Alcohol feeling improver

Abstract

To provide a novel alcoholic feeling improving agent that improves alcoholic feeling of an object to be added, food and drink with improved alcoholic feeling, and a method of improving alcoholic feeling of food and drink.SOLUTION: An alcoholic feeling improving agent consists of a compound of a group A below, one or more compounds selected from a group B, and one or more compounds selected from a group C: (Group A) 2-(3-benzyloxypropyl)pyridine; (Group B) 4-menthyloxy-2-butanone, 2-methyl-4-menthyloxy-2-butanol; and (Group C) 3-(4-ethoxyphenyl)prop-2-enal, 3-(4-propoxyphenyl)prop-2-enal, 3-(4-isopropoxyphenyl)prop-2-enal, etc.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to an alcohol feeling improver, an alcohol feeling improving composition, a food or drink, and a method for improving the alcohol feeling of a food or drink.

Background Art

[0002] While alcoholic beverages are loved by many people as typical luxury goods, for people who cannot consume alcohol, such as automobile drivers, and for people who refrain from alcohol consumption due to recent health consciousness, non-alcoholic beverages (for example, beverages with an alcohol content of 0.00% or beverages with an alcohol content of less than 1%).) and low-alcohol beverages (for example, beverages with an alcohol content of 0.5% to 1%, beverages with an alcohol content of 1% to 3%, beverages with an alcohol content of 1% to 5%, or beverages with an alcohol content of 7% or less.) are in increasing demand, forming a large market.

[0003] However, since non-alcoholic beverages and low-alcohol beverages have a lower ethanol concentration than alcoholic beverages, in addition to the action of ethanol, the stimulating sensation, flavor, that is, the alcohol feeling derived from ethanol may be insufficient and unsatisfactory.

[0004] Therefore, there is an increasing demand for beverages that are non-alcoholic or low-alcoholic but have an imparted or enhanced alcohol feeling, and there is a strong demand for the development of technologies for imparting or enhancing the alcohol feeling with materials other than ethanol.

[0005] For example, Patent Document 1 describes a non-alcoholic beverage containing a pungency-imparting component and a bitterness-imparting component and having an alcohol-like sensation, and a method for imparting an alcohol-like sensation to a non-alcoholic beverage including adding a pungency-imparting component and a bitterness-imparting component to the beverage. Further, Patent Document 2 describes a non-alcoholic beverage characterized in that the content of 2-(methylthio)ethanol, 3-(methylthio)propyl acetate or 3-(methylthio)propionic acid is 10 ppb or more, and a method for imparting an alcohol-like sensation to a non-alcoholic beverage including a step of blending at least one lower aliphatic compound selected from the group consisting of 2-(methylthio)ethanol, 3-(methylthio)propyl acetate and 3-(methylthio)propionic acid in an amount of 10 ppb or more based on the non-alcoholic beverage to be produced, and the like.

Prior Art Documents

Patent Documents

[0006]

Patent Document 1

Patent Document 2

Summary of the Invention

Problems to be Solved by the Invention

[0007] However, the techniques described in Patent Documents 1 and 2 were not sufficient to impart or enhance an alcohol-like sensation comparable to that of ethanol.

[0008] An object of the present invention is to solve the above problems in the prior art and provide a novel alcohol-like sensation improving agent, an alcohol-like sensation improving composition, a food or beverage product having an improved alcohol-like sensation, and a method for improving the alcohol-like sensation of a food or beverage product.

Means for Solving the Problems

[0009] As a result of intensive studies to solve the above problems, the present inventors have found that a specific compound imparts, enhances and / or modulates an alcoholic sensation, and as a result, improves the alcoholic sensation, and have completed the invention according to the present application.

[0010] Thus, an outline of typical inventions disclosed in the present application will be briefly described as follows.

[0011] [1] An alcoholic sensation improver comprising a compound of the following Group A, one or more compounds selected from the following Group B, and one or more compounds selected from the following Group C. (Group A) 2-(3-benzyloxypropyl)pyridine (Group B) 4-menthyloxy-2-butanone, 2-methyl-4-menthyloxy-2-butanol (Group C) 3-(4-ethoxyphenyl)prop-2-enal, 3-(4-propoxyphenyl)prop-2-enal, 3-(4-isopropoxyphenyl)prop-2-enal, 3-(4-(2-propenyloxy)phenyl)prop-2-enal, 3-(4-butoxyphenyl)prop-2-enal, 3-(4-isobutoxyphenyl)prop-2-enal, 3-(4-(sec-butoxy)phenyl)prop-2-enal, 3-(4-(tert-butoxy)phenyl)prop-2-enal, 3-(4-(3-butenyloxy)phenyl)prop-2-enal [2] An alcoholic sensation improving composition containing, as an active ingredient, a compound of the following Group A, one or more compounds selected from the following Group B, and one or more compounds selected from the following Group C. (Group A) 2-(3-benzyloxypropyl)pyridine (Group B) 4-menthyloxy-2-butanone, 2-methyl-4-menthyloxy-2-butanol (Group C) 3-(4-ethoxyphenyl)prop-2-enal, 3-(4-propoxyphenyl)prop-2-enal, 3-(4-isopropoxyphenyl)prop-2-enal, 3-(4-(2-propenyloxy)phenyl)prop-2-enal, 3-(4-butoxyphenyl)prop-2-enal, 3-(4-isobutoxyphenyl)prop-2-enal, 3-(4-(sec-butoxy)phenyl)prop-2-enal, 3-(4-(tert-butoxy)phenyl)prop-2-enal, 3-(4-(3-butenyloxy)phenyl)prop-2-enal Food or drink containing the alcohol feeling improving agent described in [1] or the alcohol feeling improving composition described in [2]. In the food or drink described in [3], based on the total mass of the food or drink, the concentration of the compound of Group A is in the range of 0.03 ppm or more and 3 ppm or less, the concentration of the compound of Group B is in the range of 0.05 ppm or more and 10 ppm or less, and the concentration of the compound of Group C is in the range of 0.1 ppm or more and 10 ppm or less. Food or drink. A method for improving the alcohol feeling of food or drink, comprising the step of adding the alcohol feeling improving agent described in [1] or the alcohol feeling improving composition described in [2] to the food or drink. In the method for improving the alcohol feeling of food or drink described in [6], in the step, based on the total mass of the food or drink, the concentration of the compound of Group A is in the range of 0.03 ppm or more and 3 ppm or less, the concentration of the compound of Group B is in the range of 0.05 ppm or more and 10 ppm or less, and the concentration of the compound of Group C is in the range of 0.1 ppm or more and 10 ppm or less. A method for improving the alcohol feeling of food or drink, wherein the alcohol feeling improving agent or the alcohol feeling improving composition is added to the food or drink. [Advantages of the Invention]

[0012] According to the present invention, it is possible to provide a novel alcohol feeling improving agent for improving the alcohol feeling of the addition target, a food or drink with an improved alcohol feeling, and a method for improving the alcohol feeling of a food or drink. [Modes for Carrying Out the Invention]

[0013] Hereinafter, an embodiment of the present invention will be described in detail. In this specification, "~" means a range including a lower limit value and an upper limit value. In this specification, "concentration (ppm, ppb, ppt)" represents "mass concentration" unless otherwise specified, and "concentration (%)" represents "mass% (w / w%)" unless otherwise specified, except for those usually expressed as "volume% (v / v%)" such as "alcohol content" and "alcohol degree".

[0014] In this specification, "flavor" means one or more sensations that can be changed by aroma (scent), typically including sensations such as smell and / or taste. Also, in this specification, "alcoholic feeling" means a feeling that reminds one of ethanol, and examples include, but are not limited to, the stimulating feeling, pungency, bitterness, volume feeling, thickness, spread, nasal clearance feeling, drinking feeling, aging feeling, and Western liquor feeling, etc., which are flavor and sensations felt when drinking an alcoholic beverage. Also, in this specification, "throat-clearing feeling" means the volume feeling of the flavor felt when the swallowed beverage passes through the throat, and refers to a comprehensive feeling including the movement of the muscles felt in the throat and the resistance feeling of swallowing, etc.

[0015] In this specification, "flavor improvement (to improve the flavor)" includes imparting (adding newly) flavor, enhancing flavor, and / or adjusting flavor (appropriately suppressing excessive flavor), and means that the flavor is improved as a result of imparting, enhancing, or adjusting the flavor. In this specification, "flavor improvement (to improve the flavor)" includes, as a result of flavor imparting, flavor enhancement, and / or flavor adjustment, enhancing, suppressing, or improving sensations other than smell and / or taste, for example, cold feeling, warm feeling, texture (such as throat-clearing, firmness, viscosity, also called texture), and stimulating sensations such as carbonation and spiciness. Also, in this specification, the flavor of food and drink may be referred to as "taste". Also, in this specification, "addition" includes at least one of simply adding to a certain object by spraying, dropping, etc., and mixing with a certain object.

[0016] In this specification, "improvement of alcohol taste (to improve the alcohol taste)" includes imparting an alcohol taste (adding a new alcohol taste to something without an alcohol taste), enhancing the alcohol taste (moderately increasing the alcohol taste of something that already has an alcohol taste), and / or adjusting the alcohol taste (moderately suppressing an excessive alcohol taste). As a result of imparting, enhancing, or adjusting the alcohol taste, it means that the alcohol taste is improved.

[0017] "Non-alcoholic beverage" generally refers to only beverages with an alcohol content of 0.00% that do not contain any ethanol (sometimes referred to as "completely non-alcoholic beverages"), and in some cases, it also refers to beverages with an alcohol content of less than 1% that do not fall under the category of alcoholic beverages under Article 2 of the Liquor Tax Law and include beverages with an alcohol content of 0.00% that do not contain any ethanol. However, in this specification, for the sake of distinction from "low-alcohol beverages", for convenience, "non-alcoholic beverage" shall refer to beverages with an alcohol content of 0.00% that do not contain any ethanol. Similarly, "low-alcohol beverage" generally has various definitions such as beverages with an alcohol content of less than 11%, less than 10%, 7% or less, beverages with an alcohol content of 1% - 5%, beverages with an alcohol content of 1% - 3%, beverages with an alcohol content of 0.5% - 1%, etc. However, in this specification, "low-alcohol beverage" shall refer to beverages with an alcohol content exceeding 0% and less than 11%. As described later, due to the high effect of the alcohol taste improver of the present invention, beverages with an alcohol content of 0% - 10% are preferred examples of non-alcoholic beverages and low-alcohol beverages to which the alcohol taste improver of the present invention is added, but the addition targets of the alcohol taste improver of the present invention are not limited thereto.

[0018] (Alcohol taste improver) The alcohol taste improver according to an embodiment of the present invention (hereinafter sometimes referred to as the present alcohol taste improver) is composed of a compound of Group A below, one or more compounds selected from Group B below, and one or more compounds selected from Group C below.

[0019] (Group A) 2-(3-benzyloxypropyl)pyridine (Group B) 4-menthyloxy-2-butanone, 2-methyl-4-menthyloxy-2-butanol (Group C) 3-(4-ethoxyphenyl)prop-2-enal, 3-(4-propoxyphenyl)prop-2-enal, 3-(4-isopropoxyphenyl)prop-2-enal, 3-(4-(2-propenyloxy)phenyl)prop-2-enal, 3-(4-butoxyphenyl)prop-2-enal, 3-(4-isobutoxyphenyl)prop-2-enal, 3-(4-(sec-butoxy)phenyl)prop-2-enal, 3-(4-(tert-butoxy)phenyl)prop-2-enal, 3-(4-(3-butenyloxy)phenyl)prop-2-enal

[0020] As shown by an example in the following examples, this alcohol feeling improver can improve the alcohol feeling by adding it to various objects to be added.

[0021] The objects to which this alcohol feeling improver is added are not particularly limited, and examples include flavoring compositions or consumer products. Examples of flavoring compositions include perfume compositions, flavor enhancing compositions, flavor improving compositions, flavor modulating compositions, taste imparting compositions, taste enhancing compositions, taste improving compositions, or taste modulating compositions. Examples of consumer products include food and beverages, cosmetics, pharmaceuticals, or health and hygiene products.

[0022] Therefore, the present alcohol feeling improver can impart an alcohol feeling to various flavoring compositions to be added, or enhance or adjust the alcohol feeling of various flavoring compositions to be added, and as a result, can improve the alcohol feeling of the various flavoring compositions. Further, the present alcohol feeling improver can impart an alcohol feeling to various food and beverage products to be added, or enhance or adjust the alcohol feeling of various food and beverage products to be added, and as a result, can improve the alcohol feeling of the various food and beverage products. Therefore, the present alcohol feeling improver can be alternatively referred to as an alcohol feeling imparting agent, an alcohol feeling enhancing agent, and / or an alcohol feeling adjusting agent.

[0023] The concentration of the present alcohol feeling improver in the flavoring composition to be added can be arbitrarily determined according to the aroma characteristics of the flavoring composition and / or the object to which the flavoring composition is added. However, in view of adding the flavoring composition added with the present alcohol feeling improver to consumer products, it is preferable to use as a reference the concentration of the compounds in groups A, B, and C constituting the present alcohol feeling improver in the consumer products.

[0024] Specifically, based on the total mass of the food and beverage product to be added, the concentration of the compound in group A is preferably in the range of 0.03 ppm or more and 3 ppm or less, the concentration of the compound in group B is preferably in the range of 0.05 ppm or more and 10 ppm or less, and the concentration of the compound in group C is preferably in the range of 0.1 ppm or more and 10 ppm or less. Therefore, based on the total mass of the flavoring composition to be added, the concentrations of the compounds in groups A, B, and C are preferably 10 to 10,000 times the concentrations in the above-described food and beverage products. Taking as an example the case where the concentration is 1,000 times the concentration in the above-described food and beverage products, based on the total mass of the flavoring composition to be added, the concentration of the compound in group A is preferably in the range of 30 ppm (0.003%) or more and 3,000 ppm (0.3%) or less, the concentration of the compound in group B is preferably in the range of 50 ppm (0.005%) or more and 10,000 ppm (1%) or less, and the concentration of the compound in group C is preferably in the range of 100 ppm (0.01%) or more and 10,000 ppm (1%) or less.

[0025] The compounds in Group A, Group B, and Group C will be described in detail below. The compound constituting Group A is 2-(3-benzyloxypropyl)pyridine. This compound has a somewhat herbal and green, tea-like natural aroma, but there was no known effect of improving the alcohol smell when used in combination with the compounds constituting Group B and the compounds constituting Group C.

[0026] The compounds constituting Group B are 4-menthyloxy-2-butanone and 2-methyl-4-menthyloxy-2-butanol. These compounds have a fresh and characteristic herbal aroma, but there was no known effect of improving the alcohol smell when used in combination with the compounds constituting Group A and the compounds constituting Group C. There are eight isomers derived from the menthyl group in these compounds, but they are not particularly limited, and a mixture of isomers may also be used.

[0027] The compounds constituting the C group are 3-(4-ethoxyphenyl)prop-2-enal, 3-(4-propoxyphenyl)prop-2-enal, 3-(4-isopropoxyphenyl)prop-2-enal, 3-(4-(2-propenyloxy)phenyl)prop-2-enal, 3-(4-butoxyphenyl)prop-2-enal, 3-(4-isobutoxyphenyl)prop-2-enal, 3-(4-(sec-butoxy)phenyl)prop-2-enal, 3-(4-(tert-butoxy)phenyl)prop-2-enal, 3-(4-(3-butenyloxy)phenyl)prop-2-enal. The compounds constituting the C group can be paraphrased as 3-(4-alkoxyphenyl)prop-2-enal or 3-(4-alkenyloxyphenyl)prop-2-enal (provided that the alkoxy group and the alkenyloxy group are each limited to those having 2 to 4 carbon atoms). These compounds have aromas such as spicy, waxy, fatty, green, and metallic-like, but no effect of improving the alcohol feeling is known when used in combination with the compounds constituting the A group and the compounds constituting the B group. In addition, the cis-trans isomers of the compounds constituting the C group are not particularly limited, and a mixture of isomers may also be used.

[0028] The various compounds constituting the A group, B group, and C group can be obtained by any method that can be carried out by those skilled in the art, for example, by purchasing as a food flavor compound or a reagent, extracting from natural products, or synthesizing according to a conventional method.

[0029] As a synthesis method, 2-(3-benzyloxypropyl)pyridine, which is a compound constituting Group A, can be synthesized, for example, by reacting 2-pyridinepropanol with benzyl chloride in the presence of a base. Among the compounds constituting Group B, 4-menthyloxy-2-butanone can be synthesized, for example, by Michael addition from menthol and methyl vinyl ketone. Among the compounds constituting Group B, 4-menthyloxy-2-butanol can be synthesized by reacting 4-menthyloxy-2-butanone with a Grignard reagent. Among the compounds constituting Group C, for example, 3-(4-alkoxyphenyl)prop-2-enal can be prepared by using the synthesis reaction described in Japanese Patent Application Laid-Open No. 2000-507227. That is, 4-alkoxybenzaldehyde dimethyl acetal and methyl vinyl ether are reacted using a Lewis acid catalyst, and this compound is hydrolyzed to obtain 3-(4-alkoxyphenyl)prop-2-enal.

[0030] The various compounds constituting the above-mentioned Group A, Group B, and Group C obtained may be further purified by means such as column chromatography or vacuum distillation as necessary.

[0031] The compound of Group B contained in the present alcohol feeling improver may be composed of only one kind of compound selected from Group B, or may be composed of a combination of two or more kinds of compounds selected from Group B, and exhibits the above-described effects. Similarly, the compound of Group C contained in the present alcohol feeling improver may be composed of only one kind of compound selected from Group C, or may be composed of a combination of two or more kinds of compounds selected from Group C, and exhibits the above-described effects.

[0032] As shown in the examples described later, among the present alcohol feeling improvers, 4-menthyloxy-2-butanone as the compound constituting Group B and 3-(4-isopropoxyphenyl)prop-2-enal as the compound constituting Group C were found to exhibit particularly excellent alcohol feeling improving effects.

[0033] The article to which the flavoring composition containing the present alcohol feeling improver is added is not particularly limited, but examples thereof include consumer goods such as food and drink products, cosmetics, pharmaceuticals, or health and hygiene products. Among them, food and drink products are preferred, and non-alcoholic beverages and low-alcohol beverages are particularly preferred.

[0034] The flavor of the food or drink to which the flavoring composition containing the present alcohol feeling improver can be added is not particularly limited. Examples include various citrus flavors such as lemon, orange, grapefruit, lime, mandarin, tangerine, kabosu, sudachi, hassaku, iyo-kan, yuzu, shikuwasa, kumquat, etc.; various fruit flavors such as strawberry, blueberry, raspberry, apple, cherry, plum, apricot, peach, pineapple, banana, melon, mango, papaya, kiwi, pear, grape, muscat, kyoho, etc.; milk flavors such as milk, yogurt, butter, etc.; vanilla flavor; various tea flavors such as green tea, black tea, oolong tea, herbal tea, etc.; coffee flavor; cola flavor; cacao flavor; cocoa flavor; various mint flavors such as spearmint, peppermint, etc.; various spice or herb flavors such as cinnamon, camomile, cardamom, caraway, cumin, clove, pepper, coriander, sansho, shiso, ginger, star anise, thyme, chili pepper, nutmeg, basil, marjoram, rosemary, laurel, garlic, wasabi, etc.; various nut flavors such as almond, cashew nut, walnut, etc.; various liquor flavors such as wine, brandy, whiskey, rum, gin, liqueur, sake, shochu, beer, etc.; vegetable flavors such as onion, celery, carrot, tomato, cucumber, etc.; various livestock meat flavors such as chicken, duck, pork, beef, mutton, horse meat, etc.; various fish and shellfish and seaweed flavors such as red meat fish such as tuna, white meat fish such as mackerel, tai, salmon, horse mackerel, freshwater fish such as ayu, carp, koi, shellfish such as turban shell, clam, asari, shijimi, various crustaceans such as shrimp, crab, various seaweeds such as wakame, kelp, etc.; various grain flavors such as rice, barley, wheat, malt, etc.; various fat flavors such as livestock fats such as beef tallow, chicken fat, lard, and various fish oils, etc. Examples of the food or drink include those having one or more of the above flavors.That is, it may be a food or drink that gives the impression of only one of the above flavors, or a food or drink that gives the impression of two or more flavors. The multiple flavors may be of the same type or different types. For example, as an example of the former, it includes giving the impression of multiple fruit flavors such as banana, peach, and apple flavors among fruit flavors (so-called mixed fruit flavors). As an example of the latter, it includes those that give the impression of citrus flavors such as lemon and milk flavors (such as citrus-flavored lactic acid bacteria beverages), and those that give the impression of mint flavors, citrus flavors, and cola flavors (such as mint or lemon-flavored cola beverages).

[0035] More specific examples of beverages include, as non-alcoholic beverages, carbonated beverages, beverages containing fruit juice and / or vegetable juice, tea beverages, milk, soy milk and other plant-based milks, milk beverages, drink-type yogurts, coffee, cocoa, nutritional drinks, sports drinks, mineral waters, malt beverages, fruit juice beverages of fruits such as apples, grapes, citrus fruits (grapefruits, oranges, lemons, etc.), and soft drinks with fruit juice, fruit pulp beverages, and fruit beverages with fruit pieces; preferred beverage products such as coffee, cocoa, green tea, black tea, oolong tea, soft drinks, cola beverages, carbonated beverages (such as ciders with various flavors such as citrus fragrance), lactic acid bacteria beverages; beverages containing crude drugs or herbs; functional beverages such as cola beverages, fruit juice beverages, milk beverages, sports drinks, honey beverages, vitamin supplements, mineral supplements, nutritional drinks, tonic drinks, lactic acid bacteria beverages; non-alcoholic preferred beverages such as alcoholic taste beverages with various liquor flavors (beer flavor, umeshu flavor, chu-hi flavor, etc.) (with an alcohol content of less than 1%, and drinks with a taste similar to beer, highballs, cocktails, etc.); other fermented liquors (sparkling) or liqueurs (sparkling) such as wine, shochu, awamori, sake, beer, chu-hi, cocktail drinks, sparkling wines, fruit wines, herbal wines, so-called "third beer", etc., or alcoholic beverages containing these; etc.

[0036] More specific examples of foods include confectioneries such as steamed buns, mochi cakes, bean jams, sheep jelly, water sheep jelly, mochi balls, jelly, castella, candy balls, biscuits, crackers, potato chips, cookies, pies, puddings, buttercream, custard cream, cream puffs, waffles, sponge cakes, doughnuts, chocolate, chewing gum, caramel, candies, peanut paste or other pastes, etc. (Among them, confectioneries using alcohol such as Japanese sake and Western liquor for flavoring are preferred.); breads; pickled foods such as pickled vegetables in Nara style, pickled vegetables in bran, pickled plums, pickled vegetables in the style of Fukushinzuke, pickled vegetables in the style of Bettarazuke, pickled daikon radish slices, pickled ginger, rakkyo, pickled vegetables in miso, pickled daikon radish, and the bases of these pickled foods, etc.; seafood such as mackerel, sardines, saury, salmon, tuna, bonito, whale, flounder, needlefish, ayu, etc., squids such as surume squid, spear squid, striped squid, firefly squid, etc., octopuses such as common octopus, longarm octopus, etc., shrimps such as kuruma shrimp, button shrimp, ise shrimp, black tiger shrimp, etc., crabs such as taraba crab, snow crab, horsehair crab, hairy crab, etc., shellfishes such as clams, ark clams, scallops, oysters, mussels, etc. (Among them, pickled seafood in the style of using the lees of these seafood and pickled seafood in the style of Saikyo are preferred.); processed food and drink products made from seafood such as canned foods, cooked fish, tsukudani, surimi, processed fishery products (such as chikuwa, kamaboko, fried kamaboko, crab leg kamaboko, etc.), fried foods, tempura, etc.; meats such as chicken, pork, beef, mutton, horse meat, etc.; processed food and drink products using meat such as curry, stew, beef stew, hayashi rice sauce, meat sauce, hamburg, soups (such as corn soup, tomato soup, consommé soup, etc.), meatballs, kakuni, canned meat (Among them, processed food and drink products using alcohol such as Japanese sake, wine, Shaoxing wine, etc. as seasonings are preferred.));soy sauce, powdered soy sauce, miso, powdered miso, moromi, hishio, furikake, ochazuke seasoning, margarine, mayonnaise, dressing, vinegar, sanbai-zu, powdered sushi vinegar, Chinese seasoning, tempura sauce, noodle sauce (kelp stock or bonito stock, etc.), sauce (medium-thick sauce, tomato sauce, etc.), ketchup, yakiniku sauce, curry roux, stew seasoning, soup seasoning, dashi seasoning (kelp stock or bonito stock, etc.), compound seasoning, new Examples of such vegetable stews include seasonings such as phosphorus, and animal or vegetable broth-flavored foods and beverages with these seasonings added; stewed vegetables, Chikuzen-ni, oden, hot pots, and other stewed dishes; vegetables such as tomatoes, bell peppers, celery, melon, bitter melon, carrots, potatoes, asparagus, bracken, and osmanthus, as well as vegetable-based beverages and vegetable soups containing these vegetables; and take-out bento fillings and side dishes.

[0037] Furthermore, the flavor-imparting composition containing the alcohol sensation improver of the present invention can be added to various flavor compositions to improve the alcohol sensation of the flavor compositions. Specific examples of various flavor compositions include flavor compositions for food and beverages (also called flavor compositions) and flavor compositions for cosmetics (also called fragrance compositions). The form of the various flavor compositions is not particularly limited, and examples include water-soluble flavor compositions, oil-soluble flavor compositions, emulsion flavor compositions, and powder flavor compositions.

[0038] (Alcohol Sensation Improving Composition) The alcohol sensation improving composition according to one embodiment of the present invention (hereinafter may be referred to as "the present alcohol sensation improving composition") contains, as active ingredients, a compound in Group A below, one or more compounds selected from Group B below (hereinafter may be referred to as "compounds in Group B"), and one or more compounds selected from Group C below (hereinafter may be referred to as "compounds in Group C"):

[0039] (Group A) 2-(3-benzyloxypropyl)pyridine (Group B) 4-menthyloxy-2-butanone, 2-methyl-4-menthyloxy-2-butanol (Group C) 3-(4-ethoxyphenyl)prop-2-enal, 3-(4-propoxyphenyl)prop-2-enal, 3-(4-isopropoxyphenyl)prop-2-enal, 3-(4-(2-propenyloxy)phenyl)prop-2-enal, 3-(4-butoxyphenyl)prop-2-enal, 3-(4-isobutoxyphenyl)prop-2-enal, 3-(4-(sec-butoxy)phenyl)prop-2-enal, 3-(4-(tert-butoxy)phenyl)prop-2-enal, 3-(4-(3-butenyloxy)phenyl)prop-2-enal

[0040] As shown by an example in the following examples, the present alcohol feeling improvement composition can improve the alcohol feeling by adding it to various addition targets.

[0041] The addition targets of the present alcohol feeling improvement composition are not particularly limited, and examples include flavor imparting compositions or consumer products. Examples of flavor imparting compositions include, for example, perfume compositions, flavor enhancing compositions, flavor improving compositions, flavor modulating compositions, taste imparting compositions, taste enhancing compositions, taste improving compositions, or taste modulating compositions. Examples of consumer products include, for example, food and beverages, cosmetics, pharmaceuticals, or health and hygiene products.

[0042] Therefore, the present alcohol feeling improvement composition can impart an alcohol feeling to various flavor imparting compositions of the addition target, or enhance or adjust the alcohol feeling of various flavor imparting compositions of the addition target, and as a result, improve the alcohol feeling of the various flavor imparting compositions. In addition, the present alcohol feeling improvement composition can impart an alcohol feeling to various food and beverages of the addition target, or enhance or adjust the alcohol feeling of various food and beverages of the addition target, and as a result, improve the alcohol feeling of the various food and beverages. Therefore, the present alcohol feeling improvement composition can be alternatively referred to as an alcohol feeling imparting composition, an alcohol feeling enhancing composition, and / or an alcohol feeling adjusting composition.

[0043] This alcohol feeling improvement composition may be composed only of the compounds in Group A, Group B, and Group C, or may contain other components as long as it contains a predetermined amount of the compounds in Group A, Group B, and Group C as active ingredients. That is, the compounds in Group A, Group B, and Group C (which may contain other components) obtained by any method that can be carried out by those skilled in the art described above, for example, purchased as a food flavor compound or reagent, extracted from natural products, or synthesized according to established methods, can be used as they are as this alcohol feeling improvement composition, or added to a solvent or other flavoring composition and used as this alcohol feeling improvement composition. Further, when this alcohol feeling improvement composition contains a solvent and / or other fragrance components as components other than the compounds in Group A, Group B, and Group C, this alcohol feeling improvement composition itself can also be used as a fragrance composition. In addition, when this alcohol feeling improvement composition contains a solvent as a component other than the compounds in Group A, Group B, and Group C, there is no problem in using ethanol as this solvent. However, since ethanol derived from the solvent is also added to the addition target of this alcohol feeling improvement composition, it is necessary to pay attention to the alcohol concentration after addition. In the examples described later, in order not to affect the evaluation of the alcohol feeling, a sensory evaluation was conducted under the condition that this alcohol feeling improvement composition does not contain ethanol (propylene glycol is used instead of ethanol as the solvent).

[0044] The concentrations of the compounds in Group A, Group B, and Group C in this alcohol feeling improvement composition can be arbitrarily determined according to the fragrance characteristics of this alcohol feeling improvement composition and / or the addition target of this alcohol feeling improvement composition. However, in view of adding this alcohol feeling improvement composition to consumer products, it is preferable to use as a reference the concentrations of the compounds in Group A, Group B, and Group C contained in this alcohol feeling improvement composition in the consumer products.

[0045] Specifically, based on the total mass of the food or drink to which it is added, the concentration of the compounds in Group A is preferably in the range of 0.03 ppm or more and 3 ppm or less, the concentration of the compounds in Group B is preferably in the range of 0.05 ppm or more and 10 ppm or less, and the concentration of the compounds in Group C is preferably in the range of 0.1 ppm or more and 10 ppm or less. Therefore, based on the total mass of the alcohol feeling improvement composition of the present case, it is preferable that the concentrations of the compounds in Group A, Group B, and Group C are 10 to 10,000 times the concentrations in the above-mentioned food or drink. Taking the case where it is 1,000 times the concentration in the above-mentioned food or drink as an example, based on the total mass of the alcohol feeling improvement composition of the present case, the concentration of the compounds in Group A is in the range of 30 ppm (0.003%) or more and 3,000 ppm (0.3%) or less, the concentration of the compounds in Group B is in the range of 50 ppm (0.005%) or more and 10,000 ppm (1%) or less, and the concentration of the compounds in Group C is in the range of 100 ppm (0.01%) or more and 10,000 ppm (1%) or less.

[0046] (Flavor composition) The flavor composition according to one embodiment of the present invention (hereinafter sometimes referred to as the present flavor composition) is an aspect of the alcohol feeling improvement composition of the present case, contains the compounds in Group A, Group B, and Group C as active ingredients, and can be added to various foods and drinks for the purpose of flavoring. The present flavor composition can impart an alcohol feeling to various foods and drinks to which it is added, or enhance or adjust the alcohol feeling of various foods and drinks to which it is added, and as a result, can improve the alcohol feeling of the various foods and drinks. That is, the present flavor composition is preferably a flavor composition for foods and drinks.

[0047] The form of the present flavor composition is not particularly limited, and examples thereof include water-soluble flavor compositions, oil-soluble flavor compositions, emulsified flavor compositions, and powdered flavor compositions.

[0048] The fragrance notes for which the present fragrance composition can be used are not limited, and may be any fragrance notes that can impart, enhance or improve a good fragrance to food and beverages by the present fragrance composition. However, since the present fragrance composition improves the alcoholic feeling of food and beverages, it is preferably configured as a lemon fragrance-imparting composition, a grapefruit fragrance-imparting composition, an orange fragrance-imparting composition, a grape fragrance-imparting composition, a peach fragrance-imparting composition, an apple fragrance-imparting composition, a pineapple fragrance-imparting composition, a berry fragrance-imparting composition, a beer fragrance-imparting composition, a wine fragrance-imparting composition, a vanilla fragrance-imparting composition, a rum fragrance-imparting composition, a whiskey fragrance-imparting composition, a brandy fragrance-imparting composition, a chocolate fragrance-imparting composition, a milk fragrance-imparting composition, a coffee fragrance-imparting composition, etc.

[0049] The concentrations of the compounds in Group A, Group B and Group C in the present fragrance composition can be arbitrarily determined according to the fragrance characteristics of the present fragrance composition and / or the object to which the present fragrance composition is added. However, in view of adding the present fragrance composition to consumer products, it is preferable to use as a reference the concentrations of the compounds in Group A, Group B and Group C contained in the present fragrance composition in the consumer products.

[0050] Specifically, based on the total mass of the food and beverage to which it is added, the concentration of the compound in Group A is preferably in the range of 0.03 ppm or more and 3 ppm or less, the concentration of the compound in Group B is preferably in the range of 0.05 ppm or more and 10 ppm or less, and the concentration of the compound in Group C is preferably in the range of 0.1 ppm or more and 10 ppm or less. Therefore, based on the total mass of the present fragrance composition, it is preferable that the concentrations of the compounds in Group A, Group B and Group C are 10 to 10,000 times the concentrations in the above-mentioned food and beverages. Taking the case where it is 1,000 times the concentration in the above-mentioned food and beverages as an example, based on the total mass of the present fragrance composition, the concentration of the compound in Group A is preferably in the range of 30 ppm (0.003%) or more and 3,000 ppm (0.3%) or less, the concentration of the compound in Group B is preferably in the range of 50 ppm (0.005%) or more and 10,000 ppm (1%) or less, and the concentration of the compound in Group C is preferably in the range of 100 ppm (0.01%) or more and 10,000 ppm (1%) or less.

[0051] The present fragrance composition may contain the following compounds or components, such as various types of fragrance compounds or fragrance compositions, oil-soluble colorants, vitamins, functional substances, fish meat extracts, livestock meat extracts, plant extracts, yeast extracts, animal and plant proteins, animal and plant protein hydrolysates, starch, dextrin, sugars, amino acids, nucleic acids, organic acids, solvents, etc.

[0052] Examples of flavoring compounds and the like include those described in "Japan Patent Office Official Gazette, Collection of Well-Known and Commonly Used Technology (Flavors) Part II Food Flavors, published January 14, 2000," "Survey on the Actual Use of Food Flavoring Compounds in Japan" (Report of the Ministry of Health, Labour and Welfare's Research on FY 2000, Japan Flavor and Flavor Manufacturers Association, published March 2001), and "Synthetic Flavors: Chemistry and Product Knowledge" (revised and expanded new edition published December 20, 2016, edited by the Synthetic Flavors Editorial Committee, Chemical Daily Co., Ltd.).

[0053] Specific examples of synthetic fragrance compounds include hydrocarbon compounds such as monoterpenes such as α-pinene, β-pinene, γ-terpinene, myrcene, camphene, and limonene, sesquiterpenes such as valencene, cedrene, caryophyllene, and longifolene, and 1,3,5-undecatriene.

[0054] Examples of the alcohol compound include saturated alcohols such as butanol, pentanol, 3-octanol, and hexanol; unsaturated alcohols such as (Z)-3-hexen-1-ol, prenol, and 2,6-nonadienol; terpene alcohols such as linalool, geraniol, citronellol, tetrahydromyrcenol, farnesol, nerolidol, cedrol, α-terpineol, terpinen-4-ol, and borneol; and aromatic alcohols such as benzyl alcohol, phenylethyl alcohol, and cinnamyl alcohol.

[0055] Examples of aldehyde compounds include saturated aldehydes such as acetaldehyde, hexanal, octanal, and decanal; unsaturated aldehydes such as (E)-2-hexenal and 2,4-octadienal; terpene aldehydes such as citronellal, hydroxycitronellal, citral, myrtenal, and perillyl aldehyde; and aromatic aldehydes such as benzaldehyde, cinnamyl aldehyde, vanillin, ethyl vanillin, heliotropin, and p-tolyl aldehyde.

[0056] Examples of ketone compounds include saturated and unsaturated ketones such as 2-heptanone, 2-undecanone, 1-octen-3-one, acetoin, and 6-methyl-5-hepten-2-one (methylheptenone); diketones and hydroxyketones such as diacetyl, 2,3-pentanedione, maltol, ethyl maltol, cyclotene, and 2,5-dimethyl-4-hydroxy-3(2H)-furanone; terpene ketones such as carvone, menthone, and nootkatone; ketones derived from terpene degradation products such as α-ionone, β-ionone, and β-damascenone; and aromatic ketones such as raspberry ketone.

[0057] Examples of furan or ether compounds include furfuryl alcohol, furfural, rose oxide, linalool oxide, menthofuran, teaspirane, estragole, eugenol, and 1,8-cineole.

[0058] Examples of ester compounds include aliphatic esters such as ethyl acetate, isoamyl acetate, octyl acetate, ethyl butyrate, ethyl isobutyrate, isoamyl butyrate, ethyl 2-methylbutyrate, ethyl isovalerate, 2-methylbutyl isobutyrate, ethyl hexanoate, allyl hexanoate, ethyl heptanoate, ethyl octanoate, isoamyl isovalerate, and ethyl nonanoate; terpene alcohol esters such as linalyl acetate, geranyl acetate, lavandulyl acetate, terpinyl acetate, and neryl acetate; and aromatic esters such as benzyl acetate, methyl salicylate, methyl cinnamate, cinnamyl propionate, ethyl benzoate, cinnamyl isovalerate, and ethyl 3-methyl-2-phenylglycidate.

[0059] Examples of lactone compounds include saturated lactones such as γ-decalactone, γ-dodecalactone, δ-decalactone, and δ-dodecalactone, and unsaturated lactones such as 7-decen-4-olide and 2-decen-5-olide.

[0060] Examples of acid compounds include saturated and unsaturated fatty acids such as acetic acid, butyric acid, isovaleric acid, hexanoic acid, octanoic acid, stearic acid, oleic acid, linoleic acid, and linolenic acid.

[0061] Examples of nitrogen-containing compounds include indole, skatole, pyridine, alkyl-substituted pyrazine, methyl anthranilate, and trimethylpyrazine.

[0062] Examples of sulfur-containing compounds include methanethiol, dimethyl sulfide, dimethyl disulfide, allyl isothiocyanate, 3-methyl-2-buten-1-thiol, 3-methyl-2-butanethiol, 3-methyl-1-butanethiol, 2-methyl-1-butanethiol, 3-mercaptohexanol, 4-mercapto-4-methyl-2-pentanone, 3-mercaptohexyl acetate, p-mentha-8-thiol-3-one, and furfuryl mercaptan.

[0063] 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, and labdanum.

[0064] Examples of various animal and plant extracts include extracts of herbs or spices, extracts of coffee, green tea, black tea, or oolong tea, and milk or milk processed products and various enzymatic decomposition products such as their lipases or proteases.

[0065] As the form of the present perfume composition, solutions in which the compounds of Group A, Group B and Group C and other components are dissolved in a water-soluble or oil-soluble solvent, emulsified preparations, powder preparations, or other solid preparations (such as solid fats) are preferred.

[0066] Examples of the water-soluble solvent include ethanol, methanol, acetone, tetrahydrofuran, acetonitrile, 2-propanol, methyl ethyl ketone, glycerin, propylene glycol, dipropylene glycol and the like. Among these, from the viewpoint of use in foods and drinks, propylene glycol, ethanol or glycerin is particularly preferred. Examples of the oil-soluble solvent include vegetable oils, animal fats, refined oils and fats (for example, processed oils such as medium-chain fatty acid triglycerides (MCT), and short-chain fatty acid triglycerides such as triacetin and tripropionin), various essential oils, triethyl citrate and the like.

[0067] In addition, in order to obtain an emulsified preparation, the flavoring composition can be obtained by emulsifying it together with a water-soluble solvent and an emulsifier. The emulsification method of the flavoring composition is not particularly limited, and various emulsifiers conventionally used in foods and beverages, etc., for example, fatty acid monoglycerides, fatty acid diglycerides, fatty acid triglycerides, propylene glycol fatty acid esters, sucrose fatty acid esters, polyglycerol 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, or casein sodium, etc. can be used, and an emulsion with excellent stability can be obtained by performing an emulsification treatment using a homomixer, a colloid mill, a rotary disk type homogenizer, a high-pressure homogenizer, etc. The usage amount of these emulsifiers is not strictly limited and can be varied over a wide range according to the type of emulsifier used, etc. Further, in order to stabilize the emulsified state, in addition to water, for example, one or a mixture of two or more polyhydric alcohols such as glycerin, propylene glycol, sorbitol, maltitol, sucrose, glucose, trehalose, sugar solution, and reduced starch syrup can be added to such an emulsion.

[0068] In addition, the emulsion thus obtained can be made into a powder preparation by drying if desired. When powdering, if necessary, saccharides such as gum arabic, trehalose, dextrin, sugar, lactose, glucose, starch syrup, and reduced starch syrup can also be appropriately added. The usage amounts of these can be appropriately selected according to the properties desired for the powder preparation, etc.

[0069] In addition to the above, the perfume composition may contain, if necessary, components commonly used in perfume compositions. For example, it may contain solvents such as water and ethanol, and perfume retention agents such as ethylene glycol, propylene glycol, dipropylene glycol, glycerin, hexyl glycol, benzyl benzoate, triethyl citrate, diethyl phthalate, harcolin, medium-chain fatty acid triglycerides, and medium-chain fatty acid diglycerides.

[0070] This perfume composition may be added to various food and beverages by itself, or in combination with one or more selected from water-soluble and oil-soluble perfumes, emulsified perfume compositions, natural essential oils, natural perfumes, and synthetic perfumes (perfume compounds) described in the above-mentioned "Patent Office Gazette, Collection of Well-Known and Conventional Technologies (Perfumes), Part II, Food Perfumes, Issued on January 14, 2000", "Investigation of the Actual Use of Food Perfume Compounds in Japan" (Report on Hygiene Sciences Research in 2000, Japan Perfume Industry Association, Issued in March 2001), and "Synthetic Perfumes - Chemistry and Product Knowledge" (Supplemental New Edition Issued on December 20, 2016, Edited by the Synthetic Perfume Editorial Committee, Chemical Industry Daily Co., Ltd.) and then added to various food and beverages.

[0071] (Food and beverages) The food and beverage according to one embodiment of the present invention (hereinafter sometimes referred to as the present food and beverage) contains a predetermined amount of the present alcohol feeling improver or the present alcohol feeling improving composition. As shown in an example in the following examples, the present food and beverage has an effective amount of the present alcohol feeling improver composed of the compounds of Group A, Group B, and Group C, or the present flavor imparting composition containing the compounds of Group A, Group B, and Group C as active ingredients added thereto, so that the alcohol feeling is improved.

[0072] More specifically, since the present alcohol feeling improver or the present alcohol feeling improving composition is added to the present food and beverage, the alcohol feeling is imparted, enhanced, or adjusted, and as a result, the alcohol feeling of the food and beverage is improved.

[0073] The addition amount of the alcohol sensation improving agent or the alcohol sensation improving composition for the food or drink of the present case can be arbitrarily determined according to the degree of the alcohol sensation improving effect by the compounds of the above-mentioned Group A, Group B and Group C, and / or the flavor of the food or drink itself. However, as described above, based on the total mass of the food or drink of the present case, the concentration of the compound of Group A is in the range of 0.03 ppm or more and 3 ppm or less, the concentration of the compound of Group B is in the range of 0.05 ppm or more and 10 ppm or less, and the concentration of the compound of Group C is preferably in the range of 0.1 ppm or more and 10 ppm or less.

[0074] (Method for improving the alcohol sensation of food or drink) The method for improving the alcohol sensation of a food or drink according to an embodiment of the present invention includes a step of adding an alcohol sensation improving agent composed of the compounds of Group A, Group B and Group C, or an alcohol sensation improving composition containing the compounds of Group A, Group B and Group C as active ingredients to the food or drink.

[0075] As shown by an example in the examples described below, by adding the alcohol sensation improving agent or the alcohol sensation improving composition of the present case to various foods or drinks, the alcohol sensation of the food or drink can be improved.

[0076] When adding the alcohol sensation improving agent or the alcohol sensation improving composition of the present case to a food or drink, the concentration of the alcohol sensation improving agent or the alcohol sensation improving composition of the present case can be arbitrarily determined according to the flavor characteristics of the food or drink. However, as described above, based on the total mass of the food or drink of the present case, the concentration of the compound of Group A is in the range of 0.03 ppm or more and 3 ppm or less, the concentration of the compound of Group B is in the range of 0.05 ppm or more and 10 ppm or less, and the concentration of the compound of Group C is in the range of 0.1 ppm or more and 10 ppm or less, it is preferable to add the alcohol sensation improving agent or the alcohol sensation improving composition of the present case.

[0077] In the method for improving the flavor of food and drink according to the present embodiment, the method of adding the present alcohol feeling improver or the present alcohol feeling improving composition to food and drink is not particularly limited. Also, the timing of adding the present alcohol feeling improver or the present alcohol feeling improving composition to food and drink is not particularly limited.

Example

[0078] Hereinafter, the present invention will be described more specifically by way of examples. Note that the present invention is not limited thereto.

[0079] [Example 1] Addition effect to lemon - flavored completely non - alcoholic beverage Propylene glycol solutions (1% - 10 ppm) of commercially available compounds in the following Group A, Group B, and Group C were each prepared (also used in the following examples).

[0080] (Group A) 2 - (3 - benzyloxypropyl) pyridine (Group B) 4 - menthyloxy - 2 - butanone, 2 - methyl - 4 - menthyloxy - 2 - butanol (Group C) 3 - (4 - ethoxyphenyl) prop - 2 - enal, 3 - (4 - propoxyphenyl) prop - 2 - enal, 3 - (4 - isopropoxyphenyl) prop - 2 - enal, 3 - (4 - (2 - propenyloxy) phenyl) prop - 2 - enal, 3 - (4 - butoxyphenyl) prop - 2 - enal, 3 - (4 - isobutoxyphenyl) prop - 2 - enal, 3 - (4 - (sec - butoxy) phenyl) prop - 2 - enal, 3 - (4 - (tert - butoxy) phenyl) prop - 2 - enal, 3 - (4 - (3 - butenyloxy) phenyl) prop - 2 - enal

[0081] Also, a basic lemon flavor (basic compounded flavor) was prepared according to Formulation 1 in Table 1 below.

[0082]

Table 1

[0083] Then, 1.3 kg of fructose glucose liquid sugar (Bx 75°), 0.014 kg of citric acid (crystalline), 0.004 kg of trisodium citrate, and 0.02 kg of basic lemon flavor were added with ion-exchanged water and dissolved to make a total of 10 L, and a lemon-flavored beverage stock solution was prepared.

[0084] Propylene glycol solutions of the compounds in Group A, Group B, and Group C were added to this lemon-flavored beverage stock solution so that the compounds in Group A, Group B, and Group C would have the respective concentrations corresponding to Invention Products 1-1 to 1-47 in Table 2 below, and each preparation solution was prepared. After each preparation solution was put into a can, carbon dioxide gas was added so that it would be 2.0 kg / cm 2 and sealed with a can seamer (winder). After the central temperature of the can reached 65°C in warm water, it was maintained at 65°C for 10 minutes for sterilization, and then cooled with cold water to produce the lemon-flavored beverages of Invention Products 1-1 to 1-47. Similarly, propylene glycol solutions of the compounds in Group A, Group B, and Group C were added so that the compounds in Group A, Group B, and Group C would have the respective concentrations corresponding to Comparative Products 1-1 to 1-6 in Table 2 below, and each preparation solution was prepared. Through the same process, lemon-flavored beverages of Comparative Products 1-1 to 1-6 were produced. Also, a lemon-flavored beverage produced through the same process except that the propylene glycol solutions of the compounds in Group A, Group B, and Group C were not added to the lemon-flavored beverage stock solution was used as the lemon-flavored beverage of Control Product 1.

[0085] Then, sensory evaluations were conducted on the obtained lemon-flavored beverages of Invention Products 1-1 to 1-47 and Comparative Products 1-1 to 1-6 by 15 well-trained panelists (with more than 10 years of experience). The sensory evaluation was to let the panelists comment on the difference in flavor when Invention Products 1-1 to 1-47 and Comparative Products 1-1 to 1-6 were compared with Control Product 1, and regarding the alcohol feeling (a feeling that reminds one of ethanol, such as the stimulating feeling, pungent feeling, bitter feeling, volume feeling, thickness, spread, nasal passage feeling, drinking feeling, aging feeling, foreign liquor feeling, etc. of the flavor and feeling when drinking an alcoholic beverage) when compared with Control Product 1, the panelists scored according to the following evaluation criteria and the average was taken.

[0086] <Evaluation Criteria for Alcoholic Sensation> Significantly increased compared to Control 1: 5 points Greatly increased compared to Control 1: 4 points Somewhat increased compared to Control 1: 3 points Slightly increased compared to Control 1: 2 points Equivalent to Control 1: 1 point

[0087] The results of the sensory evaluation of the lemon - flavored beverages of Invention Products 1 - 1 to 1 - 47 and Comparative Products 1 - 1 to 1 - 6 are shown in Table 2 below.

[0088]

Table 2

[0089] As shown in Table 2, it was confirmed that the lemon - flavored beverages (Invention Products 1 - 1 to 1 - 47) to which the compounds of Group A, Group B, and Group C were added had an alcoholic sensation imparted compared to the lemon - flavored beverage without these compounds (Control 1). On the other hand, when none of the compounds of Group A, Group B, and Group C were added (Comparative Products 1 - 1 to 1 - 3), or when the concentrations of the compounds of Group A, Group B, and Group C were not within specific ranges respectively (Comparative Products 1 - 4 to 1 - 6), it was confirmed that no alcoholic sensation was imparted.

[0090] In Example 1, a lemon - flavored beverage stock solution was prepared using a basic lemon flavor, and then a propylene glycol solution of the compounds of Group A, Group B, and Group C was added to the lemon - flavored beverage stock solution to prepare the lemon beverage of the invention product. However, for example, a propylene glycol solution of the compounds of Group A, Group B, and Group C may be added to the basic lemon flavor to prepare a lemon flavor of the invention product containing the compounds of Group A, Group B, and Group C at a predetermined concentration, and this may be added to an arbitrary substrate to prepare the lemon - flavored beverage of the invention product. The inventors have confirmed that the lemon - flavored beverage prepared in this way has no difference in the flavor containing an alcoholic sensation compared to the lemon - flavored beverage of Example 1.

[0091] [Example 2] Additive Effect on Lemon-Flavored Alcoholic Beverages When preparing the lemon-flavored beverage stock solution of Example 1, part of the ion-exchanged water was replaced with commercially available shochu of the first category to prepare a lemon-flavored alcoholic beverage stock solution with an alcohol content of 5% (hereinafter referred to as "lemon-flavored alcoholic beverage stock solution (5%)") and a lemon-flavored alcoholic beverage stock solution with an alcohol content of 7% (hereinafter referred to as "lemon-flavored alcoholic beverage stock solution (7%)").

[0092] Propylene glycol solutions of the compounds in Group A, Group B, and Group C were added to this lemon-flavored alcoholic beverage stock solution (5%) so that the compounds in Group A, Group B, and Group C would have the respective concentrations corresponding to the Invention Products 2-1 to 2-47 in Table 3 below to prepare each preparation solution. After each preparation solution was put into a can, carbon dioxide gas was added so as to be 2.0 kg / cm 2 and sealed with a can seamer (winder). After the central temperature of the can reached 65°C in warm water, it was maintained at 65°C for 10 minutes for sterilization, and then cooled with cold water to produce lemon-flavored alcoholic beverages of the Invention Products 2-1 to 2-47. Similarly, propylene glycol solutions of the compounds in Group A, Group B, and Group C were added to this lemon-flavored alcoholic beverage stock solution (5%) so that the compounds in Group A, Group B, and Group C would have the respective concentrations corresponding to the Comparative Products 2-1 to 2-6 in Table 3 below to prepare each preparation solution, and through the same process, lemon-flavored alcoholic beverages of the Comparative Products 2-1 to 2-6 were produced. Further, a lemon-flavored beverage (alcohol content 5%) produced in the same process except that the propylene glycol solutions of the compounds in Group A, Group B, and Group C were not added to the lemon-flavored alcoholic beverage stock solution (5%) was used as the lemon-flavored alcoholic beverage of Control Product 2-1. Also, a lemon-flavored beverage (alcohol content 7%) produced in the same process except that the propylene glycol solutions of the compounds in Group A, Group B, and Group C were not added to the lemon-flavored alcoholic beverage stock solution (7%) was used as the lemon-flavored alcoholic beverage of Control Product 2-2.

[0093] Then, for the lemon-flavored alcoholic beverages of the obtained Invention Products 2-1 to 2-47 and Comparative Products 2-1 to 2-6, sensory evaluations were conducted by 15 well-trained panelists (with more than 10 years of experience). The sensory evaluations were carried out by asking the panelists to comment on the differences in flavor when comparing Invention Products 2-1 to 2-47 and Comparative Products 2-1 to 2-6 with an alcohol content of 5% with Control Product 2-1, and averaging the scores given by the panelists to the alcohol feeling (as defined above) compared with Control Product 2-1 according to the following evaluation criteria. Furthermore, for the lemon-flavored alcoholic beverages of Invention Products 2-1 to 2-47 and Comparative Products 2-1 to 2-6 with an alcohol content of 5%, sensory evaluations were also carried out by averaging the scores given by the panelists to the alcohol feeling compared with Control Product 2-2 with an alcohol content of 7% according to the following evaluation criteria.

[0094] <Evaluation Criteria for Alcohol Feeling (vs 5%)> Significantly increased compared to Control Product 2-1: 5 points Greatly increased compared to Control Product 2-1: 4 points Somewhat increased compared to Control Product 2-1: 3 points Slightly increased compared to Control Product 2-1: 2 points Equivalent to Control Product 2-1: 1 point

[0095] <Evaluation Criteria for Alcohol Feeling (vs 7%)> Superior to Control Product 2-2: 5 points Equivalent to Control Product 2-2: 4 points Slightly inferior to Control Product 2-2: 3 points Greatly inferior to Control Product 2-2: 2 points Significantly inferior to Control Product 2-2: 1 point

[0096] The results of the sensory evaluations are shown in Table 3 below.

[0097]

Table 3

[0098] As shown in Table 3, it was confirmed that the lemon - flavored alcoholic beverages (Inventive Products 2 - 1 to 2 - 47) to which the compounds of Group A, Group B, and Group C were added had an enhanced alcohol feeling compared to the lemon - flavored alcoholic beverage (5%; Control Product 2 - 1) without these compounds. Also, the lemon - flavored alcoholic beverages (Inventive Products 2 - 1 to 2 - 47) to which the compounds of Group A, Group B, and Group C were added had no inferior alcohol feeling even when compared to the lemon - flavored alcoholic beverage (7%; Control Product 2 - 2) without these compounds, and it was also confirmed that the difference in the actual alcohol concentration could be compensated for by the present invention. On the other hand, when none of the compounds of Group A, Group B, and Group C were added (Comparative Products 2 - 1 to 2 - 3), or when the concentrations of the compounds of Group A, Group B, and Group C were not within specific ranges respectively (Comparative Products 2 - 4 to 2 - 6), it was confirmed that the alcohol feeling was not enhanced.

[0099] In Example 2, a lemon - flavored alcoholic beverage stock solution was prepared using a basic lemon flavor, and then a propylene glycol solution of the compounds of Group A, Group B, and Group C was added to the lemon - flavored alcoholic beverage stock solution to prepare the lemon - flavored alcoholic beverage of the present invention. However, for example, a propylene glycol solution of the compounds of Group A, Group B, and Group C may be added to the basic lemon flavor to prepare a lemon flavor of the present invention containing the compounds of Group A, Group B, and Group C at a predetermined concentration, and this may be added to an arbitrary base material to prepare the lemon - flavored alcoholic beverage of the present invention. The inventors have confirmed that the lemon - flavored alcoholic beverage prepared in this way has no difference in the flavor including the alcohol feeling compared to the lemon - flavored alcoholic beverage of Example 2.

[0100] [Example 3] Addition effect on beer - taste completely non - alcoholic beverage To a commercially available beer-flavored beverage (alcohol content: 0.00%), propylene glycol solutions of the compounds of Group A, Group B, and Group C were added so that the concentrations of the compounds corresponded to those of the inventive products 3-1 to 3-36 in Table 4 below, and beer-flavored beverages of the inventive products 3-1 to 3-36 were prepared. On the other hand, the above-mentioned commercially available beer-flavored beverage to which the propylene glycol solutions of the compounds of Group A, Group B, and Group C were not added was used as Control 3.

[0101] Then, sensory evaluations of the obtained beer-flavored beverages of the inventive products 3-1 to 3-36 were performed by 15 well-trained panelists (with 10 or more years of experience). The sensory evaluations were conducted by having the panelists comment on the difference in flavor when the inventive products 3-1 to 3-36 were compared with Control 3, and averaging the scores given by the panelists to the alcohol sensation (as defined above) compared with Control 3 according to the following evaluation criteria.

[0102] [Evaluation Criteria for Alcohol Sensation] Significantly increased compared to Control 3: 5 points Greatly increased compared to Control 3: 4 points Somewhat increased compared to Control 3: 3 points Slightly increased compared to Control 3: 2 points Equivalent to Control 3: 1 point

[0103] The results of the sensory evaluations of the beer-flavored beverages of the inventive products 3-1 to 3-36 are shown in Table 4 below.

[0104] [Table 4]

[0105] As shown in Table 4, it was confirmed that the beer-flavored beverages to which the compounds of Group A, Group B, and Group C were added were imparted with an alcohol sensation compared to the beer-flavored beverages without these compounds added.

[0106] [Example 4] Addition Effect on Beer To commercially available beer (alcohol content 5%), propylene glycol solutions of the compounds of Group A, Group B, and Group C were added so that the concentrations of the compounds of Group A, Group B, and Group C corresponded to the respective concentrations of the Invention Products 4-1 to 4-36 in Table 5 below, and the beer of the Invention Products 4-1 to 4-36 was prepared. On the other hand, the above commercially available beer to which the propylene glycol solutions of the compounds of Group A, Group B, and Group C were not added was used as Control Product 4.

[0107] Then, sensory evaluation of the obtained beer of the Invention Products 4-1 to 4-36 was carried out by 15 well-trained panelists (with more than 10 years of experience). The sensory evaluation was conducted by having the panelists comment on the difference in flavor when the Invention Products 4-1 to 4-36 were compared with Control Product 4, and averaging the scores given by the panelists according to the following evaluation criteria for the alcohol feeling (the definition is as described above) compared with Control Product 4.

[0108] <Evaluation Criteria for Alcohol Feeling> Significantly increased compared to Control Product 4: 5 points Greatly increased compared to Control Product 4: 4 points Somewhat increased compared to Control Product 4: 3 points Slightly increased compared to Control Product 4: 2 points Equivalent to Control Product 4: 1 point

[0109] The results of the sensory evaluation of the beer of the Invention Products 4-1 to 4-36 are shown in Table 5 below.

[0110]

Table 5

[0111] As shown in Table 5, it was confirmed that the beer to which the compounds of Group A, Group B, and Group C were added had an enhanced alcohol feeling compared to the beer without these compounds added.

[0112] [Example 5] Addition Effect on Highball To commercially available highballs (alcohol content: 7%, raw materials: whiskey, carbonated water), propylene glycol solutions of the compounds of Group A, Group B, and Group C were added so that the concentrations of the compounds of Group A, Group B, and Group C corresponded to the respective concentrations of the inventive products 5-1 to 5-36 in Table 6 below, and highballs of the inventive products 5-1 to 5-36 were prepared. On the other hand, the above commercially available highballs to which the propylene glycol solutions of the compounds of Group A, Group B, and Group C were not added were used as Control 5.

[0113] Then, sensory evaluations of the obtained highballs of the inventive products 5-1 to 5-36 were performed by 15 well-trained panelists (with more than 10 years of experience). The sensory evaluation was carried out by having the panelists comment on the difference in flavor when the inventive products 5-1 to 5-36 were compared with Control 5, and by averaging the scores given by the panelists to the alcohol feeling (defined as described above) compared with Control 5 according to the following evaluation criteria.

[0114] <Evaluation Criteria for Alcohol Feeling> Significantly increased compared to Control 5: 5 points Greatly increased compared to Control 5: 4 points Somewhat increased compared to Control 5: 3 points Slightly increased compared to Control 5: 2 points Equivalent to Control 5: 1 point

[0115] The results of the sensory evaluations of the highballs of the inventive products 5-1 to 5-36 are shown in Table 6 below.

[0116]

Table 6

[0117] As shown in Table 6, it was confirmed that the highballs to which the compounds of Group A, Group B, and Group C were added had an enhanced alcohol feeling compared to the highballs without these compounds.

[0118] [Example 6] Addition Effect on Sangria (Wine-Flavored Beverage) To a commercially available sangria (alcohol content 6%, raw materials: red wine, orange juice, raspberry juice), propylene glycol solutions of the compounds of Group A, Group B, and Group C were added so that the concentrations of the compounds of Group A, Group B, and Group C corresponded to the respective concentrations of the Invention Products 6-1 to 6-36 in Table 7 below, and the sangrias of the Invention Products 6-1 to 6-36 were prepared. On the other hand, the above commercially available sangria to which the propylene glycol solutions of the compounds of Group A, Group B, and Group C were not added was used as Control Product 6.

[0119] Then, sensory evaluations of the obtained sangrias of the Invention Products 6-1 to 6-36 were performed by 15 well-trained panelists (with 10 or more years of experience). The sensory evaluation was conducted by asking the panelists to comment on the difference in flavor when the Invention Products 6-1 to 6-36 were compared with Control Product 6, and averaging the scores given by the panelists according to the following evaluation criteria for the alcohol feeling (as defined above) when compared with Control Product 6.

[0120] <Evaluation Criteria for Alcohol Feeling> Significantly increased compared to Control Product 6: 5 points Greatly increased compared to Control Product 6: 4 points Somewhat increased compared to Control Product 6: 3 points Slightly increased compared to Control Product 6: 2 points Equivalent to Control Product 6: 1 point

[0121] The results of the sensory evaluations of the sangrias of the Invention Products 6-1 to 6-36 are shown in Table 7 below.

[0122]

Table 7

[0123] As shown in Table 7, it was confirmed that the sangrias to which the compounds of Group A, Group B, and Group C were added had an enhanced alcohol feeling compared to the sangrias without these compounds.

[0124] [Example 7] Additive Effect on White Wine To commercially available white wine (alcohol content 10%), propylene glycol solutions of the compounds in Group A, Group B, and Group C were added so that the concentrations of the compounds in Group A, Group B, and Group C corresponded to the respective concentrations of the Invention Products 7-1 to 7-36 in Table 8 below, and white wines of the Invention Products 7-1 to 7-36 were prepared. On the other hand, the above commercially available white wine to which the propylene glycol solutions of the compounds in Group A, Group B, and Group C were not added was used as Control Product 7.

[0125] Then, sensory evaluations of the obtained white wines of the Invention Products 7-1 to 7-36 were conducted by 15 well-trained panelists (with more than 10 years of experience). The sensory evaluation was performed by asking the panelists to comment on the difference in aroma when the Invention Products 7-1 to 7-36 were compared with Control Product 7, and averaging the scores given by the panelists according to the following evaluation criteria for the alcohol feeling (the definition is as described above) when compared with Control Product 7.

[0126] <Evaluation Criteria for Alcohol Feeling> Significantly increased compared to Control Product 7: 5 points Greatly increased compared to Control Product 7: 4 points Somewhat increased compared to Control Product 7: 3 points Slightly increased compared to Control Product 7: 2 points Equivalent to Control Product 7: 1 point

[0127] The results of the sensory evaluations of the white wines of the Invention Products 7-1 to 7-36 are shown in Table 8 below.

[0128]

Table 8

[0129] As shown in Table 8, it was confirmed that the white wines to which the compounds in Group A, Group B, and Group C were added had an enhanced alcohol feeling compared to the white wine without these compounds.

[0130] [Example 8] Additive Effect on Chocolate Commercially available chocolate (alcohol content 0.00%) was melted once by soaking in hot water. To the melted chocolate, MCT (medium-chain triglyceride, a neutral fat composed of fatty acids with 8 to 12 carbon atoms) solutions (1% - 10 ppm) of the compounds in Group A, Group B, and Group C were added so that each concentration corresponded to the Invention Products 8-1 to 8-36 in Table 9 below. After adding, it was cooled again to solidify, thereby preparing the chocolates of Invention Products 8-1 to 8-36. On the other hand, the above-mentioned commercially available chocolate without the addition of the MCT solutions of the compounds in Group A, Group B, and Group C was used as Control 8.

[0131] Then, sensory evaluations of the obtained chocolates of Invention Products 8-1 to 8-36 were conducted by 15 well-trained panelists (with more than 10 years of experience). For the sensory evaluation, the panelists were asked to comment on the difference in flavor when comparing Invention Products 8-1 to 8-36 with Control 8, and the panelists scored the alcohol feeling (as defined above) when compared with Control 8 according to the following evaluation criteria, and the average value was taken.

[0132] <Evaluation Criteria for Alcohol Feeling> Significantly increased compared to Control 8: 5 points Greatly increased compared to Control 8: 4 points Somewhat increased compared to Control 8: 3 points Slightly increased compared to Control 8: 2 points Equivalent to Control 8: 1 point

[0133] The results of the sensory evaluations of the chocolates of Invention Products 8-1 to 8-36 are shown in Table 9 below.

[0134]

Table 9

[0135] As shown in Table 9, it was confirmed that the chocolates added with the compounds of Group A, Group B, and Group C were imparted with an alcoholic feeling as compared with the chocolates without these compounds added.

Claims

1. An alcohol flavor improving agent comprising a compound of Group A below, one or more compounds selected from Group B below, and one or more compounds selected from Group C below. (Group A) 2-(3-benzyloxypropyl)pyridine (Group B) 4-menthyloxy-2-butanone, 2-methyl-4-menthyloxy-2-butanol (Group C) 3-(4-ethoxyphenyl)prop-2-enal, 3-(4-propoxyphenyl)prop-2-enal, 3-(4-isopropoxyphenyl)prop-2-enal, 3-(4-(2-propenyloxy)phenyl)prop-2-enal, 3-(4-butoxyphenyl)prop-2-enal, 3-(4-isobutoxyphenyl)prop-2-enal, 3-(4-(sec-butoxy)phenyl)prop-2-enal, 3-(4-(tert-butoxy)phenyl)prop-2-enal, 3-(4-(3-butenyloxy)phenyl)prop-2-enal

2. An alcohol flavor improving composition containing, as active ingredients, a compound of Group A below, one or more compounds selected from Group B below, and one or more compounds selected from Group C below. (Group A) 2-(3-benzyloxypropyl)pyridine (Group B) 4-menthyloxy-2-butanone, 2-methyl-4-menthyloxy-2-butanol (Group C) 3-(4-ethoxyphenyl)prop-2-enal, 3-(4-propoxyphenyl)prop-2-enal, 3-(4-isopropoxyphenyl)prop-2-enal, 3-(4-(2-propenyloxy)phenyl)prop-2-enal, 3-(4-butoxyphenyl)prop-2-enal, 3-(4-isobutoxyphenyl)prop-2-enal, 3-(4-(sec-butoxy)phenyl)prop-2-enal, 3-(4-(tert-butoxy)phenyl)prop-2-enal, 3-(4-(3-butenyloxy)phenyl)prop-2-enal

3. A food or drink product comprising the alcohol feeling improving agent according to claim 1 or the alcohol feeling improving composition according to claim 2.

4. In the food or drink product according to claim 3, Based on the total mass of the food or drink product, the concentration of the compounds in Group A is in the range of 0.03 ppm or more and 3 ppm or less, the concentration of the compounds in Group B is in the range of 0.05 ppm or more and 10 ppm or less, and the concentration of the compounds in Group C is in the range of 0.1 ppm or more and 10 ppm or less. A food or drink product.

5. A method for improving the alcohol feeling of a food or drink product, comprising the step of adding the alcohol feeling improving agent according to claim 1 or the alcohol feeling improving composition according to claim 2 to the food or drink product.

6. In the method for improving the alcohol feeling of the food or drink product according to claim 5, In the above step, based on the total mass of the food or drink product, the concentration of the compounds in Group A is in the range of 0.03 ppm or more and 3 ppm or less, the concentration of the compounds in Group B is in the range of 0.05 ppm or more and 10 ppm or less, and the concentration of the compounds in Group C is in the range of 0.1 ppm or more and 10 ppm or less. A method for improving the alcohol feeling of a food or drink product, wherein the alcohol feeling improving agent or the alcohol feeling improving composition is added to the food or drink product.

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