JP6315529B1 - Aroma and / or flavor improver containing dodecenoic acid - Google Patents

Abstract

[Problem] To provide a fragrance / flavor improver capable of improving aroma / flavor such as milk flavor and oily feeling in foods and drinks or cosmetics, and a fragrance composition containing the improver as an active ingredient. 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid or 10-dodecenoic acid itself has unique aroma characteristics such as green-like, uri-like, oily and fat-like, soap-like, and a perfume composition. Alternatively, it has been found that by adding to foods and beverages or cosmetics, the aroma and flavor such as milky feeling and oily feeling are improved and the scent sustainability is increased. [Selection figure] None

Description

  The present invention relates to a fragrance and / or flavor improver comprising dodecenoic acid useful as a fragrance compound and the like, and a fragrance composition containing the fragrance and / or flavor improver as an active ingredient.

  In recent years, with the diversification of consumer preferences, development of various products that meet consumer needs is desired. In particular, this trend is strong in the food and beverage industry, and there is a strong demand for the development of a variety of food and drink that matches the taste of consumers. In response to these demands, the flavor (food fragrance) compounds that have been proposed in the past have not been able to adequately respond to the fragrance that is one of the raw materials for foods and drinks. Development of flavor compounds possessing excellent durability is an urgent issue.

  In recent years, in particular, there are many requests for the purpose of imparting and enhancing flavors and flavors such as milky fat feeling and oily feeling to foods and drinks, etc., but conventional flavor compounds alone have led to demands for diversifying consumer preferences in recent years. Since it has become very difficult to respond, there is a strong demand for the development of flavor compounds that have unique aroma and flavor characteristics that are unprecedented and have a high scent persistence.

  In addition, cosmetics are often required to impart and enhance oil-like flavors and flavors, but at present, they are responding to diversified needs by combining complex odors.

For the purpose of imparting the aroma and flavor of milk fat feeling, for example, Patent Document 1 discloses that (E) -6-nonenal is used in milk, dairy products, milk or foods containing dairy products, or dairy substitutes. It describes a fragrance compound that improves milk flavor and milk flavor by containing 50 ppt to 200 ppb. However, this compound was not satisfactory although it was effective in the richness and milk fat feeling peculiar to milk. Patent Document 2 provides a milk flavor improving agent for spirantol or a plant extract or plant essential oil containing spirantol for milk, dairy products, food or drink containing dairy products or dairy substitutes. Have been described. However, it takes time to prepare spirantol. Furthermore, Patent Document 3 describes a method for enhancing the milk fat sensation of a milk-based fragrance composition in which 12-methyltridecanal is contained in an amount of 1 ppb to 10 ⁴ ppm with respect to the milk-based fragrance composition. However, a satisfactory aroma improvement effect was not obtained.

  For the purpose of imparting a fat scent and flavor, for example, Patent Document 4 discloses δ-lactones such as δ-tridecalactone, δ-tetradecalactone, δ-hexadecalactone, and δ-octadecalactone. It is described that it is useful as an oil and fat feeling enhancer. However, this compound also has fragrances other than oily feeling and is not necessarily satisfactory as an oiliness enhancing agent. Further, Patent Document 5 discloses a sesame-like fresh sensation, freshness and oiliness enhancer comprising 2-methyl-3-thiophenethiol, and Patent Document 6 discloses 3-mercapto-3-methyl. A sesame-like freshly roasted, roasted, and oily fat enhancer comprising butyl formate is described. However, these compounds enhance sesame oily feeling.

  As a fragrance use of dodecenoic acid, Patent Document 7 has a milky aroma with a slight bluishness by adding trans-6-dodecenoic acid to a milk flavor, and Patent Document 8 discloses 5-dodecene. It is described that it has a green-like buttery odor by adding acid to the butter flavor. However, Patent Document 7 shows that linear alkenoic acid having a double bond at positions other than 6 and cis-6-alkenoic acid do not have such aroma.

  Patent Document 9 describes 11-dodecenoic acid as a bad breath remover using it as a fragrance.

Japanese Patent No. 6041937 JP 2017-23063 A Japanese Patent No. 5399083 JP 2011-83264 A Japanese Patent No. 4931900 Japanese Patent No. 4931901 JP 58-59908 A JP 58-96014 A Japanese Patent Laid-Open No. 9-110662

  An object of the present invention is to provide a fragrance and / or flavor improving agent capable of improving aroma and flavor such as milk flavor and oily feeling in foods and drinks, and a fragrance composition containing the improving agent as an active ingredient. It is.

  As a result of intensive studies to solve the above problems, the present inventors have found that 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid or 10-dodecenoic acid is itself green-like, uri-like. It has unique aroma characteristics such as oil and fat feeling and soap-like, and improves flavor and flavor such as milk fat feeling and oil and fat feeling by adding it to a perfume composition or food and drink, and also enhances fragrance sustainability. As a result, the present invention has been completed.

Thus, the present invention provides the following.
(1) 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid and 10 milkfat feeling or fat feeling aroma consisting of one or more dodecene selected from the group consisting of acid and / or milk fat feeling or oil A fragrance improving agent.
(2) The fragrance and / or flavor improver of (1) is based on one or more selected from the group consisting of 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid and 10-dodecenoic acid As a fragrance composition for improving the feeling of milk fat or oil containing 0.1 ppm to 10% .
(3 ) A fragrance comprising 0.1 ppm to 10% of one or more selected from the group consisting of 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid and 10-dodecenoic acid. A method for improving a milky or oily fragrance of a composition.
( 4 ) One kind selected from the group consisting of 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid and 10-dodecenoic acid for the flavor improver of (1) or the fragrance composition of (2) for food and drink or two or more of Ru was added 1Ppb～0.1%, based, milk fat feeling or fat feeling flavor improvement methods food or drink.
( 5 ) One type selected from the group consisting of 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid and 10-dodecenoic acid, in which the fragrance improving agent of (1) or the fragrance composition of (2) is used in cosmetics or two or more of Ru was added 1Ppb～0.1% based aroma improvement method for imparting a natural feeling of cosmetic.

  The 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid or 10-dodecenoic acid of the present invention can improve the aroma and flavor such as milky feeling and oily feeling in the fragrance composition, and the scent persistence. And by adding a fragrance composition containing 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid or 10-dodecenoic acid to foods and drinks, etc., aroma and flavor such as milky fat feeling and oily feeling Can be improved, and the sustainability of the fragrance can be improved, and it is possible to provide a variety of foods and drinks that match the taste of consumers.

  Hereinafter, the present invention will be described in more detail.

  The compound of the present invention, 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid or 10-dodecenoic acid may be a mixture of (E) isomer and (Z) isomer, or (E) isomer or (Z ) Even the body alone has the effect of the present invention.

  The compound of the present invention, 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid or 10-dodecenoic acid, can be produced, for example, according to the reaction pathway shown below.

  In the reaction step, an unsaturated fatty acid having a double bond at the terminal is used as a raw material and esterified using an acid catalyst such as an arbitrary alcohol and para-toluenesulfonic acid to obtain an aldehyde by ozone oxidation. A Wittig reaction between the obtained aldehyde and the phosphorus ylide obtained from the phosphonium salt is carried out, and the resulting dodecenoic acid ester is subjected to alkaline hydrolysis, whereby 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid or 10 -Dodecenoic acid can be produced.

  Hereinafter, although a general manufacturing method is described about each process, this invention is not limited.

  The unsaturated fatty acid used as a starting material for the above reaction may be either one synthesized according to a general method or a commercially available product. As commercial products, 7-octenoic acid (manufactured by Sigma-Aldrich), 8-nonenoic acid (manufactured by Sigma-Aldrich), 9-decenoic acid (manufactured by Sigma-Aldrich), 10-undecenoic acid (Sigma-Aldrich) Manufactured).

  An unsaturated fatty acid ester can be produced by reacting an unsaturated fatty acid represented by the above reaction formula with an alcohol in the presence of p-toluenesulfonic acid. The alcohol is not limited as long as it is a saturated aliphatic alcohol, but methanol or ethanol is particularly preferable.

  The aldehyde shown by the said Reaction Formula can be manufactured by blowing ozone in the obtained unsaturated fatty acid ester on the conditions of -50 degreeC--30 degreeC by using methylene chloride as a solvent.

  The obtained aldehyde can be subjected to a Wittig reaction using a Wittig reagent in the presence of N, N-dimethylformamide and sodium alcoholate to produce a dodecenoic acid ester. The sodium alcoholate used for the Wittig reaction is not particularly limited, but sodium methoxide or sodium ethoxide is preferably used. Examples of the Wittig reagent used for the Wittig reaction include ethyltriphenylphosphonium halide, propyltriphenylphosphonium halide, butyltriphenylphosphonium halide, and pentyltriphenylphosphonium halide.

  The obtained dodecenoic acid ester can produce the dodecenoic acid of the present invention by alkaline hydrolysis in the presence of an aqueous sodium hydroxide solution and an alcohol. The alcohol is not particularly limited as long as it is an aliphatic saturated alcohol, but methanol or ethanol is desirable.

  The compound of the present invention, 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid or 10-dodecenoic acid, is directly incorporated into foods and drinks or cosmetics to improve aroma and flavor such as milky feeling and oily feeling. In addition, the perfume persistence can be increased, but a perfume composition is prepared by mixing with other ingredients, and the perfume composition is blended into a food or drink product or cosmetic product, thereby giving a sense of milkiness or oiliness. It is also possible to improve the fragrance and flavor, and to increase the persistence of the scent. Furthermore, 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid or 10-dodecenoic acid of the present invention can be used in a mixture of two or more in any ratio, and can be mixed with other perfume ingredients. Can be used.

  The content of the 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid, 10-dodecenoic acid, or a mixture of two or more of the present invention in the fragrance composition depends on the purpose or the type of the fragrance composition. However, it is 0.1 ppm to 10%, preferably 0.2 ppm to 5%, more preferably 0.5 ppm to 2%, more preferably 1 ppm to 1%, particularly preferably based on the total mass of the fragrance composition. A range of 2 ppm to 0.5% can be exemplified. Within these ranges, the perfume composition has an excellent effect of improving aroma and flavor such as milky feeling and oily feeling. On the other hand, when the content with respect to the fragrance composition exceeds 10%, the odor and flavor characteristics such as uri-like and green-like characteristic of the compound are strongly exerted, which is not preferable. Moreover, when content with respect to a fragrance | flavor composition is less than 0.1 ppm, the fragrance and flavor improvement effect peculiar to this invention are not acquired.

  Examples of other fragrance ingredients that can be contained together with 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid or 10-dodecenoic acid in the fragrance composition include various synthetic fragrances, natural fragrances, natural essential oils, plant extracts, and the like. Can be mentioned. For example, natural essential oils, natural fragrances, and synthetic fragrances described in “Patent Office, Well-known and commonly used technology collection (fragrance) Part II food fragrances” or “Synthetic fragrances, chemistry and product knowledge, augmented new edition, published by Chemical Industry Daily” Can be mentioned.

  For example, γ-caprolactone, γ-heptalactone, γ-octalactone, γ-nonalactone, γ-decalactone, 7-decen-4-olide, 3-methyl-4-decen-4-olide, 3-methyl-5- Decene-4-olide, γ-undecalactone, γ-dodecalactone, γ-tridecalactone, γ-tetradecalactone, δ-caprolactone, 2-hexene-5-olide, 2-heptene-5-olide, δ -Octalactone, 2-octene-5-olide, 4-methyl-5-octanolide, δ-nonalactone, 2-nonene-5-olide, 4-methyl-5-nonanolide, δ-decalactone, 2-decene-5 Orido, 4-methyl-5-decanolide, δ-undecalactone, 2-undecen-5-olide, 4-methyl-5-undecanolide, δ-dodecalactone 2-dodecene-5-olide, 4-methyl-5-dodecanolide, δ-tridecalactone, 2-tridecen-5-olide, 4-methyl-5-tridecanolide, δ-tetradecalactone, 2-tetradecene-5 Orido, 2-Pentadecene-5-Olide, 2-Hexadecene-5-Olide, 2-Heptadecene-5-Olide, 2-Octadecene-5-Olide, 2-Nonadecene-5-Olide, 2-Eicosene-5-Olide, Lactones such as ε-decalactone; formic acid, propionic acid, butyric acid, valeric acid, isovaleric acid, caproic acid, trans-2-hexenoic acid, heptanoic acid, caprylic acid, nonanoic acid, 5-hydroxynonanoic acid, capric acid, 2-decenoic acid, 4-decenoic acid, 5-decenoic acid, 6-decenoic acid, 9-decenoic acid, 5-hydroxydecenoic acid, 5-hydroxysulfuric acid Fatty acids such as decanoic acid, lauric acid, 5-hydroxydodecanoic acid, myristic acid, pentadecanoic acid, isopentadecanoic acid, palmitic acid, heptadecanoic acid, stearic acid, oleic acid, linoleic acid, linolenic acid; acetaldehyde, propanal, butanal 2-butenal, hexanal, octanal, 4-heptenal, 2,4-octadienal, nonanal, 2-nonenal, 2,4-nonadienal, 2,6-nonadienal, decanal, 2,4-decadienal, undecanal, Aldehydes such as 2,4-undecadienal, dodecanal, benzaldehyde, vanillin, ethyl vanillin, furfural; ethyl formate, ethyl acetate, butyl acetate, isoamyl acetate, decyl acetate, dodecyl acetate, phenethyl acetate, milk Ethyl acetate, ethyl butyrate, ethyl 2-methylbutyrate, ethyl 3-ethylbutyrate, methyl valerate, methyl caproate, ethyl caproate, methyl heptanoate, ethyl heptanoate, ethyl caprylate, isoamyl caprylate, heptyl caprylate, Methyl nonanoate, ethyl nonanoate, methyl caprate, ethyl caprate, ethyl undecanoate, methyl laurate, ethyl laurate, ethyl myristate, ethyl palmitate, methyl salicylate, diethyl succinate, diethyl sebacate, 5-hydroxy Ethyl hexanoate, ethyl 5-hydroxydecanoate, ethyl 5-hydroxyundecanoate, propyl 5-hydroxydecanoate, isopropyl 5-hydroxydecanoate, 2-methylpropyl 5-hydroxyoctanoate, 5-hydroxy-9-methyl Esters such as ethyl canate, methyl 5-acetoxydecanoate, ethyl 5-acetoxydecanoate; ethanol, propanol, butanol, pentanol, hexanol, heptanol, octanol, nonanol, decanol, benzyl alcohol, phenylethyl alcohol, furfuryl Alcohols such as alcohol; 2-heptanone, 2-octanone, 3-octanone, 1-octen-3-one, 2-nonanone, 3-nonanone, 8-nonen-2-one, 2-undecanone, 2-tridecanone, Acetoin, 5-hydroxy-4-octanone, diacetyl, 2,3-pentadione, 2,3-hexadione, 2,3-heptadione, acetylisovaleryl, p-methoxyacetophenone, benzophenone, maltol, 3-hydroxy 2-methyl-4H-pyran-4-one, 2-ethyl-3-hydroxy-4H-pyran-4-one, 2,5-dimethyl-4-hydroxy-3 (2H) -furanone, 3-methyl- 1,2-cyclopentanedione, 3-ethyl-1,2-cyclopentanedione, 3-hydroxy-4,5-dimethyl-2 (5H) -furanone, 5-ethyl-3-hydroxy-4-methyl-2 Ketones such as (5H) -furanone, 2-ethyl-4-hydroxy-5-methyl-3 (2H) -furanone, 3,4-dimethyl-1,2-cyclopentanedione; methyl anthranilate, ethylan Nitrogen-containing compounds such as tranilate, phenylethylanthranylate, trimethylamine, indole, skatole, pyridine, isoquinoline, pyrazine, methylpyrazine; Tanthiol, isobutyl mercaptan, 2,4-dithiapentane, dimethyl sulfide, dimethyl disulfide, dimethyl trisulfide, dimethyl sulfoxide, dimethyl sulfone, methylsulfonyl methane, methyl isothiocyanate, ethyl isothiocyanate, allyl isothiocyanate, 2-methyl-3 -Butanethiol, methional, ethyl thioacetate, methyl thiobutyrate, 3-butenyl isothiocyanate, 2-methylthiophene, benzothiazole, sulfuryl, acetyl lactate thiomethyl ester, propionyl lactate thiomethyl ester, butyryl lactate thiomethyl ester, valeryl Lactic acid thiomethyl ester, 2-methylbutyryl lactate thiomethyl ester, desilyl lactate thiomethyl ester, acetyl lactate thioethyl ester And the like known fragrance compounds, esters, propionyl lactate thioethyl ester, butyryl lactate thioethyl ester, valeryl lactate thioethyl ester, sulfur-containing compounds such as isocaproyl lactic thio propyl ester.

  In the fragrance composition containing 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid or 10-dodecenoic acid of the present invention, or a mixture of two or more thereof, it is usually used in the fragrance composition as necessary. Used solvents such as water and ethanol; ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, glycerin, hexylene glycol, benzyl benzoate, triethyl citrate, diethyl phthalate, hercoline, fatty acid triglyceride, fatty acid diglyceride, etc. Perfume retention agent.

  In addition, for example, one or more emulsifiers or stabilizers such as quinaya extract, enzyme-treated lecithin, sucrose fatty acid ester, polyglycerin fatty acid ester, glycerin fatty acid ester, gum arabic, In addition, emulsification using a homomixer, a colloid mill, a high-pressure homogenizer, or the like can be used to form an emulsified flavor preparation. The amount of the emulsifier or stabilizer used varies depending on the type of the emulsifier or stabilizer, but is, for example, in the range of 0.1 to 25% by weight, preferably in the range of 5 to 20% by weight, based on the mass of the emulsified fragrance preparation. Can be mentioned.

  Furthermore, for example, the emulsified fragrance preparation includes sugars such as sugar, lactose, glucose, trehalose, cellobiose, starch syrup, and reduced starch syrup; sugar alcohols; various starch degradation products such as dextrin and starch derivatives, starch, gelatin, gum arabic, etc. After an excipient such as natural gum is appropriately blended, it can be dried by an appropriate drying means such as spray drying or vacuum drying to form a powder flavor preparation. The blending amount of these excipients can be appropriately selected according to the properties desired for the powdered fragrance preparation.

  The 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid or 10-dodecenoic acid of the present invention may be used alone as described above, or a perfume composition containing two or more of these may be prepared. Thus, by adding it to foods and beverages or cosmetics, it is possible to improve the aroma such as milk fat feeling and oily feeling, making use of the above-mentioned aroma characteristics, and to enhance the scent sustainability.

  The fragrance composition containing the 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid or 10-dodecenoic acid of the present invention, or a mixture of two or more thereof improves the aroma such as milk fat feeling and oily feeling. In addition, specific examples of foods and drinks that can enhance the sustainability of the scent are not limited at all. For example, carbonated drinks such as cola drink, carbonated drink with fruit juice, carbonated drink with milk; fruit juice drink , Vegetable drinks, sports drinks, honey drinks, soy milk, vitamin supplement drinks, mineral supplement drinks, nutrition drinks, nourishment drinks, lactic acid bacteria drinks, milk drinks and other soft drinks; green tea, tea, oolong tea, herbal tea, milk tea, coffee Taste beverages such as beverages; Chuhai, cocktail drinks, alcoholic beverages such as happoshu, fruit liquor, and condiments; butter, cheese Dairy products such as milk and yogurt; desserts such as ice cream, lacto ice, ice confectionery, yogurt, pudding, jelly, daily dessert and mixes for producing them; caramel, candy, tablet confectionery, crackers, biscuits, donuts, Cookies, cakes, pie, chocolate, snacks, confections such as butter cream, custard cream, cream puffs, etc. and mixes such as cake mixes for producing them; fats and oils such as sesame oil, soybean oil, rapeseed oil, lard; chicken, Livestock meat such as pork, beef, lamb and horse meat; curry, stew, beef stew, hayashi rice sauce, meat sauce, mabo tofu, hamburger, dumplings, pot rice, soups, meat dumplings, simmered meat, canned meat, etc. Processed foods and beverages used: bread, It can be mentioned; Don, noodles, Chinese noodles, sushi, dish of rice, fried rice, pilaf, okonomiyaki, breads, such as takoyaki, noodles, Gohanrui.

  The fragrance composition containing 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid, 10-dodecenoic acid, or a mixture of two or more thereof according to the present invention improves the aroma and enhances the persistence of the scent. Specific examples of cosmetics that can be used include, but are not limited to, for example, perfumes; hair care products such as shampoos, rinses, hair styling (hair creams, pomades, etc.); foundations, lipsticks, lip balms, lip glosses, Cosmetics such as skin lotion, cosmetic emulsion, cosmetic cream, cosmetic gel, cosmetic liquid, pack agent; tanned cosmetics such as suntan products and sunscreen products; facial soap, body soap, laundry soap, laundry Health and hygiene detergents such as detergents, disinfectants and deodorants; toothpaste, tissue paper, toilet paper, etc. Health and sanitation materials such; room fragrance, can be exemplified aromatic products such Kakoron.

  Moreover, it does not restrict | limit especially as a form of cosmetics. For example, the present invention can be applied to various forms such as liquid, emulsion, cream, paste, solid, and multilayer. Besides these, it can be applied as a sheet agent, a spray agent, and a mousse agent.

  The amount of 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid, 10-dodecenoic acid, or a mixture of two or more of the present invention varies depending on the purpose or the type of food or drink or cosmetic product. For example, the range of 1 ppb to 0.1%, preferably 2 ppb to 500 ppm, more preferably 5 ppb to 200 ppm, more preferably 10 ppb to 100 ppm, and particularly preferably 20 ppb to 50 ppm with respect to the total weight of the food or drink or cosmetic. It can be illustrated. Within these ranges, it has an excellent effect of improving aroma and flavor such as milky feeling and oily feeling for foods and drinks or cosmetics. On the other hand, when the blending amount with respect to foods and drinks or cosmetics exceeds 0.1%, the compound-like cucumber-like, green-like aroma / flavor characteristics are strong, which is not preferable. Moreover, when the compounding quantity with respect to food-drinks or cosmetics is less than 1 ppb, the fragrance and flavor improvement effect peculiar to this invention cannot be acquired.

  Hereinafter, the present invention will be described more specifically with reference to examples. The present invention is not limited to these.

Example 1: Synthesis of 7-dodecenoic acid In a 50 mL eggplant flask, 7-octenoic acid (Sigma-Aldrich, 1.0 g, 7.0 mmol), p-toluenesulfonic acid monohydrate and methanol (20 mL) were added. The mixture was stirred and stirred for 3 hours while dehydrating under reflux. A saturated aqueous sodium carbonate solution was added at room temperature, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium carbonate solution, water, and saturated brine, dried over magnesium sulfate, filtered, and then concentrated to obtain methyl 7-octenoate.

  To a 100 mL three-necked flask, methyl 7-octenoate and methylene chloride (20 mL) were charged, and ozone was blown at −50 to −30 ° C. After 1 hour, when the reaction solution turned blue, the temperature was raised to room temperature, and dimethyl sulfide was gradually added (about 1 mL). After stirring at room temperature for 30 minutes, the mixture was concentrated and diluted with ether. The organic layer was washed with water, dried over magnesium sulfate, filtered, and then concentrated to obtain methyl 7-oxoheptanoate.

  A 100 mL three-necked flask was charged with methyl 7-oxoheptanoate, N, N-dimethylformamide (50 mL), pentyltriphenylphosphonium bromide (5.8 g, 14.1 mmol), and sodium methoxide (28% methanol solution, 2. 71 g, 14.06 mmol) was added and stirred for 2 hours. Water was added at room temperature and extracted with ether. The organic layer was washed with water, saturated aqueous ammonium chloride solution, water and saturated brine, dried over magnesium sulfate, filtered, and concentrated to give methyl 7-dodecenoate.

  To a 30 mL eggplant flask, methyl 7-dodecenoate and methanol (10 mL) were charged, 25% aqueous sodium hydroxide solution (2.0 g) was added, and the mixture was stirred at 40 ° C. for 1 hr. The reaction solution was concentrated, water was added, acidified with concentrated sulfuric acid, and extracted with ether. The organic layer was washed with water and saturated brine, dried over magnesium sulfate, filtered, and concentrated. The concentrate was purified by silica gel column chromatography (hexane: ethyl acetate = 10: 1) to obtain 7-dodecenoic acid (product of the present invention 1: 132 mg, cis / trans isomer ratio 90:10).

Example 2: Synthesis of 8-dodecenoic acid In a 50 mL eggplant flask, 8-nonenoic acid (manufactured by Sigma-Aldrich, 1.0 g, 6.4 mmol), p-toluenesulfonic acid monohydrate and methanol (15 mL) were added. The mixture was stirred and stirred for 1 hour while dehydrating under reflux. A saturated aqueous sodium carbonate solution was added at room temperature, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium carbonate solution, water, and saturated brine, dried over magnesium sulfate, filtered, and then concentrated to obtain methyl 8-nonenate.

  A 100 mL three-necked flask was charged with methyl 8-nonenoate and methylene chloride (20 mL), and ozone was blown at −50 to −30 ° C. After 1 hour, when the reaction solution turned blue, the temperature was raised to room temperature, and dimethyl sulfide was gradually added (about 1 mL). After stirring at room temperature for 30 minutes, the mixture was concentrated and diluted with ether. The organic layer was washed with water, dried over magnesium sulfate, filtered and then concentrated to obtain methyl 8-oxooctanoate.

  A 100 mL three-necked flask was charged with N, N-dimethylformamide (30 mL) and butyltriphenylphosphonium bromide (5.1 g, 12.8 mmol), and methyl 8-oxooctanoate was added, followed by sodium methoxide (28% methanol). Solution, 2.5 g, 12.8 mmol) was added and stirred for 2 hours. Water was added at room temperature and extracted with ether. The organic layer was washed with water, saturated aqueous ammonium chloride solution, water and saturated brine, dried over magnesium sulfate, filtered, and concentrated to give methyl 8-dodecenoate.

  To a 30 mL eggplant flask, methyl 8-dodecenoate and methanol (10 mL) were added, 25% aqueous sodium hydroxide solution (2.0 g) was added, and the mixture was stirred at 40 ° C. for 3 hr. The reaction solution was concentrated, water was added, acidified with concentrated sulfuric acid, and extracted with ether. The organic layer was washed with water and saturated brine, dried over magnesium sulfate, filtered, and concentrated. The concentrate was purified by silica gel column chromatography (hexane: ethyl acetate = 10: 1) to obtain 8-dodecenoic acid (product of the present invention 2: 147 mg, cis / trans isomer ratio 92: 8).

Example 3: Synthesis of 9-dodecenoic acid A 30 mL eggplant flask was charged with 9-decenoic acid (Sigma-Aldrich, 2.0 g, 11.8 mmol), p-toluenesulfonic acid monohydrate and methanol (10 mL). The mixture was stirred and stirred for 2 hours while dehydrating under reflux. A saturated aqueous sodium carbonate solution was added at room temperature, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium carbonate solution, water, and saturated brine, dried over magnesium sulfate, filtered, and concentrated to give methyl 9-decenoate.

  A 200 mL three-necked flask was charged with methyl 9-decenoate and methylene chloride (30 mL), and ozone was blown at −50 to −30 ° C. After 1 hour, when the reaction solution turned blue, the temperature was raised to room temperature, and dimethyl sulfide was gradually added (about 2 mL). The mixture was stirred at room temperature for 30 minutes and concentrated to give methyl 9-oxononanoate.

  A 100 mL three-necked flask was charged with methyl 9-oxononanoate, N, N-dimethylformamide (50 mL), propyltriphenylphosphonium bromide (9.05 g, 23.5 mmol), and sodium methoxide (28% methanol solution, 4.53 g). , 23.5 mmol) was added and stirred for 2 hours. Water was added at room temperature and extracted with ether. The organic layer was washed with water, saturated aqueous ammonium chloride solution, water and saturated brine, dried over magnesium sulfate, filtered, and concentrated to give methyl 9-dodecenoate.

  To a 50 mL eggplant flask, methyl 9-dodecenoate and methanol (30 mL) were added, 25% aqueous sodium hydroxide solution (4.0 g) was added, and the mixture was stirred at 40 ° C. for 3 hr. The reaction solution was washed with toluene, the aqueous layer was acidified with concentrated sulfuric acid, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over magnesium sulfate, filtered, and concentrated. The concentrate was purified by silica gel column chromatography (hexane: ethyl acetate = 10: 1) to obtain 9-dodecenoic acid (product of the present invention 3: 218 mg, cis / trans isomer ratio 84:16).

Example 4: Synthesis of 10-dodecenoic acid In a 30 mL eggplant flask, 10-undecenoic acid (Sigma-Aldrich, 2.0 g, 10.9 mmol), p-toluenesulfonic acid monohydrate and ethanol (15 mL) were added. The mixture was stirred and stirred for 1 hour while dehydrating under reflux. Water was added at room temperature and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and water, dried over magnesium sulfate, filtered, and then concentrated to obtain ethyl 10-undecenoate.

  A 100 mL 3-neck flask was charged with ethyl 10-undecenoate and methylene chloride (40 mL), and ozone was blown at −40 to −30 ° C. After 1 hour, when the reaction solution turned blue, the temperature was raised to room temperature, and dimethyl sulfide was gradually added (about 2 mL). The mixture was stirred at room temperature for 30 minutes and concentrated to obtain ethyl 10-oxodecanoate.

  A 100 mL three-necked flask was charged with ethyl 10-oxodecanoate, N, N-dimethylformamide (30 mL), ethyltriphenylphosphonium bromide (8.1 g, 21.7 mmol), and sodium ethoxide (1.5 g, 21.7 mmol). Was added and stirred for 2 hours. Water was added at room temperature and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium carbonate solution, a saturated aqueous ammonium chloride solution and water, dried over magnesium sulfate, filtered, and then concentrated to obtain ethyl 10-dodecenoate.

  A 50 mL eggplant flask was charged with ethyl 10-dodecenoate and methanol (10 mL), 25% aqueous sodium hydroxide solution (4.0 g) was added, and the mixture was stirred at room temperature overnight. The reaction solution was washed with toluene, the aqueous layer was acidified with concentrated sulfuric acid, and extracted with ether. The organic layer was washed with water and saturated brine, dried over magnesium sulfate, filtered and concentrated. The concentrate was purified by silica gel column chromatography (hexane: ethyl acetate = 10: 1) to obtain 10-dodecenoic acid (product of the present invention 4: 498 mg, cis / trans isomer ratio 89:11).

Example 5: Evaluation of aroma 7-dodecenoic acid (product 1 of the present invention), 8-dodecenoic acid (product 2 of the present invention), 9-dodecenoic acid (product 3 of the present invention), 10-dodecenoic acid (present invention) Each 0.1% triacetin solution of product 4) was evaluated for fragrance by five well-trained panelists. The fragrance evaluation was carried out using the above-described 0.1% triacetin solution and smelling paper impregnated with the fragrance of the bottle mouth and the solution. Table 1 shows the average aroma evaluation of five people.

Example 6: Effect of addition to a milk-like blended fragrance composition Each component (mass%) in Table 2 was formulated as a milk-like blended fragrance composition. A novel milk-like blended fragrance composition was prepared by mixing 2.0 g of the present invention products 1-4 with the milk-like blended fragrance composition (Comparative Product 1) in Table 2. The inventive products 5 to 8 and the comparative product 1 in which the inventive products 1 to 4 were mixed were subjected to sensory evaluation by 10 well-trained panelists.

  As a result, all 10 panelists evaluated that the inventive products 5 to 8 have improved milk fat feeling, a rich feeling unique to milk fat, and a high fragrance sustainability compared to the comparative product 1. .

Example 7: Effect of addition to a butter-like blended fragrance composition Each component (mass%) in Table 3 was formulated as a butter-like blended fragrance composition. The novel butter-like blended fragrance composition was prepared by mixing 5.0 g of the present invention products 1 to 4 with the butter-like blended fragrance composition shown in Table 3 (Comparative product 2). The inventive products 9 to 12 and the comparative product 2 in which the inventive products 1 to 4 were mixed were subjected to sensory evaluation by 10 well-trained panelists.

  As a result, all 10 panelists said that the products 9 to 12 of the present invention have a better oily feeling, a unique oily feel, and a high fragrance sustainability compared to the comparative product 2. evaluated.

Example 8: Effect of Addition to Milk-like Formulated Perfume Formulation for Each Concentration of Invention Product 1 A milk-like flavor composition was prepared according to the milk-like formulated perfume formulation (mass%) shown in Table 4.

  That is, Comparative Product 3 contains 10 ppb of 7-dodecenoic acid of Product 1 of the present invention. Similarly, Example 13 is 0.1 ppm of Product 1 of the present invention, Example 14 is 1 ppm of Product 1 of the present invention, and Example 15 The present invention product 1 is 10 ppm, Example 16 is the present product 1 0.1 mass%, Example 17 is the present invention 1 1 mass%, Example 18 is the present invention 1 10 mass%, comparison The product 4 contains 20% by mass of the product 1 of the present invention. Each milk-like fragrance composition was subjected to sensory evaluation by 10 panelists who were well trained.

  The sensory evaluation was performed using an index for enhancing the feeling of milk fat and maintaining the fragrance. Regarding enhancement of milk fat feeling, 0: no change from the control product, 1: slightly milk fat feeling compared to the control product, 2: milk fat feeling compared to the control product, 3: stronger than the control product There was a feeling of milk fat, -1: It was scored that the fragrance of uri-like was too strong compared with the control product, and the balance of the feeling of milk fat was bad.

  In addition, regarding the persistence of the scent, the milk-like fragrance compositions of Comparative Products 3 and 4 and Invention Products 13 to 18 were attached to the tip of the scented paper, and the scent after being left for 3 minutes was compared. 0: The smell was not felt, 1: The smell is considerably weaker than immediately after it is applied, 2: The smell is weaker than immediately after it is applied, 3: The smell is compared with immediately after it is applied Scoring as not weakening so much.

  Table 5 shows the sensory evaluation of the milk-like fragrance compositions of Comparative Products 3 and 4 and Invention Products 13 to 18.

  From the results shown in Table 5, the products 13 to 18 of the present invention have enhanced milk fat feeling, imparted a rich and rich creamy body feeling, and markedly emphasized a good milk-like aroma. On the other hand, the comparative product 3 was not much different from the control product 1, and the comparative product 4 was evaluated as green and cucumber-like were too strong and the original flavor of milk was lost.

  Moreover, from the result of Table 5, this invention products 13-18 were evaluation that aroma was not weakened extremely. Although the comparative product 4 had the persistence of the fragrance, the fragrance itself was evaluated as having lost the original fragrance of milk.

Example 9: Effect of Addition to Milk-like Formulation Perfume Formulation for Each Concentration of Invention Product 2 A milk-like flavor composition was prepared according to the milk-like formula perfume formulation (mass%) shown in Table 6.

  That is, the comparative product 5 contains 10 ppb of 8-dodecenoic acid of the product 2 of the present invention. Similarly, Example 19 has 0.1 ppm of the product 2 of the present invention, Example 20 has 1 ppm of the product 2 of the present invention, and Example 21. The present invention product 2 is 10 ppm, Example 22 is the present invention product 2 0.1 mass%, Example 23 is the present invention product 2 1 mass%, Example 24 is the present invention product 2 10 mass%, comparison The product 6 contains 20% by mass of the product 2 of the present invention. Each milk-like fragrance composition was subjected to sensory evaluation by 10 panelists who were well trained.

  In addition, the sensory evaluation method was implemented by the method similar to Example 8. FIG. Table 7 shows the sensory evaluation of the milk-like fragrance compositions of Comparative Products 5 and 6 and Invention Products 19 to 24.

  From the results shown in Table 7, the inventive products 19 to 24 have enhanced milk fat feeling, imparted a rich and rich creamy body feeling, and markedly emphasized a good milk-like aroma. On the other hand, the comparative product 5 was not much different from the control product 1, and the comparative product 6 was evaluated as green and cucumber-like being too strong, and the original flavor of milk was lost.

  Moreover, from the result of Table 7, this invention products 19-24 were evaluation that aroma was not weakened extremely. Although the comparative product 6 had the persistence of the fragrance, the fragrance itself was evaluated as having lost the original fragrance of milk.

Example 10: Effect of Addition to Milk-like Formulated Perfume Formulation for Each Concentration of Invention Product 3 A milk-like flavor composition was prepared according to the milk-like formulated perfume formulation (mass%) shown in Table 8.

  That is, Comparative Product 7 contains 10 ppb of 9-dodecenoic acid of Product 3 of the invention. Similarly, Example 25 is 0.1 ppm of Product 3 of the present invention, Example 26 is 1 ppm of Product 3 of the invention, and Example 27. The present invention product 3 is 10 ppm, Example 28 is the present invention product 3 0.1 mass%, Example 29 is the present invention product 3 1 mass%, Example 30 is the present invention product 3 10 mass%, comparison The product 8 contains 20% by mass of the product 3 of the present invention. Each milk-like fragrance composition was subjected to sensory evaluation by 10 panelists who were well trained.

  In addition, the sensory evaluation method was implemented by the method similar to Example 8. FIG. Table 9 shows the sensory evaluation of the milk-like fragrance compositions of Comparative Products 7 and 8 and Invention Products 25-30.

  From the results of Table 9, the inventive products 25 to 30 have enhanced milk fat feeling, imparted a rich and rich creamy body feeling, and markedly emphasized a good milk-like aroma. No. 7 was not much different from the control product 1, and the comparative product 8 was evaluated as green and cucumber-like were too strong and the original flavor of milk was lost.

  Moreover, from the result of Table 9, this invention products 25-30 were evaluation that aroma was not weakened extremely. Although the comparative product 8 had the persistence of the fragrance, the fragrance itself was evaluated as having lost the original fragrance of milk.

Example 11: Effect of Addition to Milk-like Formulated Perfume Formulation for Each Concentration of Invention Product 4 A milk-like flavor composition was prepared according to the milk-like formulated flavor formula (mass%) shown in Table 10.

  That is, the comparative product 9 contains 10 ppb of 10-dodecenic acid of the product 4 of the present invention. Similarly, Example 31 is 0.1 ppm of the product 4 of the present invention, Example 32 is 1 ppm of the product 4 of the present invention, and Example 33. The present invention product 4 is 10 ppm, Example 34 is the present invention product 4 0.1 mass%, Example 35 is the present invention product 1 1 mass%, Example 36 is the present invention product 4 10 mass%, comparison The product 10 contains 20% by mass of the product 4 of the present invention. Each milk-like fragrance composition was subjected to sensory evaluation by 10 panelists who were well trained.

  In addition, the sensory evaluation method was implemented by the method similar to Example 8. FIG. Table 11 shows the sensory evaluation of the milk-like fragrance compositions of Comparative Products 9 and 10 and Invention Products 31 to 36.

  From the results shown in Table 11, the products 31 to 36 of the present invention have enhanced milk fat feeling, a rich and rich creamy body feeling, and a good milk-like aroma is remarkably emphasized. On the other hand, the comparative product 9 was not much different from the control product 1, and the comparative product 10 was evaluated as green and cucumber-like being too strong and the original flavor of milk was lost.

  Moreover, from the result of Table 11, this invention products 31-36 were evaluation that aroma was not weakened extremely. Although the comparative product 10 had the persistence of the fragrance, the fragrance itself was evaluated as having lost the original fragrance of milk.

Example 12: Effect of addition to a butter-like blended fragrance formulation for each concentration of the inventive product 3 A butter-like fragrance composition (control product 2) was prepared according to the butter-like blended fragrance formulation (mass%) shown in Table 12.

  That is, Comparative Product 11 contains 10 ppb of 9-dodecenoic acid of Invention Product 3, and similarly, Example 37 has 0.1 ppm of Invention Product 3, Example 38 has 1 ppm of Invention Product 3, and Example 39. Inventive product 3 is 10 ppm, Example 40 is 0.1 mass% of the inventive product 3, Example 41 is 1 mass% of the inventive product 3, Example 42 is 10 mass% of the inventive product 3, and comparison The product 12 contains 20% by mass of the product 3 of the present invention. Each butter-like fragrance composition was subjected to sensory evaluation by 10 panelists who were well trained.

  The sensory evaluation was performed using an index for enhancing the sense of oil and fat and maintaining the fragrance. Regarding enhancement of oil and fat feeling, 0: no change from control product, 1: slightly oily feeling compared to control product, 2: oiliness compared to control product, 3: stronger than control product There was a sense of oil and fat. -1: The score was determined to be too strong for the uri-like aroma to be inferior to the balance of the control product.

  In addition, regarding the persistence of the scent, the comparison products 11 and 12 and the butter-like fragrance composition of the present invention products 37 to 42 were attached to the leading edge of the odor paper, and the odor after being applied for 3 minutes was compared. 0: The smell was not felt, 1: The smell is considerably weaker than immediately after it is applied, 2: The smell is weaker than immediately after it is applied, 3: The smell is compared with immediately after it is applied Scoring as not weakening so much.

  Table 13 shows the sensory evaluation of the butter-like fragrance compositions of Comparative Products 11 and 12 and Invention Products 37 to 42.

  From the results shown in Table 13, the inventive products 37 to 42 have enhanced oil and fat feeling, a rich and rich body feeling, and a good butter-like fragrance. On the other hand, the comparative product 11 was not much different from the control product 2, and the comparative product 12 was evaluated as green and cucumber-like being too strong, and the original aroma of butter was lost.

  Moreover, from the result of Table 13, this invention products 37-42 were evaluation that aroma was not weakened extremely. Although the comparative product 12 had fragrance persistence, the fragrance itself was evaluated as having lost the original fragrance of butter.

Example 13: Effect of adding milk-like formulated fragrance composition to milk tea The milk-like formulated fragrance composition obtained in Example 6 (Comparative product 1, products 5-8 of the present invention) was prepared according to the formulation in Table 14. Milk tea beverage was prepared by a conventional method. Milk tea to which Comparative Product 1 and Invention Products 5 to 8 were added was referred to as Comparison Product 13 and Invention Products 43 to 46, respectively. These milk teas were subjected to sensory evaluation by 20 well-trained panelists.

  As a result, all 20 panelists evaluated that the products 43 to 46 of the present invention had better milk fat feeling and body feeling and the milk-like aroma was enhanced as compared with the comparative product 13.

Example 14: Effect of addition of butter-like blended fragrance composition to cookies The butter-like blended fragrance composition obtained in Example 7 (Comparative Product 2, Invention Products 9 to 12) was prepared according to the formulation in Table 15. Added to the cookie dough and baked cookies at 220 ° C. for 7 minutes to prepare. The cookies to which Comparative Product 2 and Invention Products 9 to 12 were added were referred to as Comparison Product 14 and Invention Products 47 to 50, respectively. These cookies were subjected to sensory evaluation by 20 well-trained panelists.

  As a result, all 20 panelists were evaluated that the inventive products 47 to 50 were given a unique oil and fat feeling compared to the comparative product 14, and the aroma and flavor of the butter-rich image were emphasized. .

Example 15: Effect of addition to pork bone ramen soup According to the formulation of Table 16, a powder composition for pork bone ramen was prepared.

  10 g of the above pork bone ramen powder composition was diluted with hot water (70 ° C.) to make a total of 1000 ml of pork bone ramen soup as comparative product 15. Further, after diluting with hot water, 0.1 g of a 0.1% solution of 9-dodecenoic acid (Product 3 of the present invention) diluted with alcohol and water was added, and further diluted with hot water to make a total of 1000 ml. Pork bone ramen soup was designated as Product 51 of the present invention. Sensory evaluation was performed by 20 panelists who were well trained for the comparative product 15 and the product 51 of the present invention.

  As a result, all 20 panelists evaluated that the product 51 of the present invention can impart a sustained creamy flavor as compared with the comparative product 15, and the richness of the pork bone is enhanced.

Example 16: Effect of addition to non-alcohol beer Non-alcohol beer was prepared according to the formulation in Table 17.

  20 panelists who were well trained on the comparative product 16 used in Example 15 to which the 9-dodecenoic acid 0.1% solution was not added and the product 52 of the present invention to which the 9-dodecenoic acid 0.1% solution was added were used. Evaluation was performed.

  As a result, all 20 panelists evaluated that the inventive product 52 felt a body feeling in the aftertaste compared to the comparative product 16, and the richness and thickness peculiar to beer were enhanced.

Example 17: Effect of addition to Mugue-like blended fragrance composition Each component (mass%) in Table 18 was formulated as a Mugue-like blended fragrance composition. A novel Mugue-like blended fragrance composition was prepared by mixing 5.0 g of the present invention products 1-4 with the Mugue-like blended fragrance composition of Table 18 (Comparative Product 17). The inventive products 53 to 56 mixed with the inventive products 1 to 4 and the comparative product 17 were subjected to sensory evaluation by 10 well-trained panelists.

  As a result, all 10 panelists evaluated that the products 53 to 56 of the present invention emphasized the natural green feeling of cucumber and enhanced the volume of floral as compared with the comparative product 17.

Example 18: Effect of addition to the Mugue-like blended fragrance formulation for each concentration of the product 3 of the present invention

A Mugue-like fragrance composition was prepared according to the Mugue-like blended fragrance formulation (mass%) shown in Table 19.

  That is, the comparative product 18 contains 1 ppm of 9-dodecenoic acid of the product 3 of the present invention, and similarly, Example 57 is 10 ppm of the product 3 of the present invention, Example 58 is 100 ppm of the product 3 of the present invention, and Example 59 is Inventive product 3 contains 0.1% by mass, Example 60 contains 1% by mass of inventive product 3, Example 61 contains 5% by mass of inventive product 3, and Comparative product 19 contains 10% by mass of inventive product 3. To do. Sensory evaluation was performed by 10 panelists who were well trained for each Mugue-like fragrance composition.

  The sensory evaluation was performed using an index for enhancing the natural feeling. 0: No change compared to the control product, 1: Natural feeling slightly compared to the control product, 2: Natural feeling compared to the control product, 3: Strong natural feeling compared to the control product, -1: The scent of Uri-sama was too strong compared to the control product, and was scored as not natural.

  In addition, as for the persistence of the scent, the comparison products 18 and 19 and the Mugue-like blended fragrance composition 57-61 of the present invention were attached to the tip of the scented paper, and the scent after leaving for 3 minutes was compared. 0: The smell was not felt, 1: The smell is considerably weaker than immediately after it is applied, 2: The smell is weaker than immediately after it is applied, 3: The smell is compared with immediately after it is applied Scoring as not weakening so much.

  Table 20 shows the sensory evaluation of the Mugue-like fragrance compositions of Comparative Products 18 and 19 and Invention Products 57 to 61.

  From the results shown in Table 20, the natural products 57 to 61 have an enhanced natural feeling, a floral natural feeling and sustainability are imparted, and a good Mugue-like aroma is remarkably emphasized. On the other hand, the comparative product 18 was not much different from the control product 3, and the comparative product 19 was evaluated as having a green, uri-like aroma too strong, and the balance of the Mugue-like aroma was lost. Moreover, this invention products 57-61 were evaluation that aroma was not weakened extremely. Although the comparative product 19 had the persistence of the fragrance, it was evaluated that the Mugue-like fragrance was lost.

Example 19: Effect of adding Mugue-like blended fragrance to liquid fragrance The Mugue-like blended fragrance composition obtained in Example 18 was added to a liquid fragrance prepared according to the formulation in Table 21. The liquid fragrances to which the comparative product 17 and the inventive products 53 to 56 were added were referred to as comparative product 20 and inventive products 62 to 65, respectively. These liquid fragrances were subjected to sensory evaluation by 10 panelists who were well trained.

  As a result, all 10 panelists evaluated that the products 62 to 65 of the present invention were given a natural green feeling compared to the comparative product 20 and emphasized the mugue-like aroma with a floral volume. It was.

Claims (5)

Improving milk fat feeling or oil and fat fragrance and / or milk fat feeling or oil and fat feeling flavor consisting of one or more selected from the group consisting of 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid and 10-dodecenoic acid Agent. The fragrance and / or flavor improving agent according to claim 1 is based on one or more selected from the group consisting of 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid and 10-dodecenoic acid. A perfume composition for improving the feeling of milk fat or oil containing 0.1 ppm to 10% . A fragrance composition comprising 0.1 ppm to 10% of one or more selected from the group consisting of 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid and 10- dodecenoic acid. A method for improving the feeling of milk fat or oil . 1 selected from the group consisting of 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid and 10-dodecenoic acid for the flavor improving agent according to claim 1 or the perfume composition according to claim 2 in food or drink. species or two or more Ru was added 1Ppb～0.1%, based, milk fat feeling or fat feeling flavor improvement methods food or drink. The fragrance improving agent according to claim 1 or the fragrance composition according to claim 2 is selected from the group consisting of 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid and 10-dodecenoic acid. A fragrance improving method for imparting a natural feeling of cosmetics, wherein 1 ppb to 0.1% is added based on seeds or two or more kinds .