Classifications

• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
  • C11B9/00—Essential oils; Perfumes
  • C11B9/0069—Heterocyclic compounds
  • C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
  • C11B9/008—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing six atoms
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
  • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
  • A23L27/20—Synthetic spices, flavouring agents or condiments
  • A23L27/205—Heterocyclic compounds
  • A23L27/2052—Heterocyclic compounds having oxygen or sulfur as the only hetero atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
  • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
  • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D309/10—Oxygen atoms

Definitions

• the present invention relates to the use of isomerically pure or highly isomerically enriched cis- or trans- (2-isobutyl-4-methyltetrahydropyran-4-yl) acetate for use as aroma chemicals.
• the invention further relates to a process for the preparation of isomerically pure or highly isomerically enriched cis- or trans- (2-isobutyl-4-methyl-tetrahydropyran-4-yl) acetate and the products obtainable by this process.
• the invention further relates to a fragrance or flavoring composition containing isomerically pure or highly isomerically-enriched cis- or trans- (2-isobutyl-4-methyl-tetrahydropyran-4-yl) acetate, a process for imparting and / or enhancing an odor or taste of a product and perfumed or flavored products containing isomerically pure or highly isomerically-enriched cis- or trans- (2-isobutyl-4-methyl-tetrahydropyran-4-yl) acetate.
• Aromachemikalie, z. B. for the production of fragrance compositions, suitable. It would be desirable if further Aromachemikalien could be prepared by simple derivatization of these 2-substituted 4-hydroxy-4-methyl-tetrahydropyrans, resulting in new, inexpensive secondary products. It would also be desirable to use compounds in combination with 2-substituted ones
• EP 0383446 A2 describes the synthesis and the olfactory properties of a large number of different 2,4,4-trisubstituted tetrahydropyranyl esters.
• Example IX describes the synthesis of 2-isobutyl-4-methyl-tetrahydropyran-4-yl acetate by esterification of 2-isobutyl-4-hydroxy-4-methyl-tetrahydropyran with acetic anhydride in the presence of methanesulfonic acid. Although the reaction product was subjected to a fractional distillation. However, the fractions obtained were analyzed neither for the components contained nor for their olfactory properties. The NMR spectrum shown (FIG.
• the invention relates to the use of isomerically pure cis- (2-isobutyl-4-methyl-tetrahydropyran-4-yl) acetate of the formula (1.1) or of isomerically pure trans- (2-isobutyl-4-methyltetrahydropyran-4-yl ) acetate of the formula (I.2) or an isomer mixture of cis- (2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (1.1) and trans- (2-isobutyl-4-methyltetrahydropyran- 4-yl) acetate (I.2)
• Another object of the invention is a process for the preparation of isomerically pure cis- (2-isobutyl-4-methyl-tetrahydropyran-4-yl) acetate of the formula (1.1) or isomerically pure trans- (2-isobutyl-4-methyl-tetrahydropyran -4-yl) acetate of the formula (I.2) or a mixture of isomers of (1.1) and (I.2), wherein the weight fraction of (1.1) or the weight fraction of (I.2) in the isomer mixture, based on the total weight of (1.1) and (I.2), in in the range from 90% by weight to less than 100% by weight, in which i) a mixture of isomers of cis-2- (2-methylpropyl) -4-hydroxy-4-methyltetrahydropyran (11.1) and trans-2- (2-methylpropyl) -4-hydroxy-4-methyltetrahydropyran (II.2)
• step i) optionally subjecting the reaction mixture obtained in step i) to a separation to give at least one fraction, the isomerically pure (1.1) or isomerically pure (I.2) or an isomeric mixture of (1.1) and (I.2), wherein the weight fraction of (1.1) or the weight fraction of (I.2) in the isomer mixture, based on the Total weight of (1.1) and (I.2), in a range of 90 wt .-% to less than 100 wt .-% is.
• Another object of the invention is isomerically pure cis- (2-isobutyl-4-methyl-tetrahydropyran-4-yl) acetate of the formula (1.1).
• Another object of the invention is a mixture of isomers of cis- (2-isobutyl-4-methyl-tetrahydropyran-4-yl) acetate (1.1) and trans- (2-isobutyl-4-methyl-tetrahydropyran-4-yl) acetate ( I.2) in which the proportion by weight of cis- (2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (1.1) based on the total weight of cis- 2-isobutyl-4-methyl-tetra- hydropyran-4-yl) acetate (1.1) and trans- (2-isobutyl-4-methyl-tetrahydropyran-4-yl) acetate (I.2) in a range from 90% to less than 100% by weight. % lies.
• Another object of the invention is isomerically pure trans- (2-isobutyl-4-methyl-tetrahydropyran-4-yl) acetate of the formula (I.2).
• Another object of the invention is an isomer mixture of cis- (2-isobutyl-4-methyl-tetrahydropyran-4-yl) acetate (1.1) and trans- (2-isobutyl-4-methyl-tetrahydropyran-4-yl) acetate (I.2) in which the proportion by weight of trans- (2-isobutyl-4-methyl-tetrahydropyran-4-yl) acetate (I.2) based on the total weight of cis-2-isobutyl-
• Another object of the invention is a fragrance or flavoring composition
• a fragrance or flavoring composition comprising a) isomerically pure cis (2-isobutyl-4-methyl-tetrahydropyran-4-yl) acetate of the formula
• Another object of the invention is a method for lending and / or replacing and / or enhancing an odor or taste of a product with a fresh-floral note, especially a heavy lilac note, a citrus note, especially a bergamot-like note, such.
• Another object of the invention is a method for imparting and / or enhancing a smell or taste of a product with a jasmine-like note, a leathery note or a strong fruity note, in which the product is reacted with an organoleptically effective amount of an isomerically pure trans- ( 2-isobutyl-4-methyl-tetrahydropyran-4-yl) acetate of the formula (1.1) or a mixture of isomers, wherein the proportion by weight of trans- (2-isobutyl-4-methyl-tetrahydropyran-4-yl) acetate (1.1) based to the total weight of cis-2-isobutyl-4-methyl-tetrahydropyran-4-yl) acetate (1.1) and trans- (2-isobutyl-4-methyl-tetrahydropyran-4-yl) acetate (I.2) in one From 90 wt .-% to less than 100 wt .-%, is brought into contact
• Another object of the invention is a perfumed or flavored product comprising an organoleptically effective amount of isomerically pure cis- (2-isobutyl-4-methyl-tetrahydropyran-4-yl) acetate of the formula (1.1) or isomerically pure trans- (2- isobutyl-4-methyl-tetrahydropyran-4-yl) acetate of formula (I.2) or highly isomerically enriched (1.1) or highly isomerically enriched (I.2), or comprising an organoleptically effective amount of a fragrance or flavoring composition of the invention, as defined before and below.
• Another object of the invention is the use of isomerically pure cis- (2-isobutyl-4-methyl-tetrahydropyran-4-yl) acetate of the formula (1.1) or an isomer mixture, wherein the weight fraction of cis- (2-isobutyl- 4-methyl-tetrahydropyran-4-yl) acetate (1.1), based on the total weight of cis-2-isobutyl-4-methyl-tetrahydropyran-4-yl) acetate (1.1) and trans- (2-isobutyl- 4-methyl-tetrahydropyran-4-yl) acetate (I.2) ranges from 90% to less than 100% by weight, for the partial or total replacement of linalyl acetate in a linalyl acetate containing fragrance or flavoring composition or in a linalyl acetate perfumed or flavored product.
• trans- (2-isobutyl-4-methyl-tetrahydropyran-4-yl) acetate all enantiomers in pure form, optically active mixtures of the enantiomers of these compounds and optically inactive racemates of cis- (l.1) and trans- (l.2). If, in the following, cis and trans diastereomers of the compounds (1.1) or (I.2) are mentioned, only one of the enantiomeric forms is depicted in each case. By way of illustration only, the isomers of 2-isobutyl-4-methyl-tetrahydropyran-4-yl) acetate are shown below:
• the compound of formula (1.1) can be used in stereoisomerically pure form or as (2S, 4S) and (2R, 4R) -isomerengemisch.
• the compound of formula (I.2) can be used in stereoisomerically pure form or as (2S, 4R) and (2R, 4S) -isomerengemisch.
• optically inactive racemates are used according to the invention.
• the pure cis isomer is referred to as isomerically pure cis (2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (1.1).
• An isomerically pure cis- (2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (1.1) contains no (ie 0% by weight) trans- (2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (I.2).
• the term "isomerically pure" in this context refers only to the cis / trans isomerism and not the enantiomer.
• the pure trans isomer is referred to as isomerically pure trans- (2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (I.2).
• An isomerically pure trans- (2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (I.2) contains no (ie 0% by weight) cis (2-isobutyl-4-methyl) tetrahydropyran-4-yl) acetate (1.1).
• the term "isomerically pure" in this context refers only to the cis / trans isomerism and not the enantiomerism.
• highly isomerically enriched (1.1) has a weight fraction of cis (2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (1.1) based on the total weight of cis-2-isobutyl-4-methyltetrahydropyran-4 yl) acetate (1.1) and trans- (2-isobutyl-4-methyl-tetrahydropyran-4-yl) acetate (I.2) from 90 to 99.999% by weight, particularly preferably from 92 to 99.99% by weight. %, in particular from 95 to 99.9 wt .-% to.
• Highly isomerically enriched (I.2) preferably has a weight fraction of trans- (2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (I.2) based on the total weight of cis-2-isobutyl-4-methyl- tetrahydropyran-4-yl) acetate (1.1) and trans- (2-isobutyl-4-methyl-tetrahydropyran-4-yl) acetate (I.2) from 90 to 99.999% by weight, particularly preferably from 92 to 99, 99 wt .-%, in particular from 95 to 99.9 wt .-% to.
• an organoleptically effective amount is to be understood as meaning an amount which, when used appropriately, is sufficient to cause a scent impression on the user or consumer.
• isomerically pure or highly isomerically enriched 1.1
• isomerically pure or highly isomerically enriched I.2
• the preparation of isomerically pure or isomerically enriched (2-isobutyl-4-methyl-tetrahydropyran-4-yl) acetate preferably comprises an esterification of a 2-isopropyl-4-hydroxy-4-methyltetrahydropyran of the general formula (II).
• the conversion of the 2-isopropyl-4-hydroxy-4-methyl-tetrahydropyran (II) into the corresponding acetates of the general formula (I) can be carried out by customary methods known to the person skilled in the art according to the following scheme.
• the configuration of the alcohol component (II) used generally does not change.
• isomerically pure or isomerically enriched (2-isobutyl-4-methyltetrahydropyran-4-yl) acetate it is therefore possible in a first embodiment to start from an isomerically pure alcohol component (II) or an alcohol component (II) which is already sufficiently high at the desired isomer enriched.
• isomerically pure alcohol component (II) or an alcohol component (II) which is already sufficiently high at the desired isomer enriched is already sufficiently high at the desired isomer enriched.
• a mixture of isomers used which is not yet enriched sufficiently high in the desired isomer and then isolated from the product of the esterification of a sufficiently enriched in the desired isomer fraction.
• the invention thus further provides a process for preparing isomerically pure (1.1) or isomerically pure (I.2) or highly isomerically enriched (1.1) or highly isomerically enriched (I.2) in which i) isomer mixture from cis-2- (2-methylpropyl) -4-hydroxy-4-methyltetrahydropyran (11.1) and trans-2- (2-methylpropyl) -4-hydroxy-4-methyltetrahydropyran (II.
• step i) of a separation to obtain at least one fraction which contains isomerically pure (1.1) or isomerically pure (I.2) or highly isomerically enriched (1.1) or highly isomerically enriched (I.2).
• esterification catalyst customary catalysts can be used, for.
• mineral acids such as sulfuric acid and phosphoric acid
• organic sulfonic acids such as methanesulfonic acid and p-toluenesulfonic acid
• amphoteric catalysts especially titanium, tin (IV) - or zirconium compounds, such as tetraalkoxytitans, z.
• tetrabutoxytitanium, and tin (IV) oxide customary catalysts can be used, for.
• mineral acids such as sulfuric acid and phosphoric acid
• organic sulfonic acids such as methanesulfonic acid and p-toluenesulfonic acid
• amphoteric catalysts especially titanium, tin (IV) - or zirconium compounds, such as tetraalkoxytitans, z.
• tetrabutoxytitanium, and tin (IV) oxide As tetrabutoxytitan
• the esterification catalyst is used in an effective amount, which is usually in the range of 0.05 to 10 wt .-%, preferably 0.1 to 5 wt .-%, based on the sum of acid component (or anhydride) and alcohol component.
• the esterification can usually be carried out at ambient pressure or reduced or elevated pressure. Preferably, the esterification is carried out at ambient or reduced pressure.
• the esterification may be carried out in the absence of an added solvent or in the presence of an organic solvent. If the esterification is carried out in the presence of a solvent, it is preferably an organic solvent which is inert under the reaction conditions.
• the solvent is preferably selected from pentane, hexane, heptane, ligroin, petroleum ether, cyclohexane, dichloromethane, trichloromethane, carbon tetrachloride, benzene, toluene, xylene, chlorobenzene, dichlorobenzenes, dibutyl ether, THF, dioxane and mixtures thereof.
• the esterification is usually carried out in a temperature range of 0 to 200 ° C, preferably 10 to 150 ° C.
• the esterification can take place in the absence or in the presence of an inert gas.
• An inert gas is generally understood to mean a gas which, under the given reaction conditions, does not react with the starting materials, reagents, solvents or the products formed during the reaction. These include z. As nitrogen or argon.
• the preparation of an isomerically pure cis is generally understood to mean a gas which, under the given reaction conditions, does not react with the starting materials, reagents, solvents or the products formed during the reaction. These include z. As nitrogen or argon.
• a 2-isopropyl-4-hydroxy-4-methyl-tetrahydropyran be used with any cis / trans ratio. This may, for example, be technically bare streams from the synthesis of 2-isopropyl-4-hydroxy-4-methyl-tetrahydropyran or their workup act.
• Suitable apparatus for distillative separation include distillation columns, such as tray columns, which may be equipped with bells, sieve plates, sieve trays, packings, packing, valves, side draws, etc., evaporators, such as thin film evaporator, falling film evaporator, forced circulation evaporator, Sambay evaporator, etc., and Combinations of it.
• the distillation columns can have separating internals, which are preferably selected from separating trays, ordered packings, eg. As sheet or tissue packs, such as Sulzer Mellapak®, Sulzer BX, Montz B1 or Montz A3 or Kühni Rombopak, or random beds of packing, such. Dixon rings, Raschig rings, high flow rings or Raschig super rings. Orderly packs, preferably sheet metal or fabric packings, with a specific surface area of 100 to 750 m 2 / m 3 , in particular 250 to have proven particularly useful
• the process described above makes it possible to provide isomerically pure or highly isomerically enriched cis- or trans- (2-isobutyl-4-methyltetrahydropyran-4-yl) acetate.
• the cis- (2-isobutyl-4-methyltetrahydropyran-4-yl) acetate of the formula (1.1) according to the invention and used according to the invention has a weight fraction of cis- (2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (1.1) based on the total weight of cis-2-isobutyl-4-methyl-tetrahydropyran-4-yl) acetate (1.1) and trans- (2-isobutyl-4-methyl-tetrahydropyran-4-yl) acetate (I. 2) from 90 to 100 wt .-%, preferably from 90 to 99.999 wt .-%, particularly preferably from 92 to 99.99 wt
• the trans- (2-isobutyl-4-methyltetrahydropyran-4-yl) acetate of the formula (I.2) according to the invention and used according to the invention has a weight fraction of trans- (2-Isobutyl-4-methyl-tetrahydropyran-4-yl) acetate (I.2) based on the total weight of cis-2-isobutyl-4-methyl-tetrahydropyran-4-yl) acetate (1.1) and trans- ( 2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (I.2) from 90 to 100% by weight, preferably from 90 to 99.999% by weight, more preferably from 92 to 99.99% by weight %, in particular from 95 to 99.9 wt .-% to.
• a preferred embodiment is the use of isomerically pure or highly isomerically-enriched (1.1) to produce a fragrance having a lilac-like note, a bergamot-like note, a linalyl acetate-like note, a woody note or a pepper / nutmeg note.
• Another preferred embodiment is the use of isomerically pure or highly isomerically-enriched (I.2) for the production of a fragrance with a jasmine-like note, a leathery note or a strong fruity note.
• I.2 isomerically pure or highly isomerically-enriched
• Another preferred embodiment is the use of isomerically pure or highly isomerically-enriched (1.1) to partially or completely replace linalyl acetate in a linalyl acetate-containing fragrance or flavoring composition or in a linalyl acetate perfumed or flavored product.
• the isomerically pure or highly isomerically enriched cis- or trans- (2-isobutyl-4-methyltetrahydropyran-4-yl) acetate used according to the invention and in accordance with the invention is used in a preferred embodiment of the invention in combination with at least one other of the compounds (1.1) and (I.2) various Aromachemikalie used.
• the aroma chemicals other than the compounds (1.1) and (I.2) are fragrances.
• Fragrance composition according to the invention then contain, for example, 1, 2, 3, 4, 5, 6, 7, 8 or more further fragrance substances.
• Extracts from natural raw materials such as essential oils, concretes, absolues, resines, resinoids, balms, tinctures such.
• ambergris tincture Amyrisöl; Angelica seed oil; Angelica root oil; anise oil; Valerian oil; Basil oil; Tree moss absolute; Bay oil; Mugwort oil; Benzoeresin; Bergamot oil; Bee wax absolute; birch tar; Bitter almond oil; Savory oil; Buccorightöl; Caboevuva oil; cade oil; calamus; camphor oil; Cananga oil; cardamom; Cascarillaöl; Casssiaoil; Cassie absolute; Castoreum absolute; Cedern thoroughöl; cedarwood; cistus; citronella; lemon; copaiba balsam; Copaivabalsamöl; Coriander oil; costus root; Cuminöl; Cypress oil; Davanaöl; Dill herb oil; Dill seed oil; Eau de Brouts absolute; Egg moss absolute; elemi; Tarragon oil; Eucalyptus citriodora oil; eucalyptus oil;
• fragrances from the group of hydrocarbons such as. 3-carene; alpha pinene; beta-pinene; alpha-terpinene; gamma-terpinene; p-cymene; bisabolene; camphene; caryophyllene; cedrene; farnesene; limonene; longifolene; myrcene; ocimene; valencene; (E, Z) -1, 3,5-undecatriene; styrene; diphenylmethane; the aliphatic alcohols such.
• menthone menthone
• menthone menthone
• ketones such as well as their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglinates and 3-methyl-2-
• 8-mercaptomenthan-3-one carvone; camphor; fenchon; alpha-ionone; beta-ionone;
• Cyclododecyl methyl ether 1, 1-dimethoxycyclododecane; (Ethoxymethoxy) cyclododecane; alpha-Cedrenepoxid; 3a, 6, 6, 9a tetramethyldodecahydronaphtho [2,1-b] furan; 3a-ethyl-6,6,9a-trimethyldodecahydronaphtho [2,1-b] furan; 1, 5,9-trimethyl
• 2-phenylethyl alcohol 3-phenylpropanol; 2-phenylpropanol; 2-phenoxyethanol; 2,2-dimethyl-3-phenylpropanol; 2,2-dimethyl-3- (3-methylphenyl) propanol;
• 1,1-dimethyl-2-phenylethyl alcohol 1, 1-dimethyl-3-phenylpropanol; 1-ethyl-1-methyl-3-phenylpropanol; 2-methyl-5-phenylpentanol; 3-methyl-5-phenylpentanol; 3-phenyl-2-propene-1-ol; 4-methoxybenzyl; 1 - (4-isopropylphenyl) ethanol; the ester of araliphatic alcohols and aliphatic carboxylic acids such.
• 2-Phenylethylisovalerianat 1-phenylethyl acetate; alpha-Trichlormethylbenzylacetat; alpha, alpha-dimethylphenylethyl acetate; alpha, alpha-dimethylphenylethyl butyrate;
• benzoic acid phenylacetic acid; methylbenzoate; ethyl benzoate; hexyl benzoate; Benzyl benzoate; methyl phenylacetate; ethyl phenylacetate; geranyl phenylacetate; Phenylethylphe- acetate; Methylcinnmat; ethylcinnamate; Benzyl; Phenylethylcinnamat;
• cinnamyl cinnamate allyl phenoxyacetate; methyl salicylate; isoamyl; hexyl salicylate; cyclohexyl; Cis-3-hexenyl salicylate; benzyl; phenylethyl;
• Eg estragole anethole; eugenol; Ethylenyl methyl ether; isoeugenol; Isoeugenylmethylether; thymol; carvacrol; diphenyl ether; beta-naphthyl methyl ether; beta-Naphthylethylether; beta-Naphthylisobutylether;
• the other aromatic chemical other than the compounds (1.1) and (I.2) is preferably selected from 2-isobutene-4-methyltetrahydro-2H-pyran-4-ol, linalyl acetate, 7-hydroxy-3,7 dimethyl octanal, 4-isopropylcyclohexylmethanol, 4- (octahydro-4,7-methano-5H-inden-5-ylidene) butanal, 4- (4-hydroxy-4-methylpentyl) -3-cyclohexene-1-carboxaldehyde, 3- (4-Hydroxy-4-methylpentyl) -3-cyclohexene-1-carboxaldehyde, 2,5,7,7-tetramethyloctanal, 2-methyl-3- (4-tert-butylphenyl) propanal, 3- (4 tert-butyl phenyl) propanal, linalool, ethyllinalool, tetrahydr
• Another object of the invention is a fragrance or flavoring composition containing isomerically pure cis- (2-isobutyl-4-methyl-tetrahydropyran-4-yl) acetate of the formula (1.1) or isomerically pure trans- (2-isobutyl-4-methyl) tetrahydropyran-4-yl) acetate of the formula (I.2) or a mixture of isomers of cis- (2-isobutyl-4-methyl-tetrahydropyran-4-yl) acetate (1.1) and trans- (2-isobutyl-4 methyl-tetrahydropyran-4-yl) acetate (I.2), wherein the proportion by weight of cis (2-isobutyl-4-methyl-tetrahydropyran-4-yl) acetate (1.1) relative to the total weight of cis 2-isobutyl-4-methyltetrahydropyran-4-yl) acetate (1.1) and trans- (2-
• the fragrance or flavoring composition according to the invention preferably contains component a) in a proportion by weight of from 0.1 to 95% by weight, particularly preferably from 0.1 to 90% by weight, in particular from 0.1 to 80% by weight. , based on the total weight of the composition.
• the fragrance or flavoring composition of the present invention contains component a) in an amount by weight of from 0.1 to 70% by weight, more preferably from 1 to 50% by weight, based on the total weight of the composition.
• the fragrance or flavoring agent according to the invention contains Composition component a) in a weight fraction of 2 to 30 wt .-%, more particularly 3 to 15 wt .-%, based on the total weight of the composition.
• the fragrance or aroma composition according to the invention comprises component a) as the sole aroma chemical.
• the fragrance or aroma composition according to the invention contains at least one further aroma chemical b) other than the compounds (1.1) and (I.2).
• Suitable further aroma chemicals b) are those mentioned above, to which reference is made in its entirety.
• the weight-amount ratio of component a) to component b) is preferably in a range from 100: 1 to 1: 100, particularly preferably from 50: 1 to 1:50.
• the fragrance or flavoring composition may optionally contain at least one diluent c).
• Suitable diluents may be used singly or as a mixture of 2 or more than 2 diluents. Suitable diluents are those commonly used as solvents for fragrances or flavorings.
• the fragrance or flavoring composition contains as diluent c) at least one compound which is liquid at 20 ° C and 1013 mbar.
• the compounds of component a) in component c) preferably have a solubility at 20 ° C. of at least 0.1 mg / ml, more preferably of at least 0.5 mg / ml. If present, the compounds of component b) in component c) preferably have a solubility at 20 ° C. of at least 0.1 mg / ml, more preferably of at least 0.5 mg / ml.
• Component c) is preferably selected from aliphatic and cycloaliphatic monoalcohols, polyols, open-chain aliphatic ethers, cyclic ethers, polyol mono- and polyethers, esters and mixtures thereof.
• Suitable aliphatic and cycloaliphatic monoalcohols are, for. As ethanol, n-propanol, isopropanol n-butanol, sec-butanol, tert-butanol and cyclohexanol.
• Suitable polyols are ethylene glycol, propylene glycol, 1,2-butylene glycol, diethylene glycol, dipropylene glycol or glycerol.
• Suitable open-chain aliphatic ethers and cyclic ethers are, for. As diethyl ether, dipropyl ether, diisopropyl ether, methyl tert-butyl ether, tetrahydrofuran, tetrahydropy- ran, 1, 4-dioxane or morpholine.
• Suitable polyol mono- and polyethers are, for. Example, ethylene glycol monomethyl ether, ethylene glycol dimethyl ether, ethylene glycol monoethyl ether, ethylene glycol diethyl ether, propylene glycol monoethyl ether, propylene glycol diethyl ether or Diethylenglycomono- ethyl ether.
• Suitable esters are ethyl acetate, methyl acetate, propyl acetate, isopropyl acetate, n-butyl acetate, sec-butyl acetate, tert-butyl acetate, isobutyl acetate, isoamyl acetate, ethyl butyrate, ethyl lactate, diethyl carbonate, ethylene carbonate, propylene carbonate, triethyl citrate, isopropyl myristate, diethyl phthalate, dialkyl ester of 1 , 2-cyclohexanedicarboxylic acid, especially 1, 2-cyclohexanedicarboxylic acid diisononyl ester (Hexamoll® DINCH, BASF SE), etc. Perfumed or flavored product
• the isomerically pure or highly isomerically enriched, cis or trans (2-isobutyl-4-methyltetrahydropyran-4-yl) acetate according to the invention and used according to the invention can be incorporated into a number of products or applied to such products.
• Fragrances according to the invention can be used in the production of perfumed articles.
• the olfactory properties as well as the material properties (such as solubility in common solvents and compatibility with common other constituents of such products) and the toxicological harmlessness of the fragrances according to the invention underline their particular suitability for the stated purposes.
• the positive properties contribute to the fact that the fragrances used according to the invention and the perfume compositions according to the invention are particularly preferably used in perfumery products, personal care products, hygiene articles, textile detergents and in cleaners for solid surfaces.
• the perfumed article is z. B. selected from perfumery products, personal care products, hygiene articles, laundry detergents and detergents for solid topical areas. Preferred perfumed articles according to the invention are furthermore selected from:
• Perfumery products selected from perfume extracts, eau de perfume, eau de toilette, eau de colognes, eau de solide, extract perfume, air freshener in liquid, gel or solid support form, aerosol sprays, fragrance cleaners and oils;
• Personal care products selected from shaving lotions, pre-shave products, splash colognes, solid and liquid soaps, shower gels, shampoos, shaving soaps, shaving creams, bath oils, oil-in-water cosmetic emulsions, water-in-oil emulsions and of the water-in-oil-in-water type such as.
• Hair sprays hair gels, hair lotions, hair conditioners, hair shampoo, permanent and semipermanent hair dyes, hair styling agents such as cold whiskers and hair straighteners, hair lotions, hair creams and lotions, deodorants and antiperspirants such as hair sprays.
• hair styling agents such as cold whiskers and hair straighteners
• hair lotions hair creams and lotions
• deodorants and antiperspirants such as hair sprays.
• Sanitary articles selected from among candles, lamp oils, incense sticks, insecticides, repellents, fuels, rust removers, scented towelettes, underarm pads, baby diapers, sanitary napkins, toilet paper, facial tissues, handkerchiefs, douche utensils;
• Solid surface cleaners selected from perfumed acidic, alkaline and neutral detergents, such as: B. Floor cleaners, window glass cleaners, dishwashing detergents, bathroom and sanitary cleaners, scouring cream, solid and liquid toilet cleaners, powder and foam carpet cleaners, waxes and polishes such as furniture polishes, floor waxes, shoe creams, disinfectants, surface disinfectants and sanitary cleaners, brake cleaners, pipe cleaners, Decalcifiers, grill and oven cleaners, algae and moss removers, mold removers, facade cleaners;
• Laundry detergents selected from among liquid detergents, powdered detergents, laundry pre-treatment agents such as bleaches, soaking and stain removers, fabric softeners, laundry soap, washing tablets.
• the fragrances used according to the invention and the fragrance substance compositions according to the invention are suitable for use in surfactant-containing perfumed articles. We are looking for - especially for the perfuming of surfactant-containing formulations such. As cleaning agents (especially dishwashing detergent and all-purpose cleaner) - often fragrances and / or fragrance compositions with a rose head note and pronounced naturalness.
• fragrances and fragrance compositions according to the invention can be used rosy as agents for providing (a) hair or (b) textile fibers with the odor note.
• fragrances and fragrance compositions according to the invention to be used according to the invention are therefore particularly suitable for use in surfactant-containing perfumed articles.
• the perfumed article is one of the following:
• an acidic, alkaline or neutral detergent selected in particular from the group consisting of all-purpose cleaners, floor cleaners, window glass cleaners, dishwashing detergents, bath and sanitary cleaners, scouring cream, solid and liquid toilet cleaners, powder and foam carpet cleaners, liquid detergents , powdered detergents, laundry pre-treatment agents such as bleaches, soak and stain removers, fabric conditioners, laundry soaps, washing tablets, disinfectants, surface disinfectants,
• an air freshener in a liquid, gelatinous or solid support form or as an aerosol spray in a liquid, gelatinous or solid support form or as an aerosol spray
• a wax or a polish selected in particular from the group consisting of furniture polishes, floor waxes and shoe creams, or
• a personal care product selected in particular from the group consisting of shower gels and shampoos shaving soaps, shaving foams, bath oils, oil-in-water, water-in-oil and water-in-oil-in-water cosmetic emulsions Type such.
• Hairsprays hair gels, firm hair lotions, hair rinses, permanent and semipermanent hair dyes, hair styling agents such as cold waving and hair straightening agents, hair lotions, hair creams and lotions, deodorants and so on. tiperspirants such. As underarm sprays, roll-ons, deodorants, deodorants, decorative cosmetics products.
• fragrances or fragrance compositions according to the invention are, for example: preservatives, abrasives, anti-acne agents, anti-aging agents, antibacterial agents, anti-cellulite agents, anti-dandruff agents, antiinflammatory agents, anti-irritants, anti-irritants Agents, anti-microbial agents, antioxidants, astringents, antiperspirants, antiseptics, antistatic agents, binders, buffers, excipients, chelating agents, cell stimulants, cleansing agents, skin care agents, depilatory agents, surfactants, deodorants, antiperspirants, emollients, emulsifiers, enzymes, essentials Oils, fibers, film formers, fixatives, foaming agents, foam stabilizers, substances for preventing foaming, foam boosters, fungicides, gelling agents, yellowing agents, hair care products, hair shaping preparations, hair glues saturating agents, moisturizing agents, moisturizing substances,
• the fragrances are used in the preparation of the perfumed articles in liquid form, neat or diluted with a solvent or in the form of a fragrance composition.
• Suitable solvents for this are those mentioned above as component c). These are referred to in their entirety.
• the fragrances and / or fragrance compositions contained in the perfumed articles according to the invention may in one embodiment be absorbed on a carrier which is responsible for both a fine distribution of the fragrance or the odoriferous substance.
• Substance composition in the product as well as for a controlled release in the application ensures.
• Such carriers can be porous inorganic materials such as light sulfate, silica gels, zeolites, gypsum, clays, clay granules, aerated concrete, etc., or organic materials such as woods and cellulosic based materials.
• fragrances used according to the invention and the perfume compositions according to the invention can also be microencapsulated, spray-dried, present as inclusion complexes or as extruded products and added in this form to the product or article to be perfumed.
• the properties can be further optimized by so-called “coating” with suitable materials with a view to a more targeted fragrance release, including preferably waxy plastics such.
• suitable materials including preferably waxy plastics such.
• polyvinyl alcohol can be used.
• the microencapsulation can be achieved, for example, by the so-called coacervation method with the aid of capsule materials, eg. As polyurethane-like substances or soft gelatin done.
• the spray-dried perfume oils can be prepared, for example, by spray-drying an emulsion or dispersion containing the perfume oil, it being possible to use as excipients modified starches, proteins, dextrin and vegetable gums.
• Inclusion complexes may, for. B. by introducing dispersions of fragrance compositions and cyclodextrins or urea derivatives in a suitable solvent, for. As water, are produced.
• Extrusion products can be prepared by fusing fragrances according to the invention and fragrance compositions according to the invention with a suitable waxy substance and by extrusion with subsequent solidification, if appropriate in a suitable solvent, for. For example, isopropanol.
• Diagram 1 Composition of the fractions in GC-FI.% Of the distillation of pyranol acetate
• High-cis-pyranol acetate (> 99% cis- (2-isobutyl-4-methyl-tetrahydropyran-4-yl) acetate of the formula (1.1)): a lilac-like note, a strong, clear bergamot-like note, a linalyl acetate-like note, a woody note Note as well as a pepper / nutmeg note.
• High-trans-pyranol acetate (> 98% trans- (2-isobutyl-4-methyl-tetrahydropyran-4-yl) -acetate of the formula (I.2)): jasmine-like note, a leathery note and a strong fruity note.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Engineering & Computer Science (AREA)
• Life Sciences & Earth Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Polymers & Plastics (AREA)
• Nutrition Science (AREA)
• Health & Medical Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Wood Science & Technology (AREA)
• Food Science & Technology (AREA)
• Fats And Perfumes (AREA)
• Cosmetics (AREA)
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• Pyrane Compounds (AREA)
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• Detergent Compositions (AREA)
• Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

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• 2015
  • 2015-09-25 JP JP2017516116A patent/JP6822948B2/ja active Active
  • 2015-09-25 CN CN201580051668.1A patent/CN106715408B/zh active Active
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