EP0191365B1 - Araliphatische Oxime, Verfahren zu deren Herstellung und Riechstoffkompositionen mit einem Gehalt an solchen Verbindungen - Google Patents
Araliphatische Oxime, Verfahren zu deren Herstellung und Riechstoffkompositionen mit einem Gehalt an solchen Verbindungen Download PDFInfo
- Publication number
- EP0191365B1 EP0191365B1 EP86101178A EP86101178A EP0191365B1 EP 0191365 B1 EP0191365 B1 EP 0191365B1 EP 86101178 A EP86101178 A EP 86101178A EP 86101178 A EP86101178 A EP 86101178A EP 0191365 B1 EP0191365 B1 EP 0191365B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- compounds
- oil
- acetate
- trimethyl
- methyl
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 title claims description 21
- 239000000203 mixture Substances 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 150000002923 oximes Chemical class 0.000 title description 14
- 239000002304 perfume Substances 0.000 title description 5
- 239000003205 fragrance Substances 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 4
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- 229940022663 acetate Drugs 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 15
- -1 arylalkyl halides Chemical class 0.000 description 14
- 239000000243 solution Substances 0.000 description 12
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- MRMOPGVGWFNHIN-UHFFFAOYSA-N 1,6-dioxacycloheptadecan-7-one Chemical compound O=C1CCCCCCCCCCOCCCCO1 MRMOPGVGWFNHIN-UHFFFAOYSA-N 0.000 description 2
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- JTLPGDQZBYPAFG-UHFFFAOYSA-N 1-butyl-2,3-dihydro-1h-indene Chemical compound C1=CC=C2C(CCCC)CCC2=C1 JTLPGDQZBYPAFG-UHFFFAOYSA-N 0.000 description 2
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- FJHNSGVMPSITEQ-UHFFFAOYSA-N 10-Undecen-2-one Chemical compound CC(=O)CCCCCCCC=C FJHNSGVMPSITEQ-UHFFFAOYSA-N 0.000 description 2
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- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 2
- NFAVNWJJYQAGNB-UHFFFAOYSA-N 2-methylundecanal Chemical compound CCCCCCCCCC(C)C=O NFAVNWJJYQAGNB-UHFFFAOYSA-N 0.000 description 2
- JYVLIDXNZAXMDK-UHFFFAOYSA-N 2-pentanol Substances CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 2
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- WXCMHFPAUCOJIG-UHFFFAOYSA-N 4'-tert-Butyl-2',6'-dimethyl-3',5'-dinitroacetophenone Chemical compound CC(=O)C1=C(C)C([N+]([O-])=O)=C(C(C)(C)C)C([N+]([O-])=O)=C1C WXCMHFPAUCOJIG-UHFFFAOYSA-N 0.000 description 2
- 125000003119 4-methyl-3-pentenyl group Chemical group [H]\C(=C(/C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
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- 241000282375 Herpestidae Species 0.000 description 1
- DUKPKQFHJQGTGU-UHFFFAOYSA-N Hexyl salicylic acid Chemical compound CCCCCCOC(=O)C1=CC=CC=C1O DUKPKQFHJQGTGU-UHFFFAOYSA-N 0.000 description 1
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 1
- AXISYYRBXTVTFY-UHFFFAOYSA-N Isopropyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OC(C)C AXISYYRBXTVTFY-UHFFFAOYSA-N 0.000 description 1
- 235000010254 Jasminum officinale Nutrition 0.000 description 1
- 240000005385 Jasminum sambac Species 0.000 description 1
- 235000010663 Lavandula angustifolia Nutrition 0.000 description 1
- 235000019501 Lemon oil Nutrition 0.000 description 1
- FSOGIJPGPZWNGO-UHFFFAOYSA-N Meomammein Natural products CCC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O)C2=C1OC(=O)C=C2CCC FSOGIJPGPZWNGO-UHFFFAOYSA-N 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 239000006002 Pepper Substances 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 235000016761 Piper aduncum Nutrition 0.000 description 1
- 240000003889 Piper guineense Species 0.000 description 1
- 235000017804 Piper guineense Nutrition 0.000 description 1
- 235000008184 Piper nigrum Nutrition 0.000 description 1
- 229920000175 Pistacia lentiscus Polymers 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 235000001537 Ribes X gardonianum Nutrition 0.000 description 1
- 235000001535 Ribes X utile Nutrition 0.000 description 1
- 235000016919 Ribes petraeum Nutrition 0.000 description 1
- 244000281247 Ribes rubrum Species 0.000 description 1
- 235000002355 Ribes spicatum Nutrition 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 244000297179 Syringa vulgaris Species 0.000 description 1
- 235000004338 Syringa vulgaris Nutrition 0.000 description 1
- BCOXBEHFBZOJJZ-UHFFFAOYSA-N Z-hex-3-en-1-yl benzoate Natural products CCC=CCCOC(=O)C1=CC=CC=C1 BCOXBEHFBZOJJZ-UHFFFAOYSA-N 0.000 description 1
- IIUKCYITROTKFB-HNNXBMFYSA-N [(1s)-3-(4-methylpent-3-enyl)cyclohex-3-en-1-yl]methyl acetate Chemical compound CC(C)=CCCC1=CCC[C@H](COC(C)=O)C1 IIUKCYITROTKFB-HNNXBMFYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- UZFLPKAIBPNNCA-BQYQJAHWSA-N alpha-ionone Chemical compound CC(=O)\C=C\C1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-BQYQJAHWSA-N 0.000 description 1
- 229940062909 amyl salicylate Drugs 0.000 description 1
- 239000001399 angelica archangelica l. seed absolute Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000001138 artemisia absinthium Substances 0.000 description 1
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 description 1
- 239000010619 basil oil Substances 0.000 description 1
- 229940018006 basil oil Drugs 0.000 description 1
- 229940007550 benzyl acetate Drugs 0.000 description 1
- UMFJXFOZUPARGN-UHFFFAOYSA-N butyl 2-cyclohexylacetate Chemical compound CCCCOC(=O)CC1CCCCC1 UMFJXFOZUPARGN-UHFFFAOYSA-N 0.000 description 1
- 239000001444 canarium indicum l. oil Substances 0.000 description 1
- 239000010627 cedar oil Substances 0.000 description 1
- 239000010628 chamomile oil Substances 0.000 description 1
- 235000019480 chamomile oil Nutrition 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- NPFVOOAXDOBMCE-PLNGDYQASA-N cis-3-Hexenyl acetate Natural products CC\C=C/CCOC(C)=O NPFVOOAXDOBMCE-PLNGDYQASA-N 0.000 description 1
- RRGOKSYVAZDNKR-ARJAWSKDSA-M cis-3-hexenylacetate Chemical compound CC\C=C/CCCC([O-])=O RRGOKSYVAZDNKR-ARJAWSKDSA-M 0.000 description 1
- 239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 description 1
- 239000001524 citrus aurantium oil Substances 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000001071 citrus reticulata blanco var. mandarin Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000010636 coriander oil Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229940019836 cyclamen aldehyde Drugs 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- NYNCZOLNVTXTTP-UHFFFAOYSA-N ethyl 2-(1,3-dioxoisoindol-2-yl)acetate Chemical compound C1=CC=C2C(=O)N(CC(=O)OCC)C(=O)C2=C1 NYNCZOLNVTXTTP-UHFFFAOYSA-N 0.000 description 1
- KWBSDFFZZXXCDE-UHFFFAOYSA-N ethyl 2-ethyl-3,6,6-trimethylcyclohexa-2,4-diene-1-carboxylate Chemical compound C(C)OC(=O)C1C(C=CC(=C1CC)C)(C)C KWBSDFFZZXXCDE-UHFFFAOYSA-N 0.000 description 1
- CQHUPYQUERYPML-UHFFFAOYSA-N ethyl 2-ethyl-6,6-dimethylcyclohex-2-ene-1-carboxylate Chemical compound CCOC(=O)C1C(CC)=CCCC1(C)C CQHUPYQUERYPML-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 239000001902 eugenia caryophyllata l. bud oil Substances 0.000 description 1
- 239000001148 ferula galbaniflua oil terpeneless Substances 0.000 description 1
- ONKNPOPIGWHAQC-UHFFFAOYSA-N galaxolide Chemical compound C1OCC(C)C2=C1C=C1C(C)(C)C(C)C(C)(C)C1=C2 ONKNPOPIGWHAQC-UHFFFAOYSA-N 0.000 description 1
- 239000010648 geranium oil Substances 0.000 description 1
- 235000019717 geranium oil Nutrition 0.000 description 1
- HIGQPQRQIQDZMP-DHZHZOJOSA-N geranyl acetate Chemical compound CC(C)=CCC\C(C)=C\COC(C)=O HIGQPQRQIQDZMP-DHZHZOJOSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000001102 lavandula vera Substances 0.000 description 1
- 235000018219 lavender Nutrition 0.000 description 1
- 239000010501 lemon oil Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000013521 mastic Substances 0.000 description 1
- 239000010659 mugwort oil Substances 0.000 description 1
- LTIBJDFVBWOITR-UHFFFAOYSA-N n-(2,4,4-trimethyl-5-phenylheptan-3-ylidene)hydroxylamine Chemical compound ON=C(C(C)C)C(C)(C)C(CC)C1=CC=CC=C1 LTIBJDFVBWOITR-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- VWMVAQHMFFZQGD-UHFFFAOYSA-N p-Hydroxybenzyl acetone Natural products CC(=O)CC1=CC=C(O)C=C1 VWMVAQHMFFZQGD-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 239000001738 pogostemon cablin oil Substances 0.000 description 1
- 239000004540 pour-on Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000010666 rose oil Substances 0.000 description 1
- 235000019719 rose oil Nutrition 0.000 description 1
- 239000010668 rosemary oil Substances 0.000 description 1
- 229940058206 rosemary oil Drugs 0.000 description 1
- 239000010671 sandalwood oil Substances 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 235000012976 tarts Nutrition 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- NPFVOOAXDOBMCE-UHFFFAOYSA-N trans-3-hexenyl acetate Natural products CCC=CCCOC(C)=O NPFVOOAXDOBMCE-UHFFFAOYSA-N 0.000 description 1
- 239000010679 vetiver oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 235000014101 wine Nutrition 0.000 description 1
- ZFNVDHOSLNRHNN-UHFFFAOYSA-N xi-3-(4-Isopropylphenyl)-2-methylpropanal Chemical compound O=CC(C)CC1=CC=C(C(C)C)C=C1 ZFNVDHOSLNRHNN-UHFFFAOYSA-N 0.000 description 1
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 invention relates to new fragrances. These are the compounds of the formula wherein R is hydrogen, methyl or ethyl.
- Formula 1 is intended to encompass the syn and anti forms of oxime I.
- the anti form is preferred.
- the invention further relates to a process for the preparation of the compounds I.
- This process is characterized in that a ketone of the formula where R has the above meaning, 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 e.g. B. Organikum, organic chemical basic internship, author collective; 7th edition; VEB German Publishing House of Sciences; Berlin 1967, 375, 555:
- the oxime is conveniently left as a salt, e.g. B. react as hydrochloride or sulfate in pyridine or sodium acetate-containing alcoholic solution or in aqueous alcoholic solution with the ketone II; the reaction temperature is preferably the reflux temperature of the reaction mixture.
- the processing is expediently carried out according to methods known per se: distilling off most of the alcohol, adding an organic solvent, washing with water and finally removing the unreacted ketone.
- the starting ketones 11 are known or can be prepared by methods known per se, e.g. B. by chain extension of the commercially available diisopropyl ketone, for example by means of arylalkyl 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 either colorless or slightly colored, easily accessible, the individual approaches have a constant smell, are not irritating, stable and easy to use.
- the compounds of formula I are reminiscent of notes of black currant, sage, grapes.
- the olfactory notes are therefore completely different from those of the araliphatic oxime, 3-benzylpentan-2-, described in Swiss Patent Application No. 645/82 of February 3, 1982 (made available with European Patent Publication No. 85352 of August 10, 1983). on-oxims. That oxime smells of pepper nut, pyrazine and peas, so it lacks any fruity-berry note. This well-known oxime subsequently claimed no perfume interest.
- the odor strength in the case of the new oximes is surprisingly approximately 100 times greater than in the case of the known araliphatic oxime (compounds in 1% solution in isopropyl myristate applied to odor strips, measured immediately and / or after 24 hours). Because of this, the new compounds I can be used in a correspondingly more dilute solution.
- the compounds of the formula I can be used within wide limits, which can range, for example, from 0.01 (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 0.05 and 10%.
- 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 accordingly be used in the production of compositions and - as the above compilation shows - using a wide range of known fragrances.
- the known fragrances listed above can be used in a manner known to the perfumer, such as B. from W.A. Poucher, Perfumes, Cosmetics and Soaps2, 7th edition, Chapman and Hall, London, 1974.
- the resulting Cologne base has a much more natural effect.
- the somewhat campy note of bornylacetate, which was noticed before, is covered by the addition of the oxime.
- Sandalore's sandal note is emphasized.
- the new base also looks more diffusive.
- the effect achieved by adding the oxime corresponds to the effect that would be achieved by adding a natural product.
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
-
- Die Formel 1 soll die syn- und die anti-Formen der Oxime I umfassen. Die anti-Form ist bevorzugt.
- Die Erfindung betrifft ferner ein Verfahren zur Herstellung der Verbindungen I.
-
- 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, 555: Man lässt das Oxim zweckmässigerweise als Salz, z. B. als Hydrochlorid oder Sulfat in Pyridin oder Natriumacetat enthaltender alkoholischer Lösung bzw. in wässrig-alkoholischer Lösung mit dem Keton II reagieren; die Reaktionstemperatur ist dabei vorzugsweise die Rückflusstemperatur des Reaktionsgemisches.
- Die Aufarbeitung erfolgt zweckmässigerweise nach an sich bekannten Methoden: Abdestillieren des grössten Teiles des Alkohols, Zugabe eines organischen Lösungsmittels, Waschen mit Wasser und schliesslich Entfernen des nicht umgesetzten Ketones.
- Die Ausgangsketone 11 sind bekannt oder können nach an sich bekannten Methoden hergestellt werden, z. B. durch Kettenverlängerung des, handelsüblichen, Diisopropylketons, beispielsweise mittels Arylalkylhalogeniden.
- Die Verbindungen I weisen besondere organoleptische Eigenschaften auf, auf Grund derer sie sich vorzüglich als Riechstoffe eignen.
- Die Erfindung betrifft demgemäss auch die Verwendung der Verbindungen I als Riechstoffe.
- Die erfindungsgemässen Oxime zeichnen sich durch eine besondere Kombination von parfümistisch wertvollen Eigenschaften aus. Sie sind entweder farblos oder schwach gefärbt, leicht zugänglich, die einzelnen Ansätze sind konstant im Geruch, nicht irritierend, stabil und bequem in der Handhabung.
- Die Verbindungen der Formel I erinnern geruchlich an Noten von schwarzen Johannisbeeren, Salbei, Weintrauben.
- Die Geruchsnoten sind also völlig verschieden von denen des in der Schweizerischen Patentanmeldung Nr. 645/82 vom 03.02.1982 (zugänglich geworden mit der Europäischen Patentpublikation Nr. 85352 vom 10.08.1983) beschriebenen araliphatischen Oxims, des 3-Benzyl-pentan-2-on-oxims. Jenes Oxim riecht nach Pfeffernuss, Pyrazin und Erbsen, entbehrt also jeglicher fruchtig-beerigen Note. Dieses bekannte Oxim beanspruchte in der Folge keinerlei parfümistisches Interesse. Insbesondere aber ist die Geruchsstärke im Falle der neuen Oxime überraschenderweise ca. 100 mal grösser als im Falle des bekannten araliphatischen Oxims (Verbindungen in 1 %-iger Lösung in Isopropylmyristat auf Riechstreifen aufgebracht, sofort und/oder nach 24 Stunden gemessen). Aufgrund dieser Tatsache können die neuen Verbindungen I denn auch in entsprechend verdünnterer Lösung verwendet werden.
- Sie eignen sich aufgrund ihrer natürlichen Geruchsnoten und ihrer Haftdauer (Langzeiteffekt, insbesondere bezüglich Frische) insbesondere zur Modifizierung von bekannten, z. B.
- a) blumigen Kompositionen, in denen z. B. die Citrusnoten verstärkt zum Ausdruck kommen sollen (z. B. für Cologne-Typen u.ä., Extraits),
- b) des weiteren aber auch von fruchtigen Kompositionen, z. B. vom Typ Johannisbeere (Extrait-Typen), Kompositionen der femininen wie der männlichen Richtung), von
- c) Kompositionen mit grünen Noten, wo insbesondere ein erwünschter natürlicher Effekt erzielt wird, und schliesslich von
- d) Kompositionen, in denen generell der Charakter von natürlichen Ölen angestrebt wird, z. B. Flieder oder Lavendel.
- Die einzelnen Geruchsnoten sind die folgenden:
- Verbindung I: R=H: starker und lang haftender Geruch, grün, natürlich, nach Salbei, nach schwarzen Johannisbeeren, aber blumiger;
- Verbindung I: R=CH3: starker und sehr natürlicher Geruch nach Salbei, Weintrauben, Kelterhaus;
- Verbindung I: R=C2H5: starker und diffusiver Geruch, nach schwarzen Johannisbeeren.
- Die Verbindungen verbinden sich mit zahlreichen bekannten Riechstoffingredienzien natürlichen oder synthetischen Ursprungs, wobei die Palette der natürlichen Rohstoffe sowohl leicht-, als auch mittel - und schwer-flüchtige 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, Sandelholzöl, Styrax, Vetiveröl, Wermutöl, Ylang-Ylang-Öl, Ysopoel, Zibetöl, Zitronenöl.
- - Alkohole, wie Citronellol, Dimethylbenzylcarbinol, Dimetol ®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, Phenyläthylalkohol, 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-car- boxaldehyd, n-Dodecanal, Heliotropin, a-Hexylzimtaldehyd, Hydroxycitronellal, Methylnonylacetaldehyd, p-tert. Butyl-a-methyl-dihydro-zimt-aldehyd (z. B. Lilial® Givaudan), n-Undecen-10-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-propionylnaphthalin.
- - Ester, wie Äthylacetoacetat, 3-Äthyl-1,1-dimethyl-cyclohex-3-en-2-carbonsäure-äthylester(Givescone ®-Givaudan), 3-Äthyl-1,1,4-trimethyl-cyclohexen-3-en-2-carbonsäureäthylester (Myrascone® Givaudan), Allylphenoxyacetat, Amylsalicylat, Benzylacetat, Benzylsalicylat, Bornylacetat, Cedrylacetat, Cinnamylformiat, cis-3-Hexenylacetat, cis-3-Hexenylbenzoat, Geranylacetat, Hexylsalicylat, Isobutylsalicylat, Linalylacetat, Linalylanthranilat, Methyldihydrojasmonat, 4-[4-Methyl-3-pentenyl]-cyclohex-3-en-1-yl-carbinylacetat (z. B. Myraldyla- cetate Givaudan), Oxyoctalinformiat Giv. (Δ1-1,5,9,10-Tetramethyl-5-formoxy-octalin), Phenyläthylacetat, Styrallylacetat, Terpenylacetat, p-tert. Butylcyclohexylacetat.
- - Lactone, wie Cumarin, y-Decalacton, y-Dodecalacton, y-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-Acetal-1,1,3,4,4,6-hexamethyltetralin), Indol, Isobutylchinolin, p-Menthan-8-thiol-3-on, Methyleugenol, Methyl-1-methyl-cyclododecyläther (z. B. Madrox® Givaudan), Moschus-Verbindungen (Ketonmoschus, 12-Oxahexadecanolid (z. B. Musk 174® Naarden), 8,12-Oxido-13,14,15,16-te- tranorlabdan (Fixateur 4040).
- Die Verbindungen der Formel I lassen sich in weiten Grenzen einsetzen, die beispielsweise von 0,01 (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 0,05 und 10 %. 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.).
- Die Verbindungen I können demgemäss bei der Herstellung 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 Soaps2, 7. Auflage, Chapman und Hall, London, 1974 hervorgehend.
- a) In einem mit Rührer, Thermometer und Kühler versehenen Rundkolben werden 100 g Hydroxylaminchlorhydrat in einem Liter Äthanol und 100 g Pyridin gelöst. Man rührt eine Viertelstunde bei Raumtemperatur und gibt zu der Lösung 100 g des Ketons 11, R = H, also des 2,2.4-Trimethyl-1-phenyl-3-pentanons. Man hält das Reaktionsgemisch während 2 Stunden bei Rückflusstemperatur. Hierauf wird der grösste Teil des Äthanols, nämlich ca. 3/4, abdestilliert. Nach dem Abkühlen giesst man auf Eiswasser und nimmt in Äther auf. Die ätherische Lösung wird wie folgt gewaschen: zuerst mit Wasser. hierauf zwecks Eliminierung des Überschusses an Pyridin mit 5 %-iger verdünnter Salzsäure, dann wiederum mit Wasser bis zum Neutralpunkt. Nach dem Abdampfen des Äthers erhält man 99 g des rohen Oximes I (mit R = H), welche noch 77 g nicht umgesetztes Keton enthalten. Dieses Keton (Sdp. 90°C/1,5mmHg) wird abdestilliert.
- Der Rückstand besteht nun aus dem rohen Oxim.
- IR Spektrum; typische Banden bei 3250 cm-1 (breit),
- 1660 cm-1 (mittelstark), 930 cm-1 (stark)
- NMR; (60 MHz, CDCI3) 8 = 9,7 (breit)
- Dieses rohe Oxim kann z. B. in Form einer 10 %-igen, oder sogar einer 1 %-igen Lösung in Isopropylmyristat in der Parfümerie Verwendung finden.
- b) Wenn in obigem Verfahren das 2,4,4-Trimethyl-5-phenyl-3-hexanon als Ausgangsmaterial eingesetzt wird, erhält man das 2,4,4-Trimethyl-5-phenyl-3-hexanon-oxim;
- IR Spektrum; typische Banden bei 3250 cm-1 (breit).
- 1650 cm-1 (schwach), 935 cm-1 (stark)
- NMR; (60 MHz, CDCI3) 8 = 9,2 (breit)
- c) Wenn in obigem Verfahren das 2,4,4-Trimethyl-5-phenyl-3-heptanon als Ausgangsmaterial eingesetzt wird, erhält man das 2,4,4-Trimethyl-5-phenyl-3-heptanon-oxim;
- IR Spektrum; typische Banden bei 3300 cm-1 (breit),
- 1650 cm-1 (schwach), 940 cm-1 (stark).
- Das 2,4,4-Trimethyl-5-phenyl-3-heptanon ist durch Alkylierung von Diisopropylketon mit 1-Chlor-1-phenyl- propan erhältlich; Sdp. 78 - 79° C/0,2 mmHg.
- IR Spektrum: typische Banden bei 1705 cm-1 (stark).
-
- B. Wenn zu der Cologne-Komposition des Beispiels 2 A 50 Gewichtsteile einer 1 %-igen Lösung der Verbindung 1 (R = CH3) in Isopropylmyristat zugegeben wird, wirkt die entstandene Base frischer und grüner. Die camphrige Note wird zugedeckt und das Petitgrainöl hervorgehoben, wodurch der natürliche Charakter der entstandenen Komposition ausserordentlich gewinnt.
-
- Die Zugabe von 50 Gewichtsteilen einer 10 %-igen Lösung von 2.2.4-Trimethyl-1-phenyl-3-pentanon-oxim in Isopropylmyristat bringt obiger Base mehr Frische und mehr Leben. Der phenolische, etwas medizinische Nebengeruch verschwindet zugunsten einer minzigen, frischen, hellen Note. Die würzige Note wird schärfer, trockener, herber, mit einer Nuance nach schwarzen Johannisbeeren. Die Base eignet sich insbesondere für Herren-Parfums.
Claims (7)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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CH52785 | 1985-02-06 | ||
CH527/85 | 1985-02-06 |
Publications (2)
Publication Number | Publication Date |
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EP0191365A1 EP0191365A1 (de) | 1986-08-20 |
EP0191365B1 true EP0191365B1 (de) | 1989-08-02 |
Family
ID=4189045
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP86101178A Expired EP0191365B1 (de) | 1985-02-06 | 1986-01-30 | Araliphatische Oxime, Verfahren zu deren Herstellung und Riechstoffkompositionen mit einem Gehalt an solchen Verbindungen |
Country Status (4)
Country | Link |
---|---|
US (1) | US4654169A (de) |
EP (1) | EP0191365B1 (de) |
JP (1) | JPH0794421B2 (de) |
DE (1) | DE3664766D1 (de) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4827012A (en) * | 1988-02-23 | 1989-05-02 | Basf Corporation | Oxo-ionol carbonates |
US4992106A (en) * | 1988-02-23 | 1991-02-12 | Basf Corporation | Novel oxo-ionol carbonates useful as tobacco flavorants |
JP2001271092A (ja) | 2000-03-27 | 2001-10-02 | Takasago Internatl Corp | 芳香性漂白剤組成物 |
US7494968B2 (en) * | 2004-05-13 | 2009-02-24 | Firmenich Sa | Non-cyclic hindered ketones as perfuming ingredient |
MXPA06013035A (es) | 2004-05-13 | 2006-12-20 | Firmenich & Cie | Cetonas no ciclicas impedidas como ingrediente de perfumeria. |
JP6248861B2 (ja) * | 2014-08-19 | 2017-12-20 | 信越化学工業株式会社 | 化学増幅レジスト材料及びパターン形成方法 |
BR112020007380B1 (pt) * | 2017-10-17 | 2023-12-19 | S H Kelkar & Company Limited | Composição compreendendo odorantes, oximas úteis em tais composições, mistura de compostos de oximas e processo de preparação das referidas oximas |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4052194A (en) * | 1974-01-24 | 1977-10-04 | Merrill Wilcox | Oxime abscission agents |
US4284814A (en) * | 1978-09-08 | 1981-08-18 | Hercules Incorporated | Propene trimer and propene tetramer and use thereof in perfumery |
DE3166476D1 (en) * | 1980-08-08 | 1984-11-08 | Givaudan & Cie Sa | Unsaturated compounds, process for their preparation, their use as perfumes and the perfumed compositions containing them |
EP0085352B1 (de) * | 1982-02-03 | 1986-01-22 | L. GIVAUDAN & CIE Société Anonyme | Ungesättigte Oxime(I) und Verfahren zu deren Herstellung, Verwendung von (I) als Riechstoffe sowie Riechstoffkompositionen mit einem Gehalt an (I) |
JPS5913714A (ja) * | 1982-07-13 | 1984-01-24 | Taito Pfizer Kk | 外用消炎鎮痛剤 |
-
1986
- 1986-01-27 US US06/822,978 patent/US4654169A/en not_active Expired - Lifetime
- 1986-01-30 DE DE8686101178T patent/DE3664766D1/de not_active Expired
- 1986-01-30 EP EP86101178A patent/EP0191365B1/de not_active Expired
- 1986-02-05 JP JP61022232A patent/JPH0794421B2/ja not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
EP0191365A1 (de) | 1986-08-20 |
US4654169A (en) | 1987-03-31 |
JPS61183261A (ja) | 1986-08-15 |
JPH0794421B2 (ja) | 1995-10-11 |
DE3664766D1 (en) | 1989-09-07 |
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