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
  • C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring

Definitions

• the present invention relates to the use of 4-phenyl-pentan-2-ol as a fragrance and flavoring.
• the invention also relates to perfumed or flavored articles comprising this compound and corresponding methods for imparting, modifying and / or enhancing certain odor and / or flavor notes. Also described are processes for the preparation of 4-phenyl-pentan-2-ol.
• fragrances with interesting green notes which are able (in fragrance compositions) in addition to a green fragrance note other interesting odor notes, such as fruity notes to produce and expand with their novel or original fragrance properties, the possibilities of perfumers.
• fragrances with green and fruity scents which are able to enter into a harmonious combination with floral-scented fragrances.
• a superimposition of the different odoriferous aspects and notes should take place in order thereby to produce an overall complex olfactory impression.
• fragrances with special odor properties which are suitable to serve as the basis for the composition of novel modern perfumes with a complex odor character.
• Preferred fragrances sought after should have, in addition to a green, fruity scent, further notes and aspects that give them an odor character and complexity.
• fragrances with green, fruity notes which are preferably paired with other interesting and original odor properties, allowing the fragrances sought novel and original fragrance compositions with specific odor notes and aspects.
• fragrances with green, fruity notes should be found, which in particular are suitable for combination with fragrances which have a woody and / or floral scent.
• the perfumes that accomplish this main purpose should also preferably have additional positive secondary properties beyond their primary, namely, odoriferous, properties, such as, e.g. a higher stability under certain conditions of use, a higher yield, a better adhesion, a high substantivity, a remarkable booster effect or a strong blooming, so that sensory remarkable effects or else better dermatological and toxicological properties can be achieved compared to similar fragrances.
• additional positive secondary properties beyond their primary, namely, odoriferous, properties, such as, e.g. a higher stability under certain conditions of use, a higher yield, a better adhesion, a high substantivity, a remarkable booster effect or a strong blooming, so that sensory remarkable effects or else better dermatological and toxicological properties can be achieved compared to similar fragrances.
• the primary object is achieved by the use of 4-phenyl-pentan-2-ol of the formula (I) as a scent or flavoring.
• the 4-phenyl-pentan-2-ol of the formula (I) to be used according to the invention has two chiral centers.
• the compound of formula (I) may be syn- or anticonfigured, as (R, R) -configured enantiomer, (R, S) -configured enantiomer, (S, R) -configured enantiomer, (S, S) -configured or as any mixture of the enantiomers, in particular as a racemate, or else as any desired mixture of the corresponding diastereomers.
• the odor properties of the compound 4-phenyl-pentan-2-ol of the formula (I) to be used according to the invention are described by the perfumers as follows: very strong, interesting green, fruity scent in the direction of grapefruit and rhubarb, very natural odor impression.
• the compound of formula (I) can be used for imparting, modifying and / or enhancing a green, fruity odor and / or flavor note.
• a certain structural similarity of the compound of the formula (I) to be used according to the invention also exists for the tertiary alcohol 4-phenyl-2-methyl-2-butanol ( ⁇ , ⁇ -dimethylphenylethylcarbinol) which is known as a fragrance but which has a dry, rosy-floral, lily-like odor.
• the field of phenylpentanols has been well studied, and therefore it is particularly unexpected that another valuable fragrance could be found in this field.
• the compound of the formula (I) has completely independent olfactory properties, which stand out clearly from the known fragrances of similar structure.
• the suitability of the compound of the formula (I) to be used according to the invention as a fragrance or flavoring agent for use in the olfactory and flavor industry has hitherto not been known and is surprising.
• the 4-phenyl-pentan-2-ol to be used according to the invention has, in addition to the green-fruity aspects, an expressive rhubarb note with additional, sometimes very complex and multi-faceted aspects, because it differs due to the presence of these additional additional aspects the compound to be used according to the invention is very distinct from structurally comparable and known substances (see above) and gives a very complex and varied odor and taste impression that can otherwise be achieved only by complex mixtures of several components (such as essential oils or herbal or spice mixtures).
• the 4-phenylpentan-2-ol to be used according to the invention can intensify the intensity of a fragrance mixture even at low dosages and round off and harmonize the overall appearance of the fragrance mixture and impart more (off) radiation and naturalness to the mixture ,
• the present invention also relates to the use for providing (a) hair, (b) skin or (c) textile fibers with a fragrance, in particular a green fruity fragrance (with regard to further odor or taste notes, see above).
• the present invention also relates to corresponding processes and (preferably surfactant-containing) mixtures.
• the present invention also relates to the use of 4-phenyl-pentan-2-ol as an agent for increasing the substantivity and / or retention of a fragrance mixture and / or fixator and / or as an agent for increasing the surfactant-containing aqueous Solution of perceived odor of other fragrances.
• the 4-phenyl-pentan-2-ol to be used according to the invention has, in addition to its primary, namely olfactory properties, additional positive secondary properties, such as, for example, B. a high stability under certain conditions of use, high yield, good adhesion, high substantivity.
• 4-phenyl-pentan-2-ol of the formula (I) can be used in particular to impart radiation, rounding off and / or harmony to an odor or aroma composition (off) and / or to intensify existing odor and / or taste notes.
• 4-phenyl-pentan-2-ol is usually used in sensory effective amounts in the context of the use according to the invention. Frequently, the 4-phenyl-pentan-2-ol to be used according to the invention should be mixed or combined with other fragrances or flavorings.
• the weight ratio of the total amount of 4-phenylpentan-2-ol to the total amount of further odorants or aromatic substances is then preferably in the range from 1: 1000 to 1: 0.5, preferably 1: 100 to 1: 0.5 ,
• An odoriferous or aromatic substance composition according to the invention can be prepared, for example, by mixing 4-phenylpentan-2-ol as component (a) with one or more further odoriferous or aromatic substances (as component (b)).
• component (a) is used regularly in an amount sufficient to impart, modify and / or enhance an odor or flavor note of the type green, fruity in the finished composition.
• a fragrance or flavoring composition according to the invention preferably comprises a total amount of 4-phenylpentan-2-ol (component (a)) in the range of 0.01 to 50 wt .-%, preferably 0.1 to 25 wt .-% and particularly preferably from 0.5 to 20% by weight, based on the total amount of the fragrance or flavoring composition.
• the 4-phenyl-pentan-2-ol to be used according to the invention is mainly used to impart more (aus) radiation, rounding off and / or harmony to an odorant or flavoring composition and / or to reinforce certain notes, its total amount is preferably comparatively low and more preferably in the range of 0.01 to 5 wt .-%, preferably in the range of 0.1 to 2 wt .-%, based on the total amount of the fragrance or flavoring composition. If a comparatively low concentration is selected within the preferred concentration ranges, depending on the other components of the particular composition, in some cases the mediation of the abovementioned odor or taste notes does not yet occur.
• the preparation of the 4-phenyl-pentan-2-ol to be used according to the invention can be carried out by means of known reactions and processes.
• 4-phenyl-pentan-2-ol of the formula (I) can be prepared on the basis of the literature ( Journal f. Prakt. Chemie volume 319, No. 4, 1977, 601-610 ) are prepared via a catalytic cleavage of substituted 1,3-dioxanes of the formula (A) (see the following equation).
• Y is either hydrogen or an alkyl radical having 1 to 10 C atoms, preferably Y is methyl or ethyl.
• This educt itself has a scent towards grapefruit and rhubarb and can be excellently combined with 4-phenylpentan-2-ol to provide new articles such as fragrance or flavor compositions.
• the catalytic hydrogenation is preferably carried out in the presence of a hydrogenation catalyst in the range of 160-240 ° C at a hydrogen pressure in the range of 20 to 50.
• Suitable hydrogenation catalysts may include, for example, ruthenium, rhodium, iridium, nickel, palladium or platinum.
• Advantageous hydrogenation catalysts include palladium, platinum, ruthenium or rhodium, particularly preferred hydrogenation catalyst is (elemental) palladium.
• the hydrogenation catalysts to be used according to the invention can be applied to organic or inorganic support materials.
• the hydrogenation catalysts may contain a carrier material or mixtures of carrier materials.
• advantageous support materials may be mentioned: activated carbon, coal, aluminum oxides, Metal oxides, silica gels, zeolites, clays, clay granules, amorphous aluminosilicates and other inorganic carriers.
• a preferred carrier material is activated carbon.
• Very particularly preferred catalysts are palladium on activated carbon and palladium on alumina.
• the product mixture comprising 4-phenyl-pentan-2-ol can comprise residues of the dioxane of the formula (A) which, in particular in the case of the vertacetal, can contribute positively to the sensory overall impression.
• Fragrance or flavoring compositions according to the invention which contain 4-phenylpentan-2-ol of the formula (I) can be used in liquid form, undiluted or diluted with a solvent for perfuming or aromatization.
• Suitable solvents for this are e.g. Ethanol, isopropanol, diethylene glycol monoethyl ether, glycerin, propylene glycol, 1,2-butylene glycol, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate, triacetin, etc.
• Fragrance or flavoring compositions according to the invention containing 4-phenylpentan-2-ol of the formula (I) may be adsorbed on a carrier which promotes both a fine distribution of the odoriferous or aromatic substances in the product and a controlled release the application ensures.
• a carrier which promotes both a fine distribution of the odoriferous or aromatic substances in the product and a controlled release the application ensures.
• Such carriers can be porous inorganic materials such as light sulphate, silica gels, zeolites, gypsum, clays, clay granules, aerated concrete, etc. or organic materials such as woods, cellulosic substances, sugars, dextrins (eg maltodextrin) or plastics such as PVC, polyvinyl acetates or polyurethanes.
• inventive Composition and carrier is an exemplary article of the invention.
• Inventive fragrance or flavor compositions containing 4-phenyl-pentan-2-ol of formula (I) may also be microencapsulated, spray dried, as inclusion complexes or as extrusion products (i.e., inventive articles) and in this form e.g. B. to be perfumed or flavored product.
• compositions modified in this way can be further optimized by so-called “coating” with suitable materials with a view to a more targeted release of fragrance, to which end preferably wax-like plastics, such as e.g. Polyvinyl alcohol can be used.
• suitable materials such as e.g. Polyvinyl alcohol can be used.
• the microencapsulation of the odoriferous or flavoring compositions according to the invention to articles according to the invention can be carried out, for example, by the so-called coacervation method with the aid of capsule materials, e.g. made of polyurethane-like substances or soft gelatin.
• the spray-dried odoriferous or flavoring compositions can be prepared, for example, by spray-drying an emulsion or dispersion containing the fragrance or aroma composition, it being possible to use modified starches, proteins, dextrin and vegetable gums as carriers.
• Inclusion complexes can be e.g. by incorporating dispersions of the fragrance or flavoring composition and cyclodextrins or urea derivatives into a suitable solvent, e.g. Water, to be produced.
• Extrusion products may be made by fusing the fragrance or flavor compositions together with a suitable waxy substance and by extrusion followed by solidification, optionally in a suitable solvent, e.g. Isopropan
• 4-phenyl-pentan-2-ol of formula (I) and fragrance or flavor compositions containing 4-phenyl-pentan-2-ol can be used in concentrated form, in solutions or in modified form as described above for the preparation of inventive perfumed articles such.
• 4-phenyl-pentan-2-ol of the formula (I) can be incorporated into flavored or flavored articles, in particular in the diet, oral care or pleasure-serving preparations.
• the diet or pleasure-serving preparations are, for example, baked goods (eg bread, dry biscuits, cakes, other pastry), confectionery (eg chocolates, chocolate bar products, other bar products, fruit gums, hard and soft caramels, chewing gum), alcoholic or non-alcoholic beverages (eg Coffee, tea, wine, wine-based beverages, beer, beer-based drinks, liqueurs, schnapps, brandies, fruit-based sodas, isotonic drinks, soft drinks, nectars, fruit and vegetable juices, fruit or vegetable juice preparations), instant drinks (eg instant cocoa drinks, instant tea drinks, instant coffee drinks), meat products (eg ham, fresh sausage or raw sausage preparations) , spiced or marinated fresh or cured meat products), eggs or egg products (dry egg, egg whites, egg yolks), cereal products (eg breakfast cereals, muesli bars, pre-cooked finished rice products), dairy products (eg milk drinks, milk ice cream, yoghurt, kefir, cream cheese, soft cheese, hard cheese , Dried
• Formulations according to the invention can be applied, for example, to B. present as a semi-finished product or as seasoning mixture.
• Preparations according to the invention can serve, in particular, as semi-finished goods for the production of further preparations for nutrition or enjoyment, in particular in spray-dried form.
• Formulations according to the invention may also be in the form of capsules, tablets (non-coated and coated tablets, eg enteric coatings), dragees, granules, pellets, solid mixtures, dispersions in liquid phases, as emulsions, as powders, as solutions, as Pastes or other swallowable or chewable preparations as dietary supplements.
• Oral preparations according to the invention are, in particular, oral and / or dental care products such as toothpastes, tooth gels, tooth powders, mouthwashes, chewing gums and other oral hygiene products.
• customary active substances, basic substances, auxiliaries and additives for nutrition, oral care or pleasure-use preparations according to the invention can be used in amounts of 5 to 99.999999% by weight, preferably 10 to 80% by weight, based on the Total weight of the preparation to be included.
• the preparations may comprise water in an amount of up to 99.999999% by weight, preferably 5 to 80% by weight, based on the total weight of the preparation.
• Preparations according to the invention (as examples of articles according to the invention) containing 4-phenyl-pentan-2-ol are prepared according to a preferred embodiment by reacting the 4-phenyl-pentan-2-ol of the formula (I) as a substance, as a solution (eg B. in ethanol, water or 1,2-propylene glycol) or in the form of a mixture with a solid or liquid carrier (eg maltodextrin, starch, silica gel), other flavors or flavorings and optionally other auxiliaries and / or stabilizers (eg natural or artificial polysaccharides and / or vegetable gums such as modified starches or gum arabic) are incorporated into a nutritional, oral care or pleasure base preparation.
• a solution eg B. in ethanol, water or 1,2-propylene glycol
• a solid or liquid carrier eg maltodextrin, starch, silica gel
• other auxiliaries and / or stabilizers eg natural or artificial poly
• the spray-dried solid preparations according to the invention are particularly suitable as semi-finished goods for the production of further preparations according to the invention.
• the spray-dried solid preparations according to the invention preferably contain 50 to 95% by weight of excipients, in particular maltodextrin and / or starch, 5 to 40% adjuvants, preferably natural or artificial polysaccharides and / or vegetable gums such as modified starches or gum arabic.
• the 4-phenyl-pentan-2-ol and optionally other constituents of the preparation according to the invention are initially dissolved in emulsions, in liposomes, e.g. starting from phosphatidylcholine, in microspheres, in nanospheres or even in capsules, granules or extrudates of a matrix suitable for food and beverage, e.g.
• starch derivatives eg modified starch
• cellulose or cellulose derivatives eg hydroxypropylcellulose
• other polysaccharides eg dextrin, alginate, curdlan, carageenan, chitin, chitosan, pullulan
• natural fats eg beeswax, carnauba wax
• Proteins eg Gelatin or other natural products (e.g., shellac).
• the products may be obtained by spray drying, spray granulation, melt granulation, coacervation, coagulation, extrusion, melt extrusion, emulsion processes, coating or other suitable encapsulation processes and optionally a suitable combination of the abovementioned processes.
• the 4-phenylpentan-2-ol is first complexed with one or more complexing agents, for example cyclodextrins or cyclodextrin derivatives, preferably ⁇ - or ⁇ -cyclodextrin, and used in this complexed form.
• a preparation according to the invention in which the matrix is selected so that the 4-phenylpentan-2-ol of the formula (I) is released from the matrix in a delayed manner, so that a long-lasting effect is achieved.
• a fat, wax, polysaccharide or protein matrix is particularly preferred.
• auxiliaries and additives for foods or luxury foods for example water, mixtures of fresh or processed, vegetable or animal raw materials or raw materials (eg raw, roasted , dried, fermented, smoked and / or cooked meat, bones, cartilage, fish, vegetables, fruits, herbs, nuts, vegetable or fruit juices or pastes or their mixtures), digestible or non-digestible carbohydrates (eg sucrose, maltose, fructose , Glucose, dextrins, amylose, amylopectin, inulin, xylans, cellulose, tagatose), sugar alcohols (eg sorbitol, erythritol), natural or hardened fats (eg, tallow, lard, palm fat, coconut fat, hardened vegetable fat), oils (eg, sunflower oil, peanut oil, corn oil, olive oil, fish oil, soybean oil, sesame
• vegetable or animal raw materials or raw materials eg raw, roasted , dried, fermented, smoked and
• Dentifrices (as a base for oral care preparations) containing 4-phenylpentan-2-ol generally comprise an abrasive system (abrasives or abrasives) such as silicic acids, calcium carbonates, calcium phosphates, aluminas and / or hydroxyapatites.
• abrasive system abrasives or abrasives
• silicic acids such as silicic acids, calcium carbonates, calcium phosphates, aluminas and / or hydroxyapatites.
• surfactants such as sodium lauryl sulfate, sodium lauryl sarcosinate and / or cocamidopropyl betaine, humectants, such as glycerol and / or sorbitol, thickeners, such as carboxymethyl cellulose, polyethylene glycols, carrageenan and / or Laponite ®, sweeteners such as saccharin, flavor correcting agents for unpleasant taste impressions, taste corrigents for further , usually not unpleasant taste impressions, taste modulating substances (eg inositol phosphate, Nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances such as sodium glutamate or 2-phenoxypropionic acid), cooling agents such as menthol, menthol derivatives (eg L-menthol, L-menthyl lactate, L-menthyl alkyl carbonates, menthone ketals, menthane carboxylic acid amides), 2,2,2-
• Chewing gums (as another example of oral care preparations) containing 4-phenylpentan-2-ol generally comprise a chewing gum base, i. chewing gum that becomes plastic during chewing, sugar of various types, sugar substitutes, other sweet tasting substances, sugar alcohols, flavoring agents for unpleasant taste impressions, other flavor modulators for further, generally not unpleasant taste impressions, taste modulating substances (eg inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate or others Substances such as monosodium glutamate or 2-phenoxypropionic acid), humectants, thickeners, emulsifiers, flavors and stabilizers or odor remedies.
• a chewing gum base i. chewing gum that becomes plastic during chewing
• taste modulating substances eg
• the preparations according to the invention preferably contain an aroma composition in order to round off and refine the taste and / or smell of the preparation.
• Suitable (additional) flavoring compositions include e.g. synthetic, natural or nature-identical flavorings, fragrances and flavorings as well as suitable excipients and carriers.
• this perfume composition becomes fresher, brighter, more rounded and more harmonious with the addition of 3% by weight of 4-phenylpentan-2-ol from Example 2, adding a green-fruity and sweet note and the woody and floral notes Aspects are reinforced.
• the used 4-phenyl-pentan-2-ol of formula (I) gives the composition by its own odor and by its modifying and reinforcing effect (booster effect) has its own character and combines the different odoriferous elements.
• this perfume composition comes to life with the addition of 6% by weight of 4-phenylpentan-2-ol of the formula (I) from Example 1.
• the impression of flowery is greatly enhanced.
• the composition looks brighter, more rounded and more harmonious, adding a green-fruity and natural touch.
• the used 4-phenyl-pentan-2-ol of formula (I) gives the composition by its own odor and by its modifying and reinforcing effect (booster effect) has its own character and combines the different odoriferous elements.
• the pH of the shampoo base was about 6. From this, 100 ml of a 20 wt .-% aqueous shampoo solution were prepared. In this shampoo solution, 2 hair slides were washed together for 2 minutes and then rinsed for 20 seconds under running lukewarm water. One strand of hair was wet wrapped in aluminum foil and dried the second strand of hair with a hair dryer. Both strands of hair were judged by a panel odor.
• Odor description respectively: radiant, interesting green scent towards grapefruit and rhubarb, very natural aura.
• Example 3 The perfume composition of Example 3 (after addition of 3 wt .-% 4-phenyl-pentan-2-ol formula (I) from Example 2) was in a dosage of 0.5 wt .-% in a fabric softener base of the following composition incorporated: Quaternary ammonium methosulfate (esterquat), about 90% (eg Rewoquat WE 18, Fa. Witco Surfactants GmbH) 5.5% Alkyldimethylbenzylammonium chloride, about 50% (eg Preventol R50, Fa. Bayer AG) 0.2% Color solution, about 1% 0.3% water 94.0%
• the pH of the fabric softener base was in the range of 2 to 3.
• Two pieces of fabric were mixed with 370 g of a 1% aqueous fabric softener solution based on the fabric softener comprising 0.5% by weight of compound formula (I) -Ground mass in a Linetest machine in the softening program 30 minutes at 20 ° C rinsed.
• the flaps were wrung out and then spun for 20 seconds.
• a rag was wet-sealed, and one hung up to dry. Subsequently, both flaps were assessed by a panel odor.
• Odor description flowery, woody, fresh, radiant, green-fruity aspects with light sweet undertones, rounded and harmonious olfactory impression.
• Example 4 The perfume composition from Example 4 (after addition of 6% by weight of compound of formula (I) from Example 1) was incorporated in a dosage of 0.4% by weight into a base powder of the following formulation: Linear Na-alkylbenzenesulfonate 8.8% Ethoxylated fatty alcohol C12-18 (7 EO) 4.7% Na-soap 3.2% defoamers DOW CORNING (R) 2-4248S POWDERED ANTIFOAM, Silicone oil on zeolite as carrier material 3.9% Zeolite 4A 28.3% Na carbonate 11.6% Na salt of a copolymer of acrylic and maleic acid (Sokalan CP5) 2.4% Na silicate 3.0% carboxymethylcellulose 1.2% Dequest 2066 2.8% ([[(Phosphonomethyl) imino] bis [(ethylenitrilo) bis (methylene)]] tetrakisphosphonic acid, sodium salt) Optical brightener 0.2% Na sulfate 6.5% protease 0.4% sodium perbor
• Odor description in each case strongly flowery, radiant, green-fruity and natural note with slight sweet and woody undertones, rounded and harmonious olfactory impression.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Wood Science & Technology (AREA)
• Life Sciences & Earth Sciences (AREA)
• Fats And Perfumes (AREA)
• Cosmetics (AREA)
• Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
• Disinfection, Sterilisation Or Deodorisation Of Air (AREA)
• Detergent Compositions (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Liquid Carbonaceous Fuels (AREA)
• Seasonings (AREA)

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• 2006
  • 2006-09-11 DE DE102006043226A patent/DE102006043226A1/de not_active Withdrawn
• 2007
  • 2007-08-31 EP EP07115395A patent/EP1900800A3/fr not_active Withdrawn
  • 2007-09-10 US US11/852,577 patent/US20080064625A1/en not_active Abandoned
  • 2007-09-11 JP JP2007265929A patent/JP2008106271A/ja active Pending

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