BRPI0718676A2 - Compostos de fragrância - Google Patents
Compostos de fragrância Download PDFInfo
- Publication number
- BRPI0718676A2 BRPI0718676A2 BRPI0718676-2A BRPI0718676A BRPI0718676A2 BR PI0718676 A2 BRPI0718676 A2 BR PI0718676A2 BR PI0718676 A BRPI0718676 A BR PI0718676A BR PI0718676 A2 BRPI0718676 A2 BR PI0718676A2
- Authority
- BR
- Brazil
- Prior art keywords
- odor
- ppm
- nmr
- tert
- mhz
- Prior art date
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- 239000003205 fragrance Substances 0.000 title claims description 34
- 150000001875 compounds Chemical class 0.000 title claims description 26
- 239000002304 perfume Substances 0.000 claims description 24
- 239000004615 ingredient Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 235000019645 odor Nutrition 0.000 description 65
- 239000000203 mixture Substances 0.000 description 49
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- -1 aldehyde compounds Chemical class 0.000 description 29
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
- 238000005160 1H NMR spectroscopy Methods 0.000 description 26
- 239000000463 material Substances 0.000 description 26
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 23
- 238000005481 NMR spectroscopy Methods 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 150000001299 aldehydes Chemical class 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical class CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 20
- 239000012043 crude product Substances 0.000 description 19
- 238000010992 reflux Methods 0.000 description 19
- 239000000047 product Substances 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
- 235000019341 magnesium sulphate Nutrition 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- OHRBQTOZYGEWCJ-UHFFFAOYSA-N 3-(3-propan-2-ylphenyl)butanal Chemical compound CC(C)C1=CC=CC(C(C)CC=O)=C1 OHRBQTOZYGEWCJ-UHFFFAOYSA-N 0.000 description 11
- 229940125904 compound 1 Drugs 0.000 description 11
- 235000019439 ethyl acetate Nutrition 0.000 description 11
- SDQFDHOLCGWZPU-UHFFFAOYSA-N lilial Chemical compound O=CC(C)CC1=CC=C(C(C)(C)C)C=C1 SDQFDHOLCGWZPU-UHFFFAOYSA-N 0.000 description 10
- 239000006260 foam Substances 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 9
- DXBXUMSLKADPEV-UHFFFAOYSA-N 3-(3-tert-butylcyclohexyl)propanal Chemical compound CC(C)(C)C1CCCC(CCC=O)C1 DXBXUMSLKADPEV-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 239000012267 brine Substances 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 239000000344 soap Substances 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- 241000255925 Diptera Species 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 6
- 239000012230 colorless oil Substances 0.000 description 6
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000002453 shampoo Substances 0.000 description 6
- 239000001993 wax Substances 0.000 description 6
- ALTOPVKWXXMARN-UHFFFAOYSA-N 2-methyl-3-(3-methylcyclohexyl)propanal Chemical compound O=CC(C)CC1CCCC(C)C1 ALTOPVKWXXMARN-UHFFFAOYSA-N 0.000 description 5
- ONLLYVFPLBWUGS-UHFFFAOYSA-N 3-(3-propan-2-ylcyclohexyl)butanal Chemical compound CC(C)C1CCCC(C(C)CC=O)C1 ONLLYVFPLBWUGS-UHFFFAOYSA-N 0.000 description 5
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 5
- 230000001580 bacterial effect Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- 239000000796 flavoring agent Substances 0.000 description 5
- 235000019634 flavors Nutrition 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- 229910052707 ruthenium Inorganic materials 0.000 description 5
- VKHXHRZSJCTHEO-UHFFFAOYSA-N 3-(3-methylcyclohexyl)propanal Chemical compound CC1CCCC(CCC=O)C1 VKHXHRZSJCTHEO-UHFFFAOYSA-N 0.000 description 4
- 241000207199 Citrus Species 0.000 description 4
- 244000068485 Convallaria majalis Species 0.000 description 4
- 235000009046 Convallaria majalis Nutrition 0.000 description 4
- 241000257303 Hymenoptera Species 0.000 description 4
- 241000234435 Lilium Species 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 4
- 150000001241 acetals Chemical class 0.000 description 4
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 235000020971 citrus fruits Nutrition 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 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 4
- QEISRFVBPFFHKI-UHFFFAOYSA-N 1-(1-bromoethyl)-3-tert-butylbenzene Chemical compound CC(Br)C1=CC=CC(C(C)(C)C)=C1 QEISRFVBPFFHKI-UHFFFAOYSA-N 0.000 description 3
- SMSKIVCCLIQXFD-UHFFFAOYSA-N 1-tert-butyl-3-ethenylbenzene Chemical compound CC(C)(C)C1=CC=CC(C=C)=C1 SMSKIVCCLIQXFD-UHFFFAOYSA-N 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- QTEJXYSAAVQIET-UHFFFAOYSA-N 2,2-dimethyl-3-(3-methylcyclohexyl)propan-1-ol Chemical compound CC1CCCC(CC(C)(C)CO)C1 QTEJXYSAAVQIET-UHFFFAOYSA-N 0.000 description 3
- APRIJBGPADMXGB-UHFFFAOYSA-N 2,2-dimethyl-3-(3-methylcyclohexyl)propanal Chemical compound CC1CCCC(CC(C)(C)C=O)C1 APRIJBGPADMXGB-UHFFFAOYSA-N 0.000 description 3
- YMKXBKYGYOKCPB-UHFFFAOYSA-N 2-[2-(3-propan-2-ylcyclohexyl)propyl]-1,3-dioxolane Chemical compound C1C(C(C)C)CCCC1C(C)CC1OCCO1 YMKXBKYGYOKCPB-UHFFFAOYSA-N 0.000 description 3
- NUDUZUTWNUBMIB-UHFFFAOYSA-N 2-[2-(3-propan-2-ylphenyl)propyl]-1,3-dioxolane Chemical compound CC(C)C1=CC=CC(C(C)CC2OCCO2)=C1 NUDUZUTWNUBMIB-UHFFFAOYSA-N 0.000 description 3
- ARSQZAOWGIARAE-UHFFFAOYSA-N 2-[2-(3-tert-butylcyclohexyl)ethyl]-1,3-dioxolane Chemical compound C1C(C(C)(C)C)CCCC1CCC1OCCO1 ARSQZAOWGIARAE-UHFFFAOYSA-N 0.000 description 3
- SPEXRACZSGHLPK-UHFFFAOYSA-N 2-methyl-3-(3-methylcyclohexyl)propan-1-ol Chemical compound OCC(C)CC1CCCC(C)C1 SPEXRACZSGHLPK-UHFFFAOYSA-N 0.000 description 3
- DSPGGRWNWOKXDF-UHFFFAOYSA-N 2-methyl-3-(3-propan-2-ylcyclohexyl)butanal Chemical compound CC(C)C1CCCC(C(C)C(C)C=O)C1 DSPGGRWNWOKXDF-UHFFFAOYSA-N 0.000 description 3
- HURQJMQJQXLCJE-UHFFFAOYSA-N 3-(3-methylcyclohexyl)butan-1-ol Chemical compound OCCC(C)C1CCCC(C)C1 HURQJMQJQXLCJE-UHFFFAOYSA-N 0.000 description 3
- DBOHOOKUJUYJBX-UHFFFAOYSA-N 3-(3-methylphenyl)butanal Chemical compound O=CCC(C)C1=CC=CC(C)=C1 DBOHOOKUJUYJBX-UHFFFAOYSA-N 0.000 description 3
- XOLUVZDRTOUNIX-UHFFFAOYSA-N 3-(3-tert-butylcyclohexyl)butan-1-ol Chemical compound OCCC(C)C1CCCC(C(C)(C)C)C1 XOLUVZDRTOUNIX-UHFFFAOYSA-N 0.000 description 3
- GUYMQPQFTASCQZ-UHFFFAOYSA-N 3-(3-tert-butylcyclohexyl)butanal Chemical compound O=CCC(C)C1CCCC(C(C)(C)C)C1 GUYMQPQFTASCQZ-UHFFFAOYSA-N 0.000 description 3
- GFQYFEXOXNYSAS-UHFFFAOYSA-N 3-(3-tert-butylphenyl)butanal Chemical compound O=CCC(C)C1=CC=CC(C(C)(C)C)=C1 GFQYFEXOXNYSAS-UHFFFAOYSA-N 0.000 description 3
- APFNXQQLJSEQBM-UHFFFAOYSA-N 3-(3-tert-butylphenyl)propanal Chemical compound CC(C)(C)C1=CC=CC(CCC=O)=C1 APFNXQQLJSEQBM-UHFFFAOYSA-N 0.000 description 3
- WSNKEJIFARPOSQ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-(1-benzothiophen-2-ylmethyl)benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCC2=CC3=C(S2)C=CC=C3)C=CC=1 WSNKEJIFARPOSQ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- FZJUFJKVIYFBSY-UHFFFAOYSA-N bourgeonal Chemical compound CC(C)(C)C1=CC=C(CCC=O)C=C1 FZJUFJKVIYFBSY-UHFFFAOYSA-N 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
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- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000012437 perfumed product Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical compound ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical class CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 235000002020 sage Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 230000008786 sensory perception of smell Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- POECFFCNUXZPJT-UHFFFAOYSA-M sodium;carbonic acid;hydrogen carbonate Chemical compound [Na+].OC(O)=O.OC([O-])=O POECFFCNUXZPJT-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000001069 triethyl citrate Substances 0.000 description 1
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 229940117960 vanillin Drugs 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
- 239000000341 volatile oil Substances 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
-
- 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
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/14—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the side-chain of aromatic compounds
-
- 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
- C07C47/228—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde
-
- 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
- C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0622037.0A GB0622037D0 (en) | 2006-11-04 | 2006-11-04 | Novel fragrance compounds |
| GB0622037.0 | 2006-11-04 | ||
| PCT/GB2007/003961 WO2008053148A1 (en) | 2006-11-04 | 2007-10-18 | Novel fragrance compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BRPI0718676A2 true BRPI0718676A2 (pt) | 2013-11-26 |
Family
ID=37547376
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0718676-2A BRPI0718676A2 (pt) | 2006-11-04 | 2007-10-18 | Compostos de fragrância |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US8709994B2 (https=) |
| EP (2) | EP2657218B1 (https=) |
| JP (2) | JP5450076B2 (https=) |
| CN (2) | CN104045535A (https=) |
| BR (1) | BRPI0718676A2 (https=) |
| ES (1) | ES2449768T3 (https=) |
| GB (1) | GB0622037D0 (https=) |
| MX (1) | MX2009004345A (https=) |
| WO (1) | WO2008053148A1 (https=) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7511001B2 (en) * | 2007-07-31 | 2009-03-31 | International Flavors & Fragrances Inc. | Substituted cyclohexyl propanal compounds and their use in perfume compositions |
| US20100256421A1 (en) * | 2009-03-23 | 2010-10-07 | O'laughlin Industries, Co. Ltd. | Propanal Production Methods |
| WO2011048068A2 (de) | 2009-10-23 | 2011-04-28 | Basf Se | Verfahren zur herstellung m-substituierter phenylalkanole durch isomerisierung |
| CN102574757B (zh) | 2009-10-23 | 2015-12-02 | 巴斯夫欧洲公司 | 通过烷基化制备间-或对取代苯基链烷醇的方法 |
| US7834219B1 (en) * | 2009-11-16 | 2010-11-16 | International Flavors & Fragrances Inc. | 4-alkyl cyclohexanepropanal compounds and their use in perfume compositions |
| US8188023B2 (en) * | 2009-11-16 | 2012-05-29 | International Flavors & Fragrances Inc. | 4-alkyl cyclohexanepropanal compounds and their use in perfume compositions |
| US9187709B2 (en) * | 2010-08-25 | 2015-11-17 | Kedar Ramesh Vaze | Synthesis of a novel odorant |
| JP5626987B2 (ja) | 2010-12-28 | 2014-11-19 | 三菱瓦斯化学株式会社 | 新規脂環式アルコール |
| CN103796980B (zh) * | 2011-09-16 | 2016-08-31 | 巴斯夫欧洲公司 | 制备4-环己基-2-甲基-2-丁醇的方法 |
| JP5921226B2 (ja) * | 2012-02-02 | 2016-05-24 | 花王株式会社 | ミューゲ香料素材の探索方法 |
| GB2528467A (en) * | 2014-07-22 | 2016-01-27 | Givaudan Sa | Organic compounds |
| ES2734408T3 (es) * | 2015-07-14 | 2019-12-05 | Firmenich & Cie | Compuesto que tiene olor de lirio del valle |
| BR112018004991B1 (pt) | 2015-09-16 | 2021-06-22 | Firmenich S.A. | Ingrediente aromatizante de lírio verde do vale |
| JP2020505500A (ja) * | 2017-01-18 | 2020-02-20 | フイルメニツヒ ソシエテ アノニムＦｉｒｍｅｎｉｃｈ Ｓａ | ミュゲ香気を有する組成物 |
| SG11202001226PA (en) | 2017-12-21 | 2020-03-30 | Firmenich & Cie | Method for identifying positive allosteric modulators for odorant receptors |
| EP3880777B1 (en) | 2018-11-13 | 2025-06-25 | Symrise AG | Perfuming ingredients with lily of the valley note |
| BR112021008699A2 (pt) | 2018-12-19 | 2021-08-10 | Firmenich S/A | uso de compostos voláteis para modular a percepção de floral muguet |
| US20250122140A1 (en) * | 2021-09-01 | 2025-04-17 | Miltitz Aromatics Gmbh | Novel cyclic compounds, and use thereof as perfumes |
| EP4447678A1 (en) * | 2022-01-18 | 2024-10-23 | Firmenich SA | Arthropod control compositions |
| CN115028512B (zh) * | 2022-06-27 | 2023-09-19 | 万华化学集团股份有限公司 | 一种由3-甲基苯甲醛合成美妍醇的方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4835065B1 (https=) * | 1969-12-26 | 1973-10-25 | ||
| JPS4918228B2 (https=) * | 1971-09-08 | 1974-05-08 | ||
| US4604232A (en) * | 1985-03-15 | 1986-08-05 | International Flavors & Fragrances Inc. | Methyl-substituted cyclohexenyl acetaldehydes, organoleptic uses thereof, processes for producing same and intermediates useful therein |
| ES2144067T3 (es) * | 1994-05-31 | 2000-06-01 | Firmenich & Cie | Nuevos compuestos aromaticos y utilizacion de los mismos en perfumeria. |
| DE19714042A1 (de) * | 1997-04-05 | 1998-10-08 | Henkel Kgaa | Verfahren zur Herstellung aromatischer Aldehyde |
| DE19820657A1 (de) * | 1998-05-08 | 1999-11-11 | Henkel Kgaa | Riechstoff-Zusammensetzungen |
| DE60013353T2 (de) * | 1999-05-19 | 2005-09-08 | Firmenich S.A. | Anwendung von substituierten Acetaldehyden mit einem cyclischen Substituent als Riechstoffbestandteile |
| DE10026004A1 (de) * | 2000-05-25 | 2001-11-29 | Cognis Deutschland Gmbh | 3,3-Dimethylcyclohexan-Derivate |
| EP1677789A1 (en) * | 2003-10-31 | 2006-07-12 | AstraZeneca AB | Alkynes i |
| US7511001B2 (en) * | 2007-07-31 | 2009-03-31 | International Flavors & Fragrances Inc. | Substituted cyclohexyl propanal compounds and their use in perfume compositions |
-
2006
- 2006-11-04 GB GBGB0622037.0A patent/GB0622037D0/en not_active Ceased
-
2007
- 2007-10-18 EP EP13171301.8A patent/EP2657218B1/en not_active Not-in-force
- 2007-10-18 EP EP07824211.2A patent/EP2077986B1/en not_active Not-in-force
- 2007-10-18 WO PCT/GB2007/003961 patent/WO2008053148A1/en not_active Ceased
- 2007-10-18 BR BRPI0718676-2A patent/BRPI0718676A2/pt active Search and Examination
- 2007-10-18 JP JP2009535109A patent/JP5450076B2/ja not_active Expired - Fee Related
- 2007-10-18 US US12/513,311 patent/US8709994B2/en not_active Expired - Fee Related
- 2007-10-18 ES ES07824211.2T patent/ES2449768T3/es active Active
- 2007-10-18 CN CN201410295231.XA patent/CN104045535A/zh active Pending
- 2007-10-18 CN CN200780040965.1A patent/CN101535232B/zh not_active Expired - Fee Related
- 2007-10-18 MX MX2009004345A patent/MX2009004345A/es active IP Right Grant
-
2013
- 2013-07-12 JP JP2013147014A patent/JP5635658B2/ja not_active Expired - Fee Related
- 2013-12-02 US US14/094,199 patent/US20140142343A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JP2013241430A (ja) | 2013-12-05 |
| ES2449768T3 (es) | 2014-03-21 |
| JP5635658B2 (ja) | 2014-12-03 |
| EP2657218A1 (en) | 2013-10-30 |
| JP2010508335A (ja) | 2010-03-18 |
| WO2008053148A1 (en) | 2008-05-08 |
| CN101535232B (zh) | 2016-05-11 |
| CN101535232A (zh) | 2009-09-16 |
| EP2077986A1 (en) | 2009-07-15 |
| EP2657218B1 (en) | 2017-07-26 |
| US20140142343A1 (en) | 2014-05-22 |
| US20100069287A1 (en) | 2010-03-18 |
| US8709994B2 (en) | 2014-04-29 |
| EP2077986B1 (en) | 2013-12-04 |
| JP5450076B2 (ja) | 2014-03-26 |
| MX2009004345A (es) | 2009-09-28 |
| CN104045535A (zh) | 2014-09-17 |
| GB0622037D0 (en) | 2006-12-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B07A | Application suspended after technical examination (opinion) [chapter 7.1 patent gazette] | ||
| B25A | Requested transfer of rights approved |
Owner name: GIVAUDAN S.A. (CH) |
|
| B09A | Decision: intention to grant [chapter 9.1 patent gazette] | ||
| B11D | Dismissal acc. art. 38, par 2 of ipl - failure to pay fee after grant in time |