Flavor improver composed of sulfide

Abstract

To provide a flavor improver.SOLUTION: A flavor improver contains, as an active ingredient, one or more compounds selected from the group consisting of methylprenyl sulfide, diprenyl sulfide, methylprenyl trisulfide, and diprenyl trisulfide. The flavor improver may be a flavor improver for flavor compositions, a flavor improver for foods and beverages, a fruitiness improver, or a bitterness improver. A method for improving the flavor of consumer products includes the step of adding one or more compounds selected from the group consisting of methylprenyl sulfide, diprenyl sulfide, methylprenyl trisulfide, and diprenyl trisulfide to a consumer product.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a flavor improving agent comprising a sulfide, a consumer goods additive composition containing the same, and a method for imparting flavor to consumer goods. [Background technology]

[0002] In recent years, consumer demands for foods, beverages, and cosmetics have become more sophisticated and diverse, with particular attention being paid to fragrance, with the characteristics of the fragrance becoming an important factor in the appeal of the product. For example, there is an increasing demand for flavor compounds that can improve the fragrance or flavor, or can impart or enhance the persistence, naturalness, and richness of the fragrance or flavor by blending them.

[0003] Various compositions capable of improving aromas and flavors have been proposed up to now. For example, the present applicant has proposed a flavor improver (Patent Document 1) containing bis(3-methyl-2-butenyl) disulfide and / or 3-methyl-2-butenyl 3-methylbutyl disulfide as an active ingredient as a sulfide. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] JP 2019-110859 A Summary of the Invention [Problem to be solved by the invention]

[0005] The technology described in Patent Document 1 can be said to be quite useful, but in order to respond to the demand for improving the flavor of increasingly diverse consumer goods, there is a need to develop new flavor improving agents with high flavor improving effects that can impart better flavors to consumer products and differentiate them from the flavors of existing products.

[0006] In view of the above, an object of the present invention is to provide a novel flavor improving agent, a consumer goods additive composition, and a method for improving the flavor of consumer goods. [Means for solving the problem]

[0007] As a result of intensive research aimed at solving the above problems, the present inventors have discovered that the sulfides methylprenyl sulfide, diprenyl sulfide, methylprenyl trisulfide, and diprenyl trisulfide have excellent flavor improving effects in a wide range of flavors, and have thus completed the invention of the present application.

[0008] Thus, a brief outline of representative inventions among those disclosed in this application is as follows. [1] A flavor improver comprising, as an active ingredient, one or more compounds selected from the group consisting of methylprenyl sulfide, diprenyl sulfide, methylprenyl trisulfide, and diprenyl trisulfide. [2] The flavor improver according to [1], which is a flavor improver for a flavor composition, a flavor improver for food or beverage, a fruitiness improver, or a bitterness improver. [3] A composition for use as an additive in consumer goods, comprising, as an active ingredient, one or more compounds selected from the group consisting of methylprenyl sulfide, diprenyl sulfide, methylprenyl trisulfide, and diprenyl trisulfide. [4] The consumer goods additive composition according to [3], wherein the consumer goods additive composition is a flavor composition, a flavor improving composition for food or beverages, a fruity feeling improving composition, or a bitter feeling improving composition. [5] A method for improving the flavor of a consumer good, comprising the step of adding one or more compounds selected from the group consisting of methylprenyl sulfide, diprenyl sulfide, methylprenyl trisulfide, and diprenyl trisulfide to the consumer good. [6] A method for improving the flavor of a consumer good described in [5], wherein the consumer good is a food or beverage, and in the step, the compounds are added so that the total concentration of the compounds is in the range of 0.01 ppt to 10 ppm, based on the total mass of the food or beverage, thereby improving the flavor of the food or beverage. Effect of the Invention

[0009] According to the present invention, a novel flavor improving agent, a consumer goods additive composition, and a method for improving the flavor of consumer goods can be provided. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0010] An embodiment of the present invention will be described in detail below. In this specification, "to" means a range including a lower limit and an upper limit, and "concentration (ppm, ppb, ppt)" and "%" mean "mass concentration" and "mass percent concentration", respectively, unless otherwise specified. In this specification, "flavor" means one or more senses that can be changed by aroma (scent), typically including smell and / or taste. In this specification, the term "flavor improvement (improving flavor)" includes imparting (adding a new flavor) and / or enhancing flavor, and means that the flavor is improved as a result of imparting or enhancing flavor. In this specification, the flavor of food and beverages is sometimes called flavor. In this specification, "improving the flavor of consumer goods" includes both "improving the flavor of food and beverages, etc." that contributes to the sense of smell and taste, as defined in the above "flavor," and "improving the aroma of cosmetics, etc." that contributes to the sense of smell but not to the sense of taste. In addition, in this specification, the term "adding" includes at least one of simply adding to a certain object by spraying, dropping, or the like, and mixing with a certain object.

[0011] (Flavor improver) The flavor improver according to one embodiment of the present invention (hereinafter sometimes referred to as "the flavor improver") contains one or more compounds selected from the group consisting of methylprenyl sulfide, diprenyl sulfide, methylprenyl trisulfide, and diprenyl trisulfide as active ingredients. Hereinafter, these four compounds may be collectively referred to as "the compounds of the present invention", and methylprenyl sulfide, diprenyl sulfide, methylprenyl trisulfide, and diprenyl trisulfide may be referred to as compound 1, compound 2, compound 3, and compound 4, respectively.

[0012] Methylprenyl sulfide, which is the flavor improver of the present invention, is a compound represented by the following formula 1, diprenyl sulfide is a compound represented by the following formula 2, methylprenyl trisulfide is a compound represented by the following formula 3, and diprenyl trisulfide is a compound represented by the following formula 4.

[0013] [ka]

[0014] Among the flavor improvers in question, methyl prenyl sulfide of formula 1 (Compound 1 in question) has been detected as one of the many components identified in hops (Chemistry & Industry (London, United Kingdom) (1980), (15), 624-5, etc.), and is known to have garlic-, rubber-, and onion-like aromas.

[0015] Diprenyl sulfide of formula 2 (Compound 2 of the present invention) has been described as one of the aroma components that improves palatability in legal cannabis use (U.S. Patent Application Publication No. 2021 / 0251268), but its specific flavoring effect is unknown.

[0016] The production method of methylprenyl trisulfide of formula 3 (Compound 3 of the present invention) is described in Japanese Patent Publication No. 5-56340, which describes that such trisulfides are detected as aroma components in garlic, roasted nuts, coffee, etc., but there is no description of natural products containing methylprenyl trisulfide, or of the aroma or fragrance-imparting effect of methylprenyl trisulfide.

[0017] Although it has been disclosed that diprenyl trisulfide of formula 4 (compound 4 of the present invention) can be used as a spice or fragrance (Chinese Patent Application Publication No. 101376640), its specific fragrance effect is not known.

[0018] The flavor improver of the present invention contains one or more compounds selected from the group consisting of methylprenyl sulfide, diprenyl sulfide, methylprenyl trisulfide and diprenyl trisulfide as active ingredients, but may be substantially composed of only these compounds of the present invention based on the ordinary knowledge of a person skilled in the art. In this case, for example, the inclusion of impurities remaining when these compounds are purchased as reagents is not a problem as long as it does not affect flavor improvement.

[0019] In addition, the present flavor improver is excellent in the effect of improving various flavors, and commonly has a remarkable effect of enhancing the fruity feeling and / or bitter feeling, so the present composition is suitably used as a fruity feeling improver or a bitter feeling improver.

[0020] There are no particular limitations on the consumer goods to which the present flavor improving agent can be added, but examples include various flavor improving compositions including fragrance compositions (details of flavor improving compositions will be described later), foods and beverages, cosmetics, pharmaceuticals, and health and hygiene products.

[0021] The method of obtaining methylprenyl sulfide, diprenyl sulfide, methylprenyl trisulfide and diprenyl trisulfide is not particularly limited, and for example, it may be obtained by synthesis by any method that can be adopted by a person skilled in the art, or it may be purchased as a commercially available product. The obtained methylprenyl sulfide, diprenyl sulfide, methylprenyl trisulfide and diprenyl trisulfide may be further purified by means of column chromatography or reduced pressure distillation, etc., as necessary.

[0022] The concentration of the present flavor improving agent in the flavor improving composition to which the present flavor improving agent is added (when the present compound contains two or more kinds as the present flavor improving agent, the total concentration of the compounds; the same applies below) can be arbitrarily determined according to the flavor characteristics of the flavor improving composition and / or the object to which the flavor improving composition is added, but is preferably within the range of 1 ppb to 0.1% (1000 ppm) based on the total mass of the flavor improving composition. More specifically, it can be within any of the ranges of 10 ppb to 100 ppm, 100 ppb to 100 ppm, 10 ppb to 10 ppm, and 100 ppb to 10 ppm, but is not limited thereto.

[0023] The flavor improving composition to which the present flavor improving agent is added is not particularly limited, but particularly preferred examples include fruit flavor improving compositions (specifically, in the case of citrus fruits, an orange flavor improving composition, a lemon flavor improving composition, a grapefruit flavor improving composition, a lime flavor improving composition, a yuzu flavor improving composition, a kabosu flavor improving composition, a sudachi flavor improving composition, a hassaku flavor improving composition, a shikuwasa flavor improving composition, an iyokan flavor improving composition, a kumquat flavor improving composition, a mandarin flavor improving composition, and a mandarin flavor improving composition, Other examples of fruits include a grape flavor improving composition (grape includes red grapes, white grapes, and black grapes; the same applies below), a peach flavor improving composition, a strawberry flavor improving composition, a mango flavor improving composition, a pear flavor improving composition, an apple flavor improving composition, a pineapple flavor improving composition, a melon flavor improving composition, a banana flavor improving composition, a lychee flavor improving composition, a passion fruit flavor improving composition, a kiwi flavor improving composition, a cherry flavor improving composition, and an apricot flavor improving composition. ), coffee flavor improving composition, tea flavor improving composition (specific examples include a black tea flavor improving composition, a green tea flavor improving composition, a matcha flavor improving composition, a roasted green tea flavor improving composition, and an oolong tea flavor improving composition), beer flavor improving composition, wine flavor improving composition, sake flavor improving composition, distilled liquor flavor improving composition (specific examples include a shochu flavor improving composition and a whiskey flavor improving composition), chocolate flavor improving composition, cocoa flavor improving composition, custard flavor improving composition, caramel flavor improving composition, spices. Herb flavor improving composition (specifically, examples of the composition include a cinnamon flavor improving composition, a cardamom flavor improving composition, a caraway flavor improving composition, a cumin flavor improving composition, a clove flavor improving composition, a pepper flavor improving composition, a coriander flavor improving composition, a Japanese pepper flavor improving composition, a perilla flavor improving composition, a ginger flavor improving composition, a star anise flavor improving composition, a thyme flavor improving composition, a nutmeg flavor improving composition, a basil flavor improving composition, a marjoram flavor improving composition, a rosemary flavor improving composition, and a laurel flavor improving composition).), aromatic vegetable flavor improving compositions (specifically, examples of the flavor improving composition include a green onion flavor improving composition, an onion flavor improving composition, a celery flavor improving composition, a garlic flavor improving composition, and a chive flavor improving composition), livestock meat flavor improving compositions (specifically, examples of the flavor improving composition include a chicken flavor improving composition, a pork flavor improving composition, and a beef flavor improving composition), seafood flavor improving compositions (specifically, examples of the flavor improving composition include various fish flakes used in soup stock such as bonito flakes and dried sardines, and various shellfish flavor improving compositions such as clams, mussels, cockles, and Honbinosu).

[0024] In addition to the flavor of specific food ingredients, the invention also has the effect of improving roasted flavor, fragrant flavor (including the burnt flavor obtained by roasting or heating), bitter flavor, cooked flavor (including the complex and pleasant flavor obtained through cooking processes such as baking, frying, boiling and steaming), salty flavor, green flavor, and ripe flavor (including the unique rich flavor including the sweetness felt from fully ripe fruit).

[0025] It also has a flavor improving effect that reduces the harshness of foods with a harsh taste, and a flavor improving effect that mellows out tingling sensations.

[0026] In particular, when the present flavor improving agent contains methylprenyl sulfide (the present compound 1) as an active ingredient, various flavor improving compositions for soft fruits such as Kyoho grapes, various tropical fruits such as kiwi and passion fruit, various aromatic vegetables such as beer, coffee, chocolate, cocoa, caramel, and green onions, seafood, miso, and soybeans are cited as suitable examples of targets for addition of the present flavor improving agent, and further, flavor improving compositions that reduce the harshness of foods with a harsh taste are also suitable examples.

[0027] In particular, when the present flavor improving agent contains diprenyl sulfide (the present compound 2) as an active ingredient, various flavor improving compositions for imparting a refreshing feeling, a bitter feeling, the flavor of various herbs, a green feeling, a fragrant feeling, and a peppery feeling are cited as suitable examples of targets to which the present flavor improving agent can be added.

[0028] In particular, when the present flavor improving agent contains methylprenyl trisulfide (the present compound 3) as an active ingredient, various flavor improving compositions for soft fruits such as Kyoho grapes, various tropical fruits such as kiwi, beer, coffee, chocolate, cocoa, caramel, and various aromatic vegetables such as green onions and onions are cited as suitable examples of targets to which the present flavor improving agent can be added, and a flavor improving composition that reduces the spiciness of pepper-like spiciness of foods is also cited as a suitable example of targets to which the present flavor improving agent can be added.Furthermore, since it also has an effect of enhancing the salty taste, a flavor improving composition for foods and beverages having a salty taste (especially salty foods and beverages with reduced salt) is also cited as a particularly suitable example of targets to which the present flavor improving agent can be added.

[0029] In particular, when the present flavor improving agent contains diprenyl trisulfide (the present compound 4) as an active ingredient, various flavor improving compositions for ripe fruit, coffee, chocolate, cocoa, caramel, and various aromatic vegetables such as green onions are cited as suitable examples of targets to which the present flavor improving agent can be added.

[0030] In addition, the products to which the flavor improving composition containing the present flavor improving agent is added are not particularly limited, and examples thereof include consumer goods such as food and beverages, cosmetics, medicines, health and hygiene products, etc. In addition, the flavor improving composition containing the present flavor improving agent can be further added to various consumer goods additive compositions to impart a flavor to the consumer goods additive composition and improve the flavor of the consumer goods additive composition.

[0031] The flavors of the foods and beverages to which the present flavor improving agent can be added are not particularly limited, but examples include fruit-flavored foods and beverages (specifically, in the case of citrus fruits, orange-flavored foods and beverages, lemon-flavored foods and beverages, grapefruit-flavored foods and beverages, lime-flavored foods and beverages, yuzu-flavored foods and beverages, kabosu-flavored foods and beverages, sudachi-flavored foods and beverages, hassaku-flavored foods and beverages, shikuwasa-flavored foods and beverages, iyokan-flavored foods and beverages, kumquat-flavored foods and beverages, mandarin-flavored foods and beverages, and mandarin-flavored foods and beverages, and other fruits include grape-flavored foods and beverages (grape includes red grapes, white grapes, and black grapes). (The same applies below.) Examples of the flavors include peach-flavored foods and beverages, strawberry-flavored foods and beverages, mango-flavored foods and beverages, pear-flavored foods and beverages, apple-flavored foods and beverages, pineapple-flavored foods and beverages, melon-flavored foods and beverages, banana-flavored foods and beverages, lychee-flavored foods and beverages, passion fruit-flavored foods and beverages, kiwi-flavored foods and beverages, cherry-flavored foods and beverages, and apricot-flavored foods and beverages.) Coffee-flavored foods and beverages, tea-flavored foods and beverages (specifically, black tea-flavored foods and beverages, green tea-flavored foods and beverages, matcha-flavored foods and beverages, roasted green tea-flavored foods and beverages, and oolong tea-flavored foods and beverages. ), beer-flavored foods and beverages (including beer itself and other beverages with a beer flavor (so-called beer-flavored beverages, etc.)), wine-flavored foods and beverages, sake-flavored foods and beverages, distilled liquor-flavored foods and beverages (specifically, shochu-flavored foods and beverages, and whiskey-flavored foods and beverages), chocolate-flavored foods and beverages, cocoa-flavored foods and beverages, custard-flavored foods and beverages, caramel-flavored foods and beverages, spice- and herb-flavored foods and beverages (specifically, cinnamon-flavored foods and beverages, cardamom-flavored foods and beverages, caraway-flavored foods and beverages, cumin-flavored foods and beverages, clove-flavored foods and beverages, pepper-flavored foods and beverages, and spice- and herb-flavored foods and beverages (specifically, cinnamon-flavored foods and beverages, cardamom-flavored foods and beverages, caraway-flavored foods and beverages, cumin-flavored foods and beverages, clove-flavored foods and beverages, and pepper-flavored foods and beverages). Examples of flavored foods and beverages include coriander-flavored foods and beverages, pepper-flavored foods and beverages, shiso-flavored foods and beverages, ginger-flavored foods and beverages, star anise-flavored foods and beverages, thyme-flavored foods and beverages, nutmeg-flavored foods and beverages, basil-flavored foods and beverages, marjoram-flavored foods and beverages, rosemary-flavored foods and beverages, and laurel-flavored foods and beverages), aromatic vegetable-flavored foods and beverages (specifically, green onion-flavored foods and beverages, onion-flavored foods and beverages, celery-flavored foods and beverages, and garlic-flavored foods and beverages), and meat-flavored foods and beverages (specifically, chicken-flavored foods and beverages, pork-flavored foods and beverages, and beef-flavored foods and beverages.), seafood-flavored foods and beverages (specifically, various fish-flavored foods and beverages used for soup stock, such as bonito flakes and dried sardines, and various shellfish-flavored foods and beverages, such as clams, mussels, cockles, and Honbinosu).), and various foods and beverages having two or more of these flavors.

[0032] Cosmetics to which the present flavor improving agent can be added include, but are not limited to, perfumes such as eau de cologne, eau de toilette, eau de parfum, and parfum; hair care products such as shampoo, rinse, and hair styling products (hair cream, pomade, etc.); cosmetics such as foundation, lipstick, lip balm, lip gloss, lotion, cosmetic emulsion, cosmetic cream, cosmetic gel, beauty essence, and pack; deodorant products such as antiperspirant spray, deodorant sheet, deodorant cream, and deodorant stick; and inorganic salts. Examples include bath additives such as fragrance-based, cooling, carbon dioxide-based, skin care, enzyme-based, and herbal medicine-based bath additives; tanning cosmetics such as suntan products and sunscreen products; health and hygiene detergents such as face soap and facial cleansing cream, body soap and body wash, laundry soap, laundry detergent, disinfectant detergent, deodorizing detergent, fabric softener, kitchen detergent, and cleaning detergent; health and hygiene materials such as toothpaste, tissue paper, and toilet paper; aromatic products such as air fresheners and deodorizers for indoors and in cars, and room fragrances; etc.

[0033] (Flavor improving composition) A flavor improving composition according to one embodiment of the present invention (hereinafter sometimes referred to as "the composition") contains one or more compounds selected from the compound (the group consisting of methylprenyl sulfide, diprenyl sulfide, methylprenyl trisulfide, and diprenyl trisulfide) as an active ingredient.

[0034] As described above, methylprenyl sulfide is a compound represented by the following formula 1, diprenyl sulfide is a compound represented by the following formula 2, methylprenyl trisulfide is a compound represented by the following formula 3, and diprenyl trisulfide is a compound represented by the following formula 4.

[0035] [ka]

[0036] The methods for obtaining methylprenyl sulfide, diprenyl sulfide, methylprenyl trisulfide, and diprenyl trisulfide are as described above in the section "Flavor improvers."

[0037] Here, the flavor improving composition is a concept including compositions that contain extracts of natural flavor materials, essential oils, and / or synthetic flavor materials and improve the flavor and / or taste, etc. For example, a "lemon flavor improving composition" is a composition that has a lemon flavor, or a composition that does not have a lemon flavor itself but can improve the lemon flavor by adding it to an article that has a lemon flavor, and examples of such compositions include lemon extracts, essential oils, and synthetic flavor materials (representatively citral and its analogs, geraniol, etc.), which are natural flavor materials, as well as lemon flavor compositions (flavors or fragrances) and lemon taste-imparting compositions that contain either one or both of these.

[0038] In addition, the composition of the present invention is excellent in the effect of improving various flavors and has a remarkable effect of increasing the fruity feeling and / or bitter feeling in common. Therefore, the composition of the present invention is suitable for use as a fruity feeling improver or a bitter feeling improver.

[0039] The concentration of methylprenyl sulfide, diprenyl sulfide, methylprenyl trisulfide, and diprenyl trisulfide in the present composition (when two or more of these compounds are contained, the total concentration of them. The same applies below.) can be arbitrarily determined according to the flavor characteristics of the consumer goods to which the present composition is added, but is preferably within the range of 0.01 ppt to 10 ppm, more preferably 0.1 ppt to 10 ppm, and even more preferably 1 ppt to 1 ppm, based on the total mass of the consumer goods. For example, the lower limit may be any of 0.01 ppt, 0.1 ppt, 1 ppt, 10 ppt, 100 ppt, 1 ppb, 10 ppb, 100 ppb, and 1 ppm, and the upper limit may be any of 10 ppm, 1 ppm, 100 ppb, 10 ppb, 1 ppb, 100 ppt, 10 ppt, 1 ppt, and 0.1 ppt, and may be within any combination of these lower and upper limits, but is not limited to these concentration ranges. More specifically, the lower limit can be any one of 100 ppt, 1 ppb, 10 ppb, 100 ppb, and 1 ppm, and the upper limit can be any one of 10 ppm, 1 ppm, 100 ppb, 10 ppb, and 1 ppb, and the range can be any combination of these lower and upper limits, but is not limited to these.

[0040] The consumer goods to which the composition of the present invention is added are not particularly limited, and examples thereof include any other flavoring composition (typically a flavoring composition, etc.), food and beverages, cosmetics, medicines, and health and hygiene products, among which food and beverages are preferable. Specific examples of consumer goods are as described above in the section "Flavor improver".

[0041] For example, the present composition can be added to another flavoring composition to improve the flavor of the flavoring composition, and the flavoring composition can be added as the present composition to consumer goods such as food, beverages, and cosmetics to improve the flavor of the consumer goods to which it is added.

[0042] The composition itself may also be added to foods, beverages, or cosmetics to improve the flavor of the products to which it is added.

[0043] In the case of food and beverages, examples of fruit-flavored foods and beverages (specifically, in the case of citrus fruits, examples include orange-flavored foods and beverages, lemon-flavored foods and beverages, grapefruit-flavored foods and beverages, lime-flavored foods and beverages, yuzu-flavored foods and beverages, kabosu-flavored foods and beverages, sudachi-flavored foods and beverages, hassaku-flavored foods and beverages, shekwasha-flavored foods and beverages, iyokan-flavored foods and beverages, kumquat-flavored foods and beverages, mandarin-flavored foods and beverages, and mandarin-flavored foods and beverages; examples of other fruits include grape-flavored foods and beverages (grape includes red grapes, white grapes, and black grapes; the same applies below), peach-flavored foods and beverages, strawberry-flavored foods and beverages, mango-flavored foods and beverages, ... and orange-flavored foods and beverages. Examples of such flavors include pear-flavored foods and beverages, apple-flavored foods and beverages, pineapple-flavored foods and beverages, melon-flavored foods and beverages, banana-flavored foods and beverages, lychee-flavored foods and beverages, passion fruit-flavored foods and beverages, kiwi-flavored foods and beverages, cherry-flavored foods and beverages, and apricot-flavored foods and beverages.), coffee-flavored foods and beverages, tea-flavored foods and beverages (specifically, black tea-flavored foods and beverages, green tea-flavored foods and beverages, matcha-flavored foods and beverages, roasted green tea-flavored foods and beverages, and oolong tea-flavored foods and beverages.), beer-flavored foods and beverages, wine-flavored foods and beverages, sake-flavored foods and beverages, and distilled liquor-flavored foods and beverages (specifically, shochu-flavored foods and beverages). , whiskey-flavored foods and beverages.), chocolate-flavored foods and beverages, cocoa-flavored foods and beverages, custard-flavored foods and beverages, caramel-flavored foods and beverages, spice- and herb-flavored foods and beverages (specifically, cinnamon-flavored foods and beverages, cardamom-flavored foods and beverages, caraway-flavored foods and beverages, cumin-flavored foods and beverages, clove-flavored foods and beverages, pepper-flavored foods and beverages, coriander-flavored foods and beverages, Japanese pepper-flavored foods and beverages, shiso-flavored foods and beverages, ginger-flavored foods and beverages, star anise-flavored foods and beverages, thyme-flavored foods and beverages, nutmeg-flavored foods and beverages, basil-flavored foods and beverages, marjoram-flavored foods and beverages, and rosemary-flavored foods and beverages. and laurel-flavored foods and beverages.), aromatic vegetable-flavored foods and beverages (specifically, green onion-flavored foods and beverages, onion-flavored foods and beverages, celery-flavored foods and beverages, garlic-flavored foods and beverages, and chive-flavored foods and beverages), meat-flavored foods and beverages (specifically, chicken-flavored foods and beverages, pork-flavored foods and beverages, and beef-flavored foods and beverages), seafood-flavored foods and beverages (specifically, various fish-flavored foods and beverages used in soup stock, such as bonito flakes and dried sardines, and various shellfish-flavored foods and beverages, such as clams, mussels, hard clams, and Honbinosu.), and various foods and beverages having two or more of these flavors.is a suitable example.

[0044] When the present composition contains methylprenyl sulfide (the present compound 1) as an active ingredient, particularly suitable examples include foods and beverages with the flavors of soft fruits such as Kyoho grapes, various tropical fruits such as kiwi and passion fruit, beer, coffee, chocolate, cocoa, caramel, various aromatic vegetables such as green onions, seafood, miso, and soybeans. Furthermore, foods and beverages with a harsh taste are also particularly suitable examples, since the present composition has the effect of reducing the harsh taste of the said foods and beverages.

[0045] When the present composition contains diprenyl sulfide (the present compound 2) as an active ingredient, particularly suitable examples include foods and beverages of various flavors whose flavor is improved by imparting at least one of a refreshing feeling, a bitter feeling, the aroma of various herbs, a green feeling, a fragrant feeling, and a peppery feeling.

[0046] When the present composition contains methylprenyl trisulfide (the present compound 3) as an active ingredient, particularly preferred examples include foods and beverages with the flavors of soft fruits such as Kyoho grapes, various tropical fruits such as kiwi, beer, coffee, chocolate, cocoa, caramel, and various aromatic vegetables such as green onions and onions, and particularly preferred examples include foods and beverages with a pepper-like spiciness, since the present composition has the effect of reducing the spiciness of the foods and beverages.Furthermore, since the present composition has the effect of enhancing the salty taste, particularly preferred examples include foods and beverages with a salty taste (especially salty foods and beverages with reduced salt).

[0047] When the present composition contains diprenyl trisulfide (the present compound 4) as an active ingredient, particularly suitable examples include foods and beverages with the flavors of fruit (especially when the flavor is improved by imparting a sense of ripeness to the fruit), coffee, chocolate, cocoa, caramel, and various aromatic vegetables such as green onion.

[0048] When the present composition is added to a flavor composition, which is one embodiment of another flavor-imparting composition, the concentration of the present compound, which is an active ingredient of the present composition, in the flavor composition (when two or more types of the present compound are contained, the total concentration of them; the same applies below) can be arbitrarily determined according to the fragrance characteristics of the flavor composition, but is preferably within the range of 1 ppb to 0.1% (1000 ppm) relative to the total mass of the flavor composition. More specifically, it can be within any of the ranges of 10 ppb to 100 ppm, 100 ppb to 100 ppm, 10 ppb to 10 ppm, and 100 ppb to 10 ppm, but is not limited thereto.

[0049] The present composition may be composed of only one or more of the present compounds (the group consisting of methylprenyl sulfide, diprenyl sulfide, methylprenyl trisulfide, and diprenyl trisulfide) and contain no other components, or may contain other components as long as it contains a predetermined amount of one or more of methylprenyl sulfide, diprenyl sulfide, methylprenyl trisulfide, or diprenyl trisulfide. For example, when the present composition contains a solvent and / or other flavor-imparting components as components other than methylprenyl sulfide, diprenyl sulfide, methylprenyl trisulfide, or diprenyl trisulfide, the present composition itself can be used as a flavor composition, which is one embodiment of a flavor improving composition.

[0050] Examples of such flavor-imparting components include various types of fragrance compounds, natural essential oils, fragrance compositions, oil-soluble pigments, 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, etc.

[0051] Examples of flavor compounds, etc. include natural essential oils, natural flavors, and synthetic flavors 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 Flavor Compounds in Japan (FY2000 Ministry of Health, Labor and Welfare Science Research Report, Japan Flavor and Flavor Manufacturers Association, Issued March 2001)", and "Synthetic Flavors: Chemistry and Product Knowledge (New revised and expanded edition published December 20, 2016, edited by the Synthetic Flavors Editorial Committee, Chemical Daily Co., Ltd.)".

[0052] 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.

[0053] 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.

[0054] Examples of the aldehyde compound 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 perillaldehyde; and aromatic aldehydes such as benzaldehyde, cinnamyl aldehyde, vanillin, ethyl vanillin, heliotropin, and p-tolyl aldehyde.

[0055] 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.

[0056] Examples of the furan or ether compounds include furfuryl alcohol, furfural, rose oxide, linalool oxide, menthofuran, theaspirane, estragole, eugenol, and 1,8-cineole.

[0057] Examples of the ester compound 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.

[0058] Examples of the lactone compound 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.

[0059] 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.

[0060] Examples of the nitrogen-containing compound include indole, skatole, pyridine, alkyl-substituted pyrazine, methyl anthranilate, and trimethylpyrazine.

[0061] Examples of sulfur-containing compounds include methanethiol, dimethyl sulfide, dimethyl disulfide, allyl isothiocyanate, 3-methyl-2-butene-1-thiol, 3-methyl-2-butanethiol, 3-methyl-1-butanethiol, 2-methyl-1-butanethiol, 3-mercaptohexanol, 4-mercapto-4-methyl-2-pentanone, 3-mercaptohexyl acetate, p-mentha-8-thiol-3-one, and furfuryl mercaptan.

[0062] 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.

[0063] Examples of various animal and plant extracts include herb or spice extracts, coffee, green tea, black tea, or oolong tea extracts, milk or dairy products, and various enzymatic decomposition products thereof using lipase or protease, etc.

[0064] The preferred form of the composition of the present invention (a fragrance composition as one embodiment) is a solution in which the composition of the present invention and other components that may be included as necessary are dissolved in a water-soluble or oil-soluble solvent, an emulsion preparation, a powder preparation, or other solid preparations (such as solid fats).

[0065] Examples of water-soluble solvents include ethanol, methanol, acetone, tetrahydrofuran, acetonitrile, 2-propanol, methyl ethyl ketone, glycerin, propylene glycol, and dipropylene glycol. Among these, ethanol or propylene glycol is particularly preferred from the viewpoint of use in food and beverages. Examples of oil-soluble solvents include vegetable oils and fats, animal oils and fats, refined oils and fats (e.g., processed oils and fats such as medium-chain fatty acid triglycerides, and short-chain fatty acid triglycerides such as triacetin and tripropionin), various essential oils, and triethyl citrate.

[0066] In addition, to prepare an emulsion preparation, the present composition can be emulsified with a water-soluble solvent and an emulsifier.The emulsification method of the present composition is not particularly limited, and an emulsion with excellent stability can be obtained by emulsifying with various emulsifiers that have been used in foods and beverages, such as fatty acid monoglycerides, fatty acid diglycerides, fatty acid triglycerides, propylene glycol fatty acid esters, sucrose fatty acid esters, polyglycerin fatty acid esters, lecithin, processed 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, Quillaja saponin casein, or sodium caseinate, using a homomixer, colloid mill, rotating disk homogenizer, high pressure homogenizer, etc. The amount of these emulsifiers used is not strictly limited and can be changed over a wide range depending on the type of emulsifier used, but is usually within the range of about 0.01 to about 100 parts by mass, preferably about 0.1 to about 50 parts by mass, per part by mass of the flavor improving composition to which the flavor improving agent of the present invention has been added or per part by mass of the present composition. In order to stabilize the emulsified state, in addition to water, 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 the emulsion.

[0067] The emulsion thus obtained can be dried to produce a powder formulation, if desired. When producing the powder, sugars such as gum arabic, trehalose, dextrin, sugar, lactose, glucose, starch syrup, and reduced starch syrup can be added as needed. The amount of these to be used can be appropriately selected depending on the desired properties of the powder formulation.

[0068] In addition to the above, the composition of the present invention may contain, if necessary, ingredients that are commonly used in various compositions for additives to consumer goods, such as solvents such as water and ethanol, and retaining agents such as ethylene glycol, propylene glycol, dipropylene glycol, glycerin, hexyl glycol, benzyl benzoate, triethyl citrate, diethyl phthalate, Hercolin, medium-chain fatty acid triglycerides, and medium-chain fatty acid diglycerides.

[0069] (Consumer goods) A consumer good according to one embodiment of the present invention (hereinafter, sometimes referred to as the consumer good) contains a predetermined amount of the flavor improver or the composition. Since the flavor improver or the composition is added in an effective amount to the consumer good, the present invention can provide a consumer good with improved flavor.

[0070] Specific examples of the consumer goods in question are the "foods and beverages to which the flavor improving agent in question can be added" and the "cosmetics to which the flavor improving agent in question can be added" mentioned in the "Flavor improving agent" section above.

[0071] In the present consumer goods, the amount of the present flavor improver or the present composition added to the consumer goods can be arbitrarily determined depending on the flavor of the consumer goods and the degree of the desired effect, and the amount added can be adjusted based on the concentration of the active ingredients methylprenyl sulfide, diprenyl sulfide, methylprenyl trisulfide, and diprenyl trisulfide (when two or more of these compounds are contained, the total concentration of these compounds; the same applies below). Specific examples of the concentrations of methylprenyl sulfide, diprenyl sulfide, methylprenyl trisulfide, and diprenyl trisulfide are as described above in the section on "flavor improvers."

[0072] (Method for improving the flavor of consumer goods) A method for improving the flavor of consumer goods according to one embodiment of the present invention includes a step of adding one or more compounds selected from the present compounds (the group consisting of methylprenyl sulfide, diprenyl sulfide, methylprenyl trisulfide, and diprenyl trisulfide) to the consumer good.

[0073] Adding an effective amount of the present compound to a consumer good can improve the flavor of the consumer good. The present compound can be added as the present flavor improver, or as an active ingredient of the present composition. Therefore, the method for improving the flavor of a consumer good according to the present embodiment can be said to include a step of adding the present flavor improver or the present composition to the consumer good.

[0074] In the flavor improving method for consumer goods according to the present embodiment, the amount of the compound of the present invention added to the consumer goods may be an effective amount for improving the flavor of the consumer goods, and may be arbitrarily set according to the type and form of the consumer goods. In this case, examples of the concentration of the compound of the present invention in the consumer goods are as described above in the section "Flavor improving agent".

[0075] In the method for improving the flavor of consumer goods, the method of adding the present compound (the present flavor improver or the present composition) to the consumer goods is not particularly limited, and the time (timing) of adding the present compound (the present flavor improver or the present composition) to the consumer goods is also not particularly limited.

[0076] In the method for improving the flavor of a consumer good according to the present embodiment, preferably, the consumer good is a food or drink, and in the step, the compounds are added so that the total concentration of the compounds is in the range of 0.01 ppt to 10 ppm based on the total mass of the food or drink. This makes it possible to suitably improve the flavor of the food or drink. It is particularly preferable to improve the fruity taste and / or bitter taste of the food or drink.

[0077] Specific examples of the total concentration include 0.01ppt to 10ppm, more preferably 0.1ppt to 10ppm, and even more preferably 1ppt to 1ppm. For example, the lower limit may be any of 0.01ppt, 0.1ppt, 1ppt, 10ppt, 100ppt, 1ppb, 10ppb, 100ppb, and 1ppm, and the upper limit may be any of 10ppm, 1ppb, 100ppb, 10ppb, 1ppb, 100ppt, 10ppt, 1ppt, and 0.1ppt, and the range may be any combination of the lower limit and upper limit, but is not limited to these concentration ranges. More specifically, the lower limit may be any of 100ppt, 1ppb, 10ppb, 100ppb, and 1ppb, and the upper limit may be any of 10ppm, 1ppb, 100ppb, 10ppb, and 1ppb, and the range may be any combination of the lower limit and upper limit, but is not limited to these concentration ranges. EXAMPLES

[0078] The present invention will be described in more detail below with reference to examples, although the present invention is not limited to these.

[0079] [Example 1] Effect of adding to fragrance composition The effects of adding methylprenyl sulfide, diprenyl sulfide, methylprenyl trisulfide, and diprenyl trisulfide to a lemon flavor composition (flavor improving composition), a grape flavor composition (flavor improving composition), and a strawberry flavor composition (flavor improving composition) were confirmed as follows.

[0080] A 1% ethanol solution containing each of the commercially available compounds 1 to 4 of the present invention (i.e., methylprenyl sulfide, diprenyl sulfide, methylprenyl trisulfide, diprenyl trisulfide) alone (hereinafter, collectively referred to as 1% ethanol solution of the present compounds) and a 1% propylene glycol solution containing each of the compounds 1 to 4 alone (hereinafter, collectively referred to as 1% propylene glycol solution of the present compounds) were prepared. These solutions are also used in the following examples.

[0081] [Example 1-1] Preparation of grapefruit flavor composition A grapefruit-based blended flavor composition was prepared according to the formulation in Table 1 below.

[0082] [Table 1]

[0083] A 1% propylene glycol solution of the present compound was added to a grapefruit-based blended fragrance composition so that the concentration of the present compound in the grapefruit-based blended fragrance composition was the concentration shown in Table 4 below, to prepare the fragrance compositions of the present invention products 1-1 to 1-12. Then, the obtained fragrance compositions of the present invention products 1-1 to 1-12 were subjected to a sensory evaluation by 15 well-trained panelists (with 10 years or more of experience). In the sensory evaluation, the panelists were asked to comment on the aroma of the present invention products 1-1 to 1-12 in comparison with the grapefruit-based blended fragrance composition not containing the present compound as the control product 1-1.

[0084] [Example 1-2] Preparation of grape flavor composition According to the formulation in Table 2 below, a grape (red grape) base blend fragrance composition was prepared.

[0085] [Table 2]

[0086] A 1% propylene glycol solution of the present compound was added to a grape-based blended fragrance composition so that the concentration of the present compound in the grape-based blended fragrance composition was the concentration shown in Table 4 below, to prepare the fragrance compositions of the present invention products 1-13 to 1-24. Then, the obtained fragrance compositions of the present invention products 1-13 to 1-24 were subjected to a sensory evaluation by 15 well-trained panelists (with 10 years or more of experience). In the sensory evaluation, the panelists were asked to comment on the odor of the present invention products 1-13 to 1-24 compared to the grape-based blended fragrance composition not containing the present compound as control product 1-2.

[0087] [Examples 1-3] Preparation of strawberry flavor composition A strawberry base blend flavor composition was prepared according to the formulation in Table 3 below.

[0088] [Table 3]

[0089] A 1% propylene glycol solution of the present compound was added to a strawberry-based blended fragrance composition so that the concentration of the present compound in the strawberry-based blended fragrance composition was the concentration shown in Table 4 below, to prepare the fragrance compositions of the present invention products 1-25 to 1-36. Then, the obtained fragrance compositions of the present invention products 1-25 to 1-36 were subjected to a sensory evaluation by 15 well-trained panelists (with 10 years or more of experience). In the sensory evaluation, the panelists were asked to comment on the aroma of the present invention products 1-25 to 1-36 compared to the strawberry-based blended fragrance composition to which the present compound was not added as the control product 1-3.

[0090] [Examples 1-4] Sensory evaluation of various fragrance compositions The results of the sensory evaluation of Examples 1-1 to 1-3 (Products of the present invention 1-1 to 1-36) are shown in Table 4 below.

[0091] [Table 4]

[0092] As shown in Table 4, it was confirmed that the present compound improves the odor of various fragrance compositions.

[0093] [Example 2] Effects of adding to various fruit-flavored foods and beverages The effects of adding methylprenyl sulfide, diprenyl sulfide, methylprenyl trisulfide, and diprenyl trisulfide to various beverages, such as kiwi juice and passion fruit juice, were confirmed as follows.

[0094] [Example 2-1] Preparation of kiwi juice A 1% ethanol solution of the compound of the present invention was added to commercially available kiwi juice so that the compound had a concentration corresponding to each of the present invention products 2-1 to 2-16 in Table 5 below, to prepare the kiwi juices of the present invention products 2-1 to 2-16.

[0095] The obtained kiwi juices of the present invention products 2-1 to 2-16 were subjected to a sensory evaluation by 15 well-trained panelists (with 10 years or more of experience). The sensory evaluation was carried out by having the panelists comment on the flavor of the present invention products 2-1 to 2-16 compared to the control product 2-1, which was a kiwi juice to which the present compound was not added, and by averaging the scores given by the panelists on the fruitiness compared to the control product 2-1 according to the following evaluation criteria. Here, the fruitiness included the sensation of actually eating a kiwi fruit. <Fruity evaluation criteria> Significantly increased compared to control product 2-1: 5 points Significantly increased compared to control product 2-1: 4 points Somewhat increased compared to control 2-1: 3 points Slightly increased compared to control 2-1: 2 points Equivalent to control 2-1: 1 point [Example 2-2] Preparation of passion fruit juice A 1% ethanol solution of the compound of the present invention was added to commercially available passion fruit juice so that the concentrations of the compound of the present invention corresponded to the present invention products 2-17 to 2-32 in Table 5 below, to prepare the passion fruit juices of the present invention products 2-17 to 2-32.

[0096] Then, the obtained passion fruit juices of the present invention products 2-17 to 2-32 were subjected to a sensory evaluation by 15 well-trained panelists (with 10 years or more of experience). The sensory evaluation was performed by having the panelists comment on the flavor of the present invention products 2-17 to 2-32 compared to control product 2-2, which was a passion fruit juice to which the present compound was not added, and averaging the scores given by the panelists on the fruitiness compared to control product 2-2 according to the following evaluation criteria. Here, the fruitiness included the sensation of actually eating a passion fruit. <Fruity evaluation criteria> Significantly increased compared to control 2-2: 5 points Significant increase compared to control 2-2: 4 points Somewhat increased compared to control 2-2: 3 points Slightly increased compared to control 2-2: 2 points Equivalent to control 2-2: 1 point [Example 2-3] Sensory evaluation of various foods and beverages Table 5 shows the results of the sensory evaluation of Examples 2-1 to 2-2 (Products of the present invention 2-1 to 2-32).

[0097] [Table 5]

[0098] As shown in Table 5, the compound of the present invention was confirmed to improve the flavor of various fruits.

[0099] [Example 3] Effects of adding to various foods and beverages The effects of adding methylprenyl sulfide, diprenyl sulfide, methylprenyl trisulfide, and diprenyl trisulfide to various beverages, such as coffee, milk cocoa, and caramel milk, were confirmed as follows.

[0100] [Example 3-1] Preparation of coffee A 1% ethanol solution of the compound of the present invention was added to commercially available unsweetened black coffee so that the concentrations of the compound of the present invention corresponded to the present invention products 3-1 to 3-16 in Table 6 below, to prepare the coffee products of the present invention 3-1 to 3-16.

[0101] The resulting coffees of the present invention products 3-1 to 3-16 were subjected to a sensory evaluation by 15 well-trained panelists (with 10 years or more of experience). The sensory evaluation was carried out by having the panelists comment on the aroma and flavor of the present invention products 3-1 to 3-16 compared to the control product 3-1, which was coffee to which the present compound was not added, and by averaging the scores given by the panelists on the bitterness compared to the control product 3-1 according to the following evaluation criteria. Here, the bitterness was defined to include a sensation reminiscent of a bitter aroma. <Evaluation criteria for bitterness> Significantly increased compared to control 3-1: 5 points Significantly increased compared to control product 3-1: 4 points Somewhat increased compared to control 3-1: 3 points Slightly increased compared to control 3-1: 2 points Equivalent to control 3-1: 1 point [Example 3-2] Preparation of milk cocoa A 1% ethanol solution of the compound of the present invention was added to commercially available milk cocoa so that the concentrations of the compound of the present invention corresponded to the present invention products 3-17 to 3-32 in Table 6 below, to prepare milk cocoa products of the present invention 3-17 to 3-32.

[0102] The milk cocoas of the present invention 3-17 to 3-32 were subjected to a sensory evaluation by 15 well-trained panelists (with 10 years or more of experience). The sensory evaluation was carried out by having the panelists comment on the flavor of the present invention 3-17 to 3-32 compared to control product 3-2, which was a milk cocoa without the compound of the present invention, and by averaging the scores given by the panelists on the bitterness compared to control product 3-2 according to the following evaluation criteria. Here, the bitterness was defined to include a sensation reminiscent of a bitter aroma. <Evaluation criteria for bitterness> Significantly increased compared to control 3-2: 5 points Significantly increased compared to control product 3-2: 4 points Somewhat increased compared to control 3-2: 3 points Slightly increased compared to control 3-2: 2 points Equivalent to control 3-2: 1 point [Example 3-3] Preparation of caramel milk A 1% ethanol solution of the compound of the present invention was added to commercially available caramel milk so that the concentrations of the compound of the present invention corresponded to the present invention products 3-33 to 3-48 in Table 6 below, to prepare caramel milk of the present invention products 3-33 to 3-48.

[0103] Then, the caramel milk of the present invention 3-33 to 3-48 obtained was subjected to a sensory evaluation by 15 well-trained panelists (with 10 years or more of experience). The sensory evaluation was performed by having the panelists comment on the flavor of the present invention 3-33 to 3-48 compared to the control product 3-3, which was a caramel milk without the compound of the present invention, and by averaging the scores given by the panelists for the caramel feeling compared to the control product 3-3 according to the following evaluation criteria. Here, the caramel feeling was defined as including a sensation reminiscent of a sweet and slightly bitter aroma. <Caramel flavor evaluation criteria> Significantly increased compared to control 3-3: 5 points Significant increase compared to control 3-3: 4 points Somewhat increased compared to control 3-3: 3 points Slightly increased compared to control 3-3: 2 points Equivalent to control 3-3: 1 point [Example 3-4] Sensory evaluation of various foods and beverages Table 6 shows the results of the sensory evaluation of Examples 3-1 to 3-3 (Products of the present invention 3-1 to 3-48).

[0104] [Table 6]

[0105] As shown in Table 6, it was confirmed that the compound of the present invention improves various flavors.

[0106] [Example 4] Effect of adding to various soups The effects of adding methylprenyl sulfide, diprenyl sulfide, methylprenyl trisulfide, and diprenyl trisulfide to aromatic vegetable soup and ramen soup were confirmed as follows.

[0107] [Example 4-1] Preparation of aromatic vegetable soup Aromatic vegetable soup was prepared by dissolving commercially available powdered aromatic vegetable soup (containing chicken bones, green onions, and garlic as ingredients) in hot water, and a 1% ethanol solution of the present compound was added thereto so that the concentration of the present compound corresponded to the present invention products 4-1 to 4-16 in Table 7 below, thereby preparing aromatic vegetable soup products 4-1 to 4-16 of the present invention.

[0108] Then, the obtained aromatic vegetable soups of the present invention 4-1 to 4-16 were subjected to a sensory evaluation by 15 well-trained panelists (with 10 years or more of experience). The sensory evaluation was performed by having the panelists comment on the flavor of the aromatic vegetable soups of the present invention 4-1 to 4-16 compared to the control product 4-1, which was an aromatic vegetable soup without the compound of the present invention, and averaging the scores given by the panelists on the feeling of fullness of the drink compared to the control product 4-1 according to the following evaluation criteria. Here, the feeling of fullness of the drink included the feeling of a stronger flavor and fuller body. <Evaluation criteria for drinkability> Significantly increased compared to control product 4-1: 5 points Significantly increased compared to control product 4-1: 4 points Somewhat increased compared to control product 4-1: 3 points Slightly increased compared to control product 4-1: 2 points Equivalent to control product 4-1: 1 point [Example 4-2] Preparation of soy sauce soup Ramen soup was prepared by dissolving commercially available powdered soy sauce ramen soup (soy sauce flavored ramen soup containing seafood stock, chicken stock, onion, and pepper as ingredients, with reduced salt content to reduce salt) in hot water, and a 1% ethanol solution of the present compound was added thereto so that the concentration of the present compound corresponded to the present invention products 4-17 to 4-32 in Table 7 below, thereby preparing the ramen soups of the present invention products 4-17 to 4-32.

[0109] Then, the ramen soups of the products 4-17 to 4-32 of the present invention obtained were subjected to a sensory evaluation by 15 well-trained panelists (with 10 years or more of experience). The sensory evaluation was carried out by having the panelists comment on the flavor of the products 4-17 to 4-32 of the present invention compared to the control product 4-2, which was a ramen soup without the compound of the present invention, and averaging the scores given by the panelists on the feeling of fullness of the drink compared to the control product 4-2 according to the following evaluation criteria. Here, the feeling of fullness of the drink was defined as including the feeling of a stronger flavor and fuller body. <Evaluation criteria for drinkability> Significantly increased compared to control product 4-2: 5 points Significantly increased compared to control product 4-2: 4 points Somewhat increased compared to control product 4-2: 3 points Slightly increased compared to control product 4-2: 2 points Equivalent to control product 4-2: 1 point [Example 4-3] Sensory evaluation of various soups Table 7 shows the results of the sensory evaluation of Examples 4-1 to 4-2 (Products of the present invention 4-1 to 4-32).

[0110] [Table 7]

[0111] As shown in Table 7, it was confirmed that the compound of the present invention improves various flavors.

[0112] [Example 5] Effect of adding to beer-flavored beverages A 1% propylene glycol solution of the present compound was added to a commercially available beer-taste beverage so that the compound was present at concentrations corresponding to the present invention products 5-1 to 5-16 in Table 8 below, to prepare the beer-taste beverages of the present invention products 5-1 to 5-16.

[0113] The resulting beer-taste beverages, Invention Products 5-1 to 5-12, were then subjected to a sensory evaluation by 15 well-trained panelists (with 10 years or more of experience). The sensory evaluation was performed by having the panelists comment on the flavor of Invention Products 5-1 to 5-16 compared to Control Product 5-1, a beer-taste beverage to which the compound of the present invention was not added, and averaging the scores given by the panelists on the drinkability (as defined above) compared to Control Product 5-1 according to the following evaluation criteria. <Evaluation criteria for drinkability> Significantly increased compared to control product 5-1: 5 points Significantly increased compared to control product 5-1: 4 points Somewhat increased compared to control product 5-1: 3 points Slightly increased compared to control product 5-1: 2 points Equivalent to control product 5-1: 1 point

[0114] [Table 8]

[0115] As shown in Table 8, it was confirmed that the present compound improves the beer flavor.

[0116] [Example 6] Effect of adding to cosmetics A commercially available liquid laundry detergent with a muscat scent was prepared, and a 1% ethanol solution of the present compound was added to it so that the concentration of the present compound was 100 ppb or 1 ppb, thereby preparing laundry detergents of the present invention 6-1 to 6-4.

[0117] Then, the obtained present invention products 6-1 to 6-4 were subjected to a sensory evaluation by 15 well-trained panelists (with 10 years or more of experience). In the sensory evaluation, the panelists were asked to comment on the difference in the odor of each of the present invention products 6-1 to 6-4 compared to the corresponding control product 6, which was the above-mentioned commercially available liquid laundry detergent containing no compound of the present invention.

[0118] The results of the sensory evaluation of the present invention products 6-1 to 6-4 are shown in Table 9.

[0119] [Table 9]

[0120] As shown in Table 9, it was confirmed that the present compound is also effective in improving the fragrance of cosmetics.

[0121] [Example 7] Other examples of additives In addition to the various consumer goods described in the above examples, the present invention can be particularly suitably used to improve the flavor of foods and beverages such as those exemplified in Table 10 below, although the present invention is not limited thereto.

[0122] [Table 10]

Claims

1. A flavor improving agent comprising, as an active ingredient, one or more compounds selected from the group consisting of methylprenyl sulfide, diprenyl sulfide, methylprenyl trisulfide, and diprenyl trisulfide.

2. The flavor improver according to claim 1 , which is a flavor improver for a flavor composition, a flavor improver for food or beverage, a fruitiness improver, or a bitterness improver.

3. A consumer goods additive composition comprising, as an active ingredient, one or more compounds selected from the group consisting of methylprenyl sulfide, diprenyl sulfide, methylprenyl trisulfide, and diprenyl trisulfide.

4. The consumer goods additive composition according to claim 3, wherein the consumer goods additive composition is a flavor composition, a flavor improving composition for food or beverage, a fruity feeling improving composition, or a bitter feeling improving composition.

5. A method for improving the flavor of a consumer good, comprising the step of adding one or more compounds selected from the group consisting of methylprenyl sulfide, diprenyl sulfide, methylprenyl trisulfide, and diprenyl trisulfide to the consumer good.

6. 6. The method for improving the flavor of a consumer good according to claim 5, wherein the consumer good is a food or beverage, and in the step, the compounds are added so that the total concentration of the compounds is in the range of 0.01 ppt to 10 ppm based on the total mass of the food or beverage, thereby improving the flavor of the food or beverage.

Images