JP7247190B2 - 匂い物質を含む組成物 - Google Patents
匂い物質を含む組成物 Download PDFInfo
- Publication number
- JP7247190B2 JP7247190B2 JP2020529814A JP2020529814A JP7247190B2 JP 7247190 B2 JP7247190 B2 JP 7247190B2 JP 2020529814 A JP2020529814 A JP 2020529814A JP 2020529814 A JP2020529814 A JP 2020529814A JP 7247190 B2 JP7247190 B2 JP 7247190B2
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- JP
- Japan
- Prior art keywords
- methyl
- oil
- formula
- carbon atoms
- 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.)
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- 239000000203 mixture Substances 0.000 title claims description 78
- 239000003205 fragrance Substances 0.000 title claims description 64
- 150000001875 compounds Chemical class 0.000 claims description 51
- 125000004432 carbon atom Chemical group C* 0.000 claims description 50
- 239000000796 flavoring agent Substances 0.000 claims description 41
- 235000019634 flavors Nutrition 0.000 claims description 41
- 230000000873 masking effect Effects 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 125000005336 allyloxy group Chemical group 0.000 claims description 24
- 125000003342 alkenyl group Chemical group 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 239000002781 deodorant agent Substances 0.000 claims description 19
- 230000001877 deodorizing effect Effects 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 2
- -1 dihydropyran epoxides Chemical class 0.000 description 103
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 59
- 230000015572 biosynthetic process Effects 0.000 description 27
- 239000003921 oil Substances 0.000 description 25
- 235000019198 oils Nutrition 0.000 description 25
- 238000003786 synthesis reaction Methods 0.000 description 24
- 150000001299 aldehydes Chemical class 0.000 description 17
- 239000000047 product Substances 0.000 description 16
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 229940022663 acetate Drugs 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 8
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 8
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 8
- 239000004327 boric acid Substances 0.000 description 8
- 239000002304 perfume Substances 0.000 description 8
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 7
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- QOUVUDUTJPGJNG-UHFFFAOYSA-N 3-methyl-2-methylidenebutanal Chemical compound CC(C)C(=C)C=O QOUVUDUTJPGJNG-UHFFFAOYSA-N 0.000 description 6
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- 150000002825 nitriles Chemical class 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
- 230000035807 sensation Effects 0.000 description 5
- 235000019615 sensations Nutrition 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- KMPQYAYAQWNLME-UHFFFAOYSA-N undecanal Chemical compound CCCCCCCCCCC=O KMPQYAYAQWNLME-UHFFFAOYSA-N 0.000 description 5
- BGTBFNDXYDYBEY-FNORWQNLSA-N 4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one Chemical compound C\C=C\C(=O)C1=C(C)CCCC1(C)C BGTBFNDXYDYBEY-FNORWQNLSA-N 0.000 description 4
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 4
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 4
- 229930040373 Paraformaldehyde Natural products 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 235000014443 Pyrus communis Nutrition 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 150000004808 allyl alcohols Chemical class 0.000 description 4
- DCTOHCCUXLBQMS-UHFFFAOYSA-N cis-undecene Natural products CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 4
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 description 4
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N hydroxymethylethylene Natural products OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
- 125000005188 oxoalkyl group Chemical group 0.000 description 4
- 229920002866 paraformaldehyde Polymers 0.000 description 4
- 150000003335 secondary amines Chemical class 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 150000003505 terpenes Chemical class 0.000 description 4
- 235000007586 terpenes Nutrition 0.000 description 4
- HQKGJGUSPDNTGY-UHFFFAOYSA-N undec-1-ene Chemical compound [CH2]CCCCCCCCC=C HQKGJGUSPDNTGY-UHFFFAOYSA-N 0.000 description 4
- VXIRJOHCLXLYOA-UHFFFAOYSA-N 2-methylidenehexan-1-ol Chemical compound CCCCC(=C)CO VXIRJOHCLXLYOA-UHFFFAOYSA-N 0.000 description 3
- IWEWQGKFUYQGSN-UHFFFAOYSA-N 2-methylidenehexanal Chemical compound CCCCC(=C)C=O IWEWQGKFUYQGSN-UHFFFAOYSA-N 0.000 description 3
- YGGIQHOTDHRHEM-UHFFFAOYSA-N 3,3-dimethyl-2-(prop-2-enoxymethyl)but-1-ene Chemical compound C(C=C)OCC(=C)C(C)(C)C YGGIQHOTDHRHEM-UHFFFAOYSA-N 0.000 description 3
- OHCLSNSCCQEQTA-UHFFFAOYSA-N 3-methyl-2-methylidenebutan-1-ol Chemical compound CC(C)C(=C)CO OHCLSNSCCQEQTA-UHFFFAOYSA-N 0.000 description 3
- WRYLYDPHFGVWKC-UHFFFAOYSA-N 4-terpineol Chemical compound CC(C)C1(O)CCC(C)=CC1 WRYLYDPHFGVWKC-UHFFFAOYSA-N 0.000 description 3
- VCGNHFNDKSMFCB-UHFFFAOYSA-N 5-methyl-4-methylidenehexan-3-ol Chemical compound CCC(O)C(=C)C(C)C VCGNHFNDKSMFCB-UHFFFAOYSA-N 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006959 Williamson synthesis reaction Methods 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 3
- 150000001241 acetals Chemical class 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- HVRLXWOYMKPQLB-UHFFFAOYSA-N hept-1-ene Chemical compound CCCC[CH]C=C HVRLXWOYMKPQLB-UHFFFAOYSA-N 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- UWKAYLJWKGQEPM-LBPRGKRZSA-N linalyl acetate Chemical compound CC(C)=CCC[C@](C)(C=C)OC(C)=O UWKAYLJWKGQEPM-LBPRGKRZSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- ULDHMXUKGWMISQ-VIFPVBQESA-N (+)-carvone Chemical compound CC(=C)[C@H]1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-VIFPVBQESA-N 0.000 description 2
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 2
- XHXUANMFYXWVNG-UHFFFAOYSA-N (+/-)-Menthyl acetate Chemical compound CC(C)C1CCC(C)CC1OC(C)=O XHXUANMFYXWVNG-UHFFFAOYSA-N 0.000 description 2
- XHXUANMFYXWVNG-ADEWGFFLSA-N (-)-Menthyl acetate Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(C)=O XHXUANMFYXWVNG-ADEWGFFLSA-N 0.000 description 2
- ULDHMXUKGWMISQ-SECBINFHSA-N (-)-carvone Chemical compound CC(=C)[C@@H]1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-SECBINFHSA-N 0.000 description 2
- MBDOYVRWFFCFHM-SNAWJCMRSA-N (2E)-hexenal Chemical compound CCC\C=C\C=O MBDOYVRWFFCFHM-SNAWJCMRSA-N 0.000 description 2
- SSNZFFBDIMUILS-ZHACJKMWSA-N (E)-dodec-2-enal Chemical compound CCCCCCCCC\C=C\C=O SSNZFFBDIMUILS-ZHACJKMWSA-N 0.000 description 2
- ZCHHRLHTBGRGOT-SNAWJCMRSA-N (E)-hex-2-en-1-ol Chemical compound CCC\C=C\CO ZCHHRLHTBGRGOT-SNAWJCMRSA-N 0.000 description 2
- HRHOWZHRCRZVCU-AATRIKPKSA-N (E)-hex-2-enyl acetate Chemical compound CCC\C=C\COC(C)=O HRHOWZHRCRZVCU-AATRIKPKSA-N 0.000 description 2
- BSAIUMLZVGUGKX-BQYQJAHWSA-N (E)-non-2-enal Chemical compound CCCCCC\C=C\C=O BSAIUMLZVGUGKX-BQYQJAHWSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 125000006017 1-propenyl group Chemical group 0.000 description 2
- IAIHUHQCLTYTSF-UHFFFAOYSA-N 2,2,4-trimethylbicyclo[2.2.1]heptan-3-ol Chemical compound C1CC2(C)C(O)C(C)(C)C1C2 IAIHUHQCLTYTSF-UHFFFAOYSA-N 0.000 description 2
- DBZAKQWXICEWNW-UHFFFAOYSA-N 2-acetylpyrazine Chemical compound CC(=O)C1=CN=CC=N1 DBZAKQWXICEWNW-UHFFFAOYSA-N 0.000 description 2
- CFAKWWQIUFSQFU-UHFFFAOYSA-N 2-hydroxy-3-methylcyclopent-2-en-1-one Chemical compound CC1=C(O)C(=O)CC1 CFAKWWQIUFSQFU-UHFFFAOYSA-N 0.000 description 2
- PVDIIWUJHVIZTK-UHFFFAOYSA-N 2-methylideneundecanal Chemical compound CCCCCCCCCC(=C)C=O PVDIIWUJHVIZTK-UHFFFAOYSA-N 0.000 description 2
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- IKDIJXDZEYHZSD-UHFFFAOYSA-N 2-phenylethyl formate Chemical compound O=COCCC1=CC=CC=C1 IKDIJXDZEYHZSD-UHFFFAOYSA-N 0.000 description 2
- JMMZCWZIJXAGKW-UHFFFAOYSA-N 2M2P Natural products CCC=C(C)C JMMZCWZIJXAGKW-UHFFFAOYSA-N 0.000 description 2
- FAGYGFPZNTYLAO-UHFFFAOYSA-N 3,7-dimethyl-2-methylideneoct-6-enal Chemical compound O=CC(=C)C(C)CCC=C(C)C FAGYGFPZNTYLAO-UHFFFAOYSA-N 0.000 description 2
- 125000004975 3-butenyl group Chemical group C(CC=C)* 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
- PCBSXBYCASFXTM-UHFFFAOYSA-N 4-(4-Methoxyphenyl)-2-butanone Chemical compound COC1=CC=C(CCC(C)=O)C=C1 PCBSXBYCASFXTM-UHFFFAOYSA-N 0.000 description 2
- CWRKZMLUDFBPAO-SREVYHEPSA-N 4-Decenal Chemical compound CCCCC\C=C/CCC=O CWRKZMLUDFBPAO-SREVYHEPSA-N 0.000 description 2
- OALYTRUKMRCXNH-UHFFFAOYSA-N 5-pentyloxolan-2-one Chemical compound CCCCCC1CCC(=O)O1 OALYTRUKMRCXNH-UHFFFAOYSA-N 0.000 description 2
- AUBLFWWZTFFBNU-UHFFFAOYSA-N 6-butan-2-ylquinoline Chemical compound N1=CC=CC2=CC(C(C)CC)=CC=C21 AUBLFWWZTFFBNU-UHFFFAOYSA-N 0.000 description 2
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- ZCTQGTTXIYCGGC-UHFFFAOYSA-N Benzyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 description 2
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- 240000000560 Citrus x paradisi Species 0.000 description 2
- 235000017788 Cydonia oblonga Nutrition 0.000 description 2
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- VLSVVMPLPMNWBH-UHFFFAOYSA-N Dihydro-5-propyl-2(3H)-furanone Chemical compound CCCC1CCC(=O)O1 VLSVVMPLPMNWBH-UHFFFAOYSA-N 0.000 description 2
- PXIKRTCSSLJURC-UHFFFAOYSA-N Dihydroeugenol Chemical compound CCCC1=CC=C(O)C(OC)=C1 PXIKRTCSSLJURC-UHFFFAOYSA-N 0.000 description 2
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- BJIOGJUNALELMI-UHFFFAOYSA-N trans-isoeugenol Natural products COC1=CC(C=CC)=CC=C1O BJIOGJUNALELMI-UHFFFAOYSA-N 0.000 description 1
- WKJHMKQSIBMURP-UHFFFAOYSA-N tridecanenitrile Chemical compound CCCCCCCCCCCCC#N WKJHMKQSIBMURP-UHFFFAOYSA-N 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 239000010681 turmeric oil Substances 0.000 description 1
- KYWIYKKSMDLRDC-UHFFFAOYSA-N undecan-2-one Chemical compound CCCCCCCCCC(C)=O KYWIYKKSMDLRDC-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000016788 valerian Nutrition 0.000 description 1
- WRFZKAGPPQGDDQ-UHFFFAOYSA-N valeryl hexanoate Chemical compound CCCCCOC(=O)CCCCC WRFZKAGPPQGDDQ-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
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- RGVQNSFGUOIKFF-UHFFFAOYSA-N verdyl acetate Chemical compound C12CC=CC2C2CC(OC(=O)C)C1C2 RGVQNSFGUOIKFF-UHFFFAOYSA-N 0.000 description 1
- BALAUIYKESNHDW-UHFFFAOYSA-N verdyl propionate Chemical compound C1CC2C3C(OC(=O)CC)C=CC3C1C2 BALAUIYKESNHDW-UHFFFAOYSA-N 0.000 description 1
- 239000010679 vetiver oil Substances 0.000 description 1
- YEIGUXGHHKAURB-UHFFFAOYSA-N viridine Natural products O=C1C2=C3CCC(=O)C3=CC=C2C2(C)C(O)C(OC)C(=O)C3=COC1=C23 YEIGUXGHHKAURB-UHFFFAOYSA-N 0.000 description 1
- 239000001854 vitis vinifera oil white Substances 0.000 description 1
- 239000000341 volatile oil Substances 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
- 239000010457 zeolite Substances 0.000 description 1
- 229930007850 β-damascenone Natural products 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/202—Aliphatic compounds
- A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
- A61L2/16—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using chemical substances
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
- C07C29/40—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing carbon-to-metal bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/15—Unsaturated ethers containing only non-aromatic carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/75—Reactions with formaldehyde
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Description
但し、
R2が水素であるときには、R1はtert-ブチルではあり得ず、
R2が水素であるときには、R1はペンチルではあり得ない。
ウィリアムソンエーテル合成ステップを用いることにより、例えば、水素化ナトリウム及び/又は水酸化ナトリウム及び/又は水酸化カリウム等の塩基の存在下において、式(II)のアルコールを臭化アリル及び/又は塩化アリルと反応させることによる。それから、もたらされるエーテルは好ましくは蒸留によって精製される。
例えば水素化硼素ナトリウム若しくは水素化アルミニウムリチウムによる還元によるか、又は有機金属試薬、例えば適当なハロゲン化アルキルマグネシウムR2MgX、例えばMeMgClの求核付加によるか何れかである。
式(IV)のアルデヒドを、
ホルムアルデヒドとの反応に付して、式(III)の2-置換アクロレインを形成すること、
及び、
ホルムアルデヒド又はホルムアルデヒド源と反応させて、式(III)-(a)の2-置換アクロレインを形成するための方法も提供される。
アジョワン油、アミリス油、アルモワーズ油、アルテミシア油、バジル油、ビーズワックスアブソリュート、ベルガモット油、バーチタール油、ブラックペッパー油、ブラックペッパーオレオレジン、樟脳油、カナンガ油、キャラウェイ油、カルダモン油、ニンジン種子油、カストリウムアブソリュート、シダーリーフ油、シダーウッド油、セロリ種子油、カモミール油、シナモンバーク油、シナモンリーフ油、シスタスアブソリュート、シスタス油、シトロネラ油、シトロネラテルペン、クラリセージ油、精留クローブ油、ホワイトコニャック油、コリアンダー種子油、クミン種子油、サイプレス油、ダバナ油、ディル種子油、エレミ油、エレミレジノイド、ユーカリ油、ファーニードル油、ガルバナム油、ゼラニウム油、インディアンジンジャーオイル、グレープフルーツ油、ガイアックウッド油、グルユンバルサム、ジャスミンアブソリュート、ジャタマンシ油、ジュニパーベリー油、ジュニパーリーフ油、カチュール油、ラブダナムアブソリュート、ラブダナムレジノイド、ラベンダー油、レモン油、レモン油テルペン、レモングラス油、ライム油、リツエアクベバ油、リツエアクベバテルペン、チョーヤロバン(Lobhan choya)レジノイド、マンダリン油、ヨウシュハッカ(Mentha arvenis)油、ベルガモットミント油、ミモザアブソリュート、ミルラレジノイド、ナガルモタ油、ナツメグ油、オークモスアブソリュート、オークモスレジノイド、オリバナム油、オリバナムレジノイド、オレンジ油、オリガナム油、パルマローザ油、パチュリ油、ペパーミント油、ペルーバルサムレジノイド、プチグレン油、パインニードル油、ピンクペッパー油、ローズアブソリュート、ローズ油、ローズマリー油、サンダルウッド油、シーウィードアブソリュート、スペアミント油、スガンダコキラ油、スガンダマントリ油、タジェット油、トルーバルサムレジノイド、チューベローズアブソリュート、ターメリック油、テレビン油、バレリアン油、ベチバー油、ベチバーテルペン。
エステル、例えば:アルデヒドC16、アミルグリコール酸アリル、カプロン酸アリル、シクロヘキシルプロピオン酸アリル、ヘプタン酸アリル、フェノキシ酢酸アリル、酢酸イソアミル、安息香酸アミル、酪酸アミル、カプロン酸アミル、桂皮酸アミル、イソ吉草酸アミル、フェニル酢酸アミル、プロピオン酸アミル、サリチル酸イソアミル、アミリスアセテート、酢酸アニシル、酢酸ベンジル、安息香酸ベンジル、酪酸ベンジル、桂皮酸ベンジル、蟻酸ベンジル、イソ酪酸ベンジル、ベンジルイソオイゲノール、プロピオン酸ベンジル、サリチル酸ベンジル、チグリン酸ベンジル、酢酸ブチル、酪酸ブチル、ブチリル乳酸ブチル、酢酸カリオフィレン、酢酸セドリル、酢酸シンナミル、酪酸シンナミル、酢酸シス-3-ヘキセニル、安息香酸シス-3-ヘキセニル、カプロン酸シス-3-ヘキセニル、蟻酸シス-3-ヘキセニル、イソ酪酸シス-3-ヘキセニル、酪酸シス-3-ヘキセニル-2-メチル、プロピオン酸シス-3-ヘキセニル、サリチル酸シス-3-ヘキセニル、チグリン酸シス-3-ヘキセニル、酢酸シトロネリル、酪酸シトロネリル、蟻酸シトロネリル、イソ酪酸シトロネリル、プロピオン酸シトロネリル、チグリン酸シトロネリル、シクラブテ(Cyclabute)、シクロガルバネート、酢酸シクロヘキシルエチル、酢酸デシル、フタル酸ジブチル、マロン酸ジエチル、フタル酸ジエチル、酢酸ジヒドロミルセニル、オクタニル酢酸ジメチル、酢酸ジメチルフェニルエチルカルビニル、アジピン酸ジオクチル、フタル酸ジオクチル、酢酸ジメチルベンジルカルビニル、酪酸ジメチルベンジルカルビニル、酢酸エチルリナリル、2-メチル酪酸エチル、3-フェニルプロピオン酸エチル、酢酸エチル、アセト酢酸エチル、安息香酸エチル、酪酸エチル、カプリン酸エチル、カプロン酸エチル、カプリル酸エチル、桂皮酸エチル、ヘプタン酸エチル、酢酸エチルヘキシル、イソ酪酸エチル、ラウリン酸エチル、ペラルゴン酸エチル、フェノキシ酢酸エチル、フェニル酢酸エチル、フェニルグリシド酸エチル、プロピオン酸エチル、サフラン酸エチル、サリチル酸エチル、吉草酸エチル、酢酸オイゲニル、エバニール(Evernyl)、酢酸フェンキル、フロラマト(Floramat)、フレスコラト-ML(Frescolat-ML)、フラクトン、フルイテート、酢酸ゲラニル、酪酸ゲラニル、蟻酸ゲラニル、プロピオン酸ゲラニル、チグリン酸ゲラニル、ギブスコーン(Givescone)、酢酸グアイオール、エディオネート(Hedionate)、エディオン(Hedione)、ヘルベトライド(Helvetolide)、エルバネート(Herbanate)、酢酸ヘキシル、安息香酸ヘキシル、酪酸n-ヘキシル、カプロン酸ヘキシル、イソ酪酸ヘキシル、プロピオン酸ヘキシル、サリチル酸ヘキシル、酢酸イソボルニル、酢酸イソブチル、フェニル酢酸イソブチル、サリチル酸イソブチル、酢酸イソオイゲニル、酢酸イソノニル、イソペンチレート、2-メチル酪酸イソプロピル、ミリスチン酸イソプロピル、ジャスモニル(Jasmonyl)、リッファローム(Liffarome)、酢酸リナリル、マハゴネート(Mahagonate)、マンザネート(Manzanate)、酢酸メンタニル、酢酸メンチル、安息香酸メチル、酢酸2-メチルブチル、メチルカモミール、桂皮酸メチル、シクロゲラン酸メチル、炭酸メチルヘプチン、ラウリン酸メチル、炭酸メチルオクチン、フェニル酢酸メチル、サリチル酸メチル、2-メチル酪酸メチル、ネオフォリオン(Neofolione)、酢酸ノピル、酢酸オクテニル、酢酸オクチル、イソ酪酸オクチル、酢酸パラクレシル、イソ酪酸パラクレシル、フェニル酢酸パラクレシル、ペアーエステル、ペラナット、イソ酪酸フェノキシエチル、酢酸フェニルエチル、酪酸フェニルエチル、蟻酸フェニルエチル、イソ酪酸フェニルエチル、フェニル酢酸フェニルエチル、プロピオン酸フェニルエチル、サリチル酸フェニルエチル、チグリン酸フェニルエチル、イソ酪酸フェニルプロピル、酢酸プレニル、ロマンドライド(Romandolide)、セージシーテ(Sagecete)、酢酸スチラリル、プロピオン酸スチラリル、タンジェリノール(Tangerinol)、酢酸テルピニル、テサロン(Thesaron)、酢酸トランス-2-ヘキセニル、トロピケーテ(Tropicate)、ベルドックス(Verdox)、ベルジルアセテート、ベルジルプロピオネート、ベルテネックス(Vertenex)、ベチコールアセテート、酢酸ベチベリル、ヤスモリス(Yasmolys)。
2-((アリルオキシ)メチル)ヘキサ-1-エンの合成:
ヘキサナール(3.88kg,38.7mol,1eq.)を、撹拌しながら、37%ホルムアルデヒド(3.78kg,46.5mol,1.2eq.)水溶液、ジ-n-ブチルアミン(252g,1.95mol,0.05eq.)、及びp-アニス酸(295g,1.94mol,0.05eq.)の混合物に10~15℃で2hの時間を掛けて追加した。追加の完了後に、反応混合物を2hに渡って50℃で撹拌した。その後に、反応混合物を25℃に冷却し、有機相を分離し、水(3×2L)によって洗浄し、硫酸ナトリウム(250g)によって乾燥した。生成物をそのまま真空蒸留して(45~49℃/53mbar)、2-メチレンヘキサナール(3.98kg,91%)を無色の液体として与えた。
1H NMR (400 MHz, CDCl3): δ 0.91 (t, J = 7.2 Hz, 3H), 1.30-1.47 (m, 4H), 2.03-2.07 (m, 2H), 4.85-4.86 (m, 1H), 5.00 (m, 1H), 10.05 (s, 1H).
13C NMR (100 MHz, CDCl3): δ 13.6, 22.0, 27.3, 29.9, 133.7, 150.5, 194.5.
水素化硼素ナトリウム(383g,10.1mol,272meq.)を、撹拌しながら、2-メチレンヘキサナール(4.18kg,37.3mol,1eq.)及び水(5.60L)の混合物に10~15℃で4hの時間を掛けて追加した。それから、反応混合物を3hに渡って25℃で撹拌した。その後に、反応混合物を10%塩化水素水溶液(3L)によって希釈した。有機相を分離し、水(1×3L)、10%炭酸ナトリウム水溶液(1×3L)、及び塩水(1×3L)によって順次に洗浄した。有機相(4.13kg)を真空蒸留して(52~54℃/4mbar)、2-メチレンヘキサン-1-オール(3.94kg,92%)を無色の液体として与えた。
1H NMR (400 MHz, CDCl3): δ 0.91 (t, J = 7.2 Hz, 3H), 1.30-1.47 (m, 4H), 2.03-2.07 (m, 3H), 4.05 (s, 2H), 4.85-4.86 (m, 1H), 5.00 (m, 1H).
13C NMR (100 MHz, CDCl3): δ 13.8, 22.6, 32.8, 35.6, 65.4, 108.6, 149.0.
粉末水酸化カリウム(1.76kg,31.4mol,1.99eq.)を、2-メチレンヘキサン-1-オール(1.80kg,15.8mol,1eq.)及びテトラ-n-ブチル臭化アンモニウム(255g,791mmol,0.05eq.)の混合物に25℃で2hの時間を掛けて追加した。それから、塩化アリル(3.01kg,39.3mol)を撹拌しながら10~15℃で6hの時間を掛けて追加した。反応混合物を25℃で16hに渡って撹拌した。その後に、反応混合物をブフナー漏斗によって濾過し、固体をメチルtert-ブチルエーテル(1L)によって洗浄した。濾液を水(2L)、5%塩化水素水溶液(300mL)、5%炭酸ナトリウム水溶液(1L)、及び塩水(2L)によって順次に洗浄した。揮発性成分を減圧下で除去した(45℃/133mbar)。残渣(2.46kg)を真空蒸留して(34~36℃/3mbar)、2-((アリルオキシ)メチル)ヘキサ-1-エン(1.91kg,78%)を無色の液体として与えた。GC純度97.5%。
1H NMR (400 MHz, CDCl3): δ 0.91 (t, J = 7.2 Hz, 3H), 1.31-1.47 (m, 4H), 2.03-2.07 (m, 2H), 3.91-3.94 (s, 2H), 3.94-3.96 (m, 2H), 4.89 (s, 1H), 5.00 (s, 1H), 5.15-5.19 (m, 1H), 5.25-5.30 (m, 1H), 5.87-5.97 (m, 1H).
13C NMR (100 MHz, CDCl3): δ 12.6, 21.2, 28.5, 31.5, 69.5, 71.7, 109.8, 115.5, 133.5, 145.0.
2-((アリルオキシ)メチル)-3-メチルブタ-1-エンの合成:
3-メチルブタナール(391g,4.54mol)を、撹拌しながら、37%ホルムアルデヒド(368g,4.54mol)水溶液、ジn-ブチルアミン(30.0g,232mmol)、及びp-アニス酸(35.0g,230mmol)の混合物に追加した。それから、混合物を70℃で1hに渡って撹拌した。その後に、反応混合物を20℃に冷却し、飽和炭酸水素ナトリウム水溶液を追加した。有機相を分離し、生成物をそのまま蒸留によって精製して(105~106℃,1bar)、3-メチル-2-メチレンブタナール(53g,13%)を無色の液体として与えた。
水素化硼素ナトリウム(800mg,21.1mmol)を、分割して、撹拌しながら、ジクロロメタン(3mL)中の3-メチル-2-メチレンブタナール(5.00g,50.9mmol)及びメタノール(6mL)の混合物に0℃で追加した。それから、反応混合物を0℃で15minに渡って撹拌し、次に20℃における2hの撹拌をした。その後に、ガス形成が消えるまで、2M塩化水素水溶液を追加した。それから、塩化ナトリウム(2.40g,40.8mmol)を追加した。混合物を水によって希釈し、メチルtert-ブチルエーテルによって抽出した。有機相を分離し、塩水によって洗浄し、硫酸ナトリウムによって乾燥し、揮発性成分を減圧下で除去した(50℃,400mbar)。残渣をクーゲルロール蒸留によって蒸留して、3-メチル-2-メチレンブタン-1-オール(2.4g,48%)を無色の液体として与えた。
ミネラルオイル中の水素化ナトリウム60%の懸濁液(3.00g,75.0mmol)を、分割して、テトラヒドロフラン(50mL)中の3-メチル-2-メチレンブタン-1-オール(5.00g,49.9mmol)の溶液に4℃で窒素雰囲気において追加した。それから、臭化アリル(12.1g,100mmol)を4℃で追加した。反応混合物を20℃で3日に渡って撹拌した。それから、イソプロパノール(10mL)、次に水(10mL)を追加した。有機相を分離し、水相をメチルtert-ブチルエーテル(3×)によって抽出した。有機相を組み合わせ、揮発性成分を減圧下で除去した(50℃,6mbar)。残渣(6.00g)をクーゲルロール蒸留によって精製して(110℃,6mbar)、2-((アリルオキシ)メチル)-3-メチルブタ-1-エン(1.40g,20%)を無色の液体として与えた。
4-(アリルオキシ)-2-メチル-3-メチレンヘキサンの合成:
3-メチルブタナール(200g,2.32mol,1eq.)を、37%ホルムアルデヒド(207g,2.55mol,1.1eq.)水溶液、ジ-n-ブチルアミン(15.0g,116mmol,0.05eq.)、及びp-アニス酸(17.6g,116mmol,0.05eq.)の混合物に25℃で2hの時間を掛けて追加し、それから、反応混合物を70℃で4hに渡って加熱した。反応混合物を25℃に冷却し、有機相を分離し、水(3×100mL)によって洗浄し、硫酸ナトリウム(100g)によって乾燥した。混合物をそのまま真空蒸留して(42~45℃/100mbar)、3-メチル-2-メチレンブタナール(167g,73%)を無色の液体として与えた。
1H NMR (400 MHz, CDCl3): δ 1.01 (d, J = 7.2 Hz, 6H), 2.69-2.76 (m, 1H), 5.89 (s, 1H), 6.18 (d, J = 0.8 Hz, 1H), 9.46 (s, 1H).
13C NMR (100 MHz, CDCl3): δ 20.2, 24.2, 131.1, 155.6, 193.5.
テトラヒドロフラン(500mL)中の3-メチル-2-メチレンブタナール(100g,1.01mol,1eq.)の溶液を、撹拌しながら、テトラヒドロフラン中の塩化エチルマグネシウム2Mの予冷(-5℃)溶液(611g,1.22mol,1.21eq.)に5℃で2hの時間を掛けて追加した。反応混合物を3h掛けて25℃に温め、それから25℃で4hに渡って撹拌した。その後に、撹拌しながら、40%塩化アンモニウム水溶液(250mL)、次にメチルtert-ブチルエーテル(300mL)を追加した。それから、有機相を分離し、水相をメチルtert-ブチルエーテル(1×300mL)によって抽出した。組み合わせた有機相を塩水(100mL)によって洗浄し、硫酸ナトリウム (100g)によって乾燥した。揮発性成分を減圧下で除去し、残渣を真空蒸留して(45~50℃/7~10mbar)、5-メチル-4-メチレンヘキサン-3-オール(70.5g,54%)を無色の液体として与えた。
1H NMR (400 MHz, CDCl3): δ 0.85 (t, J = 7.6 Hz, 3H), 0.96 (d, J = 5.6 Hz, 3H), 1.01 (d, J = 7.2 Hz, 3H), 1.43-1.63 (m, 2H), 2.16-2.23 (m, 2H), 3.94-3.97 (m, 1H), 4.84 (s, 1H), 4.95 (s, 1H).
13C NMR (100 MHz, CDCl3): δ 8.3, 20.8, 20.9, 26.4, 28.3, 73.5, 105.3, 156.5.
粉末水酸化カリウム(131g,2.33mol,2eq.)を、撹拌しながら、5-メチル-4-メチレンヘキサン-3-オール(150g,1.17mol,1eq.)及び臭化テトラ-n-ブチルアンモニウム(18.7g,58.0mmol,50meq.)の混合物に25℃で1hの時間を掛けて追加した。それから、塩化アリル(224g,2.93mol,2.5eq.)を25~35℃で2hの時間を掛けて追加した。反応混合物を25℃で16hに渡って撹拌した。その後に、水(300mL)、次にメチルtert-ブチルエーテル(300mL)を追加した。有機相を分離し、水(3×300mL)によって洗浄し、硫酸ナトリウム(100g)によって乾燥した。揮発性成分を減圧下で除去した。残渣を真空蒸留して(52~59℃/7~13mbar)、4-(アリルオキシ)-2-メチル-3-メチレンヘキサン(78.7g,40.0%)を無色の液体として与えた。GC純度=96%。
1H NMR (400 MHz, CDCl3): δ 0.82 (t, J = 7.4 Hz, 3H), 0.96 (d, J = 6.8 Hz, 3H), 1.00 (d, J = 6.8 Hz, 3H), 1.47-1.54 (m, 2H), 2.13-2.20 (m, 1H), 3.53 (t, J = 6.8 Hz, 1H), 3.65-3.71 (m, 1H), 3.89-3.94 (m, 1H), 4.90 (s, 2H), 5.05-5.08 (m, 1H), 5.15-5.21 (m, 1H), 5.78-5.84 (m, 1H).
13C NMR (100 MHz, CDCl3): δ 9.2, 21.6, 22.7, 26.0, 28.2, 68.0, 83.2, 108.6, 115.2, 134.3, 154.5.
2-(アリルオキシ)-4-メチル-3-メチレンペンタンの合成
2-((アリルオキシ)メチル)ヘプタ-1-エンの合成
1H NMR (600 MHz, CDCl3): δ 0.89 (br. t, J = 7.0 Hz, 3H), 1.26-1.35 (m, 4H), 1.45 (quint, J = 7.4 Hz, 2H), 2.05 (t, J = 7.7 Hz, 2H), 3.92 (s, 2H), 3.96 (d, J = 5.5 Hz, 2H), 4.90 (s, 1H), 5.01 (s, 1H), 5.18 (d, J = 10.4 Hz, 1H), 5.28 (br. d, J = 17.2 Hz, 1H), 5.92 (ddt, J = 17.1, 10.8, 5.6 Hz, 1H).
13C NMR (600 MHz, CDCl3): δ 14.1, 22.6, 27.3, 31.6, 33.1, 70.9, 73.0, 111.1, 116.8, 134.9, 146.3.
2-((アリルオキシ)メチル)オクタ-1-エンの合成
1H NMR (600 MHz, CDCl3): δ 0.89 (br. t, J = 6.9 Hz, 3H), 1.29-1.47 (m, 6H), 1.44 (quint, J = 7.7 Hz, 2H), 2.05 (t, J = 7.7 Hz, 2H), 3.92 (s, 2H), 3.96 (br. d, J = 5.6 Hz, 2H), 4.90 (s, 1H), 5.00 (s, 1H), 5.18 (dd, J = 10.4, 1.5 Hz, 1H), 5.28 (br. dd, J = 17.2, 1.7 Hz, 1H), 5.89-5.96 (m, 1H).
13C NMR (600 MHz, CDCl3): δ 14.1, 22.6, 27.6, 31.8, 33.2, 70.9, 73.0, 111.1, 116.8, 134.9, 146.3.
2-((アリルオキシ)メチル)ウンデカ-1-エンの合成
ウンデカナール(1.70kg,10.0mol)を、37%ホルムアルデヒド(892g,11mol)水溶液、ジエタノールアミン(137g,1.30mol)、及び硼酸(8.11g,130mmol)の混合物に追加した。混合物を80℃で6hに渡って撹拌した。それから、混合物を20℃に冷却し、2M塩酸水溶液(80mL)、炭酸水素ナトリウム水溶液(80mL)、及び塩水(80mL)によって洗浄した。生成物をそのまま真空蒸留によって精製して(56~70℃/1mbar)、2-メチレン-1-ウンデカナール(1.50kg,82%)を無色の液体として与えた。
1H NMR (600 MHz, CDCl3): δ 0.89 (br. t, J = 7.0 Hz, 3H), 1.20-1.35 (m, 12H), 1.40-150 (m, 2H), 2.05 (t, J = 7.8 Hz, 2H), 3.91 (s, 2H), 3.96 (d, J = 5.6 Hz, 2H), 4.89 (s, 1H), 5.00 (s, 1H), 5.23 (br. ddd, J = 13.8, 11.8, 1.5 Hz, 2H), 5.89-5.96 (m, 1H).
13C NMR (600 MHz, CDCl3): δ 14.1, 22.7, 27.6, 29.3, 29.4, 29.5, 29.6, 31.9, 33.2, 70.9, 73.1, 111.1, 116.8, 134.9, 146.4.
2-((アリルオキシ)メチル)-3,7-ジメチルオクタ-1,6-ジエンの合成
シトロネラール(344g,2.23mol)を、撹拌しながら、パラホルムアルデヒド(87.0g,2.90mol)、ジエタノールアミン(16.4g,16.0mmol)、及び安息香酸(19.1g,16.0mmol)の混合物に追加した。それから、混合物を90℃で6hに渡って撹拌した。その後に、塩水を追加し、有機相を分離して、3,7-ジメチル-2-メチレンオクタ-6-エナールをそのまま与えた(398g,92%)。
1H NMR (600 MHz, CDCl3): δ 1.05 (d, J = 6.9 Hz, 3H), 1.30-1.53 (m, 2H), 1.59 (s, 3H), 1.68 (s, 3H), 1.95 (br. q, J = 7.5 Hz, 2H), 2.19 (sext, J = 6.9 Hz, 1H), 3.94 (s, 2H), 3.97 (d, J = 5.5 Hz, 2H), 4.91 (s, 1H), 5.05 (d, J = 1.4 Hz, 1H), 5.09 (br. t, J = 5.8 Hz, 1H), 5.18 (br. dd, J = 10.4, 1.4 Hz, 1H), 5.28 (br. dd, J = 17.2, 1.6 Hz, 1H), 5.89-5.96 (m, 1H).
13C NMR (600 MHz, CDCl3): δ 17.7, 19.9, 25.7, 25.9, 35.7, 36.5, 71.0, 72.0, 110.0, 116.8, 124.6, 131.4, 134.9, 150.9.
次の例9から11では、例1の化合物を3つの異なる組成物に包含した。0.3wt%香料組成物で添加したシャワージェルから、嗅覚的な評価をした。
Claims (6)
- 式(I)の化合物が2-((アリルオキシ)メチル)ヘキサ-1-エンである、請求項1に記載のフレグランス、フレーバー、及び/又は脱臭/マスキング組成物。
- 式(I)の化合物の含量が0.0001及び95wt%の間に含まれる、請求項1又は2に記載のフレグランス、フレーバー、及び/又は脱臭/マスキング組成物。
- 少なくとも1つのエステル及び/又は1つのアルコールを含む、請求項1~3の何れか1項に記載のフレグランス、フレーバー、及び/又は脱臭/マスキング組成物。
- エステル(単数若しくは複数)及び/又はアルコール(単数若しくは複数)と併せた式(I)の化合物(単数又は複数)の合計含量が、25wt%超である、請求項4に記載のフレグランス、フレーバー、及び/又は脱臭/マスキング組成物。
- 香り付き又はフレーバー付き製品への、請求項1~5の何れか1項に記載のフレグランス、フレーバー、及び/又は脱臭/マスキング組成物の使用。
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