NL8200342A - Nieuwe, op plaats 3 door een vinylketen gesubstitueerde, cyclopropaancarbonzuurverbindingen, hun bereiding, hun toepassing als reukmiddelen en de samenstellingen die zij bevatten. - Google Patents
Nieuwe, op plaats 3 door een vinylketen gesubstitueerde, cyclopropaancarbonzuurverbindingen, hun bereiding, hun toepassing als reukmiddelen en de samenstellingen die zij bevatten. Download PDFInfo
- Publication number
- NL8200342A NL8200342A NL8200342A NL8200342A NL8200342A NL 8200342 A NL8200342 A NL 8200342A NL 8200342 A NL8200342 A NL 8200342A NL 8200342 A NL8200342 A NL 8200342A NL 8200342 A NL8200342 A NL 8200342A
- Authority
- NL
- Netherlands
- Prior art keywords
- formula
- group
- compounds
- dimethyl
- carbon atoms
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 36
- 238000002360 preparation method Methods 0.000 title claims description 16
- 239000003205 fragrance Substances 0.000 title claims description 15
- -1 VINYL CHAIN Chemical group 0.000 title description 30
- 150000004649 carbonic acid derivatives Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 38
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 238000007239 Wittig reaction Methods 0.000 claims description 2
- 150000002430 hydrocarbons Chemical group 0.000 claims description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims description 2
- PKAHQJNJPDVTDP-UHFFFAOYSA-N methyl cyclopropanecarboxylate Chemical compound COC(=O)C1CC1 PKAHQJNJPDVTDP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 2
- VFNUAZMERKWUOT-UHFFFAOYSA-N 2-ethyl-1-methylcyclopropane-1-carboxylic acid Chemical compound CCC1CC1(C)C(O)=O VFNUAZMERKWUOT-UHFFFAOYSA-N 0.000 claims 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims 1
- LEIUFQFSNLHXSJ-UHFFFAOYSA-N benzyl cyclopropanecarboxylate Chemical compound C1CC1C(=O)OCC1=CC=CC=C1 LEIUFQFSNLHXSJ-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 66
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 51
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical group OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 14
- 150000004702 methyl esters Chemical class 0.000 description 14
- 235000019441 ethanol Nutrition 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- 235000019645 odor Nutrition 0.000 description 9
- 239000000377 silicon dioxide Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 125000004494 ethyl ester group Chemical group 0.000 description 8
- 239000002304 perfume Substances 0.000 description 8
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000000344 soap Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- PDOBSLHNWIVQJX-UHFFFAOYSA-N 1-ethenylcyclopropane-1-carboxylic acid Chemical compound OC(=O)C1(C=C)CC1 PDOBSLHNWIVQJX-UHFFFAOYSA-N 0.000 description 3
- NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 3
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000012459 cleaning agent Substances 0.000 description 3
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- QPCBFWBMGXGMNJ-KTERXBQFSA-N (1r,3r)-2,2-dimethyl-3-[(e)-(2-oxooxolan-3-ylidene)methyl]cyclopropane-1-carboxylic acid Chemical compound OC(=O)[C@H]1C(C)(C)[C@@H]1\C=C/1C(=O)OCC\1 QPCBFWBMGXGMNJ-KTERXBQFSA-N 0.000 description 2
- OYDPVRNLLQZQFY-KTERXBQFSA-N (1r,3r)-2,2-dimethyl-3-[(e)-(2-oxothiolan-3-ylidene)methyl]cyclopropane-1-carboxylic acid Chemical compound OC(=O)[C@H]1C(C)(C)[C@@H]1\C=C/1C(=O)SCC\1 OYDPVRNLLQZQFY-KTERXBQFSA-N 0.000 description 2
- QPCBFWBMGXGMNJ-JBGJSGBSSA-N (1r,3s)-2,2-dimethyl-3-[(e)-(2-oxooxolan-3-ylidene)methyl]cyclopropane-1-carboxylic acid Chemical compound OC(=O)[C@H]1C(C)(C)[C@H]1\C=C/1C(=O)OCC\1 QPCBFWBMGXGMNJ-JBGJSGBSSA-N 0.000 description 2
- OYDPVRNLLQZQFY-JBGJSGBSSA-N (1r,3s)-2,2-dimethyl-3-[(e)-(2-oxothiolan-3-ylidene)methyl]cyclopropane-1-carboxylic acid Chemical compound OC(=O)[C@H]1C(C)(C)[C@H]1\C=C/1C(=O)SCC\1 OYDPVRNLLQZQFY-JBGJSGBSSA-N 0.000 description 2
- FRHRVQQUICVJDG-UHFFFAOYSA-M 1,3-dioxolan-2-ylmethyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1OCCO1 FRHRVQQUICVJDG-UHFFFAOYSA-M 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- PTQGFDXPHNRDCV-UHFFFAOYSA-N 3-formyl-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)C(C=O)C1C(O)=O PTQGFDXPHNRDCV-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- OEYQBKYISMRWQB-UHFFFAOYSA-N Santal Natural products C=1C(OC)=CC(O)=C(C2=O)C=1OC=C2C1=CC=C(O)C(O)=C1 OEYQBKYISMRWQB-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 229960000956 coumarin Drugs 0.000 description 2
- 235000001671 coumarin Nutrition 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 229940093499 ethyl acetate Drugs 0.000 description 2
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000003722 gum benzoin Substances 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000001585 thymus vulgaris Substances 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- MMYLYTWGWZNUQB-NBJOHNLQSA-N (1R,3S)-3-[(Z)-2-cyanoethenyl]-2,2-dimethylcyclopropane-1-carbonyl chloride Chemical compound CC1([C@@H]([C@@H]1\C=C/C#N)C(=O)Cl)C MMYLYTWGWZNUQB-NBJOHNLQSA-N 0.000 description 1
- ZOBYYMKJNISVSO-LFXWPVBRSA-N (1r,3r)-3-[(e)-3-methoxy-3-oxoprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound COC(=O)\C=C\[C@@H]1[C@@H](C(O)=O)C1(C)C ZOBYYMKJNISVSO-LFXWPVBRSA-N 0.000 description 1
- PTQGFDXPHNRDCV-UHNVWZDZSA-N (1r,3r)-3-formyl-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)[C@H](C=O)[C@H]1C(O)=O PTQGFDXPHNRDCV-UHNVWZDZSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- VHQDWSOWPAYEOY-SNAWJCMRSA-N 2,2-dimethyl-3-[(e)-3-oxobut-1-enyl]cyclopropane-1-carbonyl chloride Chemical compound CC(=O)\C=C\C1C(C(Cl)=O)C1(C)C VHQDWSOWPAYEOY-SNAWJCMRSA-N 0.000 description 1
- 125000003562 2,2-dimethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- GGZQLTVZPOGLCC-UHFFFAOYSA-N 2-(2-bromoethyl)-1,3-dioxolane Chemical compound BrCCC1OCCO1 GGZQLTVZPOGLCC-UHFFFAOYSA-N 0.000 description 1
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-Phenylethanol Natural products OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004336 3,3-dimethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004337 3-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- XOLBXXZZQLVKRU-UHFFFAOYSA-N C1CC1.[C] Chemical compound C1CC1.[C] XOLBXXZZQLVKRU-UHFFFAOYSA-N 0.000 description 1
- XXBBTXLOULQVTQ-ZFWWWQNUSA-N CC1([C@@H]([C@@H]1C=CC(=O)OC)C(=O)OCC1=CC=CC=C1)C Chemical compound CC1([C@@H]([C@@H]1C=CC(=O)OC)C(=O)OCC1=CC=CC=C1)C XXBBTXLOULQVTQ-ZFWWWQNUSA-N 0.000 description 1
- 241001090476 Castoreum Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- JOZKFWLRHCDGJA-LLVKDONJSA-N Citronellyl acetate Natural products CC(=O)OCC[C@H](C)CCC=C(C)C JOZKFWLRHCDGJA-LLVKDONJSA-N 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 240000000560 Citrus x paradisi Species 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 1
- 239000005792 Geraniol Substances 0.000 description 1
- 241000208152 Geranium Species 0.000 description 1
- 235000010254 Jasminum officinale Nutrition 0.000 description 1
- 240000005385 Jasminum sambac Species 0.000 description 1
- UWKAYLJWKGQEPM-LBPRGKRZSA-N Linaloyl acetate Natural products CC(C)=CCC[C@](C)(C=C)OC(C)=O UWKAYLJWKGQEPM-LBPRGKRZSA-N 0.000 description 1
- 235000015511 Liquidambar orientalis Nutrition 0.000 description 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- KVWWIYGFBYDJQC-GHMZBOCLSA-N Methyl dihydrojasmonate Chemical compound CCCCC[C@@H]1[C@@H](CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-GHMZBOCLSA-N 0.000 description 1
- 244000179970 Monarda didyma Species 0.000 description 1
- 235000010672 Monarda didyma Nutrition 0.000 description 1
- GLZPCOQZEFWAFX-JXMROGBWSA-N Nerol Natural products CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 description 1
- 101100228519 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) gch-1 gene Proteins 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 240000002505 Pogostemon cablin Species 0.000 description 1
- 235000011751 Pogostemon cablin Nutrition 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 239000004870 Styrax Substances 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 240000002657 Thymus vulgaris Species 0.000 description 1
- 235000007303 Thymus vulgaris Nutrition 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- UZFLPKAIBPNNCA-BQYQJAHWSA-N alpha-ionone Chemical compound CC(=O)\C=C\C1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-BQYQJAHWSA-N 0.000 description 1
- UZFLPKAIBPNNCA-UHFFFAOYSA-N alpha-ionone Natural products CC(=O)C=CC1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-UHFFFAOYSA-N 0.000 description 1
- GUUHFMWKWLOQMM-UHFFFAOYSA-N alpha-n-hexylcinnamic aldehyde Natural products CCCCCCC(C=O)=CC1=CC=CC=C1 GUUHFMWKWLOQMM-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
- 229940007550 benzyl acetate Drugs 0.000 description 1
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyloxyacetoaldehyde Natural products CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 1
- NEHNMFOYXAPHSD-UHFFFAOYSA-N beta-citronellal Natural products O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 description 1
- JOZKFWLRHCDGJA-UHFFFAOYSA-N beta-citronellol acetate Natural products CC(=O)OCCC(C)CCC=C(C)C JOZKFWLRHCDGJA-UHFFFAOYSA-N 0.000 description 1
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-M carbamimidate Chemical compound NC([NH-])=O XSQUKJJJFZCRTK-UHFFFAOYSA-M 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000010627 cedar oil Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229930003633 citronellal Natural products 0.000 description 1
- 235000000983 citronellal Nutrition 0.000 description 1
- 239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 description 1
- 239000001071 citrus reticulata blanco var. mandarin Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- 125000005469 ethylenyl group Chemical group 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000834 fixative Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 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
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000010656 jasmine oil Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- UWKAYLJWKGQEPM-UHFFFAOYSA-N linalool acetate Natural products CC(C)=CCCC(C)(C=C)OC(C)=O UWKAYLJWKGQEPM-UHFFFAOYSA-N 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- OJEQSSJFSNLMLB-UHFFFAOYSA-N p-Tolyl phenylacetate Chemical compound C1=CC(C)=CC=C1OC(=O)CC1=CC=CC=C1 OJEQSSJFSNLMLB-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- NRNCYVBFPDDJNE-UHFFFAOYSA-N pemoline Chemical compound O1C(N)=NC(=O)C1C1=CC=CC=C1 NRNCYVBFPDDJNE-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000010666 rose oil Substances 0.000 description 1
- 235000019719 rose oil Nutrition 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000005406 washing Methods 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
- C11B9/0069—Heterocyclic compounds
- C11B9/0092—Heterocyclic compounds containing only N as heteroatom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- C11B9/0069—Heterocyclic compounds
- C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
- C11B9/0076—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing less than six atoms
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)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8102236A FR2499071A1 (fr) | 1981-02-05 | 1981-02-05 | Nouveaux derives de l'acide cyclopropane carboxylique substitue en 3 par une chaine vinylique, leur procede de preparation et leur application comme agents parfumants |
| FR8102236 | 1981-02-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8200342A true NL8200342A (nl) | 1982-09-01 |
Family
ID=9254870
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8200342A NL8200342A (nl) | 1981-02-05 | 1982-01-29 | Nieuwe, op plaats 3 door een vinylketen gesubstitueerde, cyclopropaancarbonzuurverbindingen, hun bereiding, hun toepassing als reukmiddelen en de samenstellingen die zij bevatten. |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4431576A (enExample) |
| JP (1) | JPS57154147A (enExample) |
| CH (1) | CH657846A5 (enExample) |
| DE (1) | DE3203977A1 (enExample) |
| FR (1) | FR2499071A1 (enExample) |
| IT (1) | IT1147810B (enExample) |
| NL (1) | NL8200342A (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4522749A (en) * | 1981-12-21 | 1985-06-11 | National Distillers And Chemical Corporation | Process for augmenting or enhancing the aroma of a fragrance by adding a vinylcyclopropane compound |
| FR2534252A1 (fr) * | 1982-10-12 | 1984-04-13 | Roussel Uclaf | Nouveaux derives de l'acide cyclopropane carboxylique substitues en 3 par une chaine vinylique elle-meme substituee, leur procede de preparation et leur application comme pesticides |
| US6576247B1 (en) * | 1994-11-10 | 2003-06-10 | Kanebo Ltd. And T. Hasegawa Co. Ltd. | Sustained-release aromatic and method of detecting micro-organism by using the same |
| US5767305A (en) * | 1997-04-03 | 1998-06-16 | International Flavors & Fragrances Inc. | Cyclopropyl carboxylic acid esters and uses thereof in imparting, augmenting and enhancing aromas |
| ES2621903T3 (es) * | 2012-01-18 | 2017-07-05 | International Flavors & Fragrances Inc. | Nuevos compuestos organolépticos |
| EP4402230A1 (en) * | 2021-09-13 | 2024-07-24 | Symrise AG | Cyclopropanated fragrance compounds |
| CN116375604B (zh) * | 2022-02-22 | 2024-10-22 | 江苏扬农化工股份有限公司 | 一种双键含氰基的拟除虫菊酯化合物及合成方法与应用 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2045177A5 (enExample) * | 1969-06-13 | 1971-02-26 | Roussel Uclaf | |
| AU432259B1 (en) * | 1970-02-26 | 1972-08-24 | Sumitomo Chemical Company, Limited | Novel substituted chrysanthemates |
| US3714153A (en) * | 1970-06-22 | 1973-01-30 | Roussel Uclaf | Novel cyclopropanecarboxylic acids |
| JPS5111171B1 (enExample) * | 1971-06-28 | 1976-04-09 | Sumitomo Chemical Co | |
| GB1448586A (en) * | 1973-06-07 | 1976-09-08 | Nat Res Dev | 3-substituted-2,2,dimethyl cyclopropane carboxylic acid esters and their use as insecticides |
| US3926860A (en) * | 1974-01-28 | 1975-12-16 | Int Flavors & Fragrances Inc | Fragrance materials containing cis-2-n-pentyl cyclopropane-1-carboxylic acid |
| DE2710174A1 (de) * | 1977-03-09 | 1978-09-14 | Bayer Ag | Verfahren zur herstellung von dihalogenvinyl-cyclopropancarbonsaeuren und deren ester |
| CA1117673A (en) * | 1977-12-29 | 1982-02-02 | Hajime Shichijo | Tuning apparatus |
| DE2819788A1 (de) * | 1978-05-05 | 1979-11-08 | Bayer Ag | Benzylester mit fluorsubstituierten aether- und/oder thioaethergruppen und ihre verwendung als insektizide |
| AU526817B2 (en) * | 1978-06-21 | 1983-02-03 | Ici Australia Limited | Pesticides |
| DE2961566D1 (en) * | 1978-12-15 | 1982-02-04 | Ciba Geigy Ag | Process for the preparation of optically active 3-substituted 2-(2',2'-dihalovinyl)-cyclopropane-1-carboxylic acids and their derivatives; 4-(2',2',2'-trihaloethyl)-cyclobutane-1-sulphonic acid salts and their preparation |
| FR2455025A1 (fr) * | 1979-04-26 | 1980-11-21 | Roussel Uclaf | Esters de derives de l'allethrolone et d'acides cyclopropane carboxyliques, leurs procedes de preparation et les compositions les renfermant |
| US4358409A (en) * | 1979-05-02 | 1982-11-09 | Bayer Aktiengesellschaft | Preparation of styryl cyclopropane insecticide intermediates |
| US4335252A (en) * | 1979-05-24 | 1982-06-15 | Fmc Corporation | Insecticidal pyrethroid enantiomer pair |
-
1981
- 1981-02-05 FR FR8102236A patent/FR2499071A1/fr active Granted
-
1982
- 1982-01-27 US US06/343,348 patent/US4431576A/en not_active Expired - Fee Related
- 1982-01-28 IT IT47671/82A patent/IT1147810B/it active
- 1982-01-29 NL NL8200342A patent/NL8200342A/nl not_active Application Discontinuation
- 1982-02-04 CH CH691/82A patent/CH657846A5/fr not_active IP Right Cessation
- 1982-02-05 JP JP57016462A patent/JPS57154147A/ja active Pending
- 1982-02-05 DE DE19823203977 patent/DE3203977A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| IT1147810B (it) | 1986-11-26 |
| FR2499071A1 (fr) | 1982-08-06 |
| JPS57154147A (en) | 1982-09-22 |
| FR2499071B1 (enExample) | 1984-10-19 |
| CH657846A5 (fr) | 1986-09-30 |
| DE3203977A1 (de) | 1982-09-02 |
| IT8247671A0 (it) | 1982-01-28 |
| US4431576A (en) | 1984-02-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2010507414A (ja) | 悪臭対抗組成物 | |
| US4521331A (en) | Method of imparting a pleasant odor | |
| JP5563454B2 (ja) | シクロヘキセン誘導体および着臭剤としてのそれらの使用 | |
| DE60309348T2 (de) | Estern und ihre verwendung in der parfümerie | |
| DE60020355T2 (de) | Duft Vorläufer | |
| NL8200342A (nl) | Nieuwe, op plaats 3 door een vinylketen gesubstitueerde, cyclopropaancarbonzuurverbindingen, hun bereiding, hun toepassing als reukmiddelen en de samenstellingen die zij bevatten. | |
| DE60009394T2 (de) | Cyclopentylalkylnitrile und die Verwendung von Cyclopentylalkyl-Derivaten als Duftstoffe | |
| DE602005003937T2 (de) | Alicyclische carbonsäureoxycarbonylmethylester und deren verwendung als riechstoffen | |
| EP0002510B1 (de) | Cyclohexane, Verfahren zu deren Herstellung, deren Verwendung und diese enthaltende Kompositionen | |
| EP0826764B1 (de) | Riechstoffkompositionen enthaltend substituierte 2-Acetylbenzofurane | |
| DE60313973T2 (de) | Duftstoffzusammensetzung | |
| DE2729121B2 (de) | Verwendung von Cyclopentanderivaten als Riechstoffe und neue Cyclopentanderivaten | |
| DE2914109A1 (de) | 1,3-dioxane und sie enthaltende parfuemzubereitung | |
| JP4676880B2 (ja) | シクロオクト−（エン−）イル誘導体の香料としての使用 | |
| DE60106941T2 (de) | Ungesättigte ester und ihre verwendung in riechstoff- und geschmackstoffzusammensetzungen | |
| EP0211303B1 (de) | 2-Acyl-5-methylfurane, ein Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE2517620A1 (de) | Verwendung von exo-norbornyl-2- essigsaeureestern als riechstoffe sowie diese enthaltende riechstoffkompositionen | |
| CN111448299B (zh) | 气味剂和包含气味剂的组合物 | |
| DE602004001076T2 (de) | Riechstoffverbindungen | |
| EP0962441B1 (de) | Bicyclische Aldehyde und Ketone | |
| FR2873922A1 (fr) | Tetrahydropyran(on)es substitues en beta, leur procede de synthese et leur utilisation en parfumerie | |
| NL8105199A (nl) | Nieuwe cyclopropaancarbonzuurderivaten, werkwijze ter bereiding daarvan en de toepassing daarvan voor de bereiding van parfumpreparaten. | |
| FR2543134A2 (fr) | Nouveaux derives du cyclopropane, leur procede de preparation et leur application a la preparation de compositions parfumantes | |
| DE2365939B2 (de) | Cyclopentene, Verfahren zu deren Herstellung und Riechstoffkompositionen | |
| DE602005005015T2 (de) | Bicycloä3.3.1ünonane und bicycloä3.3.ü nonene und deren verwendung als geschmack- oder duftstoffe |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BV | The patent application has lapsed | ||
| A85 | Still pending on 85-01-01 | ||
| BV | The patent application has lapsed |