[go: up one dir, main page]

EP1631247A1 - 2-methyle-5-phenylpentanal utilise comme senteur de rose - Google Patents

2-methyle-5-phenylpentanal utilise comme senteur de rose

Info

Publication number
EP1631247A1
EP1631247A1 EP04733350A EP04733350A EP1631247A1 EP 1631247 A1 EP1631247 A1 EP 1631247A1 EP 04733350 A EP04733350 A EP 04733350A EP 04733350 A EP04733350 A EP 04733350A EP 1631247 A1 EP1631247 A1 EP 1631247A1
Authority
EP
European Patent Office
Prior art keywords
methyl
rose
phenylpentanal
fragrance
scent
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP04733350A
Other languages
German (de)
English (en)
Inventor
Walter Kuhn
Lutz Walther
Horst Surburg
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Symrise AG
Original Assignee
Symrise AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from DE2003124018 external-priority patent/DE10324018A1/de
Priority claimed from DE2003125628 external-priority patent/DE10325628A1/de
Application filed by Symrise AG filed Critical Symrise AG
Publication of EP1631247A1 publication Critical patent/EP1631247A1/fr
Withdrawn legal-status Critical Current

Links

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
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds

Definitions

  • the present invention relates to the use of 2-methyl-5-phenylpentanal as a rose fragrance, i.e. as a means of creating, modifying or enhancing a rose scent. Further aspects of the invention emerge from the following description and the patent claims.
  • flower notes are of central importance. They form the so-called “heart note” of a perfume and determine the type of fragrance very significantly.
  • the most important floral notes used in perfumery are lily of the valley, rose and jasmine. Lily of the valley fragrance gives freshness and cleanliness, Rose fragrance gives elegance and ceremoniity, and the use of jasmine fragrance creates heavy, exotic and erogenous fragrance complexes.
  • fragrance due to their fragrance character, rose notes are of paramount importance for the composition of perfumes, especially those that are used for direct body perfuming on the skin, e.g. in alcoholic lotions and in cosmetic preparations such as skin creams.
  • Classic rose fragrances that are used in large quantities in the production of perfumes are e.g. Geraniol, citronellol and phenylethyl alcohol. These compounds also occur as the main components in natural extracts derived from rose petals. They are therefore particularly suitable for imitating the natural scent of roses.
  • 2-methyl-5-phenylpentanal has a rose odor which corresponds to the requirement profile outlined above.
  • 2-methyl-5-phenylpentanal was found to be a fragrance with a sweet-flowery, very complex scent of rose and with a slight waxy green note.
  • 2-Methyl-5-phenylpentanal is therefore extremely suitable for the development of perfumes with novel abstract fantasy scents with a rose note.
  • 2-methyl-5-phenylpentanol which is of course very structurally related to the compound 2-methyl-5-phenylpentanal, is a fragrance with a rose-like character, which is the general olfactory description in US Pat. No. 6,310,033 B1 equivalent. In this respect, the statements in US 6,310,033 B1 are thus confirmed.
  • the olfactory properties of 2-methyl-5-phenylpentanol go in the direction of the classic rose fragrances mentioned at the beginning; it is therefore mainly used when it comes to classic rose compositions with a long-lasting effect.
  • 2-methyl-5-phenylpentanal has a much greater intensity, radiation and elegance and is therefore particularly suitable for use in new modern fantasy rose notes.
  • 3-methyl-5-phenylpentanal which is also structurally very similar to the compound 2-methyl-5- ⁇ henylpentanal, has an odor profile that is very goes in the direction of citrus-like freshness. In this respect, too, the general olfactory evaluation from US 6,310,033 B1 is confirmed.
  • DE-OS 2 051 319 describes substituted alkanals of a general formula I, and it is stated in general that these should have a "fresh, flowery smell".
  • the substance falling under formula I becomes 2-methyl-5-phenylpentanal disclosed as a constituent of a mixture which also contains 2-ethyl-4- ⁇ henylbutanal (1-phenyl-3-formylpentane), which is described by an odor description relating to this mixture or even a description of the odor of 2-methyl-5-phenylpentanal itself
  • the term “flowery”, which refers to all alkanals of the formula I is merely to be understood as an indication of a very general odor direction.
  • 2-methyl-5-phenylpentanal is particularly suitable for modifying the rose smell of a fragrance composition which comprises at least one other fragrance with a rose smell. In this way, particularly sophisticated, modern perfume compositions can be created.
  • 2-methyl-5-phenylpentanal is advantageously used to produce a perfume with a rose scent; a corresponding procedure comprises the following steps:
  • the rose smell of the perfume is caused by 2-methyl-5- ⁇ henylpentanal if none of the other usual perfume ingredients present itself has a rose smell. If there are other perfume components with a rose scent, the 2-methyl-5-phenylpentanal contributes to the overall transmitted rose smell and therefore also determines it.
  • a method according to the invention for producing, amplifying or modifying a rose smell of a mixture comprises the following steps:
  • the other constituents can in turn be perfume constituents, but constituents that are usually not present in a perfume can also be present in the mixture.
  • Common other perfume ingredients with which 2-methyl-5-phenylpentanal can be advantageously combined, for example, can be found in S Arctander, Perfume and Flavor Materials, Vol I and II, Montclair, NJ, 1969, diverlag or K Bauer, D Garbe and H Surburg, Common Fragrance and Flavor Materials, 4rd Ed, Wiley-VCH, Weinheim 2001
  • Extracts from natural raw materials such as Ethe ⁇ sche oils, concretes, absolute,
  • Resme resinoids, balms, tinctures such as
  • fragrances from the group of hydrocarbons such as B. 3-carene; a-pinene; b-pinene; a-terpinene; G-
  • terpinene p-cymene; bisabolene; camphene; caryophyllene; cedrene; farnesene;
  • Nonadienol 3,7-dimethyl-7-methoxyoctane-2-ol; 9-decenol; 10-undecenol; 4
  • Methyl -3-decen-5-ol the aliphatic aldehydes and their acetals such as.
  • Tridecen yarnrenitril 3, tridecadienonitrile; 3,7-dimethyl-2,6-octadienonitrile; 3,7-dimethyl-6-octen Acid Citril; the ester of aliphatic carboxylic acids such as (E) - and (Z) -3-hexenyl formate; ethylacetoacetate; isoamyl; hexyl acetate; 3,5,5-trimethylhexyl acetate; 3-methyl-2-butenyl acetate; (E) -2-hexenyl acetate; (E) - and (Z) -3-hexenyl acetate; octyl acetate; 3-octyl acetate; 1-octen-3-yl acetate; ethyl butyrate; Butyl butyrate,; isoamyl; hexyl butyrate; (E) - and (Z) -3-hexen
  • Citronellol Citronellol; geraniol; nerol; linalool; Lavadulol; nerolidol; farnesol; tetrahydrolinalool; tetrahydrogeraniol; 2,6-dimethyl-7-octen-2-ol; 2,6-dimethyl octane-2-ol; 2-methyl-6-methylene-7-octen-2-ol; 2,6-dimethyl-5,7-octadiene-2-oI; 2,6-dimethyl-3,5-octadiene-2-ol; 3,7-dimethyl-4,6-octadien-3-ol; 3,7-dimethyl-1,5,7-octatrien-3-ol 2,6-dimethyl-2,5,7-octatrien-1-ol; as well as their formates, acetates, propionates, isobutyrates, butylates, isovalerianates, pen
  • menthol isopulegol; alpha-terpineol; Terpinenol-4; Menthane-8-ol; Menthane-1-ol; Menthane-7-ol; borneol; Isobomeol; linalool; monopoly; cedrol; ambrinol; Vetyverol; guaiol; as well as their formates, acetates, propionates, isobutyrates, butyrates, isovalerianates, pentanoates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoate; the cyclic terpene aldehydes and ketones such.
  • cyclic and macrocyclic ketones such as 4-tert-butylcyclohexanone; 2,2,5-trimethyl-5-pentylcyclopentanone; 2-heptylcyclopentanone; 2-pentylcyclopentanone; 2-hydroxy-3-methyl-2-cyclopenten-1-one; 3-methyl-cis-2-penten-1-yl-2-cyclopenten-1-one; 3-methyl-2-pentyl-2-cyclopenten-1-one; 3-methyl-4-cyclopentadecenone; 3-methyl-5-cyclopentadecenone; 3-methylcyclopentadecanone; 4- (1-ethoxyvinyl) -3,3,5,5-tetramethylcyclohexanone; 4-tert-pentylcyclohexanone; 5-CycIohexadecen-1-one; 6,7-dihydro-1,1,3,3-pentamethyl-4 (5H) -indanone; 8-cyclohe
  • cinnamyl 2-Phenoxyethylisob ⁇ tyrat; 4-methoxybenzyl acetate; the araliphatic ether such as e.g. 2-phenylethyl; 2-phenylethyl isoamyl ether; 2-phenylethyl-1-ethoxyethyl ether; Phenylacetaldehyde dimethyl acetal; phenylacetaldehyde; Hydratropaaldehyddimethylacetal;
  • Phenylacetaldehydglycerinacetal 2,4,6-trimethyl-4-phenyl-1,3-dioxane
  • acetophenone 4-methyl acetophenone; 4-methoxyacetophenone; 4-tert-butyl-2,6-dimethylacetophenone; 4-phenyl-2-butanone; 4- (4-hydroxyphenyl) -2-butanone; 1 - (2-naphthalenyl) ethanone; 2-benzofuranylethanone; (3-methyl-2-benzofuranyl) ethanone;
  • benzoic acid phenylacetic acid; methylbenzoate; ethyl benzoate; hexyl benzoate;
  • Benzyl benzoate methyl phenylacetate; ethyl phenylacetate; geranyl phenylacetate; Phenylethyl phenylacetate; Methylcinnmat; ethylcinnamate; Benzyl;
  • the invention also relates to personal care products with a scent of roses, which may in particular be those selected from the group of products consisting of solid and liquid soaps, shower gels, shampoos, shaving soaps, shaving foams, bath additives, cosmetic oil-in emulsions -Water-, of the water-in-oil and of the water-in-oil-in-water type such as skin creams and lotions, face creams and lotions
  • sunscreen creams and lotions such as eyeshadows, nail polishes, make-ups, lipsticks and maseara exist.
  • the personal care products according to the invention comprise 2-methyl-5-phenylpentanal and usual constituents of a personal care product such as carrier materials, abrasive agents, astringents, moisturizing substances, antibacterial agents, anti-acne agents, anti-cellulite agents, anti-microbial agents, anti-oxidants, anti-perspirants, anti-dandruff agents , antiseptic agents, binders, bleaching agents, chelating agents, creams, deodorising agents, mono- or polyunsaturated fatty acids, emulsifiers, depilatory agents, anti-inflammatory agents, color-protecting agents, dyes, fats, moisturizing substances, moisturizers, moisturizing agents, film-forming agents, gelling agents, gelling agents, saturated fatty acids, skin lightening agents, skin soothing agents, skin tanning agents, skin softening agents, skin healing agents, skin cooling agents, skin care agents, skin cleansing agents, skin protecting agents, skin warming agents, ir anti-irritants, anti-
  • the amount of 2-methyl-5-phenylpentanal in a personal care product according to the invention is such that it has the smell of rose due to the presence of the 2-methyl-5-phenylpenta ⁇ al (a) or (b) in comparison with a composition of said usual components of a personal care product has a modified scent of rose, depending on whether one or more of the other components of the personal care product itself have a rose scent or not.
  • the invention also relates to fragrance mixtures with a scent of rose, which comprise a sensorially effective amount of 2-methyl-5-phenylpentanal, sensorially effective amounts of at least two further fragrance substances and optionally other conventional constituents such as solvents or the like. At least one of the other fragrance substances will have a rose scent in a large number of cases, in particular if a fragrance mixture with a unusual rose smell is desired.
  • the amount of 2-methyl-5-phenylpentanal used can be 0.1 to 90% by weight, a range from 0.5 to 50% by weight is preferred, and a range from 1 to 25% by weight is particularly preferred .-%, based on the total mass of the fragrance mixture.
  • Fragrance mixtures containing 2-methyl-5-phenylpentanal are advantageously used for perfuming in liquid form, undiluted or diluted with a solvent.
  • 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 etc.
  • the invention also relates to perfumed products, a fragrance mixture according to the invention and a carrier or a substrate include that is in direct contact with this fragrance mixture.
  • perfumed products can be, for example, an alcoholic perfume, a personal care product or a household cleaning or care product or the like.
  • Alcoholic perfumes which contain a fragrance mixture according to the invention with a rose scent can, for example, be selected from the group of the products perfume extracts, eau de perfumes, eau de toilettes, aftershaves, eau de colognes, pre-shave products and splash colognes.
  • Personal care products which contain a fragrance mixture according to the invention with a rose scent can, for example, be selected from the group of personal care products already mentioned above.
  • Household cleaning or care products that contain a fragrance mixture according to the invention with a rose scent can, for example, be selected from the following group: acidic, alkaline and neutral cleaning agents, such as e.g. Floor cleaners, window glass cleaners, dishwashing detergents, bathroom and sanitary cleaners, scouring milk, solid and liquid toilet cleaners, powder and foam-shaped carpet cleaners, textile fresheners, ironing aids, liquid detergents, powder detergents, laundry pretreatment agents such as bleach, soaking agents and stain removers, fabric softener, laundry soap, laundry soap Disinfectants, surface disinfectants and air fresheners in liquid, gel-like or solid form, aerosol sprays, incense sticks, candles, lamp oils, and waxes and polishes such as furniture polishes, floor waxes and shoe creams.
  • acidic, alkaline and neutral cleaning agents such as e.g.
  • floor cleaners such as e.g.
  • a perfumed product according to the invention is generally produced by adding (a) 2-methyl-5-phenylpentanal or (b) a fragrance mixture according to the invention (see above), optionally together with other perfume ingredients, to the product (to be perfumed), so that the resulting perfumed product due to the presence of 2- Methyl-5-phenylpentanal (a) has a rose odor or (b) in the presence of other perfume components with rose odor has a modified or intensified rose odor.
  • Fragrance mixtures according to the invention containing 2-methyl-5-phenylpentanal can be used in concentrated form, in solutions or in the following modified form:
  • Such carriers can be porous inorganic materials such as light sulfate, silica gels, zeolites, gypsum, clays, clay granules, gas concrete etc. or organic materials such as woods; Cellulose-based substances, sugar or plastics such as PVC, polyvinyl acetate or polyurethanes.
  • fragrance mixtures according to the invention microencapsulated, spray-dried, as an inclusion complex or as an extrusion product and to add them to the (preliminary) product to be perfumed.
  • modified perfume oils are in some cases further optimized by so-called “coating” with suitable materials with a view to a more targeted fragrance release, for which purpose wax-like plastics such as polyvinyl alcohol are preferably used.
  • the microencapsulation of the perfume oils can take place, for example, by means of the so-called coacervation process with the aid of capsule materials, for example made of polyurethane-like substances or soft gelatin.
  • the spray-dried perfume oils can be produced, for example, by spray drying an emulsion or dispersion containing the perfume oil, with modified starches, proteins, dextrin and vegetable as carrier substances Gums can be used.
  • Inclusion complexes can be prepared, for example, by adding dispersions of the perfume oil and cyclodextrins or urea derivatives in a suitable solvent, for example water.
  • Extrusion products can be made by fusing the perfume oils with a suitable wax-like substance and by extrusion with subsequent solidification, if necessary in a suitable solvent, for example isopropanol.
  • the invention also relates to a process for the preparation of 2-methyl-5-phenylpentanal.
  • the process according to the invention comprises the hydrogenation of 2-methyl-5-phenyl-2,4-pentadienal, for example by
  • Condensation of cinnamaldehyde with propionaldehyde can be obtained.
  • a method for producing 2-methyl-5-phenyl-2,4-pentadienal is e.g. described in DE 555490A. When using the method according to the invention, one reaction stage is saved and the production is 5 less expensive than when using 3-phenylpropanal as the starting material.
  • the hydrogenation of 2-methyl-5-phenyl-2,4-pentadienal to 2-methyl-5-phenylpentanal according to the invention is advantageously carried out using palladium as the hydrogenation catalyst.
  • the palladium can be applied to a carrier such as activated carbon or aluminum oxide.
  • the loading of the carrier with palladium is preferably in the range from 5 to 10% by weight.
  • the palladium catalyst can be used in the dry or wet state.
  • the weight ratio of the catalyst used to 2-methyl-5-phenyl-15 2,4-pentadienal can be between 0.00001: 1 and 0.01: 1, a ratio of 0.0001: 1 to 0.001: 1 is preferred.
  • the hydrogen pressure during the hydrogenation is advantageously 1 to 20 bar, preferably 1-5 bar.
  • the reaction temperature during the hydrogenation is advantageously 20 20 to 100 ° C, preferably 50-80 ° C.
  • the reaction time of the hydrogenation is advantageously 1 to 50 hours, preferably 6 to 15 hours.
  • fragrances are mixed in the stated amounts (parts by weight):
  • This starting composition is a perfume mole with a green, flowery chord with emphasized lily of the valley and rose notes.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne l'utilisation de 2-méthyle-5-phénylpentanal pour produire, modifier ou renforcer un arôme de rose.
EP04733350A 2003-05-27 2004-05-17 2-methyle-5-phenylpentanal utilise comme senteur de rose Withdrawn EP1631247A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE2003124018 DE10324018A1 (de) 2003-05-27 2003-05-27 2-Methyl-5-phenylpentanal als Rosenriechstoff
DE2003125628 DE10325628A1 (de) 2003-06-06 2003-06-06 2-Methyl-5-phenylpentanal als Rosenriechstoff
PCT/EP2004/050822 WO2004105724A1 (fr) 2003-05-27 2004-05-17 2-methyle-5-phenylpentanal utilise comme senteur de rose

Publications (1)

Publication Number Publication Date
EP1631247A1 true EP1631247A1 (fr) 2006-03-08

Family

ID=33491641

Family Applications (1)

Application Number Title Priority Date Filing Date
EP04733350A Withdrawn EP1631247A1 (fr) 2003-05-27 2004-05-17 2-methyle-5-phenylpentanal utilise comme senteur de rose

Country Status (3)

Country Link
US (1) US20070072789A1 (fr)
EP (1) EP1631247A1 (fr)
WO (1) WO2004105724A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6182235B2 (ja) * 2016-04-22 2017-08-16 花王株式会社 悪臭抑制剤

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3716730A1 (de) * 1987-05-19 1988-12-01 Basf Ag 4-methyl-4-phenyl-1-pentanale, deren herstellung und verwendung als riechstoffe
US4837201A (en) * 1988-05-17 1989-06-06 Basf Aktiengesellschaft 4-Methyl-4-phenyl-1-pentanals, their preparation and their use as scents
GB9006254D0 (en) * 1990-03-20 1990-05-16 Unilever Plc Perfumed products
GB9120951D0 (en) * 1991-10-02 1991-11-13 Unilever Plc Perfume particles
GB9821693D0 (en) * 1998-10-06 1998-12-02 Humphries Martyn Improvements in or relating to insect repellents
US6310033B1 (en) * 1999-12-28 2001-10-30 Bush Boake Allen Inc. Fragrance materials

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2004105724A1 *

Also Published As

Publication number Publication date
US20070072789A1 (en) 2007-03-29
WO2004105724A1 (fr) 2004-12-09

Similar Documents

Publication Publication Date Title
EP3197987B1 (fr) Utilisation de cis- ou trans-(2-isobutyl-4-méthyl-tétrahydropyrane-4-yl) acétate isomèrique pur ou très enrichi en isomères
DE102006043587A1 (de) 2-Methyl-2-alkenyl-substituierte 1,3-Dioxane als Riechstoffe
EP3206756A1 (fr) Utilisation d'hexadéca-8,15-diénal en tant que produit chimique aromatique
EP3002003A1 (fr) Utilisation de carbaldéhyde cyclique de nouveau type en tant qu'arôme
EP1682230A1 (fr) 4,8-dimethyl-7-nonen-2-one et 4,8-dimethylnonan-2-one en tant que substances odorantes
EP2848611B1 (fr) Octahydrobenzofurane et Octahydrochromene - Méthode de Préparation et Leur Utilisation Comme Parfums
EP2072083B1 (fr) Utilisation de 2,4'-diméthyl-propiophénone en tant que parfum
EP1747186B1 (fr) Composition parfumante comprenant de l'isobutyrate de 3-méthylbenzyle
DE10333379A1 (de) Acetale, ihre Verwendung als Reichstoffe und Verfahren zu ihrer Herstellung
DE10361524A1 (de) (Z)-7-Cyclohexadecen-1-on als Riechstoff
EP1599434B1 (fr) 4-cyclohexyl-2-butanol servant de parfum
DE102007055124A1 (de) 7-(3-Methylbut-2-en-1-yl)-2H-1,5-benzodioxepin-3(4H)-on als Riechstoff
EP1797025B1 (fr) 4-isoamylcyclohexanol comme substance odorante
DE102008000275A1 (de) Alkenacetale und ihre Verwendung als Riechstoffe
DE19931709A1 (de) Neue tetracyclische Acetale
EP1648526B1 (fr) Esters cis-3,3,5-trimethylcyclohexyliques
EP3853199B1 (fr) 2-(5-isopropyl-2-méthyl-cyclohex-2-én-1-yl-)acétaldéhyde et 2-(6-isopropyl-3-méthyl-cyclohex-2-én-1-yl-)acétaldéhyde en tant que nouveaux parfums
EP1631247A1 (fr) 2-methyle-5-phenylpentanal utilise comme senteur de rose
DE102005033642A1 (de) 4-Isomaylcyclohexanon als Riechstoff
EP1923389A1 (fr) 2-Isopropyl-5-méthyloxépane et son utilisation comme composé de fragrance
DE10229474A1 (de) Neue Riechstoffe und Verfahren zu ihrer Herstellung
DE10324018A1 (de) 2-Methyl-5-phenylpentanal als Rosenriechstoff
DE10325628A1 (de) 2-Methyl-5-phenylpentanal als Rosenriechstoff
DE102004046282A1 (de) (Z)-8-Cycloheptadecen-1-on als Riechstoff
DE10222025A1 (de) Neue ungesättigte makrocyclische Oxalactone

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20051227

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LI LU MC NL PL PT RO SE SI SK TR

DAX Request for extension of the european patent (deleted)
17Q First examination report despatched

Effective date: 20060330

GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

GRAC Information related to communication of intention to grant a patent modified

Free format text: ORIGINAL CODE: EPIDOSCIGR1

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20080429