1).

[0094] Next, the peach juices of the commercially available product, the product of the present invention, and the comparative product were subjected to light abuse under the same conditions as in Example 1 below. (Light abuse conditions) Transparent containers filled with peach juice from the commercially available product, the product of the present invention, and the comparative product and then covered were placed in an environment of 35,000 lux / h and 10°C and subjected to light abuse for 72 hours (accumulated 2.52 million lux).

[0095] Then, the headspace aromas sensed from the light-affected peach juices of control product 2 (commercially available peach juice), invention products 2-1 to 2-42, and comparative product 1-2 were subjected to sensory evaluation in the same manner as in Example 1. Table 3 shows the average scores and representative comments of the 12 panelists.

[0096] [Table 3]

[0097] As shown in Table 3, it was confirmed that the unpleasant odor could be improved compared to the control product by adding an unpleasant odor improving composition containing the compounds of formulae A-1 to A-10 and B-1 to B-4, which are examples of the present compound, as active ingredients. In addition, the present invention products 2-1 to 2-42 were less likely to have a sulfur-like unpleasant odor compared to the control product, and had a good peach-like fruity flavor that was impaired by the unpleasant odor in the control product, and the flavor was improved compared to the control product. In particular, in the case of the compounds of formula B (compounds of formulae B-1 to B-4), a fruity sweetness was imparted, and the flavor of peach juice was superior to that when the compounds of formula A (compounds of formulae A-1 to A-10) were added.

[0098] [Example 3] Confirmation of unpleasant flavor improving effect 3 Instead of the commercially available lactic acid bacteria drink, a commercially available yogurt drink (pH 4.1) was used, and the unpleasant flavor improving compositions (Products 1-1 to 1-4, 1-8, 1-9, 1-11 to 1-14) containing each of the 10 compounds of formulae A-1, A-2, A-3, A-4, A-8, A-9, B-1, B-2, B-3, and B-4 were used as the present compounds. The concentrations of these compounds were set to the concentrations shown in Table 4 below. The milk-flavored beverages of the present invention were prepared in the same manner as in Example 1 (Products 3-1 to 3-40 of the present invention). Then, light aging was performed under the same conditions as in Example 1. Next, a sensory evaluation was performed on the flavor of the light-aged products of the present invention 3-1 to 3-40 compared to the flavor of the light-aged product of the commercially available yogurt drink (Control Product 3). In the sensory evaluation, 12 well-trained panelists with 10 years or more of experience were asked to evaluate the flavors felt when consuming the products of the present invention 3-1 to 3-40, compared with the flavor felt when consuming a commercially available yogurt drink (control product 3) after light abuse to which the compound of the present invention was not added. In the evaluation, the panelists were asked to score the unpleasant flavor of the products of the present invention according to the following criteria, and to freely comment on the flavors felt to be different from control product 3. (Standard) Unpleasant flavor compared to the control product "Much improved" = 4 points "Improved" = 3 points "Slightly improved" = 2 points "No improvement felt" = 1 point "Unpleasant flavor was felt more strongly" = 0 points Table 4 shows the average scores and representative comments of the 12 panelists.

[0099] [Table 4]

[0100] As shown in Table 4, it has been confirmed that each of the ten compounds of formulae A-1, A-2, A-3, A-4, A-8, A-9, B-1, B-2, B-3, and B-4, which are examples of the present compound, can improve unpleasant flavors not limited to the foods and beverages of Examples 1 and 2.

[0101] [Example 4] Confirmation of unpleasant flavor improving effect 4 Instead of the commercially available yogurt drink, commercially available milk tea (pH 6.8), commercially available orange juice (100% fruit juice, pH 3.7), and commercially available mango juice (100% fruit juice, pH 3.7) were prepared, and the unpleasant flavor improving compositions (Products of the present invention 1-1 to 1-4, 1-8, 1-9, 1-11 to 1-14) containing each of the 10 compounds of formulae A-1, A-2, A-3, A-4, A-8, A-9, B-1, B-2, B-3, and B-4 were used as the present compound, and the concentrations of these compounds of the present invention were 1 ppm relative to the total mass of the commercially available milk tea, orange juice, or mango juice as shown in Table 5. The milk tea of ​​the present invention (Products of the present invention 4-1 to 4-10), the orange juice of the present invention (Products of the present invention 4-11 to 4-20), and the mango juice of the present invention (Products of the present invention 4-21 to 4-20) were prepared in the same manner as in Example 3. Then, light aging was carried out under the same conditions as in Example 1. Next, the flavors of the products of the present invention 4-1 to 4-10 compared with the flavor of the commercially available light-aged milk tea (control product 4-1), the flavors of the products of the present invention 4-11 to 4-20 compared with the flavor of the commercially available light-aged orange juice (control product 4-2), and the flavors of the products of the present invention 4-21 to 4-30 compared with the flavor of the commercially available light-aged mango juice (control product 4-3) were subjected to sensory evaluation by 12 well-trained panelists with more than 10 years of experience. In the sensory evaluation, the unpleasant flavors of the products of the present invention compared with the control products were scored according to the following criteria, and the participants were also allowed to freely comment on the flavors that were felt to be different from each control product. (Standard) Unpleasant flavor compared to the control product "Much improved" = 4 points "Improved" = 3 points "Slightly improved" = 2 points "No improvement felt" = 1 point "Unpleasant flavor was felt more strongly" = 0 points Table 5 shows the average scores and representative comments of the 12 panelists.

[0102] [Table 5]

[0103] As shown in Table 5, it has been confirmed that each of the ten compounds of formulae A-1, A-2, A-3, A-4, A-8, A-9, B-1, B-2, B-3, and B-4, which are examples of the present compound, can improve unpleasant flavors not limited to the foods and beverages of Examples 1 to 3.

[0104] [Example 5] Confirmation of unpleasant flavor improving effect 5 The commercially available lactic acid bacteria beverage used in Example 1, as well as commercially available mango juice (100% fruit juice, pH 3.7) and grape juice (100% fruit juice, pH 3.5) were prepared and placed in the same transparent container with a lid as in Example 1, and subjected to light abuse under the same conditions as in Example 1. Then, in the same manner as in Example 3, unpleasant flavor improving compositions containing each of the 10 compounds of formulae A-1, A-2, A-3, A-4, A-8, A-9, B-1, B-2, B-3, and B-4 (Products 1-1 to 1-4, 1-8, 1-9, 1-11 to 1-14) were used as the present compounds, and the concentrations of these compounds were added to the lactic acid bacteria beverage, mango juice, or grape juice after light abuse to the concentrations shown in Table 6 below, to obtain the lactic acid bacteria beverage of the present invention (Products 5-1 to 5-10 of the present invention), the mango beverage of the present invention (Products 5-11 to 5-20 of the present invention), and the grape beverage of the present invention (Products 5-21 to 5-30 of the present invention). Then, sensory evaluation was performed on each of the obtained beverages of the present invention. In the sensory evaluation, the flavors of the present invention products 5-1 to 5-10 compared with the flavor of a commercially available lactic acid bacteria drink that was abused by light (control product 5-1), the flavors of the present invention products 5-11 to 5-20 compared with the flavor of a commercially available mango juice that was abused by light (control product 5-2), and the flavors of the present invention products 5-21 to 5-30 compared with the flavor of a commercially available grape juice that was abused by light (control product 5-3) were evaluated by 12 well-trained panelists with more than 10 years of experience. In the evaluation, the unpleasant flavors of the present invention products were scored according to the following criteria, and the panelists were also allowed to freely comment on the flavors that were felt to be different from each control product. (Standard) Unpleasant odor compared to the control product "Much improved" = 4 points "Improved" = 3 points "Slightly improved" = 2 points "No improvement felt" = 1 point "Unpleasant flavor was felt more strongly" = 0 points Table 6 shows the average scores and representative comments of the 12 panelists.

[0105] [Table 6]

[0106] As shown in Table 6, it has been confirmed that each of the ten compounds of formulae A-1, A-2, A-3, A-4, A-8, A-9, B-1, B-2, B-3, and B-4, which are examples of the present compound, can improve unpleasant flavors not limited to the foods and beverages of Examples 1 to 4.

[0107] [Summary of the Examples] As shown in Examples 1 to 5, the unpleasant flavor improving composition of the present invention can improve the unpleasant flavor of a consumer good by adding it to the consumer good. In particular, since it is useful for improving an unpleasant flavor having a sulfur-like flavor, it is useful for improving the unpleasant odor of an article in which a sulfur-like flavor causes an unpleasant odor, typically food and drink, bad breath, body odor, etc.

Claims

1. A composition for improving unpleasant flavors, comprising as an active ingredient at least one cyclic ketone compound selected from the compounds described in Group A below. (Group A) Cyclic ketone compounds represented by the following formula A 【Chemistry 1】 [In the formula, n represents 0 or 1, the dashed line represents a single bond or a double bond, and when the dashed line on the ring represents a double bond, R １ and R ２ is a hydroxy group and the other is a hydrogen atom, a methyl group, or an ethyl group, and the dashed line on the ring is a single bond, R １ and R ２ is an oxygen atom bonded to a carbon atom on the ring by a double bond on one side, and a hydrogen atom, a methyl group, or an ethyl group on the other side, and R ３ and R ４ are each independently hydrogen, a methyl group, or an ethyl group. (Note that n=0, the dashed line on the ring represents a double bond, and R １ is a hydroxy group, R ２ is a methyl group, R ３ and R ４ is hydrogen; n=0, the dashed line on the ring is a double bond, R １ is a hydroxy group, R ２ is an ethyl group, R ３ and R ４ is hydrogen; n=0, the dashed line on the ring is a single bond, R １ is oxygen, R ２ is a methyl group, R ３ and R ４ is hydrogen; n=0, the dashed line on the ring is a single bond, R 1 is oxygen, R 2 is ethyl, R 3 and R 4 are hydrogen; n=0, the dashed line on the ring is a single bond, R 1 is oxygen, R 2 and R 3 are methyl, R 4 is hydrogen; n=0, the dashed line on the ring is a double bond, R 1 is a hydroxyl group, R 2 and R 3 are methyl, R 4 is hydrogen; n=0, the dashed line on the ring is a double bond, R 1 is a hydroxyl group, R 2 is hydrogen, R 3 and R 4 are methyl; n=0, the dashed line on the ring is a single bond, R 1 is hydrogen, R 2 is oxygen, R 3 and R 4 are methyl; n=0, the dashed line on the ring is a double bond, R 1 is hydrogen, R 2 is oxygen, R 3 and R 4 are methyl; n=0, the dashed line on the ring is a double bond, R 1 is hydrogen, R 2 is oxygen, R 3 and R 4 are methyl; is a methyl group.)

2. 2. The unpleasant flavor improving composition according to claim 1, wherein the group A is a group consisting of compounds represented by the following formula Aa and compounds represented by the following formula Ab: 【Chemistry 2】 [In the formula, the dashed line represents a single bond or a double bond, and when the dashed line on the ring represents a double bond, Ra １ is a hydroxy group, Ra ２ is hydrogen, a methyl group, or an ethyl group, and when the dashed line on the ring is a single bond, Ra １ is an oxygen atom bonded to a carbon atom on the ring by a double bond, ２ is hydrogen, a methyl group or an ethyl group, and Ra ３ and Ra ４ are each independently hydrogen, a methyl group, or an ethyl group. (Note that the dashed line on the ring indicates a double bond, and Ra １ is a hydroxy group, Ra ２ is a methyl group, Ra ３ and Ra ４ is hydrogen; the dashed line on the ring is a double bond, Ra １ is a hydroxy group, Ra ２ is an ethyl group, Ra ３ and Ra ４ is hydrogen; the dashed line on the ring is a single bond, Ra １ is oxygen, Ra ２ is a methyl group, Ra ３ and Ra ４ is hydrogen; the dashed line on the ring is a single bond, Ra 1 is oxygen, Ra 2 is an ethyl group, and Ra 3 and Ra 4 are hydrogen; the dashed line on the ring is a single bond, Ra 1 is oxygen, Ra 2 and Ra 3 are methyl groups, and Ra 4 is hydrogen; the dashed line on the ring is a double bond, Ra 1 is a hydroxy group, Ra 2 and Ra 3 are methyl groups, and Ra 4 is hydrogen; and the dashed line on the ring is a double bond, Ra 1 is a hydroxy group, Ra 2 is hydrogen, and Ra 3 and Ra 4 are methyl groups.) 【Chemistry 3】 [In the formula, the dashed line represents a single bond or a double bond, and when the dashed line on the ring represents a double bond, Rb １ is a hydroxy group, Rb ２ is hydrogen, a methyl group, or an ethyl group, and when the dashed line on the ring is a single bond, Rb １ is an oxygen atom bonded to a carbon atom on the ring by a double bond, Rb ２ is hydrogen, a methyl group or an ethyl group, and Ra ３ and Ra ４ are each independently a hydrogen atom, a methyl group, or an ethyl group; Rb ５ is hydrogen.]

3. 3. The unpleasant flavor improving composition according to claim 1, wherein the compound belonging to Group A is a compound selected from the following formulae A-4 to A-10. 【Chemistry 4】

4. 4. The unpleasant flavor improving composition according to claim 1, wherein the unpleasant flavor is an unpleasant flavor derived from a milk component and / or an unpleasant flavor derived from a fruit juice component.

5. The unpleasant flavor improving composition according to any one of claims 1 to 4, wherein the unpleasant flavor is a photodeterioration odor of milk or a photodeterioration odor of fruit juice.

6. The unpleasant flavor improving composition according to any one of claims 1 to 5, which further exerts the effect of imparting a sweet flavor.

7. 7. The unpleasant flavor improving composition according to claim 1, further comprising a keto-enol tautomer corresponding to each of the compounds in Group A contained in the unpleasant flavor improving composition.

8. A method for producing a composition for improving an unpleasant flavor, comprising adding at least one compound selected from the compounds described in Group A below to a composition that can be added to consumer goods. (Group A) Cyclic ketone compounds represented by the following formula A 【Chemistry 5】 [In the formula, n represents 0 or 1, the dashed line represents a single bond or a double bond, and when the dashed line on the ring represents a double bond, R １ and R ２ is a hydroxy group and the other is a hydrogen atom, a methyl group, or an ethyl group, and the dashed line on the ring is a single bond, R １ and R ２ is an oxygen atom bonded to a carbon atom on the ring by a double bond on one side, and a hydrogen atom, a methyl group, or an ethyl group on the other side, and R ３ and R ４ are each independently hydrogen, a methyl group, or an ethyl group. (Note that n=0, the dashed line on the ring represents a double bond, and R １ is a hydroxy group, R ２ is a methyl group, R ３ and R ４ is hydrogen; n=0, the dashed line on the ring is a double bond, R １ is a hydroxy group, R ２ is an ethyl group, R ３ and R ４ is hydrogen; n=0, the dashed line on the ring is a single bond, R １ is oxygen, R ２ is a methyl group, R ３ and R ４ is hydrogen; n=0, the dashed line on the ring is a single bond, R 1 is oxygen, R 2 is ethyl, R 3 and R 4 are hydrogen; n=0, the dashed line on the ring is a single bond, R 1 is oxygen, R 2 and R 3 are methyl, R 4 is hydrogen; n=0, the dashed line on the ring is a double bond, R 1 is a hydroxyl group, R 2 and R 3 are methyl, R 4 is hydrogen; n=0, the dashed line on the ring is a double bond, R 1 is a hydroxyl group, R 2 is hydrogen, R 3 and R 4 are methyl; n=0, the dashed line on the ring is a single bond, R 1 is hydrogen, R 2 is oxygen, R 3 and R 4 are methyl; n=0, the dashed line on the ring is a double bond, R 1 is hydrogen, R 2 is oxygen, R 3 and R 4 are methyl; n=0, the dashed line on the ring is a double bond, R 1 is hydrogen, R 2 is oxygen, R 3 and R 4 are methyl; is a methyl group.)

9. A method for improving an unpleasant flavor in a consumer good, comprising blending the unpleasant flavor improving composition according to any one of claims 1 to 7 into the consumer good.

10. 10. A method for improving an unpleasant flavor of a consumer good according to claim 9, comprising blending the unpleasant flavor improving composition according to any one of claims 1 to 7 into a consumer good at a final concentration such that the concentration of the cyclic ketone compound selected from Group A is in the range of 10 ppb to 1%, wherein the consumer good is a food or beverage.

11. The method for improving unpleasant flavors in consumer goods according to claim 10, wherein the concentration range is 10 ppb to 10 ppm.

12. The method for improving an unpleasant flavor of a consumer product according to claim 10 or 11, wherein the food or drink contains milk and / or fruit juice.

13. A consumer product comprising the unpleasant flavor improving composition according to any one of claims 1 to 7 added thereto.

14. A composition for improving an unpleasant flavor, comprising at least one cyclic ketone compound selected from the compounds in Group A below as an active ingredient, The unpleasant flavor improving composition, wherein the unpleasant flavor is an unpleasant flavor derived from a milk component and / or an unpleasant flavor derived from a fruit juice component. (Group A) Cyclic ketone compounds represented by the following formula A 【Chemistry 6】 [wherein n is 0, the dashed line represents a single bond or a double bond, and when the dashed line on the ring is a double bond, R 1 is a hydroxy group, R 2 is an ethyl group, and when the dashed line on the ring is a single bond, R 1 is an oxygen bonded to a carbon on the ring by a double bond, R 2 is an ethyl group, and R 3 and R 4 are hydrogen.]

15. A composition for improving an unpleasant flavor, comprising at least one cyclic ketone compound selected from the compounds in Group A below as an active ingredient, The unpleasant flavor improving composition, wherein the unpleasant flavor is a light deterioration odor of milk or a light deterioration odor of fruit juice. (Group A) Cyclic ketone compounds represented by the following formula A 【Chemistry 7】 [wherein n is 0, the dashed line represents a single bond or a double bond, and when the dashed line on the ring is a double bond, R 1 is a hydroxy group, R 2 is an ethyl group, and when the dashed line on the ring is a single bond, R 1 is an oxygen bonded to a carbon on the ring by a double bond, R 2 is an ethyl group, and R 3 and R 4 are hydrogen.]

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