Method for producing a composition that improves unpleasant flavors

Abstract

To provide a composition effective for improving an unpleasant flavor.SOLUTION: An unpleasant flavor improving composition includes a palmitoleic acid as an active ingredient. Preferably, an unpleasant flavor is an unpleasant flavor felt from bean-containing food and beverages, vinegar-containing food and beverages, wheat-containing food and beverages, almond-containing food and beverages, vitamin-containing food and beverages, or milk-containing food and beverages. For instance, the unpleasant flavor may be one or more kinds selected from a group including sourness, acid odor, harshness, bitterness, astringency, whey odor, grain odor, fragrance, grease degradation odor, grassy odor, musty odor, sulfur odor and phenolic odor.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a method for producing a composition for improving unpleasant fragrance.

Background Art

[0002] Consumers' demands for the fragrance and taste (sometimes generally referred to as fragrance in this specification) of various consumer goods such as food and beverages and cosmetics are increasing, and a plurality of techniques for improving unpleasant fragrance have been proposed.

[0003] For example, Patent Document 1 proposes that by adding 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid or 10-dodecenoic acid to food and beverages, the unpleasant taste, particularly the unpleasant taste derived from sourness, bitterness and astringency, in food and beverages can be reduced, and the flavor of food and beverages can be improved. Further, Patent Document 2 describes an odor inhibitor for the odor of casein or collagen, which contains chlorogenic acid as an active ingredient.

Prior Art Documents

Patent Documents

[0004]

Patent Document 1

Patent Document 2

Summary of the Invention

Problems to be Solved by the Invention

[0005] However, the materials conventionally used for improving unpleasant fragrance have not been able to sufficiently cope with the improvement of various unpleasant fragrances, and the discovery of useful materials for improving unpleasant fragrance has been an issue. Therefore, an object of the present invention is to provide a composition for improving unpleasant fragrance containing a compound useful for improving unpleasant fragrance.

Means for Solving the Problems

[0006] In light of the above problems, the inventors conducted diligent research and found that compositions containing palmitoleic acid are useful for improving unpleasant flavors, leading to the present invention.

[0007] Thus, a brief overview of some of the representative inventions disclosed in this application is as follows: [1] A method for producing an unpleasant flavor-improving composition containing palmitoleic acid as an active ingredient, comprising steps 1 and 2 below. (Step 1) A step of preparing a composition containing a compound that contains palmitoleic acid in its molecule. (Step 2) A step of obtaining an enzyme-treated product containing palmitoleic acid released from the compound by enzymatically treating the composition prepared in Step 1. [2] A method for producing an unpleasant flavor-improving composition according to [1], wherein the enzyme treatment is a lipase treatment. [3] A method for producing an unpleasant flavor-improving composition according to [1] or [2], further comprising the step of emulsifying the enzyme-treated product after step 2. [4] A method for producing an unpleasant flavor-improving composition according to [1] or [2], wherein the composition is a plant fruit or seed, its juice or oil, or the residue of the juice or oil. [5] A method for producing an unpleasant flavor-improving composition according to [1] or [2], wherein the composition is extracted from macadamia seeds. [Effects of the Invention]

[0008] The present invention makes it possible to provide an unpleasant flavor improving composition that is effective in improving unpleasant flavors. [Modes for carrying out the invention]

[0009] The present invention will be described in more detail below, with specific examples. In this specification, "~" means a range including the lower and upper limits, concentration (ppt, ppb, ppm, etc.) and % represent mass concentration and mass %, respectively, unless otherwise specified, and concentration refers to the final concentration unless otherwise specified.

[0010] [Unpleasant flavor improving composition] A composition for improving unpleasant flavors according to one embodiment of the present invention (which may also be referred to as the "present composition for improving unpleasant flavors" in this specification) is a composition containing palmitoleic acid that can be added to various consumer goods to improve their unpleasant flavors. Unless otherwise specified, palmitoleic acid refers to free palmitoleic acid.

[0011] In this specification, “addition” includes at least one of simply adding to a substance by spraying, dropping, or other means, and mixing with a substance.

[0012] In this specification, "flavor" typically refers to the senses including smell and taste, and "unpleasant flavor" refers to an unpleasant flavor that can be perceived by animals, typically by humans. In one embodiment of the present invention, the unpleasant flavor may include one or more selected from the group consisting of sourness, sour odor, astringency, bitterness, astringency, whey odor, grain odor, savory aroma, oily odor, grassy odor, moldy odor, sulfurous odor, and phenolic odor. In another embodiment of the present invention, one or more selected from the group consisting of sourness, sour odor, astringency, bitterness, astringency, whey odor, grain odor, savory aroma, oily odor, grassy odor, moldy odor, sulfurous odor, and phenolic odor may be an unpleasant flavor derived from legumes (especially soybeans), wheat, almonds, vitamins, milk, or vinegar. In other words, the unpleasant flavor-improving composition of the present invention can be effectively used to improve the unpleasant flavor of, for example, foods and beverages containing legumes (especially soybeans), foods and beverages containing grains, foods and beverages containing almonds, foods and beverages containing vitamins, foods and beverages containing milk, or foods and beverages containing vinegar. Grain odor refers to a sensation that includes an aroma reminiscent of the dried flour of grains such as barley and wheat. Whey odor refers to a sensation of aroma that includes a slightly sour, animalistic or fishy smell. Degraded oil odor refers to a sensation of aroma that includes an aroma like stale oil, such as that found in frying oil. Phenolic odor refers to a sensation of aroma that includes a pungent smell like that of a drug.

[0013] In this specification, "improvement" includes making the unpleasant flavors perceived from consumer goods weaker or substantially undetectable compared to when the unpleasant flavor improving composition is not added. The unpleasant flavor improving composition can also be used as a flavor-imparting composition capable of improving unpleasant flavors, and such use is also included in the unpleasant flavor improvement applications of the present invention.

[0014] Examples of the unpleasant flavor-improving compositions mentioned above include various additives containing palmitoleic acid that can be added to various consumer goods such as food and beverages, cosmetics, and health and hygiene products. More specific examples include fragrance compositions, various animal and plant extracts, or fermented, enzyme-treated, or heat-treated products of various animal and plant raw materials that contain palmitoleic acid and can be added to various consumer goods. These can take the form of water-soluble or oil-soluble solvent solutions, emulsified formulations, powder formulations, or other solid formulations (such as solid fats), but the present invention is not limited to these examples.

[0015] The unpleasant flavor-improving composition may contain, in addition to palmitoleic acid, any other components such as solvents, dispersion media, flavor-imparting components other than palmitoleic acid, antioxidant components, and other auxiliary components (specific examples are described later), but may also consist substantially of palmitoleic acid alone. If the unpleasant flavor-improving composition contains components other than palmitoleic acid, the concentration of palmitoleic acid in the unpleasant flavor-improving composition can be arbitrarily determined according to the target of the composition and its aroma characteristics.

[0016] As an example of the concentration of palmitoleic acid in the unpleasant flavor-improving composition, if the unpleasant flavor-improving composition contains substantially only palmitoleic acid, or only palmitoleic acid and its solvent or dispersion medium (specific examples are described later), the range can be exemplified as 10 ppb to 100%, and a preferred example is a range of 10 ppm to 99%. For example, commercially available palmitoleic acid with a purity of 95% or higher (e.g., 98%, 99%, etc.) can be used as the unpleasant flavor-improving composition.

[0017] As an example of the concentration of palmitoleic acid in the unpleasant flavor improving composition, especially when the unpleasant flavor improving composition contains components other than palmitoleic acid and its solvent, the concentration of palmitoleic acid in the unpleasant flavor improving composition can be arbitrarily determined according to the target of the unpleasant flavor improving composition and its aroma characteristics, as described above, and should be set to an appropriate concentration so that it can be added to consumer goods at a concentration that produces an unpleasant flavor improving effect, for example, 10 ppm to 90%, more specifically, with lower limits of 10 ppm, 100 ppm, 1000 ppm, 1 The lower limit can be any combination of these lower and upper limits, but is not limited to these. Preferably, the range is 1% to 60%, more preferably 5% to 55%, even more preferably 10% to 50%, and still more preferably 15% to 35%. Furthermore, although it depends on the formulation of the unpleasant flavor improving composition, setting the palmitoleic acid concentration in the unpleasant flavor improving composition to 10 ppm to 90% makes it easier to obtain an unpleasant flavor improving effect on consumer goods without the palmitoleic acid-derived flavor being excessively prominent. However, depending on the unpleasant flavor improving composition in question, the flavor to which it is added, and other conditions, palmitoleic acid may be included at a concentration outside the range of 10 ppm to 90%.

[0018] In this unpleasant odor-improving composition, specific examples of any other components that may be further contained in addition to palmitoleic acid include various types of fragrance compounds, fragrance compositions, dyes, vitamins, functional substances, fish extracts, livestock extracts, animal and plant extracts, animal and plant oils and fats, yeast extracts, animal and plant proteins, animal and plant protein hydrolysates, starches, dextrins, saccharides, amino acids, nucleic acids, organic acids, solvents, emulsifiers, specific gravity adjusters, antioxidants, and the like. For example, natural essential oils, natural fragrances, synthetic fragrances, etc. described in "Patent Office Gazette, Well-Known and Conventional Technology Collection (Fragrances), Part II, Food Flavors, Issued on January 14, 2000", "Investigation of the Actual State of Use of Food Flavor Compounds in Japan" (Report on Health Sciences Research in 2000, Japan Flavor Industry Association, Issued in March 2001), and "Synthetic Fragrances - Chemistry and Product Knowledge" (Supplemented New Edition Issued on December 20, 2016, Edited by the Synthetic Fragrance Editorial Committee, Chemical Industry Daily) can be cited.

[0019] As other examples of fragrance compounds, hydrocarbon compounds include monoterpenes such as α-pinene, β-pinene, myrcene, camphene, limonene, sesquiterpenes such as valencene, cedrene, caryophyllene, longifolene, and 1,3,5-undecatriene.

[0020] Alcohol compounds include saturated or unsaturated alcohols such as butanol, pentanol, 3-octanol, hexanol, (Z)-3-hexen-1-ol, prenol, 2,6-nonadienol, terpene alcohols such as linalool, geraniol, citronellol, tetrahydromyrcenol, farnesol, nerolidol, cedrol, terpineol, and aromatic alcohols such as benzyl alcohol, phenylethyl alcohol, and cinnamyl alcohol.

[0021] Examples of aldehyde compounds include saturated or unsaturated aldehydes such as acetaldehyde, hexanal, octanal, decanal, (E)-2-hexenal, 2,4-octadienal, terpene aldehydes such as citronellal, hydroxycitronellal, citral, myrtenal, perillyl aldehyde, and aromatic aldehydes such as benzaldehyde, cinnamaldehyde, amyl cinnamaldehyde, vanillin, ethyl vanillin, heliotropin, p-tolyl aldehyde.

[0022] Examples of ketone compounds include saturated or unsaturated ketones such as 2-heptanone, 2-undecanone, 1-octen-3-one, acetoin, diketones and hydroxyketones such as diacetyl, 2,3-pentanedione, maltol, ethyl maltol, cycloten, 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, β-damascenone, and aromatic ketones such as raspberry ketone.

[0023] Examples of furan or ether compounds include furfuryl alcohol, furfural, rose oxide, linalool oxide, menthofuran, theaspirane, estragole, eugenol, 1,8-cineole, etc.

[0024] Examples of ester compounds 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, ethyl nonanoate, terpene alcohol esters such as linalyl acetate, geranyl acetate, lavandulyl acetate, terpenyl acetate, and aromatic esters such as benzyl acetate, benzyl butyrate, methyl salicylate , benzyl salicylate, methyl cinnamate, cinnamyl propionate, ethyl benzoate, cinnamyl isovalerate, ethyl 3-methyl-2-phenylglycidate.

[0025] Examples of lactone compounds include saturated and unsaturated lactones such as γ-decalactone, γ-dodecalactone, δ-decalactone, δ-dodecalactone, 7-decene-4-olide, and 2-decene-5-olide.

[0026] Examples of acidic 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.

[0027] Examples of nitrogen-containing compounds include pyridine, alkyl-substituted pyrazines, methyl anthranilate, and trimethylpyrazine.

[0028] Examples of sulfur-containing compounds include methanethiol, dimethyl sulfide, dimethyl disulfide, allyl isothiocyanate, 3-methyl-2-butene-1-thiol, 3-methyl-2-butanethiol, 3-methyl-1-butanethiol, 2-methyl-1-butanethiol, and furfuryl mercaptan.

[0029] Examples of 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.

[0030] Examples of various plant and animal extracts include extracts of herbs or spices, various tea extracts such as coffee, green tea, black tea, or oolong tea, and milk or dairy products and various enzyme hydrolysates such as lipases and / or proteases thereof.

[0031] Furthermore, it may be used in combination with known materials related to improving unpleasant flavors, such as Japanese Patent Publication No. 2021-171023, Japanese Patent Publication No. 2021-142111, Japanese Patent Publication No. 2021-108822, Japanese Patent Publication No. 2020-188705, Japanese Patent Publication No. 2018-87153, Japanese Patent Publication No. 2015-144621, Japanese Patent No. 6009616, Japanese Patent Publication No. 2015-67558, Japanese Patent Publication No. 6158664, Japanese Unexamined Patent Publication No. 2015-67557, Japanese Unexamined Patent Publication No. 2014-240360, Japanese Patent Publication No. 6216543, Japanese Unexamined Patent Publication No. 2014-34517, Japanese Patent Publication No. 5220942, Japanese Unexamined Patent Publication No. 2013-143930, Japanese Patent Publication No. 5019659, Japanese Unexamined Patent Publication No. 2013-21926, Japanese Patent Publication No. 4925488, Japanese Unexamined Patent Publication No. 2012-80840, Japanese Patent Publication No. 5198533 Publications, JP 2012-80778, JP 6005333, JP 2012-34603, JP 5340238, JP 2011-103873, JP 4562049, JP 2011-223942, JP 5349399, JP 2011-103774, JP 4606505, JP 2008-253217, JP 200 You may adopt the methods described in Japanese Patent Publication No. 6-104257, Japanese Patent Publication No. 4391378, Japanese Unexamined Patent Publication No. 2004-248611, Japanese Patent Publication No. 4216091, Japanese Unexamined Patent Publication No. 2004-18829, Japanese Unexamined Patent Publication No. 2003-210119, Japanese Patent Publication No. 3830137, Japanese Unexamined Patent Publication No. 2003-96486, Japanese Unexamined Patent Publication No. Hei 9-221429, Japanese Patent Publication No. 3431383, and Japanese Unexamined Patent Publication No. Hei 8-119843.

[0032] Particularly preferred are animal and plant extracts that can be used in combination, which are obtained by adding amino acids and sugars to animal and plant extracts as appropriate and then heat-treating them (for example, in the range of 80 to 200°C, preferably 100 to 180°C) (for example, JP 2018-102308, JP 2018-102309, JP 2018-102310, JP 2018-102307, JP 2017- Examples include those described in Japanese Patent Publication No. 51206, International Publication No. 2016 / 72114, International Publication No. 2016 / 72111, International Publication No. 2016 / 63394, Japanese Patent Publication No. 2015-112038, Japanese Patent Publication No. 2013-252111, Japanese Patent Publication No. 2013-252113, Japanese Patent Publication No. 2013-252112, or Japanese Patent Publication No. 2013-252114, etc.

[0033] Since palmitoleic acid is oil-soluble, by making this unpleasant flavor-improving composition an oil-in-water emulsifier, it can be added to various foods and beverages without causing separation of palmitoleic acid from water, making it usable in a wide range of foods and beverages. Furthermore, by making it an emulsifier, the flavor-improving effect lasts longer than that of palmitoleic acid itself or a solution of palmitoleic acid simply dissolved in a solvent, and the effect on improving unpleasant aftertaste is particularly enhanced.

[0034] In another aspect of the present invention, the unpleasant flavor improving composition may be a plant fruit or seed containing palmitoleic acid, its juice, oil, or the residue of the juice or oil. Furthermore, an emulsified preparation may be used, and a powdered preparation may be used, which may be further processed into a powder (specific examples of emulsification and powdering procedures will be described later).

[0035] In yet another aspect of the present invention, the unpleasant flavor improving composition can be an enzyme-treated product of a composition containing a compound containing palmitoleic acid in its molecule (hereinafter also referred to as a palmitoleic acid encapsulated compound), wherein the enzyme-treated product contains palmitoleic acid released from the palmitoleic acid encapsulated compound by the enzyme treatment.

[0036] In this specification, a compound containing palmitoleic acid in its molecule (palmitoleic acid-encapsulated compound) means a compound in which palmitoleic acid is contained within its molecular structure or in part thereof, and from which palmitoleic acid can be released by enzymatic treatment (specific examples of enzymatic treatment procedures will be described later). Typical examples include glycerides having a structure in which the carboxyl group of palmitoleic acid is ester-bonded to the hydroxyl group of glycerol, and the enzymatic treatment is lipase treatment, in which palmitoleic acid is released by the hydrolysis of the ester bond by lipase. Specific examples of palmitoleic acid-encapsulated compounds include triacylglycerols (also called triglycerides) in which at least one of the three ester bonds is ester-bonded to palmitoleic acid. However, the present invention is not limited to this embodiment, and any compound from which palmitoleic acid can be released by hydrolysis by enzymatic treatment or other actions can be considered a palmitoleic acid-encapsulated compound.

[0037] Furthermore, the composition containing the palmitoleic acid encapsulated compound may contain both palmitoleic acid and the palmitoleic acid encapsulated compound. In this case, depending on the desired palmitoleic acid concentration, the enzymatic treatment may be performed to release palmitoleic acid from the palmitoleic acid encapsulated compound, or the composition containing palmitoleic acid may be used as is (or further emulsified and / or powdered) as the unpleasant flavor improving composition of the present invention without such enzymatic treatment.

[0038] Compositions containing palmitoleic acid-encapsulated compounds are preferably plant fruits or seeds, their juice, oil, or residues from juice or oil extraction, and more preferably oil extracted from plant fruits or seeds. Specific examples include, but are not limited to, macadamia nut oil, avocado oil, almond oil, cashew nut oil, hazelnut oil, and pistachio oil containing palmitoleic acid-encapsulated compounds.

[0039] When the unpleasant flavor-improving composition is a lipase-treated product, the palmitoleic acid concentration can be in the range of 10-40%, preferably 15-35%, from the viewpoint of ensuring a certain level of palmitoleic acid concentration to reduce the amount added to consumer goods, and from the viewpoint of cost-effectiveness in terms of lipase treatment time and treatment costs. When the composition is an emulsified formulation, the palmitoleic acid concentration can be in the range of 100 ppm to 1%, and a range of 2000 ppm to 5000 ppm is an example of a suitable concentration range, from the viewpoint of ensuring a certain level of palmitoleic acid concentration to reduce the amount added to consumer goods. When the composition is a powder formulation, the palmitoleic acid concentration can be in the range of 100 ppm to 5%, and a range of 1% to 3% is an example of a suitable concentration range, from the viewpoint of ensuring a certain level of palmitoleic acid concentration to reduce the amount added to consumer goods. However, depending on the target of the unpleasant flavor-improving composition and the desired additive effect, the palmitoleic acid concentration can also be set to a concentration outside the ranges exemplified here.

[0040] [Method for producing a composition to improve unpleasant flavors and aromas] The method for producing the unpleasant flavor-improving composition of this invention involves adding a composition containing palmitoleic acid (in this specification, this includes both compositions substantially composed of palmitoleic acid and compositions containing palmitoleic acid and other components) to a composition that can be added to consumer goods. The composition obtained by this addition can be the unpleasant flavor-improving composition of this invention. Examples of compositions that can be added to various consumer goods include compositions containing one or more solvents, antioxidants, pigments, and other additives that can be added to food and beverages, cosmetics, and health and hygiene products. Furthermore, the unpleasant flavor composition of this invention may also be made into an emulsified preparation, a powder preparation, or other solid preparation (such as a solid fat).

[0041] There are no particular restrictions on the type of solvent used. 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, and diethyl phthalate. Of these, ethanol or propylene glycol are 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 (for example, processed oils such as medium-chain fatty acid triglycerides and short-chain fatty acid triglycerides such as triacetin and trippropionine), harcoline, various essential oils, and triethyl citrate.

[0042] To obtain the unpleasant flavor-improving composition in question as an emulsified preparation, palmitoleic acid or a composition containing palmitoleic acid may be diluted with a suitable vegetable oil, and if necessary, a specific gravity adjuster (such as sucrose acetate isobutyrate) and an oil-soluble antioxidant may be added, after which it can be emulsified with a water-soluble solvent and an emulsifier. There are no particular restrictions on the emulsification method. By using various types of emulsifiers that have been conventionally 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, 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, and sodium caseinate, and performing emulsification using a homomixer, colloid mill, rotary disc homogenizer, high-pressure homogenizer, etc., a highly stable emulsified liquid can be obtained. The amount of emulsifiers used is not strictly limited and can be varied over a wide range depending on the type of emulsifier used, but generally, an amount of about 0.01 to about 100 parts by mass, preferably about 0.1 to about 50 parts by mass, per 1 part by mass of palmitoleic acid is appropriate. In addition, to stabilize the emulsification, the water-soluble solvent can contain, in addition to water, one or more types of polyhydric alcohols such as glycerin, propylene glycol, sorbitol, maltitol, sucrose, glucose, trehalose, sugar solution, and reduced starch syrup.

[0043] Furthermore, the resulting emulsified liquid can be dried to produce a powder formulation if desired. During the powdering process, sugars such as gum arabic, trehalose, dextrin, sugar, lactose, glucose, starch syrup, and reduced starch syrup may be added as needed. The amounts used can be appropriately selected according to the desired characteristics of the powder formulation.

[0044] Another embodiment of the method for producing the unpleasant flavor-improving composition is a method comprising at least the following steps 1 and 2. The enzyme-treated product obtained in step 2 can be used as is as the unpleasant flavor-improving composition. (Step 1) A step to prepare a composition containing a compound that contains palmitoleic acid in its molecule (palmitoleic acid-encapsulated compound). (Step 2) A step to obtain an enzyme-treated product containing palmitoleic acid liberated from the compound by enzymatically treating the composition prepared in Step 1 (sometimes referred to as the enzyme-treated product).

[0045] As described above, enzymatic treatment refers to a process that allows for the release of palmitoleic acid from palmitoleic acid-encapsulated compounds. The enzymatically treated product obtained in step 2 can be used as the unpleasant flavor-improving composition.

[0046] Furthermore, the process may include adding a composition containing palmitoleic acid to the composition of step 1 either before step 1 or between steps 1 and 2, for the purpose of increasing the palmitoleic acid concentration.

[0047] The composition is preferably, as described above, a plant fruit or seed, its juice or oil, or the residue from said juice or oil extraction. Preferably, it is an oil extracted from a plant fruit or seed, more preferably an oil extracted from a plant seed, and specific examples include, but are not limited to, macadamia nut oil, avocado oil, almond oil, cashew nut oil, hazelnut oil, and pistachio oil.

[0048] As an example of a specific enzymatic treatment procedure, one can describe a treatment procedure in which oil extracted from plant seeds containing palmitoleic acid-encapsulated compounds is appropriately heat-sterilized (for example, at 70-98°C for 5-30 minutes), and then lipase and water are added and the mixture is lipase-treated at the optimal temperature of the lipase for about 10-30 hours to release palmitoleic acid from the palmitoleic acid-encapsulated compounds. After that, if necessary, further heat sterilization, removal of the aqueous layer, and filtration can be performed to obtain the unpleasant flavor-improving composition. The concentration of palmitoleic acid in the lipase-treated product obtained in this way is not particularly limited and can be, for example, within the concentration range described above.

[0049] The enzyme-treated product can also be used as an emulsified preparation by the emulsification process described above, or as a powdered preparation by the powdering process described above, and the unpleasant flavor-improving composition can also be used as such. The palmitoleic acid concentration in the emulsified preparation or powdered preparation is not particularly limited, and the above-mentioned concentration range is an example.

[0050] In another aspect of the present invention, a method for producing an unpleasant flavor improving composition is provided, which includes adding the unpleasant flavor improving composition obtained from a composition containing a palmitoleic acid-encapsulated compound as described above 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, dyes, and other additives that can be added to food and beverages, cosmetics, and health and hygiene products.

[0051] Furthermore, in another aspect of the present invention, the unpleasant flavor-improving composition obtained by any method can be added to another flavor-improving composition to produce the flavor-improving composition to which the composition is added as an unpleasant flavor-improving composition. The unpleasant flavor-improving composition thus produced can be used as an additive composition for various consumer goods such as food and beverages, cosmetics, and health and hygiene products in the manufacture of various consumer goods.

[0052] [Method for improving unpleasant flavors in consumer goods and consumer goods] By adding the unpleasant flavor-improving composition to various consumer goods (typically, food and beverages, cosmetics, health and hygiene products, etc.), consumer goods with suppressed unpleasant flavors can be manufactured. Therefore, in this invention, the method for improving the unpleasant flavor of various consumer goods can also be said to be a method for manufacturing consumer goods with suppressed unpleasant flavors. The timing of adding the unpleasant flavor-improving composition to various consumer goods is arbitrary. The unpleasant flavor-improving composition itself may be added to various consumer goods such as food and beverages, cosmetics, and health and hygiene products, or it may be added to various consumer goods in combination with one or more other flavor-imparting compositions (for example, one or more selected from water-soluble fragrance compositions, emulsified fragrance compositions, any fragrance compound, natural essential oils (for example, fragrance compounds described in the aforementioned "Japan Patent Office Gazette, Collection of Well-Known and Conventional Technologies (Fragrances) Part II Food Fragrances," "Survey on the Actual Use of Food Fragrance Compounds in Japan," and "Synthetic Fragrances: Chemistry and Product Knowledge")).

[0053] The food and beverages to which this unpleasant flavor-improving composition can be added are not particularly limited and may have any flavor (also called aroma), but examples of flavors include various citrus flavors such as lemon, orange, grapefruit, lime, mandarin, mandarin orange, kabosu, sudachi, hassaku, iyokan, yuzu, shikwasa, kumquat; strawberry, blueberry, raspberry, apple, cherry, plum, apricot, peach, pineapple, banana, melon, mango, papaya, Various fruit flavors such as kiwi, pear, grape (muscat, Kyoho, etc.), lychee, and passion fruit; dairy flavors or flavors containing dairy, such as milk, yogurt, butter, and custard; vanilla flavor; various tea flavors such as green tea, matcha, hojicha, black tea, oolong tea, barley tea, corn tea, buckwheat tea, pu-erh tea, and herbal tea; coffee flavor; cola flavor; cocoa flavor; various mint flavors such as spearmint and peppermint; cinnamon Flavors of various spices or herbs such as mon, chamomile, cardamom, caraway, cumin, cloves, pepper, coriander, sansho pepper, shiso, ginger, star anise, thyme, chili pepper, nutmeg, basil, marjoram, rosemary, bay leaf, wasabi, sansho pepper, and garlic; flavors of various nuts such as almonds, cashews, and walnuts; and flavors of wine, brandy, whiskey, rum, gin, liqueurs, sake, shochu, and beer. Examples of food and beverages having one or more of the following flavors: various alcoholic beverage flavors; vegetable flavors such as carrots, tomatoes, cucumbers, onions, corn, and potatoes, especially legume flavors such as soybeans, peas, and chickpeas; meat flavors such as chicken, pork, beef, lamb, and horse meat; seafood flavors; broth (bouillon) flavors from vegetables, meat, and seafood; consommé flavors; caramel flavors; grain flavors such as barley and wheat; and vinegar flavors such as rice vinegar, black vinegar, and apple cider vinegar.In other words, the food or beverage may contain only one of the above flavors, or it may contain two or more flavors, and the multiple flavors may be of the same type or different types. For example, an example of the former would be a food or beverage that contains multiple fruit flavors such as banana, peach, and apple (so-called mixed fruit flavor), and an example of the latter would be a food or beverage that contains citrus flavors such as lemon and milk flavors (such as citrus-flavored lactic acid bacteria beverages), or a food or beverage that contains mint flavors or citrus flavors and cola flavors (such as mint or lemon-flavored cola beverages). However, any flavor that can improve unpleasant flavors with the unpleasant flavor improving composition is acceptable.

[0054] Examples of flavors in which the present unpleasant flavor-improving composition is highly effective in improving unpleasant flavors include flavors in which at least one of the following can be perceived: sourness, sour odor, astringency, bitterness, astringency, whey odor, grain odor, roasted aroma, oily odor, grassy odor, moldy odor, sulfurous odor, and phenolic odor.

[0055] More specific examples of food and beverages include rice crackers, rice crackers, puffed rice crackers, mochi, manju, uiro, bean paste, yokan, mizuyokan, kintama, jelly, castella, candy, biscuits, crackers, potato chips, cookies, pies, pudding, frozen desserts, ice cream, ice milk, buttercream, custard cream, cream puffs, waffles, sponge cake, donuts, chocolate, chewing gum, caramel, candy, and peanut paste. Other pastes, whipped cream and other confectionery or confectionery ingredients; bread, udon, ramen, Chinese noodles, sushi, mixed rice, fried rice, pilaf, gyoza wrappers, shumai wrappers, okonomiyaki, takoyaki and other breads, noodles, rice dishes, and other grains; pickles such as fermented rice bran pickles, pickled plums, fukujinzuke, bettara pickles, senmaizuke, rakkyo, miso pickles, takuan pickles, and pickling bases for these; mackerel, sardines, saury, salmon, tuna, bonito, whale, ka Fish such as flounder, sand eel, and sweetfish; squid such as Japanese flying squid, spear squid, cuttlefish, and firefly squid; octopus such as common octopus and baby octopus; shrimp such as kuruma prawn, spot prawn, spiny lobster, and black tiger prawn; crabs such as king crab, snow crab, swimming crab, and hairy crab; shellfish such as clams, cockles, scallops, oysters, and mussels; meats such as chicken, pork, beef, lamb, and horse meat; canned goods, boiled fish, tsukudani, surimi, and processed seafood products (chikuwa, kamaboko, Fried fish cakes (such as fried fish cakes and crab leg fish cakes), fried foods, tempura, curry, stew, beef stew, Hayashi rice sauce, meat sauce, mapo tofu, hamburgers, dumplings, instant rice mixes, soups (corn soup, tomato soup, consommé soup, etc.), meatballs, braised pork, canned meat, boiled vegetables, Chikuzen-ni (a type of Japanese stew), oden (Japanese hot pot), hot pot dishes, take-out prepared foods, noodles such as ramen, soba, udon, and somen, and soups used with them, vegetable soups, and other processed foods made from animal and plant ingredients;Table salt, seasoned salt, soy sauce, powdered soy sauce, miso, powdered miso, moromi, hishio, furikake, ochazuke mix, margarine, mayonnaise, dressing, vinegar, sanbaizu, powdered sushi vinegar, Chinese seasoning mix, tempura dipping sauce, noodle soup (kombu dashi or katsuobushi dashi, etc.), sauce (medium-thick sauce, tomato sauce, etc.), ketchup, yakiniku sauce, curry roux, stew mix, soup base, dashi base (kombu dashi or katsuobushi dashi, etc.), compound seasonings, new mirin, mixed flours such as fried chicken flour and takoyaki flour, etc. Any seasonings, animal or plant-based broth-flavored foods and beverages to which these seasonings have been added; dairy products such as cheese, yogurt, butter, and fresh cream; fruit beverages using fruit juice, pulp, seeds, or peel of fruits such as apples, grapes, mangoes, peaches, and citrus fruits (grapefruit, oranges, lemons, etc.); vegetables such as tomatoes, bell peppers, celery, melons, bitter melons, carrots, potatoes, asparagus, bracken, and fiddlehead ferns, as well as vegetable beverages and vegetable soups containing these vegetables. Examples include: vegetable-containing foods and beverages; beverages such as coffee, cocoa, green tea, black tea, oolong tea, soft drinks, carbonated drinks, cola drinks, lactic acid bacteria drinks, milk-containing beverages (milk tea, café au lait, etc.), and fruit or fruit juice-containing beverages (fruit teas such as lemon tea and orange tea); beverages containing medicinal herbs and herbs; functional beverages such as cola drinks, sports drinks, honey drinks, vitamin supplements, mineral supplements, nutritional drinks, and nourishing drinks; non-alcoholic beverages such as alcohol-flavored beverages (non-alcoholic beer, non-alcoholic chuhai, etc.) with various alcoholic flavors (beer flavor, plum wine flavor, chuhai flavor, etc.); beer-flavored beverages (also called beer-flavored beverages) including wine, shochu, awamori, sake, beer, chuhai, cocktail drinks, sparkling wine, fruit wine, medicinal wine, and so-called "third beer"; other brewed alcoholic beverages (sparkling), liqueurs (sparkling), or alcoholic beverages containing these; and more.

[0056] Particularly preferred examples of consumer goods to which the unpleasant flavor-improving composition is to be added include food and beverages containing at least one selected from legumes (especially soybeans), grains, almonds, vinegar, milk, and vitamins. Specific examples of soybean-containing food and beverages include tofu, fried tofu, thick fried tofu, soy milk, okara (soy pulp), natto (fermented soybeans), miso, soy sauce, boiled beans, kinako (roasted soybean flour), yuba (tofu skin), and plant protein made from soybeans (sometimes referred to as soy protein in this specification), with soy milk and soy protein being particularly preferred. Examples of other legumes include pea paste and protein, and chickpea paste and protein. Examples of grain-containing food and beverages include products using barley, with oatmeal and oat milk being preferred examples. Examples of almond-containing food and beverages include almond paste and almond milk. Specific examples of vinegar-containing foods and beverages include rice vinegar, grain vinegar, black vinegar, wine vinegar, apple cider vinegar, balsamic vinegar itself, and various beverages and seasonings containing these, with soft drinks or functional beverages containing vinegar being particularly preferred. Specific examples of milk-containing foods and beverages include milk itself, such as cow's milk, goat's milk, sheep's milk, and mare's milk, and various dairy products made from these milks. Specific examples of dairy products include modified milk, processed milk, skim milk, skimmed concentrated milk, lactic acid bacteria beverages, milk beverages, fermented milk (yogurt, etc.), butter, cheese, cream, ice cream, condensed milk, powdered milk, whey powder, buttermilk powder, and various beverages containing or manufactured using these (such as various tea beverages containing milk, like milk tea). Specific examples of vitamin-containing foods and beverages include vitamin drinks and vitamin-containing supplement tablets. However, the additives for the unpleasant flavor-improving composition are not limited to these.

[0057] The concentration of palmitoleic acid in various consumer goods such as food and beverages, cosmetics, and health and hygiene products to which this unpleasant flavor-improving composition is added can be arbitrarily determined according to the flavor of the consumer goods and the desired degree of effect.

[0058] The inventors have confirmed that unpleasant flavors in edible consumer goods (typically food and beverages) can be suppressed within a concentration range of 1 ppb to 100 ppm of palmitoleic acid. For example, the lower limit can be any of 1 ppb, 10 ppb, 100 ppb, 1 ppm, or 10 ppm, and the upper limit can be any of 100 ppm, 10 ppm, 1 ppm, 100 ppb, or 10 ppb, and the concentration range is not limited to any combination of these lower and upper limits. Preferred specific examples of concentration ranges include the ranges of 10 ppb to 100 ppm, 100 ppb to 10 ppm, 100 ppb to 1 ppm, and 10 ppb to 100 ppm. [Examples]

[0059] The present invention will be described in more detail below with reference to examples. However, the present invention is not limited to these examples.

[0060] [Example 1] Confirmation of effect on improving unpleasant flavor 1: Food and beverage containing legumes 1 Commercially available unsweetened soy milk was prepared (hereinafter also referred to as the basic soy milk beverage). In addition, commercially available palmitoleic acid (purity 98%) was prepared and used as an unpleasant flavor improving composition according to one embodiment of the present invention (Product 1-1 of the present invention).

[0061] Next, product 1-1 of the present invention was added to the basic soy milk beverage so that the palmitoleic acid concentration was 100 ppm, 20 ppm, 1 ppm, 100 ppb, 10 ppb, or 1 ppb, to obtain a soy milk beverage according to one embodiment of the consumer goods of the present invention (products 1-2 to 1-7 of the present invention; hereinafter, each will also be referred to as the soy milk beverage of the present invention).

[0062] In addition, commercially available palmitic acid (98% purity) and commercially available stearic acid (98% purity) were prepared. Then, palmitic acid and stearic acid were added to the basic soy milk beverage described above to a concentration of 1 ppm, and comparative soy milk beverages were obtained (Comparative product 1-1 (with palmitic acid added), Comparative product 1-2 (with stearic acid added)).

[0063] Next, a sensory evaluation was conducted on the flavor of the soy milk beverages of the present invention and comparative products. In the sensory evaluation, the basic soy milk beverage was designated as control product 1, and the flavors of the present invention products 1-2 to 1-7 and comparative products 1-1 to 1-2 were evaluated by 12 well-trained panelists with more than 10 years of experience. In the evaluation, unpleasant flavors of the present invention products and comparative products were scored according to the following criteria, and panelists were also asked to freely comment on flavors that they felt differed from control product 1. (Criteria) Regarding unpleasant flavors compared to the control product. "Significantly improved" = 4 points "Improved" = 3 points "Slightly improved" = 2 points "No improvement was observed" = 1 point "Unpleasant flavors were perceived more strongly" = 0 points

[0064] Table 1 shows the average scores and representative comments of the 12 panelists.

[0065] [Table 1]

[0066] As shown in Table 1, it was confirmed that adding a composition containing palmitoleic acid (Product 1-1 of the present invention) to food and beverages as an unpleasant flavor improving composition can improve the unpleasant flavor of those foods and beverages. On the other hand, palmitic acid and stearic acid, which are fatty acids similar to palmitoleic acid, did not have an insufficient effect in improving unpleasant flavors.

[0067] [Example 2] Confirmation of effect on improving unpleasant flavor 2: Milk-containing food and beverage (1) A commercially available yogurt was prepared (hereinafter also referred to as the basic yogurt). In addition, commercially available palmitoleic acid (purity 98%) was prepared and used as an unpleasant flavor improving composition according to one embodiment of the present invention (product 2-1 of the present invention).

[0068] Next, product 2-1 of the present invention was added to the basic yogurt so that the palmitoleic acid concentration was 100 ppm, 20 ppm, 1 ppm, 100 ppb, 10 ppb, or 1 ppb, to obtain yogurt according to one embodiment of the consumer goods of the present invention (products 2-2 to 2-7 of the present invention; hereinafter, each will also be referred to as the yogurt of the present invention).

[0069] Next, a sensory evaluation was conducted on the flavor of the yogurt of the present invention. In the sensory evaluation, the basic yogurt was used as control product 2, and the flavors of the present invention products 2-2 to 2-7 were compared to control product 2 by 12 well-trained panelists with more than 10 years of experience. In the evaluation, the panelists were asked to score the unpleasant flavors of the present invention products according to the following criteria, and were also asked to freely comment on the flavors they perceived as different from control product 2. (Criteria) Regarding unpleasant flavors compared to the control product. "Significantly improved" = 4 points "Improved" = 3 points "Slightly improved" = 2 points "No improvement was observed" = 1 point "Unpleasant flavors were perceived more strongly" = 0 points

[0070] Table 2 shows the average scores and representative comments of the 12 panelists.

[0071] [Table 2]

[0072] As shown in Table 2, it was confirmed that adding a composition containing palmitoleic acid (Product 2-1 of the present invention) to food and beverages as an unpleasant flavor improving composition can improve the unpleasant flavor of those foods and beverages.

[0073] [Example 3] Confirmation of effect on improving unpleasant flavor 3: Milk-containing food and beverage (2) A commercially available milk protein (Milk Protein Concentrate 480, manufactured by Fonterra) was prepared and diluted with water to create a milk protein beverage with a milk protein content of approximately 7.7% (hereinafter also referred to as the basic milk protein beverage). In addition, commercially available palmitoleic acid (purity 98%) was prepared and used as an unpleasant flavor improvement composition according to one embodiment of the present invention (Product 3-1 of the present invention).

[0074] Next, product 3-1 of the present invention was added to the basic milk protein beverage so that the palmitoleic acid concentration was 100 ppm, 20 ppm, 1 ppm, 100 ppb, or 10 ppb to obtain a milk protein beverage according to one embodiment of the consumer goods of the present invention (products 3-2 to 3-6 of the present invention; hereinafter, each will also be referred to as the milk protein beverage of the present invention).

[0075] Next, a sensory evaluation was conducted on the flavor of the milk protein beverage of the present invention. In the sensory evaluation, the basic milk protein beverage was used as control product 3, and the flavors of products 3-2 to 3-6 of the present invention were compared to control product 3 by 12 well-trained panelists with more than 10 years of experience. In the evaluation, unpleasant flavors of the products of the present invention were scored according to the following criteria, and panelists were also asked to freely comment on flavors that they felt differed from control product 3. (Criteria) Regarding unpleasant flavors compared to the control product. "Significantly improved" = 4 points "Improved" = 3 points "Slightly improved" = 2 points "No improvement was observed" = 1 point "Unpleasant flavors were perceived more strongly" = 0 points

[0076] Table 3 shows the average scores and representative comments of the 12 panelists.

[0077] [Table 3]

[0078] As shown in Table 3, it was confirmed that adding a composition containing palmitoleic acid (Product 3-1 of the present invention) to food and beverages as an unpleasant flavor improving composition can improve the unpleasant flavor of those foods and beverages.

[0079] [Example 4] Confirmation of effect on improving unpleasant flavor 4: Vinegar-containing food and beverages A commercially available black vinegar beverage (acetic acid concentration approximately 3 mg / mL) was prepared (hereinafter also referred to as the basic black vinegar beverage). In addition, commercially available palmitoleic acid (purity 99%) was prepared and used as an unpleasant flavor improvement composition according to one embodiment of the present invention (Product 4-1 of the present invention).

[0080] Next, product 4-1 of the present invention was added to the basic black vinegar beverage so that the palmitoleic acid concentration was 100 ppm, 20 ppm, 1 ppm, 100 ppb, 10 ppb, or 1 ppb, to obtain a black vinegar beverage according to one embodiment of the consumer goods of the present invention (products 4-2 to 4-7 of the present invention; hereinafter, each will also be referred to as the black vinegar beverage of the present invention).

[0081] Next, a sensory evaluation was conducted on the flavor of the black vinegar beverage of the present invention. In the sensory evaluation, the basic black vinegar beverage was used as control product 4, and the flavors of products 4-2 to 4-7 of the present invention were compared to control product 4 by 10 well-trained panelists with more than 10 years of experience. In the evaluation, unpleasant flavors of the products of the present invention were scored according to the following criteria, and panelists were also asked to freely comment on flavors that they felt differed from control product 4. (Criteria) Regarding unpleasant flavors compared to the control product. "Significantly improved" = 4 points "Improved" = 3 points "Slightly improved" = 2 points "No improvement was observed" = 1 point "Unpleasant flavors were perceived more strongly" = 0 points

[0082] Table 4 shows the average scores and representative comments of the 10 panelists.

[0083] [Table 4]

[0084] As shown in Table 4, it was confirmed that adding a composition containing palmitoleic acid (Product 4-1 of the present invention) to food and beverages as an unpleasant flavor improving composition can improve the unpleasant flavor of those foods and beverages.

[0085] [Example 5] Confirmation of effect on improving unpleasant flavor 5: Vitamin-containing food and beverages A commercially available vitamin drink was prepared (hereinafter referred to as the basic vitamin drink). The main vitamins contained in the basic vitamin drink were vitamin A, vitamin B1, vitamin B6, vitamin C, and vitamin D (the concentration of vitamin B1 was approximately 0.2%).

[0086] Furthermore, commercially available palmitoleic acid (99% purity) was prepared and used as an unpleasant flavor improving composition according to one embodiment of the present invention (Product 5-1 of the present invention).

[0087] Next, product 5-1 of the present invention was added to the basic vitamin beverage so that the palmitoleic acid concentration was 100 ppm, 20 ppm, 1 ppm, 100 ppb, or 10 ppb to obtain a vitamin beverage according to one embodiment of the consumer goods of the present invention (products 5-2 to 5-6 of the present invention; hereinafter, each will also be referred to as the vitamin beverage of the present invention).

[0088] Next, a sensory evaluation was conducted on the flavor of the vitamin beverage of the present invention. In the sensory evaluation, the basic vitamin beverage was used as control product 5, and the flavors of products 5-2 to 5-6 of the present invention were compared to control product 5 by 10 well-trained panelists with more than 10 years of experience. In the evaluation, the panelists were asked to score the unpleasant flavors of the products of the present invention according to the following criteria, and were also asked to freely comment on the flavors they felt differed from control product 5. (Criteria) Regarding unpleasant flavors compared to the control product. "Significantly improved" = 4 points "Improved" = 3 points "Slightly improved" = 2 points "No improvement was observed" = 1 point "Unpleasant flavors were perceived more strongly" = 0 points

[0089] Table 5 shows the average scores and representative comments of the 10 panelists.

[0090] [Table 5]

[0091] As shown in Table 5, it was confirmed that adding a composition containing palmitoleic acid (product 5-1 of the present invention) to food and beverages as an unpleasant flavor improving composition can improve the unpleasant flavor of those foods and beverages.

[0092] [Example 6] Production example of a composition containing palmitoleic acid and its emulsified formulation As an example of producing an unpleasant flavor-improving composition according to one aspect of the present invention, a composition containing a compound with palmitoleic acid in its molecule (palmitoleic acid-encapsulated compound) was enzymatically treated according to the following procedure to release palmitoleic acid from the compound, thereby obtaining the composition containing palmitoleic acid as the unpleasant flavor-improving composition. As the palmitoleic acid-encapsulated compound, oil extracted from plant seeds, specifically macadamia seed oil, was used.

[0093] (Step 1) Prepare 850g of commercially available macadamia nut oil (oil extracted from macadamia seeds), heat sterilize it at approximately 75°C, and then cool it to around 40°C.

[0094] (Step 2) After cooling, 4g of lipase (Lipase AY "Amano" 30SD, manufactured by Amano Enzyme Co., Ltd.) and 110g of water were added to the macadamia nut oil, and the mixture was enzymatically treated at approximately 40°C for approximately 22 hours. Next, 26g of ordinary salt was added and heat sterilization was performed at approximately 85°C for 15 minutes. Then, 3g of antioxidant (tocopherol) was added, and the mixture was cooled to approximately 70°C and allowed to stand for approximately 1 hour. Next, the separated aqueous layer was discarded to obtain the oil layer. 7g of a filtration aid was added to the obtained oil layer, and the mixture was stirred for 10 minutes. Impurities were removed by suction filtration to obtain 704g of enzymatically treated macadamia nut oil (lipase treated).

[0095] The resulting enzyme-treated macadamia nut oil contains 25% palmitoleic acid and can be used as is as an unpleasant flavor improving composition according to one embodiment of the present invention (Product 6-1 of the present invention).

[0096] Next, a formulation of product 6-1 of the present invention was prepared by the following procedure.

[0097] A mixture of 30 g of decaglyceryl monooleate and 770 g of glycerin was prepared and heated to approximately 90°C to sterilize and dissolve the decaglyceryl monooleate, thereby obtaining mixture 1. Meanwhile, a mixture 2 was obtained by mixing 80 g of vegetable oil with 20 g of product 6-1 of the present invention. Next, mixture 2 was added to mixture 1 while stirring at 2000 rpm using a TK Robomix (manufactured by Primix), and emulsified by stirring at 7000 rpm for 5 minutes. Then, 100 g of water was added and thoroughly mixed, and the mixture was left to stand overnight. After filtration, an unpleasant flavor improving composition (emulsified formulation, average particle size approximately 178 nm) according to one aspect of the present invention was obtained (product 6-2 of the present invention). The palmitoleic acid concentration of product 6-2 of the present invention was 0.5%.

[0098] As another embodiment of the unpleasant flavor improving composition, in order to increase the palmitoleic acid concentration, the 98% pure palmitoleic acid prepared in Example 1 was added to Product 6-1 of the present invention so that the palmitoleic acid concentration became 50%, thereby obtaining the unpleasant flavor improving composition (Product 6-3 of the present invention). Furthermore, in order to prepare an emulsified formulation of Product 6-3 of the present invention, an emulsified formulation of Product 6-3 of the present invention was prepared in the same manner as the preparation method of Product 6-2 of the present invention, except that Product 6-1 of the present invention was replaced with Product 6-3, thereby obtaining an unpleasant flavor improving composition (emulsified formulation, average particle size approximately 180 nm) according to one embodiment of the present invention (Product 6-4 of the present invention). The palmitoleic acid concentration of Product 6-4 of the present invention was 1%. Thus, even with enzyme-treated products, the desired palmitoleic acid concentration can be obtained by enzymatically treating a product to which palmitoleic acid has been appropriately added.

[0099] [Example 7] Confirmation of effect on improving unpleasant flavor 6: Milk-containing food and beverage (3) A commercially available cheese sauce was prepared (hereinafter also referred to as the basic cheese sauce). 4 ppm of Product 6-1 of the present invention (palmitoleic acid concentration 25%), prepared in Example 6, was added to it (resulting in a palmitoleic acid concentration of 1 ppm) to obtain a cheese sauce according to one aspect of the present invention (Product 7-1; hereinafter also referred to as the cheese sauce of the present invention). Furthermore, 4 ppm of Product 6-3 of the present invention (palmitoleic acid concentration 50%), prepared in Example 6, was added to the basic cheese sauce (resulting in a palmitoleic acid concentration of 2 ppm) to obtain a cheese sauce according to another aspect of the present invention (Product 7-2; hereinafter also referred to as the cheese sauce of the present invention).

[0100] Next, a sensory evaluation was conducted on the flavor of the cheese sauce of the present invention. In the sensory evaluation, the basic cheese sauce was used as control product 7, and five well-trained panelists with more than 10 years of experience were asked to freely comment on the flavor of products 7-1 and 7-2 of the present invention compared to control product 7. As a result, all five panelists responded that the unpleasant moldy or sulfurous flavor they had felt when consuming control product 7 was reduced, and that the reduction was particularly significant in the top flavor, indicating an improvement in the unpleasant flavor. Furthermore, all five panelists evaluated that this effect was greater in product 7-2 of the present invention, which contains product 6-2 with a higher palmitoleic acid concentration, than in product 7-1 of the present invention.

[0101] [Example 8] Confirmation of effect on improving unpleasant flavor 7: Addition of emulsifying agent to food and beverages of Examples 1-5 Various food and beverage products according to one embodiment of the present invention were obtained by adding Product 6-2 of the present invention (an emulsifying preparation containing 0.5% palmitoleic acid), prepared in Example 6, to the basic soy milk beverage prepared in Example 1, the basic yogurt prepared in Example 2, the basic milk protein beverage prepared in Example 3, the basic black vinegar beverage prepared in Example 4, and the basic vitamin beverage prepared in Example 5, as shown in Table 6 below.

[0102] Next, sensory evaluations were conducted on the flavors of the various food and beverage products of the present invention. In the sensory evaluations, ten well-trained panelists with 12 or more years of experience were asked to evaluate the flavors of the present invention products 8-1 to 8-6 compared to a basic soy milk beverage (control product 8-1), the flavors of the present invention products 8-7 to 8-11 compared to a basic yogurt (control product 8-2), the flavors of the present invention products 8-12 to 8-15 compared to a basic milk protein beverage (control product 8-3), the flavors of the present invention products 8-16 to 8-20 compared to a basic black vinegar beverage (control product 8-4), and the flavors of the present invention products 8-21 to 8-25 compared to a basic vitamin beverage (control product 8-5). (Criteria) Regarding unpleasant flavors compared to the control product. "Significantly improved" = 4 points "Improved" = 3 points "Slightly improved" = 2 points "No improvement was observed" = 1 point "Unpleasant flavors were perceived more strongly" = 0 points

[0103] Table 6 shows the average scores and representative comments of the 10 panelists.

[0104] [Table 6]

[0105] As shown in Table 6, it has been confirmed that adding a composition containing palmitoleic acid (Product 6-2 of the present invention, an emulsifying agent) to various foods and beverages as a composition for improving unpleasant flavors can improve the unpleasant flavors of those foods and beverages. Furthermore, it is thought that if Product 6-4 of the present invention (an emulsifying agent with a higher palmitoleic acid concentration than Product 6-2) is used instead of Product 6-2, the amount of emulsifying agent added can be reduced compared to Product 6-2.

[0106] [Example 9] Confirmation of effect on improving unpleasant flavor 8: Legume-containing food 2 Soy meat hamburgers were prepared using the ingredients shown in Table 7 below, following the procedure described below.

[0107] [Table 7]

[0108] First, ingredients 3-6 (salt, refined sugar, L-sodium glutamate) were dissolved in ingredient 2 (hot water), and beef flavor 1 (water-soluble, manufactured by Hasegawa Fragrances Co., Ltd.) was added to obtain a flavoring solution, into which ingredient 1 (granular soy protein) was quickly immersed. Ingredient 7 (modified starch) was then added and kneaded until uniform to obtain mixture 1. Next, ingredient 9 (powdered soy protein) and ingredient 10 (methylcellulose) were dispersed in ingredient 11 (rice salad oil 1) to obtain a paste, and ingredient 8 (cold water, ice water is fine) was added to it, then stirred with a hand mixer to create a curd, obtaining mixture 2. Finally, after thoroughly mixing mixture 1 and mixture 2, ingredient 12 (rice salad oil 2) and beef flavor 2 (oil-soluble, manufactured by Hasegawa Fragrances Co., Ltd.) were added to prepare mixture 3. Approximately 100g of the resulting mixture 3 was taken, shaped, steamed in a steam oven (120°C, 10 minutes), and then grilled on a hot plate to obtain a basic soy meat hamburger.

[0109] On the other hand, a soy meat hamburger according to one aspect of the present invention was obtained in the same manner as the basic hamburger, except that the commercially available palmitoleic acid (purity 98%, product 1-1 of the present invention) prepared in Example 1 was added together with beef flavor 2 at concentrations of 1000 ppm, 100 ppm, 10 ppm, or 1 ppm during the preparation of the basic hamburger (products 9-1 to 9-4 of the present invention).

[0110] Next, a sensory evaluation was conducted on the flavor of the soy meat hamburger of the present invention. In the sensory evaluation, the basic soy meat hamburger was used as control product 9, and the flavors of products 9-1 to 9-4 of the present invention were evaluated by 10 well-trained panelists with 12 or more years of experience, compared to control product 9. In the evaluation, the panelists were asked to score the unpleasant flavors of the products of the present invention according to the following criteria, and were also asked to freely comment on the flavors they felt differed from control product 9. (Criteria) Regarding unpleasant flavors compared to the control product. "Significantly improved" = 4 points "Improved" = 3 points "Slightly improved" = 2 points "No improvement was observed" = 1 point "Unpleasant flavors were perceived more strongly" = 0 points

[0111] Table 8 shows the average scores and representative comments of the 10 panelists.

[0112] [Table 8]

[0113] As shown in Table 6, it was confirmed that adding a composition containing palmitoleic acid (Product 1-1 of the present invention) to food and beverages as a composition for improving unpleasant flavors can improve those foods and beverages.

[0114] [Example 10] Confirmation of effect on improving unpleasant flavor 9: Other food and beverages The commercially available palmitoleic acid (purity 98%, product 1-1 of the present invention) prepared in Example 1 was added to the commercially available food and beverages shown in Table 9 below to obtain various food and beverages according to one embodiment of the present invention (products 10-1 to 10-8 of the present invention).

[0115] Next, a sensory evaluation was conducted on the flavor of the food and beverage products of the present invention. In the sensory evaluation, commercially available food and beverage products were used as control products as shown in Table 9 below, and five well-trained panelists with more than 10 years of experience were asked to freely comment on the reduced unpleasant flavor of the product of the present invention compared to each control product. Representative comments are shown in Table 9.

[0116] [Table 9]

[0117] As shown in Table 9, it was confirmed that adding a composition containing palmitoleic acid (Product 1-1 of the present invention) to various foods and beverages as a composition for improving unpleasant flavors can improve those foods and beverages.

[0118] Furthermore, although Table 9 only shows examples at 1 ppm, we confirmed that when palmitoleic acid is added to these commercially available foods and beverages at concentrations ranging from 1 ppb to 10 ppm, the above-mentioned effect of improving unpleasant flavors is achieved.

Claims

1. A method for improving unpleasant flavors perceived from food and beverages containing legumes, vinegar, grains, almonds, vitamins, or milk, comprising the following steps 1 to 3. (Step 1) Process to prepare macadamia seed oil (Step 2) A step to obtain a lipase-treated product containing palmitoleic acid by lipase treatment of the oil extracted from the macadamia seeds prepared in Step 1. (Step 3) Adding the lipase-treated product obtained in Step 2 to a food or beverage containing legumes, a food or beverage containing vinegar, a food or beverage containing grains, a food or beverage containing almonds, a food or beverage containing vitamins, or a food or beverage containing milk, as an unpleasant flavor improving composition containing palmitoleic acid as an active ingredient.

2. The method for improving an unpleasant flavor according to claim 1, further comprising a step of emulsifying the lipase-treated product between step 2 and step 3.

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