JP5450076B2 - 新規なフレグランス化合物 - Google Patents
新規なフレグランス化合物 Download PDFInfo
- Publication number
- JP5450076B2 JP5450076B2 JP2009535109A JP2009535109A JP5450076B2 JP 5450076 B2 JP5450076 B2 JP 5450076B2 JP 2009535109 A JP2009535109 A JP 2009535109A JP 2009535109 A JP2009535109 A JP 2009535109A JP 5450076 B2 JP5450076 B2 JP 5450076B2
- Authority
- JP
- Japan
- Prior art keywords
- odor
- tert
- fragrance
- aldehyde
- mixture
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000003205 fragrance Substances 0.000 title claims description 45
- 150000001875 compounds Chemical class 0.000 title claims description 26
- 239000000203 mixture Substances 0.000 claims description 54
- 239000002304 perfume Substances 0.000 claims description 12
- 239000004615 ingredient Substances 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000000796 flavoring agent Substances 0.000 claims description 6
- 235000019634 flavors Nutrition 0.000 claims description 6
- 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 description 2
- 238000010276 construction Methods 0.000 claims 1
- 235000019645 odor Nutrition 0.000 description 55
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
- 150000001299 aldehydes Chemical class 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 239000000463 material Substances 0.000 description 21
- 239000000047 product Substances 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 21
- 239000012043 crude product Substances 0.000 description 19
- 238000010992 reflux Methods 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- -1 EP 368156) Chemical compound 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical class CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
- 235000019341 magnesium sulphate Nutrition 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- 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 11
- 229920006395 saturated elastomer Polymers 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 10
- 229940125904 compound 1 Drugs 0.000 description 10
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 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 8
- 239000012298 atmosphere Substances 0.000 description 8
- 239000012267 brine Substances 0.000 description 8
- 239000012074 organic phase 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
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- DXBXUMSLKADPEV-UHFFFAOYSA-N 3-(3-tert-butylcyclohexyl)propanal Chemical compound CC(C)(C)C1CCCC(CCC=O)C1 DXBXUMSLKADPEV-UHFFFAOYSA-N 0.000 description 6
- 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
- 241000255925 Diptera Species 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 150000001241 acetals Chemical class 0.000 description 6
- 239000012230 colorless oil Substances 0.000 description 6
- 239000004744 fabric 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
- 150000002825 nitriles Chemical class 0.000 description 6
- 229910052707 ruthenium Inorganic materials 0.000 description 6
- 239000002453 shampoo 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
- 241000402754 Erythranthe moschata Species 0.000 description 5
- 241000257303 Hymenoptera Species 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
- 239000000126 substance Substances 0.000 description 5
- 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 4
- VKHXHRZSJCTHEO-UHFFFAOYSA-N 3-(3-methylcyclohexyl)propanal Chemical compound CC1CCCC(CCC=O)C1 VKHXHRZSJCTHEO-UHFFFAOYSA-N 0.000 description 4
- 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 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- 241000755716 Convallaria Species 0.000 description 4
- 235000009046 Convallaria majalis Nutrition 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- 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
- 239000011734 sodium Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 239000001993 wax Substances 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
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 3
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 3
- XGNNVIWQJFIDMI-JXMROGBWSA-N (e)-2-methyl-3-(3-methylphenyl)prop-2-enal Chemical compound O=CC(/C)=C/C1=CC=CC(C)=C1 XGNNVIWQJFIDMI-JXMROGBWSA-N 0.000 description 3
- 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
- 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
- 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
- WAFRNWMAXUYZIW-UHFFFAOYSA-N 2-methylidene-3-(3-propan-2-ylcyclohexyl)butanal Chemical compound CC(C)C1CCCC(C(C)C(=C)C=O)C1 WAFRNWMAXUYZIW-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
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000207199 Citrus Species 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 206010019049 Hair texture abnormal Diseases 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-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
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- 238000004140 cleaning Methods 0.000 description 3
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- 239000002781 deodorant agent Substances 0.000 description 3
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 3
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- 229920005989 resin Polymers 0.000 description 1
- 239000012261 resinous substance Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 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
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000004753 textile Substances 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
- 239000000341 volatile oil Substances 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
- 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
- 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 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013147014A Division JP5635658B2 (ja) | 2006-11-04 | 2013-07-12 | 新規なフレグランス化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010508335A JP2010508335A (ja) | 2010-03-18 |
| JP2010508335A5 JP2010508335A5 (https=) | 2011-01-20 |
| JP5450076B2 true JP5450076B2 (ja) | 2014-03-26 |
Family
ID=37547376
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009535109A Expired - Fee Related JP5450076B2 (ja) | 2006-11-04 | 2007-10-18 | 新規なフレグランス化合物 |
| JP2013147014A Expired - Fee Related JP5635658B2 (ja) | 2006-11-04 | 2013-07-12 | 新規なフレグランス化合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013147014A Expired - Fee Related JP5635658B2 (ja) | 2006-11-04 | 2013-07-12 | 新規なフレグランス化合物 |
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 |
| BRPI0718676A2 (pt) | 2013-11-26 |
| 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 |
| MX2009004345A (es) | 2009-09-28 |
| CN104045535A (zh) | 2014-09-17 |
| GB0622037D0 (en) | 2006-12-13 |
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