RU2535784C2 - Новые альдегиды и нитрилы, получаемые из изофорона, и их применение в парфюмерии - Google Patents
Новые альдегиды и нитрилы, получаемые из изофорона, и их применение в парфюмерии Download PDFInfo
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- RU2535784C2 RU2535784C2 RU2012115458/04A RU2012115458A RU2535784C2 RU 2535784 C2 RU2535784 C2 RU 2535784C2 RU 2012115458/04 A RU2012115458/04 A RU 2012115458/04A RU 2012115458 A RU2012115458 A RU 2012115458A RU 2535784 C2 RU2535784 C2 RU 2535784C2
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- formula
- hydrogen atom
- alkyl
- compounds
- compound
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- 150000001299 aldehydes Chemical class 0.000 title description 10
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 title description 10
- 150000002825 nitriles Chemical class 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 84
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 50
- 239000000203 mixture Substances 0.000 claims abstract description 46
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 21
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 9
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 5
- -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 239000002304 perfume Substances 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 15
- 239000004615 ingredient Substances 0.000 claims description 5
- 230000000873 masking effect Effects 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- 238000005160 1H NMR spectroscopy Methods 0.000 description 16
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 13
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- 239000002585 base Substances 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical class O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 239000012429 reaction media Substances 0.000 description 9
- MMDJLQPXLITQBV-UHFFFAOYSA-N 2-(2,4,4-trimethylcyclopentyl)prop-2-enenitrile Chemical compound CC1CC(C)(C)CC1C(=C)C#N MMDJLQPXLITQBV-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- 229940125898 compound 5 Drugs 0.000 description 7
- 239000002537 cosmetic Substances 0.000 description 7
- 239000006071 cream Substances 0.000 description 7
- 239000003599 detergent Substances 0.000 description 7
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 7
- 239000000344 soap Substances 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 6
- 239000012876 carrier material Substances 0.000 description 6
- 235000020971 citrus fruits Nutrition 0.000 description 6
- 239000002781 deodorant agent Substances 0.000 description 6
- 239000000499 gel Substances 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 239000006210 lotion Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000002453 shampoo Substances 0.000 description 6
- ZJBQGPQMYURWAU-UHFFFAOYSA-N 2-(3,3,5-trimethylcyclopenten-1-yl)acetonitrile Chemical compound CC1CC(C)(C)C=C1CC#N ZJBQGPQMYURWAU-UHFFFAOYSA-N 0.000 description 5
- 241000207199 Citrus Species 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- OWKNBTVQGGTTEI-UHFFFAOYSA-N 2-(2,4,4-trimethylcyclopenten-1-yl)acetonitrile Chemical compound CC1=C(CC#N)CC(C)(C)C1 OWKNBTVQGGTTEI-UHFFFAOYSA-N 0.000 description 4
- CGZTVBYESYRPON-UHFFFAOYSA-N 2-(2,4,4-trimethylcyclopentyl)acetonitrile Chemical compound CC1CC(C)(C)CC1CC#N CGZTVBYESYRPON-UHFFFAOYSA-N 0.000 description 4
- VPNUNBAFCAOPQM-UHFFFAOYSA-N 2-(2,4,4-trimethylcyclopentyl)propanenitrile Chemical compound N#CC(C)C1CC(C)(C)CC1C VPNUNBAFCAOPQM-UHFFFAOYSA-N 0.000 description 4
- CSISIDNSBDDZDK-UHFFFAOYSA-N 2-(2,4,4-trimethylcyclopentylidene)acetonitrile Chemical compound CC1CC(C)(C)CC1=CC#N CSISIDNSBDDZDK-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000003974 emollient agent Substances 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 235000019645 odor Nutrition 0.000 description 4
- OSGVUJIYGVKCQV-UHFFFAOYSA-N 2-(2,4,4-trimethylcyclopentyl)acetaldehyde Chemical compound CC1CC(C)(C)CC1CC=O OSGVUJIYGVKCQV-UHFFFAOYSA-N 0.000 description 3
- XGCRJUQYBCDAEW-UHFFFAOYSA-N 2-(2,4,4-trimethylcyclopentyl)prop-2-enal Chemical compound CC1CC(C)(C)CC1C(=C)C=O XGCRJUQYBCDAEW-UHFFFAOYSA-N 0.000 description 3
- MIGLSAUGGYMUTK-UHFFFAOYSA-N 2-(2,4,4-trimethylcyclopentyl)propanal Chemical compound O=CC(C)C1CC(C)(C)CC1C MIGLSAUGGYMUTK-UHFFFAOYSA-N 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 235000005979 Citrus limon Nutrition 0.000 description 3
- 244000131522 Citrus pyriformis Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- 230000001166 anti-perspirative effect Effects 0.000 description 3
- 239000003213 antiperspirant Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 3
- 239000002324 mouth wash Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000000606 toothpaste Substances 0.000 description 3
- OBKHYUIZSOIEPG-UHFFFAOYSA-N 1,1,3-trimethylcyclopentane Chemical class CC1CCC(C)(C)C1 OBKHYUIZSOIEPG-UHFFFAOYSA-N 0.000 description 2
- SCZNXLWKYFICFV-UHFFFAOYSA-N 1,2,3,4,5,7,8,9-octahydropyrido[1,2-b]diazepine Chemical compound C1CCCNN2CCCC=C21 SCZNXLWKYFICFV-UHFFFAOYSA-N 0.000 description 2
- OXTQEWUBDTVSFB-UHFFFAOYSA-N 2,4,4-Trimethylcyclopentanone Chemical compound CC1CC(C)(C)CC1=O OXTQEWUBDTVSFB-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- FZAHLQFUZFLPAC-UHFFFAOYSA-N 3-hydroxy-2-(2,4,4-trimethylcyclopentyl)propanenitrile Chemical compound CC1CC(C)(C)CC1C(CO)C#N FZAHLQFUZFLPAC-UHFFFAOYSA-N 0.000 description 2
- ROTNQFPVXVZSRL-UHFFFAOYSA-N 4,4,6-trimethyl-7-oxabicyclo[4.1.0]heptan-2-one Chemical compound C1C(C)(C)CC(=O)C2OC21C ROTNQFPVXVZSRL-UHFFFAOYSA-N 0.000 description 2
- NXJCRELRQHZBQA-UHFFFAOYSA-N 5,7-dimethoxy-1-benzopyran-2-one Chemical compound C1=CC(=O)OC2=CC(OC)=CC(OC)=C21 NXJCRELRQHZBQA-UHFFFAOYSA-N 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- 244000144730 Amygdalus persica Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 240000000467 Carum carvi Species 0.000 description 2
- 235000005747 Carum carvi Nutrition 0.000 description 2
- 229920000858 Cyclodextrin Polymers 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- YIKYNHJUKRTCJL-UHFFFAOYSA-N Ethyl maltol Chemical compound CCC=1OC=CC(=O)C=1O YIKYNHJUKRTCJL-UHFFFAOYSA-N 0.000 description 2
- 229920002774 Maltodextrin Polymers 0.000 description 2
- 235000006040 Prunus persica var persica Nutrition 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 229940043376 ammonium acetate Drugs 0.000 description 2
- 235000019257 ammonium acetate Nutrition 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 2
- JOZKFWLRHCDGJA-UHFFFAOYSA-N citronellol acetate Chemical compound CC(=O)OCCC(C)CCC=C(C)C JOZKFWLRHCDGJA-UHFFFAOYSA-N 0.000 description 2
- 229940097362 cyclodextrins Drugs 0.000 description 2
- 238000006114 decarboxylation reaction Methods 0.000 description 2
- 229940093503 ethyl maltol Drugs 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- IFYYFLINQYPWGJ-UHFFFAOYSA-N gamma-decalactone Chemical compound CCCCCCC1CCC(=O)O1 IFYYFLINQYPWGJ-UHFFFAOYSA-N 0.000 description 2
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 2
- 229920000591 gum Polymers 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- BNKVBGGOHZGTHC-UHFFFAOYSA-N methyl 2-cyano-2-(2,4,4-trimethylcyclopentylidene)acetate Chemical compound COC(=O)C(C#N)=C1CC(C)(C)CC1C BNKVBGGOHZGTHC-UHFFFAOYSA-N 0.000 description 2
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
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- 229940034610 toothpaste Drugs 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- QRPLZGZHJABGRS-UHFFFAOYSA-N xi-5-Dodecanolide Chemical compound CCCCCCCC1CCCC(=O)O1 QRPLZGZHJABGRS-UHFFFAOYSA-N 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 1
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- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
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- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
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- 150000001351 alkyl iodides Chemical class 0.000 description 1
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- 230000008030 elimination Effects 0.000 description 1
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- 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
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- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- UFLHIIWVXFIJGU-UHFFFAOYSA-N hex-3-en-1-ol Natural products CCC=CCCO UFLHIIWVXFIJGU-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- ANGDWNBGPBMQHW-UHFFFAOYSA-N methyl cyanoacetate Chemical compound COC(=O)CC#N ANGDWNBGPBMQHW-UHFFFAOYSA-N 0.000 description 1
- NVLSIZITFJRWPY-ONEGZZNKSA-N n,n-dimethyl-4-[(e)-2-(4-nitrophenyl)ethenyl]aniline Chemical compound C1=CC(N(C)C)=CC=C1\C=C\C1=CC=C([N+]([O-])=O)C=C1 NVLSIZITFJRWPY-ONEGZZNKSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 235000019615 sensations Nutrition 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 235000019565 spicy aroma Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UHUFTBALEZWWIH-UHFFFAOYSA-N tetradecanal Chemical compound CCCCCCCCCCCCCC=O UHUFTBALEZWWIH-UHFFFAOYSA-N 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
- C07C47/105—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing rings
- C07C47/11—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing rings monocyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/31—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/225—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/003—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing less than six carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0956422 | 2009-09-18 | ||
| FR0956422A FR2950342B1 (fr) | 2009-09-18 | 2009-09-18 | Nouveaux aldehydes et nitriles issus de l'isophorone, ainsi que leur utilisation en parfumerie |
| PCT/IB2010/054213 WO2011033479A1 (fr) | 2009-09-18 | 2010-09-17 | Nouveaux aldehydes et nitriles issus de l'isophorone, ainsi que leur utilisation en parfumerie |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2012115458A RU2012115458A (ru) | 2013-10-27 |
| RU2535784C2 true RU2535784C2 (ru) | 2014-12-20 |
Family
ID=41683039
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2012115458/04A RU2535784C2 (ru) | 2009-09-18 | 2010-09-17 | Новые альдегиды и нитрилы, получаемые из изофорона, и их применение в парфюмерии |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US8592360B2 (https=) |
| EP (1) | EP2477595B1 (https=) |
| JP (1) | JP5856564B2 (https=) |
| CN (1) | CN102573767B (https=) |
| BR (1) | BR112012006108A2 (https=) |
| CA (1) | CA2773226C (https=) |
| DK (1) | DK2477595T3 (https=) |
| ES (1) | ES2549914T3 (https=) |
| FR (1) | FR2950342B1 (https=) |
| IN (1) | IN2012DN02264A (https=) |
| MX (1) | MX2012003326A (https=) |
| PL (1) | PL2477595T3 (https=) |
| PT (1) | PT2477595E (https=) |
| RU (1) | RU2535784C2 (https=) |
| WO (1) | WO2011033479A1 (https=) |
| ZA (1) | ZA201201673B (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102675074A (zh) * | 2012-05-25 | 2012-09-19 | 江西华士药业有限公司 | 环丙唑醇关键中间体1-(4-氯苯基)-2-环丙基-1-丙酮的制备方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4477683A (en) * | 1982-05-03 | 1984-10-16 | Givaudan Corporation | 3-Methyl-1-(2,3,4-and 2,4,4-trimethyl-1-cyclopentylidene) pent-2-en-4-one and isomers, and perfume compositions thereof |
| US5073538A (en) * | 1989-08-26 | 1991-12-17 | Basf Aktiengesellschaft | Cycloalkylidene derivatives and fragrance composition |
| RU2288910C2 (ru) * | 2001-10-23 | 2006-12-10 | В. Ман Фис | Новые производные норборнана и норборнена, их применение и содержащие их ароматные продукты |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3931143A (en) | 1967-02-15 | 1976-01-06 | Pennwalt Corporation | Unsymmetrical aliphatic monoazo compounds |
| DE3345375A1 (de) | 1983-12-15 | 1985-06-27 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von 4-substituierten but-3-en-l-carbonsaeuren und von deren estern |
| DE3726418A1 (de) * | 1987-08-07 | 1989-02-16 | Dragoco Gerberding Co Gmbh | Verwendung von campholennitrilen als riechstoff |
-
2009
- 2009-09-18 FR FR0956422A patent/FR2950342B1/fr active Active
-
2010
- 2010-09-17 BR BR112012006108A patent/BR112012006108A2/pt active IP Right Grant
- 2010-09-17 RU RU2012115458/04A patent/RU2535784C2/ru active
- 2010-09-17 US US13/496,783 patent/US8592360B2/en active Active
- 2010-09-17 IN IN2264DEN2012 patent/IN2012DN02264A/en unknown
- 2010-09-17 EP EP10763445.3A patent/EP2477595B1/fr active Active
- 2010-09-17 ES ES10763445.3T patent/ES2549914T3/es active Active
- 2010-09-17 DK DK10763445.3T patent/DK2477595T3/en active
- 2010-09-17 PT PT107634453T patent/PT2477595E/pt unknown
- 2010-09-17 JP JP2012529394A patent/JP5856564B2/ja active Active
- 2010-09-17 PL PL10763445T patent/PL2477595T3/pl unknown
- 2010-09-17 MX MX2012003326A patent/MX2012003326A/es active IP Right Grant
- 2010-09-17 WO PCT/IB2010/054213 patent/WO2011033479A1/fr not_active Ceased
- 2010-09-17 CA CA2773226A patent/CA2773226C/fr active Active
- 2010-09-17 CN CN201080041627.1A patent/CN102573767B/zh active Active
-
2012
- 2012-03-07 ZA ZA2012/01673A patent/ZA201201673B/en unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4477683A (en) * | 1982-05-03 | 1984-10-16 | Givaudan Corporation | 3-Methyl-1-(2,3,4-and 2,4,4-trimethyl-1-cyclopentylidene) pent-2-en-4-one and isomers, and perfume compositions thereof |
| US5073538A (en) * | 1989-08-26 | 1991-12-17 | Basf Aktiengesellschaft | Cycloalkylidene derivatives and fragrance composition |
| RU2288910C2 (ru) * | 2001-10-23 | 2006-12-10 | В. Ман Фис | Новые производные норборнана и норборнена, их применение и содержащие их ароматные продукты |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2013505229A (ja) | 2013-02-14 |
| BR112012006108A2 (pt) | 2016-06-07 |
| IN2012DN02264A (https=) | 2015-08-21 |
| US8592360B2 (en) | 2013-11-26 |
| CN102573767B (zh) | 2014-02-26 |
| JP5856564B2 (ja) | 2016-02-10 |
| US20120238486A1 (en) | 2012-09-20 |
| PL2477595T3 (pl) | 2016-01-29 |
| ES2549914T3 (es) | 2015-11-03 |
| WO2011033479A1 (fr) | 2011-03-24 |
| CN102573767A (zh) | 2012-07-11 |
| DK2477595T3 (en) | 2015-10-26 |
| EP2477595A1 (fr) | 2012-07-25 |
| CA2773226A1 (fr) | 2011-03-24 |
| RU2012115458A (ru) | 2013-10-27 |
| HK1169947A1 (zh) | 2013-02-15 |
| MX2012003326A (es) | 2012-04-30 |
| PT2477595E (pt) | 2015-11-02 |
| ZA201201673B (en) | 2012-10-31 |
| EP2477595B1 (fr) | 2015-07-22 |
| FR2950342B1 (fr) | 2011-09-02 |
| FR2950342A1 (fr) | 2011-03-25 |
| CA2773226C (fr) | 2017-10-31 |
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