JP7332563B2 - lactone compound - Google Patents

Description

TECHNICAL FIELD The present invention relates to a lactone compound, a flavor imparting agent comprising the lactone compound, and a fragrance composition containing the flavor imparting agent.

In recent years, consumer demands for foods, beverages, and cosmetics have become sophisticated and diversified, and in particular, attention has been focused on fragrance, and the characteristics of fragrance have become an important factor in the appeal of products. For example, there is an increasing demand for flavoring compounds that can improve the aroma and taste, or impart or enhance the persistence, naturalness, volume, etc. of the aroma and taste.

For example, in furanones to which the compound according to the present invention belongs, a fragrance composition containing 4-(4-methyl-3-pentenyl)-2(5H)-furanone as an active ingredient is used to improve citrus and floral flavors. (Patent Document 1), 2,5-dimethyl-4-hydroxy-3(2H)-furanone, 2-ethyl-4-hydroxy-5-methyl-3(2H)-furanone, 5-ethyl-3- Masking acidity and acidity with hydroxy-4-methyl-2(5H)-furanone or the like (Patent Document 2), enhancing sweetness with 3-hydroxy-4,5-dimethyl-2(5H)-furanone or the like A method (Patent Document 3) was proposed, and also 2,5-dimethyl-4-hydroxy-3(2H)-furanone, 5-ethyl-3-hydroxy-4-methyl-2(5H)-furanone, 2- Ethyl-4-hydroxy-5-methyl-3(2H)-furanone and the like are said to contribute to imparting a rich and elegant sweetness that is very similar to the flavor of hydrogenated oil (Patent Document 4). .

However, there continues to be hope for the development of new compounds that can impart better flavors to consumer products, allowing them to be differentiated from the flavors of existing products.

JP 2017-025182 A JP 2012-34603 A JP-A-4-8264 WO2008/032852

An object of the present invention is to provide a novel compound that can be used to impart flavor to various articles such as foods, beverages and cosmetics.

The present inventors have diligently searched for compounds useful for imparting flavor to various articles such as food, beverages and cosmetics, and have found that various novel lactone compounds, whose use in fragrance has not been known at all, are useful for imparting flavor. I found something.

Thus, the present invention provides the following.
[1] A lactone compound represented by the following formula (1).

［式中、複素環の破線はいずれか１箇所が炭素－炭素間二重結合であることを表し、側鎖の破線はいずれか１または２箇所が炭素－炭素間二重結合であることを表し、ｎ_１は１または２を表し、ｎ_２は１～４の整数を表し、Ｒ_１およびＲ_２は、ｎ_１＝１の場合はそれぞれ独立してメチル基またはエチル基を表し、ｎ_１＝２の場合はそれぞれ独立して水素、メチル基またはエチル基を表す。］
［２］ ［１］に記載のラクトン化合物からなる香味付与剤。
［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、消費財の香味改善方法。
［６］ ［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、香料組成物の香気改善方法。

[Wherein, the broken line of the heterocyclic ring indicates that one of the carbon-carbon double bonds is present, and the broken line of the side chain indicates that one or two of the carbon-carbon double bonds are present. n ₁ represents 1 or 2, n ₂ represents an integer of 1 to 4, R ₁ and R ₂ each independently represents a methyl group or an ethyl group when n ₁ = 1, n ₁ =2 each independently represents hydrogen, a methyl group or an ethyl group. ]
[2] A flavoring agent comprising the lactone compound of [1].
[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 improving the flavor of consumer goods, which comprises blending the flavor-imparting agent of [2] or the flavor composition of [3] into the consumer goods.
[6] A method for improving the aroma of a fragrance composition, comprising blending the flavor-imparting agent of [2] into the fragrance composition.

INDUSTRIAL APPLICABILITY According to the present invention, it has become possible to provide compounds that can be newly used for imparting flavor to various articles such as foods, beverages and cosmetics.

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.

(Lactone compound represented by formula (1))
The lactone compound represented by the formula (1) (also referred to as the lactone compound of the formula (1)) is a group of compounds that has not been known at all to exhibit an aroma or to be used for imparting flavor. This is the first time that the inventors have confirmed the usefulness as a flavor imparting agent. Among the compounds, some analogues with slightly different structures exhibit no odor or exhibit an unpleasant odor. Based on the surprising discovery that the product can be flavored by blending it into the product.

［式中、複素環の破線はいずれか１箇所が炭素－炭素間二重結合であることを表し、側鎖の破線はいずれか１または２箇所が炭素－炭素間二重結合であることを表し、ｎ_１は１または２を表し、ｎ_２は１～４の整数を表し、Ｒ_１およびＲ_２は、ｎ_１＝１の場合はそれぞれ独立してメチル基またはエチル基を表し、ｎ_１＝２の場合はそれぞれ独立して水素、メチル基またはエチル基を表す。］
好ましくは、Ｒ_１およびＲ_２は、ｎ_１＝１の場合はそれぞれメチル基であり、ｎ_１＝２の場合はそれぞれ独立して水素またはメチル基である。ｎ_２は、好ましくは１～３の整数であり、より好ましくは１または２であり、さらに好ましくは１である。側鎖の炭素－炭素間二重結合は、好ましくはいずれか１箇所である。

[Wherein, the broken line of the heterocyclic ring indicates that one of the carbon-carbon double bonds is present, and the broken line of the side chain indicates that one or two of the carbon-carbon double bonds are present. n ₁ represents 1 or 2, n ₂ represents an integer of 1 to 4, R ₁ and R ₂ each independently represents a methyl group or an ethyl group when n ₁ = 1, n ₁ =2 each independently represents hydrogen, a methyl group or an ethyl group. ]
Preferably, R ₁ and R ₂ are each a methyl group when n ₁ =1 and each independently hydrogen or a methyl group when n ₁ =2. _n2 is preferably an integer of 1 to 3, more preferably 1 or 2, even more preferably 1. The carbon-carbon double bond in the side chain is preferably at any one position.

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

(1) Reaction pathway 1 (lactonization)

In the formula, the definitions of n ₁ , R ₁ and R ₂ are the same as those in general formula (1). That is, n ₁ represents 1 or 2, n ₂ represents an integer of 1 to 4, R ₁ and R ₂ each independently represent a methyl group or an ethyl group when n ₁ = 1, and n ₁ =2 each independently represents hydrogen, a methyl group or an ethyl group.

In the above reaction process, propargyl alcohol 1-1 with a protected hydroxyl group is used as a raw material and ethoxycarbonylated using an arbitrary base and ethyl chloroformate to give an unsaturated ester 1-2 having a triple bond. A Grignard reagent is added to the unsaturated ester 1-2 obtained in the presence of a copper reagent to cause a Z-selective conjugate addition reaction to give an unsaturated ester 1-3 having a double bond. Deprotection of the obtained unsaturated ester 1-3 proceeds to cyclization, and the lactone compound of formula (1) can be obtained. A general production method for each step will be described below, but the present invention is not limited thereto. The hydroxyl group-protected propargyl alcohol 1-1 used as a starting material for the above reaction may be either one synthesized according to a general method or a commercially available product. Examples of protective groups include acetal protective groups such as ethoxyethyl group (EE) and tetrahydropyranyl group (THP), and silyl protective groups such as t-butyldimethylsilyl group (TBS). EE groups are preferred. Although the base used in the ethoxycarbonylation reaction is not particularly limited, n-butyllithium is preferred. Grignard reagents used in conjugate addition reactions can be prepared from the corresponding alkyl halides and magnesium. The alkyl halide may be either one synthesized according to a general method or a commercially available product. The copper reagent to be used includes a copper bromide dimethylsulfide complex, copper bromide, copper iodide and the like, and a copper bromide dimethylsulfide complex is preferred. Deprotection conditions must be selected according to the type of protecting group used. An acetal protecting group such as an EE group is generally deprotected by acid hydrolysis, but is not particularly limited. Examples of the acid used for acid hydrolysis include hydrochloric acid and sulfuric acid, with hydrochloric acid being preferred. As the deprotection progresses, it progresses to cyclization and is converted into the desired product.

(2) Reaction pathway 2 (alkylation)
When adding a methyl group or an ethyl group to the lactone compound obtained in reaction route 1, a known alkylation method can be employed. Typically, an alkyl halide (eg, methyl iodide) may be used to alkylate the lactone compound under basic conditions. The alkyl halide may be either one synthesized according to a general method or a commercially available product. For basic conditions, a base such as an organolithium reagent (eg, lithium bis(trimethylsilyl)amide (also referred to as LiHMDS or LHMDS)) can be used. The reaction may be quenched using known reagents (eg, saturated aqueous ammonium chloride).

The lactone compounds obtained in the above reaction routes 1 and 2 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)
Each of the lactone compounds of formula (1) is itself woody, peppery, terpene-like (including the slightly petroleum sensation that can be exhibited by hydrocarbon fragrance compounds and the waxy sensation that can be felt from citrus peel). , citrus peel-like, waxy (wax-like), fatty (fat-like), oily (oil-like), and powdery. can be given. Although there are no particular restrictions on what can be blended, 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 a sense that includes one or more senses that may be altered by scent, typically 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 this specification, the flavor of food and drink may be called flavor.

(Perfume composition of the present invention)
The perfume composition of the present invention contains a predetermined amount of a flavor-imparting agent comprising one or more lactone compounds of formula (1). The perfume composition of the present invention can be blended into various articles. Examples of articles include consumer goods such as food and drink, cosmetics, and medical hygiene products, as described above. 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 concentration of the lactone compound of formula (1) in the perfume composition of the present invention can be arbitrarily determined depending on the object to be blended with the perfume composition and the aroma characteristics.

Examples of such concentrations are in the range of 0.01 ppm to 10%, preferably 0.1 ppm to 1%, relative to the total weight of the perfume composition. More specifically, the lower limit is 0.01 ppm, 0.1 ppm, 1 ppm, 10 ppm, 100 ppm, 1000 ppm, or 1%, and the upper limit is 10%, 1%, 1000 ppm, 100 ppm, 10 ppm, 1 ppm, 0 Any combination of these lower and upper limits may be in the range, but is not limited thereto, as anywhere from .1 ppm. Although it depends on the formulation and fragrance tone of the fragrance composition, if the concentration of the compound of formula (1) in the fragrance composition is less than 0.01 ppm, the blending effect may be felt to be low. If it exceeds, the scent derived from the compound of formula (1) is strong, and it may be felt that the fragrance and / or flavor characteristics of the fragrance composition to be blended are unfavorably altered, but the fragrance of the fragrance composition to be blended. Depending on the composition, etc., the concentration may be lower than the lower limit or higher than the upper limit. In this specification, "-" means a range including the lower limit and the upper limit, and concentration represents mass concentration unless otherwise specified.

Also, the perfume compound of the present invention may contain any other compound or composition in addition to the lactone 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 Perfumery Industry Association, published March 2001) and "Synthetic Perfume Chemistry and Product Knowledge" (published December 20, 2016, enlarged new edition, edited by the Synthetic Perfume Editorial Committee, The Chemical Daily) natural essential oils, natural fragrances, synthetic fragrances, and the like.

Other examples of synthetic fragrance compounds include hydrocarbon compounds such as monoterpenes such as α-pinene, β-pinene, myrcene, camphene and limonene; sesquiterpenes such as valencene, cedrene, caryophyllene and longifolene; - 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 Terpene alcohols such as myrcenol, farnesol, nerolidol and cedrol, 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, diacetyl, 2,3-pentanedione, maltol, ethyl maltol, cyclotene, 2,5- diketones and hydroxyketones such as dimethyl-4-hydroxy-3(2H)-furanone, terpene ketones such as carvone, menthone, nootkatone, ketones derived from terpene degradation products such as α-ionone, β-ionone, β-damascenone, Aromatic ketones such as raspberry ketones are included.

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

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

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

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

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

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, and furfuryl mercaptan.

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

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

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

Examples of the form of the fragrance composition of the present invention include a solution obtained by dissolving the lactone compound of formula (1) and 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. preferable.

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 lactone compound of formula (1) can be emulsified with a water-soluble solvent and an emulsifier. The method for emulsifying the lactone compound of formula (1) is not particularly limited, and various types of emulsifiers conventionally used in food and drink, such as fatty acid monoglycerides, fatty acid diglycerides, fatty acid triglycerides, and propylene glycol fatty acid esters. , sucrose fatty acid ester, polyglycerol fatty acid ester, lecithin, modified starch, sorbitan fatty acid ester, quillaya extract, gum arabic, tragacanth gum, guar gum, karaya gum, xanthan gum, pectin, alginic acid and its salts, carrageenan, gelatin, casein quillaya saponin A highly stable emulsion can be obtained by emulsifying with an emulsifier such as sodium caseinate using a homomixer, a colloid mill, a rotating disc type homogenizer, a high pressure homogenizer, or the like. The amount of these emulsifiers to be used is not strictly limited, and can vary over a wide range depending on the type of emulsifier used. 0.01 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 thus obtained 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 perfume retention such as ethylene glycol, propylene glycol, dipropylene glycol, glycerin, hexyl glycol, benzyl benzoate, triethyl citrate, diethyl phthalate, hacoline, medium chain fatty acid triglyceride, medium chain fatty acid diglyceride, etc. agent.

(Use for various articles)
The flavor-imparting agent of the present invention comprising the lactone compound of formula (1) and the flavoring composition of the present invention containing the same can be used by blending in various articles or flavoring compositions used therefor.

For example, the flavor-imparting agent comprising the lactone compound of formula (1) and the flavoring composition containing the same may itself be blended in food or drink, or may contain one or more water-soluble flavoring agents, emulsifying agents, or Flavoring composition, arbitrary flavoring compound, natural essential oil (for example, the above-mentioned "Patent Office Gazette, Collection of Well-known and Commonly Used Techniques (Fragrance) Part II Food Flavoring", "Usage Survey of Food Flavoring Compounds in Japan", and " Synthetic fragrances, fragrance compounds described in "Chemistry and Product Knowledge"), may be blended in various articles in combination with one or more selected from.

Food and drink to which the flavoring agent of the present invention comprising the lactone compound of formula (1) or the flavoring composition of the present invention containing the same can be added is not particularly limited. Various citrus flavors such as mandarin, mandarin orange, kabosu, sudachi, hassaku, iyokan, yuzu, shikuwasa, kumquat; strawberry, blueberry, raspberry, apple, cherry, plum, apricot, peach, pineapple, banana, melon, mango, papaya, kiwi , pear, grape, muscat grape, kyoho grape, and other fruit flavors; milk, yogurt, butter, and other milk flavors; vanilla flavor; green tea, matcha, hojicha, black tea, oolong tea, pu-erh tea, herbal tea, and other tea flavors; coffee flavor Cola flavor; Cacao flavor; Cocoa flavor; Various mint flavors such as spearmint and peppermint; Various spices or herbal flavors such as nutmeg, basil, marjoram, rosemary, laurel, wasabi, Japanese pepper; various nut flavors such as almonds, cashews, walnuts; wine, brandy, whiskey, rum, gin, liqueur, sake, shochu, beer Various alcoholic beverage (alcohol) flavors such as; vegetable flavors such as carrot, tomato, and cucumber; 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 beverages, etc.), and those with mint, citrus, and cola flavors (mint or lemon flavored cola beverages, etc.), the lactone compound of formula (1) or a flavor composition containing it It may be any flavor that can be flavored by Examples of flavors that can be preferably used include various fruit flavors represented by citrus, beer flavor, various tea flavors represented by black tea, green tea, matcha, roasted tea, oolong tea, pu-erh tea, milk flavor, fat flavor, and meat flavor. , coffee flavors, and various spice or herb flavors including, but not limited to, ginger and perilla.

More specific examples of food and drink include senbei, 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; milk, cream Dairy products such as , cheese, yogurt, and butter; Boiled vegetables, Chikuzen-ni, oden, hot pot, and other boiled foods; fruit juice beverages, soft drinks containing fruit juice, fruit pulp beverages and fruit beverages containing fruit pulp; vegetables such as tomatoes, green peppers, celery, gourds, bitter melons, carrots, potatoes, asparagus, bracken, and fern, including these vegetables Vegetable-based beverages, vegetable-containing beverages such as vegetable soup; various tea beverages such as coffee, cocoa, green tea, black tea, oolong tea, matcha, roasted tea, and pu-erh tea; and herbal beverages; cola beverages, fruit juice beverages, dairy beverages, non-alcoholic beer and beer-flavored beverages (also called beer-flavored beverages) including so-called "third beer", sports drinks, honey beverages, vitamin supplement beverages, Functional drinks such as mineral supplement drinks, nutrition drinks, nutrition drinks, and lactic acid beverages; Sake, beer, chuhai, cocktail drinks, low-malt beer, fruit wine, spiced wine, so-called "third beer" and other brewed alcoholic beverages (sparkling) or liqueurs (sparkling), or alcoholic drinks containing these ; and the like.

The flavor-imparting agent of the present invention comprising the lactone compound of formula (1) and the perfume composition of the present invention containing the flavor-imparting agent of the present invention are not particularly limited, but examples thereof include eau de cologne, eau de toilette, eau de parfum, and parfum. perfumes; hair care products such as shampoos, rinses, and hair styling agents (hair creams, pomades, etc.); Cosmetics such as packs; Deodorant products such as antiperspirant sprays, deodorant sheets, deodorant creams, and deodorant sticks; Bath agents such as inorganic salt-based, refreshing, carbon dioxide-based, skin care-based, enzyme-based, and crude drug-based products; Suntan products , sunscreen products and other tanning cosmetics; facial cleansers such as face soaps and cleansing creams, body soaps and body soaps, laundry soaps, laundry detergents, disinfectant detergents, deodorant detergents, fabric softeners, kitchen detergents, Health and hygiene detergents such as cleaning detergents; Health and hygiene materials such as toothpaste, tissue paper, and toilet paper; Fragrance products such as room and car interior deodorants and room fragrances; . Usable fragrance tone is not particularly limited, and may be any flavor that can be improved by the lactone compound of formula (1) or a fragrance composition containing the same, such as citrus tone, floral tone, fruity tone. It can be suitably used for tone, woody tone, green tone, and the like.

In the present invention, the concentration of the lactone 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 degree of desired effect.

As an example of the concentration, in the case of food and drink, the concentration of the lactone compound of formula (1) is in the range of 10 ppt to 10 ppm with respect to the total weight of the food and drink. More specifically, the lower limit is 10ppt, 100ppt, 1ppb, 10ppb, 100ppb, or 1ppm, and the upper limit is 10ppm, 1ppm, 100ppb, 10ppb, 1ppb, or 100ppt. Including, but not limited to, any combination of ranges. Examples of preferred concentrations are 100ppt to 100ppb, 100ppt to 1ppm, 1ppb to 100ppb, 1ppb to 1ppm, 10ppb to 1ppm, 10ppb to 100ppb as the concentration of the compound of formula (1) of the present invention with respect to the total weight of food and drink. can be selected depending on the flavor characteristics of the food or drink, but is not limited to these. Although it depends on the type and flavor of the food and drink, if the concentration of the lactone compound of formula (1) in the food and drink is less than 10 ppt, the effect of improving the flavor may be felt to be low. In some cases, it is felt that the aroma of the compound itself is prominent and the flavor of the food and drink to be blended is unfavorably altered.

In the case of cosmetics, the concentration of the lactone compound of formula (1) of the present invention is in the range of 10 ppt to 10% with respect to the total weight of the cosmetics. More specifically, the lower limit is 10ppt, 100ppt, 1ppb, 10ppb, 100ppb, 1ppm, 10ppm, 100ppm, 1000ppm, or 1%, and the upper limit is 10%, 1%, 1000ppm, 100ppm, 10ppm, 1ppm, Any of 100 ppb, 10 ppb, 1 ppb, 100 ppt includes, but is not limited to, any combination of these lower and upper limits. Examples of preferred concentrations include the concentration of the lactone compound of the formula (1) of the present invention with respect to the total weight of the cosmetic, from each range of 1 ppm to 1000 ppm, 10 ppm to 1000 ppm, 10 ppm to 1%, and 100 ppm to 1%. , can be selected according to the fragrance characteristics of cosmetics, but is not limited to these. Although it depends on the type and fragrance of the cosmetic product, when the concentration of the lactone compound of formula (1) in the cosmetic product is less than 10 ppt, it may be felt that the effect of improving the fragrance is low or there is no change. If it exceeds 10%, it may be felt that the fragrance of the cosmetics to be blended is unfavorably altered.

The lactone compound of formula (1) can impart a good aroma or flavor to various products, and can, for example, enhance the volume and aftertaste from the middle to the last. For example, by blending a minute amount of the compound of the present invention into foods, beverages, cosmetics, and other articles, natural feeling, fruit juice, freshness, and voluminousness reminiscent of the animal and plant materials used in foods, drinks, cosmetics, etc. , Body feeling, gorgeousness, richness, fat or oily feeling, etc. are enhanced, and the flavor has a core, which can be maintained with a good balance. As a specific example, if it is a fruit flavor, it can give a feeling of fruit juice, a feeling of peel (bitterness, astringency, waxiness, etc.), a feeling of body, richness, etc., and a feeling of body, richness, and flavor can be imparted with a beer flavor. It is possible to impart lingering and longevity, milky flavor can impart milk fat feeling and richness, and herb flavor such as ginger and perilla can impart freshness, richness and body feeling. If it is a floral tone, it can impart a natural feeling and a lingering scent. As specific examples of the lactone compound of formula (1), for example, the compound of formula (1-1) is excellent in imparting rich flavor, body, and aftertaste to various citrus fruits, ginger, and black tea. ) is excellent in imparting rich flavor of various citrus fruits (especially lime) and various herbs, body feeling, afterglow, etc., and the compound of formula (1-3) is various citrus fruits, various teas (especially black tea, matcha). , Excellent for imparting rich flavor, body, and aftertaste to various dairy products (milk, cream, etc.). ), beer, coffee, and black tea, and is excellent in imparting flavor, body, and aftertaste, but is not limited thereto.

Furthermore, the flavor-imparting agent of the present invention also has the effect of masking off-flavours such as bitterness, astringency, harshness (collectively referred to as astringent taste), and protein odors as a result of imparting flavor. That is, the flavor-imparting agent of the present invention is blended in food and drink that may have a problem of having a strong astringent taste or protein odor and being perceived as an off-taste and off-odor. By imparting seeds or the like, a protruding offensive taste and offensive odor can be masked. Examples of such foods and beverages include foods and beverages containing a high amount of protein. More specifically, protein beverages, concentrated liquid diets, various highly nutritious foods such as highly nutritious beverages, and substitutes using vegetable proteins. meat (also referred to as vegetable meat) and the like, but are not limited to these. In order to obtain the masking effect, the concentration in food and drink can be adjusted. For example, in the concentration range of 10ppt to 10ppm described above, a sufficient masking effect can be obtained by adding the agent to food and drink at a slightly higher concentration. Examples of the concentration range in which the masking effect is likely to be obtained include any of 1 ppb, 10 ppb, 100 ppb, 500 ppb, 1 ppm and 5 ppm as the lower limit and any one of 10 ppm, 5 ppm, 1 ppm, 500 ppb, 100 ppb and 10 ppb as the upper limit. Specific examples include, but are not limited to, 10 ppb to 1 ppm or 100 ppb to 500 ppb. You can decide.

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]
As examples of the lactone compound of formula (1), compounds of the following formulas (1-1) to (1-4) were synthesized.

(1) Synthesis of compound of formula (1-1) and compound of formula (1-2) First, Biosci. Biotechnol. Biochem. 2020, 84, 1560-1569. The compound of Formula A below was synthesized according to the method described on page 1, and then synthesized as per the reaction scheme below.

(i) Compound A (330 mg, 1.83 mmol) and tetrahydrofuran (4.5 mL) were placed in a 100 mL two-necked flask and stirred at −78° C. under an argon atmosphere. Lithium bis(trimethylsilyl)amide (LHMDS) (1.0 M THF solution, 2.00 mL, 2.00 mmol) was added thereto, and after stirring at the same temperature for 1 hour, methyl iodide (0.57 mL, 9.16 mmol) was added. and stirred at 0° C. for 2 hours.

(ii) Saturated aqueous ammonium chloride (30 mL) was added to the reaction solution obtained in (i) to quench. 1M Hydrochloric acid (10 mL) was added thereto, and the mixture was extracted with ethyl acetate (50 mL). The organic layer was washed successively with saturated aqueous sodium bicarbonate (50 mL) and saturated brine (50 mL), dried over magnesium sulfate, and concentrated under reduced pressure to obtain a crude product (357 mg). This product was purified by flash silica gel column chromatography (SiO ₂ : 15 g, hexane:ethyl acetate = 30:1 → 15:1) to obtain 139 mg of the compound of formula (1-1) and the compound of formula (1-2). 160 mg of compound was obtained. This compound of formula (1-1) was designated as Product 1 of the present invention.

Additionally, the compound of formula (1-1) was further purified by Kugelrohr (oven settings: ~210°C/0.27 kPa) to give 132 mg as a colorless oil. The compound of formula (1-2) was also purified by Kugelrohr (oven settings: ~240°C/0.27kPa) to give 154mg as a colorless oil. This compound of formula (1-2) was designated as Product 2 of the present invention.

The physical properties of the compound of formula (1-1) and the compound of formula (1-2) obtained were as follows.
Physical properties of the compound of formula (1-1)
¹ H-NMR (400 MHz, CDCl ₃ ): δ 1.27 (s, 6H), 1.63 (s, 3H), 1.71 (s, 3H), 2.04 (m, 2H), 2.19 (m, 2H), 5.11 (m, 1H), 6.47 (t, J=2.0Hz, 1H).
¹³ C-NMR (100 MHz, CDCl ₃ ): δ 17.8, 23.0 (2C), 23.6, 25.3, 25.6, 44.6, 123.2, 129.2, 132.7, 134.5, 183.3.
IR (total reflection measurement): 2971, 2929, 2913, 2872, 1792, 1462, 1443, 1382, 1280, 1267, 1093, 1039, 952, 839, 817, 755, 575 cm ^-1 .
DART-TOFMS: m/z calcd. for _C12H19O2 [M+H] ⁺ 195.1380, found _{195.1388 .}
Physical properties of the compound of formula (1-2)
¹ H-NMR (400 MHz, CDCl ₃ ): δ 1.40 (d, J = 7.2 Hz, 3H), 1.60 (s, 3H), 1.69 (s, 3H), 1.82 (s, 3H), 2.10-2.32 (m, 3H), 2.50 (m, 1H), 4.88 (m, 1H), 5.07 (m, 1H).
¹³ C-NMR (100 MHz, CDCl ₃ ): δ 8.6, 17.7, 18.2, 25.6, 26.1, 26.6, 78.6, 122.2, 123.1, 133.7 , 164.0, 174.6.
IR (total reflection measurement): 2977, 2927, 2860, 1746, 1675, 1444, 1375, 1323, 1099, 1056, 1037, 1002, 983, 971, 920, 766 ^{cm -1} .
DART-TOFMS: m/z calcd. for _C12H19O2 [M+H] ⁺ 195.1380, found _{195.1391 .}

(2) Synthesis of compound of formula (1-3) Am. Chem. Soc. 2008, 130, pp. 12598-12599, the compound of formula B below was synthesized and then synthesized according to the reaction route below.

(i) Magnesium (234 mg, 9.63 mmol), a catalytic amount of iodine, and tetrahydrofuran (3 mL) were placed in a 30 mL two-necked flask and placed under an argon atmosphere. A small amount of the tetrahydrofuran solution of the compound of formula C is gradually added thereto while stirring well, and when the color of iodine disappears, the compound C solution is gradually added while maintaining the reaction solution at 30° C. or less (compound C Total amount 1.43 g, 8.77 mmol), and then stirred at room temperature for 2 hours.

(ii) Put copper (I) bromide-dimethylsulfide complex (1.80 g, 8.76 mmol) and tetrahydrofuran (4 mL) in a 100 mL three-necked flask under an argon atmosphere while stirring at an extremely low temperature of -78°C. After gradually adding the reaction solution obtained in i), the mixture was stirred at -78°C for 50 minutes, then a solution of compound B (500 mg, 2.19 mmol) in tetrahydrofuran (2 mL) was gradually added, and the mixture was stirred at -78°C. Stirred for 1.5 hours.

(iii) Ethanol (1 mL) was added to the reaction solution obtained in (ii) at −60° C. or lower, and after heating to room temperature, 20% aqueous ammonium chloride (20 mL) was added. The reaction solution was extracted with ethyl acetate (30 mL), washed with 20% aqueous ammonium chloride solution (20 mL), saturated soda ash solution (20 mL), and then with saturated brine (20 mL), dried over magnesium sulfate, and concentrated under reduced pressure. A crude product (861 mg) of the compound of formula D was obtained through purification. This crude product was directly subjected to the next step.

(iv) Crudely purified compound D (861 mg), tetrahydrofuran (7.0 mL) and 1 M hydrochloric acid (7.00 mL, 7.00 mmol) were placed in a 100 mL eggplant-shaped flask and stirred at room temperature for 30 minutes. Saturated soda ash water (30 mL) was added to the resulting reaction solution, and extraction was performed with diethyl ether (30 mL). The resulting organic layer was washed with saturated brine (30 mL), dried over magnesium sulfate, and concentrated under reduced pressure to obtain a crude product (599 mg). This crude product was purified by flash silica gel column chromatography (SiO ₂ : 30 g, hexane:ethyl acetate = 30:1 → 25:1), and further purified by Kugelrohr (oven setting: ~230°C / 0.27 kPa). Purification yielded 307 mg of the compound of formula (1-3) as a colorless oil. This compound of formula (1-3) was designated as Product 3 of the present invention.

The physical properties of the obtained compound of formula (1-3) were as follows.
¹ H-NMR (400 MHz, CDCl ₃ ): δ 1.45 (s, 6H), 1.64 (s, 3H), 1.71 (d, J=0.8Hz, 3H), 2.24-2. 35 (m, 4H), 5.09 (m, 1H), 5.71 (m, 1H).
¹³ C-NMR (100 MHz, CDCl ₃ ): δ 17.8, 24.8 (2C), 25.2, 25.6, 27.0, 87.3, 113.9, 122.1, 133.5, 172.3, 177.3.
IR (total reflection measurement): 2980, 2930, 2913, 1745, 1637, 1461, 1453, 1443, 1383, 1366, 1264, 1240, 1198, 1156, 1079, 976, 938, 888, 852 ^{cm -1} .
DART-TOFMS: m/z calcd. for _C12H19O2 [M+H] ⁺ 195.1380, found _{195.1384 .}

(3) Synthesis of compound of formula (1-4)

(i) Ethyl vinyl ether (93.90 g, 1.30 mol) was placed in a 500 mL four-necked flask and stirred at 4° C. under a nitrogen atmosphere. P-toluenesulfonic acid (150 mg, 1.0 wt %) was added thereto, and the atmosphere was again made under a nitrogen atmosphere. The compound of formula E (15.00 g, 214 mmol) was added thereto and stirred at 6° C. for 40 minutes. Saturated soda ash water (150 mL) was added to the reaction solution, and the mixture was extracted with diethyl ether (20 mL). The resulting organic layer was washed with saturated brine (150 mL), dried over magnesium sulfate, and concentrated under reduced pressure to obtain a crude product (42.41 g). This crude product was purified by distillation under reduced pressure (boiling point 72-88°C/6.7 kPa) to obtain 26.60 g of the compound of formula F as a colorless oil.

(ii) Compound F (20.62 g, 145 mmol) and tetrahydrofuran (375 mL) were placed in a 1 L four-necked flask and stirred at -78°C under a nitrogen atmosphere. n-Butyllithium (1.59 M hexane solution, 100 mL, 159 mmol) was added dropwise thereto over 30 minutes, followed by stirring at the same temperature for 1 hour. Then, ethyl chloroformate (17.25 g, 159 mmol) was added dropwise over 20 minutes, followed by stirring at the same temperature for 30 minutes, gradually raising the temperature to room temperature, and stirring for a total of 1.5 hours. Ethanol (4 mL) was added to the reaction solution, then saturated aqueous ammonium chloride (200 mL) was added, and the organic layer was separated. The resulting organic layer was washed with saturated soda ash water (200 mL), dried over magnesium sulfate, and concentrated under reduced pressure to obtain a crude product (40.17 g). This crude product was purified by distillation under reduced pressure (boiling point: 110-115°C/0.27 kPa) to obtain 26.74 g of the compound of formula G as pale yellow oil.

(iii) Catalytic amounts of iodine, magnesium (3.74 g, 154 mmol) and tetrahydrofuran (70 mL) were placed in a 500 mL four-necked flask and placed under a nitrogen atmosphere. A small amount of the compound of the formula H is gradually added thereto while stirring well, and when the color of iodine disappears, the compound H is gradually added while maintaining the reaction solution at 30° C. or less (the total amount of the compound H is 22.83 g. , 140 mmol) and then stirred at room temperature for 2 hours.

(iv) Put copper (I) bromide-dimethylsulfide complex (28.78 g, 140 mmol) and tetrahydrofuran (105 mL) in a 500 mL four-necked flask under a nitrogen atmosphere at a cryogenic temperature of -78°C while stirring (iii). The resulting reaction solution was gradually added and stirred at −78° C. for 50 minutes. Stirred for an hour.

(v) Ethanol (20 g) was added to the reaction solution obtained in (iv) at −55° C. or lower, and after raising the temperature to room temperature, 20% aqueous ammonium chloride (200 mL) was added. The reaction solution was extracted with hexane (100 mL), washed successively with saturated soda ash solution (200 mL) and saturated brine (200 mL), dried over magnesium sulfate, and concentrated under reduced pressure to obtain a crude product (24.41 g). . The product was purified by distillation under reduced pressure (boiling point: 141-161°C/0.40 kPa) to obtain 17.63 g of the compound of formula I as a colorless oil.

(vi) Compound I (10.00 g, 33.5 mmol), tetrahydrofuran (60 mL) and 2M hydrochloric acid (40.00 mL, 80.0 mmol) were placed in a 300 mL two-necked flask and stirred at room temperature for 22 hours. Saturated soda ash water (100 mL) was added to the obtained reaction solution, and the mixture was extracted with diethyl ether (100 mL). The resulting organic layer was washed with saturated soda ash water (100 mL) and saturated brine (100 mL) in that order, dried over magnesium sulfate, and concentrated under reduced pressure to obtain a crude product (7.04 g). This crude product was purified by silica gel column chromatography (SiO ₂ : 80 g, hexane:ethyl acetate = 10:1→7:1), and further purified by distillation under reduced pressure (boiling point: 150 to 151°C/0.40 kPa). 3.48 g of a colorless oily compound of formula (1-4) was obtained. This compound of formula (1-4) was designated as Product 4 of the present invention.

The physical properties of the obtained compound of formula (1-4) were as follows.
¹ H-NMR (400 MHz, CDCl ₃ ): δ 1.62 (s, 3H), 1.70 (s, 3H), 2.23 (t, J = 7.2 Hz, 2H), 2.29 (t, J = 7.2 Hz, 2H), 2.38 (t, J = 6.4 Hz, 2H), 4.37 (t, J = 6.4 Hz, 2H), 5.06 (m, 1H), 5. 81 (br, 1H).
¹³ C-NMR (100 MHz, CDCl ₃ ): δ 17.7, 24.9, 25.6, 27.9, 36.6, 65.9, 115.8, 122.1, 133.3, 161.3 , 164.8.
IR (liquid film method): 2968, 2915, 2856, 1724, 1398, 1377, 1268, 1222, 1083, 1052 cm ^-1 .
DART-TOFMS: m/z calcd. for _C11H17O2 [M+H] ⁺ 181.1223, found _{181.1228 .}

[Example 2] Aroma properties of the synthesized lactone compound of formula (1) Each lactone compound of formula (1) obtained in Examples 1 (1) to (4) (that is, formula (1-2), compounds of formula (1-3) and formula (1-4)) were evaluated for aroma. In addition, as a control product, 4-(4-methyl-3-pentenyl)-2(5H)-furanone described in JP-A-2017-25182, which is a lactone compound, was also evaluated for aroma. For these odor evaluations, five well-trained panelists with 10 or more years of experience were asked to smell and comment on the perceived odors. Representative comments are shown in Table 1 below.

As shown in Table 1, each lactone compound of formula (1) of the present invention (Inventive Products 1 to 4) exhibited a characteristic odor. Regarding formula (1-4), four panelists also commented that woody contains grain nuances and citrus contains floral nuances.

The aroma of each lactone compound of the formula (1) of the present invention also has characteristics not found in the same lactone compound, 4-(4-methyl-3-pentenyl)-2(5H)-furanone. It can be said that each lactone compound of the formula (1) can impart a flavor different from that of the analog 4-(4-methyl-3-pentenyl)-2(5H)-furanone.

[Example 3] Effect of blending with fruity flavor compound A grapefruit-like basic blended flavor composition was prepared according to the general formulation in Table 2 below.

In the obtained basic blended fragrance composition, each lactone compound of formula (1) obtained in Examples 1 (1) to (4) is added so that it is 0.1% with respect to the total mass of the basic blended fragrance composition. to obtain perfume compositions of the present invention (present invention products 5 to 8). Then, eight panelists with 10 or more years of experience were asked to evaluate the fragrance of the fragrance composition of the present invention, using the basic blended fragrance composition as a control product. As a result, all eight panelists answered that all of the perfume compositions of the present invention remarkably enhanced the citrus peel-like waxy and oily feeling and the afterglow of the fragrance.

[Example 4] Effect of blending in fruit-flavored food and drink Commercially available grapefruit juice of 50% fruit juice was prepared, and the concentration of each lactone compound of formula (1) in this juice was 1 ppb and 0.1 ppm as shown in Table 3 below. Alternatively, the fruit-flavored beverage of the present invention was prepared by blending so as to be 10 ppm. The natural feeling of the fruit-flavored beverage of the present invention was sensory evaluated using a commercially available 50% grapefruit juice as a control. Specifically, 12 well-trained panelists with more than 10 years of experience were asked about the natural feeling compared to the control product. = 2 points, and "no change" = 1 point. Here, the term "natural feeling" means that some flavor reminiscent of the grapefruit used as the material is enhanced, and a natural flavor as if a greater amount of grapefruit was used. The average scores and representative comments of the 12 panelists are shown in Table 3 below.

As shown in Table 3, it was confirmed that each lactone compound of formula (1) exerts a characteristic flavor-imparting effect typified by fruit skin feeling, richness and body feeling. In addition, it was confirmed that the flavor-imparting effect can be obtained at least within the concentration range of 1 ppb to 10 ppm in food and drink, and as a result, the natural feeling can be enhanced.

[Example 5] Effect of blending in milk-flavored food and drink Each lactone compound of formula (1) obtained in Examples 1 (1) to (4) was blended into commercially available low-fat milk at 200 ppb. Thus, the milk-flavored beverage of the present invention was obtained. Then, using commercially available low-fat milk as a control product, the flavor of the milk-flavored beverage of the present invention compared with the control product was subjected to a sensory evaluation by 10 well-trained panelists with 10 years or more of experience. Specifically, for the 10 panelists, the richness compared to the control product was “greatly improved” = 4 points, “improved” = 3 points, “slightly improved” = 2 points, “no change” = They were given a score of 1 and were asked to comment on the flavor. Table 4 below shows the average scores and typical comments of the 10 panelists.

As shown in Table 4, it was confirmed that each lactone compound of formula (1) exerts a characteristic flavor-imparting effect typified by milky fat feeling and body. In addition, it was confirmed that the flavor-imparting effect can be obtained at least within the concentration range of 1 ppb to 10 ppm in food and drink, and as a result, the richness can be enhanced.

[Example 6] Effect of blending in beer-flavored beverages Each lactone compound of formula (1) obtained in Examples 1 (1) to (4) was blended with a commercially available non-alcoholic beer so as to be 100 ppb. Thus, the non-alcoholic beer beverages of the present invention (Products 33 to 36 of the present invention) were obtained. Then, using a commercially available non-alcoholic beer as a control product, sensory evaluation was performed by 12 well-trained panelists with 10 years or more of experience regarding the flavor of the beverage of the present invention compared with the control product. As a result, all 12 panelists answered that compared to the control product, the beer-like body and richness were enhanced, the aftertaste of the flavor lasted longer, and the satisfaction and satisfaction after drinking increased. Among them, the product 36 of the present invention containing the compound of formula (1-4) was answered that these effects were remarkable.

[Example 7] Effect of blending in black tea beverage Each lactone compound of formula (1) obtained in Examples 1 (1) to (4) was added to a commercially available sugar-free black tea beverage at a concentration of 50 ppb. Thus, the black tea beverages of the present invention (Products 37 to 40 of the present invention) were obtained. Then, using a commercially available black tea beverage as a control product, sensory evaluation was performed by five panelists who had been well trained for the flavor of the black tea beverage of the present invention compared to the control product, and had more than 10 years of experience, and what kind of flavor was enhanced. I asked him to answer about Taka. As a result, all five panelists found that all of the black tea beverages of the present invention had an enhanced astringent flavor, such as the use of plenty of black tea leaves, compared to the commercially available black tea beverage of the control product, and had a body feeling. responded that there was an increase in Among them, present invention product 37 blended with the compound of formula (1-1), present invention product 39 blended with the compound of formula (1-3), and present invention product blended with the compound of formula (1-4) 40 responded that these effects were significant.

[Example 8] Effect of blending with coffee Commercially available canned black coffee was added with each lactone compound of formula (1) obtained in Examples 1 (1) to (4) at a concentration of 100 ppb with respect to the total amount of coffee. The coffee beverages of the present invention (Products 41 to 44 of the present invention) were obtained. Then, using commercially available canned black coffee as a control product, the flavor of the coffee beverage of the present invention compared to the control product was subjected to a sensory evaluation by five well-trained panelists with 10 years or more of experience. I was asked to answer whether it was enhanced. As a result, all five panelists found that the coffee beverages of the present invention had increased coffee oil-like richness, coffee bean-like astringency, and good acidity compared to the control commercial coffee beverage. I answered yes. Among them, the product 44 of the present invention containing the compound of formula (1-4) was answered that these effects were remarkable.

[Example 9] Blending effect on various spice flavors Commercially available ginger-flavored dressing and perilla-flavored dressing, each lactone compound of formula (1) obtained in Example 1 (1) to (4) was added to the total amount of dressing The spice-flavored dressings of the present invention (ginger-flavored dressings: Products 45 to 48 of the present invention, shiso-flavored dressings: Products 49 to 52 of the present invention) were obtained by blending to a concentration of 1 ppm. Then, using each commercially available dressing as a control product, the flavor of the dressing of the present invention compared to the control product was subjected to a sensory evaluation by 7 well-trained panelists with 10 years or more of experience, and what kind of flavor was enhanced. answered about.

As a result, with regard to the ginger-flavored dressing, all seven panelists answered that the refreshing stimulating feeling peculiar to ginger, the richness of the oil, and the persistence of the flavor were enhanced in all of the products 45 to 48 of the present invention. , the present invention product 45 blended with the compound of formula (1-1), the present invention product 46 blended with the compound of formula (1-2), and the present invention product 48 blended with the compound of formula (1-4) , responded that these effects were significant.

Regarding the perilla-flavored dressing, all seven panelists answered that the products 49 to 52 of the present invention have a unique freshness like perilla oil, richness of oil, and enhanced flavor sustainability. They answered that the product 50 of the present invention containing (1-2) and the product 51 of the present invention containing the compound of formula (1-3) exhibited high enhancement effects.

[Example 10]
Each lactone compound of formula (1) was added to a commercially available protein drink at a concentration of 500 ppb to obtain protein drinks of the present invention (Products 53 to 56 of the present invention). Then, using a commercially available protein drink as a control, four well-trained panelists with 10 years or more of experience were asked to answer changes in the flavor of the protein drink of the present invention compared to the control. As a result, all six panelists found that the protein drink of the present invention had more richness and volume than the control product, the commercially available protein drink, and the unique bitterness and astringency felt in high-concentration protein was reduced. They answered that the so-called protein odor was weakened and the feeling of satisfaction increased as a whole, and that the present invention product 56, in which the compound of formula (1-4) was blended, had remarkable effects.

[Example 11] Effect of blending in muguet-like fragrance composition A muguet-like basic blended fragrance composition was prepared according to the general formulation in Table 5 below.

The resulting muguet-like basic blended fragrance composition was blended with each lactone compound of formula (1) of the present invention obtained in Examples 1 (1) to (4) so that the concentration was 2 ppm. Inventive perfume compositions (Inventive Products 57-60) were prepared. Then, using the muguet-like basic blended fragrance composition as a control, the fragrance of the fragrance composition of the present invention was subjected to a sensory evaluation by 7 well-trained panelists with 8 years or more of experience, and what kind of flavor was enhanced. answered about. As a result, all seven panelists found that the fragrance composition of the present invention had a refreshing fragrance peculiar to muguet, somewhat reminiscent of soap, compared to the basic fragrance composition of the control product. In particular, the product 57 of the present invention containing the compound of formula (1-1) and the product 60 of the present invention containing the compound of formula (1-4) were green. They answered that the slightly powdery floral scent was enhanced in the product 59 of the present invention containing the compound of formula (1-3). Furthermore, six of the panelists answered that all of the products 57 to 60 of the present invention had a longer lasting lingering floral fragrance.

As described above, it was confirmed that each lactone compound of formula (1) exerts an excellent flavor-imparting effect in various flavors and is useful as a flavor material.

Claims (6)

A lactone compound represented by any one of the following formulas (1-1) to (1-4) .

A flavor imparting agent comprising the lactone compound according to claim 1 . A fragrance composition comprising the flavor imparting agent according to claim 2. A consumer product comprising the flavor imparting agent according to claim 2 or the perfume composition according to claim 3. A method for improving the flavor of consumer goods, comprising blending the flavor imparting agent of claim 2 or the flavor composition of claim 3 into the consumer goods. A method for improving the aroma of a perfume composition, comprising blending the flavor-imparting agent according to claim 2 into the perfume composition.