WO2023276505A1

WO2023276505A1 - Flavor imparting composition including disulfide compound

Info

Publication number: WO2023276505A1
Application number: PCT/JP2022/021592
Authority: WO
Inventors: 康大福井; 康隆大久保; 詩歩長谷川
Original assignee: 長谷川香料株式会社
Priority date: 2021-06-30
Filing date: 2022-05-26
Publication date: 2023-01-05
Also published as: JP2022104508A

Abstract

Provided is a flavor imparting composition including a disulfide compound that is represented by formula (1). In addition to imparting a flavor, the flavor imparting composition may also have an effect of strengthening a carbonation sensation. The present invention can further provide a consumer good including the flavor imparting composition, a method for imparting a flavor to a consumer good, said method including adding the flavor imparting composition to the consumer good, and a method for imparting a flavor to a flavor imparting composition, said method including adding the aforementioned flavor imparting composition to another flavor imparting composition.

Description

Flavoring composition containing a disulfide compound

The present invention relates to a flavoring composition containing a disulfide compound.

　In recent years, consumer demands for food, beverages and cosmetics have become more sophisticated and diversified, but in particular, attention has been focused on fragrance, and the characteristics of fragrance have become an important factor in the appeal of products. For example, there is an increasing demand for a compound that, when added to an article, can impart a characteristic flavor such as long-lasting and natural flavor to the article.

Some sulfur-containing compounds (those containing sulfur atoms in the molecule) are known for use in flavoring, examples being 1,2-ethanedithiol, 2,3-butanedithiol, 1,6 - The use of alkanedithiols such as hexanedithiol for imparting flavor such as cooked meat (Patent Document 1), and the addition of dimethyltrisulfide to vanilla flavor to achieve the natural feeling of vanilla, the luxurious feeling of vanilla, and vanilla extract. improving the feeling of freshly brewed coffee (Patent Document 2), by combining sulfur-containing compounds such as 3-mercapto-3-methylbutyl acetate, 2-furfurylmethyl sulfide, and 2-furfurylmethyl disulfide. There is known a document describing giving (Patent Document 3).

JP-A-50-12277 JP 2018-115241 A JP 2008-259472 A

However, the sulfur-containing compounds that have been conventionally used for imparting flavor are monotonous in terms of flavor quality and intensity, the flavor that can be used is limited, and the desired characteristics cannot be imparted to the flavor. For two reasons, it has not been possible to sufficiently meet the diverse demands of consumers for the flavor of articles, and the discovery of new sulfur-containing compounds useful for imparting flavor has been an issue. Accordingly, it is an object of the present invention to provide a flavor imparting composition containing a sulfur-containing compound that is useful for imparting flavor to articles.

The inventors of the present invention have made intensive research in view of the above problems, and found that the compound represented by the following formula (1), which was not known for its use in imparting flavor and had no known scent per se, imparts flavor. The inventors have found that it is useful for the present invention.

Thus, a brief outline of representative inventions among the inventions disclosed in the present application is as follows.
[1] A flavor imparting composition containing a disulfide compound represented by the following formula (1).

[2] The flavor-imparting composition according to [1], wherein the flavor-imparting composition has the effect of imparting a carbonic acid sensation in addition to imparting flavor.
[3] A consumer product comprising the flavoring composition of [1] or [2].
[4] A method for imparting flavor to consumer goods, comprising adding the flavor imparting composition of [1] or [2] to the consumer goods.
[5] A method for imparting flavor to a flavor-imparting composition, comprising adding the flavor-imparting composition according to [1] or [2] to another flavor-imparting composition.

The present invention has made it possible to provide a flavor imparting composition that can be used to impart flavor to various articles.

The present invention will be described in more detail below with specific examples. In the present specification, "to" means a range including lower and upper limits, concentrations (ppt, ppb, ppm, etc.), % represents mass concentration and mass%, respectively, unless otherwise specified. Final concentration unless otherwise specified.

[Flavor imparting composition containing disulfide compound represented by formula (1)]
In the present invention, the disulfide compound represented by the following formula (1) contained in the flavor-imparting composition (in this specification, it may be simply referred to as the compound of formula (1)) has been known to have a scent. It was not known at all that this compound could be used to impart flavor to consumer goods, and the inventors of the present invention confirmed for the first time its usefulness in flavor imparting applications.

Although the means for obtaining the compound of formula (1) is not particularly limited, it can be synthesized, for example, by the following general method.

A known general synthesis of asymmetric disulfides can be applied to the synthesis of the compound of formula (1). That is, an alkyl halide is reacted with a thiosulfate to obtain an alkylthiosulfate (Bunte salt), which is further reacted with an alkanethiolate to obtain an asymmetric disulfide. As a specific example, the synthesis method according to the following reaction route (A) or reaction route (B) can be exemplified, but (A) is preferable in consideration of the availability of raw materials.

In the reaction pathways (A) and (B), in the first reaction, X in the starting compound (a1) represents a halogen atom and may be, for example, chlorine or bromine. M in compound (a2) and compound (a3) represents an alkali metal and may be, for example, sodium or potassium. Also, compound (a2) may be a hydrate, for example, a pentahydrate. The amount of compound (a2) used may be 1 to 1.5 equivalents, preferably 1.2 to 1.3 equivalents, relative to compound (a1). The solvent used can be water, methanol, or a mixture thereof for compound (a2), and various solvents can be used for compound (a1). When the reaction is carried out in a two-phase system using a solvent immiscible with the solvent used for dissolving compound (a2) in the first reaction, it is preferable to use a phase transfer catalyst such as a quaternary ammonium salt in combination. Preferred examples of the phase transfer catalyst to be used include, but are not limited to, tetra(n-butyl)ammonium bromide, benzyltriethylammonium chloride, methyltri(n-octyl)ammonium chloride and the like. The reaction temperature may range from 0 to 100°C, preferably from 20 to 60°C.

In the second reaction, the solvent used is preferably water or methanol. M in compound (a4) represents an alkali metal and may be, for example, sodium or potassium. The amount of compound (a4) to be used is in the range of 0.3 to 0.8 equivalents, particularly 0.3 to 0.5 equivalents, relative to compound (a3), since excessive use promotes the disproportionation described below. Use within the range of equivalents is preferred. Since the resulting compound of formula (1) gradually disproportionates to the symmetrical disulfide in alkaline solution, the second reaction is carried out for 10 to 30 minutes at 0° C. to 20° C., followed immediately by a hydrocarbon solvent. It is preferred to extract the product. Alternatively, a hydrocarbon solvent which is immiscible with water or methanol may coexist in the reaction solution to react as a two-phase system, and the hydrocarbon solvent may be immediately separated. Preferred examples of the hydrocarbon solvent used include petroleum ether, n-pentane and n-hexane.

The compound of formula (1) itself exhibits characteristic aromas including aromas such as onion-like, garlic-like, tropical fruit-like, and roasted aromas, and can be added to various consumer goods to impart flavor to the object of addition. There are no particular restrictions on the articles to which the additives are added, but examples include flavor-imparting compositions (details will be described later), and consumer goods such as food and beverages, cosmetics, and health and hygiene products.

As used herein, the term "flavor" means one or more senses that can be changed by scent, typically including the sense of smell and/or taste. As used herein, "flavoring" includes adding and enhancing flavor. For example, the flavor may be improved as a result of "flavoring". Moreover, in this specification, the flavor of food and drink may be called flavor. Furthermore, as a result of imparting flavor, sensations other than olfactory and/or gustatory sensations, such as cold sensation, warm sensation, texture (such as throat, hardness, viscosity, etc., also referred to as texture), carbonic acid sensation, and stimulation such as hotness. It may enhance, suppress, or improve a feeling, etc. As used herein, "addition" includes at least one of simply adding to a certain object by spraying, dropping, etc., and mixing with a certain object.

[Flavor imparting composition]
A flavor-imparting composition according to one embodiment of the present invention (herein referred to simply as the flavor-imparting composition of the present invention) contains a predetermined amount of the compound of formula (1), and is suitable for various consumer goods. It can be added to flavor the consumable. Representative examples of the flavor-imparting composition of the present invention include flavoring compositions that can be added to various consumer goods such as food and drink, cosmetics, and medical hygiene products. , fermented products of various animal and plant materials, and the like, but are not limited to these.

In addition to the compound of formula (1), the flavor-imparting composition of the present invention includes optional components (specifically Examples are given below), but may consist essentially of the compound of formula (1). When the flavor-imparting composition of the present invention also contains components other than the compound of formula (1), the concentration of the compound of formula (1) in the flavor-imparting composition depends on the addition target and aroma characteristics of the flavor-imparting composition. can be determined arbitrarily.

As an example of the concentration of the compound of formula (1) in the flavor-imparting composition of the present invention, the flavor-imparting composition of the present invention may contain components other than the compound of formula (1) and its solvent or dispersion medium (specific examples will be described later). When it does not substantially contain, the range of 0.1% to 99.9% can be exemplified. Preferred examples are 1% to 99.9%, 10% to 99.9%, 20% to 99.9%, 50% to 99.9%, 70% to 99.9%, 80% to 99.9% , 90%-99.9%, 95%-99.9%, and 99%-99.9%.

As an example of the concentration of the compound of formula (1) in the flavoring composition of the present invention, in particular, the flavoring composition of the present invention contains a flavorable ingredient other than the compound of formula (1) and its solvent or dispersion medium. When it is contained, the concentration of the compound of formula (1) in the flavor-imparting composition can be arbitrarily determined according to the addition target and aroma characteristics of the flavor-imparting composition. 10ppt to 10%, preferably 100ppt to 1%, more preferably 1ppb to 0.1%. More specifically, the lower limit is 10ppt, 100ppt, 1ppb, 10ppb, 100ppb, 1ppm, 10ppm, 100ppm, 0.1%, or 1%, and the upper limit is 10%, 1%, 0.1%. , 100 ppm, 10 ppm, 1 ppm, 100 ppb, 10 ppb, 1 ppb, 100 ppt, and any combination of these lower and upper limits. Although it depends on the formulation and fragrance tone of the flavor-imparting composition, when the concentration of the compound of formula (1) in the flavor-imparting composition is 10 ppt to 10%, the aroma derived from the compound of formula (1) is excessive. You can feel the effect of adding flavor to consumer goods without sticking out. The compound of formula (1) may be added at a concentration outside the range of 10 ppt to 10% depending on the flavor of the flavor imparting composition.

In addition to the compound of formula (1), the flavor imparting composition of the present invention may further contain other optional flavor imparting ingredients or other auxiliary ingredients, such as various kinds of flavor compounds, fragrance compositions, oils Soluble pigments, vitamins, functional substances, fish 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 and the like can be exemplified. For example, "Patent Office Gazette, Collection of Well-known and Commonly Used Techniques (Fragrance) Part II Food Flavors, Issued on January 14, 2000", "Survey on the Usage of Food Flavoring Compounds in Japan" (2000 Welfare Science Research Report, Japan Perfume Manufacturers Association, March 2001), and "Synthetic Perfume Chemistry and Product Knowledge" (December 20, 2016, revised edition, Synthetic Perfume Editorial Committee, Chemical Daily) natural essential oils, natural fragrances, synthetic fragrances, and the like.

Other examples of fragrance compounds include hydrocarbon compounds such as monoterpenes such as α-pinene, β-pinene, myrcene, camphene and limonene; sesquiterpenes such as valencene, cedrene, caryophyllene and longifolene; and undecatriene.

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

Aldehyde compounds include saturated or unsaturated aldehydes such as acetaldehyde, hexanal, octanal, decanal, (E)-2-hexenal, and 2,4-octadienal, citronellal, hydroxycitronellal, citral, myrtenal, perillaldehyde, and the like. aromatic aldehydes such as terpenealdehyde, benzaldehyde, cinnamaldehyde, amylcinnamaldehyde, vanillin, ethylvanillin, heliotropine, and p-tolylaldehyde.

Ketone compounds include saturated or unsaturated ketones such as 2-heptanone, 2-undecanone, 1-octen-3-one, acetoin, diacetyl, 2,3-pentanedione, maltol, ethyl maltol, cyclotene, 2,5- diketones and hydroxyketones such as dimethyl-4-hydroxy-3(2H)-furanone, terpene ketones such as carvone, menthone, nootkatone, ketones derived from terpene degradation products such as α-ionone, β-ionone, β-damascenone, Aromatic ketones such as raspberry ketones are included.

Furan or ether compounds include furfuryl alcohol, furfural, rose oxide, linalool oxide, menthofuran, theaspirane, estragole, eugenol, and 1,8-cineole.

Ester compounds include ethyl acetate, isoamyl acetate, ethyl butyrate, ethyl isobutyrate, isoamyl butyrate, ethyl 2-methylbutyrate, ethyl 3-methylbutyrate, 2-methylbutyl isobutyrate, ethyl hexanoate, allyl hexanoate, ethyl heptanoate. , ethyl caproate, isoamyl isovalerate, ethyl nonanoate, etc. Terpene alcohol esters, such as linalyl acetate, geranyl acetate, lavandulil acetate, terpenyl acetate, benzyl acetate, benzyl butyrate, methyl salicylate, benzyl salicylate, cinnamon aromatic esters such as methyl acid, cinnamyl propionate, ethyl benzoate, cinnamyl isovalerate, and ethyl 3-methyl-2-phenylglycidate;

The lactone compounds include saturated or unsaturated lactones such as γ-decen-4-olide, 2-decen-5-olide, γ-decen-4-olide, γ-dodecalactone, δ-decen-5-olide, and the like.

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

Nitrogen-containing compounds include indole, skatole, pyridine, alkyl-substituted pyrazine, methyl anthranilate, and trimethylpyrazine.

Sulfur-containing compounds include methanethiol, dimethylsulfide, dimethyldisulfide, allyl isothiocyanate, 3-methyl-2-butene-1-thiol, 3-methyl-2-butanethiol, 3-methyl-1-butanethiol, 2 -methyl-1-butanethiol, 2-methyl-3-butene-1-thiol, 3-methyl-2-butene-1-thiol, and furfuryl mercaptan.

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

Various animal and plant extracts include herb or spice extracts, coffee, green tea, black tea, or oolong tea extracts, milk or processed milk products, and their various enzymatic decomposition products such as lipase and/or protease.

The flavor imparting composition of the present invention can be prepared by adding the compound of formula (1) to an appropriate solvent or dispersion medium by a known method. Examples of the form of the flavor-imparting composition of the present invention include solutions in which the compound of formula (1) and other components are dissolved in a water-soluble or oil-soluble solvent, emulsified formulations, powder formulations, and other solid formulations (such as solid fats). preferable. Although there are no particular restrictions on the types of solvents and dispersion media to be used, for example, the following can be used.

Examples of water-soluble solvents include ethanol, methanol, acetone, tetrahydrofuran, acetonitrile, 2-propanol, methyl ethyl ketone, glycerin, ethylene glycol, propylene glycol, dipropylene glycol, hexyl glycol, benzyl benzoate, triethyl citrate, diethyl phthalate, and the like. can be exemplified. Among these, ethanol or propylene glycol is particularly preferable when used for food and drink. Oil-soluble solvents include vegetable oils, animal oils, refined oils (for example, processed oils such as medium-chain fatty acid triglycerides and short-chain fatty acid triglycerides such as triacetin and tripropionin), hakolin, various essential oils, and triethyl. Citrate and the like can be exemplified.

In addition, in order to prepare an emulsified formulation, it can be obtained by emulsifying the compound of formula (1) together with a water-soluble solvent and an emulsifier. The method for emulsifying the compound of formula (1) is not particularly limited, and various types of emulsifiers conventionally used in foods and beverages, such as fatty acid monoglycerides, fatty acid diglycerides, fatty acid triglycerides, propylene glycol fatty acid esters, Sucrose fatty acid ester, polyglycerin fatty acid ester, lecithin, modified starch, sorbitan fatty acid ester, quillaya extract, gum arabic, tragacanth gum, guar gum, karaya gum, xanthan gum, pectin, alginic acid and its salts, carrageenan, gelatin, casein, quillaya saponin A highly stable emulsion can be obtained by emulsifying with an emulsifier such as sodium caseinate using a homomixer, a colloid mill, a rotating disc type homogenizer, a high pressure homogenizer, or the like. The amount of these emulsifiers to be used is not strictly limited, and can be varied over a wide range depending on the type of emulsifier used. 01 to about 100 parts by weight, preferably about 0.1 to about 50 parts by weight. In order to stabilize the emulsification, such a water-soluble solvent liquid contains, in addition to water, polyhydric alcohols such as glycerin, propylene glycol, sorbitol, maltitol, sucrose, glucose, trehalose, sugar solution, and reduced starch syrup. One type or a mixture of two or more types can be added.

In addition, the emulsion obtained in this way can be made into a powder formulation by drying if desired. At the time of powderization, if necessary, sugars such as gum arabic, trehalose, dextrin, sugar, lactose, glucose, starch syrup, and reduced starch syrup can be added as appropriate. The amount of these agents to be used can be appropriately selected according to the desired properties of the powder formulation.

[Method for imparting flavor to other flavor imparting compositions]
As one aspect of the present invention, the flavoring composition of the present invention can also be added to another flavoring composition to impart flavor to the flavoring composition (herein, the other flavoring composition of the present invention). (sometimes referred to as a method for imparting flavor to a flavor imparting composition), whereby a new flavor imparting composition to which flavor is imparted can be produced. The new flavor-imparting composition produced by the method of imparting flavor to another flavor-imparting composition of the present invention can also be used as the flavor-imparting composition of the present invention for various consumer goods such as food and drink, cosmetics, and hygiene products. It can be used in manufacturing. In the production, the other flavor-imparting composition itself may be added to various consumer goods such as food and drink, cosmetics, and medical and sanitary products, or one or more water-soluble perfumes, emulsified flavor-imparting compositions may be added. Composition, arbitrary flavoring compound, natural essential oil (for example, the above-mentioned "Patent Office Gazette, Collection of Well-known and Commonly Used Techniques (Fragrance) Part II Food Flavoring", "Survey on the Use of Food Flavoring Compounds in Japan", and "Synthetic Flavors, fragrance compounds described in "Chemistry and Product Knowledge"), may be added to various consumer goods in combination with one or more selected from.

[Method for imparting flavor to consumer goods and consumer goods]
The flavor-imparting composition of the present invention containing the compound of formula (1) can be used by being added to various consumer goods such as food and drink, cosmetics, and hygiene products. Flavoring of various consumer goods produces flavored consumer goods. Therefore, in the present invention, the method for imparting flavor to various consumer goods can also be said to be a method for producing flavored consumer goods. The timing of addition of the flavor imparting composition to various consumer goods is arbitrary.

The food or drink to which the flavor-imparting composition containing the compound of formula (1) can be added is not particularly limited, and may have any flavor (also referred to as flavor). Examples of flavors include lemon, orange, and grapefruit. , lime, mandarin, mandarin orange, kabosu, sudachi, hassaku, iyokan, yuzu, shikuwasa, and kumquat; strawberry, blueberry, raspberry, apple, cherry, plum, apricot, peach, pineapple, banana, melon, mango, Various fruit flavors such as papaya, kiwi, pear, grape, muscat grape, kyoho grape, lychee, and passion fruit; milk flavors such as milk, yogurt, and butter; vanilla flavor; green tea, matcha, hojicha, black tea, oolong tea, pu-erh tea, herbal tea Various tea flavors such as; coffee flavor; cola flavor; cocoa flavor; cocoa flavor; various mint flavors such as spearmint and peppermint; , star anise, thyme, capsicum, nutmeg, basil, marjoram, rosemary, laurel, wasabi, Japanese pepper, and garlic; various nut flavors such as almonds, cashews, and walnuts; Various alcoholic beverage (alcohol) flavors such as whiskey, rum, gin, liqueur, sake, shochu, and beer; vegetable flavors such as carrots, tomatoes, cucumbers and onions; livestock flavors such as chicken, pork, beef, mutton and horse meat; seafood flavors broth (bouillon) flavor of vegetables, meat, seafood; consommé flavor; caramel flavor; That is, it may be a food or drink that makes you feel only one of the above flavors, or it may be a food or drink that makes you feel two or more flavors, and the plurality of flavors may be the same or different. Examples of fruit flavors include foods and drinks that make you feel multiple fruit flavors such as banana, peach and apple flavors (so-called mixed fruit flavors), and examples of the latter include citrus flavors such as lemon and milk flavors. products (such as citrus-flavored lactic acid bacteria beverages), and foods and drinks that give a mint flavor, citrus flavor, and cola flavor (such as mint- or lemon-flavored cola beverages). It can be any flavor that can be imparted.

Examples of suitable flavors of food and drink to which the flavor imparting composition of the present invention is added include various fruit flavors including citrus and soft fruits; coffee flavor; cocoa flavor; chocolate flavor; beer flavor; caramel flavor; various spices such as garlic and onion, or herb flavor; various tea flavors typified by black tea and green tea; milk flavor; and the like, but are not limited to these.

Furthermore, the flavor-imparting composition of the present invention can be suitably used to impart a salty taste to various foods and beverages by adding them to various foods and beverages that impart a salty taste. For example, by adding salty taste to various foods and drinks, it is possible to improve the satisfaction and flavor lingering of the foods and drinks, and to improve palatability. In particular, by adding a salty taste to low-salt food and drink, it is possible to achieve satisfaction and flavor that have been often lacking in low-salt food and drink due to substitute ingredients for sodium salts. It can improve the palatability of low-salt food and drink by improving the aftertaste.

More specific examples of food and drink include rice crackers, arare rice crackers, rice cakes, rice cakes, steamed buns, uiro, red bean paste, yokan, mizu yokan, kingyoku, jelly, castella, hard candy, biscuits, crackers, potato chips, cookies, Confectionery such as pie, pudding, ice cream, ice cream, butter cream, custard cream, cream puff, waffle, sponge cake, donut, chocolate, chewing gum, caramel, candy, peanut paste or other pastes; bread, udon, ramen , Chinese noodles, sushi, gomoku rice, fried rice, pilaf, gyoza skin, shumai skin, okonomiyaki, takoyaki, and other breads, noodles, rice, and other grains; , Miso-zuke, Takuan-zuke, and their pickle ingredients; , squid such as firefly squid, octopus such as common octopus and octopus, prawns such as prawns, botan prawns, spiny lobsters and black tigers, crabs such as king crabs, snow crabs, blue crabs and horse crabs, clams, clams, scallops, oysters, mussels Seafood such as shellfish, etc.; Livestock meat such as chicken, pork, beef, mutton, horse meat; Tempura, Curry, Stew, Beef Stew, Hayashi Rice Sauce, Meat Sauce, Mapo Tofu, Hamburg Steak, Dumplings, Kamameshi Mix, Soups (Corn Soup, Tomato Soup, Consomme Soup, etc.), Meatballs, Braised Kakuni, Canned Meat, Vegetables Boiled food, Chikuzen-ni, oden, hot pot, side dishes to take home, noodles such as ramen, soba, udon, and somen, soups used for these noodles, vegetable soups and other processed foods using animal and plant ingredients; table salt, seasoning salt, soy sauce, powder Soy sauce, miso, powdered miso, moromi, horseradish, furikake, ochazuke mix, margarine, mayonnaise, dressing, vinegar, sanbaizu, powdered sushi vinegar, Chinese mix, tempura soup, mentsuyu (kelp or bonito stock, etc.), sauce (medium) thick sauce, tomato sauce, etc.), ketchup, yakiniku sauce, curry roux, stew base, soup base, dashi stock (kelp or bonito stock, etc.), compound seasonings, new mirin, fried chicken powder, takoyaki powder, etc. Seasonings such as mixed flour, these seasonings are added Animal or plant-based dashi-flavored foods and drinks; cheese, yogurt, butter and other dairy products; apple, grape, and citrus fruits (grapefruit, orange, lemon, etc.) juice, pulp, grain, peel, etc. Fruit drinks; vegetables such as tomatoes, green peppers, celery, gourds, bitter melons, carrots, potatoes, asparagus, bracken, and fern, vegetable drinks containing these vegetables, vegetable-containing foods and drinks such as vegetable soups; coffee, cocoa, Green tea, black tea, oolong tea, soft drinks, carbonated drinks, cola drinks, lactic acid bacteria beverages, and other beverages; drinks containing herbal medicines and herbs; cola drinks, fruit juice drinks, milk drinks, sports drinks, honey drinks, vitamin supplement drinks, minerals Functional drinks such as replenishing drinks, energy drinks, nutrition drinks, and lactic acid beverages; non-alcoholic beverages such as alcohol-flavored beverages (beer flavor, plum wine flavor, chuhai flavor, etc.) (non-alcoholic beer, non-alcoholic chuhai) wine, shochu, awamori, sake, beer, chuhai, cocktail drinks, low-malt beer, fruit wine, spiced wine, so-called "third beer" beer-flavored beverages (also called beer-flavored beverages), and other brewing liquor (effervescent), liqueur (effervescent), or alcoholic beverages containing these;

Cosmetics to which the flavor-imparting composition of the present invention can be added are not particularly limited, but examples include perfumes such as eau de cologne, eau de toilette, eau de parfum, and parfum; Products: Cosmetics such as foundation, lipstick, lip balm, lip gloss, lotion, emulsion, cosmetic cream, cosmetic gel, essence, pack; antiperspirant spray, deodorant sheet, deodorant cream, deodorant stick, etc. Deodorant products; Inorganic salt-based, refreshing, carbon dioxide-based, skin-care, enzyme-based, herbal medicine-based bath agents; Suntan products, sunscreen products and other suntan cosmetics; , body soap, body soap, laundry soap, laundry detergent, disinfectant detergent, deodorant detergent, softener, kitchen detergent, cleaning detergent, and other health and hygiene detergents; toothpaste, tissue paper, toilet paper, etc. health and sanitary materials; fragrant products such as room and car deodorants and room fragrances; and the like. The usable flavor is not particularly limited, and may be any flavor that can be flavored by the flavor-imparting composition of the present invention. imparting one or more types of flavor), fruit aroma such as passion fruit and other soft fruits (especially imparting one or more types of ripeness, bitterness, or fruit juice), sweet and slightly burnt with fragrant nuances It can be suitably used for a bittersweet fragrance, for example, a fragrance reminiscent of caramel or baked goods. In addition, it may be used for floral tone, green tone, ozone tone, and the like.

In the present invention, the concentration of the compound of formula (1) in various consumer goods such as food, beverages, cosmetics, and medical and sanitary products to which the flavor-imparting composition of the present invention is added determines the degree of flavor and desired effect of the consumer goods. can be arbitrarily determined according to

As an example of the concentration, in the case of food and drink, the concentration of the compound of formula (1) is 0.01ppt to 100ppm, preferably 0.1ppt to 10ppm, more preferably 1ppt to 1ppm, relative to the total weight of the food and drink. Within the range of For example, the lower limit is 0.01ppt, 0.1ppt, 1ppt, 10ppt, 100ppt, 1ppb, 10ppb, 100ppb, 1ppm, or 10ppm, and the upper limit is 100ppm, 10ppm, 1ppm, 100ppb, 10ppb, 1ppb, 100ppt, 10ppt. , 1 ppt, or 0.1 ppt, within any combination of these lower and upper limits, but are not limited to these concentration ranges. Although it depends on the type and flavor of the food and drink, when the concentration of the compound of formula (1) in the food and drink is in the range of 0.01 ppt to 100 ppm, the aroma of the compound itself does not protrude excessively. Flavor can be imparted to food and drink to which it is added. Depending on the flavor characteristics of the food or drink to which it is added, the compound of formula (1) may be added at a concentration below the lower limit or above the upper limit.

In the case of cosmetics, the concentration of the compound of formula (1) may be in the range of 0.01 ppt to 1% with respect to the total weight of the cosmetics. More specifically, the lower limit is 0.01ppt, 0.1ppt, 1ppt, 10ppt, 100ppt, 1ppb, 10ppb, 100ppb, 1ppm, 10ppm, 100ppm, or 0.1%, and the upper limit is 1%, 0 .1%, 100 ppm, 10 ppm, 1 ppm, 100 ppb, 10 ppb, 1 ppb, 100 ppt, 10 ppt, 1 ppt, 0.1 ppt, including within any combination of these lower and upper limits, including but not limited to: Not limited. Examples of preferred concentrations include the concentration of the compound of formula (1) with respect to the total mass of the cosmetic, from each range of 100ppb to 100ppm, 1ppm to 100ppm, 1ppm to 0.1%, and 10ppm to 0.1% , can be selected according to the fragrance characteristics of cosmetics, but is not limited to these. Although it depends on the type and fragrance of the cosmetic product, when the concentration of the compound of formula (1) in the cosmetic product is 1 ppt to 1%, the aroma of the compound itself does not protrude excessively. can impart flavor to The compound of formula (1) may be added at a concentration below the lower limit or above the upper limit, depending on the fragrance characteristics of the cosmetic to which it is added.

The compound of formula (1) can impart a top flavor and/or a middle to last flavor to various products, and is particularly effective in imparting a middle to last flavor. For example, by adding an effective amount of the compound of formula (1) to foods, beverages, cosmetics, and other articles, natural feeling, freshness, and fruity feeling reminiscent of animal and plant materials used in foods, drinks, cosmetics, etc. , Flesh feeling, freshness, voluminousness (feeling that the taste has been enhanced with the scent, and the whole flavor is swelled), richness, meat feeling, aroma, etc. At least one of them is enhanced, It has a strong flavor and maintains a good balance. In particular, it is effective for imparting flavor from the middle to the last, and specifically, foods that use spices such as onions and garlic, and foods with roasted aroma (cocoa, coffee, alcoholic beverages that use barrels for their production, It is effective in imparting flavor to cooked meat, soup, curry, etc.), and even in the flavor of various fruits represented by citrus fruits and soft fruits, it has a particularly bitter flavor or a fruit flavor that includes a tropical fruit-like flavor. It is effective in imparting, and a natural feeling is imparted.

Furthermore, the flavor-imparting composition of the present invention can be added to various articles to impart flavor, and as a result, impart a carbonic acid sensation to the articles. For imparting a carbonic acid sensation, by adding a predetermined amount of the flavor-imparting composition of the present invention to various products containing carbonic acid, represented by beverages and confectionery, a flavor and/or stimulus caused by carbonic acid can be imparted to the product (this specification Carbonated sensation in the book) can be enhanced, and more specific examples of carbonic acid sensation include throat sensation and carbonic acid stimulus sensation. In this specification, the throat means the volume of the flavor felt when the swallowed beverage passes through the throat, and it includes complex movements such as muscle movement felt in the throat and resistance to swallowing. A sensation of carbonic acid stimulation means a sensation that includes a refreshing sensation such as the popping of carbonic acid. Carbonated alcoholic beverages, carbonated non-alcoholic beer-flavored beverages, carbonated soft drinks, and confectionery to which carbonic acidity is imparted (tablets, gum, etc.) It can be, but is not limited to. The concentration of the compound of formula (1) in food and drink can be adjusted in order to obtain the effect of imparting a carbonated sensation, and for example, the food and drink can be added at a relatively low concentration within the concentration range of 0.01 ppt to 100 ppm in the above-mentioned food and drink. By adding to, it is possible to sufficiently obtain the effect of imparting a carbonic acid feeling. An example of the concentration range in which the effect of imparting a carbonic acid feeling is easily obtained is 1 ppt to 1 ppb, preferably 10 ppt to 100 ppt. The lower limit is 1 ppt, 5 ppt, 10 ppt, 20 ppt, 50 ppt, 100 ppt, or 500 ppt, and the upper limit is 1 ppb, 500 ppt, 200 ppt, 100 ppt, 50 ppt, 20 ppt, or 10 ppt. It may be used at a concentration of less than 1 ppt or more than 1 ppb, depending on the desired degree of carbonation effect and the flavor of the food or drink to which it is added.

Hereinafter, the present invention will be described more specifically with reference to examples. In addition, this invention is not limited to these. Specifically, examples of methods for obtaining the compound of formula (1) to be contained in the flavor-imparting composition of the present invention and examples of addition of the flavor-imparting composition of the present invention to various articles are shown.

[Example 1] Synthesis of compound of formula (1) It was synthesized according to the following reaction route.

(First reaction) A starting material, alkenyl chloride compound (a1) (40.8 g, 390 mmol), toluene (95.2 g), ion-exchanged water (131 g), sodium thiosulfate pentahydrate (131 g), and sodium thiosulfate pentahydrate ( a2) (116 g, 468 mmol) and tetra(n-butyl)ammonium bromide (TBAB) (2.51 g, 7.80 mmol) were added and dissolved with stirring, and reacted at 20° C. for 3 hours with vigorous stirring. After confirming the consumption of (a1) by sampling the upper layer of the reaction liquid, the reaction liquid was transferred to a separating funnel to separate the lower layer, and the upper layer was discarded.

(Second reaction) The lower layer obtained in the first reaction was transferred to a 500 mL four-necked flask, and hexane (64.3 g) was added. A 20% aqueous solution of methyl mercaptan sodium salt (a4) (45.6 g, 130 mmol) was added at once at 20° C. with vigorous stirring. After vigorously stirring for 10 minutes, the reaction solution was transferred to a separatory funnel to separate the upper layer and discard the lower layer. The resulting upper layer was washed twice with 10% saline (80 g), and the solvent was distilled off using a rotary evaporator. The obtained crude product (12.4 g) was purified by vacuum distillation (bp 87° C./1.5 kPa) to obtain the compound of formula (1) (6.94 g, yield 36%, purity 98.4%). Obtained.

The physical property values of the obtained compound were as follows.
¹ H NMR (CDCl ₃ , 400 MHz) δ 1.71 (3H, s), 1.75 (3H, s), 2.41 (3H, s), 4.40 (2H, d, J = 8.0 Hz ), 5.29 (1H, tm, J=8.0 Hz).
¹³ C NMR (CDCl ₃ , 100 MHz) δ 17.9, 23.5, 25.8, 36.5, 119.3, 137.3.
IR (liquid film method, cm ⁻¹ ) 2976, 2914, 2856, 1667, 1438, 1376, 1306, 1209, 1103, 952, 843.
The obtained compound of formula (1) was evaluated for aroma. In the aroma evaluation, a 0.1% ethanol solution of the compound of formula (1) was prepared by mixing the compound of formula (1) with 95% ethanol, and five well-trained panelists with 10 years or more of experience were smelled. The subjects were asked to comment on the odors they sensed. As a result, onion-like, garlic-like, tropical fruit-like, and roast-like scents were mentioned as perceived scents. A 0.1% ethanol solution of the compound of formula (1) can be used as the flavor-imparting composition of the present invention by adding it to various articles as it is (Inventive product 1-1).

[Example 2] Example of addition to fruit flavor imparting composition According to the general formulation shown in Tables 1 to 3 below, a basic blended fragrance composition having a lemon-like scent and a basic blended fragrance composition having an orange-like scent and a basic perfume composition having a grape-like scent were prepared, respectively.

On the other hand, as the flavor-imparting composition of the present invention, an ethanol-diluted solution of the compound of formula (1) having an arbitrary concentration was prepared by mixing the compound of formula (1) with 95% ethanol (product of the present invention 2-1 ).

The product 2-1 of the present invention was added to each of the basic blended flavor compositions obtained so that the concentration of the compound of formula (1) was as shown in Table 4 below to give the flavor-imparting composition of the present invention. Perfume compositions of the present invention, which is one embodiment, were prepared (Inventive Products 2-2 to 2-22). In addition, allylmethyl disulfide, which belongs to sulfides, which are a type of sulfur-containing compound and is known as a fragrance compound, was selected as a comparative product, and added to each basic blended fragrance composition so that the concentration shown in Table 4 below was obtained. were prepared (comparative products 2-1 to 2-3). Ten well-trained panelists with 10 years or more of experience were asked to evaluate the aroma of the perfume composition of the present invention and the comparative product compared with the control product, using the basic blended perfume composition as a control product. In the evaluation, the subjects were asked to rate the natural feeling of the aroma according to the following criteria, and to freely comment on the aroma compared to the control product. Table 4 shows the average score and representative comments of the 10 panelists.
(Reference) “Greatly enhanced” = 4 points “Enhanced” = 3 points “Slightly enhanced” = 2 points “No enhancement” = 1 point The natural feeling means that the scent reminiscent of lemon fruit, orange fruit, or grape fruit is enhanced and has a natural scent like a real fruit.

As shown in Table 4, the compound of formula (1) is capable of imparting a good fragrance that gives a feeling of naturalness to fragrance compositions with various fruity fragrances, and it is possible to obtain a flavor-imparting effect that cannot be obtained with allylmethyl disulfide. was confirmed. In addition, it was confirmed that the compound of formula (1) exerts a flavor-imparting effect within the concentration range of at least 10 ppt to 10% in the fragrance composition, and exerts a particularly excellent effect within the concentration range of 1 ppb to 0.1%. . The fragrance compositions of Products 2-2 to 2-22 of the present invention obtained in the present examples are added to consumer goods such as food and drink, cosmetics, and hygiene products as the flavor-imparting composition of the present invention. It can be used to flavor consumer goods.

[Example 3] Examples of addition to fruit-flavored food and drink Commercially available lime juice, grapefruit juice, lemonade, kiwi juice, and lychee juice were prepared as fruit-flavored food and drink, and the present invention product 2-1 obtained in Example 2 ( Ethanol diluted solution of the compound of formula (1)) was added to each commercially available juice so that the concentration of the compound of formula (1) was as shown in Table 5 below to obtain the fruit-flavored beverage of the present invention. (Products 3-1 to 3-25 of the present invention). Ten well-trained panelists with 10 or more years of experience were asked to evaluate the flavor of the fruit-flavored beverage of the present invention, using each commercially available juice as a control. In the evaluation, the natural feeling of the fruit-flavored beverage of the present invention compared with the control product was scored according to the following criteria, and the subjects were asked to freely comment on the flavor of the product of the present invention compared with the control product. Table 5 shows the average score and typical comments of the 10 panelists.
(Reference) “Greatly enhanced” = 4 points “Enhanced” = 3 points “Slightly enhanced” = 2 points “No enhancement” = 1 point In addition, the natural feeling means that the flavor reminiscent of the fruit itself, which is the material of each commercially available fruit drink prepared, is enhanced, and it means the natural flavor as if the actual fruit was squeezed and added.

As shown in Table 5, it was confirmed that the compound of formula (1) can impart a good flavor that makes various fruit flavors feel natural. In addition, it was confirmed that the compound of formula (1) exerts a flavor-imparting effect in a fruit-flavored food and drink in a concentration range of at least 0.01 ppt to 100 ppm, and exerts a particularly excellent effect in a concentration range of 1 ppt to 1 ppm.

[Example 4] Example of addition to coffee-flavored food and drink To commercially available sugar-free coffee, present invention product 2-1 (an ethanol-diluted solution of the compound of formula (1)) obtained in Example 2 was added. 6 to obtain coffee-flavored beverages of the present invention (Products 4-1 to 4-3 of the present invention). In addition, allyl methyl disulfide was prepared as a comparative product and added to commercially available sugar-free coffee so that the concentration of the compound was as shown in Table 7 below to obtain a comparative coffee-flavored beverage (comparative product 4-1). . Then, using commercially available sugar-free coffee as a control product, the obtained coffee-flavored beverages of the present invention and the comparative product were asked to 10 well-trained panelists with 10 years or more of experience. They were asked to freely comment on the flavor of the comparative product. Table 6 shows representative comments from the ten panelists.

As shown in Table 6, the flavor-imparting composition of the present invention imparts flavor to coffee-flavored food and drink at a concentration range of at least the compound of formula (1) of 1 ppt to 1 ppm in the coffee-flavored food and drink, It was confirmed that the natural fragrance can be enhanced.

[Example 5] Examples of addition to various flavored beverages Commercially available carbonated muscat juice, non-alcoholic beer-taste beverages, and lemon-scented sugar-free carbonated water were prepared, and the product 2-1 of the present invention obtained in Example 2 (formula A diluted solution of the compound of formula (1) in ethanol) was added to each commercially available beverage so that the concentration of the compound of formula (1) was as shown in Table 7 below to obtain the beverage of the present invention (the present invention Articles 5-1 to 5-18). Ten well-trained panelists with 10 or more years of experience were asked to evaluate the flavor of the beverage of the present invention, using each commercially available beverage as a control. In the evaluation, the palatability of the flavor of the product of the present invention compared to the control product was scored according to the following criteria, and the subjects were asked to freely comment on the flavor of the product of the present invention compared to the control product. Palatability means feeling that something is delicious and makes you want to eat it. Table 7 shows the average scores and typical comments of the 10 panelists.
(Reference) “Greatly enhanced” = 4 points “Enhanced” = 3 points “Slightly enhanced” = 2 points “No enhancement” = 1 point for palatability compared to control product

As shown in Table 7, it was confirmed that the compound of formula (1) exerts a flavor-imparting effect at least within the concentration range of 1 ppt to 1 ppm in food and drink, and in particular, it exerts a particularly excellent effect in the range of 10 ppt to 10 ppb. was confirmed. It was also confirmed that the compound of formula (1) exerts a carbonic acid feeling enhancement effect in the range of 1 ppt to 1 ppb in addition to imparting flavor.

[Example 6] Examples of addition to chocolate- and cacao-flavored foods and beverages Commercially available chocolate drinks and cocoa beverages were prepared. Then, the product 2-1 of the present invention obtained in Example 2 (an ethanol-diluted solution of the compound of formula (1)) was added to a commercially available product so that the concentration of the compound of formula (1) was as shown in Table 8 below. They were added to chocolate drinks or cocoa drinks to obtain the chocolate drinks and cocoa drinks of the present invention (Products 6-1 to 6-8 of the present invention). Sensory evaluation was then performed on each of the beverages of the present invention using a commercially available product as a control product. In the evaluation, 10 well-trained panelists with 10 years or more of experience were asked to rate the richness of the product of the present invention compared to the control product according to the following criteria, and to evaluate the flavor of the product of the present invention compared to the control product. commented freely. Here, the full-bodied feeling means the feeling that the flavor is strong and mild, and the aftertaste of the flavor is fully felt after eating. Table 8 shows the average score and typical comments of the 10 panelists.
(Reference) “Greatly enhanced” = 4 points “Enhanced” = 3 points “Slightly enhanced” = 2 points “No enhancement” = 1 point for richness compared to the control product

As shown in Table 8, the flavor-imparting composition of the present invention imparts flavor to chocolate-flavored or cocoa-flavored food and drink at a concentration of at least the compound of formula (1) in the food and drink within the range of 1 ppt to 1 ppm. , As a representative example, it was confirmed that the richness can be enhanced.

[Example 7] Examples of addition to various alcoholic beverage-flavored foods and drinks Commercially available malt whiskey and red wine were prepared. The product 2-1 of the present invention obtained in Example 2 (an ethanol-diluted solution of the compound of formula (1)) was diluted with commercially available malt whiskey or By adding to red wine, alcoholic beverages of the present invention were obtained (Products 7-1 to 7-10 of the present invention). Sensory evaluation was performed on the alcohol-flavored beverage of the present invention using a commercially available product as a control product. In the evaluation, 10 well-trained panelists with 10 years or more of experience were asked to rate the maturity of the product of the present invention compared to the control product according to the following criteria, and to evaluate the flavor of the product of the present invention compared to the control product. commented freely. Here, the feeling of maturity means the feeling of richness and depth of flavor obtained through long-term change under appropriate storage conditions. Table 9 shows the average score and typical comments of the 10 panelists.
(Reference) “Greatly enhanced” = 4 points “Enhanced” = 3 points “Slightly enhanced” = 2 points “No enhancement” = 1 point for the feeling of maturity compared to the control product

As shown in Table 9, the flavor-imparting composition of the present invention imparts flavor to an alcoholic beverage-flavored food or drink at least at a concentration range of 1 ppt to 1 ppm of the compound of formula (1). It was confirmed that the feeling can be improved.

[Example 8] Examples of addition to various meat-flavored foods and drinks Commercially available chicken consommé soup stock was prepared, and chicken consommé soup was prepared according to the instructions on the package. In addition, commercially available gravy sauce was prepared. Then, the product 2-1 of the present invention obtained in Example 2 (the ethanol-diluted solution of the compound of formula (1)) was added to the commercially available chicken consommé soup and gravy sauce, and the concentration of the compound of formula (1) was as shown in Table 10 below. to obtain the meat-flavored foods and drinks of the present invention (Products 8-1 to 8-10 of the present invention). Then, the richness and salty taste of the meat-flavored food and drink of the present invention were subjected to sensory evaluation using a commercially available product as a control product. In the evaluation, 10 well-trained panelists with 10 years or more of experience were asked to rate the richness of the product of the present invention compared to the control product according to the following criteria, and to evaluate the flavor of the product of the present invention compared to the control product. commented freely. Table 10 shows the average scores and typical comments of the 10 panelists.
(Reference) “Greatly enhanced” = 4 points “Enhanced” = 3 points “Slightly enhanced” = 2 points “No enhancement” = 1 point

As shown in Table 10, the flavor-imparting composition of the present invention imparts flavor to various meat-flavored foods and beverages at a concentration of at least the compound of formula (1) in the foods and beverages within a concentration range of 1 ppt to 1 ppm. As a representative example, it was confirmed that richness and saltiness can be imparted.

In addition, from the results shown in Table 10, the flavor-imparting composition of the present invention added flavor (heated It is a complex and delicious flavor that is not simply the food material itself, but is flavored with seasonings and spices, and if necessary, it is heated and cooked to add aroma. It is thought that it is possible to enhance the feeling of For example, it is thought that the flavor-imparting composition of the present invention can impart freshly-cooked aroma and the like to retort foods.

[Example 9] Examples of addition to various spice- or herb-flavored foods and drinks Commercially available garlic-flavored dressing, onion dressing, and retort curry roux were prepared, and the present invention product 2-1 obtained in Example 2 (compound of formula (1) Ethanol diluted solution) was added to each commercial product so that the concentration of the compound of formula (1) became the concentration shown in Table 11 below to obtain the food and drink of the present invention (Products 9-1 to 9-18). Then, sensory evaluation was performed on the richness and salty taste of the food and drink of the present invention using a commercial product as a control product. In the evaluation, 10 well-trained panelists with 10 years or more of experience were asked to rate the richness and saltiness of the product of the present invention compared to the control product according to the following criteria, and the product of the present invention compared to the control product. They were allowed to freely comment on the flavor of Table 11 shows the panelists' average scores and representative comments.
(Reference) “Greatly enhanced” = 4 points “Enhanced” = 3 points “Slightly enhanced” = 2 points “No enhancement” = 1 point

As shown in Table 11, the flavor-imparting composition of the present invention imparts good flavor to various spice- or herb-flavored foods and beverages when the concentration of at least the compound of formula (1) in the foods and beverages is in the range of 1 ppt to 1 ppm. It was confirmed that it can be imparted, and as representative examples, it was confirmed that it was possible to impart richness and salty taste.

In addition, from the results shown in Table 12, the flavor imparting composition of the present invention is particularly useful in flavored articles containing a garlic-like and/or onion-like flavor (e.g., spice tube such as garlic, onion soup, other garlic and/or various seasonings using onions as raw materials).

[Example 10] Example of addition to heat-processed food and drink To a commercially available caramel sauce, the product 2-1 of the present invention obtained in Example 2 (an ethanol-diluted solution of the compound of formula (1)) was added. The compounds were added to a concentration of 10 ppb and mixed well to obtain the sweet food and drink of the present invention (Product 10-1 of the present invention). Regarding the flavor of the sweet food and drink of the present invention, five well-trained panelists with 10 years or more of experience were asked to freely comment on the flavor of the product of the present invention compared to the control product. As a result, all five panelists evaluated that the product of the present invention had enhanced richness and aroma, including sweetness, and became a highly fragrant sauce with a good bitterness and sweetness similar to freshly made caramel sauce. did.

In addition, from the results of Examples 10 and 8, the flavor-imparting composition of the present invention imparts preferable aroma and richness to foods and beverages containing aroma, such as various baked confectioneries and bread, and can be used particularly effectively. it is conceivable that.

[Example 11] Example of addition to cosmetics with citrus-like fragrance A commercially available lemon-like liquid aromatic was prepared. To this, 1% of the lemon fragrance composition of the present invention containing 1 ppm of the compound of formula (1) prepared in Example 2 (Invention Product 2-6) was added to obtain the lemon-flavored fragrance of the present invention. (Present product 11-1). Using a commercially available lemon-like liquid aromatic as a control product, the aroma of the lemon-like aromatic of the present invention was subjected to a sensory evaluation by five panelists with eight or more years of experience. As a result, all five panelists evaluated that the lemon-flavored aromatic agent of the present invention imparted the feeling of lemon peel and fruit juice, and had a fresh, natural scent like that of freshly squeezed lemon.

Claims

A flavor imparting composition comprising a disulfide compound represented by the following formula (1).
The flavor-imparting composition according to claim 1, wherein the flavor-imparting composition further has an effect of enhancing carbonation in addition to imparting flavor.
A consumer product comprising the flavoring composition according to claim 1 or 2.
A method for imparting flavor to consumer goods, comprising adding the flavor imparting composition according to claim 1 or 2 to consumer goods.
A method for imparting flavor to a flavor-imparting composition, comprising adding the flavor-imparting composition according to claim 1 or 2 to another flavor-imparting composition.