JP7154719B2 - 4-Mercapto-1-octanol or its fatty acid ester, and flavor imparting agent - Google Patents

Description

The present invention relates to 4-mercapto-1-octanol or its fatty acid esters and flavoring agents.

In recent years, consumer demand for various products such as food, beverages, cosmetics, pharmaceuticals, and hygiene products has extended to the quality of product flavor. Needs are growing.

For example, many compounds containing sulfur atoms (sulfur-containing compounds) are found in foods as trace aroma components, and are considered to be important compounds for reproducing the natural flavor of foods.

Examples of typical thiols found in nature as sulfur-containing compounds include 2-furylmethanethiol (furfuryl mercaptan) as a volatile component of coffee, and 1-p-menthene-8-thiol (thioterpineol). is an important volatile component of grapefruit, and 2-methylfuran-3-thiol has been found as a volatile component in beef soup, and these are widely used as flavoring compounds. In addition, some compounds having a mercapto group (also called a thiol group or a sulfanyl group) and a carboxylic acid ester group in the molecule are known, and specific examples include 3-mercapto-4-methyl Pentyl acetate is described as presenting a rhubarb-like aroma and increasing in hops aged 51 days or more from flowering. Patent Document 2 describes that 3-mercapto-3-methylbutyl formate can be used to enhance specific flavors such as freshly roasted sesame. Patent Document 3 discloses that 3-mercapto-3-methylbutyl acetate can impart a freshly brewed feeling to coffee in combination with other sulfur-containing compounds such as 2-furfurylmethylsulfide and 2-furfurylmethyldisulfide. is described.

However, conventional sulfur-containing compounds are monotonous in terms of quality and strength of flavor, the available flavor is limited, and it is difficult to obtain a natural flavor like that of natural materials, for at least one reason. Therefore, it has not been possible to sufficiently meet the diverse demands of consumers for the flavor of products, and the search for new compounds useful as flavor imparting agents continues.

WO2018/139153 JP 2010-148412 A JP 2008-259472 A

An object of the present invention is to provide novel compounds useful as flavoring agents.

As a result of intensive research by the present inventors to solve the above problems, a group of compounds of 4-mercapto-1-octanol represented by formula (1) and its fatty acid ester, which are novel compounds not described in the prior art, It has been found that when blended in various articles such as food and drink, cosmetics, and hygiene products, it exerts an excellent aroma imparting effect on a wide range of flavors, and is extremely useful as a flavoring compound.

Thus, the present invention provides the following.
[1] 4-mercapto-1-octanol represented by the following formula (1) or a fatty acid ester thereof.

［式中、Ｒ_１は、水素または炭素数１～４の直鎖もしくは分岐のアルキル基を表す。］
［２］ 下記式（１）で表される４－メルカプト－１－オクタノールまたはその脂肪酸エステルからなる群から選択される１種以上からなる、香味付与剤。

[In the formula, R ₁ represents hydrogen or a linear or branched alkyl group having 1 to 4 carbon atoms. ]
[2] A flavor-imparting agent comprising one or more selected from the group consisting of 4-mercapto-1-octanol represented by the following formula (1) and fatty acid esters thereof.

［式中、Ｒ_１は、水素または炭素数１～４の直鎖もしくは分岐のアルキル基を表す。］
［３］ ［２］に記載の香味付与剤を含有する香料組成物。
［４］ ［２］に記載の香味付与剤または［３］に記載の香料組成物を配合してなる消費財。
［５］ ［２］に記載の香味付与剤を香料組成物に配合することを含む、香料組成物の香味付与方法。
［６］ ［２］に記載の香味付与剤または［３］に記載の香料組成物を消費財に配合することを含む、消費財の香味付与方法。

[In the formula, R ₁ represents hydrogen or a linear or branched alkyl group having 1 to 4 carbon atoms. ]
[3] A fragrance composition containing the flavor-imparting agent according to [2].
[4] Consumer goods containing the flavor-imparting agent of [2] or the fragrance composition of [3].
[5] A method for imparting a flavor to a flavoring composition, comprising blending the flavoring agent according to [2] into the flavoring composition.
[6] A method for imparting flavor to consumer goods, comprising blending the flavor imparting agent of [2] or the flavoring composition of [3] into consumer goods.

ADVANTAGE OF THE INVENTION By this invention, the compound which can be used as a new flavor imparting agent can be provided.

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in more detail with specific examples. In the present specification, "-" means a range including the lower and upper limits, and concentration and % represent mass concentration and mass%, respectively, unless otherwise specified.

(4-mercapto-1-octanol and its esters)
4-Mercapto-1-octanol represented by the following formula (1) and its fatty acid ester are novel compounds that have not been described in the prior art. Hereinafter, it may be referred to as a compound of formula (1).

[In the formula, R ₁ represents hydrogen or a linear or branched alkyl group having 1 to 4 carbon atoms. ]
Preferred examples of the compound of formula (1) include 4-mercapto-1-octanol represented by the following formula (1-1), in which R is hydrogen embodiment), 4-mercaptooctyl formate represented by the following formula (1-2) (4-mercaptooctyl formate, in formula (1), R is COR ₁ and R ₁ is hydrogen), the following formula 4-mercaptooctyl acetate represented by (1-3) (4-mercaptooctyl acetate, in formula (1), R is COR ₁ and R ₁ is an alkyl group having 1 carbon atoms), the following formula ( 4-mercaptooctyl butyrate represented by 1-4) (4-mercaptooctyl butyrate, in formula (1), R is COR ₁ and R ₁ is a linear alkyl group having 3 carbon atoms). be done. The compound of formula (1-1) exhibits a grapefruit-like or tropical fruit-like odor, and the compound of formula (1-2), the compound of formula (1-3), and the compound of formula (1-4) are similar. It gives off fragrance. Therefore, it is considered that all the compounds of formula (1) exhibit similar odors.

(How to obtain the compound of formula (1))
Compounds of formula (1) may be obtained by any method available to those skilled in the art, eg see Tetrahedron, 35, pp. 1339-1343 (1979) and Tetrahedron Lett. , 47, pp. 6067-6070 (2006) etc., it can be synthesized according to the following reaction route while appropriately optimizing the reaction conditions. However, it is not limited to this example, and other synthesis methods may be adopted.

That is, for example, γ-octalactone (compound (a)) is used as a starting material, compound (a) is converted to compound (b) with a thiocarbonylation reagent (Lawson's reagent or Davy reagent), and a Lewis acid (for example, three The thiolactone of the compound (c) is isomerized by a diethyl ether complex of boron fluoride (BF ₃ OEt ₂ )) and converted to lithium aluminum hydride (LiAlH ₄ ) or diisobutylaluminum hydride ((i-Bu) ₂ AlH). After reduction using a reducing agent to obtain an alcohol compound of formula (1-1), the hydroxyl group (OH group, hydroxyl group, also referred to as hydroxy group) is esterified by a known method to obtain formula (1- 2), a compound of formula (1-3) or formula (1-4) may be obtained.

The obtained compound of formula (1) may be further purified by means of known methods such as column chromatography and vacuum distillation, if necessary.

(Flavor imparting agent of the present invention)
The flavor imparting agent of the present invention is characterized by comprising one or more compounds of the formula (1).

［式中、Ｒ_１は、水素または炭素数１～４の直鎖もしくは分岐のアルキル基を表す。］
式（１）の化合物は、それぞれ単独または組み合わせて、それ自体香味付与剤として各種物品に配合することで配合対象に香味を付与できる。本発明者らは、この化合物自体はグレープフルーツやトロピカルフルーツ様の香気を呈するが、後述のように、グレープフルーツやトロピカルフルーツ様の香気のみならず非常に多様な香味付与に有効であるという高い有用性を発見し、本発明に至った。

[In the formula, R ₁ represents hydrogen or a linear or branched alkyl group having 1 to 4 carbon atoms. ]
The compounds of the formula (1) can be used alone or in combination to impart flavor to various articles by blending them into various articles as flavor-imparting agents. The present inventors have found that this compound itself exhibits a grapefruit- or tropical fruit-like aroma, but as described later, it is highly useful in that it is effective not only for imparting grapefruit- or tropical fruit-like aromas but also for imparting a wide variety of flavors. was discovered, leading to the present invention.

The articles to be blended are not particularly limited, but consumer goods such as food and drink, cosmetics, and medical hygiene products can be exemplified. Furthermore, the compound of the present invention can be blended into various perfume compositions to impart fragrance to the composition.

As used herein, flavor means one or more of the senses that may be altered by scent, typically including smell and taste. As used herein, the term "adding flavor" includes newly adding or enhancing the flavor, and for example, the flavor may be improved as a result of the addition. Furthermore, as a result of imparting flavor, sensations other than olfactory and gustatory sensations, such as cold sensation, warm sensation, texture (such as throat, hardness, viscosity, etc., also referred to as texture), stimulating sensation such as carbonic acid and hotness, etc. may be enhanced, suppressed, or improved. Moreover, in the context of food and drink, flavor can be rephrased as flavor.

(Perfume composition of the present invention)
The fragrance composition of the present invention can be used for the purpose of imparting flavor, and can be blended in various articles, including an effective amount of a flavor imparting agent consisting of one or more compounds of formula (1). Specific examples thereof include fragrance compositions for food and drink (also referred to as flavor compositions) and fragrance compositions for cosmetics (also referred to as fragrance compositions). Examples of articles to be blended include, as described above, consumer goods such as food and drink, cosmetics, and medical hygiene products. The form of the perfume composition of the present invention is not particularly limited, and examples thereof include a water-soluble perfume composition, an oil-soluble perfume composition, an emulsified perfume composition, and a powdered perfume composition. The flavor of the fragrance composition is not particularly limited, but specific examples and examples of particularly preferred flavors will be described in detail in the section (Use for various articles) below.

The concentration of the compound of formula (1) in the fragrance composition of the present invention (the total concentration when two or more are used) depends on the desired fragrance of the fragrance composition and the characteristics such as the fragrance to be blended and the application. can be determined arbitrarily. Examples of such concentrations include 0.1 ppt to 10%, preferably 10 ppt to 5%, more preferably 0.1 ppb to 1%, based on the total weight of the perfume composition. More specifically, the lower limit is 0.1 ppt, 1 ppt, 10 ppt, 100 ppt, 1 ppb, 10 ppb, 100 ppb, 1 ppm, 10 ppm, 100 ppm, 1000 ppm, 1%, or 5%, and the upper limit is 10%, 5 %, 1%, 1000 ppm, 100 ppm, 10 ppm, 1 ppm, 100 ppb, 10 ppb, 1 ppb, 100 ppt, 10 ppt, 1 ppt within any combination of these lower and upper limits, but these is not limited to Although it depends on the formulation and fragrance tone of the fragrance composition, when the concentration of the compound of formula (1) in the fragrance composition is less than 0.1 ppt, it is felt that the compounding effect of the compound of formula (1) is low. If it exceeds 10%, it may be felt that the scent derived from the compound of formula (1) is strong and gives unfavorable alterations to the flavor characteristics of the fragrance composition to be blended, but the fragrance to be blended Depending on the flavor of the composition, etc., the concentration may be lower than the lower limit or higher than the upper limit.

Also, the perfume compound of the present invention may contain any other compound or ingredient in addition to the compound of formula (1).

Examples of such compounds or ingredients include various flavor compounds or flavor compositions, oil-soluble pigments, vitamins, functional substances, fish extracts, livestock meat extracts, plant extracts, yeast extracts, animal and plant proteins. , animal and plant protein decomposition products, starch, dextrin, saccharides, amino acids, nucleic acids, organic acids, solvents and the like. 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, edited by the Synthetic Perfume Editorial Committee, published by The Chemical Daily) natural essential oils, natural fragrances, synthetic fragrances, and the like.

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; 3,5-undecatriene and the like.

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 Examples include terpene alcohols such as myrcenol, farnesol, nerolidol, cedrol, α-terpineol, terpinen-4-ol and borneol, 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, hydroxycitronellal, (E)-2-hexenal, and 2,4-octadienal, citronellal, citral, myrtenal, perillaldehyde, and the like. aromatic aldehydes such as terpenealdehyde, benzaldehyde, cinnamylaldehyde, vanillin, ethylvanillin, heliotropine, and p-tolylaldehyde.

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

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

Ester compounds include ethyl acetate, isoamyl acetate, octyl acetate, ethyl butyrate, ethyl isobutyrate, isoamyl butyrate, ethyl 2-methylbutyrate, ethyl isovarate, 2-methylbutyl isovarate, ethylhexano Aliphatic esters such as ate, allylhexanoate, ethylheptanoate, ethylcaprylate, isoamylisovalerate, and ethylnonanoate; linalyl acetate, geranyl acetate, lavandulyl acetate, terpinyl acetate, neryl acetate, etc. Aromatic esters such as terpene alcohol esters, benzyl acetate, methyl salicylate, methyl cinnamate, cinnamyl propionate, ethyl benzoate, cinnamyl isovarate, ethyl 3-methyl-3-phenyl glycidate.

Lactone compounds include saturated or unsaturated lactones such as γ-decen-decenate, γ-dodecalactone, δ-decen-decenate, δ-dodecalactone, 7-decen-4-olide, and 2-decen-5-olide.

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

Nitrogen-containing compounds include indole, skatole, pyridine, 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, 3-mercaptohexanol, 4-mercapto-4-methyl-2-pentanone, 3-mercaptohexyl acetate, p-mentha-8-thiol-3-one and furfuryl mercaptan. .

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

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 various enzymatic decomposition products thereof such as lipase and/or protease.

The perfume composition of the present invention can be prepared by blending the compound of formula (1) with an appropriate solvent or dispersion medium by a known method.

The form of the perfume composition of the present invention is preferably a solution obtained by dissolving the compound of formula (1) or other components in a water-soluble or oil-soluble solvent, an emulsified formulation, a powder formulation, other solid formulations (solid fats, etc.), and the like. .

Examples of water-soluble solvents include ethanol, methanol, acetone, tetrahydrofuran, acetonitrile, 2-propanol, methyl ethyl ketone, glycerin, and propylene glycol. Among these, ethanol or glycerin is particularly preferable from the viewpoint of use in foods and drinks. 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), various essential oils, and triethyl citrate. etc. can be exemplified.

Moreover, in order to prepare an emulsified preparation, the compound of formula (1) can be obtained by emulsifying 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 emulsified liquid can be obtained by using an emulsifier such as sodium caseinate and performing emulsification 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 blended.

Moreover, the emulsion obtained in this way can be made into a powder formulation by drying if desired. At the time of pulverization, saccharides such as gum arabic, trehalose, dextrin, sugar, lactose, glucose, starch syrup, reduced starch syrup, etc., 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.

The perfume composition of the present invention may further contain ingredients commonly used in perfume compositions, if desired. For example, solvents such as water and ethanol, and fragrances such as ethylene glycol, propylene glycol, dipropylene glycol, glycerin, hexylene glycol, benzyl benzoate, triethyl citrate, diethyl phthalate, hakoline, medium chain fatty acid triglyceride, medium chain fatty acid diglyceride. A retention agent may be included.

(Use for various articles)
The flavor-imparting agent of the present invention and the fragrance composition of the present invention containing it can be used by blending in various articles or fragrance compositions used therefor.

For example, the flavor-imparting agent of the present invention and the flavoring composition containing it may itself be blended in food or drink, or may be one or more water-soluble flavorings, emulsified flavoring compositions, or any Flavoring compounds, natural essential oils (for example, the above-mentioned "Patent Office Gazette, Collection of Well-known and Commonly Used Techniques (Fragrance) Part II Food Flavoring", "Survey on the Usage of Food Flavoring Compounds in Japan", and "Synthetic Flavoring Chemistry and Product Knowledge Fragrance compounds described in ”), may be blended in various articles in combination with one or more selected from.

Food and drink that can be blended with the flavor imparting agent of the present invention or the flavor composition of the present invention containing it is not particularly limited. , Iyokan, Yuzu, Shikuwasa, Kumquat, etc. Strawberry, Blueberry, Raspberry, Apple, Cherry, Plum, Apricot, Peach, Pineapple, Banana, Melon, Mango, Papaya, Kiwi, Pear, Grape, Muscat, Kyoho Grape, etc. various fruit flavors (excluding the citrus mentioned above); milk flavors such as milk, yogurt, butter; vanilla flavor; various tea flavors such as green tea, black tea, oolong tea, herbal tea; coffee flavor; cola flavor; cacao flavor; cocoa flavor various mint flavors such as spearmint, peppermint; cinnamon, chamomile, cardamom, caraway, cumin, cloves, pepper, coriander, Japanese pepper, perilla, ginger, star anise, thyme, capsicum, nutmeg, basil, marjoram, rosemary, Various spice or herb flavors such as laurel, garlic, and wasabi; various nut flavors such as almonds, cashew nuts, and walnuts; various liquor flavors such as wine, brandy, whiskey, rum, gin, liqueur, sake, shochu, and beer; onion, celery. , carrots, tomatoes, cucumbers, and other vegetable flavors; chicken, duck, pork, beef, mutton, horse meat, and other meat flavors; , freshwater fish such as carp, shellfish such as turban shells, clams, short-necked clams and corbicula, various crustaceans such as shrimp and crab, various seaweed such as wakame and kelp, and various seafood and seaweed flavors; rice, barley, wheat, malt various grain flavors such as barley and the like; various fat and oil flavors such as meat oils and fats such as beef tallow, chicken oil and lard; and various fish oils and the like; 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 those 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 those that make you feel citrus flavors such as lemon and milk flavors (citrus Flavored lactic acid bacteria drink, etc.), and those with mint flavor, citrus flavor, and cola flavor (mint or lemon flavored cola drink, etc.).

In particular, the flavor-imparting agent of the present invention or the flavor composition of the present invention containing it has various citrus or fruit flavors, milk flavors, various nut flavors, various livestock meat flavors, various seafood flavors, various tea flavors, and coffee flavors. , beer flavor, and various fat and oil flavored foods and drinks. For example, various citrus or fruit flavors, fruit juice feeling, pulp feeling (feeling reminiscent of the fiber quality and texture of fruit pulp), peel feeling (feeling felt when eating the peel, such as bitterness, oily, fibrous, etc.) The above sensations), maturity (for example, a sense of ripeness such as ripe fruit, mature wine or whiskey), bitterness, body, and freshness. Flavor or seafood flavor with juiciness (e.g. moist meat or juicy sensation), fatness derived from livestock or seafood, cooking sensation (smell reminiscent of the aroma and richness felt when eating cooked food) ), body, freshness, and thickness (for example, elasticity reminiscent of meat and a feeling reminiscent of fiber). One or more flavors can be imparted, such as texture, texture that gives a feeling of real nuts, or natural texture. In particular, it can effectively add one or more of juiciness such as fruit juice and gravy, body, and fatness to food and drink, and comprehensively improve the texture, satisfaction, naturalness, thickness, etc. of food and drink. It is possible to increase the palatability of food and drink. Here, in this specification, the body feeling includes the feeling that the flavor is firm, mellow and full, and brings volume and strength to the overall taste. The fresh feeling is reminiscent of natural raw materials such as fruits, vegetables, and leaves that have a flavor that can contribute to various flavors, or immediately after processing them (freshly picked, freshly cut, freshly ground, freshly shaved, It includes sensations reminiscent of the flavor felt in freshly slapped paper, etc.). Thickness includes the feeling that the flavor is not monotonous and that various flavors are felt in a well-balanced manner.

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, butter cream, custard cream, cream puff, waffle, sponge cake, donut, chocolate, chewing gum, caramel, candy, paste such as peanut paste; bread, udon, ramen, Chinese noodles, sushi, Gomoku rice, fried rice, pilaf, gyoza skin, shumai skin, okonomiyaki, takoyaki, and other breads, noodles, rice; Pickles such as those pickle bases; Fish such as mackerel, sardines, saury, salmon, tuna, bonito, whale, flatfish, sand eel, sweetfish, squid such as flying squid, spear squid, crest squid, firefly squid, common octopus, Octopus such as octopus, prawns such as tiger prawns, botan prawns, spiny lobsters and black tigers, crabs such as king crabs, snow crabs, blue crabs and horse crabs, shellfish such as clams, clams, scallops, oysters and mussels; Processed seafood foods such as canned foods, boiled fish, tsukudani, surimi, fish paste products (chikuwa, kamaboko, fried kamaboko, crab leg kamaboko, etc.), fried foods, tempura; chicken, pork, beef, mutton, horse meat, etc. Meat: Curry, stew, beef stew, hayashi rice sauce, meat sauce, mapo tofu, hamburg steak, dumplings, kamameshi mix, soups (corn soup, tomato soup, consommé soup, etc.), meatballs, braised cubes, canned meat, etc. Processed foods and drinks using livestock meat; Table salt, Seasoning salt, Soy sauce, Powdered soy sauce, Miso, Powdered miso, Moromi, Hishio, Furikake, Ochazuke mix, Margarine, Mayonnaise, Dressing, Vinegar, Sanbaizu, Powdered sushi vinegar, Chinese food Nomoto, tempura sauce, noodle soup (kelp or bonito stock, etc.), sauce (chuno sauce, tomato sauce, etc.), ketchup, yakiniku sauce, curry roux, stew mix, soup stock, dashi stock (kelp or bonito stock) Dashi, etc.), seasonings such as compound seasonings, new mirin, mixed flour such as fried chicken powder and takoyaki powder, animal or plant-based dashi-flavored foods and drinks with these seasonings added; cheese, yogurt , butter and other dairy products; various yeasts such as brewer's yeast and baker's yeast; various microbial fermented products such as lactic acid bacteria; vegetables Boiled foods such as simmered foods, Chikuzen simmered dishes, oden, hot pot dishes; ingredients and side dishes for take-out lunch boxes; fruit juice drinks and fruit juice-containing soft drinks such as apples, grapes, citrus fruits (grapefruit, orange, lemon, etc.), fruit pulp Beverages and fruit beverages containing fruit; Vegetables such as tomatoes, green peppers, celery, gourds, bitter melons, carrots, potatoes, asparagus, bracken, and fern, vegetable-based beverages containing these vegetables, vegetable-containing foods and beverages such as vegetable soups Coffee, cocoa, green tea, black tea, oolong tea, soft drinks, cola beverages, carbonated drinks (such as cider with various flavors such as citrus), lactic acid beverages, and other beverages; Beverages containing crude drugs and herbs; Cola beverages, fruit juice beverages , milk drinks, non-alcoholic beer, beer-taste drinks including so-called "third beer", sports drinks, honey drinks, vitamin supplement drinks, mineral supplement drinks, nutritional drinks, nutritional drinks, functional drinks such as lactic acid beverages; Non-alcoholic beverages such as alcohol-flavored beverages with various alcoholic beverages (beer flavor, plum wine flavor, chuhai flavor, etc.); Other brewed liquors (sparkling) such as so-called "third beer" or liqueurs (sparkling), or alcoholic beverages containing these;

Cosmetics to which the flavoring agent of the present invention and the fragrance composition of the present invention containing it can be blended are not particularly limited, but examples include perfumes such as eau de cologne, eau de toilette, eau de parfum, and parfum; shampoos, rinses, and hair styling. Hair care products such as cosmetics (hair cream, pomade, etc.); Cosmetics such as foundation, lipstick, lip balm, lip gloss, lotion, cosmetic milky lotion, cosmetic cream, cosmetic gel, serum, pack agent; Antiperspirant Deodorant products such as sprays, deodorant sheets, deodorant creams, and deodorant sticks; bath agents such as inorganic salt-based, refreshing, carbon dioxide-based, skin care, enzyme-based, and herbal medicine-based products; sunscreen products such as suntan products and sunscreen products. ;Facial cleansers such as face soaps and cleansing creams, body soaps and soaps, laundry soaps, laundry detergents, disinfectant detergents, deodorant detergents, softeners, kitchen detergents, cleaning detergents, etc. for health and hygiene Detergents; Health and hygiene materials such as toothpaste, tissue paper, and toilet paper; Fragrance products such as deodorants for rooms and cars, and room fragrances;

The flavor-imparting agent of the present invention or the flavoring composition of the present invention containing it is not particularly limited, and the flavor can be improved by the flavoring agent of the present invention or the perfume composition containing the same. Any scent tone may be used, but citrus tone, floral tone, fruity tone, green tone, woody tone, moss tone, tropical flower tone, and the like can be suitably used. More specifically lemon, orange, grapefruit, lime, yuzu, kabosu, strawberry, raspberry, apple, pineapple, mango, peach, banana, melon, grape, papaya, kiwi, grapes, rose, jasmine, lily of the valley, hyacinth. , lilac, plumeria, etc., but not limited to these. For example, when blended in various floral-scented articles, it is possible to increase the lively freshness and splendor of flowers.

In the present invention, the concentration of the compound of formula (1) in various articles such as food, beverages and cosmetics can be arbitrarily determined according to the flavor of the article and the desired degree of flavoring effect.

As an example of the concentration, if it is a food or drink, the concentration of the compound of formula (1) (when using two or more, the total concentration thereof) is 0.001 ppt to 100 ppm, preferably, relative to the total mass of the food or drink. is in the range of 0.01ppt to 10ppm, more preferably 0.1ppt to 1ppm. More specifically, the lower limit is 0.001ppt, 0.01ppt, 0.1ppt, 1ppt, 10ppt, 100ppt, 1ppb, 10ppb, 100ppb, 1ppm, or 10ppm, and the upper limit is 100ppm, 10ppm, 1ppm, 100ppb. , 10 ppb, 1 ppb, 100 ppt, 10 ppt, 1 ppt, 0.1 ppt, 0.01 ppt, 0.001 ppt within any combination of these lower and upper limits. Examples of preferred concentrations are 0.1 ppt to 10 ppm, 1 ppt to 1 ppm, 10 ppt to 100 ppb as the concentration of the compound of formula (1) (the total concentration when two or more are used) relative to the total mass of the food or drink. , 100ppt to 10ppb, depending on the flavor characteristics of the food and drink, but is not limited thereto. Although it depends on the type and flavor of the food and drink, if the concentration of the compound of formula (1) in the food and drink is less than 0.001 ppt, the blending effect may be felt to be low, and if it exceeds 100 ppm may be felt that the aroma of the compound of formula (1) itself protrudes and unfavorably alters the flavor of the food and drink to be blended, but depending on the flavor of the food and drink, may be blended at concentrations greater than

In the case of cosmetics, the concentration of the compound of formula (1) (the total concentration when two or more are used) is 0.001ppt to 1000ppm, preferably 0.01ppt to 100ppm, relative to the total mass of the cosmetics. , and more preferably in the range of 0.1 ppt to 10 ppm. More specifically, the lower limit is 0.001ppt, 0.01ppt, 0.1ppt, 1ppt, 10ppt, 100ppt, 1ppb, 10ppb, 100ppb, 1ppm, or 10ppm, and the upper limit is 1000ppm, 100ppm, 10ppm, 1ppm. , 100 ppb, 10 ppb, 1 ppb, 100 ppt, 10 ppt, 1 ppt, 0.1 ppt, 0.01 ppt within any combination of these lower and upper limits. Examples of preferred concentrations are 100ppt to 100ppm, 10ppb to 10ppm, 100ppb to 1ppm as the concentration of the compound of formula (1) (the total concentration when two or more are used) relative to the total mass of the cosmetic. It can be selected from each range depending on 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 less than 0.001 ppt, the compounding effect of the compound of formula (1) is low or there is no change. If it exceeds 1000 ppm, it may be felt that the fragrance of the compound of formula (1) itself is prominent and gives an unfavorable deterioration to the fragrance of the cosmetic product to be blended, but the fragrance of the cosmetic product Depending on the above, the concentration may be lower than the lower limit or higher than the upper limit.

For example, by blending one or more of the compounds of the formula (1) in an effective amount in foods, beverages, cosmetics, etc., natural feeling and fruit juice reminiscent of animal and plant materials used in foods, beverages, cosmetics, etc. Feeling, fruit skin, juiciness, flesh (including texture and thickness of meat), freshness, maturity (including fully ripe or moderately ripe), gorgeousness, freshness, richness, body, The effect is that the thickness and the like are increased, and this can be maintained with a good balance. Any one or more of the top, middle, and last flavors can be enhanced, for example, one or more of top flavor strength, middle and last flavor depth, body feeling, and persistence (also referred to as lingering sound) can be enhanced. be able to. In particular, it is possible to enhance the thickness, body and persistence of the middle and last flavors.

EXAMPLES Hereinafter, the present invention will be described more specifically with reference to Examples. In addition, this invention is not limited to these.

[Example 1] Synthesis of compound of formula (1) The following was synthesized as an example of the compound of formula (1).

(1) Synthesis of 4-mercapto-1-octanol (first step)

Compound (a) γ-octalactone (99.4 g, 0.70 mol), Lawesson's reagent (141.6 g, 0.35 mol) and toluene (700 mL) were placed in a 2 L four-necked flask equipped with a calcium chloride tube, The mixture was stirred under reflux with heating for 2.5 hours. Then, the temperature inside the flask was lowered to 20° C. while stirring under air cooling, and the mixture was allowed to stand overnight to precipitate crystals. Subsequently, the residue was obtained by concentrate|evaporating the filtrate obtained by filter-separating a crystal substance by filter-paper filtration under reduced pressure. n-Hexane was added to this residue to form a precipitate again, followed by filtration, and the filtrate was concentrated under reduced pressure to obtain a residue. This residue was purified twice by silica gel column chromatography (first time: SiO ₂ 150 g, n-hexane:ethyl acetate=10:1, second time: SiO ₂ 400 g, n-hexane:ethyl acetate=20:1). ), 94.8 g of compound (b) was obtained. The yield of this step was 86%.

(Second step)

Compound (b) (94.8 g, 599 mmol) and toluene (800 mL) were placed in a 2 L four-necked flask under a nitrogen atmosphere. Boron trifluoride diethyl ether complex (BF ₃ OEt ₂ ) (17.0 g, 120 mmol, 0.2 equivalents) was added dropwise thereto with stirring at room temperature (about 25°C), and then heated to reflux at 125°C. After stirring for 3 hours at , boron trifluoride diethyl etherate (17.0 g, 120 mmol, 0.2 equivalents) was added and stirred at 125° C. for 2 hours under reflux, then cooled to room temperature overnight ( about 12 hours) and stirred. The resulting reaction solution was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine in that order, and dried over anhydrous magnesium sulfate. After removing the drying agent by filtration, the filtrate was concentrated under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography (SiO ₂ 400 g, n-hexane:ethyl acetate=20:1) to obtain 53.0 g of compound (c). The yield of this step was 56%.

(Third step)

Lithium aluminum hydride (LiAlH ₄ , 25.4 g, 670 mmol) and diethyl ether (400 mL) were placed in a 2 L four-necked flask under a nitrogen atmosphere. A solution of compound (c) (53.0 g, 335 mmol) in diethyl ether (120 mL) was added dropwise thereto over 1.5 hours while stirring under cooling with ice water. After the dropwise addition was completed, the mixture was stirred for 3 hours while the temperature was raised to room temperature (about 25°C). Diluted hydrochloric acid (3.0 L) was added dropwise thereto while cooling with ice water while maintaining the liquid temperature in the flask at 25° C. or lower, and after stirring at room temperature, the organic phase was separated. The aqueous phase was extracted again with 500 mL of diethyl ether to obtain an organic phase again. The two organic phases obtained were mixed, washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to obtain a crude product (54.1 g). The crude product is distilled under reduced pressure, then purified by silica gel column chromatography (SiO ₂ 400 g, n-hexane:ethyl acetate=5:1), and then distilled under reduced pressure (85-86° C., 0.1 kPa or less). to obtain 38.2 g of 4-mercapto-1-octanol (99.7% purity, formula (1-1)). The yield of this step was 70%. The resulting 4-mercapto-1-octanol of formula (1-1) was designated as product 1 of the present invention.

The resulting 4-mercapto-1-octanol exhibited a grapefruit or tropical fruit-like aroma, and its physical properties were as follows.
¹ H NMR (CDCl ₃ , 400 MHz): δ 3.69-3.64 (m, 2H), 2.84-2.75 (m, 1H), 1.82-1.25 (m, 12H), 0 .90(t,J=7.2Hz,3H).
¹³ C NMR (CDCl ₃ , 100 MHz): δ 62.7, 41.0, 38.8, 35.1, 30.3, 29.4, 22.4, 14.0.
MS (EI, 70 eV): m/z 162(4), 144(17), 103(34), 101(22), 87(55), 74(14), 69(100), 68(21), 67(21), 55(41), 43(14), 41(35).

(2) Synthesis of 4-mercaptooctylformate

Under a nitrogen atmosphere, formic acid (1.55 g, 33.7 mmol) and acetic anhydride (Ac ₂ O, 3.44 g, 33.7 mmol) were added to a 50 mL three-necked flask and stirred for 2 hours. The reaction solution was cooled with ice water, and the 4-mercapto-1-octanol obtained in Example 1 (1) (formula (1-1), 3.65 g, 22.5 mmol) and pyridine (1 drop, 0.02 mL or less ) were sequentially added and stirred at room temperature (about 25° C.) for 2 hours. A saturated aqueous sodium hydrogencarbonate solution (50 mL) was added to the obtained reaction solution, and the mixture was extracted with ether (50 mL). The resulting organic phase was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product (3.87 g) was purified by silica gel column chromatography (SiO ₂ : 50 g, n-hexane:ethyl acetate = 50:1) and then subjected to Kugelrohr distillation (125°C, 0.2 kPa). 2.55 g of mercaptooctylformate was obtained (formula (1-2), purity 99%). The yield of this step was 60%. The resulting 4-mercaptooctylformate of formula (1-2) was designated as product 2 of the present invention.

The resulting 4-mercaptooctylformate exhibited a grapefruit or tropical fruit-like aroma, and its physical properties were as follows.
¹ H NMR (CDCl ₃ , 400 MHz): δ 8.06 (s, 1H), 4.18 (t, J = 6.0 Hz, 2H) 2.82-2.73 (m, 1H), 1.96- 1.25 (m, 11H), 0.91 (t, J=7.2Hz, 3H).
¹³ C NMR (CDCl ₃ , 100 MHz): δ 161.1, 63.6, 40.7, 38.8, 35.1, 29.2, 26.1, 22.4, 14.0.
MS (EI, 70 eV): m/z 144 (28), 103 (18) 101 (20), 87 (100), 81 (12), 74 (15), 69 (80), 68 (16), 67 (18), 55(29), 41(23).

(3) Synthesis of 4-mercaptooctyl acetate

A methylene chloride (CH ₂ Cl ₂ , 10 mL) solution of 4-mercapto-1-octanol (formula (1-1), 3.25 g, 20 mmol) obtained in Example 1 (1) was added to a 50 mL three-necked flask. In addition, a methylene chloride (5 mL) solution of acetyl chloride (AcCl, 1.57 g, 20 mmol) was added under a nitrogen atmosphere, and the mixture was stirred at room temperature (about 25°C) for 3 hours. A saturated aqueous solution of sodium hydrogencarbonate (50 mL) was added to the reaction solution, and the mixture was extracted with ether (50 mL). The obtained organic phase was washed successively with tap water and saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product (3.46 g) was purified by silica gel column chromatography (SiO ₂ : 50 g, n-hexane:ethyl acetate = 50:1) and then subjected to Kugelrohr distillation (125°C, 0.2 kPa). 1.62 g of mercaptooctyl acetate was obtained (formula (1-3), purity 98%). The yield of this step was 40%. The resulting 4-mercaptooctyl acetate of formula (1-3) was designated as Product 3 of the present invention.

The resulting 4-mercaptooctyl acetate exhibited a grapefruit or tropical fruit-like aroma, and its physical properties were as follows.
¹ H NMR (CDCl ₃ , 400 MHz): δ 4.07 (t, J=6.4 Hz, 2H), 2.82-2.73 (m, 1H), 2.05 (s, 3H) 1.91- 1.25 (m, 11 H), 0.90 (t, J=7.2 Hz, 3 H).
¹³ C NMR (CDCl ₃ , 100 MHz): δ 171.1, 64.2, 40.7, 38.7, 35.3, 29.2, 26.2, 22.4, 21.0, 14.0.
MS (EI, 70 eV): m/z 144(29), 101(20), 87(100), 74(22), 69(44), 67(11), 55(18), 43(34), 41(14).

(4) Synthesis of 4-mercaptooctyl butyrate

4-mercapto-1-octanol obtained in Example 1 (1) (formula (1-1), 3.25 g, 20 mmol) and triethylamine (Et ₃ N) (2.43 g, 24 mmol) were added to a 50 mL three-necked flask. ), 4-dimethylaminopyridine (DMAP) (0.24 g, 2.0 mmol) and methylene chloride (20 mL) were added, and a solution of butyric anhydride (3.48 g, 22 mmol) in methylene chloride (5 mL) was added under a nitrogen atmosphere. After that, the mixture was stirred at room temperature (about 25°C) for 1 hour. A saturated aqueous solution of sodium hydrogencarbonate (50 mL) was added to the reaction solution, and the mixture was extracted with ether (50 mL). The organic phase was washed successively with tap water and saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (50 g of SiO ₂ , n-hexane:ethyl acetate = 50:1 to 20:1) and then subjected to Kugelrohr distillation (160°C/0.4 kPa) to obtain 4-mercaptooctyl. 1.11 g of butyrate was obtained (formula (1-4), purity 99.2%). The yield of this step was 23%. The resulting 4-mercaptooctyl butyrate of formula (1-4) was named product 4 of the present invention.

The resulting 4-mercaptooctyl butyrate exhibited a grapefruit or tropical fruit-like aroma, and its physical properties were as follows.
¹ H NMR (CDCl ₃ , 400 MHz): δ 4.08 (t, J = 6.4 Hz, 2H) 2.82-2.74 (m, 1H), 2.28 (t, J = 7.6Hz, 2H ) 1.91-1.29 (m, 13H), 0.95 (t, J=7.6Hz, 3H), 0.91 (t, J=7.2Hz, 3H).
¹³ C NMR (CDCl ₃ , 100 MHz): δ 173.7, 63.9, 40.7, 38.7, 36.2, 35.3, 29.2, 26.3, 22.4, 18.4, 14.0, 13.7.
MS (EI, 70 eV): m/z 144(32), 103(8), 102(10), 101(24), 89(10), 88(10), 87(100), 74(23), 71(36), 69(35), 67(8), 55(13), 43(20), 41(13).
[Example 2] Usage example (1) of compound of formula (1): Formulation in fragrance composition A basic blended fragrance composition exhibiting a grapefruit-like fragrance was prepared according to the general formulation shown in Table 1 below. .

To the obtained grapefruit-like basic blended fragrance composition, each of the compounds of formula (1) obtained in Examples 1 (1) to (4) was added, and the compound of formula (1) was added at the concentration shown in Table 2 below. The perfume compositions of the present invention (Inventive Products 5 to 20) were prepared. Sensory evaluation was performed on the obtained perfume composition of the present invention by 14 panelists with 10 years or more of experience. In the sensory evaluation, the basic perfume composition was used as a control product, and the scent compared with the control product was scored from the following viewpoints. The average score is shown in Table 2 below.
(Evaluation criteria) Fresh feeling 4 points: Remarkably increased compared to the control product 3 points: Increased compared to the control product 2 points: Slightly increased compared to the control product 1 point: Same as the control product

As shown in Table 2, it was confirmed that all of the products 5 to 20 of the present invention have an enhanced freshness and a more excellent and desirable aroma by blending the compound of formula (1).

[Example 3] Use example (2) of compound of formula (1): Formulation in fruit-flavored beverage Commercially available 50% grapefruit juice was added with the formula ( The beverages of the present invention were obtained by blending the compounds of 1) at concentrations shown in Table 3 below. Sensory evaluation was performed on the obtained beverage of the present invention by 14 panelists with 10 years or more of experience. In the sensory evaluation, commercial grapefruit juice was used as a control product, and the flavor of the beverage of the present invention compared with the control product was scored from the following viewpoints, and the flavor of each beverage was freely commented. The average score and representative comments obtained are shown in Table 3 below.
(Evaluation criteria) Feeling of fruit skin and fruit juice 4 points: Remarkably increased compared to the control product 3 points: Increased compared to the control product 2 points: Slightly increased compared to the control product 1 point: Compared to the control product does not change

As shown in Table 3, it was confirmed that all of the products 21 to 40 of the present invention imparted an excellent flavor to the fruit-flavored food and drink by blending the compound of formula (1). In particular, the effect was remarkable within the range of 0.1 ppb to 10 ppb.

[Example 4] Usage example (3) of compound of formula (1): Formulation 1 in food and drink using livestock meat
Commercially available chicken soup powder was dissolved in hot water to obtain chicken soup. To the obtained chicken soup, each compound obtained in Example 1 (1) to (3) was blended so that the concentration shown in Table 4 below was obtained, and the chicken soup of the present invention (Inventive products 41 to 60 ) was prepared. As a comparative example, 3-mercapto-1-hexanol, which is a sulfur-containing compound, was added to chicken soup at the concentration shown in Table 4 below to prepare a chicken soup of Comparative Example (Comparative Product 1). The resulting chicken soups of the present invention and comparative products were subjected to sensory evaluation by 14 panelists with 10 years or more of experience. In the sensory evaluation, chicken soup containing nothing (commercially available powder simply dissolved in hot water) was used as a control product. They were asked to give scores and freely comment on the flavor of each chicken soup. The average score and representative comments obtained are shown in Table 4 below.
(Evaluation criteria) Meat juiciness and fatness 4 points: Remarkably increased compared to the control product 3 points: Increased compared to the control product 2 points: Slightly increased compared to the control product 1 point: Compared to the control product does not change

As shown in Table 4, it was confirmed that in all of the products 41 to 60 of the present invention, excellent flavor was imparted to the meat-flavored food and drink by blending the compound of formula (1). In particular, the effect was remarkable within the range of 0.1 ppb to 10 ppb. Such an effect was not obtained with 3-mercapto-1-hexanol, which is the same sulfur-containing compound as the compound of formula (1).

[Example 5] Usage example (4) of compound of formula (1): Formulation 2 in food and drink using livestock meat
A commercially available powdered soup for pork bone ramen was dissolved in hot water to obtain a pork bone soup. To the obtained pork bone soup, each compound obtained in Example 1 (1) to (4) was blended so that the concentration shown in Table 5 below was obtained, and the flavor composition of the present invention (Inventive product 61 ~80) were prepared. As a comparative example, 3-mercapto-1-hexanol, which is a sulfur-containing compound, was blended into the pork bone soup so as to have the concentration shown in Table 5 below to prepare a comparative pork bone soup (comparative product 2). . The resulting pork bone soups of the present invention and comparative products were sensory evaluated by 10 panelists with 10 years or more of experience. In the sensory evaluation, the pork bone soup (commercially available powder simply dissolved in hot water) was used as a control product, and the flavor compared with the control product was scored from the following viewpoints. They were allowed to comment freely on the flavor of the bone broth. The average score and representative comments obtained are shown in Table 4 below.
(Evaluation criteria) Meat juiciness and fatness 4 points: Remarkably increased compared to the control product 3 points: Increased compared to the control product 2 points: Slightly increased compared to the control product 1 point: Compared to the control product does not change

As shown in Table 5, it was confirmed that all of the products 61 to 80 of the present invention imparted an excellent flavor to the meat-flavored food and drink by blending the compound of formula (1). In particular, the effect was remarkable within the range of 0.1 ppb to 10 ppb. Such an effect was not obtained with 3-mercapto-1-hexanol, which is the same sulfur-containing compound as the compound of formula (1).

[Example 6] Use example (5) of the compound of formula (1): Formulation in foods and drinks using nuts Each compound of (1) was blended at a concentration of 5 ppb relative to the total mass of peanut butter to prepare four types of nut products of the present invention (products 81 to 84 of the present invention).

The resulting nut product of the present invention was sensory evaluated by eight panelists with 10 years or more of experience regarding changes in flavor compared to commercially available peanut butter. As a result, all 8 panelists agreed that all of the products 81 to 84 of the present invention had an enhanced rich oily feeling peculiar to nuts compared to the control product, and had a fresh and body feeling like freshly ground nuts. It was evaluated that it had become a certain flavor and had become a more preferable (highly palatable) nut product. In addition, all of the eight panelists said that the above-mentioned enhancement effect was more pronounced in the product 81 of the present invention containing 4-mercapto-1-octanol (product 1 of the present invention) than in the products 82 to 84 of the present invention. evaluated.

[Example 7] Use example (6) of compound of formula (1): Formulation in milk coffee beverage Formula ( Each compound of 1) was blended to a concentration of 1 ppb with respect to the total mass of a commercially available milk coffee beverage, and as shown in Table 7 below, four types of beverages of the present invention (Products 85 to 88 of the present invention) were prepared. did.

Ten panelists with 10 or more years of experience were asked to comment on the flavor of the resulting beverage of the present invention, using a commercially available milk coffee beverage as a control. Then, all of the 10 panelists found that all of the products 85 to 88 of the present invention had enhanced milk fat-like richness and a fragrant bitterness of roasted coffee, increased body, and improved the palatability and response of the beverage. It was evaluated that it increased and became a more preferable (highly palatable) beverage. In addition, all 10 panelists said that the above-mentioned enhancement effect was more pronounced in the product 85 of the present invention containing 4-mercapto-1-octanol (product 1 of the present invention) than in the products 86 to 88 of the present invention. evaluated.

[Example 8] Use example (7) of compound of formula (1): Formulation in beer-flavored beverages Formula ( Each compound of 1) was blended so as to have a concentration of 1 ppb with respect to the total mass of a commercially available beer beverage, and as shown in Table 8 below, four types of beer-flavored beverages of the present invention (Inventive Products 89 to 92) were prepared. prepared.

Regarding the flavor of the obtained beer-flavored beverage of the present invention, seven panelists with 10 years or more of experience were asked to comment on changes in flavor compared to a commercially available beer-flavored non-alcoholic beverage. Then, all of the seven panelists found that all of the products 89 to 92 of the present invention had enhanced hop-like bitterness and body, and the palatability and chewiness of the beverages were increased, making them more preferable (highly palatable). It was evaluated that it became a drink. Six panelists evaluated that invention product 89, which contained 4-mercapto-1-octanol (invention product 1), had a remarkable enhancement effect compared to invention products 90-92. In addition, six panelists evaluated that all of the invention products 89 to 92 had an enhanced aftertaste of flavor.

[Example 9] Use example (8) of the compound of formula (1): Formulation in citrus-scented cosmetics Each compound of formula (1) obtained in 4) was blended to a concentration of 100 ppb with respect to the total mass of the aromatic liquid, and as shown in Table 9 below, four kinds of the aromatic agent of the present invention (the product of the present invention 93-96) were obtained.

Regarding the obtained aromatic liquid of the present invention, six panelists with 10 years or more of experience were asked to evaluate the change in fragrance compared to the control product, using the aromatic liquid of a commercially available aromatic agent as a control product. All of the panelists evaluated that the products 93 to 96 of the present invention enhanced the bitter and slightly oily pericarp-like scent peculiar to lemon and became a more preferable (highly palatable) aromatic. -Mercapto-1-octanol (Inventive product 1) was added to the present product 93. Compared to the present invention products 94 to 96, it was evaluated that the above enhancement effect was remarkable. In addition, five panelists evaluated that all of the products 93 to 96 of the present invention had further improved lingering fragrance properties.

[Summary of Examples]
As shown in the above examples, all of the compounds of formula (1) exhibit a very wide range of flavor-imparting effects and are compounds useful as flavor-imparting agents. In particular, the palatability of various consumer goods can be improved due to the flavor-imparting effect represented by flavor body, freshness, thickness, and juiciness.

Claims (6)

4-mercapto-1-octanol represented by the following formula (1) or a fatty acid ester thereof;

[In the formula, R ₁ represents hydrogen or a linear or branched alkyl group having 1 to 4 carbon atoms. ] A flavor imparting agent comprising one or more selected from the group consisting of 4-mercapto-1-octanol represented by the following formula (1) and fatty acid esters thereof.

[In the formula, R ₁ represents hydrogen or a linear or branched alkyl group having 1 to 4 carbon atoms. ] A fragrance composition containing the flavor-imparting agent according to claim 2 . A consumer product comprising the flavor imparting agent according to claim 2 or the fragrance composition according to claim 3. A method for imparting a flavor to a flavoring composition, comprising blending the flavoring agent according to claim 2 into a flavoring composition. 4. A method of flavoring a consumer good, comprising incorporating the flavoring agent of claim 2 or the flavoring composition of claim 3 into the consumer good.