JP2019065212A - Aroma and/or flavor improver containing decenoic acid - Google Patents

Abstract

To provide an aroma and flavor improver capable of improving aroma and flavor such as milk flavor and oil and fat feeling in a drink and food or perfumery, and a perfume composition containing the improver as an active component.SOLUTION: It is found that 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid or 10-dodecenoic acid themselves have unique flavor property such as green-like, cucumber-like, oil and fat feeling and soap-like, and aroma and flavor such as milk flavor and oil and fat feeling are improved and persistence of flavor is enhanced by adding them to a flavor composition or drink and food or perfumery.SELECTED DRAWING: None

Description

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

  In recent years, with diversification of consumer preference, 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 beverage that meets the consumer's taste. In response to these requirements, the flavor (food flavor) compound that has been proposed in the past can not sufficiently cope with the flavor, which is one of the raw materials for food and drink, and it has unique flavor and flavor characteristics not found in the past. The development of flavor compounds that are possessed and have excellent sustainability has become an urgent issue.

  In recent years, there have been many demands for the purpose of imparting and enhancing aroma and flavor such as milk fat sensation and oil and fat sensation to food and drink etc. in recent years, but with conventional flavor compounds alone, in response to the diversifying consumer demand in recent years. As it has become very difficult to respond, there is a strong demand for the development of flavor compounds that have unique flavor and odor characteristics that are unique to the prior art and that have a high flavor persistence.

  In addition, for cosmetic products as well, it is often required to impart and enhance oil-like flavor and oil like oil and fat, but under the present circumstances, it is a situation that responds to the diversified needs by combining complex odors.

For the purpose of imparting a flavor and aroma of milk fat, for example, Patent Document 1 discloses (E) -6-nonenal as milk, milk product, milk or food containing milk product, or dairy product substitute. It is described about the flavor compound which milk taste addition thru | or milk taste is improved by containing 50 ppt-200 ppb. However, the present compound is not satisfactory although it has an effect on milk-specific richness and milk-fat feeling. In addition, Patent Document 2 provides a milk flavor improving agent for milk, dairy product, milk or dairy food or beverage containing dairy extract, or vegetable extract containing Spilanthol, or a vegetable essential oil containing Spilanthol. Have been described. However, preparation of spilanthol takes time. Further, Patent Document 3 describes a method for enhancing the milk fatness of a milk-based flavor composition, which contains 12 ppt to 10 ⁴ ppm of 12-methyl tridecanal relative to the milk-based flavor composition. However, a satisfactory aroma improving effect was not obtained.

  For the purpose of imparting an aroma / flavor with a fat feeling, 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-based agent. However, this compound also has an aroma other than oil and fat feeling, and was not necessarily satisfactory as an oil and fat feeling enhancer. In addition, in Patent Document 5, a sesame-like roasted feeling, roasted feeling, oil and fat feeling enhancer comprising 2-methyl-3-thiophenethiol is disclosed in Patent Document 6; Sesame-like roasted feeling, roasted feeling, oil-based agent of butyl formate has been described. However, these compounds enhanced the sesame-like oily feeling.

  As a perfume use of dodecenoic acid, Patent Document 7 has a slightly bluish milk-like aroma by adding trans-6-dodecenoic acid to a milk flavor, and Patent Document 8 discloses 5-dodecene. It is described that it has a greenish buttery aroma by adding an acid to a butter flavor. However, Patent Document 7 shows that linear alkenoic acid and cis-6-alkenoic acid having a double bond at a position other than 6 do not have such an aroma.

  Further, Patent Document 9 describes 11-dodecenoic acid as a breath deodorizing agent using it as a fragrance.

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

  An object of the present invention is to provide an aroma and / or flavor improving agent capable of improving aroma and flavor such as milk flavor and oil feeling in food and drink etc. and a spice 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 itself is green-like and uri-like. It has unique flavor characteristics such as oil, oil and soap, and by adding it to a spice composition or food and drink, it improves aroma and flavor such as milk fat and oil, and enhances the persistence of aroma. The present invention has been completed.

Thus, the present invention provides the following.
(1) An aroma and / or flavor improver comprising one or more selected from the group consisting of 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid and 10-dodecenoic acid.
(2) A perfume composition containing the aroma and / or flavor improving agent of (1) as an active ingredient.
(3) Food / beverage products containing the flavor improving agent of (1) or the perfume composition of (2).
(4) A cosmetic comprising the fragrance improver of (1) or the fragrance composition of (2).
(5) A method for improving the aroma of a perfume composition, which comprises adding one or more selected from the group consisting of 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid and 10-dodecenoic acid to a perfume composition .
(6) A method for improving the flavor of food and drink, which comprises adding the flavor improver of (1) or the flavor composition of (2) to the food and drink.
(7) A method for improving the aroma of a cosmetic, which comprises adding the aroma improver of (1) or the fragrance composition of (2) to the 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 milk fatness and oiliness to the flavor and fragrance composition, and maintain the odor By adding a flavoring composition containing 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid or 10-dodecenoic acid to food and drink, etc. It is possible to improve the persistence of the aroma, and to provide a variety of food and drink that match the consumer's taste.

  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) form and (Z) form, or (E) form or (Z) form The present invention is also effective in a single body.

  The compounds 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 following reaction route.

  The step of the reaction is carried out by esterifying an unsaturated fatty acid having a double bond at the end as a raw material using an arbitrary alcohol and an acid catalyst such as p-toluenesulfonic acid and converting it into an aldehyde by ozone oxidation. The obtained aldehyde is subjected to Wittig reaction with phosphoylide obtained from the phosphonium salt, and the obtained dodecenoic acid ester is subjected to alkaline hydrolysis to obtain 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid or 10 Can produce dodecenoic acid.

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

  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) Can be mentioned.

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

  The aldehyde represented by the above reaction formula can be produced by blowing ozone into the obtained unsaturated fatty acid ester using methylene chloride as a solvent and under the conditions of -50 ° C to -30 ° C.

  The aldehyde obtained can be subjected to Wittig reaction using Wittig reagent in the presence of N, N-dimethylformamide and sodium alcoholate to produce dodecenoic acid ester. The sodium alcoholate used for the above Wittig reaction is not particularly limited, but it is preferable to use sodium methoxide or sodium ethoxide. In addition, Wittig reagents used in the Wittig reaction can include, for example, 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 solution of sodium hydroxide 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 added as it is to foods, beverages or cosmetics to improve the aroma and flavor such as milk fat and oil. And the persistence of the aroma can be enhanced, but it is mixed with other ingredients to prepare a flavor composition, and by blending the flavor composition into a food or drink or a And the like, and can also improve the persistence of the aroma. Furthermore, the 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid or 10-dodecenoic acid of the present invention can be used as a mixture in any ratio of two or more, and can also be mixed with other perfume ingredients. Can be used.

  The content of 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid or 10-dodecenoic acid, or a mixture of two or more thereof of the present invention in the perfume composition depends on the purpose or type of the perfume composition. Although it differs, 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 0.1 ppm to 10%, relative to the total mass of the perfume composition. A range of 2 ppm to 0.5% can be exemplified. Within these ranges, it has an excellent effect of improving the aroma and flavor such as milk fat and oil of the perfume composition. On the other hand, if the content with respect to the flavor composition exceeds 10%, it is not preferable because the characteristic odor and flavor such as curi-like and green-like peculiar to the compound appear strongly. Moreover, when content with respect to a fragrance | flavor composition is less than 0.1 ppm, the aroma and flavor improvement effect peculiar to this invention are not acquired.

  As other perfume ingredients which may be contained together with 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid or 10-dodecenoic acid of the perfume composition, various synthetic perfumes, natural perfumes, natural essential oils, plant extracts and the like It can be mentioned. For example, natural essential oils, natural flavors, and synthetic flavors described in "Patent Office, Well-known Conventional Techniques (fragrance) Part II Food flavors" or "Synthetic flavors, Chemistry and Commodity knowledge, Supplemental new edition, Chemical industry Nippon publication" Can be mentioned.

  For example, γ-caprolactone, γ-heptalactone, γ-octalactone, γ-nonalactone, γ-decalactone, 7-decene-4-olide, 3-methyl-4-decene-4-olide, 3-methyl-5- Decen-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-undecene-5-olide, 4-methyl-5-undecanolide, δ-dodecalactone 2-dodecene-5-olide, 4-methyl-5-dodecanolide, δ-tridecalactone, 2-tridecene-5-olide, 4-methyl-5-tridecanolide, δ-tetradecalactone, 2-tetradecene-5-yl Orido, 2-pentadecen-5-olide, 2-hexadecen-5-olide, 2-heptadecen-5-olide, 2-octadecene-5-olide, 2-nonadecen-5-olide, 2-eicosen-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-hydroxyl Decanoic acid, lauric acid, 5-hydroxydodecanoic acid, myristic acid, pentadecanoic acid, isopentadecanoic acid, palmitic acid, heptadecanoic acid, stearic acid, stearic acid, oleic acid, linoleic acid, fatty acids such as 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-hydroxyoctoate, 5-Hydroxy-9-methyl Esters such as ethyl kanate, methyl 5-acetoxydecanoate and ethyl 5-acetoxydecanoate; ethanol, propanol, butanol, pentanol, hexanol, heptanol, octanol, nonanol, decanol, benzyl alcohol, phenylethyl alcohol, furfuryl Alcohols such as alcohols; 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, acetyl isovaleryl, 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, ethyl anne Nitrogen-containing compounds such as tranilate, phenylethyl anthranilate, trimethylamine, indole, skatole, pyridine, isoquinoline, pyrazine, methylpyrazine and the like; 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, sulfole, acetyl lactate thiomethyl ester, propionyl lactate thiomethyl ester, butyryl lactate thiomethyl ester, valeryl Lactic acid thiomethyl ester, 2-methyl butyryl lactic acid thiomethyl ester, desilyl lactic acid thiomethyl ester, acetyl lactic acid thioethyl 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.

  The perfume 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 of them is, as needed, usually added to the perfume composition. For example, solvents such as water and ethanol used; ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, glycerin, hexylene glycol, benzyl benzoate, triethyl citrate, diethyl phthalate, hercoline, fatty acid triglyceride, fatty acid diglyceride and the like And a flavor retention agent.

  Further, one or more kinds of emulsifiers or stabilizers such as Quillaja extract, enzyme-treated lecithin, sucrose fatty acid ester, polyglycerin fatty acid ester, glycerin fatty acid ester, gum arabic and the like may be added to the fragrant composition, for example By emulsifying using a homomixer, a colloid mill, a high pressure homogenizer or the like, a form of an emulsified perfume preparation can also be obtained. The amount of the emulsifier or stabilizer used varies depending on the type of the emulsifier or stabilizer, but it is, for example, in the range of 0.1 to 25% by weight, preferably 5 to 20% by weight based on the weight of the emulsified perfume preparation. Can be mentioned.

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

  The 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid or 10-dodecenoic acid of the present invention is used alone or as described above to prepare a perfume composition containing two or more of them. By adding it to food or drink or a cosmetic product, it is possible to improve the aroma such as milk fat and oil feeling and the persistence of the aroma by utilizing the above-mentioned aroma characteristics.

  The aroma composition such as milk fat and oil is improved by the perfume composition containing 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid or 10-dodecenoic acid, or a mixture of two or more of them according to the present invention And, as a specific example of the food and drink which can improve the persistence of aroma, it is not limited at all, for example, carbonated beverages such as cola beverage, carbonated beverage with fruit juice, carbonated beverage with milk; fruit juice beverage , Soft drinks such as vegetable drinks, sports drinks, honey drinks, soy milk, vitamin supplement drinks, mineral supplement drinks, nutritional drinks, nourishing drinks, lactic acid drinks, milk drinks etc .; Green tea, black tea, oolong tea, herbal tea, milk tea, coffee Beverages and other favorite beverages; Chuhai, cocktail drinks, low-malt beer, alcoholic beverages such as confectionery liquor, fragrant liquors; Butter, cheese Milk products such as yogurt, yogurt, ice cream, lacto ice, frozen desserts, yogurt, pudding, jelly, desserts such as daily dessert and mixes for producing them; caramel, candy, tablets, crackers, biscuits, donuts Cookies, cakes, pies, chocolates, snacks, butter cream, custard cream, confectionery such as puff cream and mixes such as cake mix for producing them; Sesame oil, soybean oil, rapeseed oil, fats and oils such as lard; Meat such as pork, beef, lamb, horse meat, etc .; Curry, stew, beef stew, hayashi rice sauce, meat sauce, marbo tofu, hamburg, eggplant, omelette rice, soups, meat balls, horned 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 or 10-dodecenoic acid, or a mixture of two or more of them according to the present invention improves the aroma and enhances the persistence of aroma. Specific examples of cosmetic products that can be used include, but are not limited to, for example, perfumes; hair care products such as shampoos, rinses, hair setting agents (hair creams, pomades etc); foundations, lipsticks, lip balms, lip glosses, Cosmetics such as lotions, cosmetic lotions, cosmetic creams, cosmetic gels, cosmetic liquids, pack agents, etc. Suntan cosmetics such as suntan products, sunscreen products; face soaps, body soaps, laundry soaps, laundry Detergents, Disinfectant Detergents, Detergents and Other Detergents for Health and Hygiene; Toothpaste, Tissue Paper, Toilet Paper, etc. Health and sanitation materials such; room fragrance, can be exemplified aromatic products such Kakoron.

  In addition, the form of the cosmetic is not particularly limited. For example, the present invention is applicable to various forms such as liquid, emulsion, cream, paste, solid, multilayer and the like. Besides these, it can be applied as a sheet agent, a spray agent, and a mousse agent.

  The blending amount of 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid or 10-dodecenoic acid, or a mixture of two or more of them of the present invention varies depending on the purpose or the type of food or drink or cosmetic. 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, particularly preferably 20 ppb to 50 ppm based on the total weight of the food or drink or the cosmetic It can be illustrated. Within these ranges, the food and drink or cosmetic has an excellent effect of improving the aroma and flavor such as milk fat and oil. On the other hand, when the compounding amount with respect to food or drink or a cosmetic exceeds 0.1%, it is unpreferable because the characteristic odor and flavor such as curi-like and green-like peculiar to the compound appear strongly. In addition, when the blending amount with respect to food or drink or a cosmetic is less than 1 ppb, the aroma / flavor improvement effect peculiar to the present invention can not be obtained.

  Hereinafter, the present invention will be more specifically described by way of examples. The present invention is not limited to these.

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

  In a 100 mL three-necked flask, methyl 7-octenoate and methylene chloride (20 mL) were charged, and ozone was blown at -50 to -30.degree. 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 for 30 minutes at room temperature, it was concentrated and diluted with ether. The organic layer was washed with water, dried over magnesium sulfate, filtered and concentrated to give methyl 7-oxoheptanoate.

  In a 100 mL three-necked flask, methyl 7-oxoheptanoate, N, N-dimethylformamide (50 mL) and pentyltriphenylphosphonium bromide (5.8 g, 14.1 mmol) were charged, sodium methoxide (28% methanol solution, 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.

  Methyl 7-dodecenoate and methanol (10 mL) were charged into a 30 mL eggplant flask, 25% aqueous sodium hydroxide solution (2.0 g) was added, and the mixture was stirred at 40 ° C. for 1 hour. 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 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 (the product of the present invention 1: 132 mg, cis / trans isomer ratio 90:10).

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

  In a 100 mL three-necked flask, methyl 8-nonenoate and methylene chloride (20 mL) were charged, and ozone was blown at -50 to -30.degree. 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 for 30 minutes at room temperature, it was concentrated and diluted with ether. The organic layer was washed with water, dried over magnesium sulfate, filtered and concentrated to give methyl 8-oxooctanoate.

  In a 100 mL three-necked flask, N, N-dimethylformamide (30 mL) and butyltriphenylphosphonium bromide (5.1 g, 12.8 mmol) are charged, methyl 8-oxooctanoate is added, and then sodium methoxide (28% methanol) The 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.

  Methyl 8-dodecenoate and methanol (10 mL) were charged into a 30 mL recovery flask, 25% aqueous sodium hydroxide solution (2.0 g) was added, and the mixture was stirred at 40 ° C. for 3 hours. 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 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 (Inventive product 2:47 mg, cis / trans isomer ratio 92: 8).

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

  In a 200 mL three-necked flask, methyl 9-decenoate and methylene chloride (30 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 2 mL). The mixture was stirred at room temperature for 30 minutes and concentrated to give methyl 9-oxononanoate.

  Methyl 9-oxononanoate, N, N-dimethylformamide (50 mL), propyltriphenylphosphonium bromide (9.05 g, 23.5 mmol) are charged into a 100 mL three-necked flask, 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.

  Methyl 9-dodecenoate and methanol (30 mL) were charged into a 50 mL recovery flask, 25% aqueous sodium hydroxide solution (4.0 g) was added, and the mixture was stirred at 40 ° C. for 3 hours. 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 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 (Inventive product 3: 218 mg, cis / trans isomer ratio 84:16).

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

  Ethyl 10-undecenoate and methylene chloride (40 mL) were charged into a 100 mL three-necked flask, 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 give ethyl 10-oxodecanoate.

  Ethyl 10-oxodecanoate, N, N-dimethylformamide (30 mL) and ethyltriphenylphosphonium bromide (8.1 g, 21.7 mmol) are charged into a 100 mL three-neck flask, 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 saturated aqueous sodium carbonate solution, saturated aqueous ammonium chloride solution, water, dried over magnesium sulfate, filtered and concentrated to give ethyl 10-dodecenoate.

  Ethyl 10-dodecenoate and methanol (10 mL) were charged into a 50 mL recovery flask, 25% aqueous sodium hydroxide solution (4.0 g) was added, and the mixture was stirred overnight at room temperature. The reaction solution was washed with toluene, and the aqueous layer was acidified with concentrated sulfuric acid and then 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 (Inventive product 4: 498 mg, cis / trans isomer ratio 89:11).

Example 5: Evaluation of aroma 7-dodecenoic acid (Invention 1), 8-dodecenoic acid (Invention 2), 9-dodecenoic acid (Invention 3), 10-dodecenoic acid (Invention) The aroma evaluation was performed by five well-trained panelists for each 0.1% triacetin solution of product 4). The evaluation of aroma was carried out by using the 0.1% triacetin solution, the aroma of the bottle and the odor paper impregnated with the solution. The average aroma rating of 5 persons is shown in Table 1.

Example 6: Effect of Addition to Milk-Like Formulated Flavor Composition Each component (% by mass) of Table 2 was formulated as a milk-like formulated flavor composition. A novel milk-like blended perfume composition was prepared by mixing 2.0 g of the inventive products 1 to 4 with the milk-like blended perfume composition (comparative product 1) in Table 2. The sensory evaluation was performed by ten panelists who were well trained in the invention products 5 to 8 and the comparison product 1 in which the invention products 1 to 4 were mixed.

  As a result, all 10 panelists evaluated that the inventive products 5 to 8 had improved milk fat feeling, had a rich feeling unique to milk fat, and had a high persistence of aroma as compared with the comparative product 1. .

Example 7 Effect of Addition to Butter-Like Formulated Flavor Composition Each component (% by mass) of Table 3 was formulated as a butter-like formulated flavor composition. A novel butter-like blended perfume composition was prepared by mixing 5.0 g of the inventive products 1 to 4 with the butter-like blended perfume composition (comparative product 2) in Table 3. The sensory evaluation was performed by ten well trained panelists of the invention products 9 to 12 and the comparison product 2 in which the products of the invention 1 to 4 were mixed.

  As a result, all 10 panelists emphasized that the inventive products 9 to 12 have a good oily feeling, a unique oilyness, and a high persistence of aroma as compared to the comparative product 2. evaluated.

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

  That is, Comparative product 3 contains 10 ppb of 7-dodecenoic acid of product 1 of the present invention, and similarly, Example 13 has 0.1 ppm of product 1 of the present invention, Example 14 has 1 ppm of product 1 of the present invention, and Example 15 10 ppm of the product 1 of the present invention, 0.1 mass% of the product of the present invention in the example 16 Example 1, 1 mass% of the product of the present invention 1 17 Example 10, 10 mass% of the product 1 of the present invention The product 4 contains 20% by mass of the product 1 of the present invention. Each milk-like flavor composition was subjected to sensory evaluation by 10 well trained panelists.

  The sensory evaluation was performed using an index of milk fat sensation enhancement and flavor persistence. With regard to milk fat sensation enhancement, 0: No change with control product 1 compared with control product 1: 1: slightly milk fat feeling compared with control product 2: milk fat feeling compared with control product 3: strong compared to control product There was a feeling of milk fat, and it was scored as -1: the balance of milk-like aroma is too strong compared with the control product, and the balance of the feeling of milk fat is bad.

  In addition, with regard to the persistence of the scent, the tips of the scented paper were applied with the milk-like flavor composition of Comparative products 3 and 4 and the inventive products 13 to 18 and the odors immediately after application and after leaving for 3 minutes were compared. 0: no smell was felt 1: the smell was considerably weaker than immediately after application 2: the odor was weaker than immediately after application 3: 3: the odor was compared to immediately after application It scored as not weakening so much.

  The sensory evaluations of the milk-like flavor compositions of Comparative products 3 and 4 and products of the present invention 13 to 18 are shown in Table 5.

  From the results of Table 5, according to the products 13 to 18 of the present invention, the milk fat feeling is enhanced, a rich and rich creamy body feeling is imparted, and the good milk-like aroma is significantly emphasized. On the other hand, Comparative Product 3 was almost the same as Control Product 1, and Comparative Product 4 was evaluated to be too strong for Green and Uri, so that the original flavor of milk was lost.

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

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

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

  In addition, the sensory evaluation method was implemented by the method similar to Example 8. The sensory evaluation of the milk-like flavor composition of Comparative products 5 and 6 and inventive products 19 to 24 is shown in Table 7.

  From the results of Table 7, according to the products 19 to 24 of the present invention, the milk fat sensation is enhanced, a rich and rich creamy body sensation is imparted, and the good milk-like aroma is significantly emphasized. On the other hand, Comparative product 5 was almost the same as Control product 1, and Comparative product 6 was evaluated to be too strong for green and uri, so that the original flavor of milk was lost.

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

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

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

  In addition, the sensory evaluation method was implemented by the method similar to Example 8. The sensory evaluation of the milk-like flavor composition of Comparative products 7 and 8 and products of the present invention 25 to 30 is shown in Table 9.

  From the results of Table 9, according to the present inventions 25 to 30, milk fat feeling is enhanced, rich and rich creamy body feeling is imparted, and good milk-like aroma is significantly emphasized, while the comparison product No. 7 was almost the same as Control 1 and Comparative 8 was evaluated to be too strong for Green and Uri-like, so that the original flavor of milk was lost.

  Further, from the results of Table 9, according to the present inventions 25 to 30, the aroma was evaluated as not extremely weakened. Although the comparative product 8 had the persistence of the aroma, the aroma itself was evaluated as having lost the original aroma of milk.

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

  That is, Comparative product 9 contains 10 ppb of 10-dodecenoic acid of the product 4 of the present invention, and similarly, Example 31 has 0.1 ppm of the product 4 of the present invention, Example 32 has 1 ppm of the product 4 of the present invention, and Example 33 10 ppm of the product 4 of the invention, 0.1 mass% of the product 4 of the invention 34, 1 mass% of the product 4 of the invention 35, 10 mass% of the product 4 of the invention 36, and comparison The article 10 contains 20% by mass of the invention 4 respectively. Each milk-like flavor composition was subjected to sensory evaluation by 10 well trained panelists.

  In addition, the sensory evaluation method was implemented by the method similar to Example 8. The sensory evaluations of the milk-like flavor compositions of Comparative products 9 and 10, and inventive products 31 to 36 are shown in Table 11.

  From the results of Table 11, according to the products 31 to 36 of the present invention, the milk fat feeling is enhanced, a rich and rich creamy body feeling is imparted, and the good milk-like aroma is significantly emphasized. On the other hand, Comparative product 9 was almost the same as Control product 1, and Comparative product 10 was evaluated to be too strong for green and uri, so that the original flavor of milk was lost.

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

Example 12: Effect of addition to the butter-like compounded perfume formulation according to the concentration of the product 3 of the present invention A butter-like perfume composition (Control product 2) was prepared according to the butter-like compounded perfume composition (% by mass) shown in Table 12.

  That is, the comparative product 11 contains 10 ppb of 9-dodecenoic acid of the product 3 of the present invention, and similarly, Example 37 has 0.1 ppm of the product 3 of the present invention, Example 38 has 1 ppm of the product 3 of the present invention, and Example 39 10 ppm of the product 3 of the present invention, 0.1% by mass of the product 40 of the present invention of Example 40, 1% by mass of the product of the present invention 41, and 40% by mass of the product of the present invention 42 The article 12 contains 20% by mass of the invention 3 respectively. Each buttery flavor composition was subjected to sensory evaluation by 10 well trained panelists.

  The sensory evaluation was performed using the index of enhancement of oily feeling and persistence of smell. With regard to the enhancement of oil and fat sensation, 0: No change with the control product, 1: slightly oily feeling compared with the control product compared with the control product 2: 2: fat and oil feeling compared with the control product, 3: stronger than the control product There was a greasy feeling, and -1: the odor was too strong compared to the control product and was scored as having a bad balance of greasy feeling.

  In addition, with regard to the persistence of the scent, the butter-like flavor composition of Comparative products 11 and 12 and the inventive products 37 to 42 was applied to the tip of the scented paper, and the odor immediately after application and after leaving for 3 minutes was compared. 0: no smell was felt 1: the smell was considerably weaker than immediately after application 2: the odor was weaker than immediately after application 3: 3: the odor was compared to immediately after application It scored as not weakening so much.

  The sensory evaluation of the butter-like flavor composition of Comparative products 11 and 12 and Products 37 to 42 of the present invention is shown in Table 13.

  From the results of Table 13, according to the invention products 37 to 42, the oily feeling is enhanced, the rich and rich body feeling is imparted, and the good buttery aroma is remarkably emphasized. On the other hand, Comparative product 11 was almost the same as Control product 2, and Comparative product 12 was evaluated as being too strong in green and uri-like, so that the original aroma of butter was lost.

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

Example 13 Effect of Adding Milk-Like Formulated Fragrance Composition to Milk Tea The milk-like blended spice composition (comparative product 1 of the present invention 5 to 8) obtained in Example 6 was prepared according to the formulation of Table 14 The resulting mixture was added to milk tea and the milk tea beverage was prepared by a conventional method. The milk tea to which the comparative product 1 and the inventive products 5 to 8 were added was designated as the comparative product 13 and the inventive products 43 to 46, respectively. These milk teas were subjected to sensory evaluation by 20 well trained panelists.

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

Example 14 Effect of Adding Butter-Like Formulated Fragrance Composition to Cookie The butter-like blended spice composition (comparative product 2, present invention products 9 to 12) obtained in Example 7 was prepared according to the formulation of Table 15. It was added to the cookie dough and baked at 220 ° C. for 7 minutes to prepare cookies. Cookies to which the comparative product 2 and the inventive products 9 to 12 were added were respectively designated as the comparative product 14 and the inventive products 47 to 50. The sensory evaluation was performed by 20 well trained panelists on these cookies.

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

Example 15 Effect of Addition to Pork Bone Ramen Soup In accordance with the recipe of Table 16, a powder composition for pork bone ramen was prepared.

  10 g of the above-mentioned pork bone ramen powder composition was diluted by adding hot water (70 ° C.), and this was made into a total of 1000 ml. In addition, after adding and diluting with hot water, 0.1 g of a 0.1% solution of 9-dodecenoic acid (Inventive product 3) diluted with alcohol and water was added, and further diluted with hot water to make a total of 1000 ml. The pork bone ramen soup is the product 51 of the present invention. The sensory evaluation was performed by 20 well trained panelists on the comparative product 15 and the inventive product 51.

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

Example 16 Effect of Addition to Non-Alcoholic Beer Non-alcoholic beer was prepared according to the recipe in Table 17.

  A panel of 20 persons trained well on the product of the present invention 52 to which the comparative product 16 and the 0.1% solution of 9-dodecenoic acid were added without adding the 9-dodecenoic acid 0.1% solution used in Example 15 I made an evaluation.

  As a result, all of the 20 panelists evaluated that the product of the present invention 52 had a feeling of body on the aftertaste as compared with the comparative product 16, and that the beer-specific texture and thickness were enhanced.

Example 17 Effect of Addition to Muge-Like Formulated Perfume Composition Each component (% by mass) of Table 18 was formulated as a Muge-like blended fragrance composition. A novel muge like compounded perfume composition was prepared by mixing 5.0 g of the inventive products 1 to 4 with the muge like compounded perfume composition (comparative product 17) in Table 18. The sensory evaluation was performed by ten panelists who were well trained in the invention products 53 to 56 and the comparison product 17 in which the invention products 1 to 4 were mixed.

  As a result, all 10 panelists evaluated that the inventive products 53 to 56 emphasized the natural green feeling of Uri-like as compared with the comparative product 17, and the volume feeling of the floral was enhanced.

Example 18: The effect of the concentration of the product 3 of the present invention on the formulation of the mugue-like compounded perfume formulation

A mugue-like perfume composition was prepared according to the mugue-like compounded perfume formulation (% by mass) shown in Table 19.

  That is, Comparative product 18 contains 1 ppm of 9-dodecenoic acid of product 3 of the present invention, and similarly, Example 57 contains 10 ppm of product 3 of the present invention, Example 58 contains 100 ppm of product 3 of the present invention, and Example 59 contains this 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 Do. The sensory evaluation was conducted by 10 well trained panelists for each of the mugue-like perfume compositions.

  The sensory evaluation was performed using the index of natural feeling enhancement. 0: No change compared to the control product 1: 1: slightly natural feeling compared to the control product 2: natural feeling compared to the control product 3: strong natural feeling compared to the control product -1: Compared with the control product, it was scored as not being natural due to the strong odor of Uri-like.

  In addition, with regard to the persistence of the scent, the mugue-like compounded flavor composition of Comparative products 18 and 19 and the present inventions 57 to 61 was applied to the tip of the scented paper, and the odors immediately after application and after leaving for 3 minutes were compared. 0: no smell was felt 1: the smell was considerably weaker than immediately after application 2: the odor was weaker than immediately after application 3: 3: the odor was compared to immediately after application It scored as not weakening so much.

  The sensory evaluations of the comparative examples 18 and 19 and the inventive muge-like flavor composition of the present inventions 57 to 61 are shown in Table 20.

  From the results of Table 20, the products of the present invention 57 to 61 have an enhanced natural feeling, are imparted with a natural feeling and persistence of floral, and a good muge like aroma is significantly emphasized. On the other hand, Comparative product 18 was almost the same as Control product 3, and Comparative product 19 was evaluated as being too strong in green and uri-like aroma and losing the balance of mugue-like aroma. Moreover, this-invention goods 57-61 were evaluation that aroma did not weaken extremely. Although the comparative product 19 had the persistence of the aroma, it was an evaluation that the mugue-like aroma was lost.

Example 19 Effect of Adding Muge-Like Formulated Perfume to Liquid Fragrance The Muge-like compounded perfume composition obtained in Example 18 was added to the 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 respectively designated as the comparative product 20 and the inventive product 62 to 65. The sensory evaluation was performed by 10 well trained panelists on these liquid fragrances.

  As a result, in all 10 panelists, the present invention products 62 to 65 have a natural green feeling as compared with the comparative product 20, and the evaluation is that the mugue-like aroma with floral voluminousness is emphasized. The

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 Flavor and flavor improver.
(2) The flavor and / or flavor improving agent according to (1) is selected from 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 which contains 0.1 ppm to 10% .
(3 ) A perfume 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 in a perfume composition A method for improving the milk fat or oily flavor of the composition.
( 4 ) A flavor improver according to (1) or a flavor composition according to (2) in food and drink selected from the group consisting of 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid and 10-dodecenoic acid 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 kind selected from the group consisting of 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid and 10-dodecenoic acid in perfumery of (1) or perfume composition of (2) in a cosmetic or two or more of Ru was added 1Ppb～0.1% based aroma improvement method for imparting a natural feeling of cosmetic.

Claims (7)

  An aroma and / or flavor improver comprising 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 comprising the aroma and / or flavor improving agent according to claim 1 as an active ingredient.   Food-drinks containing the flavor improving agent of Claim 1, or the fragrance | flavor composition of Claim 2.   A cosmetic comprising the fragrance improving agent according to claim 1 or the perfume composition according to claim 2.   A method for improving the aroma of a perfume composition, which comprises adding one or more selected from the group consisting of 7-dodecenoic acid, 8-dodecenoic acid, 9-dodecenoic acid and 10-dodecenoic acid to the perfume composition.   The flavor improvement method of food-drinks which adds the flavor improvement agent of Claim 1, or the fragrance | flavor composition of Claim 2 to food-drinks.   The fragrance improvement method of a cosmetics which adds the fragrance improving agent of Claim 1, or the fragrance | flavor composition of Claim 2 to cosmetics.