• 专利附录
  • 专利说明
  • 权利要求
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    • 专利摘要:
    1463567 Methylpentenoic and methylpentynoic acids INTERNATIONAL FLAVORS & FRAGRANCES Inc 22 Oct 1974 [23 Oct 1973 22 July 1974] 45613/74 Heading C2C [Also in Divisions A2 and A5] 4-Chloro-2-pentene is prepared by reacting piperylene with hydrogen chloride at 10-15‹ C. 2 - methyl - 3 - pentenoic acid isomer mixture is made by reacting the Grignard compound of 4-chloro-2-pentene in tetrahydrofuran with dry ice. The product is isolated in toluene solution with addition of HCl. 3-Pentyn-2-ol is prepared by reacting methyl magnesium chloride in tetrahydrofuran with Mapp gas (methyl acetylene/allene mixture) followed by addition of acetaldehyde. 4-Chloro-2-pentyne is prepared by reacting 3-pentyn-2-ol with PCl 3 . 2-Methyl-3-pentynoic acid. The Grignard reagent of 4-chloro-2-pentyne is prepared in tetrahydrofuran and poured on to dry ice. The product, obtained by acidification with HCl extraction with toluene is a 3 : 1 mixture of 2-methyl-3-pentynoic acid and 2-methyl-2,3- pentadienoic acid. Cis-2-methyl-3-pentenoic acid and 2-methyl-2- pentenoic acid are obtained by hydrogenating the above mixture of acids in methanol using a Pd/CaSO 4 catalyst.
    公开号:SU1098539A1
    申请号:SU752076551D
    申请日:1975-08-22
    公开日:1984-06-23
    发明作者:Б.Холл Джон；Франсиско Виналс Хоакин；Джозеф Шастер Эдвард；Гуго Фок Манфред
    申请人:Интернэшнл Флейворз Энд Фрейгрансиз Инк (Фирма)；
    IPC主号:
    专利说明:

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    The invention is intended for use in the food, tobacco and perfume industry and is intended for methods of changing the taste and smell of food products, flavoring substances and perfumes. The known method provides for the introduction into the products and products derived 2-methylpentene acid. This compound gave them the smell and taste of earthlings 1. The aim of the invention is to expand the range of tastes and odors of products and products. To achieve this goal, higher cis-2-methyl-3-pentenic acid is used, and it is taken in an amount of 0.000001-5% by mass. This acid can be used in a mixture with the trans-isomer in a 3: 2 or 2-methyl-2-pentenoic acid ratio in a 4: 1 ratio. The stereoisomers of 2-methyl-3-pentenoic acid have the structures CHj Higher cis-2-methyl-Z-pentenoic acid communicates and / or strengthens in food, tobacco, perfumery sweetish, reminiscent of fruit, cereal, wine, horse to or rum smell, as well as the taste of earthlings, coconut, oil of rum or candy, from burnt sugar. When you add it to natural tobacco or its substitutes, you can get a smell that resembles the smell of Turkish tobacco and has a nuance of wood and smoke. The term “change in taste and smell” means giving products (products m), which themselves are slightly odorous and relatively tasteless, also enhancing the existing characteristics, its natural smell is insufficient, or telling the existing smell a shade to modify the quality, character or taste of the product. Food products that can be processed by the proposed method - soups, drinks, including non-alcoholic, dairy sweets, vegetables, cereals, snacks, etc. Higher cis-2-methyl-3-pentvonic acid can be used in combination with other flavors, binders, stabilizers, thickeners, surfactants, etc. Aromas can be selected from the group that includes natural or synthetic essential oil, ethanol, geraniol, ethylmethylphenylglycid, vanillin, ethylproelargonate, isoamylacetate, ethyl butyrate, ethylvalerate, maltol, naphthylethylester, ethyl acetate, isoamyl, ethyl acetate, maltol, ethyl acetate, ethyl acetate, ethyl acetate, ethyl acetate, ethyl butyrate, ethyl valerate, maltol, isoamyl, ethyl acetate, ethyl acetate, ethyl acetate, ethyl butyrate, ethyl valerate, maltol, ethyl acetate, ethyl acetate, ethyl acetate, ethyl butyrate, ethyl acetate, maltol, ethyl naphthalene, ethyl acetate, ethyl butyrate. , 4-prephenyl-1, 2, 6-trimethoxybenzene or their mixture. Binders (ethanol, alcohol, glycol) can be used as a carrier for the acid. Such compositions are made by simply mixing the ingredients in the required proportions. To obtain a solid composition, the acid is mixed, for example, with gum arabic, tragacanth, Irish moss and spray dried. You can also mix pre-dried ingredients: vanilla, starch, sugar, etc. When higher cis-2-methyl-3-pentenoic acid is added to perfume products, the combined odors of the components create a pleasant aroma, most often the flavor of earthlings. Perfumes include odorants and deodorizers of air, soaps, surfactants, perfumes and colognes, toilet water, bath perfumes, hair preparations - varnishes, diamonds, lipsticks and shampoos, cosmetic creams, lotions, powders, powders, talcs, etc. The amount of acid added may vary within the above ranges depending on the desired organoleptic effect and the nature of the product (product). Example. Prepare a composition containing the following ingredients, in% by weight: Geraniol 1.00 Oylmethylphenylglycidate3, 33 Higher cis-2-methyl-3-pentenoic acid4, 77 Vanillin5,66 Ethylspered 13,06 Isoamylacetate 14,00 Ethylbutyrate 58,08 Then the composition solution 4 volumes of propylene glycol are added and the solution is added to a thick sugar melt in an amount of about 4.3 g per 4.5 kg of melt. The sugar is then used to make candy. Candy has an excellent earthy flavor. Example 2. A composition of the following composition is prepared, wt%: Naphthyl ethyl ether 0.96 Vanillin 2.66 Ethylmethylphenylglycidate 2, 88 Higher cis-2-methyl-3-pentene acid 4.90
    Ethylacetate9.68
    Isoamylacetate 12,25 Ethylbutyrate26,20
    Isoamyl butyrate 40.57 The composition is then mixed with gum arabic in the proportion of 3.171 kg per 12.684 kg of gum in 29.395 kg of water and spray dried. The mixture of the composition with the carrier thus obtained is added to the dessert gelatin mixture in the amount of 2.85 g per 45.3 kg of gelatin mixture. The gelatinous dessert obtained from the latter has an excellent earthy aroma.
    Example 3. Get tobacco mixture by mixing the following substances May.%:
    Light tobacco40,1
    Tobacco Burley24,9
    Maryland Tobacco 1.1 Turkish Tobacco 11.6 Tobacco Stalks
    fermented 14.2 Glycerin2.8
    Water5,3
    Receive also flavoring composition, wt.%:
    Ethyl butyrate 0.05
    Ethylvalerate 0.05
    Maltol2,00
    Cocoa extract 26.00 Coffee extract 10.00 Ethyl alcohol 20.00 Water41.90
    The flavor composition is added to the tobacco mixture in an amount of 0.5%, then half of the tobacco is further treated (5 and 10 hours, per million) of the highest cis-2-methyl-3-pentenoic acid. Cigarettes obtained from processed tobacco are more fragrant, sweetish, stronger, but less sharp in taste and smoother than control cigarettes, prygtovlennye from tobacco mixture that does not contain acid. They have the flavor of Turkish tobacco.
    Example 4. Higher cis-2-methyl-3-pentenoic acid is introduced into cologne in the order of 2.5%. Cologne acquires richly pronounced sweetish aroma of fresh earth.
    Example 5,100 g of soap shavings are mixed with 1 g of a mixture of 2-methyl-3-pentenoic acid isomers with a cisgtrans ratio of 3: 2 until a substantially homogeneous composition is obtained. The soap composition has an earthy aroma with a sweetish fresh shade.
    Example 6. A flavoring composition was prepared, wt%: Paraoxybenzylacetone 0.2 Vanillin 1.5
    Maltol2.0
    Ethyl 3-methyl-3-phenylglycidate1, 5
    Benzyl acetate2.0
    Ethylbutyrate1.0
    Methylcinnamat 0.5
    Methyl anthranilate 0.5 alpha ionone 0,1
    Gamma undecalactone 0,2 Diacetyl 0,2
    Anetol0,1
    CIS-3-Hexenol1,7
    95% ethanol aqueous solution38,5
    Propylene glycol
    0.2 wt.% Of a mixture of 80% cis-2-methyl-3-pentanoic acid and 20% 2-methyl-2-pentanoic acid was added to a portion of this composition. But then aromatize the dairy non-alcoholic sweetened beverage with a composition with and without the addition of these acids. In the first case, a drink is obtained with a sweet, fresh, earthy taste and flavor.
    权利要求:
    Claims (3)
    [1]
    1. METHOD FOR CHANGING THE TASTE AND ODOR OF FOOD PRODUCTS, TASTE, AND PERFUMERY PRODUCTS by introducing a 2-methylpentenoic acid derivative, characterized in that, in order to expand the range of tastes and smells of products and products, higher cis-2-methyl-3- is used pentenoic acid, and take it in an amount of 0.000001-5 wt.%.
    [2]
    2. The method according to claim 1, characterized in that the higher cis-2-methyl-3-pentenoic acid is used in a mixture with the trans isomer in a ratio of 3: 2.
    [3]
    3. The method according to π. 1, characterized in that the higher cis-2-methyl-q-methyl-3-pentenoic acid is used SS in a mixture with 2-methyl-2-pentenoic acid in a ratio of 4: 1.
    类似技术:
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    US3899597A|1975-08-12|Altering raspberry flavored foodstuffs with 4-|-2-butanol and/or 4-|-2-butanol, and/or acetates thereof
    SU1098539A1|1984-06-23|Method of changing taste and scent of food products,flavouring agents and perfumery articles
    US3960860A|1976-06-01|2-Methyl-5,7-dihydrothieno-[3,4d]-pyrimidine
    US4224351A|1980-09-23|Flavoring with certain sulphur compounds
    US4217251A|1980-08-12|Novel cyclopentanone derivatives used as perfume ingredients
    EP0073984B1|1988-04-27|Perfuming and/or flavouring compositions containing unsaturated acids
    US3914451A|1975-10-21|Imparting a nutty flavor with 2-butyl-2-butenal
    US3862340A|1975-01-21|Flavoring with 5-phenyl pentenals
    US4173584A|1979-11-06|Novel cyclopentanone derivatives as flavor- and odor-modifying ingredients
    US4071034A|1978-01-31|2-Alkyl-4-phenyl-dihydropyrans and processes for augmenting the organoleptic properties of tobacco using one or more of said pyrans
    US3917870A|1975-11-04|Enhancing grape flavor with 2-phenyl-3-carboethoxyfuran and bis | disulfide
    JP4771246B2|2011-09-14|Aroma / flavor / flavoring composition and food / beverage, perfume, cosmetics or tobacco to which it is added
    US4118343A|1978-10-03|Tricyclo[6.2.1.02,7 ]undec-9-en-3-one perfume composition
    US4031140A|1977-06-21|4- AND 5-Phenyl pentenal acetals
    DE2840823C2|1982-05-06|Trans, trans-? -Damascon, mixtures of which contain more than 50% trans, trans-? -Damascon and cis, trans-? -Damascon and their use as condiments
    US4115406A|1978-09-19|2-Alkyl-4-phenyl-dihydropyrans and processes for augmenting the organoleptic properties of foodstuffs and tobacco using one or more of said pyrans
    US4547315A|1985-10-15|Alkyl alpha-campholenates and dihydro derivatives thereof as odorants and flavorants
    US3687692A|1972-08-29|Flavoring compositions and processes
    US3978009A|1976-08-31|Substituted |s as odor-modifying agents
    US4261867A|1981-04-14|Using 1-ethynyl-2,2,6-trimethyl-cyclohexanol to enhance woody fragrance of perfume compositions
    US4036886A|1977-07-19|Processes for producing 4- and 5-phenyl pentenals
    US4034044A|1977-07-05|Menthone-8-thiol, carvomenthone-8-thiol and process for preparing same
    同族专利:
    公开号 | 公开日
    JPS5637784B2|1981-09-02|
    FR2248022B1|1981-08-07|
    NL182446B|1987-10-16|
    SU731951A1|1980-05-05|
    DE2446826A1|1975-04-30|
    NL182446C|1988-03-16|
    FR2248022A1|1975-05-16|
    DE2446826C2|1983-06-16|
    CH613847A5|1979-10-31|
    IT1050254B|1981-03-10|
    JPS5070534A|1975-06-12|
    US3931306A|1976-01-06|
    NL7412440A|1975-04-25|
    CA1018540A|1977-10-04|
    GB1463567A|1977-02-02|
    AU7444774A|1976-04-29|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    RU2531353C2|2008-12-09|2014-10-20|Университат Де Лез Иль Балеар|Alpha-derivatives of cis-monounsaturated fatty acids applicable as therapeutic agent|
    DE2530227C3|1974-07-22|1980-05-29|Int Flavors & Fragrances Inc|2-methyl-substituted pentenoic acid esters, 2-methyl-cis-3-pentenoic acid, and their acid and ester mixtures, their production process and use|
    US4400390A|1981-11-05|1983-08-23|International Flavors & Fragrances Inc.|Methyl-thio-2-methyl-2-pentenoates|
    WO2007104727A1|2006-03-16|2007-09-20|Basf Aktiengesellschaft|Substituted alkenes as initiators for cationic polymerization|
    WO2009117623A2|2008-03-19|2009-09-24|Tyratech, Inc.|Pest control using natural pest control agent blends|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    US40885473A| true| 1973-10-23|1973-10-23|
    US05/490,717|US3931306A|1973-10-23|1974-07-22|Process for producing isomer mixtures containing high proportions of cis-2-methyl-3-pentenoic acid|
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