EP0191365A1 - Araliphatic oximes, process for their production and perfume compositions containing such compounds - Google Patents
Araliphatic oximes, process for their production and perfume compositions containing such compounds Download PDFInfo
- Publication number
- EP0191365A1 EP0191365A1 EP86101178A EP86101178A EP0191365A1 EP 0191365 A1 EP0191365 A1 EP 0191365A1 EP 86101178 A EP86101178 A EP 86101178A EP 86101178 A EP86101178 A EP 86101178A EP 0191365 A1 EP0191365 A1 EP 0191365A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- compounds
- oil
- methyl
- trimethyl
- oximes
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 23
- 239000000203 mixture Substances 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title claims abstract description 10
- 150000002923 oximes Chemical class 0.000 title abstract description 16
- 239000002304 perfume Substances 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000003205 fragrance Substances 0.000 claims abstract description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- MZNPUDAQSVBNFM-UHFFFAOYSA-N CC(CC1=CC=CC=C1)(C(C(C)C)=NO)C Chemical compound CC(CC1=CC=CC=C1)(C(C(C)C)=NO)C MZNPUDAQSVBNFM-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 3
- -1 arylalkyl halides Chemical class 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 8
- 230000035943 smell Effects 0.000 description 8
- 150000002576 ketones Chemical class 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 4
- HGDVHRITTGWMJK-UHFFFAOYSA-N 2,6-dimethylheptan-2-ol Chemical compound CC(C)CCCC(C)(C)O HGDVHRITTGWMJK-UHFFFAOYSA-N 0.000 description 4
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- ZYEMGPIYFIJGTP-UHFFFAOYSA-N O-methyleugenol Chemical compound COC1=CC=C(CC=C)C=C1OC ZYEMGPIYFIJGTP-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 240000001890 Ribes hudsonianum Species 0.000 description 4
- 235000016954 Ribes hudsonianum Nutrition 0.000 description 4
- 235000001466 Ribes nigrum Nutrition 0.000 description 4
- KGEKLUUHTZCSIP-HOSYDEDBSA-N [(1s,4s,6r)-1,7,7-trimethyl-6-bicyclo[2.2.1]heptanyl] acetate Chemical compound C1C[C@]2(C)[C@H](OC(=O)C)C[C@H]1C2(C)C KGEKLUUHTZCSIP-HOSYDEDBSA-N 0.000 description 4
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 4
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 4
- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- YBUIAJZFOGJGLJ-SWRJLBSHSA-N 1-cedr-8-en-9-ylethanone Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@@H]1C(C)=C(C(C)=O)C2 YBUIAJZFOGJGLJ-SWRJLBSHSA-N 0.000 description 3
- NGYMOTOXXHCHOC-UHFFFAOYSA-N 3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pentan-2-ol Chemical compound CC(O)C(C)CCC1CC=C(C)C1(C)C NGYMOTOXXHCHOC-UHFFFAOYSA-N 0.000 description 3
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
- 235000002020 sage Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 2
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 2
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 2
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 2
- WUOACPNHFRMFPN-SECBINFHSA-N (S)-(-)-alpha-terpineol Chemical compound CC1=CC[C@@H](C(C)(C)O)CC1 WUOACPNHFRMFPN-SECBINFHSA-N 0.000 description 2
- MRMOPGVGWFNHIN-UHFFFAOYSA-N 1,6-dioxacycloheptadecan-7-one Chemical compound O=C1CCCCCCCCCCOCCCCO1 MRMOPGVGWFNHIN-UHFFFAOYSA-N 0.000 description 2
- 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
- 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
- QACBYNLZEUNZSC-UHFFFAOYSA-N 1-methoxy-1-methylcyclododecane Chemical compound COC1(C)CCCCCCCCCCC1 QACBYNLZEUNZSC-UHFFFAOYSA-N 0.000 description 2
- FJHNSGVMPSITEQ-UHFFFAOYSA-N 10-Undecen-2-one Chemical compound CC(=O)CCCCCCCC=C FJHNSGVMPSITEQ-UHFFFAOYSA-N 0.000 description 2
- BXKWFUZSYDBWLW-UHFFFAOYSA-N 2,4,4-trimethyl-5-phenylheptan-3-one Chemical compound CC(C)C(=O)C(C)(C)C(CC)C1=CC=CC=C1 BXKWFUZSYDBWLW-UHFFFAOYSA-N 0.000 description 2
- 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
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- 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
- OALYTRUKMRCXNH-UHFFFAOYSA-N 5-pentyloxolan-2-one Chemical compound CCCCCC1CCC(=O)O1 OALYTRUKMRCXNH-UHFFFAOYSA-N 0.000 description 2
- VUFZVGQUAVDKMC-UHFFFAOYSA-N Allyl phenoxyacetate Chemical compound C=CCOC(=O)COC1=CC=CC=C1 VUFZVGQUAVDKMC-UHFFFAOYSA-N 0.000 description 2
- ZCTQGTTXIYCGGC-UHFFFAOYSA-N Benzyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 description 2
- 241001090476 Castoreum Species 0.000 description 2
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 2
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 2
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 2
- 241000402754 Erythranthe moschata Species 0.000 description 2
- 239000005770 Eugenol Substances 0.000 description 2
- 235000018958 Gardenia augusta Nutrition 0.000 description 2
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 2
- 239000005792 Geraniol Substances 0.000 description 2
- DUKPKQFHJQGTGU-UHFFFAOYSA-N Hexyl salicylic acid Chemical compound CCCCCCOC(=O)C1=CC=CC=C1O DUKPKQFHJQGTGU-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 244000178870 Lavandula angustifolia Species 0.000 description 2
- 241000234269 Liliales Species 0.000 description 2
- 235000015511 Liquidambar orientalis Nutrition 0.000 description 2
- GLZPCOQZEFWAFX-JXMROGBWSA-N Nerol Natural products CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 description 2
- DYUQAZSOFZSPHD-UHFFFAOYSA-N Phenylpropanol Chemical compound CCC(O)C1=CC=CC=C1 DYUQAZSOFZSPHD-UHFFFAOYSA-N 0.000 description 2
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- 240000007164 Salvia officinalis Species 0.000 description 2
- 239000004870 Styrax Substances 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- 241000219094 Vitaceae Species 0.000 description 2
- 229940022663 acetate Drugs 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- QUMXDOLUJCHOAY-UHFFFAOYSA-N alpha-methylbenzyl acetate Natural products CC(=O)OC(C)C1=CC=CC=C1 QUMXDOLUJCHOAY-UHFFFAOYSA-N 0.000 description 2
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 2
- 229940115397 bornyl acetate Drugs 0.000 description 2
- HQKQRXZEXPXXIG-VJOHVRBBSA-N chembl2333940 Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@H]1[C@@](OC(C)=O)(C)CC2 HQKQRXZEXPXXIG-VJOHVRBBSA-N 0.000 description 2
- 229940043350 citral Drugs 0.000 description 2
- 235000000484 citronellol Nutrition 0.000 description 2
- 239000001111 citrus aurantium l. leaf oil Substances 0.000 description 2
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 229960002217 eugenol Drugs 0.000 description 2
- IFYYFLINQYPWGJ-UHFFFAOYSA-N gamma-decalactone Chemical compound CCCCCCC1CCC(=O)O1 IFYYFLINQYPWGJ-UHFFFAOYSA-N 0.000 description 2
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 2
- 229940113087 geraniol Drugs 0.000 description 2
- HIGQPQRQIQDZMP-DHZHZOJOSA-N geranyl acetate Chemical compound CC(C)=CCC\C(C)=C\COC(C)=O HIGQPQRQIQDZMP-DHZHZOJOSA-N 0.000 description 2
- 235000021021 grapes Nutrition 0.000 description 2
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 2
- 239000000171 lavandula angustifolia l. flower oil Substances 0.000 description 2
- SDQFDHOLCGWZPU-UHFFFAOYSA-N lilial Chemical compound O=CC(C)CC1=CC=C(C(C)(C)C)C=C1 SDQFDHOLCGWZPU-UHFFFAOYSA-N 0.000 description 2
- 229930007744 linalool Natural products 0.000 description 2
- UWKAYLJWKGQEPM-LBPRGKRZSA-N linalyl acetate Chemical compound CC(C)=CCC[C@](C)(C=C)OC(C)=O UWKAYLJWKGQEPM-LBPRGKRZSA-N 0.000 description 2
- 229940041616 menthol Drugs 0.000 description 2
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 description 2
- PRHTXAOWJQTLBO-UHFFFAOYSA-N methyleugenol Natural products COC1=CC=C(C(C)=C)C=C1OC PRHTXAOWJQTLBO-UHFFFAOYSA-N 0.000 description 2
- 229940116837 methyleugenol Drugs 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- MDHYEMXUFSJLGV-UHFFFAOYSA-N phenethyl acetate Chemical compound CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 2
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- NJGBTKGETPDVIK-UHFFFAOYSA-N raspberry ketone Chemical compound CC(=O)CCC1=CC=C(O)C=C1 NJGBTKGETPDVIK-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229940116411 terpineol Drugs 0.000 description 2
- PHXATPHONSXBIL-UHFFFAOYSA-N xi-gamma-Undecalactone Chemical compound CCCCCCCC1CCC(=O)O1 PHXATPHONSXBIL-UHFFFAOYSA-N 0.000 description 2
- BGCIAWBDYRWKEK-UHFFFAOYSA-N (1-butylcyclohexyl) acetate Chemical compound CCCCC1(OC(C)=O)CCCCC1 BGCIAWBDYRWKEK-UHFFFAOYSA-N 0.000 description 1
- BCOXBEHFBZOJJZ-ARJAWSKDSA-N (3Z)-hex-3-en-1-yl benzoate Chemical compound CC\C=C/CCOC(=O)C1=CC=CC=C1 BCOXBEHFBZOJJZ-ARJAWSKDSA-N 0.000 description 1
- 229940098795 (3z)- 3-hexenyl acetate Drugs 0.000 description 1
- TWJFINAHYOYYOB-DHZHZOJOSA-N (6e)-2,4,4,7-tetramethylnona-6,8-dien-3-one Chemical compound CC(C)C(=O)C(C)(C)C\C=C(/C)C=C TWJFINAHYOYYOB-DHZHZOJOSA-N 0.000 description 1
- FXCYGAGBPZQRJE-ZHACJKMWSA-N 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one Chemical compound CC1=CCCC(C)(C)C1\C=C\C(=O)CCC=C FXCYGAGBPZQRJE-ZHACJKMWSA-N 0.000 description 1
- VPKMGDRERYMTJX-CMDGGOBGSA-N 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one Chemical compound CCC(=O)\C=C\C1C(C)=CCCC1(C)C VPKMGDRERYMTJX-CMDGGOBGSA-N 0.000 description 1
- MZMVVHAHSRJOEO-UHFFFAOYSA-N 1-chloropropylbenzene Chemical compound CCC(Cl)C1=CC=CC=C1 MZMVVHAHSRJOEO-UHFFFAOYSA-N 0.000 description 1
- BFNMZJQMWPPBKE-UHFFFAOYSA-N 1-oxo-3h-2-benzofuran-4-carbonitrile Chemical compound C1=CC=C(C#N)C2=C1C(=O)OC2 BFNMZJQMWPPBKE-UHFFFAOYSA-N 0.000 description 1
- DHFXVWXVZUATDN-UHFFFAOYSA-N 2,2,4-trimethyl-1-phenylpentan-3-one Chemical compound CC(C)C(=O)C(C)(C)CC1=CC=CC=C1 DHFXVWXVZUATDN-UHFFFAOYSA-N 0.000 description 1
- OPFWNTRCBNGIGG-UHFFFAOYSA-N 2,2,8-trimethylnon-7-en-3-ol Chemical compound CC(C)=CCCCC(O)C(C)(C)C OPFWNTRCBNGIGG-UHFFFAOYSA-N 0.000 description 1
- TWJFINAHYOYYOB-UHFFFAOYSA-N 2,4,4,7-tetramethylnona-6,8-dien-3-one Chemical compound CC(C)C(=O)C(C)(C)CC=C(C)C=C TWJFINAHYOYYOB-UHFFFAOYSA-N 0.000 description 1
- TUQIRLRILHJROY-UHFFFAOYSA-N 2,4,4-trimethyl-5-phenylhexan-3-one Chemical compound CC(C)C(=O)C(C)(C)C(C)C1=CC=CC=C1 TUQIRLRILHJROY-UHFFFAOYSA-N 0.000 description 1
- SUSANQWSCSKXPF-UHFFFAOYSA-N 2-(2-methylpropoxy)benzoic acid Chemical compound CC(C)COC1=CC=CC=C1C(O)=O SUSANQWSCSKXPF-UHFFFAOYSA-N 0.000 description 1
- FAQVGPWFQGGIPP-UHFFFAOYSA-N 2-(2-methylpropyl)quinoline Chemical compound C1=CC=CC2=NC(CC(C)C)=CC=C21 FAQVGPWFQGGIPP-UHFFFAOYSA-N 0.000 description 1
- HMKKIXGYKWDQSV-SDNWHVSQSA-N 2-Pentyl-3-phenyl-2-propenal Chemical compound CCCCC\C(C=O)=C/C1=CC=CC=C1 HMKKIXGYKWDQSV-SDNWHVSQSA-N 0.000 description 1
- 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
- HMNKTRSOROOSPP-UHFFFAOYSA-N 3-Ethylphenol Chemical compound CCC1=CC=CC(O)=C1 HMNKTRSOROOSPP-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
- 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
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 235000009051 Ambrosia paniculata var. peruviana Nutrition 0.000 description 1
- RANVDUNFZBMTBK-UHFFFAOYSA-N Amyl salicylate Chemical compound CCCCCOC(=O)C1=CC=CC=C1O RANVDUNFZBMTBK-UHFFFAOYSA-N 0.000 description 1
- 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
- DBPLRLXFFUKDDB-UHFFFAOYSA-N Bornylacetat Natural products C1CC2(C)C(C(=O)C)CC1C2(C)C DBPLRLXFFUKDDB-UHFFFAOYSA-N 0.000 description 1
- GTNALRCLENSTPJ-UHFFFAOYSA-N C(C1=CC=CC=C1)C(C(C)=NO)CC Chemical compound C(C1=CC=CC=C1)C(C(C)=NO)CC GTNALRCLENSTPJ-UHFFFAOYSA-N 0.000 description 1
- LCSKTQDIZKFDQN-UHFFFAOYSA-N CC(C)C(C(C(C)C1=CC=CC=C1)(C)C)=NO Chemical compound CC(C)C(C(C(C)C1=CC=CC=C1)(C)C)=NO LCSKTQDIZKFDQN-UHFFFAOYSA-N 0.000 description 1
- 0 CC(C)C(C(C)(C)C*)=NO Chemical compound CC(C)C(C(C)(C)C*)=NO 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- 240000007436 Cananga odorata Species 0.000 description 1
- 235000002566 Capsicum Nutrition 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
- 241000282375 Herpestidae Species 0.000 description 1
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 1
- 235000010663 Lavandula angustifolia Nutrition 0.000 description 1
- 235000019501 Lemon oil Nutrition 0.000 description 1
- WHIJSULEEDNKPD-UHFFFAOYSA-N Linalyl anthranilate Chemical compound CC(C)=CCCC(C)(C=C)OC(=O)C1=CC=CC=C1N WHIJSULEEDNKPD-UHFFFAOYSA-N 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
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 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
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 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
- 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
- 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
- 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
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 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
- IFYYFLINQYPWGJ-VIFPVBQESA-N gamma-Decalactone Natural products CCCCCC[C@H]1CCC(=O)O1 IFYYFLINQYPWGJ-VIFPVBQESA-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
- PHXATPHONSXBIL-JTQLQIEISA-N gamma-Undecalactone Natural products CCCCCCC[C@H]1CCC(=O)O1 PHXATPHONSXBIL-JTQLQIEISA-N 0.000 description 1
- 229940020436 gamma-undecalactone Drugs 0.000 description 1
- HIGQPQRQIQDZMP-UHFFFAOYSA-N geranil acetate Natural products CC(C)=CCCC(C)=CCOC(C)=O HIGQPQRQIQDZMP-UHFFFAOYSA-N 0.000 description 1
- 239000010648 geranium oil Substances 0.000 description 1
- 235000019717 geranium oil Nutrition 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
- UWKAYLJWKGQEPM-UHFFFAOYSA-N linalool acetate Natural products CC(C)=CCCC(C)(C=C)OC(C)=O UWKAYLJWKGQEPM-UHFFFAOYSA-N 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
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 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
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000000126 substance 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
- 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 I 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. Organics, basic organic chemistry 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. react as hydrochloride or sulfate in an alcoholic solution containing pyridine or sodium acetate or in an 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 II are known or can be prepared by methods known per se, e.g. by chain extension of the commercially available diisopropyl ketone, for example using 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 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 moving 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, 1%s, lotions, creams, shampoos, soaps, ointments, powder, 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, e.g. from W.A. Poucher, Perfumes, Cosmetics and Soaps 2, 7th edition, Chapman and Hall. London. Emerged in 1974.
- the residue now consists of the crude oxime.
- This crude oxime can e.g. in the form of a 10% or even a 1% solution in isopropyl myristate can be used in perfumery.
- the 2,4,4-trimethyl-5-phenyl-3-heptanone can be obtained by alkylating diisopropyl ketone with 1-chloro-l-phenylpropane; Bp 78-79 ° C / 0.2 mmHg.
- the resulting Cologne base appears much more natural.
- the slightly campy note of bornylacetate that 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.
Abstract
Die Erfindung betrifft neue Riechstoffe, und zwar neue Oxime der Formel <IMAGE> worin R Wasserstoff, Methyl oder Äthyl ist. 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 of the formula <IMAGE> in which R is hydrogen, methyl or ethyl. 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
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 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 ein Keton der Formel
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.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. Organics, basic organic chemistry 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. react as hydrochloride or sulfate in an alcoholic solution containing pyridine or sodium acetate or in an aqueous-alcoholic solution with the ketone II; the reaction temperature is preferably the reflux temperature of the reaction mixture.
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.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.
Die Ausgangsketone II sind bekannt oder können nach an sich bekannten Methoden hergestellt werden, z.B. durch Kettenverlängerung des, handelsüblichen, Diisopropylketons, beispielsweise mittels Arylalkylhalogeniden.The starting ketones II are known or can be prepared by methods known per se, e.g. by chain extension of the commercially available diisopropyl ketone, for example using arylalkyl 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 entweder farblos oder 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 either colorless or slightly colored, easily accessible, the individual approaches have a constant smell, are not irritating, stable and easy to use.
Die Verbindungen der Formel I erinnern geruchlich an Noten von schwarzen Johannisbeeren. Salbei. Weintrauben.The compounds of formula I are reminiscent of notes of black currant. Sage. Grapes.
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 l%-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.The olfactory notes are therefore completely different from those of the araliphatic oxime described in Swiss Patent Application No. 645/82 of February 3, 1982 (accessible with European Patent Publication No. 85352 of August 10, 1983). of 3-benzylpentane - 2-one oxime. That oxime smells of pepper nut. Pyrazine and peas, so lacks any fruity-berry note. This well-known oxime subsequently claimed no perfume interest. In particular, however, the odor intensity 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.
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 Oelen angestrebt wird, z.B. Flieder oder Lavendel.
- a) floral compositions in which, for example, the citrus notes are to be increasingly expressed (e.g. for Cologne types and the like, extraits).
- b) furthermore also of fruity compositions, for example of the type currant (portrait types), compositions of the feminine and the male direction), of
- c) compositions with green notes, where in particular a desired natural effect is achieved, and finally by
- d) compositions in which the character of natural oils is generally sought, eg lilac or lavender.
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=CZHS: starker und diffusiver Geruch, nach schwarzen Johannisbeeren.
- Compound I: R = H : strong and long-lasting smell, green, natural, of sage, of black currants, but more floral;
- Compound I: R = CH 3 : strong and very natural smell of sage, grapes, wine press;
- Compound I: R = C Z H S : strong and diffusive smell, of black currants.
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 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 R IFF bzw. Cedartone R Givaudan), Corianderöl, Eichenmoos, Elemiöl, Galbanum- öl. 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-Oel, Ysopoel, Zibetöl, Zitronenöl.
- - Alkohole, wie Citronellol. Dimethylbenzylcarbinol, Dimetol R Giv. (2,6-Dimethyl-2-heptanol), Geraniol, Linalool, Menthol, 3-Methyl-5- (2',2',3'-trimethyl-cyclo- pent-3'-en-1'-yl)-pentan-2-ol (Sandalore R 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-carboxalde- hyd, n-Dodecanal, Heliotropin, a-Hexylzimtaldehyd, Hydroxycitronellal, Methylnonylacetaldehyd, p-tert. Butyl-a-methyl-dihydro-zimt-aldehyd (z.B. Lilial R 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 Aethylacetoacetat, 3-Aethyl-1,1-dimethyl-c-yclohex-3-en-2-carbonsäure-äthylester(Givescone R Givaudan), 3-Aethyl-1,1.4-trimethyl-cyclohexen-3-en-2-carbon- säureäthylester (Myrascone Givaudan), Allylphenoxyacetat. Amylsalicylat, Benzylacetat, Benzylsalicylat, Bornylacetat, Cedrylacetat, Cinnamylformiat, cis-3-Hexenylace- tat, cis-3-Hexenylbenzoat, Geranylacetat, Hexylsalicylat. Isobutylsalicylat, Linalylacetat, Linalylanthranilat, Methyldihydrojasmonat, 4-[4-Methyl-3-pentenyl]-cyclohex-3--en-1-yl-carbinylacetat (z.B. Myraldylacetat R Givaudan), Oxyoctalinformiat Giv. (Δ1-1,5,9,10-Tetramethyl--5-formoxy-octalin), Phenyläthylacetat, Styrallylacetat, Terpenylacetat, p-tert. Butylcyclohexylacetat.
- - Lactone, wie Cumarin, γ-Decalacton, γ-Dodecalacton, γ-Nonalacton, γ-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-hexamethylte- tralin), Indol, Isobutylchinolin, p-Menthan-8-thiol-3-on, Methyleugenol, Methyl-1-methyl-cyciododecyläther (z.B. Madrox R Givaudan), Moschus-Verbindungen (Ketonmoschus, 12-Oxahexadecanolid (z.B. Musk 174 R Naarden), 8.12-Oxi- do-13,14,15,16-tetranorlabdan (Fixateur 404 R).
- -volatile components, and that of synthetics can include representatives from practically all classes of substances. as can be seen from the following compilation:
- - Natural products such as angelica seed oil, tree moss absolute. Basil oil, mugwort oil, bergamot oil, castoreum, acetylated cedarwood oil (eg Vertofix R IFF or Cedartone R Givaudan), coriander oil, oak moss, elemi oil, galbanum oil. Geranium oil. Jasmin Absolue and its substitutes, chamomile oil, lavender 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, Dimetol R 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 R Givaudan). Nerol. Phenylethyl alcohol, phenylpropyl 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-carboxalde- hyd, n-dodecanal, heliotropin, a-hexylcinnamaldehyde, hydroxycitronellal, methylnonylacetaldehyde, p-tert. Butyl-a-methyl-dihydro-cinnamon aldehyde (e.g. Lilial R Givaudan), n-undecen-10-al.
- - Ketones such as acetylcedrene, allyl ionone, p-hydroxybenzyl acetone. a-Jonon, 2,4,4,7-tetramethyl-6,8-nonadien-3-one, p-methyl acetophenone, methyl ionone, 1,2,3,4-tetrahydro-1,1-dimethyl-4-propionylnaphthalene.
- - Esters, such as ethyl acetoacetate, 3-ethyl-1,1-dimethyl-c-yclohex-3-en-2-carboxylic acid ethyl ester (Givescone R Givaudan), 3-ethyl-1,1,4-trimethyl-cyclohexen-3-ene -2-carboxylic acid ethyl ester (Myrascone Givaudan), allylphenoxyacetate. Amyl salicylate, benzyl acetate, benzyl salicylate, bornyl acetate, cedrylacetate, cinnamyl formate, cis-3-hexenylacetate, cis-3-hexenyl benzoate, geranyl acetate, hexyl salicylate. Isobutyl salicylate, linalyl acetate, linalyl anthranilate, methyl dihydrojasmonate, 4- [4-methyl-3-pentenyl] cyclohex-3-en-1-yl-carbinyl acetate (e.g. myraldylacetate R Givaudan), oxyoctaline formate giv. (Δ 1- 1,5,9,10-tetramethyl-5-formoxy-octalin), phenyl ethyl acetate, styrallyl acetate, terpenyl acetate, p-tert. Butylcyclohexyl acetate.
- Lactones, such as coumarin, γ-decalactone, γ-dodecalactone, γ-nonalactone, γ-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-acetal-1,1,3,4,4,6-hexamethyl tetralin), indole, Isobutylquinoline, p-menthan-8-thiol-3-one, methyleugenol, methyl 1-methyl-cyciododecyl ether (e.g. Madrox R Givaudan), musk compounds (ketone musk, 12-oxahexadecanolide (e.g. Musk 174 R Naarden), 8.12-oxi - do-13,14,15,16-tetranorlabdan ( F ixateur 4 04 R ).
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.).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 moving 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, extraits, lotions, creams, shampoos, soaps, ointments, powder, deodorants, detergents, tobacco, 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 Soaps 2, 7. Auflage, Chapman und Hall. London. 1974 hervorgehend.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. 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. Emerged in 1974.
a) In einem mit Rührer, Thermometer und Kühler versehenen Rundkolben werden 100 g Hydroxylaminchlorhydrat in einem Liter Aethanol und 100 g Pyridin gelöst. Man rührt eine Viertelstunde bei Raumtemperatur und gibt zu der Lösung 100 g des Ketons II, 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 Aethanols. nämlich ca. 3/4. abdestilliert. Nach dem Abkühlen giesst man auf Eiswasser und nimmt in Aether auf. Die ätherische Lösung wird wie folgt gewaschen: zuerst mit Wasser, hierauf zwecks Eliminierung des Ueberschusses an Pyridin mit 5%-iger verdünnter Salzsäure, dann wiederum mit Wasser bis zum Neutral- punkt.Nach dem Abdampfen des Aethers 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.a) 100 g of hydroxylamine chlorohydrate are dissolved in one liter of ethanol and 100 g of pyridine in a round-bottomed flask equipped with a stirrer, thermometer and cooler. The mixture is stirred for a quarter of an hour at room temperature and 100 g of the ketone II, R = H., ie the 2,2,4-trimethyl-1-phenyl-3-pentanone, are added to the solution. The reaction mixture is kept at the reflux temperature for 2 hours. This is where most of the ethanol comes in. namely about 3/4. distilled off. After cooling, pour on ice water and take up in ether. The ethereal solution is washed as follows: first with water, then to eliminate the excess pyridine with 5% dilute hydrochloric acid, then again with water to the neutral point. After evaporation of the ether, 99 g of the crude oxime I are obtained (with R = H), which still contain 77 g of unreacted ketone. This ketone (bp 90 ° C / 1.5mmHg) is distilled off.
Der Rückstand besteht nun aus dem rohen Oxim.The residue now consists of the crude oxime.
IR Spektrum; typische Banden bei 3250 cm-1 (breit), 1660 cm-1 (mittelstark), 930 cm-1 (stark) NMR: (60 MHz. CDC13) δ = 9,7 (breit)IR spectrum; typical bands at 3250 cm -1 (wide), 1660 cm -1 (medium), 93 0 cm -1 (strong) NMR: (60 MHz. CDC1 3 ) δ = 9.7 (wide)
Dieses rohe Oxim kann z.B. in Form einer 10%-igen, oder sogar einer l%-igen Lösung in Isopropylmyristat in der Parfümerie Verwendung finden.This crude oxime can e.g. in the form of a 10% or even a 1% solution in isopropyl myristate can be used in perfumery.
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;b) If the 2,4,4-trimethyl-5-phenyl-3-hexanone is used as the starting material in the above process, the 2,4,4-trimethyl-5-phenyl-3-hexanone oxime is obtained;
IR Spektrum; typische Banden bei 3250 cm-1 (breit), 1650 cm-1 (schwach). 935 cm-1 (stark) NMR; (60 MHz. CDC13) δ = 9,2 (breit)IR spectrum; typical bands at 3250 cm -1 (wide), 1 650 cm -1 (weak). 935 cm -1 (strong) NMR; (60 MHz. CDC13) δ = 9.2 (broad)
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;c) If the 2,4,4-trimethyl-5-phenyl-3-heptanone is used as the starting material in the above process, the 2,4,4-trimethyl-5-phenyl-3-heptanone oxime is obtained;
IR Spektrum; typische Banden bei 3300 cm-1 (breit), 1650 cm-1 (schwach). 940 cm-1 (stark).IR spectrum; typical bands at 3300 cm -1 (wide), 1650 cm -1 (weak). 940 cm -1 (strong).
Das 2,4,4-Trimethyl-5-phenyl-3-heptanon ist durch Alkylierung von Diisopropylketon mit 1-Chlor-l-phenyl--propan erhältlich; Sdp. 78 - 79°C/0,2 mmHg.The 2,4,4-trimethyl-5-phenyl-3-heptanone can be obtained by alkylating diisopropyl ketone with 1-chloro-l-phenylpropane; Bp 78-79 ° C / 0.2 mmHg.
IR Spektrum : typische Banden bei 1705 cm-1 (stark).IR spectrum: typical bands at 1705 cm -1 (strong).
Durch die Zugabe von 50 Gewichtsteilen einer 10%-igen Lösung der bevorzugten Verbindung I (R = H) wirkt die entstehende Cologne-Base viel natürlicher. Die etwas camphrige Note des Bornylacetats, die man vorher wahrnahm, wird durch die Zugabe des Oximes zugedeckt. Gleichzeitig wird die Sandelnote von Sandalore noch hervorgehoben. Die neue Base wirkt zudem difussiver. Der mit der Zugabe des Oximes erzielte Effekt entspricht dem Effekt, der durch Zugabe eines Naturproduktes erzielt würde.By adding 50 parts by weight of a 10% solution of the preferred compound I (R = H), the resulting Cologne base appears much more natural. The slightly campy note of bornylacetate that was noticed before is covered by the addition of the oxime. At the same time, 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.
B. Wenn zu der Cologne-Komposition des Beispiels 2 A 50 Gewichtsteile einer l%-igen Lösung der Verbindung I (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.B. If 50 parts by weight of a 1% solution of the compound I (R = CH 3 ) in isopropyl myristate is added to the Cologne composition of Example 2 A, the resulting base looks fresher and greener. The camphoric note is covered and the petitgrain oil is emphasized, which gives the natural character of the resulting composition extraordinary.
Die Zugabe von 50 Gewichtsteilen einer 10%-igen Lösung von 2,2.4-Trimethyl-l-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.The addition of 50 parts by weight of a 10% solution of 2,2,4-trimethyl-1-phenyl-3-pentanone oxime in isopropyl myristate brings more freshness and more life to the above base. The phenolic, somewhat medicinal smell ver fades in favor of a minty, fresh one. light note. The spicy note becomes sharper, drier, more bitter. with a hint of black currants. The base is particularly suitable for men's perfumes.
Claims (7)
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WO2019076926A1 (en) * | 2017-10-17 | 2019-04-25 | S H Kelkar & Company Limited | Odorants and compositions comprising odorants |
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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 (en) | 2000-03-27 | 2001-10-02 | Takasago Internatl Corp | Aromatic bleaching agent composition |
CN1950320B (en) | 2004-05-13 | 2012-03-07 | 弗门尼舍有限公司 | Non-cyclic hindered ketones as perfuming ingredient |
US7494968B2 (en) * | 2004-05-13 | 2009-02-24 | Firmenich Sa | Non-cyclic hindered ketones as perfuming ingredient |
JP6248861B2 (en) * | 2014-08-19 | 2017-12-20 | 信越化学工業株式会社 | Chemically amplified resist material and pattern forming method |
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US4284814A (en) * | 1978-09-08 | 1981-08-18 | Hercules Incorporated | Propene trimer and propene tetramer and use thereof in perfumery |
EP0085352A2 (en) * | 1982-02-03 | 1983-08-10 | L. GIVAUDAN & CIE Société Anonyme | Unsaturated oximes, preparation thereof and use thereof as perfume and in the fragment compositions |
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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 |
JPS5913714A (en) * | 1982-07-13 | 1984-01-24 | Taito Pfizer Kk | Antiphlogistic and analgesic agent for external use |
-
1986
- 1986-01-27 US US06/822,978 patent/US4654169A/en not_active Expired - Lifetime
- 1986-01-30 EP EP86101178A patent/EP0191365B1/en not_active Expired
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US4284814A (en) * | 1978-09-08 | 1981-08-18 | Hercules Incorporated | Propene trimer and propene tetramer and use thereof in perfumery |
EP0085352A2 (en) * | 1982-02-03 | 1983-08-10 | L. GIVAUDAN & CIE Société Anonyme | Unsaturated oximes, preparation thereof and use thereof as perfume and in the fragment compositions |
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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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