JP2021171023A - Agent for masking unpleasant taste of food or drink containing rotundone as active ingredient - Google Patents

Abstract

To provide a masking agent that reduces any taste that is derived from food or drink but is undesirable in product design and can improve the taste into a generally desirable taste that the food or drink originally possess; and further provide a masking agent that has many advantages like: the masking agent does not give unnecessary fragrance or flavor in actual concentration when added to food or drink, so that the masking agent can be used to various foods and drinks with high versatility; the masking agent proves high safety because the masking agent has been eaten for a long time; and the masking agent is made from inexpensive general materials easily available, achieving a high cost performance.SOLUTION: The inventors have discovered that adding rotundone to food or drink makes it possible to mask an undesirable taste of the food or drink and improve their flavor without giving unnecessary fragrance or flavor to them.SELECTED DRAWING: None

Description

The present invention relates to a masking agent. More specifically, a masking agent for foods and drinks containing rotundone as an active ingredient, and a method for masking the unpleasant taste of foods and drinks using the masking agent, particularly, a masking agent for the aftertaste of acidity, bitterness, and high-sweetness sweeteners, and The present invention relates to a method of masking the unpleasant taste of food and drink using the masking agent.

The tastes are mainly sweet, salty, sour, umami, and bitter, as well as astringent, harsh, and pungent. When these tastes are present in a moderate amount in the food and drink, they give a good flavor to the food and drink, but when they are present in excess, they bring an unpleasant taste to the food and drink.

Foods and drinks with a bitter taste include, for example, fruits such as grapefruit containing naringin, which is a bitter taste substance, vegetables such as bitter melon, roasted extracts such as coffee, and chemical substances such as flavor substances and peptides. It is known that protein hydrolysates and the like have a bitter taste. The reduction of bitterness in the case of grapefruit juice-containing beverages and coffee is usually dealt with by adding various sweeteners.

In foods and drinks, a refreshing acidity may be a preferred taste, but an acidity with a peculiar stimulus that pierces the tongue is not always preferable. For example, foods and drinks containing vinegar such as dressings, mayonnaise, and Vermont drinks are characterized by their acidity, but the unique irritation caused by vinegar is not always preferred by everyone, and some people dislike it. Not a few. In addition, fermented foods and drinks such as yogurt, fermented milk, and lactic acid bacteria beverages may be preferred to have a certain degree of acidity, but if the acidity or odor is excessively increased, the taste of consumers is reduced. Further, the acidulant is not intended to impart acidity, but may be used as a pH adjuster for the purpose of improving shelf life, in which case the acidity and acid odor are not desirable for food and drink.

In recent years, the number of foods and drinks using low-calorie, high-sweetness sweeteners is increasing due to excessive intake of sugar, concerns about lifestyle-related diseases associated therewith, and heightened health consciousness. These high-intensity sweeteners have the excellent performance of having hundreds of times the sweetness of sugars, which are commonly used sweeteners such as sucrose, fructose, and glucose, but they are unnatural with a trailing trail. It often has a mild sweetness, an unpleasant aftertaste, a bitter taste, and an astringent taste. As a result, the quality of taste is inferior to that of sucrose, fructose, glucose and the like. Therefore, in order to use a high-sweetness sweetener, improvement of its drawbacks is the biggest issue.

Fragrance compounds are compounds that stimulate the sense of smell, and it is said that there are tens of thousands of types. On the other hand, the flavor of food and drink is considered to be a sensation in which olfactory stimuli and taste stimuli are integrated in the brain. That is, the olfactory stimulus is combined with a compound that stimulates the taste (salt, sugar, monosodium glutamate, etc.) to form the flavor of the whole food and drink. Therefore, in recent years, among compounds having aroma, a search for a compound that stimulates the sense of taste as well as the sense of smell has become active, and it is used for improving the overall flavor of foods and drinks.

As an example of using a fragrance as the above-mentioned unpleasant taste masking method, a method of adding mint essential oil, coconut essential oil and eucalyptus essential oil as a bittersweet taste masking method of high cacao chocolate (Patent Document 1), citrus fruits, coffee, tea, cacao And as a method of suppressing the bitterness derived from hops, a method of adding isobutyl angelate (Patent Document 2), an acid taste and / or acid odor suppressant consisting of isothiocyanates (Patent Document 3), 4, 7- Bitter and / or astringent taste inhibitor consisting of tridecazienal and / or 2,4,7-tridecatrienal (Patent Document 4), 4,7-tridecagenal and / or 2,4,7-tride There are acid taste and / or acid odor suppressors made of catrienal (Patent Document 5) and the like.

Further, as a taste improving agent for a high sweetness sweetener, for example, a taste improving agent for a high sweetness sweetener, which comprises spirantol or an extract or essential oil of a plant containing spirantol (Patent Document 6). , High-sweetness sweeteners, and liqueur-based flavors of 0.1 parts by mass or more per 1 part by mass of the high-sweetness sweetener, such as plum liquor, apricot liquor, amarette, apricot brandy, or cherry brandy. Beverages characterized by containing (Patent Document 7), high-sweetness sweeteners and yogurt fragrances selected from aspartame and / or assesulfam potassium, peach fragrances, grapefruit fragrances, apple fragrances, acerola fragrances, ume fragrances, umesh fragrances, Isosorbide preparation with improved taste (Patent Document 8), which comprises one or more fragrances selected from coffee fragrances and tea fragrances, preferably yogurt fragrances (Patent Document 8), 0.0001 to 0. 06 wt% sclarose, 0.0002-0.07 wt% Stevia extract with a weight ratio of stebioside to rebaudioside of 1: 0.5-2 Stevia extract, collagen peptide, 0. Collagen-containing foods and drinks with improved taste by containing 4-5% by weight of Vitamin C, 0.0002-0.08% by weight of Acesulfam potassium, and 0.01-1.0% by weight of peach fragrance (Patent) Document 9), as an active ingredient for improving the taste of a high-sweetness sweetener, comprises ginger extract and one or more selected from caraway essential oil, peppermint tail essential oil, cardamon essential oil and nutmeg extract. High sweetness sweetener taste improver (Patent Document 10), High sweetness sweetener taste improver (Patent Document 11) consisting of 4,7-tridecadienal, resistant dextrin and lemon flavor And a citrus flavor containing a lime flavor and a high sweetness sweetener, the content of the indigestible dextrin is 13.5 g / L or less, and the content of the citrus flavor with respect to the content of the indigestible dextrin. A beverage in which the weight ratio of the content is 0.022 or more, and the weight ratio of the content of the resistant dextrin to the amount obtained by converting the content of the high sweetness sweetener into sucrose is 0.14 or more ( Patent Document 12), (a) at least one sweetener selected from the group of isomerized sugars, sugars, sclarose and stevia extracts, and (b) cis-3-hexenol, trans-2-hexenal, tr. A carbonated beverage (Patent Document 13) characterized by containing an aroma component having a scent of green leaves, which is at least one selected from the group of ans-2-hexenol and cis-2-hexenol, and a high content containing davana oil. A taste improver for sweetness sweeteners (Patent Document 14), a taste improver for high sweetness sweeteners containing ginger extract (Patent Document 15), and a high sweetness sweetener containing isobutyl angelate as an active ingredient. (Patent Document 16) and the like.

Rotundone is useful for perfume applications and has been reported to be the causative component of spicy, pepper-like aromas in Shiraz wines characterized by spicy, pepper-like aromas and grapes for those wines. It has also been reported that black pepper and white pepper contain several ppm and are important aroma components, and that they are also contained in trace amounts in spices such as marjoram, oregano, rosemary, basil, and thyme. (Non-Patent Document 1). Further, it is known to be used as a citrus flavor enhancer (Patent Document 17) and a fruit flavor enhancer (Patent Document 18). However, although rotundone is known to be used as a flavor, the effect of masking the unpleasant taste of food and drink by adding it to food and drink has not been known at all.

Japanese Patent No. 6230141 Japanese Patent No. 6296473 Japanese Unexamined Patent Publication No. 2012-34603 Japanese Unexamined Patent Publication No. 2013-143930 Japanese Unexamined Patent Publication No. 2013-21926 Japanese Patent No. 4688517 Japanese Unexamined Patent Publication No. 2007-82491 Japanese Unexamined Patent Publication No. 2006-131625 Japanese Patent No. 4630787 Japanese Patent No. 5231356 Japanese Patent No. 4906147 Japanese Patent No. 5657823 Japanese Unexamined Patent Publication No. 2015-6167 Japanese Unexamined Patent Publication No. 2011-24428 Japanese Unexamined Patent Publication No. 2011-30535 Japanese Patent No. 6281926 Japanese Unexamined Patent Publication No. 2016-198025 Japanese Unexamined Patent Publication No. 2016-198026

Journal of Agricultural and Food Chemistry, 2008, Vol. 56, No. 10, p3738-3744

An object of the present invention is to reduce the unpleasant tastes of foods and drinks when they are unpleasant in product design, and to reduce the unpleasant tastes of the foods and drinks, and to reduce the unpleasant tastes of the foods and drinks. It is to provide a masking agent that can be improved.

Furthermore, since it is difficult to feel the aroma and flavor at the concentration actually added to food and drink, it is highly versatile and can be used for various food and drink, high safety backed by abundant eating experience, and easy on a daily basis. It is to provide a masking agent that combines many of the advantages of high cost performance that can be achieved with inexpensive raw materials available.

As a result of diligent research to solve the above problems, the present inventors have added rotandon to foods and drinks without imparting unnecessary flavors and flavors to these foods and drinks. It has been found that the unpleasant taste of foods and drinks, particularly the unpleasant tastes derived from the aftertaste of acidity, bitterness and high sweetness sweeteners can be reduced and the flavor of foods and drinks can be improved, and the present invention has been completed.

Thus, the present invention provides the following:
(1) Rotundone [(3S, 5R, 8S) -5-isopropenyl-3,8-dimethyl-3,4,5,6,7,8-hexahydro-1 (2H) -azulenone and / or (3R, 5R, 8S) -5-isopropenyl-3,8-dimethyl-3,4,5,6,7,8-hexahydro-1 (2H) -azulenone], a masking agent for the unpleasant taste of food and drink.
(2) The masking agent according to (1), wherein the unpleasant taste is acidity.
(3) The masking agent according to (1), which has a bitter taste as an unpleasant taste.
(4) The masking agent according to (1), wherein the unpleasant taste is the aftertaste of a high-sweetness sweetener.
(5) A masking composition containing 0.1 ppt to 1 ppm of the masking agent according to any one of (1) to (4) to improve the unpleasant taste of food and drink.
(6) A method for masking the unpleasant taste of foods and drinks, wherein the masking agent according to any one of (1) to (4) is contained in foods and drinks at 0.001 ppt to 1 ppb.

According to the present invention, although it is a flavor possessed by a food or drink, when there is an unpleasant unpleasant taste in the product design, those unpleasant tastes are reduced, and the overall preferable flavor originally possessed by the food or drink is obtained. Can be improved. In addition, it has many advantages such as high versatility that can be used for various foods and drinks, high safety backed by abundant eating experience, and high cost performance that can be achieved with inexpensive raw materials that can be easily obtained on a daily basis. A masking agent can be provided.

Hereinafter, the present invention will be described in more detail.

In the present invention, the values of%, ppm, ppb, and ppt indicate the values of mass vs. mass, respectively, unless otherwise specified.

The food or drink having an sour taste in the present invention means a food or drink having an sour taste when taken orally, and although the sour taste is not originally required, the food or drink having an sour taste due to the addition of an acidulant or the like for the purpose of preservation or the like. Including goods. When ingested or used, it may be in any form of liquid, solid or semi-solid. Such foods and drinks contain natural materials such as various natural fruits, or natural or synthetic acidulants such as citric acid, tartaric acid, malic acid, fumaric acid, lactic acid, acetic acid, adipic acid, succinic acid and phosphoric acid. Examples include beverages, yogurt, dressings, mayonnaise, sauces, pickles, seasonings, instant foods, bread, malic acid, tofu and the like.

The food or drink having a bitter taste in the present invention means a food or drink having a bitter taste when taken orally, and although the bitter taste is not originally required, the food or drink having a bitter taste as a result of being added for other purposes or the like. Including food and drink that has become. In addition, when ingested or used, it may be in any form of liquid, solid or semi-solid. Examples of the bitterness substance include potassium chloride, bitterness peptide, naringin, caffeine, nicotine, phenylthiourea, picric acid, magnesium sulfate, brucine, urea, quinine and the like. Final products containing substances with a bitter taste include foods and drinks such as tea, coffee, cocoa, grapefruit, and beer, compound feeds for broiler fattening, pet foods, bitter stomach medicines, medicines such as energy drinks, and mouth refreshers. Quasi-drugs can be mentioned. Further, the unpleasant taste of protein, the unpleasant taste of peptide, the unpleasant taste of gelatin, and the unpleasant taste of amino acid can be mentioned.

In the present invention, the high-intensity sweetener is a sweetener having a sweetness hundreds to thousands times higher than that of sucrose, and is sucralose, aspartame, acesulfam potassium, saccharin, sodium saccharin, stevia extract, rebaudioside A. , Neotheme, Ariteme, Monatin, Taumatin, Saccharin extract (Glycyrrhizin), Luo Han Guo extract (Mogroside) and Sweet tea extract (Philozlutin), which may be used alone or in combination. It may be. The taste improver of the present invention can be used without being limited to the type of high-sweetness sweetener, but is particularly preferably used for sucralose, aspartame, acesulfame potassium, and stevia extract.

In the present invention, improving the aftertaste of a high-sweetness sweetener or masking the unpleasant aftertaste means an unnatural sweetness, an unpleasant aftertaste or bitterness, or an astringent taste that is characteristic of the high-sweetness sweetener. It means to suppress these dislikes, give a sharp and refreshing feeling, and improve to a natural sweetness close to that of sugar.

Rotundone generally refers to (3S, 5R, 8S) -5-isopropenyl-3,8-dimethyl-3,4,5,6,7,8-hexahydro-1 (2H) -azulenone. However, when referred to as "rotundone" in the present specification, it is an isomer of this, (3R, 5R, 8S) -5-isopropenyl-3,8-dimethyl-3,4,5,6,7, Also includes 8-hexahydro-1 (2H) -azulenone.

The active ingredient of the present invention (3S, 5R, 8S) -5-isopropenyl-3,8-dimethyl-3,4,5,6,7,8-hexahydro-1 (2H) -azulenone (hereinafter (-) )-Rotundone) can be synthesized by the method described in Non-Patent Document 1 or obtained from a commercially available pepper essential oil by a fractionation method in which a distillation method or a chromatographic method is used alone or in combination.

In addition, the active ingredient of the present invention (3R, 5R, 8S) -5-isopropenyl-3,8-dimethyl-3,4,5,6,7,8-hexahydro-1 (2H) -azulenone (hereinafter 3-Epirotandon) can be synthesized by the method described in JP-A-2017-206451.

The (-)-rotundone and 3-epirotundone of the present invention can have a masking effect on the unpleasant taste of foods and drinks by adding them to foods and drinks individually or as a mixture, respectively.

For foods and drinks, for example, foods and drinks having an unpleasant taste derived from the aftertaste of acidity, bitterness, and high-sweetness sweeteners, these foods and drinks are prepared by adding rotundone, which is a compound of the present invention, to the foods and drinks as they are. It is possible to mask the unpleasant taste of foods and drinks and improve the flavor of foods and drinks without imparting unnecessary aromas and flavors to the food and drink. Further, (-)-rotundone and 3-epirotundone of the present invention can be mixed and used in an arbitrary ratio. Therefore, in the following, (-)-rotundone alone, 3-epirotundone alone and a mixture of (-)-rotundone and 3-epirotundone are simply referred to as "rotundone".

The blending amount of rotandon of the present invention varies depending on the purpose or the type of food or drink, but the lower limit value with respect to the total mass of food or drink is 0.001 ppt, 0.002 ppt, 0.005 ppt, 0.01 ppt, 0.02 ppt, 0.05 ppt, 0.1 ppt, 0.2 ppt can be exemplified, and 1 ppb, 0.5 ppb, 0.2 ppb, 0.1 ppb, 50 ppt, 20 ppt, 10 ppt, and 5 ppt can be exemplified as the upper limit values. Any combination of lower and upper limits can be mentioned. For example, 0.001 ppt to 1 pppb, preferably 0.005 ppt to 0.5 pppb, more preferably 0.01 ppt to 0.1 pppb, more preferably 0.05 ppt to 50 ppt, and particularly preferably 0, based on the total weight of the food or drink. The range of 1 ppt to 10 ppt can be exemplified. Within these ranges, it has an excellent effect of masking unpleasant taste for food and drink.

The masking agent of the present invention can be added to foods and drinks alone, but can also be used as a masking composition for foods and drinks in combination with a flavor component. Examples of other fragrance components that can be contained together with the masking agent of the present invention include various synthetic fragrances, natural fragrances, natural essential oils, and plant extracts. For example, natural essential oils, natural fragrances, and synthetic fragrances described in "Patent Office, Well-known Conventional Technology Collection (Fragrances) Part II Food Fragrances" or "Synthetic Fragrances, Chemistry and Product Knowledge, Augmented New Edition, The Chemical Daily" Can be mentioned.

As these components, as materials for food fragrances, for example, hydrocarbons such as limonene, milsen, α-pinene, β-pinene, α-terpinene, γ-terpinene, cariophyllene; hexanol, heptanol, octanol, nonanol, decanol. , Cis-3-hexenol, cis-6-nonenol, cis, cis-3,6-nonazienol, citronerol, geraniol, nerol, linalol, α-terpineol, γ-terpineol, terpinene-4-ol, menthol, timol, eugenol Alcohols such as: hexanal, cis-3-hexenal, trans-2-hexenal, heptanal, octanal, nonanal, decanal, undecanal, 10-undecenal, 2,6-nonazienal, citral, terpinene, vanillin, ethyl vanillin, etc. Araldehydes and their acetals; carboxylics, pregons, mentones, camphors, nutcatons, acetoins, diacetyls, 2-heptanones, 2-octanones, 2-nonanones, 2-undecanones, p-methylacetophenones, p-methoxyacetophenones, raspberry ketones, Ketones such as anisylacetone, disulfide, acetylfuran, maltor, ethylmaltor, cycloten, dimethylhydroxyfuranone and their ketals; ethyl acetate, propyl acetate, butyl acetate, isoamyl acetate, hexyl acetate, heptyl acetate, geranyl acetate, Linalyl acetate, ethyl propionate, isoamyl propionate, hexyl propionate, geranyl propionate, citronellyl propionate, ethyl butyrate, isoamyl butyrate, geranyl butyrate, butylpentanoate, methyl butyrate, Esters such as methylanthranilate; fatty acids such as acetic acid, propionic acid, butyric acid, isobutyric acid, disulfide acid, isovaleric acid, caproic acid; Ethers; sulfur-containing compounds such as thiazole, propyl mercaptane, allyl mercaptane, furfuryl mercaptane, dimethyl sulfide, dimethyl disulfide, diallyl sulfide, diallyl disulfide, methional, furfuryl disulfide; and the like.

These synthetic fragrances are readily available on the market and can be easily synthesized if desired.

In addition, various extracts include herbs / spice extracts, coffee / green tea / black tea / oolong tea extracts, milk or processed dairy products, and enzymatic decomposition products such as lipases / proteases thereof.

The masking agent or masking composition of the present invention can be used as it is by adding it to foods and drinks, but it can also be added to foods and drinks as a solution, emulsified preparation, powder preparation or the like dissolved in a water-miscible organic solvent. ..

Examples of the water-miscible organic solvent for dissolving the masking agent or the masking agent composition of the present invention include ethanol, methanol, acetone, tetrahydrofuran, acetonitrile, methyl ethyl ketone, 2-propanol, glycerin, propylene glycol and the like. Can be done. Of these, ethanol, glycerin or propylene glycol is particularly preferable from the viewpoint of use in foods and drinks.

Further, in order to prepare an emulsified preparation, the masking agent or masking agent composition of the present invention can be obtained by emulsifying with an emulsifier. For example, one or more emulsifiers or stabilizers such as Kiraya extract, enzyme-treated lecithin, sucrose fatty acid ester, polyglycerin fatty acid ester, glycerin fatty acid ester, and arabic gum may be blended, for example, homomixer, colloid mill, high pressure. It can also be in the form of an emulsified fragrance preparation by emulsifying with a homogenizer or the like. The amount of the emulsifier or stabilizer used varies depending on the type of emulsifier or stabilizer, and is, for example, in the range of 0.1 to 25% by mass, preferably in the range of 5 to 20% by mass, based on the mass of the emulsified fragrance preparation. Can be mentioned.

Further, for example, sugar, lactose, glucose, trehalose, cellobiose, water candy, reduced water candy and other sugars; sugar alcohols; various starch decomposition products such as dextrin and starch derivatives, starch, gelatin, arabic gum and the like are added to the emulsified fragrance preparation. After appropriately blending an excipient such as natural gum, it can be dried by an appropriate drying means such as spray drying or vacuum drying to form a powdered fragrance preparation. The blending amount of these excipients can be appropriately selected depending on the properties desired for the powdered flavor preparation and the like.

The masking agent or masking agent composition of the present invention can mask the unpleasant taste of food and drink by adding it to the food and drink having an unpleasant taste.

Examples of foods and drinks having such an unpleasant taste include drinks such as coffee, fruit juice drinks, and acidic drinks as foods and drinks having an acid taste; vinegars such as acetic acid, black vinegar, apple vinegar, and brewed vinegar, and vinegars using these vinegars. Beverages: yogurt, dressings, mayonnaise, sauces, dried plums, pickles, seasonings, instant foods, bread, vinegar, tofu, citrus and the like.

Foods and drinks with a bitter taste include foods and drinks such as green tea, tea, coffee, cocoa, grapefruit, beer, beer-taste beverages, protein beverages, amino acid beverages, tomatoes, peppers, celery, uri, bitter melon, carrots, potatoes, alparagus, Examples include vegetables such as warabi and zenmai, vegetable-based beverages containing these vegetables, feeds, pet foods, bitter stomachic medicines, medicines such as nutritional drinks, and non-medicinal products such as mouth refreshers.

Foods and drinks to which sweetness is imparted by a high-sweetness sweetener include, for example, fruit juice, fruit juice containing fruit grains, fruit beverage, fruit juice beverage, fruit juice-containing beverage, vegetable juice, vegetable-containing juice, and fruit-vegetable mix. Fruit juice or vegetable juice beverages such as juice; carbonated beverages such as cola, ginger ale, and cider; soft beverages such as sports drinks and near water; tea-based or palatable beverages such as coffee, cocoa, tea, matcha, green tea, and oolong tea; General beverages such as dairy beverages, dairy coffee, cafe ole, milk tea, matcha milk, fruit dairy beverages, drink yogurt, lactic acid bacterium beverages and other dairy-containing beverages; yogurt, jelly, drink jelly, pudding, bavarois, Desserts such as Bramanger and mousse; Ice creams such as ice cream, ice milk, and lacto ice; Cold confectionery such as sherbet and ice confectionery; Kind; Rice confectionery, snacks; General sugar confectionery such as chewing gum, hard candy, nouga candy, jelly; Sauces including fruit flavor sauce and chocolate sauce; Creams such as butter cream, flower paste and whipped cream; Strawberry jam and marmalade Jam such as; Bread containing sweet bread, etc .; General seasonings such as sauce, tomato ketchup, sauce, noodle soup used for grilled meat, grilled chicken, eel, etc .; Sweetening composition such as stick sugar; Can be broadly exemplified as processed agricultural, livestock and fishery products including processed meat products such as, retort foods, pickles, boiled foods, delicacies, prepared foods, and frozen foods.

Moreover, the masking agent or the masking agent composition of the present invention may be used in combination with various other known and commercially available additives.

The content of the rotundone of the present invention in the masking composition varies depending on the purpose or the type of the masking composition, but the lower limit values with respect to the total mass of the masking composition are 0.1 ppt, 0.2 ppt, and so on. 0.5 ppt, 1 ppt, 2 ppt, 5 ppt, 10 ppt, 20 ppt can be exemplified, and the upper limit values can be 1 ppm, 0.5 ppm, 0.2 ppm, 0.1 ppm, 50 pppb, 20 pppb, 10 pppb, 5 pppb, and these lower limits and 5 pppb can be exemplified. Any combination of upper limits can be mentioned. In particular, 0.1 ppt to 1 ppm (in the present specification, "-" means a range including the upper limit value and the lower limit value), preferably 0.5 ppt to 0.5 ppm, more preferably 1 ppt to 0.1 ppm, and more. The range of preferably 5 ppt to 50 pppb, particularly preferably 10 ppt to 10 pppb can be exemplified. Within these ranges, it has an excellent effect of masking the unpleasant taste of food and drink.

Hereinafter, the present invention will be described in more detail with reference to Examples. The present invention is not limited to these.

The (-)-rotundone in the present invention was synthesized according to the method described in Non-Patent Document 1. Further, 3-epirotandone in the present invention was synthesized according to the method described in JP-A-2017-206451.

Example 1: Masking effect of sour taste A candy was prepared by a conventional method by mixing at the ratio shown in the formulation shown in Table 1 (Comparative Product 1).

(-)-Rotundone or 3-epirotundone was added to the formulations shown in Table 1 to the concentrations shown in Table 2, and candies were prepared in the same manner as in Comparative Product 1. A sensory evaluation of acidity masking was performed by tasting each candy by 10 well-trained panelists.

The score of the acidity masking is 0: no difference from the control, 1: the acidity is slightly suppressed compared to the control, 2: the acidity is suppressed compared to the control, 3: control, with the comparative product 1 as the control. Compared with the control, the acidity was strongly suppressed and the sourness of citric acid was less likely to be felt. 4: Compared with the control, the acidity was completely suppressed and the sourness of citric acid was not felt. Table 2 shows the average score of the 10 panelists.

As shown in Table 2, when (-)-rotundone or 3-epirotundone was added alone to the candy formulation, the candy was masked in acidity as compared to Comparative Product 1. Further, it was confirmed that the acidity was masked in the range of 0.001 ppt to 1 ppb as the concentration based on the mass. However, at an added concentration of 10 ppb, the acidity was masked, but the spicy aroma characteristic of rotundone was exhibited, resulting in a lack of taste balance.

Reference Example 1: Preparation of Lemon Essence 1991.6 g of commercially available lemon essential oil was subjected to a thin film distillation treatment using a molecular distillation apparatus to obtain 1857.3 g of a distillate and 122.5 g of a residue. The residue was again subjected to thin film distillation under the same conditions to obtain 64.7 g of distillate and 58.4 g of residue. A total of 1922.0 g of the distillate obtained by the thin film distillation treatment is precisely distilled using a sluzer packing-filled distillation column to distill terpene hydrocarbons, whereby 190.1 g of refined lemon essential oil is obtained. Was done. Further, in order to distill the terpene hydrocarbon, precision distillation was performed again using a slewer packing-filled distillation column to distill the terpene hydrocarbon, whereby 106.2 g (reference product 1) of refined lemon essential oil was obtained. rice field. The above reference product 1 was dissolved in 1% in an aqueous solution of 80% ethanol to obtain lemon essence (reference product 2).

Example 2: Masking effect of acidity by masking composition To the above reference product 2, (-)-rotundone or 3-epirotundone was added so as to be 1 pt, 10 pt, 100 ppt, 1 ppb, 10 ppb, 100 ppb, 1 ppm, 10 ppm. A masking composition was prepared. These were diluted with a 0.5% aqueous solution of citric acid so as to be 0.1%, and a sensory evaluation of the acidity masking of each masking composition was carried out using the 0.5% aqueous solution of citric acid as a control product. .. The sensory evaluation was scored by the same method as in Example 1. Table 3 shows the average score of 10 panelists.

As shown in Table 3, when (-)-rotundone or 3-epirotundone was added to Reference product 2 alone, the solution masked the acidity as compared with the control product. Further, as the concentration with respect to the reference product 2, it was confirmed that the acidity was masked within the range of 1 ppt to 1 ppm based on the mass of the reference product 2. However, at an added concentration of 10 ppm, the acidity was masked, but the spicy aroma characteristic of rotundone was exhibited, resulting in an imbalance in taste.

Example 3: Masking effect of unpleasant taste (bitter taste) of protein drink 21 g of commercially available plain protein powder was dissolved in water to make 300 g (Comparative Product 2). A protein beverage was prepared by adding (-)-rotundone or 3-epirotundone to the concentrations shown in Table 4. By tasting each protein beverage by 10 well-trained panelists, a sensory evaluation was performed on the masking of the unpleasant taste derived from the bitter taste produced by the protein beverage.

The score of masking the unpleasant taste derived from protein is 0: no difference from the control, 1: the unpleasant taste is slightly suppressed as compared with the control, and 2: the unpleasant taste is suppressed as compared with the control. 3: The unpleasant taste is considerably suppressed as compared with the control, and the bitterness derived from the protein is well masked. 4: The unpleasant taste is completely suppressed as compared with the control, and the bitterness derived from the protein is well masked. It was scored as yes. Table 4 shows the average score of the 10 panelists.

As shown in Table 4, when (-)-rotundone or 3-epirotundone was added alone to the protein beverage, the protein beverage was masked from the protein-derived unpleasant taste as compared with Comparative Product 2. Further, it was confirmed that the concentration was masked in the range of 0.001 ppt to 1 ppb based on the mass. However, at an added concentration of 10 ppb, the unpleasant taste was masked, but the spicy aroma characteristic of rotundone was exhibited, resulting in a lack of taste balance.

Example 4: Masking effect of unpleasant taste on protein drink 2
To the lemon essence of Reference Product 2 above, 1 ppb of (-)-rotundone or 3-epirotundone was added independently. Lemon essence, in which (-)-rotundone or 3-epirotundone was added independently to Reference Product 2 and Reference Product 2, was added in an amount of 0.1% to the protein beverage (Comparative Product 2) described in Example 3.

When these protein beverages were evaluated by 10 well-trained panelists, all panelists compared (-)-rotandone or 3-epirotandone, respectively, to the protein beverage supplemented with lemon essence in Reference 2. It was evaluated that the protein beverage to which the lemon essence added alone had reduced the bitterness derived from the protein and suppressed the unpleasant taste.

Example 5: Masking the bitter taste of bitter chocolate Commercially available bitter chocolate (comparative product 3) was melted at 55 ° C., and (-)-rotundone or 3-epirotundone was added thereto to the concentrations shown in Table 5. I got a chocolate dough. This was cooled to room temperature to obtain bitter chocolate to which (-)-rotundone or 3-epirotundone was added by a conventional method. A sensory evaluation of bitterness masking was performed by tasting each bitter chocolate by 10 well-trained panelists.

The score of the masking of bitterness is 0: no difference from the control, 1: the bitterness is slightly suppressed compared to the control, 2: the bitterness is suppressed compared to the control, 3: control, with the comparative product 3 as the control. Compared with the control, the bitterness was considerably suppressed and the chocolate-derived bitterness was well masked. 4: Compared with the control, the bitterness was completely suppressed and the chocolate-derived bitterness was well masked. Table 5 shows the average score of the 10 panelists.

As shown in Table 5, when (-)-rotundone or 3-epirotundone was added to bitter chocolate alone, the bitter chocolate was masked from the bitter taste derived from bitter chocolate as compared with the comparative product 3. Further, it was confirmed that the concentration was masked in the range of 0.001 ppt to 1 ppb based on the mass. However, at an added concentration of 10 ppb, the bitter taste was masked, but the spicy aroma characteristic of rotundone was exhibited, resulting in a lack of taste balance.

Example 6: Masking effect on stevia-containing beverages 0.05 g of citric acid, 0.01 g of trisodium citrate, 0.04 g of stevia sweetener (containing 85% α-glucosyl rebaudioside A), lemon flavor (Hasegawa fragrance) After mixing 0.1 g (manufactured by the company), water was added to make the total volume 100 mL, and a stevia-containing beverage was prepared (comparative product 4). To this was added a stevia sweetener-containing beverage in which (-)-rotundone or 3-epirotundone was added at the concentrations shown in Table 6.

These were sensory evaluated using 10 well-trained panelists. In the sensory evaluation, the following two items were evaluated on a 6-point scale, and the average score was calculated. The results are shown in Table 6.
(1) About the bitterness of the aftertaste (hereinafter referred to as "bitterness"): The bitterness is felt very strongly in the aftertaste (1 point), the bitterness is strongly felt in the aftertaste (2 points), and the bitterness is felt in the aftertaste (3 points). Some bitterness is felt in the aftertaste (4 points), slightly bitterness is felt in the aftertaste (5 points), and no bitterness is felt in the aftertaste (6 points).
(2) Disadvantages of sweetness trailing afterwards (hereinafter referred to as "sweetness trailing"): Sweetness trailing is very strong and not preferable sweetness (1 point), sweetness trailing is strong and preferable sweetness Not (2 points), sweetness with a backlash, favorable sweetness is weak (3 points), sweetness with a slight backlash (4 points), sweetness with a slight backlash (5 points), sweetness No backlash is felt, and a strong sweetness is felt (6 points).

From the above sensory evaluation, it was found that the taste defect of the stevia sweetener was improved by adding 0.001 ppt to 1 ppb to the stevia-containing beverage by adding (-)-rotundone or 3-epirotundone. Further, at an added concentration of 10 ppb, the aftertaste of the Stevia sweetener was masked, but the spicy aroma characteristic of rotundone was exhibited, and the evaluation result was that the taste balance was lost.

Example 7: Masking effect on acesulfame K-containing beverage After mixing 0.05 g of citric acid, 0.01 g of trisodium citrate, 0.026 g of acesulfame K, and 0.1 g of lemon flavor (manufactured by Hasegawa Fragrance Co., Ltd.), water is added. In addition, the total volume was adjusted to 100 mL, and an acesulfame K-containing beverage was prepared (Comparative Product 5). Acesulfame K-containing beverage was obtained by adding (-)-rotundone or 3-epirotundone at the concentrations shown in Table 7.

These were sensory evaluated using 10 well-trained panelists. The sensory evaluation was evaluated by the same method as in Example 6, and the average score was calculated. The results are shown in Table 7.

From the above sensory evaluation, it was found that the taste defect of the acesulfame K sweetener was improved by adding 0.001 ppt to 1 ppb to the acesulfame K-containing beverage by adding (-)-rotundone or 3-epirotundone. Further, at an added concentration of 10 ppb, the aftertaste of the acesulfame K sweetener was masked, but the spicy aroma characteristic of rotundone was exhibited, and the taste balance was lost.

Example 8: Masking effect on sucralose-containing beverage After mixing 0.05 g of citric acid, 0.01 g of trisodium citrate, 0.008 g of sucralose, and 0.1 g of lemon flavor (manufactured by Hasegawa Fragrance Co., Ltd.), water is added to the total amount. To 100 mL, a sucralose-containing beverage was prepared (comparative product 6). A sucralose-containing beverage was obtained by adding (-)-rotundone or 3-epirotundone at the concentrations shown in Table 8.

These were sensory evaluated using 10 well-trained panelists. The sensory evaluation was evaluated by the same method as in Example 6, and the average score was calculated. The results are shown in Table 8.

From the above sensory evaluation, it was found that the taste defect of the sucralose sweetener was improved by adding 0.001 ppt to 1 ppb to the sucralose-containing beverage by adding (-)-rotundone or 3-epirotundone. Further, at an added concentration of 10 ppb, the aftertaste of the sucralose sweetener was masked, but the spicy aroma characteristic of rotundone was exhibited, and the evaluation result was that the taste balance was lost.

Example 9: Effect on aspartame-containing beverage After mixing 0.05 g of citric acid, 0.01 g of trisodium citrate, 0.025 g of aspartame, and 0.1 g of lemon flavor (manufactured by Hasegawa Fragrance Co., Ltd.), water is added to make the total amount. An aspartame-containing beverage was prepared with 100 mL (comparative product 7). To this was added (−)-rotundone or 3-epirotundone at the concentrations shown in Table 9 to obtain an aspartame-containing beverage.

These were sensory evaluated using 10 well-trained panelists. The sensory evaluation was evaluated by the same method as in Example 6, and the average score was calculated. The results are shown in Table 9.

From the above sensory evaluation, it was found that the taste defect of the aspartame sweetener was improved by adding 0.001 ppt to 1 ppb to the aspartame-containing beverage by adding (-)-rotundone or 3-epirotundone. Further, at an added concentration of 10 ppb, the aftertaste of the aspartame sweetener was masked, but the spicy aroma characteristic of rotundone was exhibited, and the taste balance was lost.

Example 10: Addition to a commercially available non-fermented non-alcoholic beer-flavored beverage and sensory evaluation In a commercially available non-fermented non-alcoholic beer-flavored beverage (a product labeled with "sweetener (acesulfame K)" as a raw material), (-)- 1 ppt of rotandon was added to the beverage and sensory evaluation was performed using 10 well-trained panelists.

As a result, all 10 panelists added (-)-rotandone to the beverage by adding 1 ppt to a commercially available non-fermented non-alcoholic beer-flavored beverage (the raw material was labeled as "sweetener (acesulfame K)". It was evaluated that the bitterness and sweetness aftertaste derived from the sweetener (acesulfame K) of the product) were improved.

Example 11: Preparation of perfume composition containing rotundone A perfume composition for sports drink (comparative product 8: grapefruit flavor) was prepared according to the formulation of Table 10.

A taste improving agent composition (Product 1 of the present invention) in which 1 ppm of (−)-rotundone was added to Comparative Product 8 was prepared.
Preparation of emulsified fragrance 150 g of the present invention, 91 g of SAIB (shoe cloth diacetate hexaisobutyrate), 8 g of medium-chain saturated fatty acid triglyceride and 1 g of natural vitamin E are mixed and dissolved to obtain a uniform oily material mixture. Obtained. This mixture was added to a mixed solution of 350 g of glycerin, 185 g of gum arabic and 315 g of water, and after pre-stirring and dispersing, T.I. K. Using a homomixer (manufactured by Primix Corporation), emulsification was performed at 5000 rpm for 10 minutes to obtain a uniform emulsion having a particle size of about 0.2 to 0.5 μm (Product 2 of the present invention). Further, a uniform emulsion (comparative product 9) was obtained by the same method using the comparative product 8 as a raw material instead of the product 1 of the present invention.

Example 12: Addition to sports drink and sensory evaluation A sports drink was prepared by the formulation shown in Table 11.

The flavor of each beverage was sensory evaluated by 10 well-trained panelists.
As a result, all 10 panelists evaluated that the sports drink to which the product 2 of the present invention was added was more delicious than the sports drink to which the comparative product 9 was added. In addition, as the average evaluation content, the peculiar bitterness of high-sweetness sweeteners has been improved, the aftertaste of sweetness has also been improved, and a sharp and refreshing feeling is given, and the feeling of smoothness is good and it feels extremely delicious. It was an evaluation.

Claims (6)

A masking agent for the unpleasant taste of food and drink consisting of rotundone. The masking agent according to claim 1, wherein the unpleasant taste is acidity. The masking agent according to claim 1, wherein the unpleasant taste is bitter. The masking agent according to claim 1, wherein the unpleasant taste is the aftertaste of a high-sweetness sweetener. A masking composition containing 0.1 ppt to 1 ppm of the masking agent according to any one of claims 1 to 4 to improve the unpleasant taste of food and drink. A method for masking an unpleasant taste of a food or drink, wherein the masking agent according to any one of claims 1 to 4 is contained in the food or drink in an amount of 0.001 ppt to 1 ppb.