Bitterness suppressor for food or drink, method for producing edible oil or fat-containing composition, method for producing food or drink with suppressed bitterness, method for suppressing bitterness of food or drink, and food or drink

Abstract

To provide a bitterness inhibitor containing a compound other than a compound contained in a conventional bitterness inhibitor as an active ingredient, as a bitterness inhibiting active ingredient.SOLUTION: The bitterness suppressant is selected from the group of ketones consisting of 3-pentanone, 2-heptanone, and 2-octanone, the group of saturated aliphatic alcohols consisting of 1-pentanol, 1-hexanol, and 1-octanol, trans-2-penten-1-ol, trans-2-hexen-1-ol, trans-3-hexen-1-ol, trans-2-hepten-1-ol, cis-2-penten-1-ol, cis-2-hexen-1-ol, cis-3-hexen-1-ol, and cis-2-hepten-1-ol, as an active ingredient.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a bitterness suppressor for foods and beverages, a method for producing an edible fat-and-oil-containing composition, a method for producing foods and beverages with reduced bitterness, a method for suppressing the bitterness of foods and beverages, and foods and beverages containing the bitterness suppressor. [Background technology]

[0002] Bitter components contained in foods and beverages, such as polyphenols and caffeine, are not only important factors in the flavor of the foods and beverages that characterize their taste, but are also attracting attention for their various health and beauty functionalities. However, if the content of bitter components in foods and beverages is high, the bitterness may become too strong, impairing the flavor of the foods and beverages. Therefore, it is necessary to suppress the bitterness of foods and beverages that contain a large amount of bitter components, and various bitterness suppressors have been investigated.

[0003] For example, Patent Document 1 discloses a bitterness suppressing agent containing a glycerin succinic acid fatty acid ester and a glycerin mono-fatty acid ester, and Patent Document 2 discloses a bitterness suppressing agent for alcoholic beverages containing a specific cyclotetrasaccharide and an organic acid. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Application Publication No. 2019-058116 [Patent Document 2] Japanese Patent Application Publication No. 2022-157889 Summary of the Invention [Problem to be solved by the invention]

[0005] The problem to be solved by the present invention is to provide a bitterness suppressor containing, as a bitterness suppressing active ingredient, a compound other than compounds contained as active ingredients in conventional bitterness suppressors, and a method for producing an edible oil-and-fat-containing composition containing the bitterness suppressing active ingredient. Another problem to be solved by the present invention is to provide a method for producing a food or beverage with suppressed bitterness that contains the bitterness suppressor or the edible oil-and-fat-containing composition, a method for suppressing the bitterness of a food or beverage by incorporating the bitterness suppressor or the edible oil-and-fat-containing composition into the food or beverage, and a food or beverage that contains the bitterness suppressor or the edible oil-and-fat-containing composition. [Means for solving the problem]

[0006] It has been discovered that by mixing unrefined olive oil with a high polyphenol content and a strong bitter taste with unrefined olive oil containing a predetermined amount or more of specific compounds, it is possible to produce unrefined olive oil with a high polyphenol content but reduced bitterness. The inventors have found that these compounds can reduce the bitterness of various foods and beverages. The present invention has been completed based on these findings.

[0007] The present invention provides a bitterness suppressor for foods and beverages, The composition contains at least one active ingredient selected from the group consisting of a ketone represented by the following formula (1), a saturated aliphatic alcohol represented by the following formula (2), an unsaturated aliphatic alcohol represented by the following formula (3), and an unsaturated aliphatic alcohol represented by the following formula (4),

[0008] [ka]

[0009] [ka]

[0010] [ka]

[0011] [ka]

[0012] In the formulas (1) to (4), R 1 is an alkyl group having 1 to 6 carbon atoms, and R 2 is a methyl group or an ethyl group, and R 3 is an alkyl group having 1 to 5 carbon atoms, and R 4 is an alkyl group having 1 to 5 carbon atoms, and R 5 is a methylene group or an ethylene group.

[0013] The ketone represented by formula (1) preferably includes at least one selected from the group consisting of 3-pentanone, 2-heptanone, and 2-octanone, the saturated aliphatic alcohol represented by formula (2) preferably includes at least one selected from the group consisting of 1-pentanol, 1-hexanol, and 1-octanol, and the unsaturated aliphatic alcohol represented by formula (3) or (4) preferably includes at least one selected from the group consisting of trans-2-penten-1-ol, trans-2-hexen-1-ol, trans-3-hexen-1-ol, trans-2-hepten-1-ol, cis-2-penten-1-ol, cis-2-hexen-1-ol, cis-3-hexen-1-ol, and cis-2-hepten-1-ol.

[0014] The bitterness suppressor is preferably an oil composition containing an edible oil containing at least one selected from the group consisting of a ketone represented by formula (1), a saturated fatty alcohol represented by formula (2), an unsaturated fatty alcohol represented by formula (3), and an unsaturated fatty alcohol represented by formula (4).

[0015] The present invention provides a method for producing an edible fat or oil, comprising the step of blending at least one selected from the group consisting of a ketone represented by the following formula (1), a saturated aliphatic alcohol represented by the following formula (2), an unsaturated aliphatic alcohol represented by the following formula (3), and an unsaturated aliphatic alcohol represented by the following formula (4), into an edible fat or oil,

[0016] [ka]

[0017] [ka]

[0018] [ka]

[0019] [ka]

[0020] In the formulas (1) to (4), R 1 is an alkyl group having 1 to 6 carbon atoms, and R 2 is a methyl group or an ethyl group, and R 3 is an alkyl group having 1 to 5 carbon atoms, and R 4 is an alkyl group having 1 to 5 carbon atoms, and R 5 is a methylene group or an ethylene group.

[0021] The edible fat-and-oil-containing composition is preferably used to suppress the bitterness of foods and beverages.

[0022] The total content of the ketone represented by formula (1), the saturated aliphatic alcohol represented by formula (2), the unsaturated aliphatic alcohol represented by formula (3), and the unsaturated aliphatic alcohol represented by formula (4) in the edible oil-and-fat-containing composition is preferably 0.01 mass ppm or more.

[0023] The present invention relates to a method for producing a food or drink with reduced bitterness, which includes a step of blending the bitterness suppressor or the edible fat / oil-containing composition.

[0024] The present invention relates to a method for suppressing the bitterness of food or drink, which comprises a step of blending the bitterness suppressor or the edible fat / oil-containing composition.

[0025] The total content of the ketone represented by the formula (1), the saturated aliphatic alcohol represented by the formula (2), the unsaturated aliphatic alcohol represented by the formula (3), and the unsaturated aliphatic alcohol represented by the formula (4) in the food or drink is preferably 0.001 mass ppm or more.

[0026] The present invention further relates to a food or drink containing the bitterness suppressor or the edible fat-and-oil-containing composition. [Effects of the Invention]

[0027] The bitterness suppressor for foods and beverages of the present invention contains as a bitterness-suppressing active ingredient a compound other than compounds contained as active ingredients in conventional bitterness suppressors, and suppresses the bitterness of various foods and beverages. The method for producing an edible oil-and-fat-containing composition of the present invention provides a method for producing an edible oil-and-fat-containing composition that suppresses the bitterness of various foods and beverages. The method for producing foods and beverages with suppressed bitterness and the method for suppressing the bitterness of foods and beverages of the present invention provide various foods and beverages with suppressed bitterness. The bitterness of the foods and beverages of the present invention is suppressed. DETAILED DESCRIPTION OF THE INVENTION

[0028] The present invention will now be described in further detail.

[0029] In this specification, substituents, linking groups, etc. (hereinafter referred to as "substituents, etc.") that are not specified as substituted or unsubstituted mean that the group may have an appropriate substituent. Therefore, even when the specification simply states "group" (e.g., "alkyl group"), this "group" (e.g., "alkyl group") encompasses not only an embodiment that does not have a substituent (e.g., "unsubstituted alkyl group"), but also an embodiment that further has a substituent (e.g., "substituted alkyl group"). This also applies to compounds that are not specified as substituted or unsubstituted. Preferred substituents include the substituent T described below.

[0030] In the present specification, when the term "substituent" is simply used, a substituent selected from the substituent T described below is preferably applied.

[0031] In this specification, when there are multiple substituents, etc., designated by a specific symbol, or when multiple substituents, etc., are simultaneously or alternatively defined, this means that the respective substituents, etc., may be the same or different from each other. Furthermore, even if not otherwise specified, when multiple substituents, etc., are adjacent, they may be linked to each other or condensed to form a ring.

[0032] Furthermore, when an upper limit and a lower limit of a numerical range are indicated in this specification, the upper limit and the lower limit can be combined as appropriate, and the resulting numerical range is also considered to be disclosed. <Bitterness suppressant for food and beverages> The bitterness suppressor for foods and beverages of the present invention contains at least one active ingredient selected from the group consisting of a ketone represented by the following formula (1), a saturated aliphatic alcohol represented by the following formula (2), an unsaturated aliphatic alcohol represented by the following formula (3), and an unsaturated aliphatic alcohol represented by the following formula (4).

[0033] [ka]

[0034] [ka]

[0035] [ka]

[0036] [ka]

[0037] In the formulas (1) to (4), R 1 is an alkyl group having 1 to 6 carbon atoms, and R 2 is a methyl group or an ethyl group, and R 3 is an alkyl group having 1 to 5 carbon atoms, and R 4 is an alkyl group having 1 to 5 carbon atoms, and R 5 is a methylene group or an ethylene group.

[0038] Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a pentyl group, a 1-methylbutyl group, a 2-methylbutyl group, a 3-methylbutyl group, a 1-ethylpropyl group, a 1,1-dimethylpropyl group, a 1,2-dimethylpropyl group, a 2,2-dimethylpropyl group, a hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 3-methylpentyl group, a 4-methylpentyl group, a 1,1-dimethylbutyl group, a 1,2-dimethylbutyl group, a 2,2-dimethylbutyl group, a 1,3-dimethylbutyl group, and a 2,3-dimethylbutyl group.

[0039] As described above, the R 1 ~R 5 The substituent T is not particularly limited, but is preferably a cycloalkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group (aromatic heterocyclic group), or an aliphatic heterocyclic group.

[0040] The cycloalkyl group preferably has a carbon number of 3 to 10, more preferably 3 to 8. Examples of the cycloalkyl group include cyclopropyl, cyclopentyl, and cyclohexyl.

[0041] The alkenyl group preferably has 2 to 36 carbon atoms, more preferably 2 to 18 carbon atoms, and even more preferably 2 to 6 carbon atoms. Examples of the alkenyl group include vinyl, allyl, butenyl, and hexenyl.

[0042] The alkynyl group preferably has 2 to 36 carbon atoms, more preferably 2 to 18 carbon atoms, and even more preferably 2 to 4 carbon atoms. Examples of the alkynyl group include ethynyl, butynyl, and hexynyl.

[0043] The aryl group is preferably an aryl group having 6 to 24 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms. An example of the aryl group is a phenyl group.

[0044] When the aromatic heterocycle is a fused ring, it includes not only groups consisting of a monocyclic aromatic heterocycle but also groups consisting of a fused heterocycle in which another ring, such as an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a heterocycle, is fused to the monocyclic aromatic heterocycle. The number of ring-constituting heteroatoms constituting the aromatic heterocycle may be one or more, and the heteroatom is preferably a nitrogen atom, an oxygen atom, or a sulfur atom. The number of ring members in the aromatic heterocycle is preferably a 3- to 8-membered ring, more preferably a 5- or 6-membered ring. The number of carbon atoms in the aromatic heterocycle is preferably 5 to 24, more preferably 5 to 18, and even more preferably 5 to 10. The number of carbon atoms in the aromatic heterocycle is preferably 5 to 24, more preferably 5 to 18, and even more preferably 5 to 10. Examples of 5-membered aromatic heterocycles and fused heterocycles containing 5-membered aromatic heterocycles include pyrrole ring, imidazole ring, pyrazole ring, oxazole ring, thiazole ring, triazole ring, furan ring, thiophene ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, indoline ring, and indazole ring. Examples of 6-membered aromatic heterocycles and fused heterocycles containing 6-membered aromatic heterocycles include pyridine ring, pyrimidine ring, pyrazine ring, triazine ring, quinoline ring, and quinazoline ring.

[0045] Aliphatic heterocyclic groups include monocyclic groups consisting of only an aliphatic heterocycle and groups consisting of an aliphatic fused heterocycle in which another ring (for example, an aliphatic ring) is fused to an aliphatic heterocycle. The number of ring-constituting heteroatoms constituting the aliphatic heterocycle may be one or more, and the heteroatom is preferably a nitrogen atom, an oxygen atom, or a sulfur atom. The number of ring members in the aliphatic heterocycle is preferably a 3- to 8-membered ring, more preferably a 5- or 6-membered ring. The number of carbon atoms in the aliphatic heterocycle is preferably 0 to 24, more preferably 1 to 18, even more preferably 2 to 10, and particularly preferably 3 to 5. Specific preferred examples of the aliphatic heterocycle include a pyrrolidine ring, an oxolane ring, a thiolane ring, a piperidine ring, a tetrahydrofuran ring, an oxane ring (tetrahydropyran ring), a thiane ring, a piperazine ring, a morpholine ring, a quinuclidine ring, a pyrrolidine ring, an azetidine ring, an oxetane ring, an aziridine ring, a dioxane ring, a pentamethylene sulfide ring, and γ-butyrolactone.

[0046] The substituent T also includes the following groups.

[0047] an alkoxy group (preferably an alkoxy group having from 1 to 20 carbon atoms, for example, methoxy, ethoxy, isopropyloxy, benzyloxy, etc.); an aryloxy group (preferably an aryloxy group having from 6 to 26 carbon atoms, for example, phenoxy, 1-naphthyloxy, 3-methylphenoxy, 4-methoxyphenoxy, etc.); heterocyclic oxy group (a group in which an —O— group is bonded to the above heterocyclic group), an alkoxycarbonyl group (preferably an alkoxycarbonyl group having from 2 to 20 carbon atoms, for example, ethoxycarbonyl, 2-ethylhexyloxycarbonyl, etc.); an aryloxycarbonyl group (preferably an aryloxycarbonyl group having from 6 to 26 carbon atoms, for example, phenoxycarbonyl, 1-naphthyloxycarbonyl, 3-methylphenoxycarbonyl, 4-methoxyphenoxycarbonyl, etc.); an amino group (preferably including an amino group having from 0 to 20 carbon atoms, an alkylamino group, or an arylamino group, for example, amino (—NH), N,N-dimethylamino, N,N-diethylamino, N-ethylamino, anilino, etc.); a sulfamoyl group (preferably a sulfamoyl group having 0 to 20 carbon atoms, for example, N,N-dimethylsulfamoyl, N-phenylsulfamoyl, etc.); acyl groups (including alkylcarbonyl groups, alkenylcarbonyl groups, alkynylcarbonyl groups, arylcarbonyl groups, and heterocyclic carbonyl groups, preferably acyl groups having 1 to 20 carbon atoms, for example, acetyl, propionyl, butyryl, octanoyl, hexadecanoyl, acryloyl, methacryloyl, crotonoyl, benzoyl, naphthoyl, nicotinoyl, etc.); acyloxy groups (including alkylcarbonyloxy groups, alkenylcarbonyloxy groups, alkynylcarbonyloxy groups, arylcarbonyloxy groups, and heterocyclic carbonyloxy groups, preferably acyloxy groups having 1 to 20 carbon atoms, for example, acetyloxy, propionyloxy, butyryloxy, octanoyloxy, hexadecanoyloxy, acryloyloxy, methacryloyloxy, crotonoyloxy, benzoyloxy, naphthoyloxy, and nicotinoyloxy), an aryloyloxy group (preferably an aryloyloxy group having from 7 to 23 carbon atoms, for example, benzoyloxy, etc.); a carbamoyl group (preferably a carbamoyl group having 1 to 20 carbon atoms, for example, N,N-dimethylcarbamoyl, N-phenylcarbamoyl, etc.); acylamino groups (preferably acylamino groups having 1 to 20 carbon atoms, for example, acetylamino, benzoylamino, etc.); an alkylthio group (preferably an alkylthio group having 1 to 20 carbon atoms, for example, methylthio, ethylthio, isopropylthio, benzylthio, etc.); an arylthio group (preferably an arylthio group having from 6 to 26 carbon atoms, for example, phenylthio, 1-naphthylthio, 3-methylphenylthio, 4-methoxyphenylthio, etc.); heterocyclic thio group (a group in which the above heterocyclic group is bonded to an -S- group), an alkylsulfonyl group (preferably an alkylsulfonyl group having 1 to 20 carbon atoms, for example, methylsulfonyl, ethylsulfonyl, etc.); an arylsulfonyl group (preferably an arylsulfonyl group having 6 to 22 carbon atoms, for example, benzenesulfonyl, etc.); an alkylsilyl group (preferably an alkylsilyl group having 1 to 20 carbon atoms, for example, monomethylsilyl, dimethylsilyl, trimethylsilyl, triethylsilyl, etc.); an arylsilyl group (preferably an arylsilyl group having 6 to 42 carbon atoms, for example, triphenylsilyl, etc.); a phosphoryl group (preferably a phosphate group having 0 to 20 carbon atoms, for example, —OP(═O)(RP)2); a phosphonyl group (preferably a phosphonyl group having 0 to 20 carbon atoms, for example, —P(═O)(RP)), A phosphinyl group (preferably a phosphinyl group having from 0 to 20 carbon atoms, for example, -P(RP)2), a sulfo group (sulfonic acid group), a carboxy group, a hydroxy group, a sulfanyl group, a cyano group, or a halogen atom (for example, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc.). RP is a hydrogen atom or a substituent (preferably a group selected from the above-mentioned substituents).

[0048] The ketone represented by the formula (1) preferably includes at least one selected from the group consisting of 3-pentanone, 2-heptanone, and 2-octanone, more preferably includes at least one selected from the group consisting of 3-pentanone and 2-octanone, and even more preferably is 3-pentanone or 2-octanone.

[0049] The saturated aliphatic alcohol represented by the formula (2) preferably includes at least one selected from the group consisting of 1-pentanol, 1-hexanol, and 1-octanol, more preferably includes at least one selected from the group consisting of 1-pentanol and 1-hexanol, and even more preferably includes 1-pentanol or 1-hexanol.

[0050] The unsaturated aliphatic alcohol represented by the formula (3) preferably includes at least one selected from the group consisting of trans-2-penten-1-ol, trans-2-hexen-1-ol, trans-3-hexen-1-ol, and trans-2-hepten-1-ol, more preferably includes at least one selected from the group consisting of trans-2-penten-1-ol, trans-2-hexen-1-ol, and trans-3-hexen-1-ol, and even more preferably includes trans-2-penten-1-ol, trans-2-hexen-1-ol, or trans-3-hexen-1-ol.

[0051] The unsaturated aliphatic alcohol represented by the formula (4) preferably includes at least one selected from the group consisting of cis-2-penten-1-ol, cis-2-hexen-1-ol, cis-3-hexen-1-ol, and cis-2-hepten-1-ol, more preferably includes at least one selected from the group consisting of cis-2-penten-1-ol, cis-2-hexen-1-ol, and cis-3-hexen-1-ol, and even more preferably includes cis-2-penten-1-ol, cis-2-hexen-1-ol, or cis-3-hexen-1-ol.

[0052] The bitterness suppressor of the present invention may be an oil or fat composition containing an edible oil or fat containing at least one selected from the group consisting of a ketone represented by formula (1), a saturated fatty alcohol represented by formula (2), an unsaturated fatty alcohol represented by formula (3), and an unsaturated fatty alcohol represented by formula (4).

[0053] The edible oils and fats may be any edible oils and fats containing at least one selected from the group consisting of ketones represented by formula (1), saturated aliphatic alcohols represented by formula (2), unsaturated aliphatic alcohols represented by formula (3), and unsaturated aliphatic alcohols represented by formula (4), including vegetable oils and fats such as rapeseed oil, soybean oil, sunflower oil, cottonseed oil, peanut oil, rice oil, corn oil, safflower oil, olive oil, kapok oil, sesame oil, perilla oil, linseed oil, evening primrose oil, palm oil, shea butter, monkey fat, cocoa butter, coconut oil, and palm kernel oil; animal oils and fats such as lard, beef tallow, chicken oil, milk fat, and fish oil; and synthetic oils and fats such as medium-chain fatty acid triglycerides. Furthermore, processed vegetable oils and fats, animal oils, and synthetic oils and fats may also be used, each of which has been subjected to at least one of deep hydrogenation, fractionation, and interesterification. These oils and fats may be used alone or in combination of two or more. Among them, the edible oil and fat preferably includes olive oil, and more preferably includes unrefined olive oil.

[0054] The bitterness suppressor of the present invention may be the edible oil or fat itself. Examples of the bitterness suppressor of the present invention include olive oil such as unrefined olive oil.

[0055] The term "unrefined olive oil" as used herein refers to oil separated from olives by methods such as pressing or centrifugation, and which has not undergone one or more of the following refining processes: degumming, deacidification, bleaching, and deodorization. Preferably, the olive oil has not undergone any of the following refining processes: degumming, deacidification, bleaching, and deodorization. The degumming process involves hydrating and removing the gums, primarily composed of phospholipids, contained in the oil. The deacidification process involves removing free fatty acids contained in the oil as soap by treatment with alkaline water, etc. The bleaching process involves removing pigments contained in the oil by adsorption onto activated clay, etc. The deodorization process involves removing odorous components contained in the oil by steam distillation under reduced pressure, etc. The origin of the olives is not particularly limited, and they may be domestically or internationally sourced.

[0056] Unrefined olive oil is distributed on the market as extra virgin olive oil (also called extra virgin olive oil), virgin olive oil, ordinary virgin olive oil, lampante virgin olive oil, etc., and any of these may be used. In the present invention, such commercially available products may be used, preferably one or two selected from extra virgin olive oil and virgin olive oil, more preferably extra virgin olive oil. Virgin olive oil is classified into four types based on the criteria for sensory evaluation: extra virgin olive oil, virgin olive oil, ordinary virgin olive oil, and lampante virgin olive oil. The criteria for virgin olive oil can be determined by reference to those established by the International Olive Council. Unrefined olive oil may be excluded from the bitterness suppressor of the present invention.

[0057] The bitterness suppressant of the present invention may be at least one compound selected from the group consisting of a ketone represented by formula (1), a saturated aliphatic alcohol represented by formula (2), an unsaturated aliphatic alcohol represented by formula (3), and an unsaturated aliphatic alcohol represented by formula (4). <Edible oil-containing composition> The method for producing an edible oil-containing composition of the present invention includes a step of blending at least one selected from the group consisting of a ketone represented by formula (1), a saturated aliphatic alcohol represented by formula (2), an unsaturated aliphatic alcohol represented by formula (3), and an unsaturated aliphatic alcohol represented by formula (4) with edible oil.

[0058] The edible oils and fats used in the method for producing an edible oil-containing composition of the present invention may be any edible oil or fat commonly used in the food industry. Examples of edible oils and fats include vegetable oils such as rapeseed oil, soybean oil, sunflower oil, cottonseed oil, peanut oil, rice oil, corn oil, safflower oil, olive oil, kapok oil, sesame oil, perilla oil, linseed oil, evening primrose oil, palm oil, shea butter, monkey fat, cocoa butter, coconut oil, and palm kernel oil; animal oils and fats such as lard, beef tallow, chicken oil, milk fat, and fish oil; and synthetic oils and fats such as medium-chain fatty acid triglycerides. Furthermore, processed vegetable oils and fats, animal oils, and synthetic oils may also be used, which have been subjected to at least one of deep hydrogenation, fractionation, and interesterification. These oils and fats may be used alone or in combination. In particular, the edible oils and fats preferably include at least one selected from the group consisting of rapeseed oil, soybean oil, olive oil, rice bran oil, corn oil, sunflower oil, cottonseed oil, safflower oil, palm oil, palm kernel oil, coconut oil, and processed oils and fats thereof, more preferably include at least one selected from the group consisting of rapeseed oil, soybean oil, olive oil, rice bran oil, and corn oil, and even more preferably include at least one selected from the group consisting of rapeseed oil, soybean oil, and corn oil.

[0059] The edible fat-and-oil-containing composition may be used to suppress the bitterness of food and drink.

[0060] The concentration of at least one compound selected from the group consisting of the ketone represented by formula (1), the saturated aliphatic alcohol represented by formula (2), the unsaturated aliphatic alcohol represented by formula (3), and the unsaturated aliphatic alcohol represented by formula (4) in the oil and fat composition and the edible oil-containing composition is preferably 0.01 ppm by mass or more, more preferably 0.03 ppm by mass or more, even more preferably 0.05 ppm by mass or more, still more preferably 0.08 ppm by mass or more, and even more preferably 0.1 ppm by mass or more. When the lower limit of the concentration is 0.01 ppm by mass or more, the bitterness of a food or drink containing the bitterness suppressor of the present invention or the edible oil-containing composition is more effectively suppressed.

[0061] The concentration of at least one compound selected from the group consisting of the ketone represented by formula (1), the saturated aliphatic alcohol represented by formula (2), the unsaturated aliphatic alcohol represented by formula (3), and the unsaturated aliphatic alcohol represented by formula (4) in the oil and fat composition and the edible oil and fat-containing composition is preferably 20,000 mass ppm or less, more preferably 15,000 mass ppm or less, even more preferably 10,000 mass ppm or less, still more preferably 8,000 mass ppm or less, and even more preferably 6,000 mass ppm or less.

[0062] The bitterness suppressant and edible oil-containing composition of the present invention may be in any form or shape, such as a powder, a solid, a gel formed by gelling with a gelling agent or the like, or a liquid dissolved in oil or a solvent or the like.

[0063] The bitterness suppressant and edible oil-containing composition of the present invention may contain at least one of dairy products, thickening stabilizers, salt seasonings such as salt and potassium chloride, acidulants such as acetic acid, lactic acid and gluconic acid, sugars, sweeteners, coloring agents, antioxidants, vegetable proteins, eggs and various egg products, flavorings, seasonings, pH adjusters, food preservatives, fruits, fruit juices, and spices. <Application of bitterness suppressant and edible oil-containing composition> The bitterness suppressant or edible oil-containing composition of the present invention is incorporated into a food or beverage to suppress the bitterness of the food or beverage, thereby preparing a food or beverage with suppressed bitterness. Incorporation of the bitterness suppressant or edible oil-containing composition of the present invention into the food or beverage may involve adding, mixing, applying, dissolving, dispersing, emulsifying, injecting, or the like to the food or beverage, or by using the bitterness suppressant or edible oil-containing composition of the present invention as a cooking oil (e.g., stir-frying oil, deep-frying oil, etc.) for the food or beverage. Alternatively, a seasoning such as dressing or mayonnaise containing the bitterness suppressant or edible oil-containing composition of the present invention may be prepared, and the seasoning may be added, mixed, applied, dissolved, dispersed, emulsified, injected, or the like to the food or beverage.

[0064] The concentration of at least one compound selected from the group consisting of the ketone represented by formula (1), the saturated aliphatic alcohol represented by formula (2), the unsaturated aliphatic alcohol represented by formula (3), and the unsaturated aliphatic alcohol represented by formula (4) in the food or drink of the present invention is preferably 0.001 mass ppm or more, more preferably 0.005 mass ppm or more, even more preferably 0.008 mass ppm or more, still more preferably 0.01 mass ppm or more, even more preferably 0.05 mass ppm or more, still more preferably 0.1 mass ppm or more, particularly preferably 1 mass ppm or more, and most preferably 5 mass ppm or more. When the lower limit of the concentration is 0.001 mass ppm or more, the bitterness of the food or drink of the present invention is more effectively suppressed.

[0065] The concentration of at least one compound selected from the group consisting of the ketone represented by formula (1), the saturated aliphatic alcohol represented by formula (2), the unsaturated aliphatic alcohol represented by formula (3), and the unsaturated aliphatic alcohol represented by formula (4) in the food and beverage of the present invention is preferably 2000 mass ppm or less, more preferably 1500 mass ppm or less, even more preferably 1000 mass ppm or less, still more preferably 800 mass ppm or less, even more preferably 600 mass ppm or less, and particularly preferably 500 mass ppm or less.

[0066] The food and drink of the present invention is not particularly limited. Examples of the foods and beverages of the present invention include foods and beverages containing alkaloids (e.g., caffeine, theobromine, nicotine, quinine, etc.); foods and beverages containing flavanone glycosides (e.g., naringin, etc.); foods and beverages containing polyphenols (e.g., flavonoids (catechin, anthocyanin, tannin, isoflavone, quercitrin, etc.), phenolic acids (chlorogenic acid, etc.), lignans, coumarin, cocoa polyphenols, etc.); foods and beverages containing terpenoids (e.g., limonene, currubitacin, etc.); foods and beverages containing bitter glycosides (saponins, etc.); foods and beverages containing humulones (humulone, isohumulone, etc.); foods and beverages containing bitter amino acids (e.g., phenylalanine, histidine, arginine, isoleucine, valine, leucine, methionine, tryptophan, etc.); foods and beverages containing bitter peptides; foods and beverages containing bitter proteins; and foods and beverages containing inorganic salts (e.g., magnesium salts, calcium salts, etc.).

[0067] The food and drink is preferably at least one selected from the group consisting of food and drink containing alkaloids, food and drink containing polyphenols, and food and drink containing terpenoids, and more preferably at least one selected from the group consisting of food and drink containing alkaloids and food and drink containing polyphenols.

[0068] The foods and drinks of the present invention also include beverages such as green tea, roasted green tea, sencha, matcha, brown rice tea, bancha, coffee, black tea, herbal tea, and beer; bitter vegetables such as bell peppers, bitter melon, spinach, broad beans, zucchini, shishito peppers, cucumbers, butterbur sprouts, and taros; fruits such as grapefruit, lemons, melons, and persimmons; oil-processed foods (foods containing edible oils as an ingredient) such as margarine, spreads, butter, mayonnaise, dressings, and cream; bakery foods such as donuts, cookies, pies, cakes, bread, and pizza; noodles such as soba, udon, ramen, and pasta; cooked rice dishes such as cooked rice and fried rice; Examples include dairy products such as cheese, butter, and yogurt; processed meat foods such as hamburgers, ham, and sausages; processed seafood foods such as chikuwa and kamaboko; soups such as corn soup, consommé soup, and potage; condiments and sauces such as dressings, mayonnaise, Chinese food bases, and grilled meat sauces; fried foods such as donuts, fried bread, fried chicken, tempura, croquettes, and French fries; stir-fried foods such as stir-fried vegetables, stir-fried liver, stir-fried chives, stir-fried bean sprouts, and fried rice; baked foods such as hamburgers, steaks, dumplings, and fried eggs; frozen foods; health foods; processed soy foods such as tofu and natto; and plant-based foods such as soy-derived substitutes.

[0069] The food and drink of the present invention may contain the olive oil such as the unrefined olive oil. The food and drink containing the unrefined olive oil may be excluded from the food and drink of the present invention. (Impossible / impractical circumstances) The bitterness of a food or beverage containing the bitterness suppressant or edible oil-containing composition of the present invention is suppressed, and the bitterness can be evaluated by eating the food or beverage, but quantitative measurement of the bitterness is impossible or impractical. In other words, it is impossible or impractical to directly identify a food or beverage containing the bitterness suppressant or edible oil-containing composition of the present invention by its structure or properties. Therefore, a food or beverage containing the bitterness suppressant or edible oil-containing composition of the present invention should be identified by the method for producing the food or beverage of the present invention. [Example]

[0070] The present invention will be described in more detail below based on examples, but the present invention is not limited to these examples.

[0071] In Tests 1 to 6, various physical properties were evaluated or measured as follows. <Bitterness evaluation> Two to four panelists ate and drank each sample, evaluated the bitterness of each sample according to the following criteria, and calculated the average score. -Bitterness evaluation criteria- Sample is much more bitter than the control: 7 points Sample is more bitter than the control: 6 points Sample is slightly more bitter than the control: 5 points Control (sample without the active ingredient) or bitterness equivalent to the control: 4 points Sample is slightly less bitter than the control: 3 points Sample is less bitter than the control: 2 points No bitterness of the sample: 1 point <Measurement of Ketone, Saturated Fatty Alcohol, and Unsaturated Fatty Alcohol Content in Test 6> 1.5 g of each crude olive oil sample was weighed into a 10 mL glass vial, and 5 μL of a 1.611 mg / mL methanol solution of 4-methyl-2-pentanol was added as an internal standard (see Eur. J. Lipid. Sci. Technol., 2015, vol. 117, pp. 514-522). The contents of ketones, saturated fatty alcohols, and unsaturated fatty alcohols in each crude olive oil sample were measured by solid phase microextraction (SPME) using a LECO Japan GC-Tof-MS Pegasus® BT instrument and an Agilent Technologies DB-WAX-UI column (internal diameter: 0.25 mm, length: 30 m, film thickness: 0.25 μm) under the following conditions. Heating: 40℃, 2 minutes, Adsorbent: StableFlex 50 / 30 μm, Supelco DVB / CAR / PDMS Collection time: 40°C, 40 minutes, Carrier gas: Helium, Flow rate: 1.07ml / min, Oven temperature: 40°C for 10 minutes, then increase the temperature at a rate of 3°C / min, and keep at 200°C for 10 minutes. Scan range: m / z=45-400, Split ratio: 1:10, Ion source temperature: 250°C, Ionization: EI, Ionization voltage: 70V.

[0072] The compounds used in Tests 1 to 5 are as follows: (1) 2-Octanone (Sigma-Aldrich Japan LLC) (2) cis-3-hexen-1-ol (Sigma-Aldrich Japan, LLC) (3) trans-2-hexen-1-ol (Sigma-Aldrich Japan, LLC) (4) 1-Hexanol (Sigma-Aldrich Japan, LLC) <Test 1> Any of the compounds (1) to (4) was added to green tea (Oi Ocha Koicha (containing catechin and caffeine as bitter components) manufactured by Ito En Co., Ltd.) to the concentrations shown in Table 1, and the bitterness of each sample was evaluated. The bitterness of the green tea containing 1000 ppm by mass of 2-octanone in Test 1-1, the green tea containing 50 ppm by mass of trans-2-hexen-1-ol in Test 1-3, and the green tea containing 50 ppm by mass of 1-hexanol in Test 1-4 was evaluated by a panel of three people, the bitterness of the green tea containing 100 ppm by mass of 1-hexanol in Test 1-4 was evaluated by a panel of two people, and the bitterness of the other green teas was evaluated by a panel of four people. The results are shown in Table 1.

[0073] [Table 1]

[0074] The bitterness of green tea was suppressed by each of the compounds (1) to (4). <Test 2> Any of the compounds (1) to (4) was added to coffee (dark drip coffee manufactured by Ryohin Keikaku Co., Ltd. (containing caffeine and chlorogenic acid as bitter components)) to the concentrations shown in Table 2, and the bitterness of each sample was evaluated. The bitterness of coffee containing 50 ppm, 100 ppm, and 200 ppm by mass of 2-octanone in Test 2-1, coffee containing 100 ppm and 200 ppm by mass of cis-3-hexen-1-ol in Test 2-2, coffee containing 50 ppm by mass of trans-2-hexen-1-ol in Test 2-3, and coffee containing 100 ppm by mass of 1-hexanol in Test 2-4 was evaluated by a panel of three people, and the bitterness of the other coffees was evaluated by a panel of four people. The results are shown in Table 2.

[0075] [Table 2]

[0076] The bitterness of coffee was suppressed by each of the compounds (1) to (4). <Test 3> Each sample was prepared by adding any of the compounds (1) to (4) to rapeseed oil (free canola oil, manufactured by J-Oil Mills, Inc.) to the concentration shown in Table 3. Next, 7 g of each sample was heated for 30 seconds in a frying pan that had been preheated at 180°C for 30 seconds, and then 75 g of bell peppers (containing quercitrin as a bitter component) cut into 0.5 cm strips were added to the frying pan and fried for 2 minutes. The bitterness of each bell pepper fried with each sample was evaluated by a panel of four people. The results are shown in Table 3.

[0077] [Table 3]

[0078] The bitterness of bell peppers fried in rapeseed oil to which any of the compounds (1) to (4) had been added was suppressed by each of the compounds (1) to (4). <Test 4> Each sample (dressing) was prepared by mixing one of the compounds (1) to (4) with 18 g of rapeseed oil (smooth canola oil, manufactured by J-Oil Mills, Inc.), 1 g of vinegar (grain vinegar, manufactured by Mizkan Co., Ltd.), and 0.2 g of salt (manufactured by the Salt Industry Center, Public Interest Foundation) to the concentration shown in Table 4. Next, 50 g of green peppers (containing quercitrin as a bitter component) cut into 2-3 mm strips was mixed with 15 g of each sample (dressing). The bitterness of the green peppers mixed with each sample was evaluated by a four-person panel. The results are shown in Table 4.

[0079] [Table 4]

[0080] The bitterness of bell peppers mixed with a dressing containing any of the compounds (1) to (4) was suppressed by each of the compounds (1) to (4). <Test 5> Two or three of the compounds (1) to (4) were added to rapeseed oil (free canola oil, manufactured by J-Oil Mills, Inc.) to the concentrations shown in Table 5 to prepare each sample. Next, 7 g of each sample was heated for 30 seconds in a frying pan that had been preheated at 180°C for 30 seconds, and then 75 g of bell peppers (containing quercitrin as a bitter component) cut into 0.5 cm strips were added to the frying pan and fried for 2 minutes. The bitterness of each bell pepper fried with each sample was evaluated by a panel of four people. The results are shown in Table 5.

[0081] [Table 5]

[0082] The bitterness of bell peppers fried in rapeseed oil to which a combination of two or three of the compounds (1) to (4) had been added was suppressed by the combination of two or three of the compounds (1) to (4). <Test 6> Rapeseed oil (manufactured by J-Oil Mills Co., Ltd.), extra virgin olive oil A (manufactured by J-Oil Mills Co., Ltd.), and extra virgin olive oil B (manufactured by J-Oil Mills Co., Ltd.) were used as samples. 7 g of each sample was heated for 30 seconds in a frying pan preheated at 180°C. 75 g of bell peppers (containing quercitrin as a bitter component) cut into 0.5 cm strips were then added to the frying pan and fried for 2 minutes. The bitterness of the bell peppers fried with each sample was evaluated by a panel of four people. The concentrations of compounds (1) to (4) contained in extra virgin olive oil A and extra virgin olive oil B are shown in Table 6. The bitterness evaluation results are shown in Table 7. The concentrations shown in Table 6 are in ppm by mass.

[0083] [Table 6]

[0084] [Table 7]

[0085] The bitterness of the bell peppers fried in either extra virgin olive oil A or extra virgin olive oil B containing the compounds (1) to (4) was suppressed.

[0086] In Test 7, various physical properties were evaluated or measured as follows. <Bitterness evaluation> Six panelists tasted the cooked bitter melons and rated their bitterness intensity using a visual analogue scale (VAS) from 0 to 10, with 0 being "not bitter at all" and 10 being "extremely bitter," and the average score was calculated. <Test 7> Trans-2-hexen-1-ol (manufactured by Inoue Fragrance Manufacturing Co., Ltd.) was diluted with rapeseed oil (free-flowing canola oil manufactured by J-Oil Mills Co., Ltd.) to prepare a thick oil containing 100 ppm of trans-2-hexen-1-ol. The thick oil was then diluted 10 times to prepare a cooking oil containing 10 ppm of trans-2-hexen-1-ol.

[0087] The fibrous bitter melon (containing momordicin, cucurbitacins, and other bittering components) was cut in half lengthwise and then thinly sliced. Each 50g group was soaked in water for 30 minutes. Then, 7g of the rapeseed oil, the thick oil, or the cooking oil was heated for 30 seconds in a frying pan preheated to 180°C for 30 seconds, and the 50g of the water-soaked bitter melon was added to the frying pan and fried for 4 minutes. The bitterness evaluation of the bitter melon fried in the rapeseed oil, the thick oil, and the cooking oil is shown in Table 8.

[0088] [Table 8]

[0089] The bitterness of the bitter melon fried in rapeseed oil containing the compound (3) was less than that of the bitter melon fried in rapeseed oil.

[0090] From the above results, it was confirmed that the bitterness of vegetables can be suppressed by the bitterness suppressor of the present invention.

Claims

1. A bitterness suppressor for foods and beverages, The composition contains at least one active ingredient selected from the group consisting of a ketone represented by the following formula (1), a saturated aliphatic alcohol represented by the following formula (2), an unsaturated aliphatic alcohol represented by the following formula (3), and an unsaturated aliphatic alcohol represented by the following formula (4), 【Chemistry 1】 【Chemistry 2】 【Transformation 3】 【Chemistry 4】 In the formulas (1) to (4), R １ is an alkyl group having 1 to 6 carbon atoms, and R ２ is a methyl group or an ethyl group, and R ３ is an alkyl group having 1 to 5 carbon atoms, and R ４ is an alkyl group having 1 to 5 carbon atoms, and R ５ is a methylene group or an ethylene group,

2. The bitterness suppressor according to claim 1, wherein the ketone represented by formula (1) comprises at least one selected from the group consisting of 3-pentanone, 2-heptanone, and 2-octanone; the saturated aliphatic alcohol represented by formula (2) comprises at least one selected from the group consisting of 1-pentanol, 1-hexanol, and 1-octanol; and the unsaturated aliphatic alcohol represented by formula (3) or (4) comprises at least one selected from the group consisting of trans-2-penten-1-ol, trans-2-hexen-1-ol, trans-3-hexen-1-ol, trans-2-hepten-1-ol, cis-2-penten-1-ol, cis-2-hexen-1-ol, cis-3-hexen-1-ol, and cis-2-hepten-1-ol.

3. The bitterness suppressor according to claim 1, which is an oil composition containing an edible oil containing at least one selected from the group consisting of a ketone represented by formula (1), a saturated aliphatic alcohol represented by formula (2), an unsaturated aliphatic alcohol represented by formula (3), and an unsaturated aliphatic alcohol represented by formula (4).

4. The method includes a step of blending at least one selected from the group consisting of a ketone represented by the following formula (1), a saturated aliphatic alcohol represented by the following formula (2), an unsaturated aliphatic alcohol represented by the following formula (3), and an unsaturated aliphatic alcohol represented by the following formula (4) into edible fats and oils, 【Transformation 5】 【Transformation 6】 【Transformation 7】 【Transformation 8】 In the formulas (1) to (4), R １ is an alkyl group having 1 to 6 carbon atoms, and R ２ is a methyl group or an ethyl group, and R ３ is an alkyl group having 1 to 5 carbon atoms, and R ４ is an alkyl group having 1 to 5 carbon atoms, and R ５ is a methylene group or an ethylene group.

5. 5. The method for producing an edible oil-containing composition according to claim 4, wherein the edible oil-containing composition is used to suppress bitterness in foods and beverages.

6. 5. The method for producing an edible oil-containing composition according to claim 4, wherein the total content of the ketone represented by formula (1), the saturated aliphatic alcohol represented by formula (2), the unsaturated aliphatic alcohol represented by formula (3), and the unsaturated aliphatic alcohol represented by formula (4) in the edible oil-containing composition is 0.01 mass ppm or more.

7. A method for producing a food or drink with reduced bitterness, comprising a step of blending the bitterness suppressor according to any one of claims 1 to 3 or an edible oil-and-fat-containing composition produced by the method according to any one of claims 4 to 6 into the food or drink.

8. 8. The method for producing a food or beverage with reduced bitterness described in claim 7, wherein the total content of the ketone represented by formula (1), the saturated aliphatic alcohol represented by formula (2), the unsaturated aliphatic alcohol represented by formula (3), and the unsaturated aliphatic alcohol represented by formula (4) in the food or beverage is 0.001 mass ppm or more.

9. A method for suppressing the bitterness of a food or drink, comprising a step of blending the bitterness suppressor according to any one of claims 1 to 3 or the edible oil-and-fat-containing composition produced by the method according to any one of claims 4 to 6 into the food or drink.

10. 10. The method for suppressing the bitterness of a food or beverage according to claim 9, wherein the total content of the ketone represented by formula (1), the saturated aliphatic alcohol represented by formula (2), the unsaturated aliphatic alcohol represented by formula (3), and the unsaturated aliphatic alcohol represented by formula (4) in the food or beverage is 0.001 mass ppm or more.

11. A food or drink comprising the bitterness suppressor according to any one of claims 1 to 3 or an edible fat-and-oil-containing composition produced by the method according to any one of claims 4 to 6.

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