EP0085352A2 - Unsaturated oximes, preparation thereof and use thereof as perfume and in the fragment compositions - Google Patents

Unsaturated oximes, preparation thereof and use thereof as perfume and in the fragment compositions Download PDF

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Publication number
EP0085352A2
EP0085352A2 EP83100415A EP83100415A EP0085352A2 EP 0085352 A2 EP0085352 A2 EP 0085352A2 EP 83100415 A EP83100415 A EP 83100415A EP 83100415 A EP83100415 A EP 83100415A EP 0085352 A2 EP0085352 A2 EP 0085352A2
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Prior art keywords
carbon atoms
oxime
compounds
hydrocarbon radical
nonen
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Granted
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EP83100415A
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German (de)
French (fr)
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EP0085352A3 (en
EP0085352B1 (en
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Paul Albert Dr. Ochsner
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Givaudan SA
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L Givaudan and Co SA
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    • 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
    • C11B9/0007—Aliphatic compounds

Definitions

  • the invention relates to new fragrances. These are the compounds of the formula wherein R is an olefinically monounsaturated hydrocarbon radical, the unsaturation being in the ⁇ , ⁇ position, and R 'is a saturated hydrocarbon radical having 1 to 4 carbon atoms, and the number of carbon atoms in R + R' is 10-13.
  • Formula I is intended to encompass the syn and anti forms of oxime I.
  • the anti form is preferred.
  • radicals R and R ' can be straight-chain or branched.
  • R and R ' preferably contain 10 to 12, particularly preferably 10 or 11 carbon atoms.
  • the invention further relates to a process for the preparation of the compounds I.
  • This method is characterized in that a compound of the formula wherein R and R 'have the above meanings, reacted with hydroxylamine or one of its salts.
  • the reaction of the compound of formula II with hydroxylamine or a salt thereof can be carried out according to methods known per se, see, for example, organic medicine, basic organic chemical internship, collective of authors; 7th edition; VEB German Publishing House of Sciences; Berlin 1967, 375:
  • the hydroxylamine is expediently left as a salt, for example as hydrochloride or sulfate in an alkaline solution containing pyridine or in an aqueous alkaline solution with the K etonII react; the reaction temperature is preferably the reflux temperature of the reaction mixture.
  • the oximes can be purified by distillation.
  • the starting ketones II are known or can be prepared by methods known per se, e.g. by chain extension of simple, commercially available ketones, for example using allyl halides.
  • the compounds I have special organoleptic properties which make them particularly suitable as fragrances.
  • the invention accordingly also relates to the use of the compounds I as fragrances.
  • the oximes according to the invention are distinguished by a special combination of perfume properties. They are all either colorless or at most weakly colored, easily accessible, the individual approaches are constant in smell, not irritating, stable and easy to use.
  • the compounds of the formula I are generally pronounced of notes of black currant, sage, ivy, grapefruit; Due to their natural smell and their retention time (long-term effect, especially regarding freshness) they are particularly suitable for the modification of known, e.g.
  • Smell black currant, natural, earthy, herbaceous.
  • Smell black currant, sage, lavender, grapefruit, leek.
  • Smell of fresh vegetables, of peas, daisies, dogwood shrubs, well adhering.
  • Smell of fresh vegetables, of ivy, dogwood shrub.
  • Smell of fresh vegetables, of tomato leaves, of black currants, very natural looking.
  • Smell of grapefruit, currants, well adhering.
  • Smell like yolk flowers, very natural.
  • the compounds of the formula I can be used within wide limits, which can range, for example, from 0.1 (detergents) to 50% (alcoholic solutions) in compositions, without these values being intended to represent limit values, however, since the experienced perfumer can use even lower ones Concentrations can achieve effects or can build up new types of complexes with even higher doses.
  • the preferred concentrations are between 0.5 and 25%.
  • the compositions produced with I can be used for all types of perfumed consumer goods (Eaux de Cologne, Eaux de Toilette, extras, lotions, creams, shampoos, soaps, ointments, powders, deodorants, detergents, tobacco, etc.).
  • the compounds I can be used in the production of compositions and - as the composition above shows - using a wide range of known odoriferous substances.
  • the known fragrances listed above can be used in a manner known to the perfumer, e.g. from W.A. Poucher, Perfumes, Cosmetics and Soaps 2, 7th edition, Chapman and Hall, London 1974.
  • Perfumery base generally floral

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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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Tea And Coffee (AREA)
  • Manufacture Of Tobacco Products (AREA)
  • Detergent Compositions (AREA)

Abstract

Die Erfindung betrifft neue Riechstoffe, und zwar neue Oxime <IMAGE> worin R ein olefinisch einfach ungesättigter Kohlenwasserstoffrest ist, wobei die Ungesättigtheit sich in γ, δ-Stellung befindet, und R' ein gesättigter Kohlenwasserstoffrest mit 1 bis 4 Kohlenstoffatomen ist, und wobei die Anzahl Kohlenstoffatome von R + R' 10-13 beträgt. Die Erfindung betrifft auch ein Verfahren zur Herstellung der neuen Oxime I. Die Erfindung betrifft auch die Verwendung von I als Riechstoffe und Riechstoffkompositionen, die durch einen Gehalt an Verbindungen I gekennzeichnet sind.The invention relates to new fragrances, namely new oximes <IMAGE> wherein R is an olefinically monounsaturated hydrocarbon radical, the unsaturation being in the γ, δ position, and R 'is a saturated hydrocarbon radical having 1 to 4 carbon atoms, and wherein the Number of carbon atoms of R + R 'is 10-13. The invention also relates to a process for the preparation of the new oximes I. The invention also relates to the use of I as fragrances and fragrance compositions which are characterized by a content of compounds I.

Description

Die Erfindung betrifft neue Riechstoffe. Es handelt sich dabei um die Verbindungen der Formel

Figure imgb0001
worin R ein olefinisch einfach ungesättigter Kohlenwasserstoffrest ist, wobei die Ungesättigtheit sich in γ,δ-Stellung befindet, und R' ein gesättigter Kohlenwasserstoffrest mit 1 bis 4 Kohlenstoffatomen ist, und wobei die Anzahl Kohlenstoffatome von R+R' 10-13 beträgt.The invention relates to new fragrances. These are the compounds of the formula
Figure imgb0001
 wherein R is an olefinically monounsaturated hydrocarbon radical, the unsaturation being in the γ, δ position, and R 'is a saturated hydrocarbon radical having 1 to 4 carbon atoms, and the number of carbon atoms in R + R' is 10-13.

Die Formel I soll die syn- und die anti-Formen der Oxime I umfassen. Die anti-Form ist bevorzugt.Formula I is intended to encompass the syn and anti forms of oxime I. The anti form is preferred.

Die Reste R und R' können geradkettig oder verzweigt sein.The radicals R and R 'can be straight-chain or branched.

R und R' enthalten vorzugsweise 10 - 12, speziell bevorzugt 10 oder 11 C-Atome. R and R 'preferably contain 10 to 12, particularly preferably 10 or 11 carbon atoms.

Die Erfindung betrifft ferner ein Verfahren zur Herstellung der Verbindungen I.The invention further relates to a process for the preparation of the compounds I.

Dieses Verfahren ist dadurch gekennzeichnet, dass man eine Verbindung der Formel

Figure imgb0002
worin R und R' obige Bedeutungen besitzen, mit Hydroxylamin bzw. einem seiner Salze umsetzt.This method is characterized in that a compound of the formula
Figure imgb0002
 wherein R and R 'have the above meanings, reacted with hydroxylamine or one of its salts.

Die Umsetzung der Verbindung der Formel II mit Hydroxylamin bzw. einem Salz davon kann nach an sich bekannten Methoden durchgeführt werden, siehe z.B. Organikum, Organisch-chemisches Grundpraktikum, Autorenkollektiv; 7. Auflage; VEB Deutscher Verlag der Wissenschaften; Berlin 1967, 375: Man lässt das Hydroxylamin zweckmässigerweisealsSalz, z.B. als Hydrochlorid oder Sulfat in pyridinenthaltender alkalischer Dösung bzw. in wässrig-alkalischer Lösung mit dem KetonII reagieren; die Reaktionstemperatur ist dabei vorzugsweise die Rückflusstemperatur des Reaktionsgemisches.The reaction of the compound of formula II with hydroxylamine or a salt thereof can be carried out according to methods known per se, see, for example, organic medicine, basic organic chemical internship, collective of authors; 7th edition; VEB German Publishing House of Sciences; Berlin 1967, 375: The hydroxylamine is expediently left as a salt, for example as hydrochloride or sulfate in an alkaline solution containing pyridine or in an aqueous alkaline solution with the K etonII react; the reaction temperature is preferably the reflux temperature of the reaction mixture.

Die Oxime können durch Destillation gereinigt werden.The oximes can be purified by distillation.

Die Ausgangsketone II sind bekannt oder können nach an sich bekannten Methoden hergestellt werden, z.B. durch Kettenverlängerung einfacher, handelsüblicher Ketone, beispielsweise mittels Allylhalogeniden.The starting ketones II are known or can be prepared by methods known per se, e.g. by chain extension of simple, commercially available ketones, for example using allyl halides.

Die Verbindungen I weisen besondere organoleptische Eigenschaften auf, auf Grund derer sie sich vorzüglich als Riechstoffe eignen.The compounds I have special organoleptic properties which make them particularly suitable as fragrances.

Die Erfindung betrifft demgemäss auch die Verwendung der Verbindungen I als Riechstoffe.The invention accordingly also relates to the use of the compounds I as fragrances.

Die erfindungsgemässen Oxime zeichnen sich durch eine besondere Kombination von parfümistisch wertvollen Eigenschaften aus. Sie sind alle entweder farblos oder höchstens schwach gefärbt, leicht zugänglich, die einzelnen Ansätze sind konstant im Geruch, nicht irritierend, stabil und bequem in der Handhabung.The oximes according to the invention are distinguished by a special combination of perfume properties. They are all either colorless or at most weakly colored, easily accessible, the individual approaches are constant in smell, not irritating, stable and easy to use.

Die Verbindungen der Formel I erinnern geruchlich im allgemeinen an Noten von schwarzen Johannisbeeren,Salbei,-Efeu, Grapefruit; sie eignen sich aufgrund ihrer natürlilichen Geruchsnoten und ihrer Haftdauer (Langzeiteffekt, insbesondere bezüglich Frische) insbesondere zur Modifizierung von bekannten, z.B.The compounds of the formula I are generally reminiscent of notes of black currant, sage, ivy, grapefruit; Due to their natural smell and their retention time (long-term effect, especially regarding freshness) they are particularly suitable for the modification of known, e.g.

  • a) blumigen Kompositionen, in denen z.B. die Citrusnoten verstärkt zum Ausdruck kommen sollen (z.B. für Cologne-Typen u.ä., Extraits),a) floral compositions in which e.g. the citrus notes should be increasingly expressed (e.g. for cologne types, etc., extraits),
  • b) des weiteren aber auch von fruchtigen Kompositionen,z.B. vom Typ Johannisbeere (Extrait-Typen) ,Kompositionen der femininen wie der männlichen Richtung , vonb) but also of fruity compositions, for example of the currant type (extrait types), compositions of the femini like the male direction, from
  • c) Kompositionen mit grünen Noten, wo insbesondere ein erwünschter natürlicher Effekt erzielt wird, und schliesslich vonc) compositions with green notes, where in particular a desired natural effect is achieved, and finally by
  • d) Kompositionen, in denen generell der Charakter von natürlichen Oelen angestrebt wird, z.B. Flieder oder Lavendel.d) compositions in which the character of natural oils is generally sought, e.g. Lilac or lavender.

Besonders interessante Verbindungen sind:Particularly interesting connections are:

5-Aethyl-7-nonen-4-on-oxim5-ethyl-7-nonen-4-one oxime

Geruch: nach schwarzen Johannisbeeren, wirkt natürlich, erdig, krautig.Smell: black currant, natural, earthy, herbaceous.

2,4,4,7-Tetramethyl-6-octen-3-on-oxim2,4,4,7-tetramethyl-6-octen-3-one oxime

Geruch: nach schwarzen Johannisbeeren, Salbei, Lavendel, Grapefruit, lauchartig.Smell: black currant, sage, lavender, grapefruit, leek.

4,7-Dimethyl-6-nonen-3-on-oxim4,7-dimethyl-6-nonen-3-one oxime

Geruch: nach frischem Gemüse, nach Erbsen, Gänseblümchen, Hartriegelstrauch, gut haftend.Smell: of fresh vegetables, of peas, daisies, dogwood shrubs, well adhering.

3-Aethyl-6-methyl-5-octen-2-on-oxim3-ethyl-6-methyl-5-octen-2-one oxime

Geruch: nach frischem Gemüse, nach Efeu, Hartriegelstrauch.Smell: of fresh vegetables, of ivy, dogwood shrub.

Weitere Beispiele von Verbindungen I sind:Further examples of compounds I are:

2,4,4,6-Tetramethyl-6-hepten-3-on-oxim2,4,4,6-tetramethyl-6-hepten-3-one oxime

Geruch: nach frischem Gemüse, nach Tomatenblättern, nach schwarzen Johannisbeeren, sehr natürlich wirkend.Smell: of fresh vegetables, of tomato leaves, of black currants, very natural looking.

3,3,6-Trimethyl-5-octen-2-on-oxim3,3,6-trimethyl-5-octen-2-one oxime

Geruch: nach Grapefruit, Johannisbeeren, gut haftend.Smell: of grapefruit, currants, well adhering.

2,2,7-Trimethyl-6-nonen-3-on-oxim2,2,7-trimethyl-6-nonen-3-one oxime

Geruch: nach Dotterblumen, sehr natürlich wirkend.Smell: like yolk flowers, very natural.

Die Verbindungen I verbinden sich mit zahlreichen bekannten Riechstoffingredienzien natürlichen oder synthetischen Ursprungs, wobei die Palette der natürlichen Rohstoffe sowohl leicht - als auch mittel - und schwerflüchtige Komponenten, und diejenige der Synthetika Vertreter aus praktisch allen Stoffklassen umfassen kann, wie dies aus der folgenden Zusammenstellung ersichtlich ist:

  • - Naturprodukte, wie Angelikasamenöl, Baummoos-Absolue, Basilikumöl, Beifussöl, Bergamotteöl, Castoreum, acetyliertes Cedernholzöl(z.B.Vertofix® IFF bzw. Cedartone® Givaudan), Corianderöl, Eichenmoos, Elemiöl, Galbanumöl, Geraniumöl, Jasmin Absolue und seine Substitute, Kamillenöl, Lavandinöl, Lavendelöl, Mandarinenöl, Mastix Absolue, Nelkenknospenöl, Neroliöl, Patchouliöl, Petitgrainöl Paraguay, Rosenöl, Rosmarinöl, Sandalholzöl, Styrax, Vetiveröl, Wermutöl, Ylang-Ylang-Oel, Ysopoel, Zibetöl, Zitronenöl.
  • Alkohole, wie Citronellol, Dimethylbenzylcarbinol, Dime- tol®Giv. (2,6-Dimethyl-2-heptanol), Geraniol,Linalool, Menthol 3-Methyl-5-(2',2',3'-trimethyl-cyclopent-3'-en-1'-yl)-pentan-2-ol(Sandalore® Givaudan), Nerol, Phenyl- äthylalkohol, Phenylpropylalkohol, natürliches Rhodinol, Terpineol, a-Terpineol, 2,2,8-Trimethyl-7-nonen-3-ol, Zimtalkohol.
  • - Aldehyde, wie a-Amylzimtaldehyd, Citral, Cyclamenaldehyd, Decanal, 3,5-Dimethyl-cyclohex-3-en-carboxaldehyd, n-Dodecanal, Heliotropin, a-Hexylzimtaldehyd, Hydroxycitro - nellal, Methylnonylacetaldehyd, p-tert.Butyl-a-methyl-di- hydro-zimt-aldehyd(z.B. Lilial®Givaudan), n-Undecen-lO-al.
  • - Ketone, wie Acetylcedren, Allyljonon, p-Hydroxybenzylaceton, a-Jonon, 2,4,4,7-Tetramethyl-6,8- nonadien-3-on , p-Methylacetophenon, Methyljonon, 1,2,3,4-Tetrahydro-1,1-dimethyl-4-propionyl- naphthalin .
  • - Ester, wie Aethylacetoacetat, 3-Aethyl-1,1-dimethyl-cy- clohex-3-en-2-carbonsäure-äthylester (Givescone® Givaudan), 3-Aethyl-1,1,4-trimethyl-cyclohexen-3-en-2-carbonsäure- äthylester (Myrascone® Givaudan), Allylphenoxyacetat, Amylsalicylat, Benzylacetat, Benzylsalicylat, Bornylacetat Cedrylacetat, Cinnamylformiat, cis-3-Hexenylacetat, cis-3-Hexenylbenzoat, Geranylacetat, Hexylsalicylat, Isobutylsalicyclat, Linalylacetat, Linalylanthranilat, Methyldihydrojasmonat, 4-[4-Methyl-3-pentenyl]-cyclohex-3-en-l-yl-carbinylacetat(z.B. Myraldylacetat® Givaudan), Oxyoctalinformiat Giv. (Δ1-1,5,9,10-Tetramethyl-5-formoxy-octa- lin), Phenyläthylacetat, Styrallylacetat, Terpenylacetat, p-tert. Butylcyclohexylacetat.
  • - Lactone, wie Cumarin, y-Decalacton, γ-Dodecalacton, γ-Nonalacton, y-Undecalacton.
  • - verschiedene weitere, in der Parfümerie oft benützten Komponenten, wie Acetaldehyd-propylphenyl-äthylacetal, Cyclocitrylidenacetonitril, 1,1-Dimethyl-4-acetyl-6-tert. butylindan, Dodecahydro-3a,6-6-9a-tetramethyl(2,1-b)furan, Eugenol, Galaxolid IFF (7-Acetyl-1,1,3,4,4,6-hexamethyl- tetralin), Indol, Isobutylchinolin, p-Menthan-8-thiol-3- on, Methyleugenol, Methyl-l-methyl-cyclododecyläther(z.B. Madrox® Givaudan), Moschus-Verbindungen(Ketonmoschus, 12-Oxahexadecanolid(z.B. Musk 174® Naarden), 8 ,12-0xido-13-14,15,16-tetranorlabdan(Fixateur 404®).
The compounds I combine with numerous known fragrance ingredients of natural or synthetic origin, the range of natural raw materials comprising both lightly, medium and low-volatility components, and that of synthetics can include representatives from practically all classes of substances, as can be seen from the following compilation is:
  • - Natural products, such as angelica seed oil, tree moss absolute, basil oil, mugwort oil, bergamot oil, castoreum, acetylated cedarwood oil (e.g. Vertofix® IFF or Cedartone® Givaudan), coriander oil, oak moss, elemi oil, galbanum oil, geranium oil, jasmine absolute and its substitutes, camomile oil , Lavender oil, mandarin oil, mastic absolute, clove bud oil, neroli oil, patchouli oil, petitgrain oil Paraguay, rose oil, rosemary oil, sandalwood oil, styrax, vetiver oil, wormwood oil, ylang-ylang oil, hyssopoel, civet oil, lemon oil.
  • Alcohols such as citronellol, dimethylbenzylcarbinol, Dime - tol®Giv. (2,6-dimethyl-2-heptanol), geraniol, linalool, menthol 3-methyl-5- (2 ', 2', 3'-trimethyl-cyclopent-3'-en-1'-yl) pentane 2-ol (Sandalore® Givaudan), nerol, phenyl ethyl alcohol, phenyl propyl alcohol, natural rhodinol, terpineol, a-terpineol, 2,2,8-trimethyl-7-nonen-3-ol, cinnamon alcohol.
  • - aldehydes, such as a-amylcinnamaldehyde, citral, cyclamenaldehyde, decanal, 3,5-dimethyl-cyclohex-3-ene-carboxaldehyde, n-dodecanal, heliotropin, a-hexylcinnamaldehyde, hydroxycitro - nellal, methylnonylacetaldehyde, p-tert-butyl-a-methyl-di-hydro-cinnamon aldehyde (e.g. Lilial®Givaudan), n-undecene-10-al.
  • - Ketones such as acetylcedrene, allyl ionone, p-hydroxybenzyl acetone, a-ionone, 2,4,4,7-tetramethyl-6,8-nonadien-3-one, p-methylacetophenone, methyl ionone, 1,2,3,4- Tetrahydro-1,1-dimethyl-4-propionylnaphthalene.
  • - Esters, such as ethyl acetoacetate, 3-ethyl-1,1-dimethyl-cyclohex-3-en-2-carboxylic acid ethyl ester (Givescone® Givaudan), 3-ethyl-1,1,4-trimethyl-cyclohexene-3 -en-2-carboxylic acid ethyl ester (Myrascone® Givaudan), allylphenoxyacetate, amyl salicylate, benzyl acetate, benzyl salicylate, bornyl acetate cedrylacetate, cinnamyl formate, cis-3-hexenyl acetate, cis-3-hexenylbenzylate, isanyl acetate, lylanyl acetate, geranyl acetate, lanyl acetate, geranyl acetate, , 4- [4-methyl-3-pentenyl] cyclohex-3-en-1-yl-carbinyl acetate (e.g. Myraldylacetat® Givaudan), oxyoctaline formate Giv. (Δ 1 -1,5,9,10-tetramethyl-5-formoxy-octa-lin), phenylethyl acetate, styrallyl acetate, terpenyl acetate, p-tert. Butylcyclohexyl acetate.
  • Lactones, such as coumarin, y-decalactone, γ-dodecalactone, γ-nonalactone, y-undecalactone.
  • - Various other components often used in perfumery, such as acetaldehyde propylphenyl ethylacetal, cyclocitrylidene acetonitrile, 1,1-dimethyl-4-acetyl-6-tert. butylindane, dodecahydro-3a, 6-6-9a-tetramethyl (2,1-b) furan, eugenol, galaxolide IFF (7-acetyl-1,1,3,4,4,6-hexamethyltetralin), indole, Isobutylquinoline, p-menthan-8-thiol-3-one, methyleugenol, methyl-l-methyl-cyclododecyl ether (e.g. Madrox® Givaudan), musk compounds (ketone musk, 12-oxahexadecanolide (e.g. Musk 174® Naarden), 8, 12 -Xxido-13-14,15,16-tetranorlabdan (Fixateur 404®).

Die Verbindungen der Formel I lassen sich in weiten Grenzen einsetzen, die beispielsweise von 0,1(Detergentien) - 50% (alkoholische Lösungen) in Kompositionen reichen können, ohne dass diese Werte jedoch Grenzwerte darstellen sollen, da der erfahrene Parfümeur auch mit noch geringeren Konzentrationen Effekte erzielen oder aber mit noch höheren Dosierungen neuartige Komplexe aufbauen kann. Die bevorzugten Konzentrationen bewegen sich zwischen 0,5 und 25%. Die mit I hergestellten Kompositionen lassen sich für alle Arten von parfümierten Verbrauchsgütern einsetzen (Eaux de Cologne, Eaux de Toilette, Extraits, Lotionen, Cremes, Shampoos, Seifen, Salben, Puder, Desodorantien, Detergentien, Tabak, etc.).The compounds of the formula I can be used within wide limits, which can range, for example, from 0.1 (detergents) to 50% (alcoholic solutions) in compositions, without these values being intended to represent limit values, however, since the experienced perfumer can use even lower ones Concentrations can achieve effects or can build up new types of complexes with even higher doses. The preferred concentrations are between 0.5 and 25%. The compositions produced with I can be used for all types of perfumed consumer goods (Eaux de Cologne, Eaux de Toilette, extras, lotions, creams, shampoos, soaps, ointments, powders, deodorants, detergents, tobacco, etc.).

Die Verbindungen I können demgemäss bei der Herstel - lung von Kompositionen und - wie obige Zusammenstellung zeigt - unter Verwendung einer breiten Palette bekannter Riechstoffe, verwendet werden. Bei der Herstellung solcher Kompositionen können die oben aufgeführten bekannten Riechstoffe nach (dem Parfümeur bekannter)Art und Weise verwendet werden, wie z.B. aus W.A. Poucher, Perfumes, Cosmetics and Soaps 2, 7. Auflage, Chapman und Hall, London 1974 hervorgehend.Accordingly, the compounds I can be used in the production of compositions and - as the composition above shows - using a wide range of known odoriferous substances. In the preparation of such compositions, the known fragrances listed above can be used in a manner known to the perfumer, e.g. from W.A. Poucher, Perfumes, Cosmetics and Soaps 2, 7th edition, Chapman and Hall, London 1974.

Beispiel 1example 1

In einem mit Rührer, Thermometer und Kühler versehenen Rundkolben löst man 14,8 g Hydroxylaminsulfat in 30 ml Wasser. Währenddem man 29 g 33% ige Natronlauge zugibt, hält man durch Kühlen die Temperatur bei 25°C. Dann tropft man langsam bei Zimmertemperatur eine Lösung von 27 g 5- Aethyl-7-nonen-4-on(Siedepunkt: 74°C/5mmHg;

Figure imgb0003
= 1,4407) in 50 ml Aethanol zu. Hierauf wird eine Stunde bei Rückflusstemperatur gehalten. Nach dem Abkühlen wird auf Eiswasser gegossen, in Aether aufgenommen und neutral gewaschen. Das Lösungsmittel wird abdestilliert und man erhält 26,8 g rohes Oxim, welche fraktioniert destilliert werden.14.8 g of hydroxylamine sulfate are dissolved in 30 ml of water in a round-bottomed flask equipped with a stirrer, thermometer and cooler. While adding 29 g of 33% sodium hydroxide solution, the temperature is kept at 25 ° C. by cooling. Then slowly added dropwise at room temperature a solution of 27 g of 5- A ethyl-7-nonene-4-one (boiling point: 74 ° C / 5mmHg;
Figure imgb0003
 = 1.4407) in 50 ml of ethanol. This is held at the reflux temperature for one hour. After cooling, it is poured onto ice water, taken up in ether and washed neutral. The solvent is distilled off and 26.8 g of crude oxime are obtained, which are fractionally distilled.

Siedepunkt des reinen 5-Aethyl-7-nonen-4-on-oxims (10,5 g): 118°C/5 mmHg ;

Figure imgb0004
= 1,4691.Boiling point of pure 5-ethyl-7-nonen-4-one oxime (10.5 g): 118 ° C / 5 mmHg;
Figure imgb0004
 = 1.4691.

Auf analoge Weise werden erhalten:

  • - aus 41,7 g 4,7-Dimethyl-6-nonen-3-on(Siedepunkt 75°C/6 mmHg;
    Figure imgb0005
    = 1,4472) und 20,5 g Hydroxylaminsulfat 29,1 g 4,7-Dimethyl-6-nonen-3-on-oxim; Siedepunkt 85°C/0,5 mmHg;
    Figure imgb0006
     = 1,4762.
  • - aus 25,5 g 3,3,6-Trimethyl-5-octen-2-on (Siedepunkt 75°C/6mmHg;
    Figure imgb0007
    = 1,4500) und 13,2 g Hydroxylaminsulfat 8 g 3,3,6-Trimethyl-5-octen-2-on-oxim; Siedepunkt 70°/0,15 mmHg;
    Figure imgb0008
    = 1,4790.
  • - aus 32,6 g 2,2,7-Trimethyl-6-nonen-3-on (Siedepunkt 88°C/5mmHg; 1,4448) und 14,8 g Hydroxylaminsulfat 1,1 g 2,2,7-Trimethyl-6-nonen-3-on-oxim; Siedepunkt 86-87°C/0,45 mmHg;
    Figure imgb0009
    = 1,4715.
The following are obtained in an analogous manner:
  • - from 41.7 g of 4,7-dimethyl-6-nonen-3-one (boiling point 75 ° C / 6 mmHg;
    Figure imgb0005
     = 1.4472) and 20.5 g hydroxylamine sulfate 29.1 g 4,7-dimethyl-6-nonen-3-one oxime; Boiling point 85 ° C / 0.5 mmHg;
    Figure imgb0006
     = 1.4762.
  • - from 25.5 g of 3,3,6-trimethyl-5-octen-2-one (boiling point 75 ° C / 6mmHg;
    Figure imgb0007
     = 1.4500) and 13.2 g hydroxylamine sulfate 8 g 3,3,6-trimethyl-5-octen-2-one oxime; Boiling point 70 ° / 0.15 mmHg;
    Figure imgb0008
     = 1.4790.
  • - from 32.6 g of 2,2,7-trimethyl-6-nonen-3-one (boiling point 88 ° C / 5mmHg; 1.4448) and 14.8 g of hydroxylamine sulfate 1.1 g of 2,2,7-trimethyl -6-nonen-3-one oxime; Boiling point 86-87 ° C / 0.45 mmHg;
    Figure imgb0009
     = 1.4715.

Beispiel 2Example 2

In einem mit Rührer, Thermometer und Kühler versehenen Rundkolben wird eine Lösung von 20 g Hydroxylaminchlorhydrat und 20 g Pyridin in 200 ml Aethanol während einer Stunde bei Rückflusstemperatur gehalten. Hierauf werden 20 g 2,4,4, 7-Tetramethyl-6-octen-3-on (Siedepunkt 76°C/5mmHg ;

Figure imgb0010
= 1,4469) zugegeben , und das Reaktionsgemisch wird während weiteren 3 Stunden bei Rückflusstemperatur gehalten. Hierauf wird der grösste Teil des Aethanols abdestilliert. Nach dem Abkühlen wird auf Eiswasser gegossen und in Aether aufgenommen. Die Aetherlösung wird zuerst mit Wasser, dann mit 5% iger Salzsäure zwecks Eliminierung des Pyridinüberschusses, dann wieder mit Wasser bis zum Neutralpunkt gewaschen. Nach dem Abdampfen des Aethers erhält man 18 g Rohprodukt. Durch Destillieren gewinnt man 15,3 g Ausgangsketon zurück. Der Rückstand (1,2 g) besteht aus 2,4,4,7-Tetramethyl-6-octen-3-on-oxim,
Figure imgb0011
 = 1,4770.A solution of 20 g of hydroxylamine chlorohydrate and 20 g of pyridine in 200 ml of ethanol is kept for one hour at reflux temperature in a round-bottomed flask equipped with a stirrer, thermometer and cooler. Then 20 g of 2,4,4, 7-tetramethyl-6-octen-3-one (boiling point 76 ° C / 5mmHg;
Figure imgb0010
 = 1.4469), and the reaction mixture is kept at the reflux temperature for a further 3 hours. Most of the ethanol is then distilled off. After cooling, it is poured onto ice water and taken up in ether. The ether solution is washed first with water, then with 5% hydrochloric acid to eliminate the excess pyridine, then again with water to the neutral point. After the ether has been evaporated off, 18 g of crude product are obtained. 15.3 g of starting ketone are recovered by distillation. The residue (1.2 g) consists of 2,4,4,7-tetramethyl-6-octen-3-one oxime,
Figure imgb0011
 = 1.4770.

Auf analoge Weise werden erhalten:

  • - aus 30 g 3-Aethyl-6-methyl-5-octen-2-on(Sdp. 77°C/ 6 mmHg;
    Figure imgb0012
     = 1,4476),30 g Hydroxylaminchlorhydrat und 30 g Pyridin 12,8 g 3-Aethyl-6-methyl-5-octen-2-on-oxim; Sdp. 77°C/0,2 mmHg;
    Figure imgb0013
    = 1,4750.
  • - aus 34 g 2,4,4,6-Tetramethyl-6-hepten-3-on(Sdp. 62oC/5 mmHg;
    Figure imgb0014
     = 1,4445),34 g Hydroxylaminchlorhydrat und 34 g Pyridin 1,1 g 2,4,4,6-Tetramethyl-6-hepten-3-on- oxim; Sdp. 75°C/0,3 mmHg;
    Figure imgb0015
     = 1,4745.
The following are obtained in an analogous manner:
  • - from 30 g of 3-ethyl-6-methyl-5-octen-2-one (bp 77 ° C / 6 mmHg;
    Figure imgb0012
     = 1.4476), 30 g hydroxylamine chlorohydrate and 30 g pyridine 12.8 g 3-ethyl-6-methyl-5-octen-2-one oxime; Bp 77 ° C / 0.2 mmHg;
    Figure imgb0013
     = 1.4750.
  • - from 34 g 2,4,4,6-tetramethyl-6-hepten-3-one (bp 62 o C / 5 mmHg;
    Figure imgb0014
     = 1.4445), 34 g hydroxylamine chlorohydrate and 34 g pyridine 1.1 g 2,4,4,6-tetramethyl-6-hepten-3-one oxime; Bp 75 ° C / 0.3 mmHg;
    Figure imgb0015
     = 1.4745.

Beispiel 3Example 3

Parfumerie-Base allgemein blumiger Richtung

Figure imgb0016
Perfumery base generally floral
Figure imgb0016

Ein Zusatz von 60 Teilen 5-Aethyl-7-nonen-4-on-oxim bringt dieser Base, welche ursprünglich eher Richtung Flieder zeigte, viel mehr fruchtige, süsse und wärmere Noten. Die neue Base wirkt nun angenehm orientalisch und zusätzlich ist eine Note Richtung Orchidee zu erkennen. Das neue Oxim verbindet sich ausgezeichnet mit den Ingredienzien dieser Base.The addition of 60 parts of 5-ethyl-7-nonen-4-one oxime gives this base, which originally looked more like lilac, a lot more fruity, sweet and warmer notes. The new base now has a pleasant oriental look and there is also a note of orchid. The new oxime combines excellently with the ingredients of this base.

Beispiel 4Example 4

Parfumerie-Base Richtung Tee

Figure imgb0017
Perfume base towards tea
Figure imgb0017

Gibt man zu diesem Chypre 50 Teile 5-Aethyl-7-nonen-4-on-oxim, so wird die Base überraschend Richtung Tee modifiziert. Sie wirkt nun frischer, grüner, würziger und krautiger, weist also den sehr typischen Aspekt von chinesischem Rauch-Tee auf.If 50 parts of 5-ethyl-7-nonen-4-one oxime are added to this chypre, the base is surprisingly modified towards tea. It now looks fresher, greener, more spicy and herbaceous, so it has the very typical aspect of Chinese smoke tea.

Beispiel 5Example 5

Parfumerie-Chypre

Figure imgb0018
Perfume chypre
Figure imgb0018

Gibt man zu obiger Chypre-Base 100 Teile 5-Aethyl-7-nonen-4-on-oxim, so wirkt die entstehende Base viel pudriger, fruchtiger, auch holziger und damit wärmer. Ein leicht würziger Unterton verleiht dem entstandenen Chypre ein sehr eigenwilliges Element, welches sich sehr gut in der modernen Parfümerie verwenden lässt.If 100 parts of 5-ethyl-7-nonen-4-one oxime are added to the above chypre base, the resulting base appears much more powdery, fruity, also woody and therefore warmer. A slightly spicy undertone gives the resulting chypre a very idiosyncratic element, which can be used very well in modern perfumery.

Beispiel 6Example 6

Parfumerie-Grün-Base

Figure imgb0019
Perfume Green Base
Figure imgb0019

Ein Zusatz von 20 Teilen 2,4,4,7-Tetramethyl-6-octen-3-on-oxim bringt in diese Grün-Base überraschenderweise eine sehr angenehme, fruchtige Note ein, welche sehr stark an Grapefruit erinnert. Die Base wird damit kräftig modifiziert: War die ursprüngliche Base allgemein blumig-grün, so wird die neue Base in origineller Weise Richtung modernem Cologne verändert. Sie wirkt viel frischer und wesentlich kräftiger.The addition of 20 parts of 2,4,4,7-tetramethyl-6-octen-3-one oxime surprisingly brings a very pleasant, fruity note to this green base, which is very reminiscent of grapefruit. The base is thus heavily modified: if the original base was generally flowery-green, the new base will be changed in an original way towards modern cologne. It looks much fresher and much stronger.

Beispiel 7Example 7

Parfumerie-Base Richtung Lindenblüte

Figure imgb0020
Perfume base towards linden blossom
Figure imgb0020

Gibt man zu dieser blumigen Base 200 Teile 4,7-Dimethyl-6-nonen-3-on-oxim, so wird diese primär allgemein blumige Base sehr angenehm Richtung Lindenblüte verändert. Es erscheint nun eine sehr frische, grüne und gleichzeitig viel weichere Note. Ausserdem wird der blumige Effekt verstärkt.If 200 parts of 4,7-dimethyl-6-nonen-3-one oxime are added to this flowery base, this primarily generally flowery base is changed very pleasantly in the direction of the linden blossom. A very fresh, green and at the same time much softer note appears. The floral effect is also enhanced.

Beispiel 8Example 8

Parfumerie-Base Richtung Cyclamen

Figure imgb0021
Figure imgb0022
 Perfume base towards Cyclamen
Figure imgb0021
Figure imgb0022

Gibt man zu dieser Base 50 Teile 4,7-Dimethyl-6-nonen-3-on-oxim, so wird die Base wesentlich grüner, frischer und blumiger. Der typische Cyclamen-Aspekt wird in sehr vorteilhafter Weise unterstrichen.If 50 parts of 4,7-dimethyl-6-nonen-3-one oxime are added to this base, the base becomes much greener, fresher and flowerier. The typical cyclamen aspect is emphasized in a very advantageous manner.

Ein Zusatz von 50 Teilen 3-Aethyl-6-methyl-5-octen-2-on-oxim bewirkt das Hervortreten einer fruchtig-frischen Note, welche sich sehr angenehm mit der blumigen Note verbindet.The addition of 50 parts of 3-ethyl-6-methyl-5-octen-2-one oxime causes a fruity-fresh note to emerge, which combines very pleasantly with the floral note.

Beispiel 9Example 9

Parfumerie-Base Richtung Chypre

Figure imgb0023
Figure imgb0024
 Perfume base towards Chypre
Figure imgb0023
Figure imgb0024

Gibt man zu diesem Parfumerie-Chypre 100 Teile 3-Aethyl-6-methyl-5-octen-2-on-oxim, so wird dessen Geruchscharakter in vorteilhafter Weise verstärkt. Es entsteht eine ledrige, würzige Nebennote, welche der Komposition viel mehr Volumen und Leben verleiht. Sie ist nun sehr gut geeignet für Herren-Linien.If 100 parts of 3-ethyl-6-methyl-5-octen-2-one oxime are added to this perfumery chypre, its odor character is advantageously enhanced. The result is a leathery, spicy side note, which gives the composition much more volume and life. It is now very suitable for men's lines.

BeispiellOExampleO

Parfumerie-Base Richtung Magnolia

Figure imgb0025
Figure imgb0026
 Perfume base towards Magnolia
Figure imgb0025
Figure imgb0026

Ein Zusatz von 30 Teilen 3-Aethyl-6-methyl-5-octen-2-on-oxim bringt dieser Base wesentlich mehr Volumen; sie wird weicher, blumiger und zugleich viel frischer.The addition of 30 parts of 3-ethyl-6-methyl-5-octen-2-one oxime gives this base significantly more volume; it becomes softer, flowerier and at the same time much fresher.

Nach 24 Stunden ist ein sehr deutlicher Grün-Charakter feststellbar. Die Base ist, verglichen mit der ursprünglichen Base,viel haftender.A very clear green character can be seen after 24 hours. The base is much more adhesive compared to the original base.

Beispiel 11Example 11

Parfumerie-Cologne

Figure imgb0027
Figure imgb0028
 Perfumery Cologne
Figure imgb0027
Figure imgb0028

Ein Zusatz von 50 Teilen 3-Aethyl-6-methyl-5-octen-2-on-oxim bewirkt in diesem Cologne eine viel grössere Intensität. Die Base wirkt viel grüner, kräftiger, aber auch blumiger; sie haftet auch viel länger. Die neue Substanz zeigt hier einen sehr schönen, die verschiedenen Elemente verbindenden Effekt. Die Komposition wirkt viel harmonischer durch Zusatz von 3-Aethyl-6-methyl-5-octen-2-on- oxim.Adding 50 parts of 3-ethyl-6-methyl-5-octen-2-one oxime causes a much greater intensity in this cologne. The base looks much greener, stronger, but also flowery; it also sticks much longer. The new substance shows a very nice effect that connects the different elements. The composition appears much more harmonious by adding 3-ethyl-6-methyl-5-octen-2-one oxime.

Claims (10)

1. Verbindungen der allgemeinen Formel
Figure imgb0029
worin R ein olefinisch einfach ungesättigter Kohlenwasserstoffrest ist, wobei die Ungesättigtheit sich in γ,5-Stellung befindet, und R' ein gesättigter Kohlenwasserstoffrest mit 1 bis 4 Kohlenstoffatomen ist, und wobei die Anzahl Kohlenstoffatome von R + R' 10-13 beträgt.1. Compounds of the general formula
Figure imgb0029
 wherein R is an olefinically monounsaturated hydrocarbon radical, the unsaturation is in the γ, 5-position, and R 'is a saturated hydrocarbon radical having 1 to 4 carbon atoms, and the number of carbon atoms of R + R' is 10-13. 2. Verbindungen der allgemeinen Formel I gemäss Anspruch 1, dadurch gekennzeichnet, dass die Anzahl Kohlenstoffatome von R + R' 10-12 beträgt.2. Compounds of general formula I according to claim 1, characterized in that the number of carbon atoms of R + R 'is 10-12. 3. Verbindungen der allgemeinen Formel I gemäss Anspruch 1 oder 2, dadurch gekennzeichnet, dass die Anzahl Kohlenstoffatome von R + R' 10 oder 11 beträgt.3. Compounds of general formula I according to claim 1 or 2, characterized in that the number of carbon atoms of R + R 'is 10 or 11. 4. Eine Verbindung ausgewählt aus 2,4,4,6-Tetramethyl-6-hepten-3-on-oxim, 3-Aethyl-6-methyl-5-octen-2-on- oxim, 3,3,6-Trimethyl-5-octen-2-on-oxim, 2,4,4,7-Tetramethyl-6-octen-3-on-oxim, 5-Aethyl-7-nonen-4-on-oxim, 4,7-Dimethyl-6-nonen-3-on-oxim , 2,2,7-Trimethyl-6-nonen-3-on-oxim.4. A compound selected from 2,4,4,6-tetramethyl-6-hepten-3-one oxime, 3-ethyl-6-methyl-5-octen-2-one oxime, 3,3,6- Trimethyl-5-octen-2-one oxime, 2,4,4,7-tetramethyl-6-octen-3-one oxime, 5-ethyl-7-nonen-4-one oxime, 4,7- Dimethyl-6-nonen-3-one oxime, 2,2,7-trimethyl-6-nonen-3-one oxime. 5. Verbindungen der Formel
Figure imgb0030
 worin R ein olefinisch einfach ungesättigter Kohlenwasserstoffrest ist, wobei die Ungesättigtheit sich in γ,δ-Stellung befindet, und R' ein gesättigter Kohlenwasserstoffrest mit 1 bis 4 Kohlenstoffatomen ist, und wobei die Anzahl Kohlenstoffatome von R + R' 10-13 beträgt, als Riechstoffe.5. Compounds of the formula
Figure imgb0030
 wherein R is an olefinically monounsaturated hydrocarbon radical, where the unsaturation is in the γ, δ position, and R 'is a saturated hydrocarbon radical with 1 to 4 carbon atoms, and the number of carbon atoms of R + R' is 10-13, as Fragrances. 6. Riechstoffkomposition , gekennzeichnet durch einen Gehalt an einer Verbindung der Formel
Figure imgb0031
worin R ein olefinisch einfach ungesättigter Kohlenwasserstoffrest ist, wobei die Ungesättigtheit sich in y,ö-Stellung befindet, und R' ein gesättigter Kohlenwasserstoffrest mit 1 bis 4 Kohlenstoffatomen ist, und wobei die Anzahl Kohlenstoffatome von R + R' 10-13 beträgt.6. Fragrance composition, characterized by a content of a compound of the formula
Figure imgb0031
 wherein R is an olefinically monounsaturated hydrocarbon radical, where the unsaturation is in the y, o position, and R 'is a saturated hydrocarbon radical having 1 to 4 carbon atoms, and the number of carbon atoms in R + R' is 10-13. 7. Verfahren zur Herstellung der Verbindungen der Formel
Figure imgb0032
worin R ein olefinisch einfach ungesättigter Kohlenwasserstoffrest ist, wobei die Ungesättigtheit sich in γ,δ-Stellung befindet, und R' ein gesättigter Kohlenwasserstoffrest mit 1 bis 4 Kohlenstoffatomen ist, und wobei die Anzahl Kohlenstoffatome von R + R' 10-13 beträgt, dadurch gekennzeichnet, dass man eine Verbindung der Formel
Figure imgb0033
worin R und R' obige Bedeutungen besitzen, mit Hydroxylamin bzw. einem seiner Salze umsetzt.7. Process for the preparation of the compounds of formula
Figure imgb0032
 wherein R is an olefinically monounsaturated hydrocarbon residue, wherein the unsaturation is in the γ, δ position, and R 'is a saturated hydrocarbon residue having 1 to 4 carbon atoms, and the number of carbon atoms of R + R' is 10-13, thereby characterized that you have a compound of formula
Figure imgb0033
 wherein R and R 'have the above meanings, reacted with hydroxylamine or one of its salts. 8. Verwendung von Verbindungen der Formel
Figure imgb0034
worin R ein olefinisch einfach ungesättigter Kohlenwasserstoffrest ist, wobei die Ungesättigtheit sich in γ,δ-Stellung befindet, und R' ein gesättigter Kohlenwasserstoffrest mit 1 bis 4 Kohlenstoffatomen ist, und wobei die Anzahl Kohlenstoffatome von R + R' 10-13 beträgt, als Riechstoffe.8. Use of compounds of the formula
Figure imgb0034
 wherein R is an olefinically monounsaturated hydrocarbon radical, where the unsaturation is in the γ, δ position, and R 'is a saturated hydrocarbon radical with 1 to 4 carbon atoms, and the number of carbon atoms of R + R' is 10-13, as Fragrances. 9. Verwendung von Verbindungen der allgemeinen Formel I gemäss Anspruch 8, dadurch gekennzeichnet, dass die "Anzahl Kohlenstoffatome von R + R' 10-12 beträgt.9. Use of compounds of general formula I according to claim 8, characterized in that the " number of carbon atoms of R + R 'is 10-12. 10. Verwendung von Verbindungen der allgemeinen Formel I gemäss Anspruch 9, dadurch gekennzeichnet, dass die Anzahl Kohlenstoffatome von R + R' 10 oder 11 beträgt.10. Use of compounds of general formula I according to claim 9, characterized in that the number of carbon atoms of R + R 'is 10 or 11.
EP83100415A 1982-02-03 1983-01-19 Unsaturated oximes, preparation thereof and use thereof as perfume and in the fragment compositions Expired EP0085352B1 (en)

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EP0191365A1 (en) * 1985-02-06 1986-08-20 L. GIVAUDAN &amp; CIE Société Anonyme Araliphatic oximes, process for their production and perfume compositions containing such compounds
EP0672746A1 (en) * 1994-03-18 1995-09-20 Givaudan-Roure (International) S.A. Oxime ethers and perfume and flavouring compositions containing them
WO2005110961A1 (en) * 2004-05-13 2005-11-24 Firmenich Sa Non-cyclic hindered ketones as perfuming ingredient
WO2019076926A1 (en) * 2017-10-17 2019-04-25 S H Kelkar & Company Limited Odorants and compositions comprising odorants

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US4678604A (en) * 1985-09-13 1987-07-07 Givaudan Corporation 2-(1'-hydroxyimino-ethyl)-1,3,3,4,4-pentamethylcyclopentene and fragrance compositions containing same
US5066641A (en) * 1990-09-27 1991-11-19 International Flavors & Fragrances Inc. 3,5,5-trimethylhexanal oxime and organoleptic uses thereof
DE19539625A1 (en) * 1995-10-16 1997-04-17 Haarmann & Reimer Gmbh Process for the preparation of 2,4,4,7-tetramethyl-oct-6-en-3-one and its use as a fragrance
US6872697B2 (en) * 2001-09-07 2005-03-29 Firmenich Sa Oxime as perfuming ingredient
US7494968B2 (en) 2004-05-13 2009-02-24 Firmenich Sa Non-cyclic hindered ketones as perfuming ingredient
EP2552245B1 (en) * 2010-03-26 2018-11-14 Philip Morris Products S.A. Inhibition of sensory irritation during consumption of non-smokeable tobacco products

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0191365A1 (en) * 1985-02-06 1986-08-20 L. GIVAUDAN &amp; CIE Société Anonyme Araliphatic oximes, process for their production and perfume compositions containing such compounds
EP0672746A1 (en) * 1994-03-18 1995-09-20 Givaudan-Roure (International) S.A. Oxime ethers and perfume and flavouring compositions containing them
WO2005110961A1 (en) * 2004-05-13 2005-11-24 Firmenich Sa Non-cyclic hindered ketones as perfuming ingredient
WO2019076926A1 (en) * 2017-10-17 2019-04-25 S H Kelkar & Company Limited Odorants and compositions comprising odorants
US11549079B2 (en) 2017-10-17 2023-01-10 S H Kelkar & Company Limited Odorants and compositions comprising odorants

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