JP2009149577A - Cyclohexyl alkanol - Google Patents
Cyclohexyl alkanol Download PDFInfo
- Publication number
- JP2009149577A JP2009149577A JP2007330049A JP2007330049A JP2009149577A JP 2009149577 A JP2009149577 A JP 2009149577A JP 2007330049 A JP2007330049 A JP 2007330049A JP 2007330049 A JP2007330049 A JP 2007330049A JP 2009149577 A JP2009149577 A JP 2009149577A
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- Prior art keywords
- group
- carbon atoms
- fragrance
- hydrocarbon group
- formula
- Prior art date
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 title claims abstract description 25
- 239000000203 mixture Substances 0.000 claims abstract description 27
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 10
- 239000003205 fragrance Substances 0.000 claims description 49
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 17
- 239000000796 flavoring agent Substances 0.000 claims 1
- 235000019634 flavors Nutrition 0.000 claims 1
- 150000002430 hydrocarbons Chemical group 0.000 abstract description 17
- 239000002304 perfume Substances 0.000 abstract description 7
- 239000002994 raw material Substances 0.000 abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
- 239000001257 hydrogen Substances 0.000 abstract description 4
- 229930195733 hydrocarbon Natural products 0.000 abstract description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 241000234435 Lilium Species 0.000 abstract 1
- -1 aldehyde compound Chemical class 0.000 description 34
- 238000006243 chemical reaction Methods 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- 235000000423 Convallaria keiskei Nutrition 0.000 description 8
- 240000007938 Convallaria keiskei Species 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- NHDDMYLQQPPHND-UHFFFAOYSA-N (1-ethyl-4-propan-2-ylcyclohexyl)methanol Chemical compound CCC1(CO)CCC(C(C)C)CC1 NHDDMYLQQPPHND-UHFFFAOYSA-N 0.000 description 7
- JZQODQIOQZITAD-UHFFFAOYSA-N CC(C)C1CCC(CC1)(CO)C(C)C Chemical compound CC(C)C1CCC(CC1)(CO)C(C)C JZQODQIOQZITAD-UHFFFAOYSA-N 0.000 description 7
- 150000001299 aldehydes Chemical class 0.000 description 7
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000002168 alkylating agent Substances 0.000 description 5
- 229940100198 alkylating agent Drugs 0.000 description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 239000012279 sodium borohydride Substances 0.000 description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 150000001350 alkyl halides Chemical class 0.000 description 4
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 150000004678 hydrides Chemical class 0.000 description 4
- 150000002576 ketones Chemical group 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 3
- WEEGYLXZBRQIMU-UHFFFAOYSA-N 1,8-cineole Natural products C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 3
- 229940022663 acetate Drugs 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 150000007514 bases Chemical class 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 229930016911 cinnamic acid Natural products 0.000 description 3
- 235000013985 cinnamic acid Nutrition 0.000 description 3
- 235000009508 confectionery Nutrition 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 3
- 230000002688 persistence Effects 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZNJFBWYDHIGLCU-HWKXXFMVSA-N (-)-Jasmonic acid Natural products CC\C=C/C[C@@H]1[C@@H](CC(O)=O)CCC1=O ZNJFBWYDHIGLCU-HWKXXFMVSA-N 0.000 description 2
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 2
- IGXPXGSEJIPGAQ-UHFFFAOYSA-N 1-ethyl-4-propan-2-ylcyclohexane-1-carbaldehyde Chemical compound CCC1(C=O)CCC(C(C)C)CC1 IGXPXGSEJIPGAQ-UHFFFAOYSA-N 0.000 description 2
- LOKPJYNMYCVCRM-UHFFFAOYSA-N 16-Hexadecanolide Chemical compound O=C1CCCCCCCCCCCCCCCO1 LOKPJYNMYCVCRM-UHFFFAOYSA-N 0.000 description 2
- UIERETOOQGIECD-ARJAWSKDSA-M 2-Methyl-2-butenoic acid Natural products C\C=C(\C)C([O-])=O UIERETOOQGIECD-ARJAWSKDSA-M 0.000 description 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 2
- 125000006022 2-methyl-2-propenyl group Chemical group 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
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 2
- INAXVXBDKKUCGI-UHFFFAOYSA-N 4-hydroxy-2,5-dimethylfuran-3-one Chemical compound CC1OC(C)=C(O)C1=O INAXVXBDKKUCGI-UHFFFAOYSA-N 0.000 description 2
- GLBRWLVEZQRTKY-UHFFFAOYSA-N 4-propan-2-ylcyclohexane-1-carbaldehyde Chemical compound CC(C)C1CCC(C=O)CC1 GLBRWLVEZQRTKY-UHFFFAOYSA-N 0.000 description 2
- OALYTRUKMRCXNH-UHFFFAOYSA-N 5-pentyloxolan-2-one Chemical compound CCCCCC1CCC(=O)O1 OALYTRUKMRCXNH-UHFFFAOYSA-N 0.000 description 2
- GHBSPIPJMLAMEP-UHFFFAOYSA-N 6-pentyloxan-2-one Chemical compound CCCCCC1CCCC(=O)O1 GHBSPIPJMLAMEP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- UIERETOOQGIECD-UHFFFAOYSA-N Angelic acid Natural products CC=C(C)C(O)=O UIERETOOQGIECD-UHFFFAOYSA-N 0.000 description 2
- ZCTQGTTXIYCGGC-UHFFFAOYSA-N Benzyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 2
- DZNVIZQPWLDQHI-UHFFFAOYSA-N Citronellyl formate Chemical compound O=COCCC(C)CCC=C(C)C DZNVIZQPWLDQHI-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- FKUPPRZPSYCDRS-UHFFFAOYSA-N Cyclopentadecanolide Chemical compound O=C1CCCCCCCCCCCCCCO1 FKUPPRZPSYCDRS-UHFFFAOYSA-N 0.000 description 2
- 239000012448 Lithium borohydride Substances 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000220317 Rosa Species 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- KGEKLUUHTZCSIP-HOSYDEDBSA-N [(1s,4s,6r)-1,7,7-trimethyl-6-bicyclo[2.2.1]heptanyl] acetate Chemical compound C1C[C@]2(C)[C@H](OC(=O)C)C[C@H]1C2(C)C KGEKLUUHTZCSIP-HOSYDEDBSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 description 2
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 2
- JOZKFWLRHCDGJA-UHFFFAOYSA-N citronellol acetate Chemical compound CC(=O)OCCC(C)CCC=C(C)C JOZKFWLRHCDGJA-UHFFFAOYSA-N 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- OSOIQJGOYGSIMF-UHFFFAOYSA-N cyclopentadecanone Chemical compound O=C1CCCCCCCCCCCCCC1 OSOIQJGOYGSIMF-UHFFFAOYSA-N 0.000 description 2
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 description 2
- 150000002168 ethanoic acid esters Chemical class 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
- 238000000605 extraction Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- IFYYFLINQYPWGJ-UHFFFAOYSA-N gamma-decalactone Chemical compound CCCCCCC1CCC(=O)O1 IFYYFLINQYPWGJ-UHFFFAOYSA-N 0.000 description 2
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 2
- HIGQPQRQIQDZMP-UHFFFAOYSA-N geranil acetate Natural products CC(C)=CCCC(C)=CCOC(C)=O HIGQPQRQIQDZMP-UHFFFAOYSA-N 0.000 description 2
- HIGQPQRQIQDZMP-DHZHZOJOSA-N geranyl acetate Chemical compound CC(C)=CCC\C(C)=C\COC(C)=O HIGQPQRQIQDZMP-DHZHZOJOSA-N 0.000 description 2
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 2
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 2
- ZNJFBWYDHIGLCU-UHFFFAOYSA-N jasmonic acid Natural products CCC=CCC1C(CC(O)=O)CCC1=O ZNJFBWYDHIGLCU-UHFFFAOYSA-N 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 2
- UWKAYLJWKGQEPM-LBPRGKRZSA-N linalyl acetate Chemical compound CC(C)=CCC[C@](C)(C=C)OC(C)=O UWKAYLJWKGQEPM-LBPRGKRZSA-N 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- FRISMOQHTLZZRP-UHFFFAOYSA-N nerol oxide Chemical compound CC(C)=CC1CC(C)=CCO1 FRISMOQHTLZZRP-UHFFFAOYSA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
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- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229940043353 maltol Drugs 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 229930007503 menthone Natural products 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- ZWNPUELCBZVMDA-HJWRWDBZSA-N methyl 2-nonenoate Chemical compound CCCCCC\C=C/C(=O)OC ZWNPUELCBZVMDA-HJWRWDBZSA-N 0.000 description 1
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- 229940102398 methyl anthranilate Drugs 0.000 description 1
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- 229960001047 methyl salicylate Drugs 0.000 description 1
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- JPTOCTSNXXKSSN-UHFFFAOYSA-N methylheptenone Chemical compound CCCC=CC(=O)CC JPTOCTSNXXKSSN-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
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- FALTVGCCGMDSNZ-UHFFFAOYSA-N n-(1-phenylethyl)benzamide Chemical compound C=1C=CC=CC=1C(C)NC(=O)C1=CC=CC=C1 FALTVGCCGMDSNZ-UHFFFAOYSA-N 0.000 description 1
- WMBOCUXXNSOQHM-UHFFFAOYSA-N n-butylidenephthalide Natural products C1=CC=C2C(=CCCC)OC(=O)C2=C1 WMBOCUXXNSOQHM-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- WASNIKZYIWZQIP-AWEZNQCLSA-N nerolidol Natural products CC(=CCCC(=CCC[C@@H](O)C=C)C)C WASNIKZYIWZQIP-AWEZNQCLSA-N 0.000 description 1
- HIGQPQRQIQDZMP-FLIBITNWSA-N neryl acetate Chemical compound CC(C)=CCC\C(C)=C/COC(C)=O HIGQPQRQIQDZMP-FLIBITNWSA-N 0.000 description 1
- 239000001702 nutmeg Substances 0.000 description 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N o-aminobenzenecarboxylic acid Natural products NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 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
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
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- RUVINXPYWBROJD-UHFFFAOYSA-N para-methoxyphenyl Natural products COC1=CC=C(C=CC)C=C1 RUVINXPYWBROJD-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 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
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-OUBTZVSYSA-N potassium-40 Chemical compound [40K] ZLMJMSJWJFRBEC-OUBTZVSYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- RAGBYXLIHQFIPK-UHFFFAOYSA-N prop-2-ynyl benzenesulfonate Chemical compound C#CCOS(=O)(=O)C1=CC=CC=C1 RAGBYXLIHQFIPK-UHFFFAOYSA-N 0.000 description 1
- 150000003151 propanoic acid esters Chemical class 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- GRWFGVWFFZKLTI-UHFFFAOYSA-N rac-alpha-Pinene Natural products CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229930007790 rose oxide Natural products 0.000 description 1
- 235000002020 sage Nutrition 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
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical compound [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 229930006978 terpinene Natural products 0.000 description 1
- 150000003507 terpinene derivatives Chemical class 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- YUVKTUCPWGPBLJ-UHFFFAOYSA-N tert-butyl 2-cyclohexylacetate Chemical compound CC(C)(C)OC(=O)CC1CCCCC1 YUVKTUCPWGPBLJ-UHFFFAOYSA-N 0.000 description 1
- RKSOPLXZQNSWAS-UHFFFAOYSA-N tert-butyl bromide Chemical compound CC(C)(C)Br RKSOPLXZQNSWAS-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- NPFVOOAXDOBMCE-UHFFFAOYSA-N trans-3-hexenyl acetate Natural products CCC=CCCOC(C)=O NPFVOOAXDOBMCE-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
- BJIOGJUNALELMI-UHFFFAOYSA-N trans-isoeugenol Natural products COC1=CC(C=CC)=CC=C1O BJIOGJUNALELMI-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- WCTNXGFHEZQHDR-UHFFFAOYSA-N valencene Natural products C1CC(C)(C)C2(C)CC(C(=C)C)CCC2=C1 WCTNXGFHEZQHDR-UHFFFAOYSA-N 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- ZFNVDHOSLNRHNN-UHFFFAOYSA-N xi-3-(4-Isopropylphenyl)-2-methylpropanal Chemical compound O=CC(C)CC1=CC=C(C(C)C)C=C1 ZFNVDHOSLNRHNN-UHFFFAOYSA-N 0.000 description 1
- SFEOKXHPFMOVRM-BQYQJAHWSA-N γ-ionone Chemical compound CC(=O)\C=C\C1C(=C)CCCC1(C)C SFEOKXHPFMOVRM-BQYQJAHWSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Abstract
Description
本発明は、調合香料原料として有用な新規のシクロヘキシルアルカノール、その製造方法、及び該シクロヘキシルアルカノールを含有する香料組成物に関する。 The present invention relates to a novel cyclohexyl alkanol useful as a blended fragrance raw material, a method for producing the same, and a fragrance composition containing the cyclohexyl alkanol.
4-イソプロピルシクロヘキシルアルカノールには香料として有用な化合物があることが知られている。例えば、非特許文献1には4−イソプロピルシクロヘキサンメタノールと1−(4−イソプロピルシクロヘキシル)−エタノールが調合香料に有用であることが記載されている。これらの化合物はいずれも調合香料にみずみずしい甘さを付与することが知られているが、あたたかい木様の甘さを持つフローラル香気ではないため、調合香料に十分なあたたかさを与えることはできなかった。 It is known that 4-isopropylcyclohexylalkanol has a compound useful as a fragrance. For example, Non-Patent Document 1 describes that 4-isopropylcyclohexanemethanol and 1- (4-isopropylcyclohexyl) -ethanol are useful for blended fragrances. All of these compounds are known to impart fresh sweetness to blended fragrances, but they are not floral fragrances that have a warm wood-like sweetness, so they cannot give enough warmth to blended fragrances. It was.
本発明の課題は、あたたかい木様の甘さとすずらんの花を想起させるフローラル香を有し、調合香料に木様のあたたかさや甘さとフローラル香気を付与することができる、調合香料原料として有用なシクロヘキシルアルカノール、その製造方法、及び当該シクロヘキシルアルカノールを含有する香料組成物に関する。 An object of the present invention is to have a floral fragrance reminiscent of warm wood-like sweetness and suzuran flowers, and can be used as a raw material for blended fragrances, which can impart warmth, sweetness and floral fragrance of wood-like to blended fragrances. The present invention relates to an alkanol, a method for producing the same, and a fragrance composition containing the cyclohexyl alkanol.
本発明者らは、種々のアルコール系化合物を合成し、その香気について検討したところ、六員環炭化水素骨格上のアルカノール基が結合した1位に炭素数2〜4の炭化水素基を有し、4位にイソプロピル基を有する特定のシクロヘキシルアルカノールが、あたたかい木様の甘さとすずらんの花を想起させるフローラル香を有し、かつ優れた香気持続性を有することを見出した。
すなわち、本発明は、
(1)一般式(I)
The inventors of the present invention synthesized various alcohol compounds and studied their aromas. As a result, the present inventors have a hydrocarbon group having 2 to 4 carbon atoms at the 1-position to which the alkanol group on the six-membered hydrocarbon skeleton is bonded. It has been found that a specific cyclohexylalkanol having an isopropyl group at the 4-position has a floral fragrance reminiscent of a warm wood-like sweetness and a suzuran flower, and has an excellent fragrance persistence.
That is, the present invention
(1) General formula (I)
で表されるシクロヘキシルアルカノール、
Cyclohexyl alkanol represented by
(2)一般式(II)
で表されるカルボニル化合物を用いて、一般式(III)
(2) General formula (II)
Using a carbonyl compound represented by general formula (III)
(式中、R1は炭素数2〜4の炭化水素基を示し、R3は前記と同じである。)
で表されるカルボニル化合物を得た後に還元を行う、上記一般式(I)で表されるシクロヘキシルアルカノールの製造方法、及び
(3)上記(1)記載の一般式(I)で表されるシクロヘキシルアルカノールを含有する香料組成物、
に関する。
(In the formula, R 1 represents a hydrocarbon group having 2 to 4 carbon atoms, and R 3 is the same as described above.)
A method for producing a cyclohexylalkanol represented by the above general formula (I), and (3) a cyclohexyl represented by the general formula (I) described in the above (1) A fragrance composition containing an alkanol,
About.
本発明のシクロヘキシルアルカノールは、あたたかい木様の甘さとすずらんの花を想起させるフローラル香を有し、かつ優れた香気持続性を有する。また、本発明の製造方法によれば、本発明のシクロヘキシルアルカノールを工業的に有利な方法で製造することが可能となる。 The cyclohexyl alkanol of the present invention has a floral fragrance reminiscent of warm wood-like sweetness and suzuran flowers, and has excellent fragrance persistence. Further, according to the production method of the present invention, the cyclohexyl alkanol of the present invention can be produced by an industrially advantageous method.
[シクロヘキシルアルカノール]
本発明は、下記一般式(I)で表されるシクロヘキシルアルカノールに関する。
[Cyclohexylalkanol]
The present invention relates to a cyclohexylalkanol represented by the following general formula (I).
一般式(I)中、R1で示される炭素数2〜4の炭化水素基としては、それぞれ炭素数2〜4のアルキル基、アルケニル基、及びアルキニル基を挙げることができる。炭素数2〜4のアルキル基としては、エチル基、n−プロピル基、イソプロピル基、n−ブチル基、イソブチル基、sec−ブチル基、tert−ブチル基が挙げられる。炭素数2〜4のアルケニル基としては、ビニル基、アリル基、2−ブテニル基、2−メチル−2−プロペニル基等が挙げられる。炭素数2〜4のアルキニル基としては、エチニル基、2−プロピニル基、2−ブチニル基等が挙げられる。これらのうちR1としては、匂いの強さと質の観点から、エチル基、n−プロピル基、イソプロピル基、ビニル基、アリル基、エチニル基、2−プロピニル基が好ましく、エチル基、n−プロピル基、イソプロピル基、ビニル基、アリル基が更に好ましく、特にエチル基またはイソプロピル基が好ましい。 In the general formula (I), examples of the hydrocarbon group having 2 to 4 carbon atoms represented by R 1 include an alkyl group having 2 to 4 carbon atoms, an alkenyl group, and an alkynyl group. Examples of the alkyl group having 2 to 4 carbon atoms include ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, and tert-butyl group. Examples of the alkenyl group having 2 to 4 carbon atoms include a vinyl group, an allyl group, a 2-butenyl group, and a 2-methyl-2-propenyl group. Examples of the alkynyl group having 2 to 4 carbon atoms include an ethynyl group, a 2-propynyl group, and a 2-butynyl group. Of these, R 1 is preferably an ethyl group, n-propyl group, isopropyl group, vinyl group, allyl group, ethynyl group, or 2-propynyl group from the viewpoint of odor intensity and quality, and ethyl group, n-propyl group. Group, isopropyl group, vinyl group and allyl group are more preferable, and ethyl group or isopropyl group is particularly preferable.
R2で示される炭素数1〜4の炭化水素基としては、メチル基、エチル基、n−プロピル基、イソプロピル基、n−ブチル基、イソブチル基、sec−ブチル基、ビニル基、アリル基、2−ブテニル基、2−メチル−2−プロペニル基、エチニル基、2−プロピニル基、2−ブチニル基等が挙げられる。R2としては、匂いの拡散性の観点から、水素原子、メチル基、エチル基、n−プロピル基、イソプロピル基、ビニル基、アリル基、エチニル基、2−プロピニル基が好ましく、水素原子、メチル基、エチル基、ビニル基がより好ましく、水素原子、メチル基が更に好ましく水素原子が特に好ましい。
本発明においては、一般式(I)で表されるシクロヘキシルアルカノールとして、R1がエチル基またはイソプロピル基であり、かつR2が水素原子であるものが好ましい。
上記のような一般式(I)で表されるシクロヘキシルアルカノールは、あたたかい木様の甘さとすずらんの花を想起させるフローラル香を有し、かつ優れた香気持続性を有することから、香料組成物に好ましく含有させることができる。
Examples of the hydrocarbon group having 1 to 4 carbon atoms represented by R 2 include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, vinyl group, allyl group, Examples include 2-butenyl group, 2-methyl-2-propenyl group, ethynyl group, 2-propynyl group, 2-butynyl group and the like. R 2 is preferably a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a vinyl group, an allyl group, an ethynyl group, or a 2-propynyl group from the viewpoint of odor diffusibility. Group, ethyl group and vinyl group are more preferred, hydrogen atom and methyl group are still more preferred, and hydrogen atom is particularly preferred.
In the present invention, the cyclohexyl alkanol represented by the general formula (I) is preferably one in which R 1 is an ethyl group or an isopropyl group and R 2 is a hydrogen atom.
The cyclohexyl alkanol represented by the general formula (I) as described above has a floral fragrance reminiscent of warm wood-like sweetness and suzuran flowers, and has an excellent fragrance persistence. It can be preferably contained.
本発明のシクロヘキシルアルカノールは、六員環上の4位のイソプロピル基と1位のアルカノール基の相対配置により、シス体とトランス体の混合物として得られる場合がある。本発明において、シクロヘキシルアルカノールは、シス体とトランス体それぞれ単独のものあってもよいが、任意の比率の混合物であってもよい。匂いのフローラルらしさから、シス体とトランス体の含有比率は質量比率でシス体:トランス体=100:0〜10:90が好ましく、100:0〜50:50が更に好ましい。 The cyclohexyl alkanol of the present invention may be obtained as a mixture of a cis isomer and a trans isomer due to the relative arrangement of the 4-position isopropyl group and the 1-position alkanol group on the six-membered ring. In the present invention, the cyclohexyl alkanol may be a single cis isomer or a trans isomer, but may be a mixture in any ratio. In view of the floral nature of the odor, the content ratio of the cis isomer to the trans isomer is preferably cis isomer: trans isomer = 100: 0 to 10:90, more preferably 100: 0 to 50:50 in terms of mass ratio.
[シクロヘキシルアルカノールの製造方法]
本発明の一般式(I)で表されるシクロヘキシルアルカノールは、例えば前記一般式(III)で表されるカルボニル化合物を還元することにより得ることができる。
一般式(III)で表されるカルボニル化合物は、前記一般式(II)で表される化合物を用いて、例えば、一般式(II)で表される化合物をアルキル化、アルケニル化、アルキニル化等することにより得られる。
R3が水素原子であるアルデヒド化合物の場合、一般式(III)で表されるカルボニル化合物は、例えば以下の式(A)に示すように、一般式(II)で表される4−イソプロピル−1−カルボニル化合物に、塩基性化合物の存在下で、アルキル化剤、アルケニル化剤、アルキニル化剤等、好ましくはアルキル化剤またはアルケニル化剤、更に好ましくはアルキル化剤を反応させて得ることができる。
[Method for producing cyclohexylalkanol]
The cyclohexyl alkanol represented by the general formula (I) of the present invention can be obtained, for example, by reducing the carbonyl compound represented by the general formula (III).
For the carbonyl compound represented by the general formula (III), the compound represented by the general formula (II) is used, for example, the compound represented by the general formula (II) is alkylated, alkenylated, alkynylated, etc. Can be obtained.
In the case of an aldehyde compound in which R 3 is a hydrogen atom, the carbonyl compound represented by the general formula (III) is, for example, 4-isopropyl- represented by the general formula (II) as shown in the following formula (A): It can be obtained by reacting a 1-carbonyl compound with an alkylating agent, alkenylating agent, alkynylating agent, etc., preferably an alkylating agent or alkenylating agent, more preferably an alkylating agent in the presence of a basic compound. it can.
塩基性化合物としては、具体的には水酸化リチウム、水酸化ナトリウム、水酸化カリウム、水酸化カルシウム、水酸化マグネシウム、水酸化バリウムなどの金属水酸化物、炭酸水素ナトリウム、炭酸ナトリウムなどの金属炭酸塩、リチウム、ナトリウム、カリウム、マグネシウムなどの金属、リチウムジイソプロピルアミドなどの金属アミド、n−ブチルリチウム、tert−ブチルリチウムなどのアルキル金属、水素化ナトリウム、水素化カリウム、水素化ホウ素ナトリウム、水素化リチウムアルミニウムなどの金属水素化物、酸化ナトリウム、酸化マグネシウムなどの金属酸化物、アンモニア、メチルアミン、ブチルアミン、ジブチルアミン、トリブチルアミン、ピロリジン、ピリジンなどのアミン類、ナトリウムメトキシド、ナトリウムエトキシド、カリウムtert−ブトキシド等の金属アルコキシドなどが挙げられる。
塩基性化合物の使用量は、反応収率の観点から、原料となる一般式(II)で表されるカルボニル化合物に対して10〜1000モル%の範囲が好ましく、50〜500モル%の範囲がより好ましい。
Specific examples of basic compounds include metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, magnesium hydroxide, and barium hydroxide, and metal carbonates such as sodium bicarbonate and sodium carbonate. Salts, metals such as lithium, sodium, potassium, magnesium, metal amides such as lithium diisopropylamide, alkyl metals such as n-butyllithium and tert-butyllithium, sodium hydride, potassium hydride, sodium borohydride, hydrogenated Metal hydrides such as lithium aluminum, metal oxides such as sodium oxide and magnesium oxide, amines such as ammonia, methylamine, butylamine, dibutylamine, tributylamine, pyrrolidine and pyridine, sodium methoxide, sodium Ethoxide, and metal alkoxides such as potassium tert- butoxide.
The amount of the basic compound used is preferably in the range of 10 to 1000 mol%, more preferably in the range of 50 to 500 mol% with respect to the carbonyl compound represented by the general formula (II) as a raw material from the viewpoint of reaction yield. More preferred.
上記式(A)に示される反応に用いられるR1Xで表わされるアルキル化剤、アルケニル化剤及びアルキニル化剤としては、その各々が炭素数2〜4である、アルキル基、アルケニル基、アルキニル基をそれぞれ有する化合物が挙げられる。このような化合物としては、いずれも公知のものが使用可能であるが、好ましくは、炭素数2〜4のアルキル基またはアルケニル基、更に好ましくは炭素数2〜4のアルキル基を有する化合物である。具体的には、塩化エチル、臭化エチル、ヨウ化エチル、塩化イソプロピル、臭化イソプロピル、ヨウ化イソプロピル、臭化n−ブチル、ヨウ化n−ブチル、臭化tert−ブチル、ヨウ化tert−ブチル、塩化ビニル、臭化アリル、臭化プロパルギル等のハロゲン化アルキルや、ジエチル硫酸、ジプロピル硫酸等のアルキル硫酸や、プロパルギルベンゼンスルホネート等のスルホネートが好ましく挙げられる。この中で、反応性の観点から、ハロゲン化アルキル、ハロゲン化アルケニル、ハロゲン化アルキニルまたはアルキル硫酸がより好ましく、ハロゲン化アルキル、ハロゲン化アルケニルまたはアルキル硫酸が更に好ましく、ハロゲン化アルキルまたはアルキル硫酸が特に好ましい。
R1Xで表わされる上記化合物の使用量は、反応収率の観点から、原料となる一般式(II)で表されるカルボニル化合物に対して10〜1000モル%が好ましく、50〜500モル%がより好ましい。
Examples of the alkylating agent, alkenylating agent and alkynylating agent represented by R 1 X used in the reaction represented by the above formula (A) include an alkyl group, an alkenyl group and an alkynyl each having 2 to 4 carbon atoms. Examples thereof include compounds each having a group. Any known compound can be used as such a compound, but preferably a compound having an alkyl group or alkenyl group having 2 to 4 carbon atoms, more preferably an alkyl group having 2 to 4 carbon atoms. . Specifically, ethyl chloride, ethyl bromide, ethyl iodide, isopropyl chloride, isopropyl bromide, isopropyl iodide, n-butyl bromide, n-butyl iodide, tert-butyl bromide, tert-butyl iodide Preferred are alkyl halides such as vinyl chloride, allyl bromide and propargyl bromide, alkyl sulfates such as diethyl sulfate and dipropyl sulfate, and sulfonates such as propargyl benzene sulfonate. Among these, from the viewpoint of reactivity, alkyl halide, alkenyl halide, alkynyl halide or alkylsulfuric acid is more preferable, alkyl halide, alkenyl halide or alkylsulfuric acid is more preferable, and alkyl halide or alkylsulfuric acid is particularly preferable. preferable.
The amount of the above compound represented by R 1 X is preferably 10 to 1000 mol%, preferably 50 to 500 mol%, based on the carbonyl compound represented by the general formula (II) as a raw material, from the viewpoint of reaction yield. Is more preferable.
上記式(A)で示される反応は、無溶媒下で行うこともできるが、有機溶媒を用いて行うこともできる。有機溶媒としては、塩基性条件下で使用できる溶媒であれば特に限定されず、ジクロロメタン等のハロゲン化炭化水素溶媒、テトラヒドロフラン、ジエチルエーテル等のエーテル系溶媒、ヘキサン等の脂肪族炭化水素系溶媒、ベンゼン、トルエン等の芳香族炭化水素系溶媒等が挙げられる。
反応温度は、通常−78〜110℃であり、−20〜100℃が好ましく、0〜80℃がより好ましい。
なお、一般式(II)で表されるカルボニル化合物は、公知の方法で製造することができる。
The reaction represented by the above formula (A) can be carried out in the absence of a solvent, but can also be carried out using an organic solvent. The organic solvent is not particularly limited as long as it can be used under basic conditions, a halogenated hydrocarbon solvent such as dichloromethane, an ether solvent such as tetrahydrofuran and diethyl ether, an aliphatic hydrocarbon solvent such as hexane, Examples include aromatic hydrocarbon solvents such as benzene and toluene.
The reaction temperature is usually −78 to 110 ° C., preferably −20 to 100 ° C., more preferably 0 to 80 ° C.
In addition, the carbonyl compound represented by general formula (II) can be manufactured by a well-known method.
R3が炭素数1〜4の炭化水素基であるケトン化合物である場合、一般式(III)で表されるカルボニル化合物は、例えば第5版 実験化学講座15(丸善株式会社)300〜313頁記載のケトンのα位のアルキル化法を用いて製造することができる。
また、R3がOR4であるカルボン酸またはエステルである場合、一般式(III)で表されるカルボニル化合物は、例えば第5版 実験化学講座16(丸善株式会社)47〜50頁記載のエステルのα位のアニオンを利用する方法で製造することができる。
When R 3 is a ketone compound that is a hydrocarbon group having 1 to 4 carbon atoms, the carbonyl compound represented by the general formula (III) is, for example, 5th edition Experimental Chemistry Lecture 15 (Maruzen Co., Ltd.), pages 300 to 313. It can be prepared using the described alkylation method at the α-position of the ketone.
When R 3 is OR 4 carboxylic acid or ester, the carbonyl compound represented by the general formula (III) is, for example, the ester described in pages 5-50 of 5th edition Experimental Chemistry Course 16 (Maruzen Co., Ltd.). The α-position anion can be used for the production.
一般式(I)で表されるシクロアルカノールは、以下の式(B)で示されるように、上記一般式(III)で表されるカルボニル化合物を還元して製造することができる。 The cycloalkanol represented by the general formula (I) can be produced by reducing the carbonyl compound represented by the general formula (III) as shown by the following formula (B).
一般式(III)で表されるカルボニル化合物の還元は、通常カルボニル化合物をアルコールに還元する際に用いられる方法であればいずれも使用でき特に限定されないが、例えば第5版 実験化学講座14巻(丸善株式会社)1〜49頁記載のヒドリド還元、金属および金属塩による還元、接触水素化、水素移動反応による還元、微生物または酵素による還元などをいずれも用いることができる。この中で、R3が水素原子または炭素数1〜4の炭化水素基である場合には、反応収率の観点から、ヒドリド還元、または接触水素化、水素移動反応による還元が好ましく用いられ、R3が前記OR4である場合にはヒドリド還元または接触水素化による還元が好ましく用いられる。 The reduction of the carbonyl compound represented by the general formula (III) is not particularly limited as long as it is a method usually used for reducing a carbonyl compound to an alcohol. For example, the 5th edition Experimental Chemistry Course Vol. 14 ( (Maruzen Co., Ltd.) Any of hydride reduction described in pages 1 to 49, reduction with metals and metal salts, catalytic hydrogenation, reduction by hydrogen transfer reaction, reduction with microorganisms or enzymes, and the like can be used. Among these, when R 3 is a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms, from the viewpoint of reaction yield, hydride reduction, or catalytic hydrogenation, reduction by hydrogen transfer reaction is preferably used, When R 3 is OR 4 , hydride reduction or reduction by catalytic hydrogenation is preferably used.
上記ヒドリド還元に用いられる還元剤としては通常用いられるものであれば特に限定されず、例えば、水素化ほう素ナトリウム、水素化ほう素リチウム、ジボラン、水素化リチウムアルミニウム、水素化ジイソブチルアルミニウム、ナトリウム水素化ビス(メトキシエトキシ)アルミニウム等の還元剤を用いることができる。このうち、R3が水素原子または炭素数1〜4の炭化水素基である場合には、取り扱いの容易さから水素化ほう素ナトリウムまたは水素化ほう素リチウムが好ましい。還元剤の使用量は特に限定されないが、原料のカルボニル化合物に対して0.5〜5当量用いることが好ましく、経済性の観点から0.5〜2当量使用することがより好ましい。
反応は無溶媒下で行うこともできるが、反応速度制御の容易さから溶媒を用いることが好ましい。溶媒は実質的に上記式(B)の反応に対し不活性なものであれば特に限定されないが、例えば、ヘキサン、ベンゼン、トルエン、シクロヘキサン、ジエチルエーテル、テトラヒドロフラン、ジエチレングリコールジメチルエーテル、塩化メチレン、クロロホルム、四塩化炭素などが挙げられる。
反応温度は特に限定されないが、−78〜150℃で行うことが好ましく、−20〜100℃で行うことがより好ましい。
The reducing agent used for the hydride reduction is not particularly limited as long as it is usually used. For example, sodium borohydride, lithium borohydride, diborane, lithium aluminum hydride, diisobutylaluminum hydride, sodium hydrogen A reducing agent such as bis (methoxyethoxy) aluminum chloride can be used. Among these, when R 3 is a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms, sodium borohydride or lithium borohydride is preferable because of easy handling. Although the usage-amount of a reducing agent is not specifically limited, It is preferable to use 0.5-5 equivalent with respect to the carbonyl compound of a raw material, and it is more preferable to use 0.5-2 equivalent from a viewpoint of economical efficiency.
Although the reaction can be carried out in the absence of a solvent, it is preferable to use a solvent because of easy control of the reaction rate. The solvent is not particularly limited as long as it is substantially inert to the reaction of the above formula (B). For example, hexane, benzene, toluene, cyclohexane, diethyl ether, tetrahydrofuran, diethylene glycol dimethyl ether, methylene chloride, chloroform, four Examples include carbon chloride.
Although reaction temperature is not specifically limited, It is preferable to carry out at -78-150 degreeC, and it is more preferable to carry out at -20-100 degreeC.
接触水素化による還元は、カルボニル化合物からアルコールへの水素化の際の一般的な条件で行うことができるが、好ましくは、周期律表第8〜11属の金属から選ばれる少なくとも1種を含む触媒の存在下で、水素を用いて行うことができる。
周期律表第8〜11属の金属としては、具体的には鉄、コバルト、ニッケル、銅、ルテニウム、ロジウム、パラジウム、銀、オスミウム、イリジウム、白金、金が挙げられ、中でも、触媒活性の観点から、鉄、コバルト、ニッケル、銅、ルテニウム、パラジウム、オスミウム、イリジウム、及び白金が好ましい。
触媒の使用量は特に限定されないが、原料となる一般式(III)で表されるカルボニル化合物に対して金属質量換算で0.0001〜50質量%が好ましく、0.005〜20質量%がより好ましく、0.001〜10質量%が特に好ましい。
この際の反応圧力は、通常0.1〜40MPaであり、0.2〜30MPaが好ましい。反応温度は、通常0〜400℃であり、20〜300℃が好ましい。
The reduction by catalytic hydrogenation can be carried out under the general conditions for hydrogenation of carbonyl compounds to alcohols, but preferably contains at least one selected from metals in groups 8 to 11 of the periodic table. This can be done with hydrogen in the presence of a catalyst.
Specific examples of metals belonging to Groups 8 to 11 of the periodic table include iron, cobalt, nickel, copper, ruthenium, rhodium, palladium, silver, osmium, iridium, platinum, and gold. From the above, iron, cobalt, nickel, copper, ruthenium, palladium, osmium, iridium, and platinum are preferable.
Although the usage-amount of a catalyst is not specifically limited, 0.0001-50 mass% is preferable in conversion of metal mass with respect to the carbonyl compound represented by general formula (III) used as a raw material, and 0.005-20 mass% is more Preferably, 0.001 to 10% by mass is particularly preferable.
The reaction pressure at this time is usually 0.1 to 40 MPa, and preferably 0.2 to 30 MPa. Reaction temperature is 0-400 degreeC normally, and 20-300 degreeC is preferable.
また、上記の水素化反応は無溶媒下で行うこともできるが、メタノール、エタノール、イソプロピルアルコール、tert−ブタノール、ヘキサン、ベンゼン、トルエン、ジエチルエーテル、テトラヒドロフラン等の溶媒を用いて行うこともできる。
本発明の一般式(I)で表されるシクロヘキシルアルカノールは、あたたかい木様の甘さとすずらんの花を想起させるフローラル香を有し、かつ持続性にも優れることから、単独で又は他の成分と組み合わせて、石鹸、シャンプー、リンス、洗剤、化粧品、スプレー製品、芳香剤、香水、入浴剤等の賦香成分として使用できる。
The hydrogenation reaction can be performed in the absence of a solvent, but can also be performed using a solvent such as methanol, ethanol, isopropyl alcohol, tert-butanol, hexane, benzene, toluene, diethyl ether, tetrahydrofuran, or the like.
Since the cyclohexyl alkanol represented by the general formula (I) of the present invention has a warm wood-like sweetness and a floral fragrance reminiscent of a suzuran flower, and is excellent in sustainability, it alone or with other ingredients In combination, it can be used as a perfuming ingredient for soaps, shampoos, rinses, detergents, cosmetics, spray products, fragrances, perfumes, bathing agents and the like.
[香料組成物]
本発明の香料組成物は、一般式(I)で表されるシクロヘキシルアルカノールを含有するものであり、通常用いられる他の香料成分や、所望組成の調合香料に、一般式(I)で表されるシクロヘキシルアルカノールを単独でまたは2種以上を組み合わせて配合して得られるものである。
その配合量は、調合香料の種類、目的とする香気の種類及び香気の強さ等により適宜選択することができるが、調合香料組成物中に0.01〜90質量%を加えることが好ましく、0.1〜50質量%加えることがより好ましい。
[Perfume composition]
The fragrance composition of the present invention contains a cyclohexyl alkanol represented by the general formula (I), and is represented by the general formula (I) in other commonly used fragrance components or a blended fragrance having a desired composition. The cyclohexyl alkanol is obtained by singly or in combination of two or more.
The blending amount can be appropriately selected depending on the type of the blended fragrance, the type of the target fragrance, the intensity of the fragrance, etc., but it is preferable to add 0.01 to 90% by mass in the blended fragrance composition, It is more preferable to add 0.1 to 50% by mass.
本発明の香料組成物において、シクロヘキシルアルカノールと組み合わせて用いることができる香料成分としては、炭化水素類、アルコール類、フェノール類、エステル類、カーボネート類、アルデヒド類、ケトン類、アセタール類、エーテル類、ニトリル類、カルボン酸類、ラクトン類、天然精油や天然抽出物等を挙げることができる。
炭化水素類としては、リモネン、α−ピネン、β−ピネン、テルピネン、セドレン、ロンギフォレン、バレンセン等が挙げられる。
アルコール類としては、リナロール、シトロネロール、ゲラニオール、ネロール、テルピネオール、ジヒドロミルセノール、エチルリナロール、ファルネソール、ネロリドール、シス−3−ヘキセノール、セドロール、メントール、ボルネオール、フェニルエチルアルコール、ベンジルアルコール、ジメチルベンジルカルビノール、フェニルエチルジメチルカルビノール、フェニルヘキサノール、2,2,6−トリメチルシクロヘキシル−3−ヘキサノール、アンバーコア(花王株式会社商品名)等が挙げられる。
In the fragrance composition of the present invention, the fragrance components that can be used in combination with the cyclohexyl alkanol include hydrocarbons, alcohols, phenols, esters, carbonates, aldehydes, ketones, acetals, ethers, Nitriles, carboxylic acids, lactones, natural essential oils, natural extracts and the like can be mentioned.
Examples of the hydrocarbons include limonene, α-pinene, β-pinene, terpinene, cedrene, longifolene, and valencene.
Alcohols include linalool, citronellol, geraniol, nerol, terpineol, dihydromyrcenol, ethyl linalool, farnesol, nerolidol, cis-3-hexenol, cedrol, menthol, borneol, phenylethyl alcohol, benzyl alcohol, dimethylbenzylcarbi Nol, phenylethyldimethylcarbinol, phenylhexanol, 2,2,6-trimethylcyclohexyl-3-hexanol, amber core (trade name of Kao Corporation) and the like.
フェノール類としては、グアヤコール、オイゲノール、イソオイゲノール、チモール、パラクレゾール、バニリン等が挙げられる。
エステル類としては、ギ酸エステル、酢酸エステル、プロピオン酸エステル、酪酸エステル、ノネン酸エステル、安息香酸エステル、桂皮酸エステル、サリチル酸エステル、ブラシル酸エステル、チグリン酸エステル、ジャスモン酸エステル、グリシド酸エステル、アントラニル酸エステル等が挙げられる。
Examples of phenols include guaiacol, eugenol, isoeugenol, thymol, paracresol, vanillin and the like.
Esters include formic acid ester, acetic acid ester, propionic acid ester, butyric acid ester, nonenic acid ester, benzoic acid ester, cinnamic acid ester, salicylic acid ester, brassylic acid ester, tiglic acid ester, jasmonic acid ester, glycidic acid ester, anthranil Acid ester etc. are mentioned.
ギ酸エステルとしては、リナリルホルメート、シトロネリルホルメート、ゲラニルホルメート等、酢酸エステルとしては、n−ヘキシルアセテート、シス−3−ヘキセニルアセテート、リナリルアセテート、シトロネリルアセテート、ゲラニルアセテート、ネリルアセテート、テルピニルアセテート、ノピルアセテート、ボルニルアセテート、イソボルニルアセテート、o−tert−ブチルシクロヘキシルアセテート、p−tert−ブチルシクロヘキシルアセテート、トリシクロデセニルアセテート、ベンジルアセテート、フェニルエチルアセテート、スチラリルアセテート、シンナミルアセテート、ジメチルベンジルカルビニルアセテート、フェニルエチルフェニルアセテート、3−ペンチルテトラヒドロピラン−4−イルアセテート等、パラクレジルフェニルアセテート、プロピオン酸エステルとしては、シトロネリルプロピオネート、トリシクロデセニルプロピオネート、アリルシクロヘキシルプロピオネート、エチル2−シクロヘキシルプロピオネート、ベンジルプロピオネート等、酪酸エステルとしては、シトロネリルブチレート、ジメチルベンジルカルビニルn−ブチレート、トリシクロデセニルイソブチレート等が挙げられる。 As formic acid ester, linalyl formate, citronellyl formate, geranyl formate, etc. As acetic acid ester, n-hexyl acetate, cis-3-hexenyl acetate, linalyl acetate, citronellyl acetate, geranyl acetate, neryl acetate, tellurium acetate Pinyl acetate, nopyrulacetate, bornyl acetate, isobornyl acetate, o-tert-butylcyclohexyl acetate, p-tert-butylcyclohexyl acetate, tricyclodecenyl acetate, benzyl acetate, phenylethyl acetate, styrylyl acetate , Cinnamyl acetate, dimethylbenzylcarbinyl acetate, phenylethylphenyl acetate, 3-pentyltetrahydropyran-4-yl acetate , Paracresyl phenyl acetate, propionate, citronellyl propionate, tricyclodecenyl propionate, allyl cyclohexyl propionate, ethyl 2-cyclohexyl propionate, benzyl propionate, butyrate ester Examples thereof include citronellyl butyrate, dimethylbenzylcarbinyl n-butyrate, tricyclodecenyl isobutyrate and the like.
また、ノネン酸エステルとしては、メチル2−ノネノエート、エチル2−ノネノエート、エチル3−ノネノエート等、安息香酸エステルとしては、メチルベンゾエート、ベンジルベンゾエート、3,6−ジメチルベンゾエート等、メチルシンナメート、桂皮酸エステルとしては、ベンジルシンナメート等、サリチル酸エステルとしては、メチルサリシレート、n−ヘキシルサリシレート、シス−3−ヘキセニルサリシレート、シクロヘキシルサリシレート、ベンジルサリシレート等が挙げられる。 Further, as nonenoic acid ester, methyl 2-nonenoate, ethyl 2-nonenoate, ethyl 3-nonenoate, etc., and as benzoic acid ester, methyl benzoate, benzyl benzoate, 3,6-dimethylbenzoate, etc., methyl cinnamate, cinnamic acid, etc. Examples of the ester include benzyl cinnamate, and examples of the salicylic acid ester include methyl salicylate, n-hexyl salicylate, cis-3-hexenyl salicylate, cyclohexyl salicylate, and benzyl salicylate.
さらに、ブラシル酸エステルとしては、エチレンブラシレート等、チグリン酸エステルとしては、ゲラニルチグレート、1−ヘキシルチグレート、シス−3−ヘキセニルチグレート等、ジャスモン酸エステルとしては、メチルジャスモネート、メチルジヒドロジャスモネート等、グリシド酸エステルとしては、メチル2,4−ジヒドロキシ−エチルメチルフェニルグリシデート、4−メチルフェニルエチルグリシデート等、アントラニル酸エステルとしては、メチルアントラニレート、エチルアントラニレート、ジメチルアントラニレート、フルテート(花王株式会社商品名)等が挙げられる。 Further, as the brassic acid ester, ethylene brushate, etc., as the tiglic acid ester, geranyl tiglate, 1-hexyl tiglate, cis-3-hexenyl tiglate, etc., as the jasmonic acid ester, methyl jasmonate, methyl Dihydrojasmonate, etc., as glycidic acid ester, methyl 2,4-dihydroxy-ethylmethylphenyl glycidate, 4-methylphenylethyl glycidate, etc., as anthranilic acid ester, methyl anthranilate, ethyl anthranilate, Examples thereof include dimethyl anthranilate and full tate (trade name of Kao Corporation).
カーボネート類としては、市販品として、ジャスマシクラット(花王株式会社商品名)、フロラマット(花王株式会社商品名)等が挙げられる。
アルデヒド類としては、n−オクタナール、n−ノナナール、n−デカナ−ル、n−ドデカナ−ル、2−メチルウンデカナール、10−ウンデセナール、シトロネラール、シトラール、ヒドロキシシトロネラール、ベンズアルデヒド、フェニルアセトアルデヒド、フェニルプロピルアルデヒド、シンナミックアルデヒド、ジメチルテトラヒドロベンズアルデヒド、リラール(IFF社、商品名)、2−シクロヘキシルプロパナール、p−tert−ブチル−α−メチルヒドロシンナミックアルデヒド、p−イソプロピル−α−メチルヒドロシンナミックアルデヒド、p−エチル−α,α−ジメチルヒドロシンナミックアルデヒド、α−アミルシンナミックアルデヒド、α−ヘキシルシンナミックアルデヒド、ヘリオトロピン、α−メチル−3,4−メチレンジオキシヒドロシンナミックアルデヒド等が挙げられる。
Examples of carbonates include Jasma Cyclat (trade name of Kao Corporation), Flora Mat (trade name of Kao Corporation), and the like as commercially available products.
Examples of aldehydes include n-octanal, n-nonanal, n-decanal, n-dodecanal, 2-methylundecanal, 10-undecenal, citronellal, citral, hydroxycitronellal, benzaldehyde, phenylacetaldehyde, phenylpropional. Lualdehyde, cinnamic aldehyde, dimethyltetrahydrobenzaldehyde, Lilal (IFF, trade name), 2-cyclohexylpropanal, p-tert-butyl-α-methylhydrocinnamic aldehyde, p-isopropyl-α-methylhydrocinnamic Aldehyde, p-ethyl-α, α-dimethylhydrocinnamic aldehyde, α-amylcinnamic aldehyde, α-hexylcinnamic aldehyde, heliotropin, α-methyl-3,4- Etc. Chi dioxy hydro cinnamic aldehyde and the like.
ケトン類としては、α−イオノン、β−イオノン、γ−イオノン、α−メチルイオノン、β−メチルイオノン、γ−メチルイオノン、ダマセノン、メチルヘプテノン、4−メチレン−3,5,6,6−テトラメチル−2−ヘプタノン、アミルシクロペンタノン、ジヒドロジャスモン、ローズケトン、カルボン、メントン、樟脳、アセチルセドレン、イソロンギフォラノン、ヌートカトン、ベンジルアセトン、アニシルアセトン、メチルβ−ナフチルケトン、2,5−ジメチル−4−ヒドロキシ−3(2H)−フラノン、マルトール、ムスコン、シベトン、シクロペンタデカノン等が挙げられる。 Examples of ketones include α-ionone, β-ionone, γ-ionone, α-methylionone, β-methylionone, γ-methylionone, damasenone, methylheptenone, 4-methylene-3,5,6,6-tetramethyl-2- Heptanone, amylcyclopentanone, dihydrojasmon, rose ketone, carvone, menthone, camphor, acetyl cedrene, isolongifolanone, nootkatone, benzylacetone, anisylacetone, methyl β-naphthylketone, 2,5-dimethyl-4 -Hydroxy-3 (2H) -furanone, maltol, muscone, sibeton, cyclopentadecanone and the like.
アセタール類としては、アセトアルデヒドエチルフェニルプロピルアセタール、シトラールジエチルアセタール、フェニルアセトアルデヒドグリセリンアセタール、エチルアセトアセテートエチレングリコールアセタール、ボアザンブレンフォルテ(花王株式会社商品名)等が挙げられる。
エーテル類としては、セドリルメチルエーテル、アネトール、β−ナフチルメチルエーテル、β−ナフチルエチルエーテル、リモネンオキサイド、ローズオキサイド、ネロールオキサイド、1,8−シネオール、ローズフラン、アンブロキサン(花王株式会社商品名)、ハーバベール(花王株式会社商品名)等が挙げられる。
ニトリル類としては、ゲラニルニトリル、シトロネリルニトリル、ドデカンニトリル等が挙げられる。
Examples of acetals include acetaldehyde ethylphenylpropyl acetal, citral diethyl acetal, phenylacetaldehyde glycerin acetal, ethyl acetoacetate ethylene glycol acetal, boazan brenforte (trade name of Kao Corporation), and the like.
Examples of ethers include cedol methyl ether, anethole, β-naphthyl methyl ether, β-naphthyl ethyl ether, limonene oxide, rose oxide, nerol oxide, 1,8-cineole, rose furan, ambroxan (product of Kao Corporation) Name) and Herbaval (trade name of Kao Corporation).
Examples of nitriles include geranyl nitrile, citronellyl nitrile, and dodecane nitrile.
カルボン酸類としては、安息香酸、フェニル酢酸、桂皮酸、ヒドロ桂皮酸、酪酸、2−ヘキセン酸等が挙げられる。
ラクトン類としては、γ−デカラクトン、δ−デカラクトン、γ−バレロラクトン、γ−ノナラクトン、γ−ウンデカラクトン、δ−ヘキサラクトン、γ−ジャスモラクトン、ウイスキーラクトン、クマリン、シクロペンタデカノリド、シクロヘキサデカノリド、アンブレットリド、11−オキサヘキサデカノリド、ブチリデンフタリド等が挙げられる。
Examples of carboxylic acids include benzoic acid, phenylacetic acid, cinnamic acid, hydrocinnamic acid, butyric acid, and 2-hexenoic acid.
Examples of lactones include γ-decalactone, δ-decalactone, γ-valerolactone, γ-nonalactone, γ-undecalactone, δ-hexalactone, γ-jasmolactone, whiskey lactone, coumarin, cyclopentadecanolide, Examples include cyclohexadecanolide, ambretlide, 11-oxahexadecanolide, butylidenephthalide, and the like.
天然精油や天然抽出物としては、オレンジ、レモン、ライム、ベルガモット、バニラ、マンダリン、ペパーミント、スペアミント、ラベンダー、カモミル、ローズマリー、ユーカリ、セージ、バジル、ローズ、ロックローズ、ゼラニウム、ジャスミン、イランイラン、アニス、クローブ、ジンジャー、ナツメグ、カルダモン、セダー、ヒノキ、ベチバー、パチュリ、レモングラス、ラブダナム等が挙げられる。 Natural essential oils and natural extracts include orange, lemon, lime, bergamot, vanilla, mandarin, peppermint, spearmint, lavender, camomil, rosemary, eucalyptus, sage, basil, rose, rock rose, geranium, jasmine, ylang ylang, Anise, cloves, ginger, nutmeg, cardamom, cedar, cypress, vetiver, patchouli, lemongrass, lovedanum and the like.
試料の同定
以下の実施例等で得られたシクロヘキシルアルカノールの構造を、核磁気共鳴スペクトル(1H−NMR)により同定した。核磁気共鳴スペクトルは、溶媒としてクロロホルム−dを用いて、Varian社製のMercury 400により測定した。
Identification of Sample The structure of cyclohexylalkanol obtained in the following Examples and the like was identified by nuclear magnetic resonance spectrum ( 1 H-NMR). The nuclear magnetic resonance spectrum was measured by Mercury 400 manufactured by Varian, using chloroform-d as a solvent.
実施例1(1−エチル−4−イソプロピルシクロヘキシルメタノールの合成)
フラスコにカリウムtert−ブトキシド19gとテトラヒドロフラン40gを入れ0℃で数分間攪拌した後、4−イソプロピルシクロヘキサンカルバルデヒド20gを0℃下2.5時間かけて滴下した。その後、ブロモエタン22gを0℃下3時間かけて滴下した。0℃下30分攪拌後、室温まで昇温を行い更に30分攪拌した。その反応液を水40gで3回洗浄し、硫酸マグネシウムを加えて乾燥、濾過、濃縮を行い、アルデヒド混合物21gを得た。そのアルデヒド混合物を、圧力70〜150Pa、温度60〜85℃の条件で蒸留し、1−エチル−4−イソプロピルシクロヘキサンカルバルデヒド17g得た。
Example 1 (Synthesis of 1-ethyl-4-isopropylcyclohexylmethanol)
A flask was charged with 19 g of potassium tert-butoxide and 40 g of tetrahydrofuran and stirred at 0 ° C. for several minutes, and then 20 g of 4-isopropylcyclohexanecarbaldehyde was added dropwise at 0 ° C. over 2.5 hours. Thereafter, 22 g of bromoethane was added dropwise at 0 ° C. over 3 hours. After stirring at 0 ° C. for 30 minutes, the mixture was warmed to room temperature and further stirred for 30 minutes. The reaction solution was washed with 40 g of water three times, added with magnesium sulfate, dried, filtered and concentrated to obtain 21 g of an aldehyde mixture. The aldehyde mixture was distilled under the conditions of a pressure of 70 to 150 Pa and a temperature of 60 to 85 ° C. to obtain 17 g of 1-ethyl-4-isopropylcyclohexanecarbaldehyde.
フラスコに窒素雰囲気下でメタノール9gと1.5%水酸化ナトリウム水溶液3gと水素化ほう素ナトリウム2gを入れ、5〜25℃で上記で得られた1−エチル−4−イソプロピルシクロヘキサンカルバルデヒド9gを加えた。20〜25℃で、1.5時間攪拌を続けた後に、反応液に少量の10%硫酸を加えてからエーテル抽出、重曹水での水洗、溶媒留去を行った後にシリカゲルカラムでの分画と蒸留で精製して、1−エチル−4−イソプロピルシクロヘキシルメタノール6gを得た(シス体:トランス体(質量比率)=94:6)
得られた1−エチル−4−イソプロピルシクロヘキシルメタノールは、天然のすずらんの香りを想起させるフレッシュでホワイトフロラール様のニュアンスを伴うフローラル香気を有し、木様の甘さとあたたかさを感じさせ、持続性に優れていた。また、同定した結果は以下の通りである。
1H-NMR(CDCl3, 400MHz, δppm) : 0.79(t, トランス-3H, J=7.6Hz), 0.83(t, シス-3H, J=7.6Hz), 0.85(t, 6H, J=6.8Hz), 1.00(br, 1H), 1.03-1.11(m, 4H), 1.28(q, 2H, J=7.6Hz), 1.38-1.44(m, 2H), 1.49-1.53(m, 2H), 1.58-1.61(m, 2H), 3.30(s, トランス-2H), 3.53(s, シス-2H)
Under a nitrogen atmosphere, 9 g of methanol, 3 g of a 1.5% aqueous sodium hydroxide solution and 2 g of sodium borohydride were placed in a flask, and 9 g of 1-ethyl-4-isopropylcyclohexanecarbaldehyde obtained above at 5 to 25 ° C. added. After stirring for 1.5 hours at 20 to 25 ° C., a small amount of 10% sulfuric acid was added to the reaction solution, followed by ether extraction, water washing with sodium bicarbonate water, solvent distillation, and fractionation on a silica gel column. And 6 g of 1-ethyl-4-isopropylcyclohexylmethanol (cis isomer: trans isomer (mass ratio) = 94: 6).
The resulting 1-ethyl-4-isopropylcyclohexylmethanol has a floral fragrance with a fresh, white-floral-like nuance reminiscent of the natural suzuran fragrance, making it feel like woody sweetness and warmth. It was excellent in nature. The identified results are as follows.
1 H-NMR (CDCl 3 , 400 MHz, δ ppm): 0.79 (t, trans-3H, J = 7.6 Hz), 0.83 (t, cis-3H, J = 7.6 Hz), 0.85 (t, 6H, J = 6.8 Hz), 1.00 (br, 1H), 1.03-1.11 (m, 4H), 1.28 (q, 2H, J = 7.6Hz), 1.38-1.44 (m, 2H), 1.49-1.53 (m, 2H), 1.58 -1.61 (m, 2H), 3.30 (s, Trans-2H), 3.53 (s, Cis-2H)
実施例2(1,4−ジイソプロピルシクロヘキシルメタノールの合成)
フラスコにカリウムtert−ブトキシド14gとテトラヒドロフラン30gを入れ0℃で数分間攪拌した後、4−イソプロピルシクロヘキサンカルバルデヒド15gを0℃下2.5時間かけて滴下した。その後、2−ヨードプロパン25gを0℃下3時間かけて滴下した。0℃下30分攪拌後、室温まで昇温し、更に30分攪拌した。その反応液を水30gで3回洗浄し、硫酸マグネシウムを加えて乾燥、濾過、濃縮を行い、アルデヒド混合物13gを得た。そのアルデヒド混合物13gを、シリカゲルカラムクロマトグラフィー(展開溶媒:n−ヘキサン/酢酸エチル=50/1)で精製し、1,4−ジイソプロピルシクロヘキサンカルバルデヒド3g得た。
Example 2 (Synthesis of 1,4-diisopropylcyclohexylmethanol)
After 14 g of potassium tert-butoxide and 30 g of tetrahydrofuran were added to the flask and stirred at 0 ° C. for several minutes, 15 g of 4-isopropylcyclohexanecarbaldehyde was added dropwise at 0 ° C. over 2.5 hours. Thereafter, 25 g of 2-iodopropane was added dropwise at 0 ° C. over 3 hours. After stirring at 0 ° C. for 30 minutes, the mixture was warmed to room temperature and further stirred for 30 minutes. The reaction solution was washed with 30 g of water three times, added with magnesium sulfate, dried, filtered and concentrated to obtain 13 g of an aldehyde mixture. 13 g of the aldehyde mixture was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate = 50/1) to obtain 3 g of 1,4-diisopropylcyclohexanecarbaldehyde.
フラスコに窒素雰囲気下でメタノール0.7gと1.5%水酸化ナトリウム水溶液0.3gと水素化ほう素ナトリウム0.2gを入れ、0〜25℃で上記で得られた1,4−ジイソプロピルシクロヘキサンカルバルデヒド0.7gを加えた。20〜25℃で2時間攪拌を続けた後に、反応液に少量の10%硫酸を加えてからエーテル抽出、重曹水での水洗、溶媒留去を行って、1,4−ジイソプロピルシクロヘキシルメタノール0.3gを得た(シス体:トランス体(質量比率)=91:9)
得られた1,4−ジイソプロピルシクロヘキシルメタノールは、天然のすずらんの香りを想起させるフレッシュで甘さを伴うフローラル香気を有し、持続性に優れていた。また、同定した結果は以下の通りである。
1H-NMR(CDCl3, 400MHz, δppm) : 0.85(d, シス-6H, J=6.8Hz), 0.87(d, トランス-6H, J=6.8Hz), 0.88(d, シス-6H, J=6.8Hz), 0.89(d, トランス-6H, J=6.8Hz), 0.96-1.01(m, 1H), 1.08(ddd, 2H, J=24, 12, 2.4Hz), 1.18(br, 1H), 1.20(ddd, 2H, J=27, 14, 2.8Hz), 1.41(qd, 1H, J=6.4, 6.4Hz), 1.50-1.53(br, 4H), 1.60(q, 1H, J=6.8Hz), 1.62(q, 1H, J=6.8Hz), 3.40(s, トランス-2H), 3.62(s, シス-2H)
Under a nitrogen atmosphere, 0.7 g of methanol, 0.3 g of a 1.5% aqueous sodium hydroxide solution and 0.2 g of sodium borohydride were placed in a flask, and 1,4-diisopropylcyclohexane obtained above at 0 to 25 ° C. Carbaldehyde 0.7g was added. After stirring at 20 to 25 ° C. for 2 hours, a small amount of 10% sulfuric acid was added to the reaction solution, followed by extraction with ether, washing with aqueous sodium bicarbonate, and evaporation of the solvent to obtain 1,4-diisopropylcyclohexyl methanol. 3 g was obtained (cis isomer: trans isomer (mass ratio) = 91: 9).
The obtained 1,4-diisopropylcyclohexylmethanol had a fresh and sweet floral fragrance reminiscent of the natural suzuran fragrance, and was excellent in sustainability. The identified results are as follows.
1 H-NMR (CDCl 3 , 400MHz, δppm): 0.85 (d, cis-6H, J = 6.8Hz), 0.87 (d, trans-6H, J = 6.8Hz), 0.88 (d, cis-6H, J = 6.8Hz), 0.89 (d, transformer-6H, J = 6.8Hz), 0.96-1.01 (m, 1H), 1.08 (ddd, 2H, J = 24, 12, 2.4Hz), 1.18 (br, 1H) , 1.20 (ddd, 2H, J = 27, 14, 2.8Hz), 1.41 (qd, 1H, J = 6.4, 6.4Hz), 1.50-1.53 (br, 4H), 1.60 (q, 1H, J = 6.8Hz ), 1.62 (q, 1H, J = 6.8Hz), 3.40 (s, transformer-2H), 3.62 (s, cis-2H)
実施例3(1−エチル−4−イソプロピルシクロヘキシルメタノールを用いた処方例)
実施例1で得られた1−エチル−4−イソプロピルシクロヘキシルメタノールを用いて、第1表に示すように配合し、甘さのあるローズ様の香料組成物を調製した。第1表中の数値は質量部である(以下同じ)。
Example 3 (Formulation example using 1-ethyl-4-isopropylcyclohexyl methanol)
Using 1-ethyl-4-isopropylcyclohexylmethanol obtained in Example 1, blended as shown in Table 1 to prepare a sweet rose-like fragrance composition. The numerical values in Table 1 are parts by mass (the same applies hereinafter).
比較例1(比較処方例)
実施例3において、1−エチル−4−イソプロピルシクロヘキシルメタノールを配合せず、ジプロピレングリコールの量を37質量部とした以外は同様にして香料組成物を調製した。
Comparative Example 1 (Comparative formulation example)
In Example 3, a fragrance composition was prepared in the same manner except that 1-ethyl-4-isopropylcyclohexylmethanol was not blended and the amount of dipropylene glycol was changed to 37 parts by mass.
比較例1の甘さのあるローズ様の調合香料に対し、実施例3においては、1−エチル−4−イソプロピルシクロヘキシルメタノール20質量部を配合したことにより、フローラルな甘さとあたたかさが強調され、かつ持続性に優れたローズ様の調合香料が得られた。 In contrast to the sweet rose-like blended fragrance of Comparative Example 1, in Example 3, by blending 20 parts by mass of 1-ethyl-4-isopropylcyclohexylmethanol, floral sweetness and warmth are emphasized, In addition, a rose-like blended fragrance excellent in sustainability was obtained.
実施例4(1,4−ジイソプロピルシクロヘキシルメタノールを用いた処方例)
実施例2で得られた1,4−ジイソプロピルシクロヘキシルメタノールを用いて、第2表に示すように配合し、みずみずしいジャスミン様の製品用香料を調製した。
Example 4 (formulation example using 1,4-diisopropylcyclohexyl methanol)
Using 1,4-diisopropylcyclohexylmethanol obtained in Example 2, it was blended as shown in Table 2 to prepare a fresh jasmine-like product fragrance.
比較例2(比較処方例)
実施例4において、1,4−ジイソプロピルシクロヘキシルメタノールを配合せず、ジプロピレングリコールの量を47.7質量部とした以外は同様にして香料組成物を調製した。
Comparative Example 2 (Comparative formulation example)
In Example 4, a fragrance composition was prepared in the same manner except that 1,4-diisopropylcyclohexylmethanol was not added and the amount of dipropylene glycol was changed to 47.7 parts by mass.
比較例2のみずみずしいジャスミン様の調合香料に対し、実施例4においては、1,4−ジイソプロピルシクロヘキシルメタノール 30質量部を配合したことにより、フレッシュ感のある甘さとあたたかさが強調され、かつ持続性に優れたジャスミン様の調合香料が得られた。 The fresh jasmine-like blended fragrance in Comparative Example 2 was blended with 30 parts by weight of 1,4-diisopropylcyclohexylmethanol in Example 4, thereby emphasizing a fresh sweetness and warmth and sustainability. An excellent jasmine-like fragrance was obtained.
本発明のシクロヘキシルアルカノールは、あたたかい木様の甘さとすずらんの花を想起させるフローラル香を有し、調合香料に木様のあたたかさや甘さとフローラル香気を付与することができることから、トイレタリー用品等への賦香成分として香料組成物に好適に使用できる。 The cyclohexyl alkanol of the present invention has a floral fragrance reminiscent of warm wood-like sweetness and suzuran flowers, and can impart warm, sweetness and floral fragrance of wood-like to the blended fragrance. It can be used suitably for a fragrance composition as a fragrance component.
Claims (3)
で表されるシクロヘキシルアルカノール。 Formula (I)
A cyclohexyl alkanol represented by:
で表されるカルボニル化合物を用いて、一般式(III)
で表されるカルボニル化合物を得た後に還元を行う、一般式(I)
で表されるシクロヘキシルアルカノールの製造方法。 Formula (II)
Using a carbonyl compound represented by general formula (III)
Reduction is performed after obtaining the carbonyl compound represented by the general formula (I)
The manufacturing method of the cyclohexyl alkanol represented by these.
で表されるシクロヘキシルアルカノールを含有する香料組成物。 Formula (I)
The fragrance | flavor composition containing cyclohexyl alkanol represented by these.
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