EP0085352A2 - Ungesättigte Oxime(I) und Verfahren zu deren Herstellung, Verwendung von (I) als Riechstoffe sowie Riechstoffkompositionen mit einem Gehalt an (I) - Google Patents
Ungesättigte Oxime(I) und Verfahren zu deren Herstellung, Verwendung von (I) als Riechstoffe sowie Riechstoffkompositionen mit einem Gehalt an (I) Download PDFInfo
- 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
- Authority
- EP
- European Patent Office
- Prior art keywords
- carbon atoms
- oxime
- compounds
- hydrocarbon radical
- nonen
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- 150000002923 oximes Chemical class 0.000 title abstract description 8
- 239000002304 perfume Substances 0.000 title description 9
- 239000012634 fragment Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
- 239000003205 fragrance Substances 0.000 claims abstract description 11
- 229930195734 saturated hydrocarbon Natural products 0.000 claims abstract description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 6
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims abstract description 6
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- BUQWAARAXGYRLM-UHFFFAOYSA-N n-(4,7-dimethylnon-6-en-3-ylidene)hydroxylamine Chemical compound CCC(C)=CCC(C)C(CC)=NO BUQWAARAXGYRLM-UHFFFAOYSA-N 0.000 claims description 6
- YMJHCFHQWNJJDO-UHFFFAOYSA-N n-(5-ethylnon-7-en-4-ylidene)hydroxylamine Chemical compound CCCC(=NO)C(CC)CC=CC YMJHCFHQWNJJDO-UHFFFAOYSA-N 0.000 claims description 6
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 4
- SPNPFFZPVDLLEP-UHFFFAOYSA-N n-(2,2,7-trimethylnon-6-en-3-ylidene)hydroxylamine Chemical compound CCC(C)=CCCC(=NO)C(C)(C)C SPNPFFZPVDLLEP-UHFFFAOYSA-N 0.000 claims description 4
- TWZQNIXDOVTAHZ-UHFFFAOYSA-N n-(2,4,4,6-tetramethylhept-6-en-3-ylidene)hydroxylamine Chemical compound CC(C)C(=NO)C(C)(C)CC(C)=C TWZQNIXDOVTAHZ-UHFFFAOYSA-N 0.000 claims description 4
- TUSVIKPCQYWHCZ-UHFFFAOYSA-N n-(2,4,4,7-tetramethyloct-6-en-3-ylidene)hydroxylamine Chemical compound CC(C)C(=NO)C(C)(C)CC=C(C)C TUSVIKPCQYWHCZ-UHFFFAOYSA-N 0.000 claims description 4
- BVKDSDDUGCMYHR-UHFFFAOYSA-N n-(3,3,6-trimethyloct-5-en-2-ylidene)hydroxylamine Chemical compound CCC(C)=CCC(C)(C)C(C)=NO BVKDSDDUGCMYHR-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
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- GNONYQJSCSRZOC-UHFFFAOYSA-N 1-(4,4-dimethyl-2,3-dihydro-1h-naphthalen-1-yl)propan-1-one Chemical compound C1=CC=C2C(C(=O)CC)CCC(C)(C)C2=C1 GNONYQJSCSRZOC-UHFFFAOYSA-N 0.000 description 2
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- GMOYUTKNPLBTMT-UHFFFAOYSA-N 2-phenylmethoxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCC1=CC=CC=C1 GMOYUTKNPLBTMT-UHFFFAOYSA-N 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- VAJVDSVGBWFCLW-UHFFFAOYSA-N 3-Phenyl-1-propanol Chemical compound OCCCC1=CC=CC=C1 VAJVDSVGBWFCLW-UHFFFAOYSA-N 0.000 description 1
- PQGPAVMAKCASKU-UHFFFAOYSA-N 3-ethyl-6-methyloct-5-en-2-one Chemical compound CCC(C(C)=O)CC=C(C)CC PQGPAVMAKCASKU-UHFFFAOYSA-N 0.000 description 1
- 239000001623 3-phenylprop-2-enyl formate Substances 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
- LKDAMJWNPMHJDN-UHFFFAOYSA-N 4,7-dimethylnon-6-en-3-one Chemical compound CCC(C)=CCC(C)C(=O)CC LKDAMJWNPMHJDN-UHFFFAOYSA-N 0.000 description 1
- IZBHWLYKWKYMOY-UHFFFAOYSA-N 5-chloro-6-methoxypyridine-3-carbaldehyde Chemical compound COC1=NC=C(C=O)C=C1Cl IZBHWLYKWKYMOY-UHFFFAOYSA-N 0.000 description 1
- WGPCZPLRVAWXPW-NSHDSACASA-N 5-octyloxolan-2-one Chemical compound CCCCCCCC[C@H]1CCC(=O)O1 WGPCZPLRVAWXPW-NSHDSACASA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- AUBLFWWZTFFBNU-UHFFFAOYSA-N 6-butan-2-ylquinoline Chemical compound N1=CC=CC2=CC(C(C)CC)=CC=C21 AUBLFWWZTFFBNU-UHFFFAOYSA-N 0.000 description 1
- FMYCPRQGKSONCP-UHFFFAOYSA-N Acetal R Chemical compound CCCOC(C)OCCC1=CC=CC=C1 FMYCPRQGKSONCP-UHFFFAOYSA-N 0.000 description 1
- 240000006108 Allium ampeloprasum Species 0.000 description 1
- 235000005254 Allium ampeloprasum Nutrition 0.000 description 1
- 235000009051 Ambrosia paniculata var. peruviana Nutrition 0.000 description 1
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- 235000003097 Artemisia absinthium Nutrition 0.000 description 1
- 235000017731 Artemisia dracunculus ssp. dracunculus Nutrition 0.000 description 1
- 235000003261 Artemisia vulgaris Nutrition 0.000 description 1
- 240000006891 Artemisia vulgaris Species 0.000 description 1
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- 240000007436 Cananga odorata Species 0.000 description 1
- 235000005633 Chrysanthemum balsamita Nutrition 0.000 description 1
- 244000260524 Chrysanthemum balsamita Species 0.000 description 1
- 244000223760 Cinnamomum zeylanicum Species 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- PQMOXTJVIYEOQL-UHFFFAOYSA-N Cumarin Natural products CC(C)=CCC1=C(O)C(C(=O)C(C)CC)=C(O)C2=C1OC(=O)C=C2CCC PQMOXTJVIYEOQL-UHFFFAOYSA-N 0.000 description 1
- 235000018958 Gardenia augusta Nutrition 0.000 description 1
- 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
- 235000010254 Jasminum officinale Nutrition 0.000 description 1
- 240000005385 Jasminum sambac Species 0.000 description 1
- 235000019501 Lemon oil Nutrition 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 241000218378 Magnolia Species 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
- 241000233855 Orchidaceae Species 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
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 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
- 239000010619 basil oil Substances 0.000 description 1
- 229940018006 basil oil Drugs 0.000 description 1
- 229940007550 benzyl acetate Drugs 0.000 description 1
- 229940115397 bornyl 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
- 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
- 239000001111 citrus aurantium l. leaf oil Substances 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
- 235000009508 confectionery Nutrition 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
- 239000012043 crude product Substances 0.000 description 1
- 229940019836 cyclamen aldehyde Drugs 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 210000002969 egg yolk Anatomy 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
- WGPCZPLRVAWXPW-LLVKDONJSA-N gamma-Dodecalactone Natural products CCCCCCCC[C@@H]1CCC(=O)O1 WGPCZPLRVAWXPW-LLVKDONJSA-N 0.000 description 1
- OALYTRUKMRCXNH-QMMMGPOBSA-N gamma-Nonalactone Natural products CCCCC[C@H]1CCC(=O)O1 OALYTRUKMRCXNH-QMMMGPOBSA-N 0.000 description 1
- 239000010648 geranium oil Substances 0.000 description 1
- 235000019717 geranium oil Nutrition 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
- 150000002596 lactones Chemical class 0.000 description 1
- 239000000171 lavandula angustifolia l. flower oil Substances 0.000 description 1
- 239000010501 lemon oil Substances 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000013521 mastic Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000010659 mugwort oil Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000002674 ointment 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
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 239000001738 pogostemon cablin oil 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
- 239000000779 smoke Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 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
- IFDTYRKEKRSUEM-UHFFFAOYSA-N undec-2-en-6-one Chemical compound CCCCCC(=O)CCC=CC IFDTYRKEKRSUEM-UHFFFAOYSA-N 0.000 description 1
- 239000010679 vetiver oil Substances 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
- C11B9/0007—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
Landscapes
- 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)
- Detergent Compositions (AREA)
- Tea And Coffee (AREA)
- Manufacture Of Tobacco Products (AREA)
Abstract
Description
- Die Erfindung betrifft neue Riechstoffe. Es handelt sich dabei um die Verbindungen der Formel
- Die Formel I soll die syn- und die anti-Formen der Oxime I umfassen. Die anti-Form ist bevorzugt.
- Die Reste R und R' können geradkettig oder verzweigt sein.
- R und R' enthalten vorzugsweise 10 - 12, speziell bevorzugt 10 oder 11 C-Atome.
- 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: 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.
- Die Oxime können durch Destillation gereinigt werden.
- Die Ausgangsketone II sind bekannt oder können nach an sich bekannten Methoden hergestellt werden, z.B. durch Kettenverlängerung einfacher, handelsüblicher Ketone, beispielsweise mittels Allylhalogeniden.
- 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 alle entweder farblos oder höchstens 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 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.
-
- 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 Oelen angestrebt wird, z.B. Flieder oder Lavendel.
- Besonders interessante Verbindungen sind:
- Geruch: nach schwarzen Johannisbeeren, wirkt natürlich, erdig, krautig.
- Geruch: nach schwarzen Johannisbeeren, Salbei, Lavendel, Grapefruit, lauchartig.
- Geruch: nach frischem Gemüse, nach Erbsen, Gänseblümchen, Hartriegelstrauch, gut haftend.
- Geruch: nach frischem Gemüse, nach Efeu, Hartriegelstrauch.
- Weitere Beispiele von Verbindungen I sind:
- Geruch: nach frischem Gemüse, nach Tomatenblättern, nach schwarzen Johannisbeeren, sehr natürlich wirkend.
- Geruch: nach Grapefruit, Johannisbeeren, gut haftend.
- Geruch: nach Dotterblumen, sehr natürlich wirkend.
- 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®).
- 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.).
- 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.
- 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;
-
- Auf analoge Weise werden erhalten:
- - aus 41,7 g 4,7-Dimethyl-6-nonen-3-on(Siedepunkt 75°C/6 mmHg;
- - aus 25,5 g 3,3,6-Trimethyl-5-octen-2-on (Siedepunkt 75°C/6mmHg;
- - 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;
- 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 ;
- Auf analoge Weise werden erhalten:
- - aus 30 g 3-Aethyl-6-methyl-5-octen-2-on(Sdp. 77°C/ 6 mmHg;
- - aus 34 g 2,4,4,6-Tetramethyl-6-hepten-3-on(Sdp. 62oC/5 mmHg;
-
- 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.
-
- 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.
-
- 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.
-
- 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.
-
- 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.
-
- 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.
- 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.
-
- 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.
-
- 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.
- Nach 24 Stunden ist ein sehr deutlicher Grün-Charakter feststellbar. Die Base ist, verglichen mit der ursprünglichen Base,viel haftender.
-
- 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.
Claims (10)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH645/82 | 1982-02-03 | ||
CH64582 | 1982-02-03 |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0085352A2 true EP0085352A2 (de) | 1983-08-10 |
EP0085352A3 EP0085352A3 (en) | 1983-10-19 |
EP0085352B1 EP0085352B1 (de) | 1986-01-22 |
Family
ID=4191831
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP83100415A Expired EP0085352B1 (de) | 1982-02-03 | 1983-01-19 | Ungesättigte Oxime(I) und Verfahren zu deren Herstellung, Verwendung von (I) als Riechstoffe sowie Riechstoffkompositionen mit einem Gehalt an (I) |
Country Status (4)
Country | Link |
---|---|
US (1) | US4544714A (de) |
EP (1) | EP0085352B1 (de) |
JP (1) | JPS58134071A (de) |
DE (1) | DE3361874D1 (de) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0191365A1 (de) * | 1985-02-06 | 1986-08-20 | L. GIVAUDAN & CIE Société Anonyme | Araliphatische Oxime, Verfahren zu deren Herstellung und Riechstoffkompositionen mit einem Gehalt an solchen Verbindungen |
EP0672746A1 (de) * | 1994-03-18 | 1995-09-20 | Givaudan-Roure (International) S.A. | Oximäther und sie enthaltenden Riech- und Geschmackstoffkompositionen |
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 | ODORANT SUBSTANCES AND COMPOSITIONS COMPRISING ODORANT SUBSTANCES |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 (de) * | 1995-10-16 | 1997-04-17 | Haarmann & Reimer Gmbh | Verfahren zur Herstellung von 2,4,4,7-Tetramethyl-oct-6-en-3-on und dessen Verwendung als Riechstoff |
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 |
DK2552245T3 (en) * | 2010-03-26 | 2019-01-07 | Philip Morris Products Sa | INHIBITION OF SENSORY IRRITATION UNDER CONSUMPTION OF NON-SMOKABLE TOBACCO PRODUCTS |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3453317A (en) * | 1962-07-11 | 1969-07-01 | Hoffmann La Roche | Unsaturated carbonyl compounds and processes |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1305994A (fr) * | 1961-07-21 | 1962-10-13 | Rhone Poulenc Sa | Nouveaux dérivés terpéniques et leur préparation |
US3637533A (en) * | 1967-02-14 | 1972-01-25 | Givaudan Corp | Perfume-containing compositions containing certain oximes as olfactory agents |
CH597125A5 (de) * | 1973-07-05 | 1978-03-31 | Hoffmann La Roche | |
US4052194A (en) * | 1974-01-24 | 1977-10-04 | Merrill Wilcox | Oxime abscission agents |
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 |
-
1983
- 1983-01-19 EP EP83100415A patent/EP0085352B1/de not_active Expired
- 1983-01-19 DE DE8383100415T patent/DE3361874D1/de not_active Expired
- 1983-01-26 US US06/461,053 patent/US4544714A/en not_active Expired - Lifetime
- 1983-02-02 JP JP58016016A patent/JPS58134071A/ja active Granted
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3453317A (en) * | 1962-07-11 | 1969-07-01 | Hoffmann La Roche | Unsaturated carbonyl compounds and processes |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0191365A1 (de) * | 1985-02-06 | 1986-08-20 | L. GIVAUDAN & CIE Société Anonyme | Araliphatische Oxime, Verfahren zu deren Herstellung und Riechstoffkompositionen mit einem Gehalt an solchen Verbindungen |
EP0672746A1 (de) * | 1994-03-18 | 1995-09-20 | Givaudan-Roure (International) S.A. | Oximäther und sie enthaltenden Riech- und Geschmackstoffkompositionen |
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 | ODORANT SUBSTANCES AND COMPOSITIONS COMPRISING ODORANT SUBSTANCES |
US11549079B2 (en) | 2017-10-17 | 2023-01-10 | S H Kelkar & Company Limited | Odorants and compositions comprising odorants |
Also Published As
Publication number | Publication date |
---|---|
DE3361874D1 (en) | 1986-03-06 |
US4544714A (en) | 1985-10-01 |
EP0085352A3 (en) | 1983-10-19 |
JPH0361661B2 (de) | 1991-09-20 |
EP0085352B1 (de) | 1986-01-22 |
JPS58134071A (ja) | 1983-08-10 |
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