ES2373271T3 - Compuestos orgánicos. - Google Patents
Compuestos orgánicos. Download PDFInfo
- Publication number
- ES2373271T3 ES2373271T3 ES09711211T ES09711211T ES2373271T3 ES 2373271 T3 ES2373271 T3 ES 2373271T3 ES 09711211 T ES09711211 T ES 09711211T ES 09711211 T ES09711211 T ES 09711211T ES 2373271 T3 ES2373271 T3 ES 2373271T3
- Authority
- ES
- Spain
- Prior art keywords
- trimethylcyclopent
- enyl
- methyl
- green
- formula
- 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.)
- Active
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- 150000002894 organic compounds Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 46
- 239000003205 fragrance Substances 0.000 claims abstract description 26
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 10
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 5
- 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 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 3
- 239000000203 mixture Substances 0.000 claims description 30
- CPKXZNAVHRUIPH-UHFFFAOYSA-N 1-(2,2,3-trimethylcyclopent-3-en-1-yl)ethanol Chemical compound CC(O)C1CC=C(C)C1(C)C CPKXZNAVHRUIPH-UHFFFAOYSA-N 0.000 claims description 9
- HHZSLSRWAVPAFD-UHFFFAOYSA-N 2,2,3-trimethylcyclopentane-1-carbaldehyde Chemical compound CC1CCC(C=O)C1(C)C HHZSLSRWAVPAFD-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- OAOMPGIZMZXHLU-UHFFFAOYSA-N 1-(2,2,3-trimethylcyclopent-3-en-1-yl)propan-1-ol Chemical compound CCC(O)C1CC=C(C)C1(C)C OAOMPGIZMZXHLU-UHFFFAOYSA-N 0.000 claims description 5
- QNTPKYVXKBAWTC-UHFFFAOYSA-N 1-(2,2,3-trimethylcyclopent-3-en-1-yl)prop-2-en-1-ol Chemical compound CC1=CCC(C(O)C=C)C1(C)C QNTPKYVXKBAWTC-UHFFFAOYSA-N 0.000 claims description 4
- 239000002537 cosmetic Substances 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- XYPXBNQYFAFAMV-UHFFFAOYSA-N 1-(2,2,3-trimethylcyclopent-3-en-1-yl)but-3-en-1-one Chemical compound CC1=CCC(C(=O)CC=C)C1(C)C XYPXBNQYFAFAMV-UHFFFAOYSA-N 0.000 claims description 3
- FYTFEEDOWPNSJS-UHFFFAOYSA-N 1-(2,2,3-trimethylcyclopent-3-en-1-yl)propan-1-one Chemical compound CCC(=O)C1CC=C(C)C1(C)C FYTFEEDOWPNSJS-UHFFFAOYSA-N 0.000 claims description 3
- YQSAQFVWVQBMGL-UHFFFAOYSA-N 2-(2,2,3-trimethylcyclopent-3-en-1-yl)butan-2-ol Chemical compound CCC(C)(O)C1CC=C(C)C1(C)C YQSAQFVWVQBMGL-UHFFFAOYSA-N 0.000 claims description 3
- JMUBOBUZNRGCTJ-UHFFFAOYSA-N 2-methyl-1-(2,2,3-trimethylcyclopentyl)prop-2-en-1-ol Chemical compound CC1CCC(C(O)C(C)=C)C1(C)C JMUBOBUZNRGCTJ-UHFFFAOYSA-N 0.000 claims description 3
- BPHWXNLRLXYMGB-UHFFFAOYSA-N 3-methyl-1-(2,2,3-trimethylcyclopentyl)butan-1-ol Chemical compound CC(C)CC(O)C1CCC(C)C1(C)C BPHWXNLRLXYMGB-UHFFFAOYSA-N 0.000 claims description 3
- WPRDGOGWJNKEHH-UHFFFAOYSA-N 3-methyl-1-(2,2,3-trimethylcyclopentyl)butan-1-one Chemical compound CC(C)CC(=O)C1CCC(C)C1(C)C WPRDGOGWJNKEHH-UHFFFAOYSA-N 0.000 claims description 3
- ZZOAFVYNKNKPJG-UHFFFAOYSA-N 6-methyl-4-(2,2,3-trimethylcyclopentyl)hept-1-en-4-ol Chemical compound CC(C)CC(O)(CC=C)C1CCC(C)C1(C)C ZZOAFVYNKNKPJG-UHFFFAOYSA-N 0.000 claims description 3
- HYMPODQLPOYLTG-AATRIKPKSA-N (e)-1-(2,2,3-trimethylcyclopent-3-en-1-yl)but-2-en-1-ol Chemical compound C\C=C\C(O)C1CC=C(C)C1(C)C HYMPODQLPOYLTG-AATRIKPKSA-N 0.000 claims description 2
- GFBOMJGZLJHLMT-AATRIKPKSA-N (e)-1-(2,2,3-trimethylcyclopent-3-en-1-yl)but-2-en-1-one Chemical compound C\C=C\C(=O)C1CC=C(C)C1(C)C GFBOMJGZLJHLMT-AATRIKPKSA-N 0.000 claims description 2
- HYMPODQLPOYLTG-WAYWQWQTSA-N (z)-1-(2,2,3-trimethylcyclopent-3-en-1-yl)but-2-en-1-ol Chemical compound C\C=C/C(O)C1CC=C(C)C1(C)C HYMPODQLPOYLTG-WAYWQWQTSA-N 0.000 claims description 2
- GFBOMJGZLJHLMT-WAYWQWQTSA-N (z)-1-(2,2,3-trimethylcyclopent-3-en-1-yl)but-2-en-1-one Chemical compound C\C=C/C(=O)C1CC=C(C)C1(C)C GFBOMJGZLJHLMT-WAYWQWQTSA-N 0.000 claims description 2
- RLHZQFIKXSZZJV-UHFFFAOYSA-N 1-(1,2,2-trimethyl-3-bicyclo[3.1.0]hexanyl)ethanol Chemical compound CC1(C)C(C(O)C)CC2CC21C RLHZQFIKXSZZJV-UHFFFAOYSA-N 0.000 claims description 2
- YXGUBJPWGFKWQA-UHFFFAOYSA-N 1-(2,2,3-trimethyl-1-cyclopent-3-enyl)ethanone Chemical compound CC(=O)C1CC=C(C)C1(C)C YXGUBJPWGFKWQA-UHFFFAOYSA-N 0.000 claims description 2
- KFCDMVJQHRKPNO-UHFFFAOYSA-N 1-(2,2,3-trimethylcyclopent-3-en-1-yl)but-3-en-1-ol Chemical compound CC1=CCC(C(O)CC=C)C1(C)C KFCDMVJQHRKPNO-UHFFFAOYSA-N 0.000 claims description 2
- DFBMOLCGMDIWBV-UHFFFAOYSA-N 1-(2,2,3-trimethylcyclopent-3-en-1-yl)hept-6-en-1-one Chemical compound CC1=CCC(C(=O)CCCCC=C)C1(C)C DFBMOLCGMDIWBV-UHFFFAOYSA-N 0.000 claims description 2
- ZRJGRSNZMWFFGP-UHFFFAOYSA-N 1-(2,2,3-trimethylcyclopent-3-en-1-yl)hex-5-en-1-ol Chemical compound CC1=CCC(C(O)CCCC=C)C1(C)C ZRJGRSNZMWFFGP-UHFFFAOYSA-N 0.000 claims description 2
- XXPVVDTWSACJKY-UHFFFAOYSA-N 1-(2,2,3-trimethylcyclopent-3-en-1-yl)pent-4-en-1-ol Chemical compound CC1=CCC(C(O)CCC=C)C1(C)C XXPVVDTWSACJKY-UHFFFAOYSA-N 0.000 claims description 2
- JBXZYIIATJHKKX-UHFFFAOYSA-N 2,2-dimethyl-1-(2,2,3-trimethylcyclopent-3-en-1-yl)but-3-en-1-ol Chemical compound CC1=CCC(C(O)C(C)(C)C=C)C1(C)C JBXZYIIATJHKKX-UHFFFAOYSA-N 0.000 claims description 2
- QTAJCFGIVAOUBH-UHFFFAOYSA-N 2-(2,2,3-trimethylcyclopent-3-en-1-yl)hex-5-en-2-ol Chemical compound CC1=CCC(C(C)(O)CCC=C)C1(C)C QTAJCFGIVAOUBH-UHFFFAOYSA-N 0.000 claims description 2
- QKIQXGNRJXNRRD-UHFFFAOYSA-N 2-(2,2,3-trimethylcyclopent-3-en-1-yl)pentan-2-ol Chemical compound CCCC(C)(O)C1CC=C(C)C1(C)C QKIQXGNRJXNRRD-UHFFFAOYSA-N 0.000 claims description 2
- VLFWYOZUFFSEFI-UHFFFAOYSA-N 2-(2,2,3-trimethylcyclopent-3-en-1-yl)propan-2-ol Chemical compound CC1=CCC(C(C)(C)O)C1(C)C VLFWYOZUFFSEFI-UHFFFAOYSA-N 0.000 claims description 2
- XQGNLCILXSHNDU-UHFFFAOYSA-N 2-methyl-1-(2,2,3-trimethylcyclopent-3-en-1-yl)butan-1-ol Chemical compound CCC(C)C(O)C1CC=C(C)C1(C)C XQGNLCILXSHNDU-UHFFFAOYSA-N 0.000 claims description 2
- LEUJPNKSWVIVGG-UHFFFAOYSA-N 2-methyl-1-(2,2,3-trimethylcyclopent-3-en-1-yl)butan-1-one Chemical compound CCC(C)C(=O)C1CC=C(C)C1(C)C LEUJPNKSWVIVGG-UHFFFAOYSA-N 0.000 claims description 2
- PZMPFRFLCKLBMW-UHFFFAOYSA-N 2-methyl-1-(2,2,3-trimethylcyclopent-3-en-1-yl)prop-2-en-1-ol Chemical compound CC(=C)C(O)C1CC=C(C)C1(C)C PZMPFRFLCKLBMW-UHFFFAOYSA-N 0.000 claims description 2
- BOKHNTNTIVTRTH-UHFFFAOYSA-N 3,3-dimethyl-2-(2,2,3-trimethylcyclopent-3-en-1-yl)pent-4-en-2-ol Chemical compound CC1=CCC(C(C)(O)C(C)(C)C=C)C1(C)C BOKHNTNTIVTRTH-UHFFFAOYSA-N 0.000 claims description 2
- DUWIBZOMKJOWDJ-UHFFFAOYSA-N 3,3-dimethyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)hepta-1,6-dien-4-ol Chemical compound CC1=CCC(C(O)(CC=C)C(C)(C)C=C)C1(C)C DUWIBZOMKJOWDJ-UHFFFAOYSA-N 0.000 claims description 2
- MOEUIAIYJBVIDC-UHFFFAOYSA-N 3-(2,2,3-trimethylcyclopent-3-en-1-yl)hex-5-en-3-ol Chemical compound C=CCC(O)(CC)C1CC=C(C)C1(C)C MOEUIAIYJBVIDC-UHFFFAOYSA-N 0.000 claims description 2
- GCNAWFACHQGKCN-UHFFFAOYSA-N 3-methyl-1-(2,2,3-trimethylcyclopent-3-en-1-yl)butan-1-ol Chemical compound CC(C)CC(O)C1CC=C(C)C1(C)C GCNAWFACHQGKCN-UHFFFAOYSA-N 0.000 claims description 2
- ZNTFEKIGBBVCJS-UHFFFAOYSA-N 3-methyl-1-(2,2,3-trimethylcyclopent-3-en-1-yl)butan-1-one Chemical compound CC(C)CC(=O)C1CC=C(C)C1(C)C ZNTFEKIGBBVCJS-UHFFFAOYSA-N 0.000 claims description 2
- GAWPRSXIIADIJC-UHFFFAOYSA-N 4-(2,2,3-trimethylcyclopent-3-en-1-yl)oct-7-en-4-ol Chemical compound C=CCCC(O)(CCC)C1CC=C(C)C1(C)C GAWPRSXIIADIJC-UHFFFAOYSA-N 0.000 claims description 2
- DRDYAEKJGCGRKI-UHFFFAOYSA-N 6-methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)hept-1-en-4-ol Chemical compound CC(C)CC(O)(CC=C)C1CC=C(C)C1(C)C DRDYAEKJGCGRKI-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- IZCZHTIXNPMNDH-UHFFFAOYSA-N 2,2-dimethyl-1-(2,2,3-trimethylcyclopent-3-en-1-yl)but-3-en-1-one Chemical compound CC1=CCC(C(=O)C(C)(C)C=C)C1(C)C IZCZHTIXNPMNDH-UHFFFAOYSA-N 0.000 claims 1
- QUMSUJWRUHPEEJ-UHFFFAOYSA-N 4-Pentenal Chemical compound C=CCCC=O QUMSUJWRUHPEEJ-UHFFFAOYSA-N 0.000 claims 1
- HSHUHVOEMVTVRS-UHFFFAOYSA-N 7-octen-2-ol Chemical compound CC(O)CCCCC=C HSHUHVOEMVTVRS-UHFFFAOYSA-N 0.000 claims 1
- 239000000796 flavoring agent Substances 0.000 abstract 1
- 235000019634 flavors Nutrition 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 32
- 239000000047 product Substances 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 150000001299 aldehydes Chemical class 0.000 description 15
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
- 235000011751 Pogostemon cablin Nutrition 0.000 description 13
- 240000002505 Pogostemon cablin Species 0.000 description 13
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 13
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 11
- -1 4-pentenyl Chemical group 0.000 description 11
- 150000002576 ketones Chemical group 0.000 description 10
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 8
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 7
- 235000019645 odor Nutrition 0.000 description 7
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- YPZUZOLGGMJZJO-UHFFFAOYSA-N ambrofix Natural products C1CC2C(C)(C)CCCC2(C)C2C1(C)OCC2 YPZUZOLGGMJZJO-UHFFFAOYSA-N 0.000 description 6
- 239000004615 ingredient 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
- 238000000711 polarimetry Methods 0.000 description 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 4
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 description 4
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 4
- 235000006679 Mentha X verticillata Nutrition 0.000 description 4
- 235000002899 Mentha suaveolens Nutrition 0.000 description 4
- 235000001636 Mentha x rotundifolia Nutrition 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 229940022663 acetate Drugs 0.000 description 4
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 4
- 229940116229 borneol Drugs 0.000 description 4
- CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 description 4
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 229920002554 vinyl polymer Polymers 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
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 244000165082 Lavanda vera Species 0.000 description 3
- 235000010663 Lavandula angustifolia Nutrition 0.000 description 3
- 235000012550 Pimpinella anisum Nutrition 0.000 description 3
- 240000004760 Pimpinella anisum Species 0.000 description 3
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 3
- 235000011613 Pinus brutia Nutrition 0.000 description 3
- 241000018646 Pinus brutia Species 0.000 description 3
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 235000009508 confectionery Nutrition 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- 239000001102 lavandula vera Substances 0.000 description 3
- 235000018219 lavender Nutrition 0.000 description 3
- 229930007744 linalool Natural products 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- WLJVXDMOQOGPHL-UHFFFAOYSA-M phenylacetate Chemical compound [O-]C(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-M 0.000 description 3
- 229940049953 phenylacetate Drugs 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 150000003333 secondary alcohols Chemical class 0.000 description 3
- 239000001069 triethyl citrate Substances 0.000 description 3
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 3
- 235000013769 triethyl citrate Nutrition 0.000 description 3
- FINOAUDUYKVGDS-UHFFFAOYSA-N (2-tert-butylcyclohexyl) acetate Chemical compound CC(=O)OC1CCCCC1C(C)(C)C FINOAUDUYKVGDS-UHFFFAOYSA-N 0.000 description 2
- CRDAMVZIKSXKFV-YFVJMOTDSA-N (2-trans,6-trans)-farnesol Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CO CRDAMVZIKSXKFV-YFVJMOTDSA-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 2
- RNLHVODSMDJCBR-SOFGYWHQSA-N (e)-3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pent-4-en-2-ol Chemical compound CC(O)C(C)\C=C\C1CC=C(C)C1(C)C RNLHVODSMDJCBR-SOFGYWHQSA-N 0.000 description 2
- BVDMQAQCEBGIJR-UHFFFAOYSA-N 1-(2,2,6-trimethylcyclohexyl)hexan-3-ol Chemical compound CCCC(O)CCC1C(C)CCCC1(C)C BVDMQAQCEBGIJR-UHFFFAOYSA-N 0.000 description 2
- FVUGZKDGWGKCFE-UHFFFAOYSA-N 1-(2,3,8,8-tetramethyl-1,3,4,5,6,7-hexahydronaphthalen-2-yl)ethanone Chemical compound CC1(C)CCCC2=C1CC(C(C)=O)(C)C(C)C2 FVUGZKDGWGKCFE-UHFFFAOYSA-N 0.000 description 2
- DNRJTBAOUJJKDY-UHFFFAOYSA-N 2-Acetyl-3,5,5,6,8,8-hexamethyl-5,6,7,8- tetrahydronaphthalene Chemical compound CC(=O)C1=C(C)C=C2C(C)(C)C(C)CC(C)(C)C2=C1 DNRJTBAOUJJKDY-UHFFFAOYSA-N 0.000 description 2
- KHQDWCKZXLWDNM-UHFFFAOYSA-N 2-ethyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)but-2-en-1-ol Chemical compound CCC(CO)=CCC1CC=C(C)C1(C)C KHQDWCKZXLWDNM-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- JFTSYAALCNQOKO-UHFFFAOYSA-N 3-(4-ethylphenyl)-2,2-dimethylpropanal Chemical compound CCC1=CC=C(CC(C)(C)C=O)C=C1 JFTSYAALCNQOKO-UHFFFAOYSA-N 0.000 description 2
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 241000675108 Citrus tangerina Species 0.000 description 2
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- WTYGAUXICFETTC-UHFFFAOYSA-N cyclobarbital Chemical compound C=1CCCCC=1C1(CC)C(=O)NC(=O)NC1=O WTYGAUXICFETTC-UHFFFAOYSA-N 0.000 description 1
- 229960004138 cyclobarbital Drugs 0.000 description 1
- 239000001939 cymbopogon martini roxb. stapf. oil Substances 0.000 description 1
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 1
- XSNQECSCDATQEL-UHFFFAOYSA-N dihydromyrcenol Chemical compound C=CC(C)CCCC(C)(C)O XSNQECSCDATQEL-UHFFFAOYSA-N 0.000 description 1
- 229930008394 dihydromyrcenol Natural products 0.000 description 1
- 229940095104 dimethyl benzyl carbinyl acetate Drugs 0.000 description 1
- 238000004851 dishwashing Methods 0.000 description 1
- WTOYNNBCKUYIKC-UHFFFAOYSA-N dl-nootkatone Natural products C1CC(C(C)=C)CC2(C)C(C)CC(=O)C=C21 WTOYNNBCKUYIKC-UHFFFAOYSA-N 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 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
- 229940093858 ethyl acetoacetate Drugs 0.000 description 1
- 229940073505 ethyl vanillin Drugs 0.000 description 1
- 229960002217 eugenol Drugs 0.000 description 1
- 239000002979 fabric softener Substances 0.000 description 1
- 229940043259 farnesol Drugs 0.000 description 1
- 229930002886 farnesol Natural products 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- IFYYFLINQYPWGJ-VIFPVBQESA-N gamma-Decalactone Natural products CCCCCC[C@H]1CCC(=O)O1 IFYYFLINQYPWGJ-VIFPVBQESA-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
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 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
- 229940113087 geraniol Drugs 0.000 description 1
- HIGQPQRQIQDZMP-DHZHZOJOSA-N geranyl acetate Chemical compound CC(C)=CCC\C(C)=C\COC(C)=O HIGQPQRQIQDZMP-DHZHZOJOSA-N 0.000 description 1
- HNZUNIKWNYHEJJ-UHFFFAOYSA-N geranyl acetone Natural products CC(C)=CCCC(C)=CCCC(C)=O HNZUNIKWNYHEJJ-UHFFFAOYSA-N 0.000 description 1
- HNZUNIKWNYHEJJ-FMIVXFBMSA-N geranyl acetone Chemical compound CC(C)=CCC\C(C)=C\CCC(C)=O HNZUNIKWNYHEJJ-FMIVXFBMSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- UFLHIIWVXFIJGU-UHFFFAOYSA-N hex-3-en-1-ol Natural products CCC=CCCO UFLHIIWVXFIJGU-UHFFFAOYSA-N 0.000 description 1
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 239000003864 humus Substances 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 1
- 239000010656 jasmine oil Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000010501 lemon oil Substances 0.000 description 1
- 229940010454 licorice Drugs 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
- 239000002502 liposome Substances 0.000 description 1
- 150000002678 macrocyclic compounds Chemical class 0.000 description 1
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229940043353 maltol Drugs 0.000 description 1
- 239000013521 mastic Substances 0.000 description 1
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- YAHNYLGSSPTTAG-UHFFFAOYSA-N methyl n-(3,4-dichlorophenyl)carbamodithioate Chemical compound CSC(=S)NC1=CC=C(Cl)C(Cl)=C1 YAHNYLGSSPTTAG-UHFFFAOYSA-N 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000002088 nanocapsule Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 235000019477 peppermint oil Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- GTVITUZSWANKRK-UHFFFAOYSA-N propan-2-yloxycyclododecane Chemical compound CC(C)OC1CCCCCCCCCCC1 GTVITUZSWANKRK-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000019719 rose oil Nutrition 0.000 description 1
- 239000010666 rose oil Substances 0.000 description 1
- 229930007790 rose oxide Natural products 0.000 description 1
- 239000010671 sandalwood oil Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 235000019615 sensations Nutrition 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 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
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- LFSYLMRHJKGLDV-UHFFFAOYSA-N tetradecanolide Natural products O=C1CCCCCCCCCCCCCO1 LFSYLMRHJKGLDV-UHFFFAOYSA-N 0.000 description 1
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- DCSCXTJOXBUFGB-UHFFFAOYSA-N verbenone Natural products CC1=CC(=O)C2C(C)(C)C1C2 DCSCXTJOXBUFGB-UHFFFAOYSA-N 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229930007850 β-damascenone Natural products 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/05—Alcohols containing rings other than six-membered aromatic rings
- C07C33/12—Alcohols containing rings other than six-membered aromatic rings containing five-membered rings
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/203—Alicyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
- C07C49/537—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings to a five-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
- C07C49/557—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings having unsaturation outside the 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
- 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
- C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
- C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
- C11B9/0049—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings the condensed rings sharing two common C 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)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0802526.4A GB0802526D0 (en) | 2008-02-12 | 2008-02-12 | Organic compounds |
| GB0802526 | 2008-02-12 | ||
| PCT/CH2009/000053 WO2009100554A1 (en) | 2008-02-12 | 2009-02-10 | Organic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2373271T3 true ES2373271T3 (es) | 2012-02-01 |
Family
ID=39247479
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES09711211T Active ES2373271T3 (es) | 2008-02-12 | 2009-02-10 | Compuestos orgánicos. |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8445732B2 (enExample) |
| EP (1) | EP2252674B1 (enExample) |
| JP (1) | JP2011514325A (enExample) |
| CN (1) | CN101945985B (enExample) |
| AT (1) | ATE523580T1 (enExample) |
| BR (1) | BRPI0908367A2 (enExample) |
| ES (1) | ES2373271T3 (enExample) |
| GB (1) | GB0802526D0 (enExample) |
| MX (1) | MX2010008693A (enExample) |
| WO (1) | WO2009100554A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9370190B2 (en) | 2012-07-05 | 2016-06-21 | Eden Shield Ltd. | Pest repellents from plant extracts |
| GB201220341D0 (en) * | 2012-11-12 | 2012-12-26 | Givaudan Sa | Improvements in or relating to organic compounds |
| CN104452430B (zh) * | 2014-10-23 | 2016-09-07 | 广东比伦生活用纸有限公司 | 一种超韧加香的生活用纸及其生产方法 |
| CN114437021B (zh) * | 2022-02-15 | 2023-05-09 | 东莞波顿香料有限公司 | 一种藿香香气化合物及其制备方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4052341A (en) * | 1976-04-29 | 1977-10-04 | Givaudan Corporation | 3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pentan-2-ol compound and perfume compositions |
| EP0116903B1 (en) | 1983-02-16 | 1988-09-14 | L. GIVAUDAN & CIE Société Anonyme | Flavour compositions containing campholenic alcohol or derivatives thereof |
| EP0155591B1 (fr) | 1984-03-23 | 1988-05-25 | Firmenich Sa | Dérivés hydroxylés de l'aldéhyde campholénique, leur utilisation à titre d'ingrédients parfumants et composition parfumante les contenant |
| DD254382A1 (de) | 1986-12-09 | 1988-02-24 | Univ Leipzig | Verfahren zur herstellung von isomerem campholenaldehyd |
| US5288701A (en) | 1990-07-12 | 1994-02-22 | Givaudan-Roure Corporation | Derivatives of dihydrocampholenic aldehyde |
| US5039659A (en) * | 1990-08-07 | 1991-08-13 | International Flavors & Fragrances Inc. | 2,2,3-trimethylcyclopentenyl acetone derivatives, organoleptic uses thereof and process for preparing same |
| EP1008579B1 (en) * | 1996-04-09 | 2004-07-07 | Givaudan SA | Cyclopentenebutanol derivatives |
| DE69708368T2 (de) * | 1996-04-09 | 2002-09-26 | Givaudan S.A., Vernier-Geneve | Cyclopentanbutanolderivate als Duftstoffe |
| EP1668103B1 (en) * | 2003-09-30 | 2009-08-05 | Givaudan SA | 3-isopropyl-1-methylcyclopentyl derivatives and their use in fragrance applications |
| DE102004031589A1 (de) | 2004-06-30 | 2006-02-16 | Symrise Gmbh & Co. Kg | Verwendung von 3-Mercapto-3-methyl-hexan-1-ol als Malodor-Standard |
| GB0616002D0 (en) | 2006-08-11 | 2006-09-20 | Givaudan Sa | Organic compounds |
| GB0620556D0 (en) | 2006-10-18 | 2006-11-22 | Givauden Sa | Organic compounds |
| GB0802556D0 (en) * | 2008-02-12 | 2008-03-19 | Givaudan Sa | Organic compounds |
-
2008
- 2008-02-12 GB GBGB0802526.4A patent/GB0802526D0/en not_active Ceased
-
2009
- 2009-02-10 CN CN200980104960XA patent/CN101945985B/zh not_active Expired - Fee Related
- 2009-02-10 EP EP09711211A patent/EP2252674B1/en not_active Not-in-force
- 2009-02-10 BR BRPI0908367-7A patent/BRPI0908367A2/pt not_active IP Right Cessation
- 2009-02-10 ES ES09711211T patent/ES2373271T3/es active Active
- 2009-02-10 JP JP2010546194A patent/JP2011514325A/ja not_active Ceased
- 2009-02-10 MX MX2010008693A patent/MX2010008693A/es active IP Right Grant
- 2009-02-10 US US12/865,403 patent/US8445732B2/en not_active Expired - Fee Related
- 2009-02-10 AT AT09711211T patent/ATE523580T1/de not_active IP Right Cessation
- 2009-02-10 WO PCT/CH2009/000053 patent/WO2009100554A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| WO2009100554A1 (en) | 2009-08-20 |
| MX2010008693A (es) | 2010-08-30 |
| US20100331427A1 (en) | 2010-12-30 |
| CN101945985A (zh) | 2011-01-12 |
| EP2252674B1 (en) | 2011-09-07 |
| US8445732B2 (en) | 2013-05-21 |
| JP2011514325A (ja) | 2011-05-06 |
| GB0802526D0 (en) | 2008-03-19 |
| BRPI0908367A2 (pt) | 2015-07-28 |
| EP2252674A1 (en) | 2010-11-24 |
| CN101945985B (zh) | 2013-05-29 |
| ATE523580T1 (de) | 2011-09-15 |
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