JP4200094B2 - じゃ香性を有する芳香剤としてのシクロアルカンカルボン酸誘導体 - Google Patents
じゃ香性を有する芳香剤としてのシクロアルカンカルボン酸誘導体 Download PDFInfo
- Publication number
- JP4200094B2 JP4200094B2 JP2003500032A JP2003500032A JP4200094B2 JP 4200094 B2 JP4200094 B2 JP 4200094B2 JP 2003500032 A JP2003500032 A JP 2003500032A JP 2003500032 A JP2003500032 A JP 2003500032A JP 4200094 B2 JP4200094 B2 JP 4200094B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- mmol
- compounds
- formula
- fragrance
- 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 - Lifetime
Links
- 239000003205 fragrance Substances 0.000 title claims abstract description 32
- 239000002253 acid Substances 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 74
- 239000000203 mixture Substances 0.000 claims abstract description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 150000002148 esters Chemical class 0.000 abstract description 45
- 238000002360 preparation method Methods 0.000 abstract description 3
- 239000004615 ingredient Substances 0.000 abstract description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Substances CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- -1 3,3-dimethylcyclopentyl Chemical group 0.000 description 15
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 12
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 11
- 235000019645 odor Nutrition 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 239000002304 perfume Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 241000402754 Erythranthe moschata Species 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- BJLXIEORMMUPSC-UHFFFAOYSA-N [2,2-dimethyl-3-(2-methyl-5-prop-1-en-2-ylcyclopenten-1-yl)propyl] cyclopropanecarboxylate Chemical compound CC(=C)C1CCC(C)=C1CC(C)(C)COC(=O)C1CC1 BJLXIEORMMUPSC-UHFFFAOYSA-N 0.000 description 6
- 238000003818 flash chromatography Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000012267 brine Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- 229940126062 Compound A Drugs 0.000 description 4
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 4
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 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
- RWSDULKUTPNPMB-UHFFFAOYSA-N [2,2-dimethyl-3-(2-methyl-5-prop-1-en-2-ylcyclopenten-1-yl)propyl] propanoate Chemical compound CCC(=O)OCC(C)(C)CC1=C(C)CCC1C(C)=C RWSDULKUTPNPMB-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000012259 ether extract Substances 0.000 description 4
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- UIERETOOQGIECD-ARJAWSKDSA-M 2-Methyl-2-butenoic acid Natural products C\C=C(\C)C([O-])=O UIERETOOQGIECD-ARJAWSKDSA-M 0.000 description 3
- UIERETOOQGIECD-UHFFFAOYSA-N Angelic acid Natural products CC=C(C)C(O)=O UIERETOOQGIECD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 244000290333 Vanilla fragrans Species 0.000 description 3
- 235000009499 Vanilla fragrans Nutrition 0.000 description 3
- 235000012036 Vanilla tahitensis Nutrition 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 3
- UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 description 3
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 2
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 2
- MMEAVAVRZYNYFB-UHFFFAOYSA-N 1,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1CC1(C)C(O)=O MMEAVAVRZYNYFB-UHFFFAOYSA-N 0.000 description 2
- BVUYQSFBRKUJNK-UHFFFAOYSA-N 1-(3,3-dimethylcyclohexyl)ethanol Chemical compound CC(O)C1CCCC(C)(C)C1 BVUYQSFBRKUJNK-UHFFFAOYSA-N 0.000 description 2
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-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
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 239000005792 Geraniol Substances 0.000 description 2
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- HQKQRXZEXPXXIG-VJOHVRBBSA-N chembl2333940 Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@H]1[C@@](OC(C)=O)(C)CC2 HQKQRXZEXPXXIG-VJOHVRBBSA-N 0.000 description 2
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 2
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 2
- 238000001212 derivatisation Methods 0.000 description 2
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- IFYYFLINQYPWGJ-UHFFFAOYSA-N gamma-decalactone Chemical compound CCCCCCC1CCC(=O)O1 IFYYFLINQYPWGJ-UHFFFAOYSA-N 0.000 description 2
- 229940113087 geraniol Drugs 0.000 description 2
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229930007744 linalool Natural products 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- CZCBTSFUTPZVKJ-UHFFFAOYSA-N rose oxide Chemical compound CC1CCOC(C=C(C)C)C1 CZCBTSFUTPZVKJ-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 2
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 2
- 235000012141 vanillin Nutrition 0.000 description 2
- PHXATPHONSXBIL-UHFFFAOYSA-N xi-gamma-Undecalactone Chemical compound CCCCCCCC1CCC(=O)O1 PHXATPHONSXBIL-UHFFFAOYSA-N 0.000 description 2
- ORHSGDMSYGKJJY-SAIIYOCFSA-N (1'r,6's)-2,2,4',7',7'-pentamethylspiro[1,3-dioxane-5,5'-bicyclo[4.1.0]heptane] Chemical compound C12([C@H]3[C@H](C3(C)C)CCC2C)COC(C)(C)OC1 ORHSGDMSYGKJJY-SAIIYOCFSA-N 0.000 description 1
- 239000001414 (2E)-2-(phenylmethylidene)octanal Substances 0.000 description 1
- AVJMJMPVWWWELJ-DHZHZOJOSA-N (2e)-1-methoxy-3,7-dimethylocta-2,6-diene Chemical compound COC\C=C(/C)CCC=C(C)C AVJMJMPVWWWELJ-DHZHZOJOSA-N 0.000 description 1
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- VPKMGDRERYMTJX-CMDGGOBGSA-N 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one Chemical compound CCC(=O)\C=C\C1C(C)=CCCC1(C)C VPKMGDRERYMTJX-CMDGGOBGSA-N 0.000 description 1
- YQYKESUTYHZAGG-BZNIZROVSA-N 1-[(1r,2s)-1,2,8,8-tetramethyl-1,3,4,5,6,7-hexahydronaphthalen-2-yl]ethanone Chemical compound C1([C@H]([C@@](CC2)(C)C(C)=O)C)=C2CCCC1(C)C YQYKESUTYHZAGG-BZNIZROVSA-N 0.000 description 1
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 description 1
- DIZKLZKLNKQFGB-UHFFFAOYSA-N 1-methylcyclopropane-1-carboxylic acid Chemical compound OC(=O)C1(C)CC1 DIZKLZKLNKQFGB-UHFFFAOYSA-N 0.000 description 1
- GELKGHVAFRCJNA-UHFFFAOYSA-N 2,2-Dimethyloxirane Chemical compound CC1(C)CO1 GELKGHVAFRCJNA-UHFFFAOYSA-N 0.000 description 1
- HMKKIXGYKWDQSV-SDNWHVSQSA-N 2-Pentyl-3-phenyl-2-propenal Chemical compound CCCCC\C(C=O)=C/C1=CC=CC=C1 HMKKIXGYKWDQSV-SDNWHVSQSA-N 0.000 description 1
- CJBXHTMAMPXERG-UHFFFAOYSA-N 2-[1-(3,3-dimethylcyclohexyl)ethoxy]-2-methylpropan-1-ol Chemical compound OCC(C)(C)OC(C)C1CCCC(C)(C)C1 CJBXHTMAMPXERG-UHFFFAOYSA-N 0.000 description 1
- AYEGPMGNMOIHDL-UHFFFAOYSA-N 2-methylcyclopropane-1-carboxylic acid Chemical compound CC1CC1C(O)=O AYEGPMGNMOIHDL-UHFFFAOYSA-N 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- AUBLFWWZTFFBNU-UHFFFAOYSA-N 6-butan-2-ylquinoline Chemical compound N1=CC=CC2=CC(C(C)CC)=CC=C21 AUBLFWWZTFFBNU-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- LSTSBZKIQFOPHA-UHFFFAOYSA-N CCC(OCC(C)(C)OC(C)C1CC(C)(C)CCC1)=O Chemical compound CCC(OCC(C)(C)OC(C)C1CC(C)(C)CCC1)=O LSTSBZKIQFOPHA-UHFFFAOYSA-N 0.000 description 1
- 240000007436 Cananga odorata Species 0.000 description 1
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 1
- WYYGRKMQUNGVJC-UHFFFAOYSA-N ClCC(=O)OC1CC(CCC1)(C)C Chemical compound ClCC(=O)OC1CC(CCC1)(C)C WYYGRKMQUNGVJC-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- FKUPPRZPSYCDRS-UHFFFAOYSA-N Cyclopentadecanolide Chemical compound O=C1CCCCCCCCCCCCCCO1 FKUPPRZPSYCDRS-UHFFFAOYSA-N 0.000 description 1
- 208000027534 Emotional disease Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- YIKYNHJUKRTCJL-UHFFFAOYSA-N Ethyl maltol Chemical compound CCC=1OC=CC(=O)C=1O YIKYNHJUKRTCJL-UHFFFAOYSA-N 0.000 description 1
- 239000005770 Eugenol Substances 0.000 description 1
- 235000001453 Glycyrrhiza echinata Nutrition 0.000 description 1
- 244000303040 Glycyrrhiza glabra Species 0.000 description 1
- 235000006200 Glycyrrhiza glabra Nutrition 0.000 description 1
- 235000017382 Glycyrrhiza lepidota Nutrition 0.000 description 1
- 235000010254 Jasminum officinale Nutrition 0.000 description 1
- 240000005385 Jasminum sambac Species 0.000 description 1
- HYMLWHLQFGRFIY-UHFFFAOYSA-N Maltol Natural products CC1OC=CC(=O)C1=O HYMLWHLQFGRFIY-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
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- 239000002386 air freshener Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- GUUHFMWKWLOQMM-NTCAYCPXSA-N alpha-hexylcinnamaldehyde Chemical compound CCCCCC\C(C=O)=C/C1=CC=CC=C1 GUUHFMWKWLOQMM-NTCAYCPXSA-N 0.000 description 1
- 229940072717 alpha-hexylcinnamaldehyde Drugs 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
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- YPZUZOLGGMJZJO-UHFFFAOYSA-N ambrofix Natural products C1CC2C(C)(C)CCCC2(C)C2C1(C)OCC2 YPZUZOLGGMJZJO-UHFFFAOYSA-N 0.000 description 1
- YPZUZOLGGMJZJO-LQKXBSAESA-N ambroxan Chemical compound CC([C@@H]1CC2)(C)CCC[C@]1(C)[C@@H]1[C@]2(C)OCC1 YPZUZOLGGMJZJO-LQKXBSAESA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 229940007550 benzyl acetate Drugs 0.000 description 1
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 235000000484 citronellol Nutrition 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 229940093503 ethyl maltol Drugs 0.000 description 1
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 1
- 229960002217 eugenol Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 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
- 239000000499 gel Substances 0.000 description 1
- 239000010648 geranium oil Substances 0.000 description 1
- 235000019717 geranium oil Nutrition 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 229940010454 licorice Drugs 0.000 description 1
- 150000002678 macrocyclic compounds Chemical class 0.000 description 1
- 229940043353 maltol Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 239000001738 pogostemon cablin oil Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000010666 rose oil Substances 0.000 description 1
- 235000019719 rose oil Nutrition 0.000 description 1
- 229930007790 rose oxide Natural products 0.000 description 1
- 239000010671 sandalwood oil Substances 0.000 description 1
- 230000008786 sensory perception of smell Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- BSWGGJHLVUUXTL-UHFFFAOYSA-N silver zinc Chemical compound [Zn].[Ag] BSWGGJHLVUUXTL-UHFFFAOYSA-N 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- GOZDTZWAMGHLDY-UHFFFAOYSA-L sodium picosulfate Chemical compound [Na+].[Na+].C1=CC(OS(=O)(=O)[O-])=CC=C1C(C=1N=CC=CC=1)C1=CC=C(OS([O-])(=O)=O)C=C1 GOZDTZWAMGHLDY-UHFFFAOYSA-L 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 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
- 229940117960 vanillin Drugs 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Medicines Containing Plant Substances (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Description
R1およびR2は一緒になってCH2であってもよく、および
nは、整数1、2または3であり、ただし、n+(R1およびR2中の炭素原子数)は、5未満である、
で表される化合物。
Yは、シクロプロピル残基[化合物(5)];2−メチルシクロプロピル残基[化合物(6)];シクロブチル残基[化合物(7)];シクロペンチル残基[化合物(8)];1,2−ジメチルシクロプロピル残基[化合物(9)];および1−メチルシクロプロピル残基[化合物(10)]である、
で示される。
−精油およびエーテル抽出物、たとえば、カストリウム、コスタスルートオイル、オークモス・アブソリュート、ゼラニウム油、ジャスミン・アブソリュート、パチョリ油、ローズ油、ビャクダン油またはイランイランノキ油;
−アルコール、たとえば、シトロネロール、エバノール(登録商標)、オイゲノール、ゲラニオール、スーパーミュゲ(Super Muguet)(登録商標)、リナロール、フェニルエチルアルコール、サンダロア(Sandalore)(登録商標)、テルピネオールまたはティンベロール(Timberol)(登録商標);
−エーテルおよびアセタール、たとえば、アンブロックス(Ambrox)(登録商標)、ゲラニルメチルエーテル、ローズオキサイドまたはスピランブレン(Spirambrene)(登録商標);
−エステルおよびラクトン、たとえば、ベンジルアセテート、セドリルアセテート、シクロムスク(1)、γ-デカラクトン、ヘルベトリド(登録商標)(3)、γ-ウンデカラクトンまたはベチベニルアセテート;
−マクロサイクル、たとえば、アンブレットリド、エチレンブラシレートまたはエキサルトリド(登録商標);
および
−複素環、たとえば、イソブチルキノリン
と混合してもよい。
例1
2-[1'-(3'',3''-ジメチルシクロヘキシル)エトキシ]-2-メチルプロパン-1-オール (化合物A)
窒素雰囲気下0℃で、トルエン中に1.8Mエチルアルミニウムジクロライドを含む溶液178ml(321 mmol)を500 mlシクロヘキサン中に1-(3',3'-ジメチルシクロヘキシル)エタノール 100 g (641 mmol)およびイソブチレンオキサイド55.4 g (769 mmol)を含む攪拌溶液にゆっくり添加した。完全に添加した後、冷却浴を除去し、反応混合物を室温まで温め、この温度で15時間攪拌を続けた。反応混合物は、濃リン酸で酸性化した塩水1l中に添加し、エーテルで3回抽出した。混合有機抽出物を塩水および水で洗浄し、硫酸ナトリウムで乾燥し、ロータリーエバポレーターで濃縮した。粗生成物(136 g)を78-85℃ / 0.3 mbarで蒸留することにより、純粋な2-[1'-(3'',3''-ジメチルシクロヘキシル)-エトキシ]-2-メチルプロパン-1-オール55.1 g (38%)が得られ、出発材料60.4 gが回収された。
シクロプロパンカルボン酸2'-[1''-(3''',3'''-ジメチルシクロヘキシル)エトキシ]-2'-メチルプロピルエステル (5)
化合物A1.50 g (6.58 mmol)およびシクロプロパンカルボン酸0.56 g (6.58 mmol)を窒素雰囲気下、無水ジクロロメタン20 ml中に溶解した。0℃で無水ジクロロメタン20 ml中に4-(ジメチルアミノ)ピリジン160 mg (1.31 mmol)を含む溶液を攪拌しながら添加し、さらに5分間攪拌後、無水ジクロロメタン20 ml中にN,N'-ジシクロヘキシルカルボジイミド1.49 g (7.24 mmol)を含む溶液を添加した。0℃で1時間攪拌した後、冷却浴を除去し、反応混合物を室温で15時間攪拌した。不溶性材料をその後、吸引ろ過し、ジクロロメタンで洗浄した。有機溶液を混合し、減圧下で濃縮乾燥した。粗生成物 (2.75 g)をフラッシュクロマトグラフィー (100 gシリカゲル、ペンタン/エーテル、19:1、Rf = 0.45)で精製し、純粋な嗅覚性標的化合物シクロプロパンカルボン酸2'-[1''-(3''',3'''-ジメチルシクロヘキシル)エトキシ]-2'-メチルプロピルエステル(5)1.46 g (75%)が得られた。
2-メチルシクロプロパンカルボン酸2'-[1''-(3''',3'''-ジメチルシクロヘキシル)エトキシ]-2'-メチルプロピルエステル (6);シクロブタンカルボン酸2'-[1''-(3''',3'''-ジメチル-シクロヘキシル)エトキシ]-2'-メチルプロピルエステル (7);シクロペンタンカルボン酸2'-[1''-(3''',3'''-ジメチル-シクロヘキシル)エトキシ]-2'-メチルプロピルエステル (8);および1-メチルシクロプロパンカルボン酸2'-[1''-(3''',3'''-ジメチルシクロヘキシル)エトキシ]-2'-メチルプロピルエステル(10)を、例1に従って合成した化合物Aと対応するカルボン酸とを例2と同様に反応させることにより合成した。
チグリン酸2'-[1''-(3''',3'''-ジメチルシクロヘキシル)エトキシ]-2'-メチルプロピルエステル(化合物B)
化合物(5)の合成と類似して、化合物A10.0 g (43.8 mmol)およびチグリン酸4.38 g (43.8 mmol)を無水ジクロロメタン中で4-(ジメチルアミノ)ピリジン530 mg (4.38 mmol)およびN,N'-ジシクロヘキシルカルボジイミド9.94 g (48.2 mmol)の存在下エステル化した。通常の精製により、粗生成物17.9 g得られ、フラッシュクロマトグラフィー(400 gシリカゲル、ペンタン/エーテル、19:1、Rf = 0.36)によって精製され、純粋なチグリン酸2'-[1''-(3''',3'''-ジメチルシクロヘキシル)エトキシ]-2'-メチルプロピルエステル9.44 g (69%)が得られ、そのうち3.10 g (10.0 mmol)を続く反応に用いた。
1,2-ジメチルシクロプロパンカルボン酸2'-[1''-(3''',3'''-ジメチルシクロヘキシル)エトキシ]-2'-メチルプロピルエステル(9)
攪拌により、熱濃縮酢酸10 ml中に、硝酸銀10 mg (0.06 mmol)を溶解した。亜鉛粉1.70 g (26 mmol)を少量添加し、1分間、攪拌を続けた。熱源を除去し、反応物を室温まで冷却した。形成された亜鉛-銀対をデカンティングにより単離し、濃酢酸10 mlおよび、5回、10 mlエーテルで洗浄した。無水エーテル15 mlを生成物に注ぎ、少量のシルバーウールを添加し、化合物B3.10 g (10 mmol)を続けて添加する。5分間、このエーテル懸濁液に攪拌しながら、ジヨードメタン3.48 g (13 mmol)を滴下添加し、反応物を2日間、1日後にジヨードメタン3.48 g (13 mmol)を追加で添加しながら、熱還流した。室温まで冷却後、反応混合物を氷冷飽和塩化アンモニウム水溶液200 mlへ注いだ。生成物を100 mlエーテルで2回抽出し、混合したエーテル抽出物を50 mlの水、50 mlの40%亜硫酸水素ナトリウム水溶液で洗浄、再び50 ml の水で2回洗浄および最後に25 mlの塩水で洗浄した。その後、混合抽出物を硫酸ナトリウムで乾燥し、ロータリーエバポレーターで濃縮し、10 mlヘキサン中に採取した。室温で、攪拌しながら、溶液が茶色になるまで、臭素を滴下添加した。溶液をその後、氷中に注ぎ、50 mlのエーテルで2回抽出した。エーテル抽出物を飽和炭酸水素ナトリウム水溶液50 ml で洗浄し、50 mlの水および25 mlの塩水で洗浄し、および硫酸ナトリウムで乾燥した。溶媒を蒸発することで、粗生成物が3.46 g得られ、フラッシュクロマトグラフィー (120 g シリカゲル、ペンタン/エーテル、19:1、Rf = 0.42)によって精製し、720 mg (22%)の純粋な嗅覚標的化合物1,2-ジメチルシクロプロパンカルボン酸 2'-[1''-(3''',3'''-ジメチルシクロヘキシル)エトキシ]-2'-メチルプロピルエステル (9)が得られた。
シクロプロパンカルボン酸3'-(5''-イソプロペニル-2''-メチルシクロペント-1-エニル)-2',2'-ジメチルプロピルエステル(11)
化合物(5)および(6)の製造と同様にして、ホフマン(Hoffmann)およびボンフラウンブルク(von Fraunberg )(DE 2513996, 例3)に従って製造した3-(5-イソプロペニル-2-メチルシクロペント-1-エニル)-2,2-ジメチルプロパノール0.70 g (3.37 mmol)およびシクロプロパンカルボン酸0.28 g (3.37 mmol)を無水ジクロロメタン中で4-(ジメチルアミノ) ピリジン410 mg (3.37 mmol)およびN,N'-ジシクロヘキシルカルボジイミド760 mg (3.37 mmol)の存在下、エステル化した。通常の精製によって、粗生成物1.59 g が得られ、フラッシュクロマトグラフィー (100 g シリカゲル、ペンタン/エーテル、49:1、Rf = 0.50) によって精製し、標的のシクロプロパンカルボン酸3-(5-イソプロペニル-2-メチル-シクロペント-1-エニル)-2,2-ジメチル-プロピルエステル(11)0.87 g (94%)が得られた。
シクロプロパンカルボン酸1''-(3''',3'''-ジメチルシクロヘキシル)エトキシカルボニルメチルエステル(12)
我々の通常の手順に従い、1-(3',3'-ジメチルシクロヘキシル)エタノール15.6 g (100 mmol)をクロロ酢酸9.45 g (100 mmol)で無水ジクロロメタン中4-(ジメチルアミノ) ピリジン1.22 g (10 mmol)およびN,N'-ジシクロヘキシルカルボジイミド22.7 g (110 mmol) の存在下、エステル化した。通常の精製によって、粗生成物28.4 gが得られ、フラッシュクロマトグラフィー (600 gシリカゲル、ペンタン/エーテル、19:1、Rf = 0.77) によって精製し、クロロ酢酸1-(3,3-ジメチルシクロヘキシル)エチルエステル20.5 g (88%)が得られ、そのうち4.80 g (20.6 mmol)をジエチルケトン50 mlおよび1,4-ジオキサン13 ml中に溶解した。この溶液に、シクロプロパンカルボン酸1.77 g (20.6 mmol)および炭酸カリウム5.69 g (41.2 mmol)を添加し、生じた混合物を20時間還流した。その後、反応混合物を氷100 g中に注ぎ、生成物を150 mlのエーテルで2回抽出した。混合エーテル抽出物を100 mlの水および50 mlの塩水で洗浄し、硫酸ナトリウムで乾燥し、減圧下で濃縮し、粗生成物26.0 gが得られた。フラッシュクロマトグラフィー (175 gシリカゲル、ペンタン/エーテル、9:1、Rf = 0.52) によって精製し、標的化合物シクロプロパンカルボン酸1-(3,3-ジメチルシクロヘキシル)エトキシカルボニルメチルエステル(12)3.56 g (61%)が得られた。
Claims (2)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP01113377A EP1262474A1 (en) | 2001-06-01 | 2001-06-01 | Cycloalkanecarboxylic acid derivatives as fragrants with musk characteristics |
PCT/CH2002/000282 WO2002096852A1 (en) | 2001-06-01 | 2002-05-30 | Cycloalkanecarboxylic acid derivatives as fragrants with musk characteristics |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2004535412A JP2004535412A (ja) | 2004-11-25 |
JP2004535412A5 JP2004535412A5 (ja) | 2008-09-25 |
JP4200094B2 true JP4200094B2 (ja) | 2008-12-24 |
Family
ID=8177615
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2003500032A Expired - Lifetime JP4200094B2 (ja) | 2001-06-01 | 2002-05-30 | じゃ香性を有する芳香剤としてのシクロアルカンカルボン酸誘導体 |
Country Status (10)
Country | Link |
---|---|
US (1) | US7390779B2 (ja) |
EP (2) | EP1262474A1 (ja) |
JP (1) | JP4200094B2 (ja) |
CN (1) | CN1249014C (ja) |
AT (1) | ATE381530T1 (ja) |
BR (1) | BR0210098B1 (ja) |
DE (1) | DE60224180T2 (ja) |
ES (1) | ES2298366T3 (ja) |
MX (1) | MXPA03010828A (ja) |
WO (1) | WO2002096852A1 (ja) |
Families Citing this family (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB0204919D0 (en) * | 2002-03-01 | 2002-04-17 | Cst Medical Ltd | Treatment of female sexual dysfunction |
DE60309200T2 (de) | 2002-11-29 | 2007-10-04 | Givaudan S.A. | Aliphatische verbindungen als duftstoffe mit moschuscharakter |
GB0227807D0 (en) * | 2002-11-29 | 2003-01-08 | Givaudan Sa | Improvements in or relating ot organic compounds |
ES2265618T3 (es) | 2003-03-19 | 2007-02-16 | Firmenich Sa | Compuestos odorantes. |
DE10335053A1 (de) * | 2003-07-31 | 2005-02-24 | Symrise Gmbh & Co. Kg | Alicyclische Ester mit Moschusgeruch |
GB0410134D0 (en) * | 2004-05-07 | 2004-06-09 | Givaudan Sa | Organic compounds |
US20060133415A1 (en) * | 2004-12-21 | 2006-06-22 | Mueller Peter D | Wireless internetwork transfer apparatus, systems, and methods |
MX2009004132A (es) * | 2006-10-24 | 2009-04-28 | Givaudan Sa | Composiciones para contrarrestar el mal olor. |
MX2010002470A (es) * | 2007-09-07 | 2010-03-26 | Givaudan Sa | Derivados de dimetilciclohexilo como neutralizadores de malos olores. |
JP5442356B2 (ja) * | 2009-08-11 | 2014-03-12 | 長谷川香料株式会社 | 脂肪族エステル類、該化合物を含有する香料組成物および該化合物の製造法 |
WO2012055875A1 (en) | 2010-10-25 | 2012-05-03 | Symrise Ag | Perfume |
US10407378B2 (en) | 2014-04-21 | 2019-09-10 | Takasago International Corporation | Compound, and flavor and/or fragrance composition containing said compound |
JP6840168B2 (ja) * | 2016-04-20 | 2021-03-10 | エルジー ハウスホールド アンド ヘルスケア リミテッド | 香料組成物 |
CN111372468A (zh) | 2017-10-06 | 2020-07-03 | 嘉吉公司 | 甜菊醇糖苷溶解度增强剂 |
CN107759445A (zh) * | 2017-11-23 | 2018-03-06 | 帕潘纳(北京)科技有限公司 | 一种制备1‑(3,3,‑二甲基环己基)乙醇的方法 |
US20220049183A1 (en) | 2018-12-20 | 2022-02-17 | Symrise Ag | Alicyclic musk fragrance compounds |
WO2020210118A1 (en) | 2019-04-06 | 2020-10-15 | Cargill, Incorporated | Sensory modifiers |
EP4132901A1 (en) | 2020-04-08 | 2023-02-15 | Symrise AG | Esters as fragrance compounds |
CN111333509B (zh) * | 2020-04-14 | 2022-06-10 | 东莞波顿香料有限公司 | 苹果风味化合物及其制备方法和食品添加剂 |
EP4402230A1 (en) | 2021-09-13 | 2024-07-24 | Symrise AG | Cyclopropanated fragrance compounds |
WO2023209139A1 (en) * | 2022-04-29 | 2023-11-02 | Firmenich Sa | Musky odorant |
WO2024206466A1 (en) | 2023-03-30 | 2024-10-03 | International Flavors & Fragrances Inc. | Method for producing a musk fragrance intermediate using copper catalysts |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5166412A (en) | 1990-08-28 | 1992-11-24 | Firmenich S.A. | Esters and their use in perfumery |
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 |
ATE231834T1 (de) * | 1998-09-09 | 2003-02-15 | Firmenich & Cie | Ester mit moschusgeruch und ihre anwendung in der parfümerie |
-
2001
- 2001-06-01 EP EP01113377A patent/EP1262474A1/en not_active Withdrawn
-
2002
- 2002-05-30 WO PCT/CH2002/000282 patent/WO2002096852A1/en active IP Right Grant
- 2002-05-30 CN CNB028110048A patent/CN1249014C/zh not_active Expired - Lifetime
- 2002-05-30 MX MXPA03010828A patent/MXPA03010828A/es active IP Right Grant
- 2002-05-30 JP JP2003500032A patent/JP4200094B2/ja not_active Expired - Lifetime
- 2002-05-30 EP EP02727147A patent/EP1392640B1/en not_active Expired - Lifetime
- 2002-05-30 ES ES02727147T patent/ES2298366T3/es not_active Expired - Lifetime
- 2002-05-30 BR BRPI0210098-3B1A patent/BR0210098B1/pt active IP Right Grant
- 2002-05-30 US US10/478,626 patent/US7390779B2/en not_active Expired - Lifetime
- 2002-05-30 AT AT02727147T patent/ATE381530T1/de not_active IP Right Cessation
- 2002-05-30 DE DE60224180T patent/DE60224180T2/de not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
DE60224180T2 (de) | 2008-12-11 |
MXPA03010828A (es) | 2004-02-17 |
EP1392640B1 (en) | 2007-12-19 |
DE60224180D1 (de) | 2008-01-31 |
US20040234568A1 (en) | 2004-11-25 |
US7390779B2 (en) | 2008-06-24 |
EP1262474A1 (en) | 2002-12-04 |
BR0210098B1 (pt) | 2013-07-16 |
ES2298366T3 (es) | 2008-05-16 |
EP1392640A1 (en) | 2004-03-03 |
JP2004535412A (ja) | 2004-11-25 |
ATE381530T1 (de) | 2008-01-15 |
CN1249014C (zh) | 2006-04-05 |
BR0210098A (pt) | 2004-04-13 |
WO2002096852A1 (en) | 2002-12-05 |
CN1512980A (zh) | 2004-07-14 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP4200094B2 (ja) | じゃ香性を有する芳香剤としてのシクロアルカンカルボン酸誘導体 | |
JP5399908B2 (ja) | 有機化合物 | |
ES2297694T3 (es) | Esteres de oxicarbonilmetilo de acidos carboxilicos aliciclicos y su utilizacion como odorantes. | |
DE60009394T2 (de) | Cyclopentylalkylnitrile und die Verwendung von Cyclopentylalkyl-Derivaten als Duftstoffe | |
JP4352002B2 (ja) | エステルおよび香料におけるそれらの使用 | |
US4336204A (en) | Menthene nitriles and use as perfume chemicals | |
US6326349B1 (en) | Methylcyclotetradec-5-en-1-ones | |
MX2007015272A (es) | Cicloalquiliden-(fenilo orto sustituidos)-acetonitrilos y su uso como odorizantes. | |
JP4518957B2 (ja) | じゃこう特性を有する香料としての脂肪族化合物 | |
JPH06305999A (ja) | 着臭剤組成物 | |
EP2424852B1 (en) | 2-oxaspiro[5,5]undec-8-ene derivatives useful in fragrance compositions | |
US4104202A (en) | Perfume compositions and process for preparing same | |
US4287100A (en) | 1,2,3,6-Tetrahydrobenzyl alcohol esters and compositions containing the same | |
JPS647978B2 (ja) | ||
JP2004506047A (ja) | 不飽和エステル及びそれらの芳香及び風味組成物での使用 | |
EP0189581A1 (de) | Neue 2,3-disubstituierte Bicyclo[2.2.1]heptane und -heptene, deren Herstellung und deren Verwendung als Riechstoffe | |
EP1771407A1 (en) | 4-hepten-2-yl salicylate and its use as a fragrance ingredient | |
MX2014012403A (es) | Compuestos organicos. | |
MXPA00006415A (en) | Cyclopentylalkyl-nitriles and the use of odoriferous cyclopentylalkyl derivatives as fragrances | |
MXPA99009730A (en) | Perfumes comprising 3-alkylcycloalkanols |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20050530 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20050530 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20080507 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20080807 |
|
A524 | Written submission of copy of amendment under article 19 pct |
Free format text: JAPANESE INTERMEDIATE CODE: A524 Effective date: 20080807 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20080909 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20081006 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20111010 Year of fee payment: 3 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 4200094 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20111010 Year of fee payment: 3 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20121010 Year of fee payment: 4 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20121010 Year of fee payment: 4 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20131010 Year of fee payment: 5 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
EXPY | Cancellation because of completion of term |